New caulerpenyne-derived metabolites of an Elysia sacoglossan from the South Indian coast

Molecules

Volumn 11, Issue 10, 2006, Pages 808-816

  Ciavatta, M Letizia ^a   Gresa, M Pilar Lopez ^b   Gavagnin, Margherita ^a   Manzo, Emiliano ^a   Mollo, Ernesto ^a   D'Souza, Lisette ^c   Cimino, Guido ^a  

^a CNR   (Italy)

^b UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^c NATIONAL INSTITUTE OF OCEANOGRAPHY   (India)

Author keywords

Caulerpenyne; Elysia; NMR; Sacoglossans; Sesquiterpenes

Indexed keywords

CAULERPENYNE; CAULERPIN; NAPHTHALENE DERIVATIVE; PYRAZINE DERIVATIVE; SESQUITERPENE;

ANIMAL; ARTICLE; CHEMISTRY; GASTROPOD; INDIA; ISOLATION AND PURIFICATION; METABOLISM;

ANIMALS; GASTROPODA; INDIA; NAPHTHALENES; PYRAZINES; SESQUITERPENES;

EID: 33750505697     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/11100808     Document Type: Article

References (24)

1. Jensen, K. R. A review of sacoglossan diets, with comparative notes on radular and buccal anatomy. Malacol. Rev. 1980, 13, 55-77.
2. Clark, K.B.; Busacca, M. Feeding specificity and chloroplast retention in four tropical ascoglossa, with a discussion of the extent of chloroplast symbiosis and the evolution of the order. J. Moll. Stud. 1978, 44, 272-282.
3. Marin, A.; Ros, J. Ultrastructural and ecological aspects of the development of chloroplast retention in the sacoglossan gastropod Elysia timida. J. Moll. Stud. 1993, 59, 95-104.
4. Jensen, K. R. Evolution of sacoglossans (Mollusca, Opisthobranchia) and the ecological association with their food plants. Evol. Ecol. 1997, 11, 305-335.
5. Cimino, G.; Fontana, A.; Gavagnin, M. Marine opisthobranch molluscs: chemistry and ecology in sacoglossans and dorids. Curr. Org. Chem. 1999, 3, 327-372.
6. Gavagnin, M.; Mollo, E.; Monatanaro, D.; Ortea, J., Cimino, G. Chemical studies of Caribbean sacoglossans: dietary relationships with green algae and ecological implications. J. Chem. Ecol. 2000, 26, 1563-1578.
7. Horgen, F. D.; Delos Santos, D. B.; Goetz, G.; Sakamoto, B.; Kann, Y.; Nagai, H.; Scheuer, P. J. A new depsipeptide from the sacoglossan mollusk Elysia ornata and the green alga Bryopsis species. J. Nat. Prod. 2000, 63, 152-154.
8. Becerro, M. A.; Goetz, G.; Paul, V. J., Scheuer, P. J. Chemical defenses of the sacoglossan mollusk Elysia rufescens and its host alga Bryopsis sp. J. Chem. Ecol. 2001, 27, 2287-2299.
9. Paul, V. J., Van Alstyne, K. L. Use of ingested algal diterpenoids by Elysia imedae Macnae (Opisthobranchia: Ascoglossa) as antipredator defenses. J. Exp. Mar. Biol. Ecol. 1988, 119, 15-29.
10. Gavagnin, M.; Marin, A.; Mollo, E.; Crispino, A.; Villani, G.; Cimino, G. Secondary metabolites from Mediterranean Elysioidea: origin and biological role. Comp. Biochem. Physiol. 1994, 108B, 107-115.
11. Gavagnin, M.; Spinella, A.; Marin, A.; Castelluccio, F.; Cimino, G. Polypropionates from the Mediterranean mollusk Elysia timida. J. Nat. Prod. 1994, 57, 298-304.
12. Cimino, G.; Crispino, A.; Di Marzo, V.; Gavagnin, M.; Ros, J. D. Oxytoxins, bioactive molecules produced by the marine opisthobranch mollusc Oxynoe olivacea from a diet-derived precursor. Experientia 1990, 46, 767-770.
13. Gavagnin, M.; Marin, A.; Castelluccio, F.; Villani, G.; Cimino, G. Defensive relationship between Caulerpa prolifera and its shelled sacoglossan predators. J. Exp. Mar. Biol. Ecol. 1994, 175, 197-210.
14. Fontana, A.; Ciavatta, M. L.; Mollo, E.; Naik, C. G.; Wahidulla, S.; D'Souza, L.; Cimino, G. Volvatellin, caulerpenyne-related product from the sacoglossan Volvatella sp. J. Nat. Prod. 1999, 62, 931-933.
15. Amico, V.; Oriente, G.; Piattelli, M.; Trincali, C. Caulerpenyne, an unusual sesquiterpenoid from the green alga Caulerpa prolifera. Tetrahedron Lett. 1978, 38, 3593-3596.
16. Cutignano, A.; Notti, V.; D'Ippolito, G.; Domenech Coll, A.; Cimino, G.; Fontana, A. Lipase-mediated production of defensive toxins in the marine mollusc Oxynoe olivacea. Org. Biomol. Chem. 2004, 2, 3167-3171.
17. Maiti, B. C.; Thomas, R. H.; Mahendran, M. The structure of caulerpin, a pigment from Caulerpa algae. J. Chem. Res. Synop., 1978, 126-127.
18. Schwede, J. G.; Cardellina II, J. H.; Grodi,, S. H.; James, T. R.; Blackman, A. Distribution of the pigment caulerpin in species of the green alga Caulerpa. Phytochemistry 1987, 26, 155-158.
19. Guerriero, A.; Meinesz, A.; D'Ambrosio, M.; Pietra, F. Isolation of toxic and potentially toxic sesqui- and monoterpenes from the tropical green seaweed Caulerpa taxifolia which has invaded the region of Cap Martin and Monaco. Helv. Chim. Acta 1992, 75, 689-695.
20. Guerriero, A.; Marchetti, F.; D'Ambrosio, M.; Senesi, S.; Dini, F.; Pietra, F. New ecotoxicologically and biogenetically relevant terpenes of the tropical green seaweed Caulerpa taxifolia which is invading the Mediterranean. Helv. Chim. Acta 1993, 76 855-864.
21. Guerriero, A.; Depentori, D.; D'Ambrosio, M.; Durante, M.; Dini, F.; Pietra, F. Chlorophyll-photosensitised photodegradation of caulerpenyne; a potential harmful sesquiterpenoid from tropical green seaweeds in the genus Caulerpa. J. Chem. Soc. Chem. Commun. 1994, 2083-2084.
22. Guerriero, A.; D'Ambrosio, M. Epoxycaulerpenynes: reactivity and diastereoselective and highly regioselective synthesis by dimethyldioxirane oxidation of caulerpenyne. Eur. J. Org. Chem. 1999, 1985-1990.
23. Jung, V.; Pohnert, G. Rapid wound-activated transformation of the green algal defensive metabolite caulerpenyne. Tetrahedron 2001, 57, 7169-7172.
24. Jung, V.; Thibaut, T.; Meinesz, A.; Pohnert, G. Comparison of the wound-activated transformation of caulerpenyne by invasive and non-invasive Caulerpa species of the Mediterranean. J. Chem. Ecol., 2002, 28, 2091-2104.