Skip to main content
SpringerLink
Log in

Chemical Diversity in Opisthobranch Molluscs from Scarcely Investigated Indo-Pacific Areas

  • Chapter
Molluscs

Part of the book series: Progress in Molecular and Subcellular Biology ((MMB,volume 43))

Abstract

Opisthobranch molluscs with both a rich variety of secondary metabolites and great biomedical potential represent the most intensively studied group of molluscs in natural product chemistry. We review here the chemical investigations into secondary metabolites of “sea slugs” from less-studied Indian, Chinese and Egyptian coasts, giving an overview of their most relevant biological activities. In addition to the biomedical interest of the metabolites, in which both structures and organisms often lose their own importance, this chapter emphasizes the phyletic and geographic distribution of the compounds in order to provide a further informational base for chemotaxonomical generalizations.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.00
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Amico V, Oriente G, Piattelli M, Tringali C, Fattorusso E, Magno S, Mayol L (1978) Caulerpenyne, an unusual sequiterpenoid from the green alga Caulerpa prolifera. Tedrahedron Lett 38:3593–3596

    Google Scholar 

  • Amico V, Caccamese S, Neri P, Russo G, Foti M (1991) Brasiliane-type sesquiterpenoids from the Mediterranean red alga Laurencia obtusa. Phytochemistry 30:1921–1927

    CAS  Google Scholar 

  • Appleton DR, Sewell MA, Berridge MV, Copp BR (2002) A new active malyngamide from a New Zealand collection of the sea hare Bursatella leachii. J Nat Prod 65:630–631

    PubMed  CAS  Google Scholar 

  • Bhosale SH, Jagtap TG, Naik CG (1999) Antifungal activity of some marine organisms from India against food spoilage Aspergillus strains. Mycopathologia 147:133–138

    PubMed  CAS  Google Scholar 

  • Bobzin SC, Faulkner DJ (1989a) Novel rearranged spongian diterpenes from the Palauan sponge Dendrilla sp.: reassessment of the structures of dendrillolide A and dendrillolide B. J Org Chem 54:5727–5731

    CAS  Google Scholar 

  • Bobzin SC, Faulkner DJ (1989b) Diterpenes from the marine sponge Aplysilla polyrhaphis and the dorid nudibranch Chromodoris norrisi. J Org Chem 54:3902–3907

    CAS  Google Scholar 

  • Cambie RC, Craw PA, Stone MJ, Bergquist PR (1988) Chemistry of sponges, IV. Spongian diterpenes from Hyatella intestinalis. J Nat Prod 51:293–297

    CAS  Google Scholar 

  • Cameron GM, Stapleton BL, Simonsen SM, Brecknell DJ, Garson MJ (2000) New sesquiterpene and brominated metabolites from the tropical marine sponge Dysidea sp. Tetrahedron 56:5247–5252

    CAS  Google Scholar 

  • Capon RJ, Ghisalberti EL, Jefferies PR (1982) New tetrahydropyrans from a marine sponge. Tetrahedron 38:1699–1703

    CAS  Google Scholar 

  • Carmely S, Cojocaru M, Loya Y, Kashman Y (1988) Two new rearranged spongian diterpenes from two Dysidea species. J Org Chem 53:4801–4807

    CAS  Google Scholar 

  • Carter TE, Rinehart LK Jr, Lin LH, Kuentzl SL, Connor JL (1978) Brominated metabolites from Laurencia brongniartii. Tetrahedron Lett 19:4479–4482

    Google Scholar 

  • Chang CWJ, Patra A, Deborah MR, Scheuer PJ (1984) Kalihinol – a, a highly functionalized diisocyanoditerpenoid antibiotic from a sponge. J Am Chem Soc 106:4644–4646

    CAS  Google Scholar 

  • Chang CWJ, Patra JA, Baker JA, Scheuer PJ (1987) Kalihinols, multifunctional diterpenoid antibiotics from marine sponges Acanthella spp. J Am Chem Soc 109:6119–6123

    CAS  Google Scholar 

  • Charles C, Braekman JC, Daloze D, Tursch B, Declercq JP, Germain G, Van Meerssche M (1978). Chemical studies of marine invertebrates. XXXIV. Herbadysidolide and herbasolide, two unusual sesquiterpenoids from the sponge Dysidea herbacea. Bull Soc Chim Belg 87:481–486

    CAS  Google Scholar 

  • Ciavatta ML, Fontana A, Puliti R, Scognamiglio G, Cimino G (1999) Structures and absolute stereochemistry of isocyanide and isothiocyanate amphilectenes from the Caribbean sponge Cribochalina sp. Tetrahedron 55:12629–12636

    CAS  Google Scholar 

  • Cimino G, Ghiselin MT (1998) Chemical defense and evolution in the Sacoglossa (Mollusca: Gastropoda: Opisthobranchia). Chemoecology 8:51–60

    CAS  Google Scholar 

  • Cimino G, Ghiselin MT (1999) Chemical defense and evolutionary trends in biosynthetic capacity among dorid nudibranch (Mollusca: Gastropoda: Opisthobranchia). Chemoecology 9:187–207

    CAS  Google Scholar 

  • Cimino G, Ghiselin MT (2001) Marine natural products chemistry as an evolutionary narrative. In: McClintock JB, Baker BJ (eds) Marine chemical ecology. CRC Press, Washington, D.C., pp. 115–156

    Google Scholar 

  • Cimino G, De Stefano S, Minale L (1973) Deoxoscalarin, a further sesterterpene with unusual tetracyclic carbon skeleton of scalarin, from Spongia officinalis. Experientia 29:934–936

    Google Scholar 

  • Cimino G, De Stefano S, Minale L (1974) Scalaradial, a third sesterterpene with a tetracarbocyclic skeleton from the sponge Cacospongia mollior. Experientia 30:846–847

    Google Scholar 

  • Cimino G, De Stefano S, Guerriero A, Minale L (1975) Furanosesquiterpenoids in sponges – III. Pallescensins A–D from Disidea pallescens: new skeletal types. Tetrahedron Lett 17:1425–1428

    Google Scholar 

  • Cimino G, Crispino A, Gavagnin M, Sodano G (1990). Diterpenes from the nudibranch Chromodoris luteorosea. J Nat Prod 53:102–106

    CAS  Google Scholar 

  • Cimino G, Passeggio A, Sodano G, Spinella A, Villani G (1991) Alarm pheromones from the Mediterranean opisthobranch Haminoea navicula. Experientia 47:61–63

    CAS  Google Scholar 

  • Cimino G, Fontana A, Gavagnin M (1999) Marine opisthobranch molluscs: chemistry and ecology in sacoglossan and dorids. Curr Org Chem 3:327–372

    CAS  Google Scholar 

  • Cimino G, Ciavatta ML, Fontana A, Gavagnin M (2001a) Metabolites of marine opisthobranchs: chemistry and biological activity. In: Tringali C (ed) Bioactive compounds from natural sources – isolation, characterization and biological properties. Taylor & Francis, London, pp. 579–637

    Google Scholar 

  • Cimino G, Fontana A, Garcia Gravalos D, Wahidulla S (2001b) New antitumor marine alkaloids WO 2001019824 A2 2001032 WO 2000-GB3489 20000911. PCT Int Appl 2001:1–9

    Google Scholar 

  • Cimino G, Fontana A, Cutignano A, Gavagnin M (2004) Biosynthesis in opisthobranch molluscs: general outline in the light of recent use of stable isotopes. Phytochem Rev 3:285–307

    CAS  Google Scholar 

  • De Silva ED, Gulavita NK (1988) Isoquinolinequinones from a marine sponge Xestospongia sp. and the nudibranch Jorunna funebris. IUPAC Int Symp Chem Nat Prod 16:610

    Google Scholar 

  • De Silva ED, Scheuer PJ (1982) Furanoditerpenoids from the dorid nudibranch Casella atromarginata. Heterocycles 17:167–170

    Google Scholar 

  • De Silva ED, Morris SA, Miao S, Dumdei E, Andersen R (1991) Terpenoid metabolites from the skin extracts of four Sri Lankan nudibranchs in the genus Chromodoris. J Nat Prod 54:993–997

    Google Scholar 

  • Dumdei EJ, Flowers AE, Garson MJ, Moore CJ (1997) The biosynthesis of sesquiterpene isocyanides and isothiocyanates in the marine sponge Acanthella cavernosa (Dendy): evidence for dietary transfer to the dorid nudibranch Phyllidiella pustulosa. Comp Biochem Physiol 118:1385–1392

    Google Scholar 

  • Falshaw CP, King TJ, Imre S, Islimayeli S, Thomson RH (1980) Laurenyne, a new acetylene from Laurencia obtusa: crystal structure and absolute configuration. Tetrahedron Lett 21:4951–4954

    CAS  Google Scholar 

  • Fattorusso E, Magno S, Mayol L, Santacroce C, Sica D (1975) New sesquiterpenoids from the sponge Axinella cannabina. Tetrahedron 31:269–270

    CAS  Google Scholar 

  • Faulkner DJ, Ghiselin MT (1983) Chemical defense and evolutionary ecology of dorid nudibranch and some other opisthobranch gastropods. Mar Ecol Prog Ser 13:295–301

    Google Scholar 

  • Faulkner DJ, Molinski TF, Andersen RJ, Dumdei EJ, De Silva ED (1990) Geographical variation in defensive chemicals from Pacific coast dorid nudibranchs and some related marine molluscs. Comp Biochem Physiol 97 C:233–240

    CAS  Google Scholar 

  • Fontana A, Mollo E, Ricciardi D, Fakhr I, Cimino G (1997) Chemical studies of Egyptian opisthobranchs: spongian diterpenoids from Glossodoris atromarginata. J Nat Prod 60:444–448

    CAS  Google Scholar 

  • Fontana A, Cavaliere P, Ungur N, D’Souza L, Parameswaran PS, Cimino G (1999a) New scalaranes from the nudibranch Glossodoris atromarginata and its sponge prey. J Nat Prod 62:1367–1370

    PubMed  CAS  Google Scholar 

  • Fontana A, Ciavatta ML, Mollo E, Naik CG, Wahidulla S, D’Souza L, Cimino G (1999b) Volvatellin, caulerpenyne-related product from the sacoglossan Volvatella sp. J Nat Prod 62:931–933

    PubMed  CAS  Google Scholar 

  • Fontana A, Cavaliere P, Wahidullah S, Naik CG, Cimino G (2000) A new antitumor isoquinoline alkaloid from the marine nudibranch Jorunna funebris. Tetrahedron 56:7305–7308

    CAS  Google Scholar 

  • Fontana A, Ciavatta ML, D’Souza L, Mollo E, Naik CG, Parameswaran PS, Wahidulla S, Cimino G (2001) Selected chemo-ecological studies of marine opisthbranchs from Indian coasts. J Ind Inst Sci 81:403–415

    CAS  Google Scholar 

  • Francis MP (1980) Habitat, food and reproductive activity of the nudibranch Hexabranchus sanguineus on Tongatapu Island. Veliger 22:252–258

    Google Scholar 

  • Fu X, Hong EP, Schmitz FJ (2000) New polypropionates pyrones from the Philippine Sacoglossan Placobranchus ocellatus. Tetrahedron 56:8989–8993

    CAS  Google Scholar 

  • Fusetani N, Nagata H, Hirota H, Tsuyuki T (1989) Astrogorgiadiol and astrogorgin, inhibitors of cell division in fertilized starfish eggs, from a gorgonian Asterogorgia sp. Tetrahedron Lett 30:7079–7082

    CAS  Google Scholar 

  • Fusetani N, Yasumuro K, Kawai H, Natori T, Brinen L, Clardy J (1990) Kalihinene and isokalihinol B, cytotoxic diterpenes isonitriles from the marine sponge Acanthella klethra. Tetrahedron Lett 31:3599–3602

    CAS  Google Scholar 

  • Garson MJ, Simpson JS (2004) Marine isocyanides and related natural products – structure, biosynthesis and ecology. Nat Prod Rep 21:164–179

    PubMed  CAS  Google Scholar 

  • Gavagnin M, Spinella A, Cimino G, Marin A (1994) Polypropionates from the Mediterranean Mollusc Elysia timida. J Nat Prod 57:298–304

    CAS  Google Scholar 

  • Gavagnin M, Mollo E, Docimo T, Guo Y-W, Cimino G (2004) Scalarane metabolites of the nudibranch Glossodoris rufomarginata and its dietary sponge from the South China Sea. J Nat Prod 67:2104–2107

    PubMed  CAS  Google Scholar 

  • Gonzalez AG, Martin JD, Martin VS, Norte M, Perez R, Ruano JZ (1982) Non-terpenoid C-15 metabolites from the red seaweed Laurencia pinnatifida. Tetrahedron 38:1009–1014

    CAS  Google Scholar 

  • Gopichand Y, Schmitz FJ (1980) Bursatellin, a new diol dinitrile from the sea hare Bursatella leachii pleii. J Org Chem 45:5383–5385

    CAS  Google Scholar 

  • Guella G, Mancini I, Guerriero A, Pietra F (1985) New furanosesquiterpenoids from Mediterranean sponges. Helv Chim Acta 68:1276–1282

    CAS  Google Scholar 

  • Guerriero A, D’Ambrosio M, Pietra F (1987) Verecynarmin A, a novel briarane diterpenoid isolated from both the Mediterranean nudibranch mollusc Armina maculata and its prey, the pennatulacean octocoral Veretillum cynomorium. Helv Chim Acta 70:984–991

    CAS  Google Scholar 

  • Gulavita NK, De Silva ED, Hagadone MR, Karuso P, Scheuer PJ (1986) Nitrogenous bisabolene sesquiterpenes from marine invertebrates. J Org Chem 51:5136–5139

    CAS  Google Scholar 

  • Guo Y-W (1997) Chemical studies of the novel bioactive secondary metabolites from the benthic invertebrates: isolation and structure characterization. Ph.D. thesis, University of Naples, Naples

    Google Scholar 

  • Guo Y-W, Gavagnin M, Mollo E, Trivellone E, Cimino G (1998) Structure of the pigment of the Red Sea nudibranch Hexabranchus sanguineus. Tetrahedron Lett 39:2635–2638

    CAS  Google Scholar 

  • Hamann MT, Scheuer PJ (1993) Kahalalide F: a bioactive depsipeptide from the sacoglossan mollusk Elysia rufescens and the green alga Bryopsis sp. J Am Chem Soc 45:5825–5826

    Google Scholar 

  • Hamann MT, Otto CS, Scheuer PJ, Dumbar C (1996) Kahalalides: bioactive peptides from marine mollusk Elysia rufescens and its algal diet Bryopsis sp. J Org Chem 61:6594–6600

    PubMed  CAS  Google Scholar 

  • Hay ME, Duffy JE, Paul VJ, Renauld PE, Fenical W (1990) Specialist herbivores reduce their susceptibility to predation by feeding on the chemically defended seaweed Avrainvillea longicaulis. Limnol Oceanogr 35:1734–1743

    Google Scholar 

  • He H, Faulkner DJ (1989) Renieramycins E and F from the sponge Reniera sp. reassignment of the stereochemistry of the renieramycins. J Org Chem 54:5822–5824

    CAS  Google Scholar 

  • Hertzberg S, Liaaen-Jensen S, Enzell CR, Francis GW (1969) Animal carotenoids. Acta Chem Scand 23:3290–3312

    CAS  Google Scholar 

  • Hirota H, Tomono Y, Fusetani N (1996) Terpenoids with antifouling activity against barnacle larvae from the marine sponge Acanthella cavernosa. Tetrahedron 52:2359–2368

    CAS  Google Scholar 

  • Hochlowski JE, Faulkner DJ (1980) A diterpene related to cladiellin from a Pacific soft coral. Tetrahedron Lett 21:4055–4056

    CAS  Google Scholar 

  • Horgen FD, delos Santos DB, Goetz G, Sakamoto B, Kan Y, Nagai H, Scheuer PJ (2000) A new depsipeptide from the sacoglossan mollusk, Elysia ornata and the green alga, Bryopsis sp. J Nat Prod 63:152–154

    PubMed  CAS  Google Scholar 

  • Ireland C, Scheuer PJ (1979) Photosynthetic marine mollusks: in vivo 14 C incorporation into metabolites of the sacoglossan Placobranchus ocellatus. Science 205:922–923

    PubMed  CAS  Google Scholar 

  • Ireland C, Faulkner DJ, Solheim BA, Clardy J (1978) Tridachione, a propionate derived metabolites of the opisthobranch mollusk Tridachiella diomedea. J Am Chem Soc 100:1002–1003

    CAS  Google Scholar 

  • Iwashima M, Terada I, Iguchi K, Yamori T (2002) New biologically active marine sesquiterpenoid and steroid from the Okinawan sponge of the genus Axinyssa. Chem Pharm Bull 50:1286–1289

    PubMed  CAS  Google Scholar 

  • Jacobs RS, Bober MA, Pinto I, Williams AB, Jacobson PB, de Carvalho MS (1993). In: Attaway DH, Zaborsky OR (eds) Marine biotechnology, vol 1. Plenum, New York, pp. 77–99

    Google Scholar 

  • Jensen KR (1996) Phylogenetic systematics and classification of the Sacoglossa (Mollusca, Gastropoda, Opisthobranchia). Philos Trans R Soc Lond B 351:91–122

    Google Scholar 

  • Kan Y, Fujita T, Sakamoto B, Hokama Y, Nagai H (1999) Kahalalide K: a new cyclic depsipeptide from the Hawaiian green alga Bryopsis species. J Nat Prod 62:1169–1172

    PubMed  CAS  Google Scholar 

  • Karuso P (1987) Chemical ecology of the nudibranchs. In: Schueur PJ (ed) Bioorganic marine chemistry, vol 1. Springer, Berlin Heidelberg New York, pp. 31–60

    Google Scholar 

  • Karuso P, Taylor WC, White AH (1986) The constituents of marine sponges 11. Isolation of 8 diterpenes from Aplysilla rosea. Aust J Chem 39:1629–1641

    CAS  Google Scholar 

  • Kashman Y (1980) A new diterpenoid related to eunicellin and cladiellin from a Muricella sp. Tetrahedron Lett 21:879–880

    CAS  Google Scholar 

  • Kashman Y, Rudi A (1977) The C-NMR spectrum and stereochemistry of heteronemin from sponge Heteronema erecta; genus Cacospongia. Tetrahedron 33:2997–2998

    CAS  Google Scholar 

  • Kashman Y, Croweiss A, Shmueli U (1980) Latrunculin, a new 2-thiazolidinone macrolide from the marine sponge Latrunculia magnifica. Tetrahedron Lett 21:3629–3632

    CAS  Google Scholar 

  • Kashman Y, Croweiss A, Kidor R, Blasberger D, Carmely S (1985) Latrunculins: NMR study, two new toxins and a synthetic approach. Tetrahedron 41:1905–1914

    CAS  Google Scholar 

  • Kazlauskas R, Murphy PT, Quinn RJ, Wells RJ (1976) Heteronemin, a scalarin type sesterterpene from the sponge Heteronema erecta. Tetrahedron Lett 30:2631–2634

    Google Scholar 

  • Kazlauskas R, Murphy PT, Wells RJ, Daly JJ, Schonholzer P (1978) Two sesquiterpene furans with new carbocyclic ring systems and related thiol acetates from a species of the sponge genus Dysidea. Tetrahedron Lett 49:4951–4954

    Google Scholar 

  • Kazlauskas R, Murphy PT, Wells RJ, Noack K, Oberhansli WE, Schonholzer P (1979) A new series of diterpenes from Australian Spongia species. Aust J Chem 32:867–880

    CAS  Google Scholar 

  • Kernan MR, Molinski TF, Faulkner DJ (1988) Macrocyclic antifungal metabolites from the Spanish dancer nudibranch Hexabranchus sanguineus and sponges of the genus Halicondria. J Org Chem 53:5014–5020

    CAS  Google Scholar 

  • Kernan MR, Cambie CR, Bergquist RP (1990) New diterpenes from the marine sponge Dictyodendrilla cavernosa. J Nat Prod 53:724–727

    CAS  Google Scholar 

  • Kohmoto S, McConnell OJ, Wrigth A, Cross S (1987) Isospongiadiol, a cytotoxic and antiviral diterpene from a Caribbean deep water marine sponge, Spongia sp. Chem Lett 1687–1690

    Google Scholar 

  • Lin GY (1975) Opisthobranchia from the Intertidal zone of Xisha Islands, Guangdong Province, China. Stud Mar Sin 10:141–154

    Google Scholar 

  • Lin GY (1981) A study of the family Arminidae (Opisthobranchia) of the China coast. Stud Mar Sin 18:181–206

    Google Scholar 

  • Lin GY (1986) Additions to the opisthobranch fauna of the Hainan and Xisha Islands of China. Stud Mar Sin 26:117–128

    Google Scholar 

  • Lin H-W, Zhang C, Yi Y-Y, Shen Y, Guo C, Shao Y-F (2001) Studies on antineoplastic constituents from Chinese marine mollusc sea hare (I). Chin J Mar Drugs 20:3–6

    CAS  Google Scholar 

  • Lin H-W, Tang H-F, Liu G-L, Zhang C, Shen Y, Hua Y-Y, Wu H-M (2002) Studies on antineoplastic constituents from Chinese marine mollusc sea hare (II). Acad J Sec Mil Med Univ 23:243–245

    CAS  Google Scholar 

  • Manzo E, Ciavatta ML, Gavagnin M, Mollo E, Guo Y-W, Cimino G (2004) Isocyanide terpene metabolites of Phyllidiella pustulosa, a nudibranch (Mollusca: Gasteropoda) from the South China Sea. J Nat Prod 67:1701–1704

    PubMed  CAS  Google Scholar 

  • Manzo E, Ciavatta ML, Gavagnin M, Mollo E, Wahidulla S, Cimino G (2005a) New ©-pyrone propionates from the Indian Ocean sacoglossan Placobranchus ocellatus. Tetrahedron Lett 46:465–468

    CAS  Google Scholar 

  • Manzo E, Ciavatta ML, Gavagnin M, Puliti M, Mollo E, Guo Y-W, Mattia CA, Mazzarella L, Cimino G (2005b) Structure and absolute stereochemistry of novel C15-halogenated acetogenins from anaspidean mollusc Aplysia dactylomela. Tetrahedron 61:7456–7460

    CAS  Google Scholar 

  • Marin A, Alvarez LA, Cimino G, Spinella A (1999) Chemical defence in cephalaspidean gastropods: origin, anatomical location and ecological roles. J Mol Stud 65:121–131

    Google Scholar 

  • Matsunaga S, Fusetani N, Hashimoto K, Koseki K, Noma M (1986) Kabiramide C, a novel antifungal macrolide from nudibranch eggmasses. J Am Chem Soc 108:847–849

    CAS  Google Scholar 

  • Matsunaga S, Fusetani N, Hashimoto K, Koseki K, Noma M, Noguchi H, Sankawa U (1989) Further kabiramides and halicondramides, cytotoxic macrolides embracing trisoxazole, from the Hexabranchus egg masses. J Org Chem 54:1360–1363

    CAS  Google Scholar 

  • Mebs D (1985) Chemical defense of a dorid nudibranch, Glossodoris quadricolor, from the Red Sea. J Chem Ecol 11:713–716

    CAS  Google Scholar 

  • Miller AK, Trauner D (2005) Mining the tetraene manifold: total synthesis of complex pyrones from Placobranchus ocellatus. Angew Chem Int Ed 44:4602–4606

    CAS  Google Scholar 

  • Miyamoto T, Sakamoto K, Arao K, Komori T, Higuchi R, Sasaki T (1996) Dorisenones, cytotoxic spongian diterpenoids, from the nudibranch Chromodoris obsoleta. Tetrahedron 52:8187–8189

    CAS  Google Scholar 

  • Mollo E, Gavagnin M, Carbone M, Guo Y-W, Cimino G (2005) Chemical studies on Indopacific Ceratosoma nudibranchs illuminate the protective role of their dorsal horn. Chemoecology 15:31–36

    CAS  Google Scholar 

  • Mong S, Votta B, Sarau HM, Foley JJ, Schmidt D, Carte BK, Poehland B, Westley J (1990) 15-Acetylthioxyfurodysinin lactone, isolated from a marine sponge Dysidea sp. is a potent agonist to human leukotriene B4 receptor. Prostaglandins 39:89–97

    PubMed  CAS  Google Scholar 

  • Moses JE, Adlington RM, Rodriguez R, Eade SJ, Baldwin JE (2005) Biomimetic synthesis of ( ± )- 9,10-deoxytridachione. Chem Commun 1687– 1689

    Google Scholar 

  • Ochi M, Yamada K, Shirase K, Kotsuki H (1991) Calicophirins A and B, two new insect growth inhibitory diterpenoids from a gorgonian coral Calicogorgia sp. Heterocycles 32:19–21

    CAS  Google Scholar 

  • Okino T, Yoshimura E, Hirota H, Fusetani N (1995) Antifouling kalihinenes from the marine sponge Acanthella cavernosa. Tetrahedron Lett 36:8637–8640

    CAS  Google Scholar 

  • Okino T, Yoshimura E, Hirota H, Fusetani N (1996) New antifouling kalihipyrans from the marine sponge Acanthella cavernosa. J Nat Prod 59:1081–1083

    CAS  Google Scholar 

  • Ortega MJ, Zubía E, Salvá J (1997) New polyhalogenated monoterpenes from the sea hare Aplysia punctata. J Nat Prod 60:482–484

    PubMed  CAS  Google Scholar 

  • Padmakumar K (1997) Bioactivity and chemical ecology of an opisthobranch Elysia sp. and the dietary alga Bryopsis plumosa. Phuket Mar Biol Cent Spec Publ 18:187

    Google Scholar 

  • Padmakumar K, Lali G (1996) Chemical defence of the specialist ascoglossan Costasiella sp. from the Indian Coast. Phuket Mar Biol Cent Spec Publ 17:61–68

    Google Scholar 

  • Patra A, Chang CWJ, Scheuer PJ, Van Duyne GD, Matsumoto GK, Clardy J (1984) An unprecedented triisocyano diterpenoid antibiotic from a sponge. J Am Chem Soc 106:7981–7983

    CAS  Google Scholar 

  • Poiner A, Paul VJ, Scheuer PJ (1989) Kumepaloxane, a rearranged trisnorsesquiterpene from the bubble shell Haminoea cymbalum. Tetrahedron 45:617–622

    CAS  Google Scholar 

  • Rajaganapathi J, Kathiresan K (2002) Heparinase in purple fluid of the sea hare, Bursatella leachii. Curr Sci 82:264–266

    CAS  Google Scholar 

  • Rajaganapathi J, Kathiresan K, Singh TP (2002) Purification of anti-HIV protein from purple fluid of the sea hare Bursatella leachii de Blainville. Mar Biotechnol 4:447–453

    PubMed  CAS  Google Scholar 

  • Rao CB, Satyanarayana C, Rao DV, Fahy E, Faulkner DJ (1989) Metabolites of Aplysia dactylomela from Indian Ocean. Ind J Chem 28B:322–325

    CAS  Google Scholar 

  • Rao CB, Satyanarayana C, Rao DV, Thompson MF, Nagabhushanam R, Sarojini R, Fingerman M (1994) Recent development in biofouling control. Oxford/IBH, New Delhi, pp. 259–261

    Google Scholar 

  • Roesener JA, Scheuer PJ (1986) Ulapualide A and B: extraordinary antitumor macrolides from nudibranch eggmasses. J Am Chem Soc 108:846–847

    CAS  Google Scholar 

  • Rudman WB (1973) Chromodorid opisthobranch Mollusca from the Indo-West Pacific. Zool J Linn Soc 52:175–199

    Google Scholar 

  • Rudman WB (1986) The Chromodorididae (Opisthobranchia: Mollusca) of the Indo-West Pacific: the genus Glossodoris Ehrenbergh (=Casella, H.& A. Adams). Zool J Linn Soc 86:101–184

    Google Scholar 

  • Rudman WB, Darvell BW (1990) Opisthobranch molluscs of Hong Kong: part 1. Goniodorididae, Onchidorididae, Triophidae, Gymnodorididae, Chromodorididae (Nudibranchia). Asian Mar Biol 7:31–79

    Google Scholar 

  • Schmitz JF, Chang SJ, Hossain BM, van der Helm D(1985) Marine natural products: spongiane derivatives from the Sponge Irgenella notabilis. J Org Chem 50:2862–2865

    CAS  Google Scholar 

  • Seo Y, Rho JR, Cho KW, Shin J (1997) Isolation of diterpenoids of the cladiellane class from gorgonians of the genus Muricella. J Nat Prod 60:171–174

    CAS  Google Scholar 

  • Shimomura M, Miyaoka H, Yamada Y (1999) Absolute configuration of marine diterpenoid kalihinol A. Tetrahedron Lett 40:8015–8017

    CAS  Google Scholar 

  • Spinella A, Alvarez LA, Passeggio A, Cimino G (1993) New 3-alkylpyridines from three Mediterranean cephalaspidean molluscs: structure, ecological role and taxonomic relevance. Tetrahedron 49:1307–1314

    CAS  Google Scholar 

  • Stallard MO, Fenical W, Kittredge JS (1978) The brasilenols, rearranged sesquiterpene alcohols isolated from the marine opisthobranch Aplysia brasiliana. Tetrahedron 34:2077–2081

    CAS  Google Scholar 

  • Subba Rao NV (2003) Indian seashells: part I: Polyplacophora and Gastropoda. Zoological Survey of India, Calcutta, 416 pp

    Google Scholar 

  • Subba Rao NV, Dey A (2000) Catalogue of marine molluscs of Andaman and Nicobar Islands. Zoological Survey of India, Calcutta, 323 pp

    Google Scholar 

  • Tanaka J, Higa T (1988) The absolute configuration of kurospongin a new furanoterpene from a marine sponge, Spongia sp. Tetrahedron 44:2805–2810

    CAS  Google Scholar 

  • Todd CD, Lambert WD, Davies J (2001) Some perspectives on the biology and ecology of nudibranch molluscs: generalisations and variations on the theme that prove the rule. Boll Malacol 37:105–120

    Google Scholar 

  • Willan RC (1979) The ecology of two New Zealand opisthobranch molluscs. Ph.D. thesis, The University of Auckland, Auckland

    Google Scholar 

  • Wratten SJ, Faulkner DJ, Hirotsu K, Clardy J (1978) Diterpenoids isocyanides from the marine sponge Hymeniacidon amphilecta. Tetrahedron Lett 19:4345–4348

    Google Scholar 

  • Yamada K, Kigoshi H (1997) Bioactive compounds from the sea hares of two genera: Aplysia and Dolabella. Bull Chem Soc Jpn 70:1479–1489

    CAS  Google Scholar 

  • Yan X (2004) Study on chemical constituents and bioactivities of seven Chinese marine invertebrates. Ph.D. thesis, Shanghai Institute of Materia Medica, Shanghai, pp. 145–154

    Google Scholar 

  • Yonow N (1990) Red Sea Opisthobranchia 3: the orders Sacoglossa, Cephalaspidea, and Nudibranchia: Doridacea (Mollusca, Opisthobranchia). Fauna Saudi Arabia 11:286–299

    Google Scholar 

  • Yonow N (2000) Red Sea Opisthobranchia 4: the orders Cephalaspidea, Anaspidea, Notaspidea and Nudibranchia: Dendronotacea and Aeolidacea. Fauna Saudi Arabia 18:87–131

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. National Institute of Oceangraphy (NIO-CSIR), Dona Paula, 403 004, Goa, India

    Solimabi Wahidullah

Authors
  1. Solimabi Wahidullah
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Y.-W. Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. M. I. Fakhr
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. Mollo
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Istituto di Chimica Biomolecolare, Consiglio Nazionale delle Ricerche, Via Campi Flegrei, 34, 80078, Pozzuoli (Naples), Italy

    Guido Cimino  & Margherita Gavagnin  & 

Rights and permissions

Reprints and permissions

Copyright information

© 2006 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Wahidullah, S., Guo, YW., Fakhr, I.M.I., Mollo, E. (2006). Chemical Diversity in Opisthobranch Molluscs from Scarcely Investigated Indo-Pacific Areas. In: Cimino, G., Gavagnin, M. (eds) Molluscs. Progress in Molecular and Subcellular Biology, vol 43. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30880-5_8

Download citation

Publish with us

Policies and ethics

Search

Navigation