Research eevelopment on chemically defensive substances of opisthobranch mollusks

Shengtai Xuebao/ Acta Ecologica Sinica

Volumn 27, Issue 3, 2007, Pages 1192-1205

  Zhang, Wen ^a   Guo, Yue Wei ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Chemical defensive substance; Metabolite; Opisthobranch molluscs

Indexed keywords

ANIMALIA; GASTROPODA; MOLLUSCA; OPISTHOBRANCHIA;

EID: 46649114885     PISSN: 10000933     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (93)

1. Thompson T E. In Biology of Opisthobranch Molluscs. London: The Ray Society? 1976. Vol. 1, 6 -22.
2. Riedl R. Fauna und Flora des Mitterlmeeres. Hamburg-Berlin: Verlag Paul Parey 1983.
3. Rudman W B, Willan R C. Opisthobranchia. In: Beesley P L, Ross G J B, Wells A, eds. Mollusca: The Southern Synthesis. Fauna of Australia. Melbourne: CSIRO Publishing, Vol. 5, Part B, 1998. 915-1035.
4. Faulkner D J., Marine natural products. Natural Product Reports, 2002, 19 (1): 1-48.
5. Blunt J W, Copp B R, Munro MHG, et al. Marine natural products. Natural Product Reports, 2005, 22 (1): 15 -61.
6. Faulkner D J, Ghiselin M T. Chemical defense and evolutionary ecology of dorid nudibranchs and some other opisthobranch gastropods. Marine Ecology Progress Series. 1983, 13: 295-301.
7. Karuso P. Chemical ecology of the nudibranchs. In: Scheuer P J, ed. Bioorganic Marine Chemistry. Berlin: Springer-Verlag, 1987. Vol. 1, 31-60.
8. Cimino G, Sodano G. The chemical ecology of Mediterranean opisthobranchs. Chemica Scripta? 1989, 29: 389 -394.
9. Faulkner D J. Chemical defenses of marine molluscs. In: Paul V J. ed Ecological Roles of Marine Natural Products. Ithaca? NY: Comstock Publishing Associate. 1992. 118-163.
10. Cimino G, Sodano G. Marine Natural Products-Diversity and Biosynthesis. In: Scheuer P J. ed Topics in Current Chemistry. Berlin: Springer-Verlag. 1993, Vol. 167,77-115.
11. Cimino G, Ghiselin M T. Chemical defense and evolution in Sacoglossa Mollusca: Gastropoda: Opisthobranchia). Chemoecology, 1998, 8: 51-60.
12. Davies-Coleman M T, Garson M J. Marine polypropionates. Natural Product Reports 1998 15: 477 -493.
13. Cimino G, Ghiselin M T. Chemical defense and evolutionary trends in biosynthetic capacity among dorid nudibranchs Mollusca: Gastropoda: Opisthobranchia). Chemoecology 1999 9: 187-207.
14. Cimino G, Fontana A, Gavagnin M,. Marine opisthobranch molluscs: chemistry and ecology in sacoglossans and dorids. Current Organic Chemistry 1999 3: 327-372.
15. Cimino G, Ciavatta M L, Fontana A, et al. Chapter 15. In: Tringali C ed. Bioavtive Compounds from Natural Sources: isolation structure characterisation and biological properties. London: Taylor & Francis Ltd 2001. 577 -637.
16. Gavagnin M, Fontana A., Diterpenes from marine opisthobranch molluscs. Current Organic Chemistry 2000 4: 1201-1248.
17. Fontana A, Cimino G.; Biosynthetic studies of secondary metabolites in marine opisthobranchs. Recent Research Developments in Organic Chemistry 2001 5: 89-105.
18. Carefoot T H. Aplysia: its biology and ecology. Oceanography and Marine Biology. An Annual Review 1987 25: 167-284.
19. Yamada K, Kigoshi H. Bioactive compounds from the sea hares of two genera: Aplysia and Dotabetta. Bulletin of the Chemical Society of Japan 1997 70: 1479-1489.
20. Pettit G R, Kamano Y, Herald C L, et al. Isolation of dolastatins 10 -15 from the marine mollusk Dolabella auricularia. Tetrahedron 1993 49: 9151-9170.
21. Pettit G. R. The Dolastatins. In: Herz W Kirby G W Moore RE, et at. eds. Progress in the Chemistry of Organic natural Products. Vienna: springer-Verlag 1997. Vol. 70 1-79.
22. Pettit G R, Xu J P, Hogan F, et al. Isolation and structure of the human cancer cell growth inhibitory cyclodepsipeptide dolastatin 16. Journal of Natural Products 1997 60: 752-754.
23. Pettit G R, Xu J P, Hogan F, et al. Antineoplastic agents 369. Isolation and structure of dolastatin 17. Heterocycles 1998 47: 491-496.
24. Pettit G R, Xu J P, Williams M D, et al. Antineoplastic agents 370. Isolation and structure of dolastatin 18. Bioorganic and Medicinal Chemistry Letters 1997 7: 827-832.
25. Margolin K, Longmate J, Synold T W, et al. Dolastatin-10 in metastatic melanoma: a phase II and pharmokinetic trial of the California Cancer Consortium. Investigational New Drugs 2001 19: 335 -340.
26. Dang L H, Bettegowda C, Huso D L, et al. Combination bacteriolytic therapy for the treatment of experimental tumors. Proceedings of the National Academy of Sciences of the United States of America 2001 98: 15155-15160.
27. Ebbinghaus S W, Dunn H, Jennings L, et al. A phase I and pharmacokinetic study of the dolastatin 15 analog ILX651. Proceedings of the American Association for Cancer Research 2002 43: 552.
28. Smyth J, Boneterre M E, Schellens J, et al. Activity of the dolastatin analogue LU103793 in malignant melanoma. Annals of Oncology 2001 12: 509-511.
29. Pettit G R, Xu J-P, Doubek D L, et al. Antineoplastic Agents. 510. Isolation and structure of dolastatin 19 from the gulf of California Sea hare Dolabella auricularia. Journal of Natural Products, 2004 67: 1252 -1255.
30. Sone H Kigoshi H Yamada K Aurisides A and B cytotoxic macrolide glycosides from the Japanese Sea hare Do abe a auricu aria. Journal of Organic Chemistry 1996 61: 8956-8960.
31. Barchi J J, Jr Moore R E, Patterson G M L. Acutiphycin and 20 21-didehydroacutiphycin new antineoplastic agents from the cyanophyte Oscillatoria acutissima. Journal of the American Chemical Society 1984 106: 8193 -8197.
32. Yotsu-Yamashita M, Haddock R L, Yasumoto T. Polycavernoside A: a novel glycosidic macrolide from the red alga Polycavernosa tsudai Gracilaria edulis). Journal of the American Chemical Society 1993 115: 1147-1148.
33. Yotsu-Yamashita M, Seki T, Paul V J, et al. Four new analogs of polycavernoside. Tetrahedron Letters, 1995, 36: 5563-5566.
34. Lin G Qi Z. Opisthobranchia. In: Huang Z ed. Marin Species and Their Distributions in Chinas Sea. Beijing: China Ocean Press Publishing, 1994. 458-476.
35. Lin H W, Zhang C, Yi Y Y, et al. Studies on antineoplastic constituents from marine mollusc sea hare I). Chinese Journal of Marine Drugs, 2001, 20 (3): 3-6.
36. Lin H W, Tang H F, Liu G L, et al. Studies on antineoplastic constituents from marine mollusc sea hare (II). Academic Journal of Second Military Medical University, 2002, 23: 243-245.
37. Ortega M J, Zubia E, Salvd J. New polyhalogenated monoterpenes from the sea hare Aplysia punctata. Journal of Natural Products, 1997, 60: 482-484.
38. 14C incoporation into metabolites of the saccoglossan Placobranchus ocellatus. Science 1979 205: 922-923.
39. Fu X, Hong E P, Schmitz F J. New polypropionate pyrones from the Philippine sacoglossan mollusc P acobranchus oce atus. Tetrahedron, 2000, 56: 8989-8993.
40. Ireland C, Faulkner D J. The metabolites of the marine molluscs tridachiella diomedea and tridachia crispate. Tetrahedron, 1981, 37: 233-240.
41. Gavagnin M, Spinella A, Castelluccio F, et al. Polypropionates from the Mediterranean mollusk Elysia timida. Journal of Natural Products, 1994, 57: 298-304.
42. Gavagnin M, Mollo E, Cimino G, et al. A new-y-dihydropyrone-propionate from the Caribbean sacoglossan Tridachia crispate. Tetrahedron Letters, 1996, 37: 4259-4262.
43. Gavagnin M, Mollo E, Castelluccio F, et al. A novel dietary sesquiterpene from the marine sacoglossan Tridachia crispate. Natural Product Letters, 1997. 10: 151-156.
44. Gosliner T M ed. Nudibranch of Southern Africa, A guide to the opisthobranch molluscs of Southern Africa. Monterey, California:Sea challengers, 1987. 109-112.
45. Pika J, Faulkner D J. Four sesquiterpenes from the South African nudibranch Leminda millecra. Tetrahedron, 1994, 50: 3065-3070.
46. McPhail K L, Davies-Coleman M T, Starmer J. Sequestered chemistry of the arminacean nudibranch Leminda millecra in Algoa Bay, South Africa. Journal of Natural Products, 2001, 64: 1183-1190.
47. Nagashima F, Momosaki S, Watanabe Y, et al. Sesquiterpenoids from the liverworts Bazzania trilobata and Porella canariensis. Phytochemistry, 1996, 42: 1361-1366.
48. Warmers U, Konig W A. Sesquiterpene constituents of the liverwort Bazzania trilobata. Phytochemistry, 1999, 52: 99-104.
49. Weinheimer A J, Schmitz F J, Ciereszko L S. The occurrence of terpenoid compounds in gorgonians. In: Freudenthal H D ed. Transactions of the Drugs from the Sea Symposium. Washington, D C-Marine Technology Society, 1967. 135-140.
50. Kashman Y. 8-Methoxy and 5-hydroxy-8-methoxy-calamenenes from the marine gorgonian Subergorgia hicksoni. Tetrahedron, 1979, 35: 263-266.
51. Bowden B F, Braekman J C, Coll J C, et al. Studies of Australian soft corals XX. A new sesquiterpene furan from soft corals of the family Xeniidae and an examination of Clavularia inflata from North Queensland waters. Australian Journal of Chemistry, 1980, 33: 927-932.
52. Chan W R, Tinto W F, Moore R. New germacrane derivatives from gorgonian octocorals of the genus Pseudoptergorgia. Tetrahedron, 1990, 46: 1499-1502.
53. Karuso P, Scheuer P J. Natural products from three nudibranchs: Nembrotha kubaryana, Hypselodoris infucata and Chromodoris petechialis. Molecules, 2002, 7: 1 -6.
54. Gavagnin M, Ungur N, Castelluccio F, et al. New minor diterpenoid diacylglycerols from the skin of the nudibranch Anisodoris fontaini. Journal of Natural Products, 1999, 62: 269-274.
55. Gavagnin M, Ungur N, Castelluccio F, Cimino G. Novel verrucosins from the skin of the Mediterranean nudibranch Doris verrucosa. Tetrahedron,1997, 53: 1491-1504.
56. Zubia E, Gavagnin M, Crispino A, et al. Diasteroisomeric ichthyotoxic acylglycerols from the dorsum of two geographically distinct populations of Archidoris nudibranchs. Experientia, 1993, 49: 268-271.
57. Graziani E I, Andersen R J, Krug P J, et al. Stable isotope incorporation evidence for the de novo biosynthesis of terpenoic acid glycerides by dorid nudibranchs. Tetrahedron, 1996, 52: 6869-6878.
58. Gavagnin M, De Napoli A, Castelluccio F, et al. Austrodorin-A and-B: first tricyclic diterpenoid 2-monoglyceryl esters from an Antarctic nudibranch. Tetrahedron Letters, 1999, 40: 8471-8475.
59. Gavagnin M, De Napoli A, Cimino G, et al. Absolute configuration of diterpenoid diacylglycerols from the Antarctic nudibranch Austrodoris kerguelenensis. Tetrahedron: Asymmetry, 1999, 10: 2647-2650.
60. Gavagnin M, Carbone M, Mollo E, et al. Further chemical studies on the Antarctic nudibranch Austrodoris kerguelenensis: new terpenoid acylglycerols and revision of the previous stereochemistry. Tetrahedron, 2003, 59: 5579-5583.
61. Nakamura H, Wu H, Ohizumi Y, et al. Agelasine-A,-B,-C and-D, novel bicyclic diterpenoids with a 9-methyladeninium unit possessing inhibitory effects on na,K-atpase from the okinawa sea sponge Agelas sp. Tetrahedron letters, 1984, 25: 2989-2992.
62. Gavagnin M, Carbone M, Mollo E, et al. Austrodoral and austrodoric acid: nor-sesquiterpenes with a new carbon skeleton from the Antarctic nudibranch Austrodoris kerguelenensis. Tetrahedron Letters, 2003, 44: 1495-1498.
63. Fontana A, Cavaliere P, Wahidulla S, et al. A new antitumor isoquinoline alkaloid from the marine nudibranch Jorunna funebris. Tetrahedron, 2000, 56: 7305-7308.
64. Rogers D J, Paul V J. Chemical deferences of three Glossodoris nudibranchs and their dietary Hyrtios sponges. Marine Ecology Progress Series, 1991, 77: 221-232.
65. Avila C, Paul V J. Chemical ecology of the nudibranch Glossodoris pallida: is the location of dietderived metabolites important for defense? Marine Ecology Progress Series, 1997, 150: 171-180.
66. Fontana A, Cavaliere P, Ungur N, et al. New scalaranes from the nudibranch Glossodoris atromarginata and Its Sponge Prey. Journal of Natural Products, 1999, 62: 1367-1370.
67. Fontana A, Mollo E, Ortea J, et al. Scalarane and homoscalarane compounds from the nudibranchs Glossodoris sedna and Glossodoris dalli: chemical and biological properties.Journal of Natural Products, 2000, 63: 527-530.
68. Gavagnin M, Mollo E, Docimo T, et al. Scalarane metabolites of the nudibranch Glossodoris mfomarginata and its dietary sponge from the South China Sea. Journal of Natural Products 2004 67: 2104-2107.
69. Terem B, Scheuer P J. Scalaradial derivatives from the nudibranch Chromodoris joungbleuthi and the sponge Spongia Oceania. Tetrahedron 1986 42: 4409-4412.
70. Miyamoto T, Sakamoto K, Amano H, et al. New cytotoxic sesterterpenoids from the nudibranch Chromodoris inornata. Tetrahadron 1999 55: 9133-9142.
71. Hirota H, Okino T, Yoshimura E, et al. Five new antifouling sesquiterpenes from two marine sponges of the genus Axinjssa and the nudibranch Phjllidia pustulosa. Tetrahedron 1998 54: 13971-13980.
72. Gulavita N K, de Silva E D, Hagadone M R, et al. Nitro genous bisabolene sesquiterpenes from marine invertebrates. Journal of Organic Chemistry 1986 51: 5136-5139.
73. Fusetani N, Wolstenholme H J, Matsunaga S, et al. Two new sesquiterpene isonitriles from the nudibranch, phjllida, pustulosa. Tetrahedron Letters 1991 32: 7291-7294.
74. Kassuhlke K E, Potts B C M, Faulkner D J. New nitrogenous sesquiterpenes from two Philippine nudibranchs, Phjllidia pustulosa and P.varicose, and from a Palauan sponge, Halichondria cf. lendenfeldi. Journal of Organic Chemistry 1991 56: 3747-3750.
75. Wright A D. GC-MS and NMR analysis of Phjllidiella pustulosa and one of its dietary sources, the sponge Phakellia carduus. Comparative Biochemistry & Physiology 2003 134A: 307-313.
76. Dumdei E J, Flowers A E, Garson M J, et al. The Biosynthesis of sesquiterpene isocyanides and isothiocyanates in the marine sponge Acanthe a Cavernosa Dendy)evidence for dietary transfer to the dorid nudibranch Phjllidiella Pustulosa. Comparative Biochemistry & Physiology 1997 118 A: 1385-1392.
77. Manzo E, Ciavatta M L, Gavagnin M, et al. Isocyanide terpene metabolites of Phjllidiella pustulosa a nudibranch from the South China Sea. Journal of Natural Products 2004, 67: 1701-1704.
78. Fusetani N, Yasumuro K, Kawai H, et al. Kalihinene and isokalihinol B, cytotoxic diterpene isonitriles from the marine sponge Acanthe a k ethra. Tetrahedron Letters 1990, 31: 3599-3602.
79. Chang C W J, Patra A, Roll D M, et al. Kalihinol-A a highly functionalized diisocyano diterpenoid antibiotic from a sponge. Journal of the American Chemical Society 1984, 106: 4644-4646.
80. Patra A, Chang C W J, Scheuer P J, et al. An unprecedented triisocyano diterpenoid antibiotic from a sponge. Journal of the American Chemical Society 1984, 106: 7981-7983.
81. Chang C W J, Patra A, Baker J A, et al. Kalihinols multifunctional diterpenoid antibiotics from marine sponges Acanthe a spp. Journal of the American Chemical Society 1987, 109: 6119-6123.
82. Shimomura M, Miyaoka H, Yamada Y. Absolute configuration of marine diterpenoid kalihinol. Tetrahedron Letters, 1999, 40: 8015-8017.
83. Yan X H, Song G Q, Zhou X-H, et al. Studies on the chemical constituents of marine sponge Acanthella sp. from the South China Sea. Natural Product Research & Development 2003, 15: 199-202.
84. Wratten S J, Faulkner D J, Hirotsu K, et al. Diterpenoid isocyanides from the marine sponge hjmeniacidon amphi ecta. Tetrahedron Letters 1978,19: 4345-4348.
85. Ciavatta M L, Fontana A, Puliti R, et al. Structures and absolute stereochemistry of isocyanide and isothiocyanate amphilectenes from the Caribbean sponge Cribochalina sp. Tetrahedron 1999, 55: 12629-12636.
86. Okino T, Yoshimura E, Hirota H, et al. Antifouling kalihinenes from the marine sponge Acanthe a cavernosa. Tetrahedron Letters 1995 36: 8637-8640.
87. Okino T, Yoshimura E, Hirota H, et al. New Antifouling kalihipyrans from the marine sponge Acanthe a cavernosa. Journal of Natural Products 1996, 59: 1081-1083.
88. Hirota H, Tomono Y, Fusetani N. Terpenoids with antifouling activity against barnacle larvae from the marine sponge Acanthe a cavernosa. Tetrahedron 1996, 52: 2359-2368.
89. Yasman, Edrada R A, Wray V, et al. New 9-thiocyanatopupukeanane sesquiterpenes from the nudibranch Phjllidia varicosa and its sponge-prey Axinjssa aculeate. Journal of Natural Products 2003, 66: 1512 -1514.
90. Tanaka J, Higa T. Two new cytotoxic carbonimidic dichlorides from the nudibranch Reticulidia fungia. Journal of Naural Products 1999, 62: 1339-1340.
91. Wratten S J, Faulkner D J, Van Engen D, et al. A vinyl carbonimidic dichloride from the marine sponge Pseudaxinjssa pitjs. Tetrahedron Letters 1978, 19: 1391-1394.
92. Wratten S J, Faulkner D J. Minor carbonimidic dichlorides from the marine sponge Pseudaxinjssa pitjs. Tetrahedron Letters 1978, 19: 1395-1398.
93. Simpson J S, Raniga P, Garson M J. Biosynthesis of dichloroimines in the tropical marine sponge stj ote a aurantium. Tetrahedron Letters 1997, 38: 7947-7950.