- Pro-apoptotic activity of new triterpenoid saponins from the roots of Albizia adianthifolia (Schumach.) W.Wight
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As part of our study of the proapoptotic function of saponins from Cameroonian's Albizia genus, phytochemical investigation of the roots of Albizia adianthifolia led to the isolation of three new triterpenoid saponins, named adianthifoliosides G–I (1–3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid-28-O-β-D-xylopyranosyl-(1 → 3)-[5-O-acetyl-α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (1), 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (2), and 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-β-D-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (3). The apoptotic effect of saponins 1–3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1–3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner.
- Noté, Olivier Placide,Kamto, Eutrophe Le Doux,Toukea, Daniel Djou,Aouazou, Sarah Ali,Mbing, Joséphine Ngo,Muller, Christian Dominique,Guillaume, Dominique,Pegnyemb, Dieudonné Emmanuel
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- Nebulosides A-B, novel triterpene saponins from under-ground parts of Gypsophila arrostii Guss. var. nebulosa
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A bioassay-guided phytochemical analysis of the triterpene saponins from under ground parts of Gypsophila arrostii var. nebulosa allowed the isolation of two triterpene saponins; nebuloside A, B based on gypsogenin and quillaic acid aglycone. Two new oleanane type triterpenoid saponins (nebuloside A, B) and three known saponins (1-3) were isolated from the root bark of Gypsophila arrostii var. nebulosa. The structures of the two new compounds were elucidated as 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]- β-d-glucuronopyranosyl quillaic acid 28-O-β-d-glucopyranosyl- (1→3)-[β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)] -α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside A) and 3-O-β-d-xylopyranosyl-(1→3)-[β-d- galactopyranosyl(1→3)-β-d-galactopyranosyl-(1→2)] -β-d-glucuronopyranosyl gypsogenin 28-O-β-d-glucopyranosyl-(1→3)- [β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)] -α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside B), on the basis of extensive spectral analysis and chemical evidence. Nebuloside A and B showed toxicity enhancing properties on saporin a type-I RIP without causing toxicity by themselves at 15 μg/mL.
- Arslan, Idris,Celik, Ali,Melzig, Matthias F.
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- Three new spirostanol glycosides from Helleborus thibetanus
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An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1–3). Their structures were elucidated by extensive analysis of 1 D, 2 D NMR spectra, together with IR and MS met
- Li, Zhang-Peng,Su, Yan-Fang,Wei, Zi-Ye,Yang, Feng-Ying,Zhang, Hui
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- Cytotoxic triterpenoid saponins from husks of Aesculus californica (Spach) Nutt.
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Fifteen polyhydroxyoleanene saponins, aesculiosides C1-C15 (1-15), were isolated from husks of Aesculus californica. Their structures were established by extensive spectroscopic and chemical analyses. The triterpenoid saponins from A. californica have greater structural diversity than those from any other investigated species thus far in the genus Aesculus. The chemotaxonomic characteristic of aesculiosides C1-C15 is that the unit attached to the C-3 of the aglycone is a glucopyranosyl moiety, instead of a glucuronopyranosyl group in the saponins that have been isolated from other Aesculus species. The saponins isolated from A. californica then provide important evolutionary and chemotaxonomic knowledge of the Aesculus genus, a well-known intercontinental disjunct genus in the Northern hemisphere. Aesculiosides C1-C15 (1-15) showed cytotoxicity to human non-small cell lung tumor (A549) with GI50 ranged from 3.76 to >25 μM.
- Yuan, Wei,Wang, Ping,Su, Zushang,Wang, Victoria S.,Li, Shiyou
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- Glycosides of polygalacic acid from the stem barks of Piper guineense Schum and Thonn
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In a continuation of our study on constituents of P. guineense now focusing on the search for saponins, phytochemical investigation of the n-BuOH fraction of P. guineense stem bark led to the isolation of three previously undescribed triterpenoid saponins, named guineenosides A─C (1─3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (1), 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (2), and 3-O-{α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-[α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (3). This is the first report of triterpenoid saponins from P. guineense.
- Le Doux Kamto, Eutrophe,Noté, Olivier Placide,Kinyok, Mc Jesus,Wilhelm, Anke,Mbing, Joséphine Ngo,Antheaume, Cyril,de Théodore Atchadé, Alex,Pegnyemb, Dieudonné Emmanuel,Ndinteh, Derek Tantoh,Haddad, Mohamed,Bonnet, Susan L.
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- Two new saponins from Thalictrum fortunei
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Two new cycloartane glycosides were isolated from the aerial parts of Thalictrum fortunei (Ranunculaceae). The chemical structures of these compounds were elucidated as 3-O-β-D-glucopyranosyl (1 → 4)-β-D- fucopyranosyl-(22S,24Z)-cycloart-24-en-3β,22,26,30
- Zhang, Xian-Tao,Ma, Shu-Wei,Jiao, Hao-Yan,Zhang, Qing-Wen
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- Dolabellane diterpene and three cycloartane glycosides from Thalictrum squarrosum
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A new dolabellane diterpene glycoside, named squoside A, and three new cycloartane glycosides, named squarrosides V, VI, and VII, have been isolated from the dried aerial parts of Thalictrum squarrosum (Ranunculaceae). Their structures were determined by
- Yoshimitsu, Hitoshi,Miyashita, Hiroyuki,Nishida, Makiko,Mineno, Tomoko,Nohara, Toshihiro
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- Dammarane-type saponins from leaves of Ziziphus spina-christi
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Phytochemical profiling of Ziziphus spina-christi leaves led to the characterization of 10 dammarane-type saponins and 12 phenolic compounds. Isolation was achieved by gel chromatography on Sephadex LH20, open column chromatography on silica gel, and semi-preparative HPLC with PDA and ELSD detectors. Structural characterization was performed by extensive 1D and 2D NMR, mass spectrometry, and by GC-MS of sugar derivatives. A biosynthetic pathway leading to three previously undescribed sapogenins is proposed. The saponin profiles in Z.?spina-christi leaves of four different origins were compared by means of HPLC-ESIMS.
- Bozicevic, Alen,De Mieri, Maria,Di Benedetto, Angela,Gafner, Frank,Hamburger, Matthias
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- Flavonoids isolated from the fresh sweet fruit of Averrhoa carambola, commonly known as star fruit
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Thirteen flavonoids were isolated from the fresh sweet fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit, and their structures were determined by spectroscopic and chemical methods. 8-Carboxymethyl-(+)-epicatechin methyl ester, pinobanksin 3-O-β-D-glucoside, and carambolasides M–Q were undescribed structures. (+)-Epicatechin, aromadendrin 3-O-β-D-glucoside, helicioside A, taxifolin 3′-O-β-D-glucoside, galangin 3-O-rutinoside, and isorhamnetin 3-O-rutinoside were reported from this species for the first time. Pinobanksin 3-O-β-D-glucoside and carambolasides M–Q showed more potent 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation scavenging activity (IC50 = 5.3–2.3 μM) than L-ascorbic acid (10.5 μM). Further, (+)-epicatechin, pinobanksin 3-O-β-D-glucoside, isorhamnetin 3-O-rutinoside, and carambolasides O–Q exhibited weak porcine pancreatic lipase inhibitory activity.
- Jia, Xuchao,Xie, Haihui,Jiang, Yueming,Wei, Xiaoyi
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- Furostane Series Asterosaponins and Other Unusual Steroid Oligoglycosides from the Tropical Starfish Pentaceraster regulus
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Seven new asterosaponins, pentaregulosides A-G (1-7), including two furostane-type steroid oligoglycosides (2, 3), along with four previously known compounds (8-11) were isolated from the ethanolic extract of the starfish Pentaceraster regulus, collected off the coast of Vietnam. The structures of 1-7 were elucidated by extensive NMR and ESIMS techniques as well as chemical transformations. The aglycons of compounds 1 and 3 have not previously been observed in starfish steroid oligoglycosides, while the aglycons of compounds 2 and 4-6 are very rare for this structural group. Compound 1 exhibited cytotoxic activity with an IC50 value of 6.4 ± 0.3 μM against RAW 264.7 murine macrophages. In contrast, nontoxic asterosaponins 3, 4, and 5 showed a potential immunomodulatory action at a concentration of 5 μM, reducing by 40%, 28%, and 55%, respectively, reactive oxygen species formation in the RAW 264.7 cells, co-stimulated with the pro-inflammatory endotoxic lipopolysaccharide from E. coli.
- Kicha, Alla A.,Kalinovsky, Anatoly I.,Ivanchina, Natalia V.,Malyarenko, Timofey V.,Dmitrenok, Pavel S.,Kuzmich, Alexandra S.,Sokolova, Ekaterina V.,Stonik, Valentin A.
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- Bisdesmosidic saponins from securidaca longepedunculata roots: Evaluation of deterrency and toxicity to coleopteran storage pests
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Powdered dry root bark of Securidaca longepedunculata was mixed with maize and cowpea and effectively reduced the numbers of Sitophilus zeamais and Callosobruchus maculatus emerging from these commodities, respectively, more than 9 months after treatment.
- Stevenson, Philip C.,Dayarathna, Thamara K.,Belmain, Steven R.,Veitch, Nigel C.
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- Barrigenol triterpenes from the husks of Xanthoceras sorbifolia Bunge and their antitumor activities
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Barrigenol-like triterpenoids containing angeloyl residues in their structures are unusual natural products. To discover the chemical constituents responsible for the antitumor activity of Xanthoceras sorbifolia Bunge, the present study was carried out using the husk of this crop. Ten angeloyl barrigenol triterpenoids, including seven new (1-7) and three known compounds (8-10), were isolated from the active fraction via the bioassay-guided method. The structures of the compounds were established on the basis of spectral analysis, especially according to the data afforded by two digital-NMR and high-resolution mass spectra experiments. Compounds 1-10 exhibited varying degrees of cytotoxicity toward the human hepatoma cell line (HepG2), the human colorectal cancer cell line (HCT116) and the human glioma cell line (U87-MG). New compounds 3, 6, and 7 and known compounds 8, and 10 showed inhibitory activities similar to those of the positive control (doxorubicin hydrochloride). Cell cycle and apoptosis analysis of compound 8 revealed that it could suppress U87-MG cell proliferation by inducing apoptosis in the early period of exposure and then promote arrest at the G0/G1 phase.
- Wang, Da,Su, Dan,Li, Xian-Zhe,Liu, Dan,Xi, Rong-Gang,Gao, Hui-Yuan,Wang, Xiao-Bo
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- Cylindroside A, a new triterpenoid saponin from Cylindrokelupha dalatensis and its cytotoxic activity
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A new triterpenoid saponin, named cylindroside A (1), was isolated from the seeds of Cylindrokelupha dalatensis (Kosterm.) T.L. Wu by using chromatographic method. The structure of 1 was established by comprehensive spectroscopic analysis and chemical degradation. Compound 1 displayed significant antitumor activity in vitro against BCG and MCF-7 cancer cell lines and IC50 values were 4.17 ± 0.23 and 3.07 ± 0.66 μM by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method, respectively.
- Zhou, Wen-Bin,Liu, Jie,Xing, Shuang,Zhang, Yun,Xiong, Guo-Ling,Luo, Qing-Liang,Ma, Bai-Ping,Yang, Ming-Hui,Liu, Ping
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- Two new flavonoid–triterpene saponin meroterpenoids from Clinopodium chinense and their protective effects against anoxia/reoxygenation-induced apoptosis in H9c2 cells
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Two new flavonoid–triterpene saponin meroterpenoids, clinoposides G (1) and H (2) were isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze. Their structures were elucidated through spectroscopic and electronic circular dichroism (ECD) analyses. Compounds 1 and 2 were evaluated for their protective effects against anoxia/reoxygenation(A/R)-induced injury in H9c2 cells. A/R treatment severely injured the H9c2 cells, which was accompanied by apoptosis. Both 1 and 2 pretreatment significantly inhibited cell injury and apoptosis, improved mitochondrial membrane potential, increased activities of antioxidant enzymes, and reduced the levels of the inflammatory cytokines. In addition, the presence of 1 and 2 significantly decreased the protein level of p65 and increased the level of Nrf2 in cell nucleus. Unique chemical structure and good biological activity of 1 and 2 elucidated the potential of meroterpenoids as a promising reagent for treating heart disease.
- Zhu, Yin-Di,Chen, Rong-Chang,Wang, Hong,Jiang, Hai,Huang, Xue-Li,Zhang, Mei-Ling,Li, Ling-Yu,Hu, Zhen,Xu, Xu-Dong,Wang, Chao-Jie,Ye, Xiao-Xia,Yang, Jun-Shan
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- Heptyl vicianoside and methyl caramboside from sour star fruit
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Two new alkyl glycosides, heptyl vicianoside (1) and methyl 2-O-β-d-fucopyranosyl-α-l-arabinofuranoside (methyl caramboside, 4), were isolated from the sour fruit of Averrhoa carambola L. (Oxalidaceae), along with octyl vicianoside (2), cis-3-hexenyl rutinoside (3), and methyl α-d-fructofuranoside (5). Their structures were determined by spectroscopic and chemical methods. Compounds 2, 3, and 5 were obtained from the genus Averrhoa for the first time. All the compounds were evaluated for in vitro α-glucosidase, pancreatic lipase, and acetylcholinesterase inhibitory activities, but none of them were potent.
- Yang, Dan,Jia, Xuchao,Xie, Haihui
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- A new triterpenoid saponin from Clinopodium chinense (Benth.) O. Kuntze
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A new triterpene saponin, 3β,16β,23,28β,30β-pentahydroxyl-olean-11,13(18)-dien-3β-yl-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→3)]-β-d-fucopyranoside, was named Clinoposaponin D (1), together with six known triterpene saponins, buddlejasaponin IVb (2), buddlejasaponin IVa (3), buddlejasaponin IV (4), clinopodisides D (5), 11,16β,23,28-Tetrahydroxyolean-12-en-3β-yl-[β-d-glucopyranosyl-(1→2)]-[β-d-glucopyranosyl-(1→3)]-β-d-fucopyranoside (6) and prosaikogenin A (7), and two known triterpenes, saikogenin A (8) and saikogenin F (9) were isolated from Clinopodium chinense (Benth.) O. Kuntze. Their structures were elucidated on the basis of 1D, 2D NMR and MS analysis. Meanwhile, the effects of all compounds on rabbit platelet aggregation and thrombin time (TT) were investigated in vitro. Compounds 4 and 7 had significant promoting effects on platelet aggregation with EC50 value at 53.4 and 12.2 M, respectively. In addition, the highest concentration (200 M) of compounds 2 and 9 shortened TT by 20.6 and 25.1%, respectively.
- Zeng, Biao,Liu, Guang-Da,Zhang, Bao-Bao,Wang, Shan-Shan,Ma, Rui,Zhong, Bei-Shan,He, Bai-Qiu,Liang, Yan,Wu, Fei-Hua
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- Three new cytotoxic oleanane triterpenoid saponins from Cylindrokelupha dalatensis
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Three new minor oleanane triterpenoid saponins, cylindrosides B (1), C (2), and D (3), were isolated from the seed of Cylindrokelupha dalatensis using chromatographic method. Their structures were established on the basis of the chemical and spectroscopic evidences. They displayed significant antitumor activity in vitro against HL60 cancer cell lines and IC50 values were 7.15?±?0.63, 10.07?±?0.97, and 4.74?±?0.57?μM, respectively, by MTT method.
- Yan, Meng-Yun,Liu, Jie,Xing, Shuang,Xiong, Guo-Ling,Pei, Ling-Peng,Ma, Bai-Ping,Liu, Ping,Zhou, Wen-Bin
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- Oleanane triterpene saponins with cardioprotective activity from Clinopodium polycephalum
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Two new triterpene saponins, clinopodiside VI (1) and saikosaponin c (2), along with six known saikosaponins (3–8), were isolated from the plant of Clinopodium polycephalum. Compounds 1–3 showed moderate inhibition against H9c2 cell damage induced by Hsu
- Hu, Yu-Xia,Zhang, Wei,Zhang, Wen,Zhu, Yin-Di,Ma, Guo-Xu,Zhu, Nai-Liang,Sun, Wen,Ma, Ze-Xin,Yu, Shi-Chun,Xu, Xu-Dong,Chen, Kai-Tuo,Yang, Jun-Shan
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- New acylated triterpene saponins from the roots of Securidaca inappendiculata Hassk
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Two new acylated triterpene saponins, named as securioside C (1), securioside D (2), and one pair of isomers 3/4, the (Z)-isomer securioside E (3) being new, together with a known triterpene saponin polygalasaponin XLIV (4) were isolated from the roots of Securidaca inappendiculata Hassk. Their structures were established by HRESIMS, 1D and 2D NMR experiments and comparison of their NMR data with previous reported data. In addition, Compounds 1-2, 3/4, 4 were evaluated for cytotoxicities against LLC (Lewis lung carcinoma) and MCF-7 (human breast cancer) cell lines. Compounds 1 and 2 exhibited moderate cytotoxic activities against LLC cells with IC50 values of 45.56 μM and 85.98 μM.
- Zha, Haiyan,Wang, Zhi,Yang, Xuedong,Jin, Daqing,Hu, Licui,Zheng, Wenfeng,Xu, Lizhen,Yang, Shilin
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- Phenotype-specific apoptosis induced by three new triterpenoid saponins from Albizia glaberrima (Schumach. & Thonn.) Benth
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As part of our search of new bioactive saponins from Cameroonian medicinal plants, phytochemical investigation of the roots of Albizia glaberrima led to the isolation of three new oleanane-type saponins, named glaberrimosides A-C (1-3). Their structures were established by direct interpretation of their spectral data, mainly HRESIMS, 1D NMR (1 H, 13C NMR, and DEPT) and 2D NMR (COSY, ROESY, HSQC and HMBC) as 3-O-[α-l-arabinopyranosyl-(1 → 6)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]-28-O-[β-d-glucopyranosyl-(1 → 6)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]-oleanolic acid (1), 3-O-[α-l-arabinopyranosyl-(1 → 6)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]-28-O-[β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl]-oleanolic acid (2), and 3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl]-28-O-[β-d-glucopyranosyl-(1 → 6)-[β-d-fucopyranosyl-(1 → 2)]-β-d-glucopyranosyl]-oleanolic acid (3). The pro-apoptotic effect of the three saponins was evaluated on three human cell lines (pancreatic carcinoma AsPC-1, hematopoietic monocytic THP-1, and human fibroblast cell line BJ). Saponins 1-3 specifically induced apoptosis of pancreatic carcinoma cell (AsPC-1) in a dose-dependent manner. More interestingly, there were inactive on monocytic (THP-1) and normal human fibroblast (BJ) cell lines.
- Noté, Olivier Placide,Azouaou, Sarah Ali,Simo, Line,Antheaume, Cyril,Guillaume, Dominique,Pegnyemb, Dieudonné Emmanuel,Muller, Christian Dominique,Lobstein, Annelise
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- Isolation of chemical constituents with anti-inflammatory activity from Reineckia carnea herbs
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Three new saponins (1–3), a new natural product (4) and six other known compounds (5–10) were isolated from the whole Reineckia carnea plant. Their structures were established by comparison of their NMR spectra and MS data with literature data. In addition, all the isolated compounds were evaluated in vitro for anti-inflammatory activities against LPS-stimulated nitric oxide (NO) production in RAW 264.7 macrophages. Compounds 1–4 exhibited anti-inflammatory activities with IC50 values of 37.5 μM, 31.4 μM, 34.6 μM, and 56.1 μM, respectively. Furthermore, compounds 5–10 showed anti-inflammatory activities with IC50 values ranging from 20.3 to 42.9 μM.
- Xu, Xu,Tan, Ting,Zhang, Jing,Li, Zhi-Feng,Yang, Shi-Lin,Wen, Quan,Feng, Yu-Lin
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- Steroidal glycosides from Furcraea foetida and their cytotoxic activity
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Two new spirostanol glycosides (1, 2) and a new furostanol glycoside (3), together with nine known steroidal glycosides (4-12) were isolated from the leaves of Furcraea foetida (Agavaceae). The structures of the new compounds were determined by spectrosco
- Yokosuka, Akihito,Sano, Tomoe,Hashimoto, Ken,Sakagami, Hiroshi,Mimaki, Yoshihiro
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- Three new steroidal saponins from Helleborus thibetanus
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Three new steroidal saponins including two spirostanol glycosides (1–2) and one furostanol glycoside 1-sulphate (3) were isolated from the dried roots and rhizomes of Helleborus thibetanus. Structures of the compounds were determined on the basis of extensive use of 1-D and 2-D NMR experiments, together with HR–ESI–MS and IR measurements, as well as the results of acid hydrolysis. Compounds 1–2 represented steroidal saponins with an unusual substitution pattern, which possessed a double bond at C-25 and were glycosylated at 1-OH.
- Zhang, Hui,Su, Yan-Fang,Yang, Feng-Ying
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- Steroidal saponins from the leaves of Cordyline fruticosa (L.) A. Chev. and their cytotoxic and antimicrobial activity
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Three new steroidal saponins, spirosta-5,25(27)-diene-1β,3β-diol- 1-O-α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranoside (fruticoside H) 1, 5α-spirost-25(27)-ene-1β,3β-diol-1-O-α-l- rhamnopyranosyl-(1→2)-(4-O-sulfo)-β-d-fucopyranoside (fruticoside I) 2, and (22S)-cholest-5-ene-1β,3β,16β,22-tetrol 1-O-β-galactopyranosyl-16-O-α-l-rhamnopyranoside (fruticoside J) 3, together with the known quercetin 3-O-β-d-glucopyranoside, quercetin 3-O-[6-trans-p-coumaroyl]-β-d-glucopyranoside, quercetin 3-rutinoside, apigenin 8-C-β-d-glucopyranoside and farrerol, were isolated from the leaves of Cordyline fruticosa. Their structures were elucidated by spectroscopic techniques (1H NMR, 13C NMR, HSQC, 1H- 1H COSY, HMBC, TOCSY, NOESY), mass spectrometry (HRESIMS, Tandem MS-MS), chemical methods and by comparison with published data. Compounds 1 and 2 showed moderate cytotoxic activity against MDA-MB 231 human breast adenocarcinoma cell line, HCT 116 human colon carcinoma cell line, and A375 human malignant melanoma cell line, while compound 3 was not active. Compound 2 also showed a moderate antibacterial activity against the Gram-positive Enterococcus faecalis.
- Fouedjou, Romuald T.,Teponno, Rémy B.,Quassinti, Luana,Bramucci, Massimo,Petrelli, Dezemona,Vitali, Luca A.,Fiorini, Dennis,Tapondjou, Léon A.,Barboni, Luciano
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- The Arabidopsis At1g45130 and At3g52840 genes encode β-galactosidases with activity toward cell wall polysaccharides
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The Arabidopsis genes At1g45130 and At3g52840 encode the β-galactosidase isozymes Gal-5 and Gal-2 that belong to Glycosyl Hydrolase Family 35 (GH 35). The two enzymes share 60% sequence identity with each other and 38-81% with other plant β-galactosidases that are reported to be involved in cell wall modification. We studied organ-specific expression of the two isozymes. According to our western blot analysis using peptide-specific antibodies, Gal-5 and Gal-2 are most highly expressed in stem and rosette leaves. We show by dot-immunoblotting that Gal-5 and Gal-2 are associated with the cell wall in Arabidopsis. We also report expression of the recombinant enzymes in P. pastoris and describe their substrate specificities. Both enzymes hydrolyze the synthetic substrate para-nitrophenyl-β-d-galactopyranoside and display optimal enzyme activity between pH 4.0 and 4.5, similar to the pH optimum reported for other well-characterized plant β-galactosidases. Both Gal-5 and Gal-2 show a broad specificity for the aglycone moiety and a strict specificity for the glycone moiety in that they prefer galactose and its 6-deoxy analogue, fucose. Both enzymes cleave β-(1, 4) and β-(1, 3) linkages in galacto-oligosaccharides and hydrolyze the pectic fraction of Arabidopsis cell wall. These findings suggest that Gal-5 and Gal-2 could be involved in the modification of cell wall polysaccharides.
- Gantulga, Dashzeveg,Turan, Yusuf,Bevan, David R.,Esen, Asim
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- Three new triterpenoid saponins from Albizia julibrissin
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Three new triterpenoid saponins, julibrosides A5–A7 (1–3), together with five known saponins (4–8), were isolated from the stem bark of Albizia julibrissin. Their structures were elucidated on the basis of extensive spectroscopic data analysis of MS, 1D and 2D NMR, and chemical methods. Compounds 7 and 8 were isolated from the genus Albizia for the first time. The new compounds showed no cytotoxicity and anti-inflammatory activity.
- Wang, Xu-Da,Han, Qing-Hua,Zhang, Jun,Zhang, Qing-Ying,Tu, Peng-Fei,Liang, Hong
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- Triterpenoid saponins from Albizia lebbeck (L.) Benth and their inhibitory effect on the survival of high grade human brain tumor cells
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As part of our search of new bioactive triterpenoid saponins from Cameroonian Mimosaceae plants, phytochemical investigation of the roots of Albizia lebbeck led to the isolation of two new oleanane-type saponins, named lebbeckosides A-B (1-2). Their structures were established on the basis of extensive 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC, and HMBC) and HRESIMS studies, and by chemical evidence. Compounds 1-2 were evaluated for their inhibitory effect on the metabolism of high grade human brain tumor cells, the human glioblastoma U-87 MG cell lines and the glioblastoma stem-like TG1 cells isolated from a patient tumor, and known to be particularly resistant to standard therapies. The isolated saponins showed significant cytotoxic activity against U-87 MG and TG1 cancer cells with IC50 values of 3.46 μM and 1.36 μM for 1, and 2.10 μM and 2.24 μM for 2, respectively.
- Noté, Olivier Placide,Jihu, Dong,Antheaume, Cyril,Zeniou, Maria,Pegnyemb, Dieudonné Emmanuel,Guillaume, Dominique,Chneiwess, Hervé,Kilhoffer, Marie Claude,Lobstein, Annelise
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- A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential
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The novel natural low-molecular-mass polysaccharide (SLWPP-3) from pumpkin (Cucurbia moschata) was separated from the waste supernatant after macromolecular polysaccharide production and purified using a DEAE cellulose-52 column and gel-filtration chromatography. Chemical and instrumental studies revealed that SLWPP-3 with a molecular mass of 3.5 kDa was composed of rhamnose, glucose, arabinose, galactose and uronic acid with a weight ratio of 1: 1: 4: 6: 15, and primarily contained →3,6)-β-D-Galp-(1→, →4)-α-GalpA-(1→(OMe), →4)-α-GalpA-(1→, →2,4)-α-D-Rhap-(1→, →3)-β-D-Galp-(1→, →4)-α-D-Glcp, and →4)-β-D-Galp residues in the backbone. The branch chain passes were connected to the main chain through the O-4 atom of glucose and O-3 atom of arabinose. Physiologically, the ability of SLWPP-3 to inhibit carbohydrate-digesting enzymes and DPPH and ABTS radicals, as well as protect pancreatic β cells from oxidative damage by decreasing MDA levels and increasing SOD activities, was confirmed. The findings elucidated the structural types of pumpkin polysaccharides and revealed a potential adjuvant natural product with hypoglycemic effects.
- Huang, Linlin,Li, Fei,Li, Quanhong,Liang, Li,Wei, Yunlu,Yu, Guoyong
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- Phytochemical Investigation of the Roots of Ipomoea asarifolia and Antiproliferative Activity of the Isolated Compounds against Multiple Myeloma Cells
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Ipomoea asarifolia is a herbaceous plant belonging to the family Convolvulaceae and is native to tropical regions of Africa, America, and Asia. A dichloromethane root extract showed antiproliferative activity against multiple myeloma cells (RPMI 8226). The phytochemical investigation led to the isolation of 15 compounds. Compounds 1–4, named (4S,8S)-1-(furan-3-yl)-9-hydroxy-4,8-dimethylnonane-1,6-dione, isoferulic acid hexadecyl ester, caffeic acid hexadecyl ester, and asarifolin I, respectively, are described for the first time. The structures of these molecules were established from their NMR, UV, IR spectroscopic, and MS data. 4-Hydroxycinnamic acid hexadecyl ester (5), 4-hydroxycinnamic acid octadecyl ester (6), 4-hydroxycinnamic acid eicosyl ester (7), caffeic acid octadecyl ester (8), pescapreins III, IV, XXI, XXIII, XXV, and XXVI (9–14), and stoloniferin III (15) were also isolated. All compounds were tested against a multiple myeloma cell line (RPMI 8226). When their IC50 value was lower than 10 μM, the compounds were also tested against two other multiple myeloma cell lines, MM.1S and MM.1R. Compound 3 was the most potent, with an IC50 value of 3.0 μM against RPMI 8226 cells.
- Christen, Philippe,Cuendet, Muriel,Imeri, Deniza,Karimou, Soumana,Quirós-Guerrero, Luis,Saraux, Noémie
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- Novel polysaccharide from Chaenomeles speciosa seeds: Structural characterization, α-amylase and α-glucosidase inhibitory activity evaluation
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Purification and structural characterization of a novel polysaccharide fraction from Chaenomeles speciosa seeds were investigated. After hot water extraction and ethanol precipitation, the crude polysaccharide was sequentially purified with Cellulose DEAE-52 and gel-filtration chromatography, and a highly purified polysaccharide fraction (F3) was obtained. The structure of F3 was characterized by high-performance gel permeation chromatography (HPGPC), high performance liquid chromatography (HPLC), ultraviolet-visible (UV), Fourier transform infrared (FT-IR) and nuclear magnetic resonance (NMR) spectrum, together with methylation, scanning electron microscopy (SEM), atomic force microscope (AFM), and Congo-red test analysis. The results indicated that F3 was a homogeneous polysaccharide fraction with a molecular weight of 8.65 × 106 Da, and it was composed of Rha, GlcA, Gal, and Ara in a molar ratio of 6.34:5.73:47.14:40.13. The backbone of F3 was consisted of →3,6)-Galp-(1→, and the side chains of F3 were composed of Araf-(1→, →4)-GlcpA-(1→, →4)-Galp-(1→ and →3)-Rhap-(1→. The hypoglycemic assays demonstrated F3 had good α-amylase and α-glucosidase inhibition activities, and their IC50 values were 6.24 mg/mL and 4.59 mg/mL respectively. Thus, the polysaccharide from Chaenomeles speciose could be applied as a potential natural source in retarding postprandial hyperglycemia effects.
- Cheng, Jiang,Deng, Yejun,Huang, Lixin,Liu, Lujie,Wang, Xiang,Xie, Pujun,Zhang, Caihong
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p. 755 - 766
(2020/03/18)
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- Novel steroidal glycosides from the whole plants of helleborus foetidus
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Phytochemical analysis of the whole Helleborus foetidus plants identified 28 steroidal glycosides (1-28), including 20 novel spirostanol glycosides (1-20) and a novel furostanol glycoside (21). The structures of the newly identified compounds were elucidated by two-dimensional NMR spectroscopy and hydrolytic cleavage. Compounds 12, 13, and 15 were determined to be spirostanol trisdesmosides bearing sugar moieties at the C-1, -21, and -24 hydroxy groups of the aglycone unit. The isolated compounds were subsequently evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung carcinoma cells. In particular, 7 showed cytotoxic activity against the HL-60 and A549 cells, with IC50 values of 5.9 and 6.6μM, respectively, whereas 19 was selectively cytotoxic to A549 cells with an IC50 value of 5.5μM.
- Iguchi, Tomoki,Uchida, Yuka,Takano, Shingo,Yokosuka, Akihito,Mimaki, Yoshihiro
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p. 273 - 287
(2020/11/26)
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- Structural investigation and comparative cytotoxic activity of water-soluble polysaccharides from fruit bodies of the medicinal fungus quinine conk
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The structures and cytotoxic activities of water-soluble polysaccharides were investigated to search for biologically active polysaccharides from the fruit bodies of quinine conks (Fomitopsis officinalis). The decoctions of this medical fungus are actively used in folk medicine in many countries and traditional Chinese medicine. From the fungal extract we prepared, only branched β-glucan had cytotoxic activity among all the water-soluble polysaccharides. This glucan is characterized by a regular structure. Its backbone is formed by 1,3-linked β-D-Glcp residues, of which every third residue is substituted at O-6 by a single β-D-Glcp residue. It has a triple helix conformation according to the data obtained from a colorimetric assay with Congo red dye and is characterized by a high-weight average molar mass (Mw > 800 kDa). β-Glucan possessed cytotoxic activity against HeLa cells (IC50 = 318 ± 47 μg/mL) and induced the formation of apoptotic bodies around most cancer cells at a concentration of 200 μg/mL. It should be noted that extraction with boiling water, which is usually used to obtain extracts and decoctions, is unable to isolate active β-glucan. Active β-glucan can be obtained in an individual state by cold alkali extraction after dehydration of the fruit bodies and removal of the components extractable by boiling water.
- Golovchenko, Victoria V.,Naranmandakh, Shinen,Ganbaatar, Jamsranjav,Prilepskii, Artur Yu.,Burygin, Gennady L.,Chizhov, Alexander O.,Shashkov, Alexander S.
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- Lebbeckoside C, a new triterpenoid saponin from the stem barks of Albizia lebbeck inhibits the growth of human glioblastoma cells
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One new acacic acid-type saponin, named lebbeckoside C (1), was isolated from the stem barks of Albizia lebbeck. Its structure was established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as 3-O-[β-d-xylopyranosyl-(l→2)-β-d-fucopyranosyl-(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl]-21-O-{(2E,6S)-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-β-d-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28 O-[β-d-quinovopyranosyl-(l→3)-[α-l-arabinofuranosyl-(l→4)]-α-l-rhamnopyranosyl-(l→2)-β-d-glucopyranosyl] ester. The isolated saponin (1) displayed significant cytotoxic activity against the human glioblastoma cell line U-87 MG and TG1 stem-like glioma cells isolated from a patient tumor with IC50 values of 1.69 and 1.44?μM, respectively.
- Noté, Olivier Placide,Ngo Mbing, Joséphine,Kilhoffer, Marie-Claude,Pegnyemb, Dieudonné Emmanuel,Lobstein, Annelise
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p. 2292 - 2299
(2018/02/26)
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- Antiangiogenic phenylpropanoid glycosides from Gynura cusimbua
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A new phenylpropanoid glycoside, named α-L-rhamnopyranosyl-(1?2)-β-D-[4″-(8E)-7-(3,4-dihydroxyphenyl)-8-propenoate, 1″-O-(7S)-7-(3,4-dihydroxyphenyl)-7-methoxy-ethyl]-glucopyranoside (1), together with nine known compounds (2–10) were isolated from the active fraction (n-Butanol fraction) of Gynura cusimbua for the first time. The known compounds (2–10) were identified as phenylpropanoid glycosides on the basis of extensive spectral data and references. The antiangiogenic activities of compounds (1–10) were evaluated by MTT assay on HUVECs and wild-type zebrafish in vivo model assay. As a result, compounds 1, 6, 7, 8 and 10 exhibited certain antiangiogenic activities.
- Ma, Qinge,Wei, Rongrui,Zhou, Bin,Sang, Zhipei,Liu, Wenmin,Cao, Zhongling
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p. 457 - 463
(2017/10/26)
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- Effect of polyphenols from Vicia faba L on lipase activity and melanogenesis
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Two new flavonoid glycosides, kaempferol 3-O-α-L-rhamnopyranosyl (1→6) (3′′-acetyl)-β-D-galactopyranoside 1 and kaempferol 3-O-α-L-arabinopyranosyl-5-O-α-L-rhamnopyranoside 2, along with six known ones 3–8 were isolated from the flowers of Vicia faba L. (Fabaceae). Methanol extract and the isolated compounds were tested against lipase and melanogenesis inhibition activities and resulted in that compound 2 showed 53 and 77% lipase inhibition activity in concentrations of 400 and 800?μg/mL, respectively. For melanogenesis, compounds 2, 3 and 4 exhibited potent melanogenesis inhibition activity where the melanin content in melanoma cells was decreased to be about 57.5, 56 and 61%, respectively, with no obvious melanocytotoxicity. The rest of compounds showed weak to moderate activity. The results of melanogenesis inhibition activity of this study suggested the potential use of Vicia faba flowers as a skin-whitening agent and reveal the flowers to be a rich source of important phytochemicals with antilipase and melanogenesis inhibitory activity.
- Allam, Ahmed E.,Nafady, Alaa M.,Nakagawa, Toshinori,Takemoto, Naomichi,Shimizu, Kuniyoshi
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p. 1920 - 1925
(2017/10/06)
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- Structure and anticancer activity of native and modified polysaccharides from brown alga Dictyota dichotoma
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The laminaran DdL and fucoidan DdF were obtained from the brown alga Dictyota dichotoma. DdF was a sulfated (28.9%) and acetylated heteropolysaccharide containing fucose, galactose, mannose and glucose (57.9, 20.4, 12.4 and 9.2 mol%, respectively). DdL was a 1,3;1,6-β-D-glucan with the main chain built from 1,3-linked glucose residues and single glucose residue in branches at C6 (one branch on three glucose residues of the main chain). Sulfated (43.7%) laminaran DdLs was obtained from DdL by sulfation. It was determined that sulfates occur at C2, C4 and C6 of glucose residues. The anticancer effect of DdF, DdL, and DdLs (200 μg/mL) was studied in vitro on colon cancer cells HCT-116, HT-29, and DLD-1. The effect of polysaccharides (40 μg/mL) on colony formation of DLD-1 cancer cells after irradiation (4 Gy) was investigated first. All polysaccharides showed a synergistic effect with X-ray irradiation against cancer cells, decreasing the amount and size of cancer cells colonies.
- Usoltseva, Roza V.,Shevchenko, Natalia M.,Malyarenko, Olesya S.,Ishina, Irina A.,Ivannikova, Svetlana I.,Ermakova, Svetlana P.
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- New dammarane triterpenoid saponins from the leaves of Cyclocarya paliurus
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Three new dammarane triterpenoid saponins, cyclocariosides O-Q (1–3), were isolated from the ethanolic extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic methods.
- Wang, Yi-Rui,Cui, Bao-Song,Han, Shao-Wei,Li, Shuai
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- Albidosides H and I, two new triterpene saponins from the barks of Acacia albida Del. (Mimosaceae)
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Two new triterpene saponins, albidosides H (1) and I (2), along with the three known saponins were isolated from the barks of Acacia albida. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and mass spectrometry. Albidosid
- Tchoukoua, Abdou,Kuiate Tabopda, Turibio,Konga Simo, Ingrid,Uesugi, Shota,Ohno, Misa,Kimura, Ken-ichi,Kwon, Eunsang,Momma, Hiroyuki,Shiono, Yoshihito,Ngadjui, Bonaventure Tchaleu
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p. 924 - 932
(2018/02/15)
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- Optimization of ultrasound-assisted extraction of okra (Abelmoschus esculentus (L.) Moench) polysaccharides based on response surface methodology and antioxidant activity
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This study determined the optimal conditions for ultrasound-assisted extraction of a water-soluble polysaccharide, Raw Okra Polysaccharide, from the fruit of okra using response surface methodology. The optimal extraction temperature, extraction time and ultrasonic power were 59 °C, 30 min and 522 W, respectively, giving a yield of 10.35 ± 0.11%. ROP was further isolated, lyophilized and purified using a DEAE-Sepharose Fast Flow column and Sepharose CL-6B column, revealing three elution peaks subsequently designated ROP ?1, ?2, and ?3, respectively. Of these, ROP-2 showed the highest yield, and was therefore selected for physicochemical analysis and evaluation of antioxidant activity. Gas chromatography, fourier transform infrared spectroscopy, and high-performance liquid chromatography were used to characterize the primary structural features and molecular weight, revealing that ROP-2 is composed of glucose, mannose, galactose, arabinose, xylose, fructose, and rhamnose (molar percentages: 28.8, 12.5, 13.1, 15.9, 9.2, 13.7, and 6.8%, respectively) and has an average molecular weight of 1.92 × 105 Da. A superoxide radical scavenging assay and DPPH radical scavenging assay further revealed the significant in vitro antioxidant activity of ROP-2. These findings present an effective technique for extraction of the natural antioxidant ROP-2, warranting further analysis of its potential application in the food industry.
- Wang, Kunli,Li, Mo,Wen, Xin,Chen, Xiaosong,He, Zhengyu,Ni, Yuanying
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p. 1056 - 1063
(2018/04/12)
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- Steroids from herbs of Reineckia carnea and their anticomplement activities
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A new polyhydroxylated pregnane, named lβ,2β,3β,4β,5β,6β-hexolhydroxy-pregn-16-en-20-one (1), along with nine known (2–10) steroidal saponins were isolated from the whole plant of Reineckia carnea.?Structure elucidations?of all compounds were established by interpretation of their NMR spectral data, HR-ESI-MS and comparing with literatures. In addition, these compounds were evaluated with anticomplement activity. The result showed that compound 1 exhibited anticomplement effects with the CH50 values of 0.043?mg/mL, but saponins (2–10) showed no inhibition. Interestingly, hydrolysis of steroidal saponins (2–10) resulted in its aglycones (2a–10a) correspondingly which showed anticomplement activity with the CH50 values of 0.049–0.156?mg/mL.
- Xu, Xu,Wu, Bei,Zhan, Yanzhi,Huang, Wenping,Yang, Shilin,Wen, Quan,Feng, Yulin
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supporting information
p. 1 - 7
(2018/02/06)
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- Hepta-, hexa-, penta-, tetra-, and trisaccharide resin glycosides from three species of Ipomoea and their antiproliferative activity on two glioma cell lines
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Six new partially acylated resin glycosides were isolated from convolvulin of Ipomoea purga, Ipomoea stans, and Ipomoea murucoides (Convolvulaceae). The structures of compounds 1–6 were elucidated by a combination of NMR spectroscopy and mass spectrometry. The structure of jalapinoside B (1) consists of a hexasaccharide core bonded to an 11-hydroxytetradecanoic (convolvulinic) acid forming a macrolactone acylated by a 2-methylbutanoyl, a 3-hydroxy-2-methylbutanoyl, and a quamoclinic acid B units. Purginoic acid A (2) contains a hexasaccharide core bonded to a convolvulinic acid acylated by a 3-hydroxy-2-methylbutanoyl unit. Stansin A (4) is an ester-type heterodimer, and consists of two stansoic acid A (3) units, acylated by 2-methylbutanoic and 3-hydroxy-2-methylbutanoic acids. The site of lactonization was located at C-3 of Rhamnose, and the position for the ester linkage of the monomeric unit B on the macrolactone unit A was established as C-4 of the terminal rhamnose. Compounds 5 and 6 are glycosidic acids. Murucinic acid II (5) is composed of a pentasaccharide core bonded to an 11-hydroxyhexadecanoic (jalapinolic) acid, acylated by an acetyl unit. Stansinic acid I (6) is a tetrasaccharide core bonded to a jalapinolic acid, acylated by 2-methylbutanoyl and 3-hydroxy-2-methylbutanoyl units. Preliminary testing showed the cytotoxicity of compounds 1–6 toward OVCAR and UISO-SQC-1 cancer cell lines. In addition, compound 1 showed an antiproliferative activity on glioma C6 and RG2 tumor cell lines. Copyright
- León-Rivera, Ismael,del Río-Portilla, Federico,Enríquez, Raúl G.,Rangel-López, Edgar,Villeda, Juana,Rios, María Yolanda,Navarrete-Vázquez, Gabriel,Hurtado-Días, Israel,Guzmán-Valdivieso, Ulises,Nú?ez-Urquiza, Verónica,Escobedo-Martínez, Carolina
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p. 214 - 223
(2017/03/05)
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- New Cytotoxic Triterpenoid Saponins from the Roots of Albizia gummifera (J.F.Gmel.) C.A.Sm.
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As part of our search for new bioactive saponins from Cameroonian medicinal plants, two new oleanane-type saponins, named gummiferaosides D and E (1 and 2), along with one known saponin, julibroside J8 (3), were isolated from the roots of Albizia gummifera. Their structures were established on the basis of extensive 1D- and 2D-NMR (1H- and 13C-NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY, and HMBC) and HR-ESI-MS studies, and by chemical evidence. The apoptotic effect of saponins 1?–?3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1?–?3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner.
- Simo, Line Made,Noté, Olivier Placide,Mbing, Joséphine Ngo,Aouazou, Sarah Ali,Guillaume, Dominique,Muller, Christian Dominique,Pegnyemb, Dieudonné Emmanuel,Lobstein, Annelise
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- Triterpenoid saponins with anti-inflammatory activities from Ilex pubescens roots
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Seven triterpenoid saponins, named ilexsaponin I–O, along with twelve known ones, were isolated from the roots of Ilex pubescens. The structures of all compounds were elucidated by use of extensive spectroscopic methods (IR, HR-ESI-MS, and 1D and 2D NMR).
- Wu, Peng,Gao, Hui,Liu, Jian-Xin,Liu, Liang,Zhou, Hua,Liu, Zhong-Qiu
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p. 122 - 132
(2016/12/23)
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- Jalapinoside II, a bisdesmoside resin glycoside, and related glycosidic acids from the officinal jalap root (Ipomoea purga)
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Jalapinoside II, a macrocyclic bidesmoside resin glycoside with purgic acid C as its oligosaccharide core, was isolated by recycle preparative-scale HPLC from the MeOH-soluble extract of Ipomoea purga (Convolvulaceae), the officinal jalap root (“Rhizoma Jalapae”). This study also reports the complete NMR data assignment for purgic acid C and the structural elucidation of purgic acid D, both glycosidic acids were isolated, in conjunction with previously known purgic acids A and B, under saponification of the MeOH-soluble resin glycosides. HPLC and 13C NMR profiles were used as analytical tools for the authentication of the commercialized Mexican scammony resin. Reversal factor of multidrug resistance by the non-cytotoxic jalapinoside II was evaluated in vinblastine-resistant human breast carcinoma cells (RFMCF-7/Vin+ > 1906).
- Bautista, Elihú,Fragoso-Serrano, Mabel,Pereda-Miranda, Rogelio
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- New pregnane and phenolic glycosides from Solenostemma argel
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From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1–3) with two known ones and a new phenolic glycoside (4) have been isolated. Their structures were established by extensive 1D – and 2D NMR and mass spectroscopic analysis. The cytotoxicity of all compounds was evaluated against two human tumor cell lines (SW 480, MCF-7), but none of them was active in the concentration range 0.9–59.0?μM. Compounds 2 and the known argeloside F at non toxic concentrations for the PBMCs (27.3?μM and 27.6?μM, respectively) significantly decreased the Il-1β production by LPS-stimulated PBMCs. All isolated compounds showed a significant antioxidant potential with ORAC values in the concentration range 3481–9617?μmol?eq. Trolox/100?g.
- Ounaissia, Karima,Pertuit, David,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Tanaka, Chiaki,Delemasure, Stéphanie,Dutartre, Patrick,Smati, Dalila,Lacaille-Dubois, Marie-Aleth
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- Resin Glycosides from Ipomoea alba Seeds as Potential Chemosensitizers in Breast Carcinoma Cells
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Multidrug resistance is the expression of one or more efflux pumps, such as P-glycoprotein, and is a major obstacle in cancer therapy. The use of new potent and noncytotoxic efflux pump modulators, coadministered with antineoplastic agents, is an alternative approach for increasing the success rate of therapy regimes with different drug combinations. This report describes the isolation and structure elucidation of six new resin glycosides from moon vine seeds (Ipomoea alba) as potential mammalian multidrug-resistance-modifying agents. Albinosides IV-IX (1-6), along with the known albinosides I-III (7-9), were purified from the CHCl3-soluble extract. Degradative chemical reactions in combination with NMR spectroscopy and mass spectrometry were used for their structural elucidation. Four new glycosidic acids, albinosinic acids D-G (10-13), were released by saponification of natural products 3-6. They were characterized as tetrasaccharides of either convolvulinolic (11S-hydroxytetradecanoic) or jalapinolic (11S-hydroxyhexadecanoic) acids. The potentiation of vinblastine susceptibility in multidrug-resistant human breast carcinoma cells of albinosides 1-6 was evaluated by modulation assays. The noncytotoxic albinosides VII (4) and VIII (5), at a concentration of 25 μg/mL, exerted the strongest potentiation of vinblastine susceptibility, with a reversal factor (RFMCF-7/Vin+) of 201- and >2517-fold, respectively.
- Cruz-Morales, Sara,Casta?eda-Gómez, Jhon,Rosas-Ramírez, Daniel,Fragoso-Serrano, Mabel,Figueroa-González, Gabriela,Lorence, Argelia,Pereda-Miranda, Rogelio
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p. 3093 - 3104
(2017/01/03)
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- Oleanane-type triterpenoid saponins from Silene armeria
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Twelve triterpenoid saponins, including seven compounds (i.e., armerosides A–G) hitherto unknown, were isolated from whole plants of Silene armeria. Their structures were established based on extensive spectroscopic analyses and chemical methods. From a biosynthetic perspective, C-23 oxidation of the sapogenin appears to be a key factor in the glycosylation pathway.
- Takahashi, Nobuyuki,Li, Wei,Koike, Kazuo
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- Molecular structure, chemical properties and biological activities of Pinto bean pod polysaccharide
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Pinto bean pod polysaccharide (PBPP) was successfully extracted with yield of 38.5 g/100 g and the PBPP gave total carbohydrate and uronic acid contents of 286.2 mg maltose equivalent/g and 374.3 mg Gal/g, respectively. The Mw of PBPP was 270.6 kDa with intrinsic viscosity of 0.262 dm3/g, which composed of mannose (2.5%), galacturonic acid (15.0%), rhamnose (4.0%), glucose (9.0%), galactose (62.2%), xylose (2.9%) and arabinose (4.3%) with trace amount of ribose and fucose. The result suggested that PBPP has a spherical conformation with a highly branched structure. Fourier Transform Infrared analysis showed that PBPP has a similar structure as commercial pectin with an esterification degree of 59.9%, whereas scanning electron microscopy study showed that the crude polysaccharide formed a thin layer of film that was made of multiple micro strands of fibre. PBPP exhibited substantial free radical scavenging activity (7.7%), metal reducing capability (2.04 mmol/dm3) and α-amylase inhibitory activity (97.6%) at a total amount of 1 mg. PBPP also exhibited high water- and oil-holding capacities (3.6 g/g and 2.8 g/g, respectively). At a low concentration, PBPP exhibited emulsifying activity of 39.6% with stability of 38.6%. Apart from that, PBPP was able to show thickening capability at low concentration (0.005 kg/dm3).
- Kamarudin, Fazlina,Gan, Chee-Yuen
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p. 280 - 287
(2016/04/19)
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- Two pentasaccharide resin glycosides from Argyreia acuta
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Two new compounds of acutacosides 1 and 2, pentasaccharide resin glycosides were isolated from the aerial parts of Argyreia acuta. The core of the two compounds was operculinic acid A, and they were esterfied at the same position, just one substituent group was linked at C-2 of Rha. The absolute configuration of the aglycone in the two compounds was established by Mosher's method, which was (11S)-hydroxyhexadecanoic acid (jalapinolic acid). Their structures were established by a combination of spectroscopic and chemical methods.
- Yin, Yong-Qin,Pan, Jie-Tao,Yu, Bang-Wei,Cui, Hong-Hua,Yan, You-Shao,Chen, Yan-Fen
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- Antioxidant Flavonols and Phenolic Compounds from Atraphaxis frutescens and Their Inhibitory Activities against Insect Phenoloxidase and Mushroom Tyrosinase
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Chemical investigation of the aerial parts of Atraphaxis frutescens resulted in the isolation of five 7-methoxyflavonols with pyrogallol B-ring moieties (1-5), a fisetinidol glucoside (13), and a benzyl glycoside (18), together with 26 known compounds including flavonoids, phenylpropanoid amides, anthraquinone glycosides, lignans, and a benzyl derivative. The principal chemical structural feature of the isolated compounds was either a pyrogallol or catechol B-ring moiety, and they showed potent 1,1-diphenyl-2-picrylhydrazyl radical scavenging activities. To assess the effects of these antioxidants on biological enzymes, their inhibitory effects against an insect phenoloxidase and a mushroom tyrosinase were evaluated. This study indicated that insect phenoloxidase was inhibited by phenylpropanoid amides and that mushroom tyrosinase was inhibited by the characteristic 7-methoxyflavonol 3-O-rhamnopyranosides.
- Odonbayar, Batsukh,Murata, Toshihiro,Batkhuu, Javzan,Yasunaga, Kosho,Goto, Rina,Sasaki, Kenroh
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p. 3065 - 3071
(2017/01/03)
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- A new steroidal saponin, furotrilliumoside from Trillium tschonoskii inhibits lipopolysaccharide-induced inflammation in Raw264.7 cells by targeting PI3K/Akt, MARK and Nrf2/HO-1 pathways
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A new steroidal saponin, furotrilliumoside (FT) was isolated from the roots and rhizomes of Trillium tschonoskii Maxim. Its structure was elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. FT showed superior activity of inhibiting NO production of RAW264.7 cells induced by lipopolysaccharide (LPS) in the preliminary biological screening. In order to develop novel therapeutic drug for acute and chronic inflammatory disorders, the anti-inflammatory activity and underlying mechanism of FT were investigated in LPS-induced RAW264.7 cells. The results showed that FT could reduce LPS-induced expression of inducible nitric oxide synthase (iNOS) and then resulted in the decrement of NO production. More meaningful, FT could down-regulate the expression of cyclooxygenase-2 (COX-2) and decrease the expressions of pro-inflammatory cytokines, tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6) and interleukin-1β (IL-1β), in both gene and protein levels. In mechanism study, FT blocked the LPS-induced upregulation of phosphorylated phosphoinositide-3-kinase and Akt (PI3K/Akt). Furthermore, FT inhibited the translocation of nuclear factor-kappa B (NF-κB) through the prevention of inhibitory factor kappa B alpha (IκBα) phosphorylation and degradation and also suppressed the mitogen-activated protein kinases (MAPK) signaling pathway in LPS-stimulated RAW264.7 macrophages. In addition, FT upregulated heme oxygenase-1 (HO-1) expression via nuclear translocation of nuclear factor E2-related factor 2 (Nrf2). Taken together, FT might act as a natural agent to treat some inflammatory diseases by targeting PI3K/Akt, MARK and Nrf2/HO-1 pathways.
- Yan, Ting,Yu, Xiangyong,Sun, Xianduo,Meng, Dali,Jia, Jing-ming
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- Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d -Gulose, 6-Deoxy- d -gulose, l -Glucose, 6-Deoxy- l -glucose, and Related Sugars
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Ease of separation of petrol-soluble acetonides derived from the triacetonide of methyl glucoheptonate allows scalable syntheses of rare sugars containing the l-gluco or d-gulo structural motif with any oxidation level at the C6 or C1 position of the hexose, usually without chromatography: meso-d-glycero-d-guloheptitol available in two steps is an ideal entry point for the study of the biotechnological production of heptoses.
- Liu, Zilei,Yoshihara, Akihide,Jenkinson, Sarah F.,Wormald, Mark R.,Estévez, Ramón J.,Fleet, George W.J.,Izumori, Ken
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supporting information
p. 4112 - 4115
(2016/08/30)
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- Antitumor and immunomodulatory activities of a water-soluble polysaccharide from Chaenomeles speciosa
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Abstract In this study, a water-soluble polysaccharide (CSP) was successfully purified from Chaenomeles speciosa by DEAE-Sepharose and Sephadex G-100 column chromatography. CSP had a weight-average molecular weight of about 6.3 × 104 Da and was composed of glucose (Glc), galactose (Gal), rhamnose (Rha) and arabinose (Ara) with a relative molar ratio of 4.6:1.3:0.8:0.5. CSP could not only inhibit the growth of S180 tumor transplanted in mice, but also increase the relative spleen index and body weight of tumor bearing mice. Moreover, concanavalin A (ConA) and lipopolysaccharide (LPS) induced splenocyte proliferation and peritoneal macrophage phagocytosis were also enhanced after CSP administration. Furthermore, CSP treatment could improve delayed type hypersensitivity (DTH) and promote the secretion of IL-2, TNF-α and IFN-γ in serum. The overall findings suggest that the antitumor effect of CSP is might be associated with its potent immunostimulatory activity.
- Xie, Xianfei,Zou, Guolin,Li, Chenghai
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p. 323 - 329
(2015/07/15)
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- Characterization and biological activities of a novel polysaccharide isolated from raspberry (Rubus idaeus L.) fruits
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Abstract A water-soluble polysaccharide namely RCP-II from raspberry fruits was obtained by complex enzyme method followed by successive purification using macroporous resin D4020 and Sephadex G-100 columns. RCP-II was an acidic heteropolysaccharide and the characteristic structure of polysaccharide was determined. The carbohydrate of RCP-II was composed with galacturonic acid, rhamnose, arabinose, xylose, glucose and galactose in a molar ratio of 1.00:0.55:1.19:0.52:0.44:1.90 and the average molecular weight was estimated to be 4013 Da, based on dextran standards. RCP-II presented high scavenging activity toward DPPH?, HO?, O2?- in a concentration-dependent manner. The determination of the inhibitory activity on protein glycation showed that in 14 days of incubation the inhibitory ability of RCP-II was more effective on the development of non-enzymatic glycation reaction at early phase than that at the following two phases.
- Yu, Zeyuan,Liu, Lu,Xu, Yaqin,Wang, Libo,Teng, Xin,Li, Xingguo,Dai, Jing
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p. 180 - 186
(2015/07/15)
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- A new flavonol triglycoside derived from Anoectochilus elwesii on stimulating glucose uptake in insulin-induced human HepG2 cells
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A novel flavonol triglycoside (4), isorhamnetin-3-O-β-d-glucopyranosyl (1→2)-α-l-rhamnopyranosyl (1→6)-β-d-glucopyranoside, named elwesoside A, together with six known flavonols (1-3, 5-7) was isolated from Anoectochilus elwesii (Clarke ex Hook. f.) King et Pantl. and its structure was elucidated by extensive spectroscopic methods and comparison with the literature data. All compounds were first reported in this plant and two of them (4 and 5) were the first examples of flavonol triglycosides isolated from Anoectochilus genus. The effects of 1-7 were evaluated on insulin-treated human HepG2 cells under high glucose conditions for stimulating glucose uptake activities. The novel compound (4) displayed highly potent dose-dependent effect on the stimulation of glucose uptake in insulin-resistant human HepG2 cells.
- Cai, Jinyan,Zhao, Lin,Zhu, En
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p. 1414 - 1418
(2015/03/05)
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- Purification, characterization and antitumor activity of polysaccharides extracted from Phellinus igniarius mycelia
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Abstract Water-soluble intracellular polysaccharides (IPS) were extracted from cultured mycelia of Phellinus igniarius. The IPS were purified by ethanol fractional precipitation, ion-exchange and size exclusion chromatography in that order. Homogeneous polysaccharide IPSW-1, IPSW-2, IPSW-3, and IPSW-4 were obtained, which molecular characteristics were examined using multiangle laser-light scattering and refractive index detector system. The average molecular weights of them were 34.1, 17.7, 15.1, 21.7 kDa, respectively. GC analysis indicated that IPSW-1, IPSW-2 and IPSW-3 all only contained glucose, while IPSW-4 was composed of rhamnose, xylose, mannose, glucose and galactose in a molar ratio of 1.29:1.21:1:43.86:1.86. UV and IR analysis suggested they belonged to α-type of the pyran group and didn't contain protein. These homogeneous polysaccharides could inhibit the growth of SW480 and HepG2 cells to a certain extent in a dose-dependent manner. So they could be beneficial for the further development of a natural carcinoma preventive agent and functional food.
- Li, Shi-Chao,Yang, Xiao-Ming,Ma, Hai-Le,Yan, Jing-Kun,Guo, Dan-Zhao
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- Simalin A and B: Two new aromatic compounds from the stem bark of Bombax ceiba
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Two new aromatic compounds, simalin A (1) and B (2), along with five known compounds shamiminol (3), (-)-epicatechin-7-O-β-xylopyranoside (4), (-)-catechin-7-O-β-xylopyranoside (5), (+)-isolarisiresinol-9′-O- β-glucopyranoside (6) and (+)-lyoniresinol-9′-O-β- glucopyranoside (7) were isolated from the stem bark of Bombax ceiba. Their structures were elucidated by chemical and spectral methods. Compounds 6 and 7 were isolated for the first time from B. ceiba.
- Joshi, Khem Raj,Devkota, Hari Prasad,Yahara, Shoji
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- Triterpenoid saponins from the roots of two Gypsophila species
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Two triterpenoid saponins with two known ones have been isolated from the roots of Gypsophila arrostii var. nebulosa, and two new ones from the roots of Gypsophila bicolor. Their structures were established by extensive NMR and mass spectroscopic techniqu
- Pertuit, David,Avunduk, Sibel,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Tanaka, Chiaki,Paululat, Thomas,Delemasure, Stéphanie,Dutartre, Patrick,Lacaille-Dubois, Marie-Aleth
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p. 182 - 188
(2014/05/06)
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