Two New Cytotoxic Pregnane Glycosides from Cynanchum auriculatum

Abstract

Two new pregnane glycosides, kidjoranin 3-O-α-diginopyranosyl-(1→4)-β-cymaropyranoside (1) and kidjoranin 3-O-β-digitoxopyranoside (2), together with one known compound caudatin 3-O-β-cymaropyranoside (3), were isolated from the roots of Cynanchum auriculatum. Their structures were established on the basis of NMR analyses. Compounds 1 - 3 were tested for their in vitro inhibitory activity against the growth of human tumor cell lines SMMC-7721, HeLa and MCF7; all of them displayed marked cytotoxic activities against cells SMMC-7721 and HeLa with IC₅₀ values ranging from 8.6 μM to 58.5 μM, yet no activity against the cell line MCF7 was detected.

Cynanchum auriculatum - Asclepiadaceae - pregnane glycosides - cytotoxic activity

References

• 1 Jiangsu New Medical C ollege. Dictionary of Traditional Chinese Medicines. Shanghai; People’s Health Press 2004: 732-3
• 2 Zhang R S, Ye Y P, Liu X L. Studies on in vitro antitumor activity of total steroidal glycoside from the root of Cynanchum auriculatum. .  Chin Trad Herb Drugs. 2000;  31 599-601
• 3 Zhang R S, Liu Y L, Wang Y Q, Ye Y P, Li X Y. Cytotoxic and apopotosis-inducing properties of auriculosied A in tumor cells.  Chem Biodivers. 2007;  4 887-92
• 4 Yin M. ‘Master’s degree of studies on the germplasm and chemistry constituents of Baishouwu’. Institute of Botany, Jiangsu Province & Chinese Academy of Sciences 2004: 12-4
• 5 Chen J J, Zhang Z X, Zhou J. Cynauricuoside A, B and C, steroid glycosides from the root of Cynanchum auriculatum.  Acta Bot Yunn. 1990;  12 197-210
• 6 Zhang R S, Ye Y P, Shen Y M, Liang H L. Studies on the cytotoxic constituents of Cynanchum auriculatum Royle ex Wight.  Acta Pharm Sin. 2000;  35 431-7
• 7 Zhang R S, Ye Y P, Shen Y M, Liang H L. Two new cytotoxic C-21 steroidal glycosides from the root of Cynanchum auriculatum.  Tetrahedron. 2000;  56 3875-9
• 8 Wang Y Q, Yan X Z, Gong S S, Fu W H. Two new C-21 steroidal glycosides from Cynanchum auriculatum.  Chin Chem Lett. 2002;  13 543-6
• 9 Chen J J, Zhang Z X, Zhou J. The chemical constituents of Cynanchum auriculatum.  Acta Bot Yunn. 1989;  11 358-60
• 10 Gong S S, Liu C D, Liu S L, Du Y R, Kang W, Dong X Q. Studies on constituents of chinese traditional drug baishouwu (Cynanchum auriculatum Royle ex Wight).  Acta Pharm Sin. 1988;  23 276-80
• 11 Warashina T, Noro T. Steroidal glycosides from Cynanchum auriculatum.  Phytochemistry. 1995;  39 199-204
• 12 Tsukamoto S, Hayashi K, Mitsuhashi H. Studies on the constituents of Asclepiadaceae plants. LX.¹⁾ Further studies on glycosides with a novel sugar chain containing a pair of optically isomeric sugars, D- and L-cymarose, from Cynanchum wilfordi.  Chem Pharm Bull. 1985;  33 2294-304
• 13 Warashina T, Noro T. Steroidal glycosides and cardenolide glycosides from Asclepias fruticosa.  Phytochemistry. 1994;  37 217-26