Citation: Lei Qiao-Shi, Zuo Yi-Han, Lai Chang-Zhi, Luo Jin-Fang, Pang Shu-Wen, Zhou Hua, Yao Xin-Sheng, Tang Jin-Shan. New C₂₁ steroidal glycosides from the roots of Cynanchum stauntonii and their protective effects on hypoxia/reoxygenation induced cardiomyocyte injury[J]. Chinese Chemical Letters, ;2017, 28(8): 1716-1722. doi: 10.1016/j.cclet.2017.05.017 shu

New C₂₁ steroidal glycosides from the roots of Cynanchum stauntonii and their protective effects on hypoxia/reoxygenation induced cardiomyocyte injury

Lei Qiao-Shi ^a,b,1 ,
Zuo Yi-Han ^c,1 ,
Lai Chang-Zhi ^a ,
Luo Jin-Fang ^d ,
Pang Shu-Wen ^a,b ,
Zhou Hua ^c,d ,
Yao Xin-Sheng ^a,b ,
Tang Jin-Shan ^a,b,*,,

a.
Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, China
b.
Key Laboratory of Standard Material in Natural Medicine of Guangdong Province, Guangzhou Xiangxue Pharmaceutical Ltd. Co., Guangzhou 510663, China
c.
Faculty of Chinese Medicine, Macau University of Science and Technology, Macao, China
d.
State Key Laboratory of Quality Research in Chinese Medicine, Macau University of Science and Technology, Macao, China

Corresponding author: Tang Jin-Shan, gztangjinshan@126.com

Received Date: 4 March 2017
Revised Date: 2 May 2017
Accepted Date: 4 May 2017
Available Online: 17 August 2017

Figures(4)

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, HRESI-TOF-MS, 1D, and 2D-NMR data, together with chemical methods, which showed interesting 13, 14:14, 15-disecopregnane-type skeleton or 14, 15-secopregnane-type skeleton C₂₁ steroidal glycosides. Among them, compound 1 was determined to be glaucogenin C 3-O-β-D-glucopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-thevetopyranoside. Compound 2 was characterized to be hirundigenin 3-O-α-L-diginopyr-anosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-3'-demethyl-theveto-pyranoside. Compound 3 was identified to be (14S, 16S, 20R)-14, 16-14, 20-15, 20-triepoxy-14, 15-secopregn-5-en-3-ol-3-O-α-L-cymaropyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-oleandropyranoside. Compound 4 was identified to be (14S, 16S, 20R)-14, 16-14, 20-15, 20-triepoxy-14, 15-secopregn-5-en-3-ol-3-O-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-thevetopyranoside. Among them, compound 2 was hirundigenin type C₂₁ steroidal glycoside that existed in nature as epimers due to the presence of 14-hemiketal hydroxyl group in its structure. In addition, the anti-inflammatory and cardiomyocyte protective effects of compounds 1-4 were evaluated.Wefound that they exhibited significant protective effects on hypoxia/reoxygenation induced cardiomyocyte injury, but did not showed obvious anti-inflammatory function.
- Cynanchum stauntonii,
- C₂₁ steroidal glycoside,
- Chemical constituent,
- Hirundigenin,
- Cardiomyocyte protection,
- Hypoxia/reoxygenation
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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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通讯作者: 陈斌, bchen63@163.com

New C₂₁ steroidal glycosides from the roots of Cynanchum stauntonii and their protective effects on hypoxia/reoxygenation induced cardiomyocyte injury