Distribution, bioactive components and biological activities of Stemona species in Thailand

Medicinal Plants - International Journal of Phytomedicines and Related Industries

Volumn 2, Issue 1, 2010, Pages 1-12

  Kongkiatpaiboon, Sumet ^a   Gritsanapan, Wandee ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Antitussive; Insecticide; Stemona; Stemona alkaloids; Stemonaceae; Stilbenoids

Indexed keywords

ALKALOID DERIVATIVE; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; ANTITUSSIVE AGENT; DIHYDROSTILBENE DERIVATIVE; HERBACEOUS AGENT; INSECTICIDE; NEOTUBEROSTEMONINE; NEOTUBEROSTEMONINOL; PINOSYLVIN; PLANT EXTRACT; PLANT MEDICINAL PRODUCT; PROTOSTEMONINE; RESVERATROL; SAXORUMAMIDE; STEMANTHRENE; STEMOAMIDE; STEMOBURKILLINE; STEMOCURTISINOL; STEMOFOLINE; STEMOFURAN; STEMOKERRINE; STEMONA EXTRACT; STEMONINE; STEMOPHYLLINE; STILBENOID DERIVATIVE; STILBOSTEMIN; TOCOPHEROL DERIVATIVE; TUBEROSTEMONINE A; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIFUNGAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; BIOACCUMULATION; BIOSYNTHESIS; CHEMICAL COMPOSITION; DRUG ACTIVITY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; FUNGAL STRAIN; INSECTICIDAL ACTIVITY; NONHUMAN; PRIORITY JOURNAL; REVIEW; STEMONA; STEMONACEAE; THAILAND;

FUNGI; STEMONA; STEMONACEAE; TUBEROSA;

EID: 78651379568     PISSN: 09754261     EISSN: 09756892     Source Type: Journal    
DOI: 10.5958/j.0975-4261.2.1.001     Document Type: Review

References (61)

1. Adams M, Pacher T, Greger H and Bauer R (2005). Inhibition of leukotriene biosynthesis by stilbenoids from Stemona species. J. Nat. Prod., 68: 83-85. (Pubitemid 40175935)
2. Akanitapichat P, Tongngok P, Wangmaneerat A and Sripanidkulchai B (2005). Antiviral and anticancer activities of Stemona collinsae. Thai J. Pharm. Sci., 29(3-4): 125-126.
3. Anonymous (2005). Pharmacopoeia commission of people's republic of China. The pharmacopoeia of the people's republic of China, Part 1. Chemical Industry Publishing House, Beijing, China, p. 100.
4. Brem B, Seger C, Pacher T, Hofer O, Vajrodaya S and Greger H (2002). Feeding deterrence and contact toxicity of Stemona alkaloids-A source of potent natural insecticides. J. Agric. Food Chem., 50: 6383-6388. (Pubitemid 35216743)
5. Brem B, Seger C, Pacher T, Hartl M, Hadacek F, Hofer O, Vajrodaya S and Greger H (2004). Antioxidant dehydrotocopherols as a new chemical character of Stemona species. Phytochemistry, 65: 2719-2729. (Pubitemid 39298170)
6. Chuakul W, Saralamp P, Paonil W, Temsiririrkkul R and Clayton T (1997). Medicinal plants in Thailand, vol. 2, Amarin printing and publishing, Bangkok, Thailand.
7. Chung H-S, Hon P-M, Lin G, But PP and Dong H (2003). Antitussive activity of Stemona alkaloids from Stemona tuberosa. Planta Med., 69: 914-920. (Pubitemid 38005447)
8. Dien P-H, Lin L-G, Tang C-P, Ke C-Q and Ye Y (2009). Bisbenzopyrans and alkaloids from the roots of Stemona cochinchinensis. Nat. Prod. Res., 22(10): 915-920. (Pubitemid 352044695)
9. Duyfjes BEE (1993). Stemonaceae. Flora Malesiana Ser. I, 11: 399-409.
10. Ge F, Ke C, Tang W, Yang X, Tang C, Qin G, Xu R, Li T Chen X, Zuo J and Ye Y (2007). Isolation of chlorogenic acids and their derivatives from Stemona japonica by preparative HPLC and evaluation of their anti-AIV (H5N1) activity in vitro. Phytochem. Anal., 18: 213-218. (Pubitemid 46730260)
11. Greger H (2006). Structural relationships, distribution and biological activities of Stemona alkaloids. Planta Med., 72: 99-113.
12. Götz M, Bögri T, Gray AH and Struz GM (1968). The structure of tuberostemonine. Tetrahedron, 64(6): 2631-2643.
13. Hart JH (1981). Role of phytostilbenes in decay and disease resistance. Ann. Rev. Phytopathol., 19: 437-458.
14. Herrmann KM (1995). The shikimate pathway: early steps in the biosynthesis of aromatic compounds. The Plant Cell, 7: 907-919.
15. Heywood VH (1978). Flowering plants of the world, Oxford university press, London, England.
16. Inthachub P (2008). Taxonomic revision on the family Stemonaceae in Thailand. M.S. Thesis, Kasertsart University, Bangkok, Thailand
17. Jiang R-W, Hon P-M, But PP, Chung H-S, Lin G, Ye W-C and Mak TCW (2002). Isolation and stereochemistry of two new alkaloids from Stemona tuberosa. Tetrahedron, 58: 6705-6712.
18. Jiang R-W, Hon P-M, Zhou Y, Chan Y-M, Xu Y-T, Xu H-X, Greger H, Shaw P-C and But PPH (2006a). Alkaloids and chemical diversity of Stemona tuberosa. J. Nat. Prod., 69: 749-754. (Pubitemid 44021398)
19. Jiang R-W, Hon P-M, Xu Y-T, Chan Y-M, Xu H-X, Shaw PC and But PP (2006b). Isolation and chemotaxonomic significance of tuberostemospironine-type alkaloids from Stemona tuberosa. Phytochemistry, 67: 52-57. (Pubitemid 41811247)
20. Jitjaingam A (2008). Effects of Stemona curtisii Hook.F. extract on reproduction of male albino rats. M.S. Thesis, Chiang Mai University, Chiang Mai, Thailand
21. Jiwajinda S, Hirai N, Watanabe K, Santisopasri V, Chuengsamarnyart N, Koshimizu K and Ohigashi H (2001). Occurrence of the insecticidal 16,17-didehydro- 16(E)-stemofoline in Stemona collinsae. Phytochemistry, 56: 693-695. (Pubitemid 32267725)
22. Joshi K, Chavan P, Warude D and Patwardhan B (2004). Molecular markers in herbal drug technology. Current science, 87(2): 159-165. (Pubitemid 39415116)
23. Kaltenegger E, Brem B, Mereiter K, Kalchhauser H, Kählig H, Hofer O, Vajrodaya S and Greger H (2003). Insecticidal pyrido[1,2-a]azepine alkaloids and related derivatives from Stemona species. Phytochemistry, 63: 803-816. (Pubitemid 36903594)
24. Kostecki K, Engelmeier D, Pacher T, Hofer O, Vajrodaya S and Greger H (2004). Dihydrophenanthrenes and other antifungal stilbenoids from Stemona cf. pierrei. Phytochemistry, 65: 99-106. (Pubitemid 38155896)
25. Lee KY, Sung SH and Kim YC (2006). Neuroprotective bibenzyl glycosides of Stemona tuberosa roots. J. Nat. Prod., 69: 679-681. (Pubitemid 43798127)
26. Leung PHH, Zhang L, Zuo Z and Lin G (2006). Intestinal absorption of Stemona alkaloids in a Caco-2 cell model. Planta Med., 72: 211-216.
27. Lin L-G, Zhong Q-X, Cheng T-Y, Tang C-P, Ke C-Q, Lin G and Ye Y (2006). Stemoninines from the roots of Stemona tuberosa. J. Nat. Prod., 69: 1051-1054. (Pubitemid 44252218)
28. Lin L-G, Tang C-P, Dien P-H, Xu R-S and Ye Y (2007). Cochinchistemonine, a novel skeleton alkaloid from Stemona cochinchinensis. Tetrahedron Letters, 48: 1559-1561. (Pubitemid 46195182)
29. Lin L-G, Yang X-Z, Tang C-P, Ke C-Q, Zhang J-B and Ye Y (2008a). Antibacterial stilbenoids from the roots of Stemona tuberosa. Phytochemistry, 69: 457-463.
30. Lin L-G, Li KM, Tang C-P, Ke C-Q, Rudd JA, Lin G and Ye Y (2008b). Antitussive stemoninine alkaloids from the roots of Stemona tuberosa. J. Nat. Prod., 71: 1107-1110. (Pubitemid 352008920)
31. Lin L-G, Leung HP, Zhu J-Y, Tang C-P, Ke C-Q, Rudd JA, Lin G and Ye Y (2008c). Croomine- and tuberostemoninetype alkaloids from roots of Stemona tuberosa and their antitussive activity. Tetrahedron, 64: 10155-10161.
32. Limtrakul P, Siwanon S, Yodkeeree S and Duangrat C (2007). Effect of Stemona curtisii root extract on P-glycoprotein and MRP-1 function in multidrug-resistant cancer cells. Phytomedicine, 14: 381-389. (Pubitemid 46818013)
33. Mungkornasawakul P, Pyne SG, Jatisatienr A, Supyen D, Lie W, Ung AT, Skelton BW and White AH (2003). Stemocurtisine, the first pyrido[1,2-a]azepine Stemona alkaloid. J. Nat. Prod., 66: 980-982. (Pubitemid 36909847)
34. Mungkornasawakul P, Pyne SG, Jatisatienr A, Lie W, Ung AT, Issakul K, Sawatwanich A, Supyen D and Jatisatienr C (2004a). Phytochemical studies on Stemona burkillii Prain: two new dihydrostemofoline alkaloids. J. Nat. Prod., 67: 1740-1743. (Pubitemid 39426135)
35. Mungkornasawakul P, Pyne SG, Jatisatienr A, Supyen D, Jatisatienr C, Lie W, Ung AT, Skelton BW and White AH (2004b). Phytochemical and larvicidal studies on Stemona curtisii: structure of a new pyrido[1,2-a]azepine Stemona alkaloid. J. Nat. Prod., 67: 675-677. (Pubitemid 38533944)
36. Mungkornasawakul P, Matthews H, Ung AT, Pyne SG, Jatisatienr A, Lie W, Skelton BW and White AH (2005). Confirmation of the structure of oxystemokerrin by single crystal X-ray structural analysis and a proposed biosynthesis. ACGC Chem. Res. Comm., 19: 30-33.
37. Mungkornasawakul P, Chaiyong S, Sastraruji T, Jatisatienr A, Jatisatienr J, Pyne SG, Ung AT, Korth J and Lie W (2009). Alkaloids from the roots of Stemona aphylla. J. Nat. Prod., 72: 848-851.
38. Pandee S, Sangjun N and Jatisatienr A (2003). Toxicity study of Stemona curtisii Hk.f. Thai Journal of Phytopharmacy, 10(2): 13-21.
39. Pacher T, Seger C, Engelmeier D, Vajrodaya S, Hofer O and Greger H (2002). Antifungal stilbenoids from Stemona collinsae. J. Nat. Prod., 65: 820-827. (Pubitemid 34733983)
40. Pilli RA and Ferreira de Oliveira MC (2000). Recent progress in the chemistry of the Stemona alkaloids. Nat. Prod. Rep., 17: 117-127. (Pubitemid 30097627)
41. Pilli RA, Rosso GB and Ferreira de Oliveira MC (2005). The Stemona alkaloids. In : Cordell GA (eds) The Alkaloids: Chemistry and Biology, Vol. 62, Elsevier, Amsterdam, Netherlands, pp. 77-173.
42. Pyne SG, Ung AT, Jatisatienr A and Mungkornasawakul P (2007). The pyrido[1,2-a]azepine Stemona alkaloids. Mj. Int. J. Sci. Tech., 1(2): 157-165.
43. Valkenburg JLCH and Bunyapraphatsara N (2002). Plant resources of South-East Asia, No 12 (2), Prosea foundation, Indonesia
44. Rinner B, Siegl V, Pürstner P, Efferth T, Brem B, Greger H and Pfragner R (2004). Activity of novel plant extracts against medullary thyroid carcinoma cells. Anticancer Res., 24: 495-500. (Pubitemid 38623125)
45. Rimando AM and Suh N (2008). Biological/chemopreventive activity of stilbenes and their effect on colon cancer. Planta Med., 74: 1635-1643.
46. Sastraruji K, Pyne SG, Ung AT, Mungkornasawakul P, Lie W and Jatisatienr A (2009). Structural revision of stemoburkilline from an E-alkene to a Z-alkene. J. Nat. Prod., 72: 316-318.
47. Schinnerl J, Brem B, But PP, Vajrodaya S, Hofer O and Greger H (2007). Pyrrolo-and pyridoazepine alkaloids as chemical markers in Stemona species. Phytochemistry, 68: 1417-1427. (Pubitemid 46659732)
48. Seger C, Mereiter K, Kaltenegger E, Pacher T, Greger H and Hofer O (2004). Two pyrrolo[1,2-a]azepine type alkaloids from Stemona collinsae Craib: structure elucidations, relationship to asparagamine A, and a new biogenetic concept of their formation. Chemistry & Biodiversity, 1: 265-279.
49. Smitinand T (2001). Thai plant names, The Forest Herbarium Royal, Forest Department, Bangkok, Thailand.
50. Sripanidkulchai B, Wangmaneerat A, Pongrat A, Swasdipan S, Akanitapichat P, Lerkpulsawad S and Jaksupa N (2005). The development for potential of Stemona collinsiae extracts as therapeutic agents and insecticide. Faculty of Pharmacy and Faculty of Agriculture, Ubon Ratchathani University, Ubon Ratchathani, Thailand (in Thai).
51. Vongsak B (2007). DNA fingerprint analysis of Stemona in Thailand. M.S. Thesis, Chulalongkorn University, Bangkok, Thailand.
52. Vongsak B, Kengtong S, Vajrodaya S and Sukrong S (2008). Sequencing analysis of the medicinal plant Stemona tuberosa and five related species existing in Thailand based on trnH-psbA chloroplast DNA. Planta Med., 74: 1764-1766.
53. Wang Y-Z, Tang C-P, Dien P-H and Ye Y (2007). Alkaloids from the roots of Stemona saxorum. J. Nat. Prod., 70: 1356-1359. (Pubitemid 47401581)
54. Xu Y-T, Hon P-M, Jiang R-W, Cheng L, Li S-H, Chan Y-P, Xu H-X, Shaw P-C and But PPH (2006). Antitussive effects of Stemona tuberosa with different chemical profiles. J. Ethnopharmacol., 108: 46-63.
55. Yang X-Z, Tang C-P and Ye Y (2006). Stilbenoids from Stemona japonica. J. Asian Nat. Prod. Res., 8(1-2): 47-53. (Pubitemid 43879862)
56. Yang X-Z, Lin L-G, Tang C-P, Liu Y-Q and Ye Y (2007a). Nonalkaloids constituents from Stemona japonica. Helvetica Chimica Acta, 90: 318-325.
57. Yang X-Z, Tang C-P, Ke C-Q and Ye Y (2007b). Stilbenoids from Stemona sessilifolia. J. Asian Nat. Prod. Res., 9(3): 261-266. (Pubitemid 46933334)
58. Ye Y, Qin G-W and Xu R-S (1994). Alkaloids of Stemona japonica. J. Nat. Prod., 57(5): 655-669. (Pubitemid 2104962)
59. Zhang T, Zhang Y-Z and Tao J-S (2007). Antibacterial constituents from Stemona sessilifolia. J. Asian Nat. Prod. Res., 9(5): 509-515. (Pubitemid 47265800)
60. Zhao W, Qin G, Ye Y, Xu RS and Le XF (1995). Bibenzyl from Stemona tuberosa. Phytochemistry, 38(3): 711-713.
61. Zhou X, Leung PHH, Li N, Ye Y, Zhang L, Zou Z and Lin G (2009). Oral absorption and antitussive activity of tuberostemonine alkaloids from the roots of Stemona tuberosa. Planta Med., 75: 575-580.