- Two new isoflavones from the barks of Dalbergia hancei Benth
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Two new isoflavone compounds, Dalhancei A (1) and Dalhancei B (2), along with a known compound epicatechin (3) were isolated from 80% methanol extract of the barks of Dalbergia hancei Benth. The structures of compounds 1–3 were elucidated by comparison with the literature and physical data analysis, including optical rotation, MS, 1D and 2D NMR spectra. Compounds 1 and 2 showed weak inhibitory activity against tyrosinase at 16.22 mmol/L, with inhibition rates of 42.23 ± 0.18% and 45.68 ± 0.17%, respectively; compound 1 exhibited weak inhibitory activity against α-glucosidase with the inhibition rate of 43.72 ± 0.22% at 5.41 mmol/L, compounds 2 and 3 had better α-glucosidase inhibitory activity than compound 1 with IC50 values of 0.90 ± 0.18 and 0.41 ± 0.17 mmol/L, respectively.
- Ge, Li,He, Rui-Jie,Huang, Yong-Lin,Li, Xiao-Mei,Pang, Nao,Wang, Ya-Feng,Yang, Bing-Yuan,Yang, Ke-Di
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supporting information
(2022/03/27)
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- Structural characterization of phenolic constituents from the rhizome of Imperata cylindrica var. major and their anti-inflammatory activity
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As one of raw materials, the rhizome of Imperata cylindrica var. major (Nees) C.E. Hubb. is used in kinds of preparations curing inflammation related diseases, while its effective substances are not yet clear. In this paper, its chemical constituents and their anti-inflammatory activities were investigated. As results, ten compounds, named as imperphenoside A (1), imperphenols B (2) and C (3), imperphenosides D–F (4–6), and imperlignanosides A–D (7–10), along with previously reported thirty-seven known ones (11–47) were obtained from it. Their structures were ascertained basing on the extensive spectroscopic methods and electronic circular dichroism data analysis. Meanwhile, compounds 4, 11, 12, 24, 27, 31, 32, 37, 43, 45, and 47 exhibited nitric oxide inhibitory effects in concentration dependent at 3, 10, and 30 μM on lipopolysaccharides induced RAW 264.7 cells. Moreover, the western blot analysis indicated that compounds 4, 11, 43, and 47 could restrain the phosphorylation of nuclear factor kappa-B kinase to down-regulate the protein expression of inflammatory cytokines such as inducible nitric oxide synthase, interleukin-6 and tumor necrosis factor-α. In conclusion, they might play the anti-inflammatory effects through regulating NF-κB signaling pathway.
- Cao, Hui-Na,Han, Yu,Hao, Mi-Mi,Jiang, Hong-Yu,Li, Hui-Min,Ruan, Jing-Ya,Wang, Tao,Zhang, Yi,Zhang, Ying,Zhao, Wei
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- The phenolic acids from Oplopanax elatus Nakai stems and their potential photo-damage prevention activity
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25 phenolic acids, including four new isolates, eurylophenosides A–D (1–4) and 21 known ones (5–25) were isolated and identified from the stems of Oplopanax elatus Nakai. Among the known compounds 5–9, 11–13, 16, 18–25 were isolated from the genus for the first time; 17 was first obtained from the plant; and the NMR data of 22 was reported here first. Meanwhile, the UVB-induced photodamage model of HaCaT cells was used to study the prevent-photodamage abilities of compounds 1–2, 4–8, 11–13 and 15–25 with a nontoxic concentration at 50?μM. Moreover, a dose-dependent experiment was conducted for active compounds at the concentration of 10, 25, and 50?μM, respectively. Consequently, pretreatment with compounds 1, 16, 17, 19, 20, 22, 24 and 25 could suppress the cell viability decreasing induced by UVB irradiation in a concentration-dependent manner. These results indicated that phenolic acids were one kind of material basis with prevent-photodamage activity of O. elatus. Graphic abstract: [Figure not available: see fulltext.].
- Han, Yu,Cheng, Dongsheng,Hao, Mimi,Yan, Jiejing,Ruan, Jingya,Han, Lifeng,Zhang, Yi,Wang, Tao
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- Anti-inflammatory active components of the roots of Datura metel
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One new phenolic glycoside, methyl 3,4-dihydroxyphenylacetate-4-O-[2-O-β-D-apisoyl-6-O-(2-hydroxybenzoyl)]-β-D-glucopyranoside (1), together with 10 known compounds (2–11), were isolated from the roots of Datura metel. The structures of these compounds we
- Qin, Ze,Zhang, Jin,Chen, Liang,Liu, Shu-Xiang,Zhao, Hai-Feng,Mao, Hui-Min,Zhang, Hong-Yang,Li, De-Fang
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p. 392 - 398
(2020/03/30)
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- Two new flavonol glycosides from Selaginella tamariscina
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Two new flavonol glycosides 3,5,7-trimethoxyflavone-4'-O-[5'''-O-p-coumaroyl-β-D-apiofuranoyl-(1'''→2'')-β-D-glucopyranoside] (1) and 3,5,7-trimethoxyflavone ?4'-O-β-D-glucopyranoside (2) were isolated from Selaginella tamariscina. The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses and HRESIMS spectrometry. Two compounds were evaluated for cytotoxic activities against A-375, MCF-7, MDA-MB-231 and MDA-MB-468 cell lines by MTT assay. Unfortunately, two compounds displayed no cytotoxic activities.
- Li, Wen-Lan,Nie, Cheng-Dong,Wang, Qi-Xuan,Wen, Jing,Yan, Xin-Jia
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- New Phenolic Glycosides and Lignans from the Roots of Lilium dauricum
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Three new phenolic glycosides, carvacrol-2- O - β -D-apiofuranosyl-(1 → 6)- β -D-glucopyranoside (1), 1-methyl-3-isopropylphenol-4- O - β -D-apiofuranosyl-(1 → 6)- β -D-glucopyranoside (2), p -methoxythymol-5- O - β -D-apiofuranosyl-(1 → 6)- β -D-glucopyranoside (3), and a pair of new 8- O -4′ neolignan enantiomers (5a / 5b), together with 26 known compounds (4, 6 - 30) were isolated from the roots of Lilium dauricum. The structures of the new compounds were elucidated based on extensive spectroscopic and chemical methods, and the absolute configurations of 5a and 5b were established by electronic circular dichroism analysis. Nine compounds (1, 3, 4, 8, 9, 17, 25, 29, and 30) exhibited potent α -glucosidase inhibitory activity with IC 50values ranging from 73.4 μM to 988.2 μM. Besides, compound 19 displayed strong anticomplementary activity (CH 50: 71.6 μM).
- Chen, Dao-Feng,Lu, Yan,Wang, Xiao-Jiang,Xia, Xiao,Zhang, Jiao
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supporting information
(2021/07/17)
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- Phenolic constituents isolated from Senna tora sprouts and their neuroprotective effects against glutamate-induced oxidative stress in HT22 and R28 cells
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The consumption of sprouts has been steadily increasing due to their being an excellent source of nutrition. It is known that the bioactive constituents of legumes can be increased after germination. In this study, the extract from Senna tora sprouts is shown to exhibit improved radical scavenging activities and better neuroprotective effects in HT22 hippocampal neuronal (HT22) and R28 retina precursor (R28) cells than those from seeds due to an increased content of phenolic constituents, especially compounds 1 and 3–6. A phytochemical investigation of S. tora sprouts resulted in the isolation of two new naphthopyrone glycosides (1–2) with 27 previously reported compounds. Their structures were determined via interpreting spectroscopic data. Compounds 1 and 3–6 were found to possess radical scavenging activities and neuroprotective effects against oxidative stress in both neuronal cells. Hence, Senna tora sprouts and their constituents may be developed as natural neuroprotective agents via antioxidative effects.
- Kwon, Jaeyoung,Hwang, Hoseong,Selvaraj, Baskar,Lee, Jung Hwan,Park, Woongbi,Ryu, Seung Mok,Lee, Dongho,Park, Jin-Soo,Kim, Hyoung Seok,Lee, Jae Wook,Jang, Dae Sik,Kwon, Hak Cheol
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- Indole glycosides from calanthe discolor with proliferative activity on human hair follicle dermal papilla cells
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A methanol extract from the underground part of Calanthe discolor Lindl. (Orchidaceae) demonstrated significant proliferative activity on human hair follicle dermal papilla cells (HFDPC, % of control: 120.8±0.2%) at 100μg/mL against HFDPC. Through bioassay-guided separation of the extract, a new indole glycoside named 6′-O-β-D-apiofuranosylindican (1) was isolated along with six known compounds (2–7) including three indole glycosides. The stereostructure of 1 was elucidated based on its spectroscopic properties and chemical characteristics. Among the isolates, 1 (110.0±1.0%), glucoindican (3, 123.9±6.8%), and calanthoside (4, 158.6±7.1%) showed significant proliferative activity at 100μM. Furthermore, the active indole glycosides (1, 3, and 4) upregulated the expression of vascular endothelial growth factor (VEGF) and fibroblast growth factor-7 (FGF-7) mRNA and protein in HFDPC, which could be the mechanism of their proliferative activity.
- Morikawa, Toshio,Manse, Yoshiaki,Luo, Fenglin,Fukui, Haruko,Inoue, Yamato,Kaieda, Tsuyoshi,Ninomiya, Kiyofumi,Muraoka, Osamu,Yoshikawa, Masayuki
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p. 464 - 471
(2021/05/27)
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- Stable Axially Chiral Isomers of Arylnaphthalene Lignan Glycosides with Antiviral Potential Discovered from Justicia procumbens
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Arylnaphthalene lignans (ANLs) were known to have axial chirality due to the biphenyl skeleton with hindered rotation at the single bond. However, the stable ANL atropisomers have not been isolated from nature until the present study. Phytochemical separation of the methanol extract of the stems and barks of Justicia procumbens led to the isolation of 11 ANL glycosides including four pairs of new atropisomers with stable confirmations at room temperature. Their structures were deduced from elucidation of the extensive spectral data, and their absolute configurations were determined by the circular dichroism, electronic circular dichroism, and X-ray methods as well as the total synthesis of one pair of the atropisomers. The ANL compounds were evaluated for their antiviral potential, and it was found that they displayed great antiviral activity discrepancy between a pair of atropisomers due to the geometric orientation. The 1′P-oriented atropisomers showed much more significant antiviral potency than their corresponding 1′M-oriented counterparts. The biological activity discrepancy caused by the axial chirality will not only inspire synthetic design of novel ANL atropisomers to enrich the structural diversity, but also provide important hints to direct the synthetic approaches toward the antiviral drug development of ANL compounds.
- Zhao, Yang,Ku, Chuen-Fai,Xu, Xin-Ya,Tsang, Nga-Yi,Zhu, Yu,Zhao, Chen-Liang,Liu, Kang-Lun,Li, Chuang-Chuang,Rong, Lijun,Zhang, Hong-Jie
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p. 5568 - 5583
(2021/05/07)
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- A new prenylated coumarin diglycoside with insulin-release promoting activity from Clausena dunniana
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A new prenylated coumarin diglycoside, 6-prenylcoumarin-7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (1) and five known flavonoid glycosides (2–6) were isolated from the leaves and stems of Clausena dunniana. The structures of these isolates were elucidated based on comprehensive MS, UV, IR, and NMR spectroscopic data analysis and comparison with the data reported in literature. Compounds 2–6 are obtained from the title plant for the first time. All these isolates were evaluated for their insulin-release promoting effects, and compounds 1, 2, and 4 exhibited significant activities (2.0 to 3.3-fold higher in comparison with the control, p 0.01) at 40 μM. (Figure presented.).
- Cao, Nan-Kai,Zhu, Si-Si,Chen, Yue-Mei,Ma, Xiao-Li,Zhao, Ming-Bo,Li, Jun,Tu, Peng-Fei,Jiang, Yong
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p. 385 - 391
(2020/09/02)
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- Phenolic glycosides and flavonoids with antioxidant and anticancer activities from Desmodium caudatum
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Descaudatine A (1), an undescribed phenolic glycoside, along with a known analogue (2) and ten flavonoids (3-12), were isolated from the whole plant of Desmodium caudatum. Compounds 1 and 4 exhibited potent antioxidant activities with the IC50 of 58.59 μM and 31.31 μM, respectively, which were approached to that of the positive control Vitamin C (IC50 = 46.32 μM). Meanwhile, 12 showed moderate antioxidant activity with the IC50 of 173.9 μM. Besides, compounds 3 and 6 inhibited the proliferation of HeLa cells with IC50 values of 56.14 μM and 69.04 μM, respectively. Further studies indicated that 3 and 6 could dose-dependently induce PARP cleavage and might trigger caspase-3, 8, 9 activation to induce apoptosis. RXRα is an ideal anticancer target of nuclear receptor. The reporter gene assay of RXRα indicated that 3 and 6 could inhibited the 9-cis-RA induced RXRα transcription in a concentration-dependent manner.
- Xu, Qian-Nan,Zhu, Dan,Wang, Guang-Hui,Lin, Ting,Sun, Cui-Ling,Ding, Rong,Tian, Wen-Jing,Chen, Hai-Feng
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p. 4534 - 4541
(2020/03/23)
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- Six new anthraquinone glycosides from Lasianthus acuminatissimus Merr.
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Six new anthraquinones named lasianthuoside F (1), G (2), H (3), I (4), J (5), K (6) were isolated from an acetone extract of the root of Lasianthus acuminatissimus. Their structures were elucidated by physical and chemical evidence and spectral analysis.
- Liu, Xingxing,Li, Taoan,Liu, Yong,Liu, Hongdong,Chen, Xiaotian,Ming, Jianxin,Lai, Xuewen,Li, Bin
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p. 2535 - 2543
(2019/11/16)
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- Bufadienolides and ecdysteroids from the whole plants of Helleborus niger and their cytotoxicity
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A new bufadienolide (1), two new bufadienolide glycosides (2 and 3), a new ecdysteroid (4), and four known compounds (5–8), were isolated from the whole plants of Helleborus niger L. (Ranunculaceae). The structures of the new compounds (1–4) were determined by spectroscopic analysis, including 2D NMR spectral data, and hydrolytic studies. Compounds 1–6 showed cytotoxicity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, and SBC-3 human small-cell lung cancer cells, with IC50 values ranging from 0.0055 to 1.9?μM. HL-60 cells treated with either 3 or 4 showed apoptosis characteristics, such as nuclear chromatin condensation, accumulation of sub-G1 cells, and activation of caspase-3/7.
- Yokosuka, Akihito,Inomata, Mina,Yoshizawa, Yuka,Iguchi, Tomoki,Mimaki, Yoshihiro
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p. 393 - 402
(2021/01/29)
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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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- Two new compounds with anti-inflammatory activity from Alangium chinense
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A new phenolic glycoside, chinenside A (1), and a new megastigmane glycoside, chinenionside A (2), together with twelve known compounds (3-14), were isolated from the roots of Alangium chinense. Their structures were deduced on the basis of extensive spectroscopic analyses and comparison with data reported in the literature. The anti-inflammatory activity in?vitro of all 13 phenolic glycosides was evaluated against lipopolysaccharide-induced mouse macrophage RAW264.7 cells. The compounds 1, 9, and 10 potentially inhibited the productions of nitric oxide (NO), prostaglandin (PEG2), tumor necrosis factor alpha (TNF-α), interleukin 1 beta (IL-1β) and interleukin 6 (IL-6). Compound 1 (50 μM) showed stronger anti-inflammatory activity than Triptolide (TPL, 20 nm).
- Chen, Jia-Chun,Xiang, Zhi-Nan,Yue, Yue-Dong
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supporting information
(2020/11/12)
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- Sesquiterpenoids, phenolic and lignan glycosides from the roots and rhizomes of Clematis hexapetala Pall. and their bioactivities
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Approximately 17 compounds were isolated from a 60% EtOH aqueous extract of the roots and rhizomes of Clematis hexapetala Pall., including three new guaianolide sesquiterpenoids with 5/7/5-fused rings and 3S-configuration (1–3), five new prenylated tetra-substituted phenolic glycosides (4–8) with 6/6-fused 9H-benzopyran skeleton (5) and 6/7-fused 7,10-dihydro-benzoxepin skeleton (6–8), one new isoferulyl glucoside (9), two new furofuran lignan diglucosides (10–11), and six known compounds. The chemical structures of the new compounds were elucidated via spectroscopic data and electronic circular dichroism (ECD) analyses in combination with a modified Mosher's method. The possible biosynthetic relationships of prenylated tetra-substituted phenols were postulated. In the in vitro assays, compound 16 exhibited moderate TNF-α secretion inhibitory activity with IC50 value of 3.419 μM. Compounds 14–16 displayed potent PTP1B enzymatic inhibitory activities with inhibition ratios of 48.30–86.00%. And compound 16 showed significant PTP1B enzymatic inhibition with IC50 value of 4.623 μM.
- Cai, Lu,Han, Shao-Wei,Li, Shuai,Shao, Si-Yuan
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- New benzoic acid glycosides from Sophora flavescens
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Two new benzoic acid derivatives, sophophenoside A (1) and sophophenoside B (2), were isolated from Sophora flavescens. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. Compounds 1 and 2 were assayed for their hepatoprotective activity on the cytotoxic effect of D-galactosamine on HL-7702 cells, and compound 1 exhibited a moderate hepatoprotective activity at a concentration of 10 μM.
- Jiang, Jian-Shuang,Shen, Yi,Feng, Zi-Ming,Yang, Ya-Nan,Zhang, Xu,Yuan, Xiang,Zhang, Pei-Cheng
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p. 1145 - 1151
(2020/09/01)
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- Chemical constituents of Ligusticum chuanxiong and their anti-inflammation and hepatoprotective activities
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Ligusticum chuanxiong Hort is a famous health promoting plant cultivated in China, and widely consumed due to its various curative effects. To study the potential bioactive constituents from the rhizome of L. chuanxiong, a chemical investigation was thus performed. In present study, we report the isolation and identification of ten new compounds, including two coumarins (1–2), four lignans (3–6), and four phenols (7–10), along with five known compounds (11–15) from the rhizome of L. chuanxiong. The structures of these compounds were unambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. Meanwhile, the anti-inflammation and hepatoprotective activities of all these compounds were evaluated. The results show that compounds 5, 6 and 7 showed excellent inhibition of NO production in LPS-induced RAW 264.7 cells stronger than curcumin, and compounds 5, 7 and 9 exhibited greater hepatoprotective effect than that of bicyclol.
- Feng, Zi-Ming,Han, Bing,Jiang, Jian-Shuang,Yang, Ya-Nan,Yuan, Xiang,Zhang, Pei-Cheng
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supporting information
(2020/07/03)
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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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p. 975 - 980
(2019/01/09)
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- Two new phenolic compounds and some biological activities of Scorzonera pygmaea Sibth. & Sm. subaerial parts
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Phytochemical composition of ethyl acetate fraction and total phenolic content, in vitro antioxidant, anti-inflammatory, antimicrobial activities of petroleum ether, chloroform, ethyl acetate and n-butanol fractions of the ethanol extract obtained from the subaerial parts of Scorzonera pygmaea Sibth. & Sm. (Asteraceae) were investigated. Nine compounds; scorzopygmaecoside (1), scorzonerol (2), cudrabibenzyl A (3), thunberginol C (4), scorzocreticoside I (5) and II (6), chlorogenic acid (7), chlorogenic acid methyl ester (8), 3,5-di-O-caffeoylquinic acid (9) were isolated and identified using spectroscopic methods. All substances were isolated for the first time from this species. Compounds 1 and 2 are new. The fractions showed high antioxidant capacity correlated with their phenolic content and no significant antimicrobial activity against tested bacteria and fungi. COX inhibition test was used to evaluate the anti-inflammatory activity and all the fractions showed low inhibition in comparison with indomethacin.
- ?zbek ?elik, Berna,?zsoy, Nurten,?ahin, Hasan,Koyuncu, Onur,Sar?, Aynur
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p. 621 - 628
(2018/12/04)
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- Benzofuran and coumarin derivatives from the root of Angelica dahurica and their PPAR-γ ligand-binding activity
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A phytochemical investigation of the root of Angelica dahurica led to the isolation of benzofuran and coumarin derivatives. This is the first report of the isolation and identification of three furanocoumarin sulfates from A. dahurica root. The structures of a total of twelve undescribed compounds were determined by extensive spectroscopic analysis, including 2D NMR data, hydrolysis, and solvolysis, followed by either physicochemical and spectroscopic data or X-ray crystallographic analysis. The isolated compounds were evaluated for their PPAR-γ ligand-binding activity, and six compounds showed significant PPAR-γ ligand-binding activity. In particular, the undescribed benzofuran derivative, 3-[6,7-furano-9-hydroxy-4-(2″,3″-dihydroxy-3″-methylbutyloxy)]-phenyl propionic acid, exhibited the most potent PPAR-γ ligand-binding activity and accumulated intracellular lipid in 3T3-L1 cells.
- Matsuo, Yukiko,Yamaguchi, Emi,Hakamata, Ryo,Ootomo, Kanae,Takatori, Kazuhiro,Fukaya, Haruhiko,Mimaki, Yoshihiro
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- Cytotoxic lignans from fruits of Cleistanthus tonkinensis
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Seven new lignans, cleistonkinins A– E (1–5), cleistonkisides A and B (6–7) were isolated from the fruits of Cleistanthus tonkinensis (Euphorbiaceae), together with five known aryltetralin lignans, cleisindoside B (8), cleistantoxin (9), cleisindoside D (10), neocleistantoxin (11) and polygamain (12). Their structures were established from spectral analysis, including mass spectrometry and 2D-NMR. The absolute configurations of 4–7 were determined by analysis of their experimental CD spectra and comparison with calculated electronic circular dichroism (ECD) spectra. Compounds 2 and 6 had selective inhibition with moderate cytotoxicity against Pan C1 and A549 cell lines, respectively. Cleistantoxin (9) was significantly active against A549, HeLa, Hep3B, Pan C1 and MCF7 cell lines while it was less cytotoxic against HeLa cells. Neocleistantoxin (11) exhibited remarkable inhibition toward A549, HeLa, MCF7 and Pan C1. This is the first report for cytotoxicity of 9 and 11 against A549, Hep3B and Pan C1 cell lines.
- Nguyen, Lam Hong,Vu, Van Nam,Phi Thi, Dao,Tran, Viet Hung,Litaudon, Marc,Roussi, Fanny,Nguyen, Van Hung,Chau, Van Minh,Doan Thi Mai, Huong,Pham, Van Cuong
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- Triterpenic saponins from Medicago marina L
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The saponin composition of leaves and roots from Medicago marina L., sea medic, was investigated by a combination of chromatographic, spectroscopic and spectrometric (GC, LC, ESI-MS/MS, NMR) methods. Several compounds were detected and quantified by HPLC using the external standard method. Saponins from this plant species consist of a mixture of high molecular weight bidesmosidic derivatives of medicagenic and zanhic acid, containing up to six sugars in the molecules. Six of the detected saponins were previously isolated and reported as constituents of other Medicago spp.; one saponin was previously described in other plant species; four saponins are undescribed compounds in Medicago and never reported before in other plant species. These are: 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[β-D-apiofuranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester and 3-O-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester. The specific saponins synthesized by M. marina may have a role in its tolerance to environment, representing a reservoir of osmolytic sugars.
- Accogli, Rita,Argentieri, Maria Pia,Avato, Pinarosa,Biazzi, Elisa,Doria, Filippo,Mella, Mariella,Ronga, Domenico,Tava, Aldo
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- Molecular networking-based strategy for the discovery of polyacetylated 18-norspirostanol saponins from Trillium tschonoskii maxim.
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Nine undescribed polyacetylated 18-norspirostanol saponins, trilliumosides A?J, were obtained after a guidance based on a molecular networking strategy from the rhizomes of Trillium tschonoskii. Their structures were established by analysis of comprehensive spectroscopic data and chemical methods after their isolation in pure form. All isolated saponins were evaluated for their cytotoxicities against five selected human cancer cell lines (Huh7,A549,MCF-7,HepG2, and MOLT-4) and anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated NO production model in RAW264.7 macrophages. Trilliumoside D showed significant cytotoxicity against MOLT-4 cell lines with an IC50 value of 1.0 ± 0.1 μM, whereas trilliumosides H and I displayed remarkable anti-inflammatory effects on NO production with inhibitory rates of 56.3 ± 1.5 and 56.2 ± 2.2% at the concentration of 1.0 μM, respectively.
- Li, Dan,Liu, Hui,Ni, Wei,Xiao, Wei-Lie,He, Li,Guo, Zhen-Yu,Qin, Xu-Jie,Liu, Hai-Yang
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- Identification of potential inflammatory inhibitors from Aster tataricus
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Aster tataricus L.f. is a traditional Eastern Asian herbal medicine used for the relief of cough-related illnesses. In this study, 32 known compounds and two novel monoterpene glycosides were isolated from the roots of A. tataricus. With the aid of reported data, elucidation of the root-extract components was carried out using a multitude of spectroscopic techniques. All isolates were investigated for their ability to inhibit nitric oxide (NO) secretion in lipopolysaccharide-activated RAW264.7 cells. Compound 7 remarkably suppressed NO production with an IC50 value of 8.5 μM. In addition, compound 7 exhibited significant inhibitory activity against the production of inflammatory cytokines (prostaglandin E2, interleukin-6, and interleukin-1 beta) and the expression of inflammatory enzymes (inducible nitric oxide synthase and cyclooxygenase-2) via inhibition of nuclear factor-kappa B activation. Moreover, compound 7 effectively prevented the downstream activation of the mitogen-activated protein kinase signaling pathway by inhibiting phosphorylation of c-Jun N-terminal kinases, extracellular signal-regulated kinases, and p38. These results outline compound 7 as a potential inhibitor for the broad treatment of inflammatory diseases, such as atopic dermatitis, asthma, and various allergies.
- Su, Xiang Dong,Jang, Hyun-Jae,Li, Hong Xu,Kim, Young Ho,Yang, Seo Young
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- A new flavanone glycoside isolated from Tournefortia sibirica
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A new flavanone glycoside, (2S)-dihydrooroxylin A 7-O-[β-D-apiosyl(1→2)]-β-D-glucoside (1), and four known compounds (2–5) were isolated from Tournefortia sibirica L. The chemical structures of these compounds were determined by 1 D and 2 D NMR and HR-ESI-MS spectra, and results were compared with data from the literature. These five compounds (1–5) were isolated from the family Boraginaceae for the first time. Anti-inflammatory effects of compounds (1–5) were evaluated in terms of inhibition of production of NO, TNF-α, and IL-6 in LPS-induced RAW 264.7 cells.
- Diao, Shengbao,Jin, Mei,Jin, Chun Shi,Wei, Cheng-Xi,Sun, Jinfeng,Zhou, Wei,Li, Gao
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supporting information
p. 3021 - 3024
(2019/01/04)
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- Megastigmane and abscisic acid glycosides from the leaves of Laurus nobilis L.
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Two new megastigmane glycosides, laurusides E-F (1 and 3) and three known ones (2, 5, and 7), together with a new abscisic acid glycoside, lauruside G (4) and a known one (6), were isolated from a methanolic extract of Laurus nobilis L. leaves using various chromatographic techniques. The structures of these compounds were fully characterized using a combination of spectroscopic techniques including multinuclear and multidimensional NMR and mass spectrometry. All of the isolates were evaluated for their inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW264.7 cells.
- Duc Dat, Le,Viet Duc, Ngo,Thuy Luyen, Bui Thi,Van Oanh, Ha,Jang, Hyun Jae,Huong, Tran Thu,Ho Kim, Young,Thao, Nguyen Phuong
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- Phenylethanoid glycosides from the Schnabelia nepetifolia (Benth.)P.D.Cantino promote the proliferation of osteoblasts
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An investigation of the n-BuOH fraction of Schnabelia nepetifolia (Benth.)P.D.Cantino led to the isolation and identification of 12 undescribed phenylethanoid glycosides (nepetifosides A–L)and one undescribed phenylmethanoid glycoside (nepetifoside M), together with 23 known compounds. The structures of these compounds were determined by spectroscopic analyses including two-dimensional nuclear-magnetic-resonance (2D-NMR)spectroscopy and chemical-hydrolysis methods. Nepetifoside F exhibited strong activity that significantly increased osteoblast proliferation at three concentrations of 0.1, 1, and 10 μM. Moreover, nepetifoside C and nepetifoside D exhibited moderate activities in promoting the proliferation of osteoblasts at medium and high concentrations of 1 μM and 10 μM, respectively.
- Xu, Hong-Tao,Zhang, Cheng-Gang,He, Yu-Qiong,Shi, Song-Shan,Wang, Yong-Li,Chou, Gui-Xin
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p. 111 - 121
(2019/05/24)
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- Phytochemical Study of Stem and Leaf of Clausena lansium
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Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent.
- Peng, Wenwen,Fu, Xiaoxiang,Li, Yuyan,Xiong, Zhonghua,Shi, Xugen,Zhang, Fang,Huo, Guanghua,Li, Baotong
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- Eight ent-kaurane diterpenoid glycosides named diosmariosides a-h from the leaves of diospyros maritima and their cytotoxic activity
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From the leaves of Diospyros maritima, collected from Okinawa Island, eight new glycosides based on ent-kaurane-type diterpenoids, entitled diosmariosides A-H, were isolated. The absolute structure of diosmarioside E (5) was determined by X-ray crystallographic analysis. The structure of diosmarioside H was elucidated to be a dimeric compound between diosmarioside A and a sugeroside through a ketal bond. An assay of cytotoxicity towards the lung adenocarcinoma (A549) cell line was performed. Among the compounds isolated, only diosmarioside D (4) and sugeroside 9 showed strong activity. The anti-microbial activity toward multi-drug resistant strains was also determined, but no activity was observed.
- Kawakami, Susumu,Nishida, Shoko,Nobe, Ayaka,Inagaki, Masanori,Nishimura, Motohiro,Otsuka, Hideaki,Matsunami, Katsuyoshi,Aramoto, Mitsunori,Hyodo, Tadashi,Yamaguchi, Kentaro
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p. 1057 - 1064
(2018/11/21)
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- Anti-inflammatory Potential of Flavonoids from the Aerial Parts of Corispermum marschallii
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The isolation of phenolics from aerial parts of Corispermum marschallii yielded a total of 13 compounds including nine previously undescribed patuletin and spinacetin glycosides. These were identified as patuletin 3-O-β-d-galactopyranosyl-7-O-β-d-glucopyranoside (1), spinacetin 3-O-β-d-galactopyranosyl-7-O-β-d-glucopyranoside (2), patuletin 3-O-(6″-O-β-d-glucopyranosyl)-β-d-galactopyranoside (3), patuletin 3-O-(6″-O-α-l-arabinopyranosyl)-β-d-galactopyranoside (4), patuletin 3-O-(2″-O-(5-O-α-l-arabinopyranosyl)-β-d-apiofuranosyl)-β-d-galactopyranoside (5), patuletin 3-O-(2″-O-β-d-apiofuranosyl)-β-d-galactopyranoside (6), spinacetin 3-O-β-d-galactopyranoside (7), patuletin 3-O-β-d-galactopyranosyl-7-O-(6-O-feruloyl)-β-d-glucopyranoside (8), and spinacetin 3-O-β-d-galactopyranosyl-7-O-(6-O-feruloyl)-β-d-glucopyranoside (9). Structure elucidation was based on UV-visible, multistage MS, and 1D and 2D NMR spectroscopy and chemical derivatization, which allowed the identification on the glycosides with two different hexose moieties occurring at different positions of the aglycones. Most of the compounds tested inhibited the production of pro-inflammatory factors such as ROS, IL-8, and TNF-α in stimulated neutrophils.
- Paw?owska, Karolina,Czerwińska, Monika E.,Wilczek, Marcin,Strawa, Jakub,Tomczyk, Micha?,Granica, Sebastian
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p. 1760 - 1768
(2018/09/10)
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- Megastigmane glycosides from Urena lobata
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Five new megastigmane glycosides, urenalobasides A–E (1–5), together with 11 known ones (6–16) were isolated from Urena lobata. Their structures were determined by extensive spectroscopic and spectrometric data (1D and 2D NMR, IR, and HRESIMS) and calculated electronic circular dichroism method. Compounds 1 and 2 are two unusual megastigmanes structurally containing a 6/5 fused ring system. Compound 3 exhibits inhibition of nitric oxide production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells with IC50 value of 53.7 ± 1.0 μM (positive control, dexamethasone, IC50 = 16.6 ± 0.8 μM).
- Su, Cong,Qi, Bowen,Wang, Juan,Ding, Ning,Wu, Yun,Shi, Xiao-Ping,Zhu, Zhi-Xiang,Liu, Xiao,Wang, Xiao-Hui,Zheng, Jiao,Tu, Peng-Fei,Shi, She-Po
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p. 123 - 128
(2018/02/21)
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- Four new sesquiterpenes from Atractylodes lancea
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Four new sesquiterpene compounds, (5R,7R,10S)-3-O-β-D-glucopyranosylisopterocarpolone-11-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside (1), (5R,7R,10S)-14-carboxylisopterocarpolone-11-O-β-D-glucopyranoside (2), (1R,7R,10R)-1-hydroxylcarissone-11-O-β-D-g
- Jiang, Jian-Shuang,Xu, Kuo,Feng, Zi-Ming,Yang, Ya-Nan,Zhang, Pei-Cheng
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- Naphthalene glycosides in the Thai medicinal plant Diospyros mollis
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This study evaluated methanol extracts from the leaves and branches of the Thai medicinal plant Diospyros mollis (Ebenaceae). Seven triterpenes and 22 aromatic compounds, including five new compounds, were isolated, and their structures were determined. The new compounds had the following structures: diospyrol glycoside (makluoside A, 1), 8,8′-di-O-6-β-d-apiofuranosyl-β-d-glucopyranosyl-6,6′-dimethyl-2,3′-binaphthalene-1-ol-1′,4′- dione (makluoside B, 2), and 3-methyl-1,8- naphthalenediol glycosides (makluosides C-E, 3–5). Makluoside B is the first example of a naphthoquinone glycoside that has both a 3-methyl-1,8-naphthalenediol unit and a 5-hydroxy-7-methyl-1,4-naphthoquinone unit. The hyaluronidase inhibitory activity of the isolates was evaluated, revealing that one of the triterpene derivatives possessed moderate inhibitory activity.
- Suwama, Takaharu,Watanabe, Keisuke,Monthakantirat, Orawan,Luecha, Prathan,Noguchi, Hiroshi,Watanabe, Kenji,Umehara, Kaoru
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p. 220 - 229
(2017/10/17)
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- Phenolic Constituents from Fallopia multiflora (Thunberg) Haraldson
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Four naphtolic glycosides (1-4), three anthraquinones (5-7), two stilbenes (8-9), one benzyl glycoside (10), and one flavonoid (11) were isolated from the roots of Fallopia multiflora. The new compounds were elucidated to be 6-hydroxymusizin 8-O-α-D-apiof
- Nguyen, Thi Thoa,Pham, Thanh Binh,Thao, Nguyen Phuong,Dang, Nguyen Hai,Nguyen, Van Hung,Pham, Van Cuong,Minh, Chau Van,Tran, Quang Hai,Dat, Nguyen Tien
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- Pro-apoptotic activity of acylated triterpenoid saponins from the stem bark of Albizia chevalieri harms
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As a continuation of our interest in apoptosis-inducing triterpenoid saponins from Albizia genus, phytochemical investigation of the stem bark of Albizia chevalieri led to the isolation of three new oleanane-type saponins, named chevalierosides 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, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence. The pro-apoptotic effect of the three saponins was evaluated on two human cell lines (pancreatic carcinoma AsPC-1 and hematopoietic monocytic THP-1). Cytometric analyses showed that saponins 1–3 induced apoptosis of both human cell lines (AsPC-1 and THP-1) in a dose-dependent manner.
- Noté, Olivier Placide,Messi, Lin Marcellin,Mbing, Joséphine Ngo,Azouaou, Sarah Ali,Sarr, Mamadou,Guillaume, Dominique,Muller, Christian Dominique,Pegnyemb, Dieudonné Emmanuel,Lobstein, Annelise
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- The caffeoyl phenylethanoid glycosides from Lindernia ruellioides and their anti-HBV effects
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Five caffeoyl phenylethanoid glycosides, including two new ones linderruelliosides A (1) and B (2), were isolated from the leaves and stems of Lindernia ruellioides. Their structures were elucidated on the basis of spectroscopic methods, including extensive NMR and MS spectra. In addition, all these compounds were tested for their anti-HBV activity. Compounds 1, 3, and 4 showed anti-HBV activities, with IC50 values of 54.87, 30.74, and 69.02?μM for HBsAg and 26.70, 5.17, and 7.08?μM for HBeAg, respectively.
- Wei, Jing-Chen,Wang, Peng-Cheng,Zhou, Xian-Li,Tang, Kun,Luo, Qin,Xu, Qin,Chen, Xue-Jiao,Liang, Cheng-Qin,Chen, Xu
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- Peroxynitrite-Scavenging Glycosides from the Stem Bark of Catalpa ovata
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Ten new glycosides, 6,10-O-di-trans-feruloyl catalpol (1), 6,6′-O-di-trans-feruloyl catalpol (2), 3,4-dihydro-6-O-di-trans-feruloyl catalpol (10), (8R,7′S,8′R)-lariciresinol 9′-O-β-d-(6-O-trans-feruloyl)glucopyranoside (17), and ovatosides A-F (18-22, 24), were isolated from the stem bark of Catalpa ovata along with 19 known compounds. All isolates, except 6 (catalposide) and 9 (6-O-veratroyl catalpol), were found to scavenge peroxynitrite (ONOO-) formed by 3-morpholinosydnonimine. In particular, 12 compounds showed potent activity, with IC50 values in the range 0.14-2.2 μM.
- Kil, Yun-Seo,Kim, Seong Min,Kang, Unwoo,Chung, Hae Young,Seo, Eun Kyoung
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p. 2240 - 2251
(2017/09/01)
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- Sesquiterpenoid and C14-polyacetylene glycosides from the rhizomes of Atractylodes lancea
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Four new glycosides including a eudesmane-type sesquiterpenoid (1), a guaiane-type sesquiterpenoid (2), and two C14-polyacetylenes (3, 4) were isolated from the rhizomes of Atractylodes lancea. Their structures were elucidated by means of spectroscopic and spectrometric analyses (UV, IR, 1D and 2D NMR, and HR-ESIMS). The absolute configurations of their aglycones were established based on the experimental and calculated electronic circular dichroism (ECD), whereas those of monosaccharide moieties were determined by the GC method after chiral derivatization. Compound 4 showed weak anti-inflammatory effects on the LPS-induced NO production in microglia BV2 cells at a concentration of 10?μmol?L?1.
- Xu, Kuo,Feng, Zi-Ming,Jiang, Jian-Shuang,Yang, Ya-Nan,Zhang, Pei-Cheng
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p. 597 - 601
(2017/06/19)
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- Chemical constituents, in vitro antioxidant activity, oral acute toxicity and LD50 determination of Moringa oleifera leaves
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Objective: The objective of this study was undertaken to estimate the total phenolic contents (TPCs), in vitro antioxidant of different solvent extracts of M. oleifera leaves, oral acute toxicity and LD50 determination of the 85% methanolic ext
- Hamed, Manal Mortady,Abdalla, Aboelfetoh Mohamed,Ghareeb, Mosad Ahmed,Saleh, Said Abdelhalim
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p. 240 - 247
(2017/05/12)
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- Three new coumarin glycosides from the stems of Hydrangea paniculata
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Three new coumarin glycosides (1-3), together with three known compounds (4-6), have been obtained from the stems of Hydrangea paniculata Sieb. Their structures were elucidated based on spectroscopic data and chemical evidence. In addition, compounds 1-3
- Ma, Jie,Li, Chuang-Jun,Yang, Jing-Zhi,Li, Yan,Bao, Xiu-Qi,Chen, Nai-Hong,Zhang, Dong-Ming
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p. 320 - 326
(2017/04/10)
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- New minor spirostanol glycosides from Helleborus thibetanus
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Phytochemical reinvestigation of the dried roots and rhizomes of Helleborus thibetanus afforded four new minor spirostanol glycosides (1–4) and four known spirostanol glycosides (5–8). Their structures were determined on the basis of spectroscopic analyse
- Zhang, Hui,Su, Yan-Fang,Yang, Feng-Ying,Gao, Xiu-Mei
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p. 925 - 931
(2017/01/28)
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- From the stems of Hydrangea paniculata Sieb
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known compounds (4, 5), have been isolated from the stems of Hydrangea paniculata Sieb. Their structures have been determined by spectroscopic and chemical methods. Furthermore, compound 1 (50 μM) exhibited significant hepatoprotective activity against N-
- Ma, Jie,Li, Chuang-Jun,Yang, Jing-Zhi,Sun, Hua,Zhang, Dong-Ming
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- Cytotoxic steroidal saponins from Trillium kamtschaticum
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Eight new steroidal saponins, trillikamtosides K–R (1–8), along with three known analogues, were isolated from the whole plants of Trillium kamtschaticum. Their structures were unambiguously established by interpretation of spectroscopic data (MS and NMR) and chemical methods. Compound 1 had a rare aglycone featuring a skeleton of 16-oxaandrost-5-en-3-ol-17-one, which was reported for the first time. The isolated saponins were tested for cytotoxicities against HCT116 cells, and trillikamtoside R (8) was found to show the most cytotoxic effect with an IC50 value of 4.92?μM.
- Qin, Xu-Jie,Si, Yong-Ai,Chen, Yu,Liu, Hui,Ni, Wei,Yan, Huan,Shu, Tong,Ji, Yun-Heng,Liu, Hai-Yang
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supporting information
p. 2267 - 2273
(2017/05/10)
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- Acylated oleanane-type triterpene saponins from the flowers of Bellis perennis show anti-proliferative activities against human digestive tract carcinoma cell lines
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Seven oleanane-type triterpene saponin bisdesmosides, perennisaponins N–T (1–7), were newly isolated from a methanol extract of daisy, the flowers of Bellis perennis L. (Asteraceae). The structures were determined based on chemical and physicochemical data and confirmed using previously isolated related compounds as references. The isolates, including 13 previously reported perennisaponins A–M (8–20), exhibited anti-proliferative activities against human digestive tract carcinoma HSC-2, HSC-4, and MKN-45 cells. Among them, perennisaponin O (2, IC50?=?11.2, 14.3, and 6.9?μM, respectively) showed relatively strong activities. The mechanism of action of 2 against HSC-2 was found to involve apoptotic cell death.
- Ninomiya, Kiyofumi,Motai, Chiaki,Nishida, Eriko,Kitagawa, Niichiro,Yoshihara, Kazuya,Hayakawa, Takao,Muraoka, Osamu,Li, Xuezheng,Nakamura, Seikou,Yoshikawa, Masayuki,Matsuda, Hisashi,Morikawa, Toshio
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p. 435 - 451
(2016/07/16)
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- Eight new eudesmane- and eremophilane-type sesquiterpenoids from Atractylodes lancea
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Phytochemical and pharmacological study on the rhizomes of Atractylodes lancea led to the identification of twenty-one compounds: six new eudesmane-type sesquiterpenoids (1–6), two new eremophilane-type sesquiterpenoids (7, 8), and thirteen known compound
- Xu, Kuo,Feng, Zi-Ming,Yang, Ya-Nan,Jiang, Jian-Shuang,Zhang, Pei-Cheng
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p. 115 - 121
(2016/09/14)
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- Nine new compounds from the whole plants of Rehmannia chingii
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Nine new compounds, together with 16 known analogs, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1–9 were elucidated on the basis of their spectroscopic data and chemical evidence. In addition, the new compounds were tested for their hepatoprotective activities against APAP-induced HepG2 cell damage and their ability to inhibit LPS-induced nitric oxide production in the murine microglia BV2 cell line. Compounds 2 and 5 exhibited pronounced hepatoprotective activities against APAP-induced HepG2 cell damage at a concentration of 10?μM, and compounds 4 and 9 showed moderate inhibitory activity against microglial inflammation factor with IC50values of 3.51 and 7.11?μM, respectively.
- Liu, Yan-Fei,Shi, Guo-Ru,Wang, Xin,Zhang, Chun-Lei,Wang, Yan,Chen, Ruo-Yun,Yu, De-Quan
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p. 509 - 519
(2016/07/07)
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- Gout prophylactic constituents from the flower buds of Lonicera japonica
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Two new sesquiterpene glycosides (R)-dehydroxyabscisic alcohol β-d-apiofuranosyl-(1″ → 6′)-β-d-glucopyranoside (1) and (-)-(1S,2R,6R,7R)-1,2,6-trimethyl-8-hydroxy methyltricyclic[5.3.1.02,6]-undec-8-en-10-one β-d-apiofuranosyl-(1″ → 6′)-β-d-glucopyranoside (2), were isolated from the flower buds of Lonicera japonica. Their structures were determined by spectroscopic and chemical methods. Compound 2 could significantly decrease monosodium urate-mediated cytokine production from activated macrophage through lowering IL-1β and TNFα.
- Xu, Jing-Ren,Li, Guo-Feng,Wang, Jia-Yi,Zhou, Jie-Ru,Han, Jie
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- Efficient chemoenzymatic synthesis of 4-nitrophenyl β-d-apiofuranoside and its use in screening of β-d-apiofuranosidases
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4-Nitrophenyl β-d-apiofuranoside as a chromogenic probe for detection of β-d-apiofuranosidase activity was prepared in 61% yield from 2,3-isopropylidene-α,β-d-apiofuranose through a sequence of five reactions. The synthesis involves one regioselective enz
- Kis, Peter,Potocká, Elena,Mastihuba, Vladimír,Mastihubová, Mária
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- Pyrazole alkaloids from watermelon (Citrullus lanatus) seeds
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Abstract Three new compounds, i.e. 1-[2-(5-hydroxymethyl-1H-pyrrole-2-carbaldehyde-1-yl)ethyl]-1H-pyrazole (1), 1-({[5-(α-d-galactopyranosyloxy)methyl]-1H-pyrrole-2-carbaldehyde-1-yl}-ethyl)-1H-pyrazole (2), and (4-hydroxyphenyl)methanol 4-[β-d-apiofuranosyl(1→2)-O-β-d-glucopyranoside] (3), were isolated from an extract of watermelon seeds. Compounds 1 and 2 were pyrazole-alkaloids with a pyrrole ring. This is the first study to show compounds with pyrrole and pyrazole rings in a molecule isolated from natural products. In the evaluation for melanogenesis inhibitory, compound 1 exhibited modest inhibitory activity on melanogenesis without cytotoxicity. Meanwhile compound 2 showed some inhibitory activity accompanied by some cytotoxicity.
- Kikuchi, Takashi,Ikedaya, Aoi,Toda, Akiko,Ikushima, Kenji,Yamakawa, Takahiro,Okada, Rina,Yamada, Takeshi,Tanaka, Reiko
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