- Two new steroidal glycosides from Cynanchum otophyllum Schneid
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Two new C21 steroidal glycosides were isolated from Cynanchum otophyllum Schneid. Their structures were elucidated as qinyangshengenin-3-O-β-d-digitoxopyranoside (1) and rostratamine-3-O-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (2) on the basis of chemical and spectroscopic methods, including 1D and 2D NMR experiments.
- Yang, Xin-Xin,Bao, Yong-Rui,Wang, Li-Fen,Wang, Shuai,Bao, Li-Na,Guan, Yu-Peng,Meng, Xian-Sheng
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- Two new glycosides and one new neolignan from the roots of Cynanchum stauntonii
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Three new compounds including one C21-steroidal glycoside, one methylglycoside, and one neolignan, named as Deoxyamplexicogenin A-3-O-yl-4-O-(4-O-α-L-cymaropyranosoyl-β-D-digitoxopyranosoyl)-β-D-canaropyranoside (1), Methyl-O-α-L-cymaropyranosoyl-(1 → 4)-β-D-digitoxopyranoside (2), and (+)-(7S, 8R, 7′E)-5-hydroxy-3, 5′-dimethoxy-4′, 7-epoxy-8, 3′-neolign-7′-ene-9, 9′-diol 9′-ethyl ether (3), respectively, were isolated from the roots of Cynanchum stauntonii. The structure elucidations were achieved by in-depth spectroscopic examination, mainly including the experiments and analyses of multiple 1D- and 2D-NMR and HRESIMS and CD analysis and qualitative chemical tests. Cytotoxicity activities of compounds 1-3 were evaluated against five tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780) in cell based assays where they were found to be inactive.
- Yu, Jin-Qian,Zhao, Lei
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- Triterpene glycosides and phenylpropane derivatives from Staurogyne concinnula possessing anti-angiogenic activity
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After anti-angiogenic activity screening, the potential n-butanol layer partitioned from the ethanol extract of Staurogyne concinnula was conducted. Further purification by Diaion HP20 column and preparative HPLC chromatography, four undescribed triterpen
- Vo, Thanh-Hoa,Lin, Yu-Chi,Liaw, Chia-Ching,Pan, Wen-Pin,Cheng, Jing-Jy,Lee, Ching-Kuo,Kuo, Yao-Haur
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- New knowledge about old drugs; a cardenolide type glycoside with cytotoxic effect and unusual secondary metabolites from Digitalis grandiflora Miller
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Phytochemical investigation of the aerial parts of Digitalis grandiflora Miller (Plantaginaceae) led to the isolation of an undescribed cardenolide type glycoside digigrandifloroside (1) along with five known compounds, rengyoside A (2), rengyoside B (3), cleroindicin A (4), salidroside (5), and cornoside (6), from its aqueous fraction of methanolic extract. Structures of the isolated compounds were determined by means of spectroscopic techniques. 1–6 were isolated for the first time from D. grandiflora. 2 and 3 are being reported for the first time from Digitalis genus and Plantaginaceae family with this study. This is the second report for occurrence of 4 from a Digitalis species. Cytotoxic activity of the aqueous fraction was also tested against HEp-2 (Human larynx epidermoid carcinoma) and HepG2 (Human hepatocellular carcinoma) cancer cell lines and L929 (Mouse fibroblast cell) non-cancerous cell line. Aqueous fraction showed stronger cytotoxicity on HEp-2 cells than HepG2. Therefore, the cytotoxic activity of 1, 2, 4, and 6 were tested against HEp-2 and L929 cell lines. 3 and 5 couldn't be tested due to their insufficient amount. 1 showed the highest cytotoxicity against HEp-2 cells with IC50 value 10.1 μM when compared with the positive control, etoposide and 2–6 (IC50 of etoposide; 39.5 μM).
- Kutluay, Vahap Murat,Makino, Toshiaki,Inoue, Makoto,Saracoglu, Iclal
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- Cytotoxic Pregnane Steroidal Glycosides from Chonemorpha megacalyx
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Three new C21 pregnane steroids, chonemorphols A-C (1, 3, and 4), 11 new C21 steroidal glycosides, chonemorphosides A-K (2 and 5-14), and 11 known compounds (15-25) were obtained from the vines and leaves of Chonemorpha megacalyx Pierre. Their structures were established using extensive spectroscopic data. The X-ray crystallographic data of 1 and 3 permitted definition of their absolute configurations. Notably, 1 and 2 possessed an uncommon 6/5/6/5/5-fused steroidal ring system. Compound 7 displayed significant cytotoxicity against several cancer cell lines with IC50 values of 2.0-3.6 μM.
- Yuan, Fang-Yu,Wang, Xiao-Ling,Wang, Tian,Shen, Tao,Ren, Dongmei,Lou, Hongxiang,Wang, Xiao-Ning
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p. 1542 - 1549
(2019/07/05)
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- New Immunomodulating Polyhydroxypregnane Glycosides from the Roots of Cynanchum otophyllum C.K.Schneid.
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Seven new polyhydroxypregnane glycosides, named cynotophyllosides P–V, together with three known analogs were isolated from the roots of Cynanchum otophyllum C.K.Schneid. Their structures were elucidated by a variety of spectroscopic techniques, as well as acid-catalyzed hydrolysis. All isolates were tested for their immunological activities in vitro against Con A- and LPS-induced proliferation of mice splenocytes. Immunoenhancing (for 1, 9) and immunosuppressive (for 2) activities were observed. Furthermore, cynotophylloside R (3) showed immunomodulatory as it enhanced the proliferation of splenocytes in low concentration and suppressed immune cells in concentration more than 1.0 μg/ml.
- Zhan, Zha-Jun,Bao, Shu-Min,Zhang, Yue,Qiu, Fei-Jun,Shan, Wei-Guang,Ma, Lie-Feng
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- Two new steroidal saponins from the roots of Cynanchum limprichtii
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As a part of our continuing research for bioactive constituents from Cynanchum limprichtii Schltr., two new C21 steroidal glycosides limproside A (1) and limproside B (2) were isolated from the roots of Cynanchum limprichtii. Their structures were elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. The cytotoxicity of two compounds against two selected human cancer cell lines was assayed.
- Liu, Jia-Chuan,Yu, Li-Li,Tang, Ming-Xu,Lu, Xiao-Jie,Zhao, Dan,Wang, Hai-Feng,Chen, Gang,Su, Guang-Yue,Pei, Yue-Hu
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p. 875 - 882
(2017/11/29)
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- Two new 14, 15-secopregnane-type steroidal glycosides from the roots of Cynanchum limprichtii
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Two new steroidal glycosides 1 and 2, along with three known ones (3–5), were isolated from the 95% ethanol extract of the roots of Cynanchum limprichtii Schltr. The structure of the new compounds was elucidated as 3-O-α-L-diginopyranosyl-(1→4)-β-D-digito
- Liu, Jia-chuan,Yu, Li-li,Chen, Shao-fei,Lu, Xiao-jie,Zhao, Dan,Wang, Hai-feng,Chen, Gang,Pei, Yue-hu
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p. 261 - 267
(2017/10/06)
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- New C21 steroidal glycosides from the roots of Cynanchum stauntonii and their protective effects on hypoxia/reoxygenation induced cardiomyocyte injury
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Phytochemical investigations from the roots of Cynanchum stauntonii led to obtain four new C21 steroidal glycosides (1–4) and one known compound stauntoside F (5). Their chemical structures were characterized by sophisticated analyses of IR, HR
- Lei, Qiao-Shi,Zuo, Yi-Han,Lai, Chang-Zhi,Luo, Jin-Fang,Pang, Shu-Wen,Zhou, Hua,Yao, Xin-Sheng,Tang, Jin-Shan
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p. 1716 - 1722
(2017/07/27)
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- Cytotoxic and apoptosis-inducing activity of C21 steroids from the roots of Cynanchum atratum
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Two new (1–2) and two known C21 steroids (3–4) were isolated from the roots of Cynanchum atratum. Their structures were elucidated by detailed 1D and 2D spectroscopic. The MTT assay showed that compounds 1–4 displayed obvious cytotoxic activities against HepG2 cells with IC50 values ranging from 10.19?μM to 76.12?μM. Compounds 1–3 also exhibited cytotoxic effects in A549 cells with IC50 values of 30.87–95.39?μM. Compound 3 showed the antiproliferative activity via G0/G1 cell cycle arrest and proapoptosis in HepG2 cells by Flowcytometry analysis. Western blotting analysis revealed that compound 3 could induce HepG2 cell apoptosis via the mitochondrial pathway by downregulating Bcl-2 expression, upregulating Bax protein expression, and activating caspase-9 and caspase-3.
- Zhang, Jian,Ma, Lin,Wu, Zheng-Feng,Yu, Shu-Le,Wang, Lei,Ye, Wen-Cai,Zhang, Qing-Wen,Yin, Zhi-Qi
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- C21 steroidal glycosides from Cynanchum stauntonii induce apoptosis in HepG2 cells
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Two new (1–2) and three known (3–5) C21 steroidal glycosides were isolated from Cynanchum stauntonii. Their structures were elucidated on the basis of 1D and 2D-NMR spectroscopic data as well as HRTOFMS analysis. The cytotoxicity of the compoun
- Che, Chun-Tao,Ma, Lin,Wang, Lei,Wei, Yu-Jian,Wu, Zheng-Feng,Ye, Wen-Cai,Yin, Zhi-Qi,Yu, Shu-Le,Zhang, Jian,Zhang, Qing-Wen,Zhao, Ming
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- Cardenolide and Steroid Glycosides from Alafia sp., an Antimalarial Plant from Madagascar
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New cardenolide glycoside 1 and steroid glycoside 2, named respectively corotoxigenin-3-O-β- digitalopyranosyl-(1–4)-O-β-digitoxopyanoside and 5?-pregnene-3β,16α,20(S)-diol 20-O-[β-Ddigitalopyranosyl (1→2)-β-D-glucopyranoside], have been isolated from the
- Rakotondramanga,Raharisololalao,Rakotoarimanga,Krebs, H. Ch.,Rasoanaivo,Razakarivony,Randrianasolo
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p. 865 - 869
(2017/03/15)
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- Identification and Evaluation of Antiepileptic Activity of C21 Steroidal Glycosides from the Roots of Cynanchum wilfordii
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Nine new C21 steroidal glycosides, named cynawilfosides A-I (1-9), along with 12 known compounds were isolated from the roots of Cynanchum wilfordii. The structures of the new compounds were elucidated by spectroscopic analysis and chemical methods. The five major components, cynawilfoside A (1), cynauricoside A (11), wilfoside C1N (16), wilfoside K1N (17), and cyanoauriculoside G (18), exhibited significant protection activity in a maximal electroshock (MES)-induced mouse seizure model with ED50 values of 48.5, 95.3, 124.1, 72.3, and 88.1 mg/kg, respectively.
- Li, Jin-Long,Gao, Zhao-Bing,Zhao, Wei-Min
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- New Sweet-Tasting C21-Pregnane Glycosides from Pericarps of Myriopteron extensum
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Ten novel C21 pregnane glycosides, extensumside C-L (1-10), were isolated as highly sweet-tasting substances from the edible pericarps of Myriopteron extensum (Wight) K. Schum by sensory-guided fractionation and purification. Their structures were determined through 1D and 2D NMR, such as HSQC, HMBC, 1H-1H COSY, HSQC-TOCSY, and ROESY, as well as other spectroscopic analysis combined with chemical evidence. These compounds shared the same aglycone, 3β,16α-dihydroxy-pregn-5-en-20-one, and contained the deoxysugar chain and the glucose chain which were linked to C-3 and C-16 of the aglycone, respectively. The sweetness potency was evaluated by a human sensory panel test and preliminary structure-taste relationship was discussed. The sweetness intensities of these compounds are between 50 and 400 times greater than that of sucrose. Furthermore, quantitation analyses of compounds 1, 3, 4, and 6 in different parts of M. extensum indicated that the concentrations of these sweet components in the pericarps are obviously higher than those in stems and roots.
- Sun, Guo,Dai, Qin,Zhang, Hong-Xia,Li, Zhi-Jian,Du, Zhi-Zhi
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p. 9381 - 9389
(2016/12/23)
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- Hirundigenin type C21 steroidal glycosides from Cynanchum stauntonii and their anti-inflammatory activity
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Six new hirundigenin-type C21 steroidal glycosides, namely hirundigosides E-J (1-6), were obtained from the dried roots of Cynanchum stauntonii. Their chemical structures were elucidated by analyses of HR ESI-TOF MS, 1D, 2D-NMR, and X-ray cryst
- Lai, Chang-Zhi,Liu, Hai-Bin,Liu, Jian-Xin,Ouyang, Qin,Pang, Shu-Wen,Zhou, Hua,Tian, Hai-Yan,Liu, Liang,Yao, Xin-Sheng,Tang, Jin-Shan
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p. 59257 - 59268
(2016/07/06)
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- C21 steroidal glycosides from the roots of Cynanchum paniculatum
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As a part of our continuing research for bioactive constituents from Cynanchum plants, four new C21 steroidal glycosides, cynapanoside D-G (1–4), together with six known compounds (5–10) were isolated from the roots of Cynanchum paniculatum (Bge.) Kitag. Their structures were elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. Compound 8 exhibited potent inhibitory activities against HL-60, HT-29, PC-3 and MCF-7 cell lines with IC50 values of 8.3, 7.5, 34.3 and 19.4?μM, respectively and compounds 1–4 and 9 displayed moderate cytotoxicity against the four cell lines. The in vitro antioxidant activities of compounds 1–4, 8 and 9 were assayed by DPPH radical scavenging activity. Antibacterial and antifungal activities of compounds 1–4, 8 and 9 were also tested.
- Zhao, Dan,Feng, Baomin,Chen, Shaofei,Chen, Gang,Li, Zhifeng,Lu, Xiaojie,Sang, Xianan,An, Xiao,Wang, Haifeng,Pei, Yuehu
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- Steroidal glycosides from the roots of Cynanchum stauntonii and their effects on the expression of iNOS and COX-2
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Six new steroidal glycosides, named stauntosides O-T (1-6), along with eight known compounds (7-14), were obtained from the 95% aqueous ethanol extract of the roots of Cynanchum stauntonii. Their chemical structures were elucidated by IR, HR ESI-MS/MS, 1H- and 13C NMR, 1H-1H COSY, HSQC, HSQC-TOCSY, and HMBC spectroscopic analyses, which showed interesting 13,14:14,15-disecopregnane-type or 14,15-secopregnane-type C21 steroidal glycosides. The glycosides' anti-inflammatory effects were investigated by detecting the inhibitory effects of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) on RAW246.7 murine macrophage cells stimulated by lipopolysaccharide (LPS). Our results showed that compounds 1, 5, 8, 9, 11, and 13 could significantly inhibit iNOS expression, and compounds 5 and 7 could clearly reduce COX-2 expression in RAW246.7 cells stimulated by LPS compared to cells stimulated with LPS and not treated with other compounds. Thus, compounds 1, 5, 7-9, 11, and 13 have the potential to mediate anti-inflammatory effects, with compound 5 having a greater anti-inflammatory effect than the other compounds.
- Lai, Chang-Zhi,Liu, Jian-Xin,Pang, Shu-Wen,Dai, Yi,Zhou, Hua,Mu, Zhen-Qiang,Wu, Jun,Tang, Jin-Shan,Liu, Liang,Yao, Xin-Sheng
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- Minor cytotoxic cardenolide glycosides from the root of Streptocaulon juventas
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In order to determine new minor natural cardenolide glycosides as cytotoxic candidates, we isolated six new cardenolide glycosides together with four known ones, which had never previously been reported in the genus, by bioassay-guided separation from the 75% ethanol extract of Streptocaulon juventas (Asclepiadaceae). Their structures were elucidated on the basis of spectroscopic analysis, including homo- and heteronuclear correlation NMR experiments (COSY, HSQC and HMBC). The cytotoxic activities of these compounds were evaluated against A549 and NCI-H460 cell lines by MTT assay and compound 7 exhibited inhibitory activity against the two cell lines, while other compounds displayed a range of inhibitory activity against NCI-H460 and A549 cells. Their structure-activity relationships were also discussed.
- Ye, Chun,Wang, Hua,Xue, Rui,Han, Na,Wang, Lihui,Yang, Jingyu,Wang, Yu,Yin, Jun
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- Minor cytotoxic cardenolide glycosides from the root of Streptocaulon juventas
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In order to determine new minor natural cardenolide glycosides as cytotoxic candidates, we isolated six new cardenolide glycosides together with four known ones, which had never previously been reported in the genus, by bioassay-guided separation from the 75% ethanol extract of Streptocaulon juventas (Asclepiadaceae). Their structures were elucidated on the basis of spectroscopic analysis, including homo- and heteronuclear correlation NMR experiments (COSY, HSQC and HMBC). The cytotoxic activities of these compounds were evaluated against A549 and NCI-H460 cell lines by MTT assay and compound 7 exhibited inhibitory activity against the two cell lines, while other compounds displayed a range of inhibitory activity against NCI-H460 and A549 cells. Their structure-activity relationships were also discussed.
- Ye, Chun,Wang, Hua,Xue, Rui,Han, Na,Wang, Lihui,Yang, Jingyu,Wang, Yu,Yin, Jun
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- Two new steroidal glycosides from Cynanchum wallichii
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Two new C21 steroidal glycosides were isolated from Cynanchum wallichii Wight. Their structures were elucidated as caudatin-3-O-β-d-glucopyranosyl- (1 → 4)-β-d-oleandropyranosyl-(1 → 4)-β-d-cymaropyranosyl-(1 → 4)-β-d-digitoxopyranoside (1) and caudatin-3
- Wang, Ding,Pan, Wen-Hao,Bao, Yong-Rui,Yang, Xin-Xin,Meng, Xian-Sheng
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p. 759 - 763
(2014/08/18)
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- Nine new steroidal glycosides from the roots of Cynanchum stauntonii
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Nine new steroidal glycosides, named as stauntosides C-K (2, 5, 7-10, 13, 14, and 16), along with seven known compounds (1, 3, 4, 6, 11, 12, and 15) were isolated from the 95% ethanol extract of the roots of Cynanchum stauntonii. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses, mainly 1D and 2D NMR, and HRESI-MS, and qualitative chemical methods. Their significance in terms of the chemotaxonomy of C. stauntonii is discussed.
- Yu, Jin-Qian,Deng, An-Jun,Qin, Hai-Lin
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- Appetite suppressing pregnane glycosides from the roots of Cynanchum auriculatum
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In the search for plant alternatives to Hoodia gordonii containing P57, a pregnane glycoside with potential appetite suppressant effect, the roots of Cynanchum auriculatum were investigated. As a result, 15 pregnane glycosides including nine never previously reported were isolated. Their structures were elucidated on the basis of extensive spectroscopic analyses and chemical methods. Appetite suppressant effect and body weight loss were observed when tested with the most abundant pregnane glycoside, wilfoside K1N, in an in vivo test with rats.
- Liu, Shuangzhu,Chen, Zhenhua,Wu, Jian,Wang, Luoyi,Wang, Hongmin,Zhao, Weimin
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p. 144 - 153
(2013/10/21)
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- Anthraquinone glycosides from marine Streptomyces sp. strain
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Two new anthraquinone glycosides Strepnoneside A (1) and Strepnoneside B (2), together with Chromomycin A3 (3), were isolated from cultures of the marine Streptomyces sp. strain. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. Compound 3 exhibited cytotoxic activities against HCT 116 cell lines (IC50 = 300 ± 11 pM).
- Lu, Yuanyuan,Xing, Yingying,Chen, Chen,Lu, Jiansheng,Ma, Yihua,Xi, Tao
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body text
p. 459 - 462
(2012/10/08)
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- Five new pregnane glycosides from the stems of Marsdenia tenacissima
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Activity-guided fractionation of the stems of Marsdenia tenacissima led to the isolation of five new pregnane glycosides, namely marstenacissides E (1), F (2), G (3), H (4), and I (5). Their structures were determined on the basis of 1H and 13C NMR, COSY, TOCSY, ROESY, and FABMS experiments.
- Xia, Zeng-Hua,Mao, Shi-Long,Lao, Ai-Na,Uzawa, Jun,Yoshida, Shigeo,Fujimoto, Yasuo
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experimental part
p. 477 - 485
(2011/07/08)
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- A new pregnane glycoside and oligosaccharide from Parabarium huaitingii
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Two new compounds, along with two known compounds, were isolated from the barks of Parabarium huaitingii, and their structures were determined as 5α-pregn-6-ene-3β,17α,20(S)-triol-20-O-β-D- digitoxopyranoside (1), cymaropyranurolactone 4-O-β-D-digitalopyranosyl-(1 → 4)-O-β-D-cymaropyranosyl-(1 → 4)-O-β-D-oleandropyranosyl-( 1 → 4)-O-β-D-cymaropyranoside (2), 3β,17α,20(S)- trihydroxy-5α-pregn-6-ene (3), and 5a-pregn-6-ene-3β,17α,20(S)- triol-3-O-β-D-digitalopyranoside (4) by spectroscopic methods.
- Lei, Ting,Zhang, Lei,Jiang, Hai-Yan,Hu, Ying,Hong, Ai-Hua,Cen, Ying-Zhou
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experimental part
p. 1030 - 1035
(2012/03/11)
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- Two new C21 steroids from the roots of Cynanchum otophyllum
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Two new C21 steroids, 12β-O-acetyl-20-O-(2-methylbutyryl)- sarcostin and its 3-O-digitoxopyranoside (1-2) were isolated from the roots of Cynanchum otophyllum, together with three known steroids, namely deacetylmetaplexigenin (3), sarcostin (4), and kidjoranin 3-O-β-D- digitoxopyranoside (5). The structures of the new steroids were established by spectroscopic and chemical methods, especially two-dimensional NMR techniques.
- Shi, Lin-Mei,Liu, Wen-Hong,Yu, Qing,Wan, Hai-Tong
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experimental part
p. 126 - 128
(2011/07/07)
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- C21 steroidal glycosides from Cynanchum wilfordii
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Eight new C21 steroidal glycosides, named wilfosides A-H (1 - 8, resp.), along with one known compound wilfoside KIN (9), were isolated from the roots of Cynanchum wilfordii. The structures of the new glycosides were determined on the basis of
- Xiang, Wen-Juan,Ma, Lei,Hu, Li-Hong
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experimental part
p. 2659 - 2674
(2010/04/04)
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- Acylated-oxypregnane glycosides from the roots of asclepias syriaca
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Twenty new pregnane glycosides were obtained from the roots of Asclepias syriaca L. (Asclepiadaceae). These glycosides were confirmed to contain ikemagenin, 12-0-nicotinoyllineolon, 5α,6-dihydroikemagenin, and 12-O-tigloylisolineolon, as their aglycones,
- Warashina, Tsutomu,Noro, Tadataka
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experimental part
p. 177 - 184
(2009/10/02)
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- SILYL NITRONATES AND NITRILE OXIDES IN ORGANIC SYNTHESIS. A NOVEL ROUTE TO D,L-DEOXYSUGARS. USE OF ALUMINIUM OXIDE AS SOLID PHASE BASE FOR GENERATION OF NITRILE OXIDES FROM HYDROXIMIC ACID CHLORIDES
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Novel methodology is developed for a three step synthesis of deoxyaldoses and deoxyketoses. 1.Regioselective addition of silyl nitronate or nitrile oxide to a diene. 2.Stereospecific hydroxylation of the double bond. 3.Unmasking of the aldol moiety by catalytic reduction of the 2-isoxazoline.The syntheses of D.L-deoxyribose, D,L-oleose, D,L-digitoxose, D,L-2-deoxygalactose, 1,3-dideoxyfructose, 3-deoxyfructose etc. are described.Basic aluminium oxide is introduced as a solid phase base for the one step synthesis of 2-isoxazolines from aldoximes and olefins.An X-ray diffraction study of compound 13c verifies the stereochemical assignments.
- Torssell, K. B. G.,Hazell, A. C.,Hazell, R. G.
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p. 5569 - 5576
(2007/10/02)
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