Planta Med 2009; 75(2): 174-177
DOI: 10.1055/s-0028-1088345
Natural Products Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Alkaloids from Roots of Stemona sessilifolia and Their Antitussive Activities

Xin-Zhou Yang1 , Jian-Yu Zhu2 , Chun-Ping Tang1 , Chang-Qiang Ke1 , Ge Lin3 , Tin-Yan Cheng3 , John A. Rudd3 , Yang Ye1
  • 1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, P.R. China
  • 2Shanghai Institute of Technology, Shanghai, P.R. China
  • 3Department of Pharmacology, the Chinese University of Hong Kong, Hong Kong SAR, P.R. China
Further Information

Publication History

Received: April 30, 2008 Revised: September 22, 2008

Accepted: September 26, 2008

Publication Date:
24 November 2008 (online)

Abstract

Protostemonamide (1), a new protostemonine-type alkaloid, and 12 known compounds were isolated from the roots of Stemona sessilifolia. Their structures were elucidated by 1 D and 2 D NMR spectral and other spectroscopic studies. The main alkaloidal constituents, protostemonine (2), stemospironine (4), and maistemonine (7), showed significant antitussive activity in a citric acid-induced guinea pig cough model following peripheral administration; stemonamine (11) had antitussive activity following i. c. v. administration.

References

  • 1 Duyfjes B EE. Stemonaceae. In: Kalkman C, editor Flora Malesiana Ser 1. Vol. 11 Leiden; Rijksherbarium/Hortus Botanicus 1993: 399-409
  • 2 Tsi Z H, Duyfjes B EE. Stemonaceae. In: Wu ZY, Raven P, editors Flora of China; Vol. 24 Beijing; Science Press 2000: 70-2
  • 3 Greger H. Structural relationships,distribution and biological activities of Stemona alkaloids.  Planta Med. 2006;  72 99-113
  • 4 Götz M, Strunz G M. MTP international review of science. In: Wiesner K, editor Alkaloids. Vol. 9 London; Butterworth 1973: 143-60
  • 5 Sakata K, Aoki K, Chang C F, Sakurai A, Tamura S, Murakoshi S. Stemospironine, a new insecticidal alkaloid of Stemona japonica Miq. isolation, structural determination and activity.  Agric Biol Chem. 1978;  42 457-63
  • 6 Chung H S, Hon P M, Lin G, But P PH, Dong H. Antitussive activity of Stemona alkaloids from Stemona tuberosa. .  Planta Med. 2003;  69 914-20
  • 7 Lin L G, Zhong Q X, Cheng T Y, Tang C P, Ke C Q, Lin G. et al . Stemoninines from the roots of Stemona tuberosa. .  J Nat Prod. 2006;  69 1051-4
  • 8 Lin L G, Li K M, Tang C P, Ke C Q, Rudd J A, Lin G. et al . Antitussive stemoninine alkaloids from the roots of Stemona tuberosa. .  J Nat Prod. 2008;  71 1107-10
  • 9 Schinnerl J, Brem B, But P PH, Vajrodaya S, Hofer O, Greger H. Pyrrolo- and pyridoazepine alkaloids as chemical markers in Stemona species.  Phytochemistry. 2007;  68 1417-27
  • 10 Irie H, Masaki N, Ohno K, Osaki K, Taga T, Uyeo S. Crystal structure of a new alkaloid, stemofoline, from Stemona japonica. .  J Chem Soc Chem Comm. 1970;  17 1066
  • 11 Irie H, Ohno K, Osaki K, Taga T, Uyeo S. X-ray crystallographic determination of the structure of the alkaloid protostemonine.  Chem Pharm Bull. 1973;  21 451-2
  • 12 Ye Y, Xu R S. Studies on new alkaloids of Stemona japonica. .  Chin Chem Lett. 1992;  3 511-4
  • 13 Tan G Y, Zhang C F, Zhang M. Chemical constituents of the roots of wild Stemona sessilifolia. .  J Chin Pharm Univ. 2007;  38 499-501
  • 14 Suzuki K. Alkaloid of Stemona japonica. .  J Pharm Soc Japan. 1931;  51 419-34
  • 15 Koyama H, Oda K. Crystal and molecular structure of stemonine hydrobromide hemihydrate.  J Chem Soc (B). 1970;  1330-3
  • 16 Xu R S, Lu Y J, Chu J H, Iwashita T, Naoki H, Naya Y. et al . Studies on some new Stemona alkaloids – A diagnostically useful 1H NMR line-broadening effect.  Tetrahedron. 1982;  38 2667-70
  • 17 Kakuta D, Hitotsuyanagi Y, Matsaara N, Fukaya H, Takeya K. Structures of new alkaloids sessilifoliamides A–D from Stemona sessilifolia. .  Tetrahedron. 2003;  59 7779-86
  • 18 Hitotsuyanagi Y, Hikita M, Oda T, Kakuta D, Fukaya H, Takeya K. Structures of four new alkaloids from Stemona sessilifolia. .  Tetrahedron. 2007;  63 1008-13
  • 19 Ye Y, Qin G W, Xu R S. Alkaloids of Stemona japonica. .  Phytochemistry. 1994;  37 1205-8
  • 20 Lin W H, Zhong Q X, Xu R S. Studies on new alkaloids of Stemona mairei.  Chin Chem Lett. 1991;  2 369-70
  • 21 Zou C Y, Fu H Z, Lei H M, Li J, Lin W H. New alkaloids from the roots of Stemona japonica Miq.  J Chin Pharm Sci. 1999;  8 185-90
  • 22 Ye Y, Qin G W, Xu R S. Alkaloids of Stemona japonica. .  J Nat Prod. 1994;  57 665-9
  • 23 Iizuka H, Irie H, Masaki N, Osaki K, Uyeo S. X-ray crystallographic determination of the structure of stemonamine, a new alkaloid from Stemona japonica Miq.: Isolation of isostemonamine.  J Chem Soc (D). 1973;  125-6
  • 24 Karlsson J A, Fuller R W. Pharmacological regulation of the cough reflex – from experimental models to antitussive effects in man.  Pulm Pharmacol Ther. 1999;  12 215-28
  • 25 Belvisi M G, Bolser D C. Summary: animal models for cough.  Pulm Pharmacol Ther. 2002;  15 249-50
  • 26 McLeod R L, Gertner S B, Hey J A. Modulation of cardiovascular function by central histamine H3 receptors in conscious guinea pigs.  Eur J Pharmacol. 1991;  209 141-2

Prof. Dr. Yang Ye

State Key Laboratory of Drug Research

Shanghai Institute of Materia Medica

Chinese Academy of Sciences

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Shanghai 201203

People’s Republic of China

Phone: +86-21-5080-6726

Fax: +86-21-5080-6726

Email: yye@mail.shcnc.ac.cn