Planta Med 2012; 78(1): 82-85
DOI: 10.1055/s-0031-1280163
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Clerodane Diterpenoids from Tinospora sagittata (Oliv.) Gagnep

Wei Li1 , Chao Huang1 , Songpei Li1 , Fenghua Ma1 , Qin Li2 , Yoshihisa Asada3 , Kazuo Koike1
  • 1Faculty of Pharmaceutical Sciences, Toho University, Funabashi, Chiba, Japan
  • 2Laboratory Center, The Fourth Affiliated Hospital, China Medical University, Shenyang, People's Republic of China
  • 3Faculty of Pharmaceutical Sciences, Tokyo University of Science, Noda, Chiba, Japan
Further Information

Publication History

received April 22, 2011 revised June 30, 2011

accepted July 15, 2011

Publication Date:
27 September 2011 (online)

Abstract

Three new clerodane diterpene glycosides, tinospinosides A (1), B (2), and C (3) were isolated from the roots of Tinospora sagittata (Oliv.) Gagnep. Their structures were determined to be (2S,4aR,6aR,9R,10aS,10bS)-2-(3-furanyl)-9-(β-D-glucopyranosyloxy)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-6a,10b-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (1), (2S,4aS,6aR,9R,10aR,10bS)-2-(3-furanyl)-9-(β-D-glucopyranosyloxy)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-4a-hydroxyl-6a,10b-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (2) and (2S,4aR,6aR,9R,10aR,10bS)-2-(3-furanyl)-9-(β-D-glucopyranosyloxy)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-4a-hydroxyl-6a,10b-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (3), by various spectroscopic analyses, chemical reactions, and computer-assisted calculations. The inhibitory activities of NO production by these compounds and their chemical derivatives in lipopolysaccharide and TNFγ-activated macrophage-like cell line J774.1 were tested. Tinospin A, 12-epi-tinospin A, tinospinoside B, and tinospinoside C showed inhibitory activities of NO production with the IC50 values of 162, 182, 290, and 218 µM, respectively.

Supporting Information

References

  • 1 State of Administration of Traditional Chinese Medicine of People's Republic of China .Zhong Hua Ben Cao. Shanghai: Shanghai Scientific & Technical Publisher; 1999: 1988-1990
  • 2 Shi Q, Shen Y, Zhang C, Liu R, Zhang W. Chemical constituents of two original plants used as Radix Tinosporae.  Zhongguo Tianran Yaowu. 2008;  6 186-190
  • 3 Shi L, Li R, Liu W. Two new furanoid diterpenoids from Tinospora sagittata.  Helv Chim Acta. 2008;  91 978-982
  • 4 Itokawa H, Mizuno K, Tajima R, Takeya K. Furanoditerpene glucosides from Fibraurea tinctoria.  Phytochemistry. 1986;  25 905-908
  • 5 Yonemitsu M, Fukuda N, Kimura T, Isobe R, Komori T. Studies on the constituents of the stems of Tinospora sinensis. II. Isolation and structure elucidation of two new dinorditerpene glucosides, tinosineside A and B.  Liebigs Ann Chem. 1995;  2 437-439
  • 6 Kunii T, Kagei K, Kawakami Y, Nagai Y, Nezu Y, Sato T. Indonesian medicinal plants. I. New furanoditerpenes from Arcangelisia flava MERR. (1).  Chem Pharm Bull. 1985;  33 479-487
  • 7 Sua C, Chen Y, Liou M, Tsai H, Chang W, Wu T. Anti-inflammatory activities of furanoditerpenoids and other constituents from Fibraurea tinctoria.  Bioorg Med Chem. 2008;  16 9603-9609
  • 8 Hosoya T, Yamasaki F, Nakata A, Rahman A, Kusumawati I, Zaini N C, Morita H. Inhibitors of nitric oxide production from Stemona javanica.  Planta Med. 2011;  77 256-258
  • 9 Li W, Wei K, Fu H, Koike K. Structure and absolute configuration of clerodane diterpene glycosides and a rearranged cadinane sesquiterpene glycoside from the stems of Tinospora sinensis.  J Nat Prod. 2007;  70 1971-1976

Dr. Wei Li

Faculty of Pharmaceutical Sciences
Toho University

2-2-1 Myiama, Funabashi

Chiba 274-8510

Japan

Phone: +81 47 4 72 11 61

Fax: +81 47 4 72 14 04

Email: liwei@phar.toho-u.ac.jp