Structural relationships, distribution and biological activities of Stemona alkaloids

Planta Medica

Volumn 72, Issue 2, 2006, Pages 99-113

  Greger, Harald ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Bioactivity; Croomia; Pyrrolo 1,2 a azepine alkaloids; Stemona; Stemona alkaloids; Stichoneuron; Structural diversity

Indexed keywords

ALKALOID DERIVATIVE; AZEPINE DERIVATIVE; CROOMINE DERIVATIVE; NEOTUBEROSTEMONINE; PARVISTEMOLINE; PLANT EXTRACT; PROTOSTEMOMINE DERIVATIVE; PROTOSTEMONINE DERIVATIVE; PYROLLO[1,2 A]AZEPINE; STEMOFOLINE; STEMONININE; STERMONA EXTRACT; STICHONEURINE DERIVATIVE; TUBEROSTEMONINE; UNCLASSIFIED DRUG;

ARMYWORM; ASTHMA; CHINESE MEDICINE; COUGHING; DRUG ACCUMULATION; DRUG DISTRIBUTION; DRUG MECHANISM; DRUG STRUCTURE; HELMINTH; INSECTICIDAL ACTIVITY; NEUROMUSCULAR SYNAPSE; NONHUMAN; REVIEW; STEMONACEAE; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; TOXICITY;

ALKALOIDS; ANIMALS; ANTITUSSIVE AGENTS; INSECTICIDES; LARVA; PLANT EXTRACTS; PLANT ROOTS; SPODOPTERA; STEMONACEAE; STRUCTURE-ACTIVITY RELATIONSHIP;

ASTACOIDEA; CAVIA PORCELLUS; CROOMIA; INSECTA; SPODOPTERA LITTORALIS; STEMONA; STEMONACEAE; STICHONEURON; VERMES;

EID: 33644537939     PISSN: 00320943     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-916258     Document Type: Review

References (73)

1. Pilli RA, Ferreira de Oliveira MC. Recent progress in the chemistry of the Stemona alkaloids. Nat Prod Rep 2000; 17: 117-27
2. Xu RS. Some bioactive natural products from Chinese medicinal plants. In: Atta-ur-Rahman, editor. Studies in natural products chemistry; Vol. 21 Amsterdam: Elsevier Science BV, 2000: 729-72
3. Stöger EA. Arzneibuch der Chinesischen Medizin. Monographien des Arzneibuches der Volksrepublik China 1990 und 1995. Stuttgart: Deutscher Apotheker Verlag, 1999: 1-6
4. Taguchi H, Kanchanapee P, Amatayakul T. The constituents of Clitoria macrophylla Wall. Cat., a Thai medicinal plant. The structure of a new rotenoid, clitoriacetal. Chem Pharm Bull 1977; 25: 1026-30
5. Shiengthong D, Donavanik T, Uaprasert V, Roengsumran S, Massy-Westropp RA. Constituents of Thai medicinal plants - III. New rotenoid compounds - stemonacetal, stemonal and stemonone. Tetrahedron Lett, 1974: 2015-8
6. Brem B, Seger C, Pacher T, Hofer O, Vajrodaya S, Greger H. Feeding deterrence and contact toxicity of Stemona alkaloids - a source of potent natural insecticides. J Agric Food Chem 2002; 50: 6383-8
7. Pacher T, Seger C, Engelmeier D, Vajrodaya S, Hofer O, Greger H. Anti-fungal stilbenoids from Stemona collinsae. J Nat Prod 2002; 65: 820-7
8. Sekine T, Ikegami F, Fukasawa N, Kashiwagi Y, Aizawa T, Fujii Y et al. Structure and relative stereochemistry of a new polycyclic alkaloid, asparagamine A, showing anti-oxytocin activity, isolated from Asparagus racemosus. J Chem Soc Perkin Trans 1 1995: 391-3
9. Wiboonpun N, Phuwapraisirisan P, Tip-Pyang S. Identification of anti-oxidant compound from Asparagus racemosus. Phytother Res 2004; 18: 771-3
10. Irie H, Masaki N, Ohno K, Osaki K, Taga T, Uyeo S. The crystal structure of a new alkaloid, stemofoline, from Stemona japonica. Chem Commun, 1970: 1066
11. Jiwajinda S, Hirai N, Watanabe K, Santisopasri V, Chuengsamarnyart N, Koshimizu K et al. Occurrence of the insecticidal 16,17-didehydro-16(E)- stemofoline in Stemona collinsae. Phytochemistry 2001; 56: 693-5
12. Seger C, Mereiter K, Kaltenegger E, Pacher T, Greger H, Hofer O. 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. Chem Biodivers 2004; 1: 265-79
13. Cong XD, Xu GJ, Jin RL, Zhi HJ. Pharmacognostical studies on Baibu radix Stemonae and allied drugs IX. Determination and evaluation of total alkaloid content in the roots of Chinese Stemona spp. Acta Pharm Sin 1992; 27: 556-60
14. Sekine T, Fukasawa N, Murakoshi I, Ruangrungsi N. A 9,10- dihydrophenanthrene from Asparagus racemosus. Phytochemistry 1997; 44: 763-4
15. Kostecki K, Engelmeier D, Pacher T, Hofer O, Vajrodaya S, Greger H. Dihydrophenanthrenes and other antifungal stilbenoids from Stemona cf. pierrei. Phytochemistry 2004; 65: 99-106
16. Duyfjes BEE. Stemonaceae. Flora Malesiana Ser 1 1993; 11: 399-409
17. Ji ZH, Duyfjes BEE. Stemonaceae. In: Wu ZY, Raven PH, editors. Flora of China; Vol. 24 Beijing: Science Press, 2000: 70-2
18. Telford IRH. In: George AS, editor. Flora of Australia; Vol. 46 Canberra: Australian Government Publishing Service, 1986: 177-80
19. Wipf P, Rector SR, Takahashi H. Total synthesis of (-)-tuberostemonine. J Am Chem Soc 2002; 124: 14848-9
20. Brüggemann M, McDonald AI, Overman LE, Rosen MD, Schwink L, Scott JP. Total synthesis of (±)-didehydrostemofoline (asparagamine A) and (±)-isodidehydrostemofoline. J Am Chem Soc 2003; 125: 15284-5
21. Alibés R, Blanco P, Casas E, Closa M, de March P, Figueredo M et al. Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids. J Org Chem 2005; 70: 3157-67
22. Noro T, Fukushima S, Ueno A, Miyase T, Iitaka Y, Saiki Y. A new alkaloid, croomine, from Croomia heterosepala Okuyama. Chem Pharm Bull 1979; 27: 1495-7
23. Schinnerl J, Kaltenegger E, Pacher T, Vajrodaya S, Hofer O, Greger H. New pyrrolo[1,2-a]azepine type alkaloids from Stemona and Stichoneuron (Stemonaceae). Monatsh Chem 2005; 136: 1671-80
24. Ye Y, Qin GW, Xu RS. Alkaloids of Stemona japonica. J Nat Prod 1994; 57: 665-9
25. Sakata K, Aoki K, Chang CF, 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
26. Terada M, Sano M, Ishii AI, Kino H, Fukushima S, Noro T. Studies on chemotherapy of parasitic helminths (III). Effects of tuberostemonine from Stemona japonica on the motility of parasitic helminths and isolated host tissues. Nippon Yakurigaku Zasshi 1982; 79: 93-103
27. Prucksunand C, Khunawat P, Wimolwattanapun S, Prucksunand P. The effect of "Non-Tai-Yak" (Stemona curtisii) on the action potential of isolated frog sciatic nerve. A preliminary report. J Med Assoc Thailand 1985; 68: 66-71
28. Shinozaki H, Ishida M. Inhibitory actions of tuberostemonine on the excitatory transmission at the crayfish neuromuscular junction. Brain Res 1985; 334: 33-40
29. Kaltenegger E, Brem B, Mereiter K, Kalchhauser H, Kählig HP, Hofer O et al. Insecticidal pyrido[1,2-a]azepine alkaloids and related derivatives from Stemona species. Phytochemistry 2003; 63: 803-16
30. Brem B, Seger C, Pacher T, Hartl M, Hadacek F, Hofer O et al. Antioxidant dehydrotocopherols as a new chemical character of Stemona species. Phytochemistry 2004; 65: 2719-29
31. Götz M, Strunz GM. Tuberostemonine and related compounds: the chemistry of the Stemona alkaloids. In: Wiesner K, editor. MTB international review of sciences, organic chemistry series one; Vol 9 London: Butterworth, 1973: 143-60
32. Ye Y, Qin GW, Xu RS. Alkaloids from Stemona tuberosa. Phytochemistry 1994; 37: 1201-3
33. Ye Y, Qin GW, Xu RS. Alkaloids of Stemona japonica. Phytochemistry 1994; 37: 1205-8
34. Lin WH, Fu HZ. Three new alkaloids from the roots of Stemona tuberosa Lour. J Chin Pharm Sci 1999; 8: 1-7
35. Irie H, Harada H, Ohno K, Mizutani T, Uyeo S. The structure of the alkaloid protostemonine. Chem Commun, 1970: 268-9
36. Schild H. Über ein Alkaloid der Stemona sessilifolia. Ber Dtsch Chem Ces 1936; 69: 74-80
37. Götz M, Bögri T, Gray AH, Strunz GM. The structure of tuberostemonine. Tetrahedron 1968; 24: 2631-43
38. Kakuta D, Hitotsuyanagi Y, Matsuura N, Fukaya H, Takeya K. Structures of new alkaloids sessilifoliamides A-D from Stemona sessilifolia. Tetrahedron 2003; 59: 7779-86
39. Zou CY, Fu HZ, Lei HM, Li J, Lin WH. New alkaloids from the roots of Stemona japonica Miq. J Chin Pharm Sci 1999; 8: 185-9
40. Edwards OE, Feniak G, Handa KL. The alkaloids of Stemona sessilifolia. Can J Chem 1962; 40: 455-62
41. Lin WH, Ye Y, Xu RS. Chemical studies on new Stemona alkaloids, IV. Studies on new alkaloids from Stemona tuberosa. J Nat Prod 1992; 55: 571-6
42. Jiang RW, Hon PM, But PPH, Chung HS, Lin G, Ye WC et al. Isolation and stereochemistry of two new alkaloids from Stemona tuberosa. Tetrahedron 2002; 58: 6705-12
43. Pham HD, Yu BW, Chau VM, Ye Y, Qin GW. Alkaloids from Stemona collinsae. J Asian Nat Prod Res 2002; 4: 81-5
44. Mungkornasawakul P, Pyne SG, Jatisatienr A, Lie W, Ung AT, Issakul K et al. Phytochemical studies on Stemona burkillii Prain: two new dihydrostemofoline alkaloids. J Nat Prod 2004; 67: 1740-3
45. Mungkornasawakul P, Pyne SG, Jatisatienr A, Supyen D, Lie W, Ung AT et al. Stemocurtisine, the first pyrido[1,2-a]azapine Stemona alkaloid. J Nat Prod 2003; 66: 980-2
46. Mungkornasawakul P, Pyne SG, Jatisatienr A, Supyen D, Jatisatienr C, Lie W et al. Phytochemical and larvicidal studies on Stemona curtisii: structure of a new pyrido[1,2-a]azepine Stemona alkaloid. J Nat Prod 2004; 67: 675-7
47. Lin WH, Cai MS, Ying BP, Feng R. Studies on the chemical constituents of Croomia japonica Miq. Acta Pharm Sin 1993; 28: 202-6
48. 1H NMR line-broadening effect. Tetrahedron 1982; 38: 2667-70
49. Cheng DL, Guo J, Chu TT, Röder E. A study of Stemona alkaloids, III. Application of 2D-NMR spectroscopy in the structure determination of stemoninine. J Nat Prod 1988; 51: 202-11
50. 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 Chem Commun, 1973: 125-6
51. Lin WH, Ye Y, Xu RS. Studies on new alkaloids of Stemona mairei. Youji Huaxue 1991; 11: 500-3
52. Lin WH, Ye Y, Xu RS. Studies on new alkaloids of Stemona mairei. Chin Chem Lett 1991; 2: 369-70
53. Cong XD, Zhao HR, Guillaume D, Xu GJ, Lu Y, Zheng Q. Crystal structure and NMR analysis of the alkaloid protostemotinine. Phytochemistry 1995; 40: 615-7
54. Schinnerl J. Verbreitung und Variation charakteristischer Alkaloidprofile in der Gattung Stemona und ihre chemosystematische Bedeutung [master thesis]. Vienna: University of Vienna, 2006
55. Pham HD, Phan VK, Chau VM. Chiet tach va thu hoat tinh sinh hoc cua mot so ancaloit tu eu Bach Bo dung Stemona saxorum Gagnep. (Stemonaceae). J Chem Appl (Hoa Hoc & Ung Dung) 2002; 9: 16-20
56. Xu RS, Tang ZJ, Feng SC, Yang YP, Lin WH, Zhong QX et al. Studies on bioactive components from Chinese medicinal plants. Mem Inst Oswaldo Cruz 1991; 86 Suppl. 2: 55-9
57. Lin WH, Xu RS, Zhong QX. Chemical studies on Stemona alkaloids. II. Studies on the minor alkaloids of Stemona parviflora Wright C. H. Acta Chim Sin 1991; 49: 1034-7
58. Lin WH, Yin BP, Tang ZJ, Xu RS. The structure of parvistemonine. Acta Chim Sin 1990; 48: 811-4
59. Lin WH, Xu RS, Zhong QX. Chemical studies on Stemona alkaloids. I. Studies on new alkaloids of Stemona parviflora Wright C. H. Acta Chim Sin 1991; 49: 927-31
60. Ke CQ He ZS, Yang YP, Ye Y. A novel alkaloid from Stemona parviflora. Chin Chem Lett 2003; 14: 173-5
61. Kondo H, Satomi M, Kaneko T. Tuberostemonine 10. Separation of oxotuberostemonine and neutral substance of m. p. 178-179 . Studies on Stemona alkaloids XXIII. Ann Rep ITSUU Lab 1958; 9: 99-107
62. Pham HD, Phan VK, Luu VC, Chau VM. Alkaloids from Vietnamese Stemona tuberosa Lour. (Stemonaceae) Part 1: neotuberostemonine, bisdehydroneotuberostemonine. J Chem (Tap chi Hoa Hoc) 2000; 38: 64-7
63. Chung HS, Hon PM, Lin G, But PPH, Dong H. Antitussive activity of Stemona alkaloids from Stemona tuberosa. Planta Med 2003; 69: 914-20
64. Lin WH, Ma L, Cai MS, Barnes RA. Two minor alkaloids from roots of Stemona tuberosa. Phytochemistry 1994; 36: 1333-5
65. Cui YX, Lin WH. 2D NMR studies on tuberostemoenone and tuberostemonone. Chin J Magn Reson 1998; 15: 515-20
66. Liu SW, Fu HZ, Lin WH. Alkaloids from the roots of Stemona tuberosa. Acta Pharm Sin 1999; 34: 372-5
67. Guo J. A study of Stemona alkaloids II. Acta Chim Sin 1981; 39: 865-8
68. Pharmacopoeia of the Peoples Republic of China; Vol. 1 English Edition Beijing: Chemical Industry Press, 2000: 199-200
69. Chou PS. A preliminary study on the effectiveness of Stemona japonica in insect control. Acta Entomol Sin 1953; 2: 166-89
70. Burkill IH. A dictionary of economic products of the Malay Peninsula; Vol. 2 Kuala Lumpur: Governments of Malaysia and Singapur by the Ministry of Agriculture and Co-operatives, 1966: 2110
71. 3H]MK801 binding to synaptic membranes from rat central nervous system. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol 1994; 107: 105-10
72. Liao JF, Shi CC, Chen SY, Fu YT, Chen CF. Spasmolytic effect of water extract of Stemonae radix on the guinea-pig tracheal smooth muscle in vitro. J Ethnopharmacol 1997; 57: 57-62
73. Rinner B, Siegl V, Pürstner P, Efferth T, Brem B, Greger H et al. Activity of novel plant extracts against medullary thyroid carcinoma cells. Anticancer Res 2004; 24: 495-500