Subscribe to RSS
DOI: 10.1055/s-0031-1298223
© Georg Thieme Verlag KG Stuttgart · New York
Steroidal Glycosides from the Rhizomes of Anemarrhena asphodeloides and Their Antiplatelet Aggregation Activity
Publication History
received October 8, 2011
revised January 4, 2012
accepted January 12, 2012
Publication Date:
03 February 2012 (online)

Abstract
Five new steroidal glycosides, timosaponin J (1), timosaponin K (2), (25S)-karatavioside C (5), timosaponin L (6), and (25S)-officinalisnin-I (8), together with eight known steroidal saponins, timosaponin E1 (3), purpureagitosid (4), timosaponin BII (7), timosaponin B III (9), anemarrhenasaponin I (10), anemarrhenasaponin III (11), anemarrhenasaponin A2 (12), and timosaponin A III (13), were isolated from the rhizomes of Anemarrhena asphodeloides. Their structures were elucidated on the basis of spectroscopic and chemical evidence. The aglycones of compounds 1 and 2 are new aglycones. Compounds 1–13 were evaluated for their platelet aggregation activities, and compound 13 exhibited the strongest inhibitory effect on adenosine diphosphate (ADP)-induced platelet aggregation.
Key words
Anemarrhena asphodeloides - Liliaceae - timosaponins J - K - and L - steroidal glycosides - antiplatelet aggregation activity
References
- 1 Tobari A, Teshima M, Koyanagi J, Kawase M, Miyamae H, Yoza K, Takasaki A, Nagamura Y, Saito S. Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides. Eur J Med Chem. 2000; 35 511-527
- 2 Nakashima N, Kimura I, Kimura M, Matsuura H. Isolation of pseudoprototimosaponin AIII from rhizomes of Anemarrhena asphodeloides and its hypoglycemic activity in streptozotocin-induced diabetic mice. J Nat Prod. 1993; 56 345-350
- 3 Kang Y J, Chung H J, Nam J W, Park H J, Seo E K, Kim Y S, Lee D, Lee S K. Cytotoxic and antineoplastic activity of timosaponin A III for human cancer cells. J Nat Prod. 2011; 74 701-706
- 4 Deng Y, Ma B P, Xu Q P, Xiong C Q, Liu Z Q, Zhao Y, Si Y C. Effect and mechanism of effective component in Zhimu on ability of learning and memory in vascular dementia rats. Chin Pharm Bull. 2005; 21 833-837
- 5 Youn U J, Lee Y S, Jeong H, Lee J, Nam J W, Lee Y J, Hwang E S, Lee J H, Lee D, Kang S S, Seo E K. Identification of antiadipogenic constituents of the rhizomes of Anemarrhena asphodeloides. J Nat Prod. 2009; 72 1895-1898
- 6 Lee B, Trinh H T, Jung K, Han S J, Kim D H. Inhibitory effects of steroidal timosaponins isolated from the rhizomes of Anemarrhena asphodeloides against passive cutaneous anaphylaxis reaction and pruritus. Immunopharmacol Immunotoxicol. 2010; 32 357-363
- 7 Kang L P, Ma B P, Shi T J, Zhang J, Xiong C Q. Two new furostanol saponins from the rhizomes of Anemarrhena asphodeloides. Acta Pharm Sin. 2006; 41 527-532
- 8 Meng Z Y, Xu S X, Meng L H. Timosaponins E1 and E2. Acta Pharm Sin. 1998; 33 693-696
- 9 Tschesche R, Javellana A M, Wulff G. Steroidsaponine mit mehr als einer Zuckerkette, IX Purpureagitosid, ein bisdesmosidisches 22-Hydroxyfurostanol-glycoside aus den Blättern von Digitalis purepure L. Chem Ber. 1974; 107 2828-2834
- 10 Dong J X, Han G Y. Studies on the active constituents of Anemarrhena asphodeloides Bunge. Acta Pharm Sin. 1992; 27 26-32
- 11 Meng Z Y, Xu S X. Steroidal saponins from Anemarrhena asphodeloides Bunge. Chin J Med Chem. 1998; 8 135-136
- 12 Saito S, Nagase S, Ichinose K. New steroidal saponins from the rhizomes of Anemarrhena asphodeloides Bunge (Liliaceae). Chem Pharm Bull. 1994; 42 2342-2345
- 13 Nagumo S, Kishi S, Inoue T, Nagal M. Saponins of Anemarrhenae rhizoma. Yakugaku Zasshi. 1991; 111 306-310
- 14 Agrawal P K, Jain D C, Gupta R K, Thakur R S. Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins. Phytochemistry. 1985; 24 2479-2496
- 15 Agrawal P K. Assigning stereo diversity of the 27-Me group of furostan-type steroidal saponins via NMR chemical shifts. Steroids. 2005; 70 715-724
- 16 Arafa I H, Wieslaw O, Anna S, Cosimo P, Sonia P. Steroidal saponins from the aerial parts of Tribulus pentandrus Forssk. Phytochemistry. 2004; 60 2935-2945
- 17 Zhu X H, Tsumagari H, Honbu T, Ikeda T, Ono M, Nohara T. Peculiar steroidal saponins with opened E-ring from Solanum genera plants. Tetrahedron Lett. 2001; 42 8043-8046
- 18 Dong M, Feng X, Wang B, Wu L, Ikejima T. Two novel furostanol saponins from the rhizomes of Dioscorea penthaica Prain et Burkill and their cytotoxic activity. Tetrahedron. 2001; 57 501-506
- 19 Vollerner Y S, Gorovits M B, Gorovits T T, Abubakirov N K. Steroidal saponins and sapogenins of Allium. XVII. Structure of karatavioside C. Khimiya Prirodnykh Soedinenii. 1980; 3 355-359
- 20 Peng J P, Yao X S, Kobayashi H, Ma C. Novel furostanol glycoside from Allium macrostemon. Planta Med. 1995; 61 58-61
- 21 Mimaki Y, Kuroda M, Takaashi Y, Sashida Y. Steroidal saponins from the stems of Dracaena concinna. Phytochemistry. 1998; 47 1351-1356
- 22 Kawano K, Sakai K, Sato H, Sakamura S. A bitter principle of asparagus: isolation and structure of furostanol saponin in Asparagus storage root. Agric Biol Chem. 1975; 39 1999-2002
Prof. Dr. Bai-ping Ma
Department of Biotechnology
Beijing Institute of Radiation Medicine
No. 27 Taiping Road
Beijing 100850
People's Republic of China
Phone: +86 10 68 21 00 77 ext. 93 02 65
Fax: +86 10 68 21 46 53
Email: mabaiping@sina.com