BIOACTIVE TERPENOID FROM THE BALINESE NUDIBRANCH Hypselodoris infucata

I Wayan Mudianta, Ni Wayan Martiningsih, I Nyoman Dodik Prasetia, Muhammad Nursid

Abstract


Marine organisms, in particular nudibranchs (Mollusca: nudibranchia), are known as a rich source of chemically diverse secondary metabolites exhibiting potential as antimalarial, anti-inflammatory, antiviral and anticancer activity. We presented the chemical investigation of an extract of nudibranch Hypselodoris infucata collected from Bali, an unexplored water but rich in nudibranch diversity. The extract contained the known (–)-furodysinin (1), a furanosesquiterpene that for the first time isolated from this species. Metabolite 1 was purified by chromatography and the structure was characterised by comparison of 1H NMR data with that of the reported data. The absolute configuration was determined by comparing the optical rotation values with the known enantiomer. In vitro cytotoxic activity of compound 1 against HeLa cell line displayed an IC50 at 102.7µg/mL. We also report for the first time the development of a method to assay nudibranch extracts for their feeding deterrence activity against local shrimps Penaeus vannamei. The extract show food rejection with highly significant difference in respect to the control (P = 0.0061) at natural concentration of 3.0mg/mL.

Keywords: nudibranch, natural product, feeding deterrence, Hypselodoris


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References


Blunt JW, Copp BR, Keyzers RA, Munro MHG, Prinsep MR. 2015. Marine natural products. Natural Product Reports 32:116-211

Carte' B, Mong S, Poehland B, Sarau H, Westley JW, Faulkner DJ. 1989. 15-Acetylthioxy-furodysinin lactone, a potent LTB4 receptor partial agonist from a marine sponge of the genus Dysidea. Tetrahedron Letters 30:2725–6

Cimino G, Fontana A, Gimenez F, Marin A, Mollo E, et al. 1993. Biotransformation of dietary sesterterpenoids in the Mediterranian nudi Hypselodoris orisini. Experientia 49:582-6

Cimino G, Ghiselin MT. 2009. Chemical defense and the evolution of opistobranch gastropod. Proc. Calif. Acad. Sci. 60:175-422

da Cruz JF, Gaspar H, Calado G. 2012. Turning the game around: toxicity in a nudibranch-sponge predator-prey association. Chemoecology 22:47-53

Dunlop RW, Kazlauskas R, March G, Murphy PT, Wells RJ. 1982. New Furano-Sesquiterpenes from the Sponge Dysidea herbacea. Aust. J. Chem. 35:95-103

Fontana A, Ciavatta ML, D'Souza L, Mollo E, Naik CG, et al. 2001. Selected chemo-ecological studies of marine opisthobranchs from Indian coasts. J. Indian Inst. Sci. 81:403-15

Fontana A, Manzo E, Ciavatta ML, Cutignano A, Gavagnin M, Cimino G. 2012. Biosynthetic studies through feeging experiments in marine organisms. In Handbook of Marine Natural Products, ed. E Fattorusso, WH Gerwick, Taglialatela-ScafatiBerlin: Springer. 895–946 pp.

Fontana A, Trivellone E, Mollo E, Cimino G, Avila C, et al. 1994. Further chemical studies of Mediterranean. J. Nat. Prod. 57:510-3

Gerwick WH, Moore BS. 2012. Lessons from the Past and Charting the Future of Marine Natural Products Drug Discovery and Chemical Biology. Chem. Biol. 19:85-98

Guella G, Mancini I, Guerriero A, Pietra F. 1985. New Furano-sesquiterpenoids from Mediterranean Sponges. Helv. Chim. Acta:1276-82

Hochlowski JE, Walker RP, Ireland C, Faulkner DJ. 1982. Metabolites of Four Nudibranchs of the Genus Hypselodoris. J. Org. Chem. 47:88-91

Horton P, Inman WD, Crews P. 1990. Enantiomeric relationship and anthelmintic activity. J. Nat. Prod. 53:143-51

Hughes D, Mehmet H. 2003. Cell proliferation and apoptosis. Advanced methods. Oxford: Bios Scientific Publishers Limited

Kazlauskas R, Murphy PT, Wells RJ. 1978. Two sesquiterpene furans with new carbocyclic ring systems. Tetrahedron Lett. 49:4951-4

Mándi A, Mudianta IW, Kurtán T, Garson MJ. 2015. Absolute Configuration and Conformational Study of Psammaplysins A and B from the Balinese Marine Sponge Aplysinella strongylata. J. Nat. Prod. 78:2051-6

Mollo E, Gavagnin M, Carbone M, Castellucio F, Pozone F, et al. 2008. Factors promoting marine invasions: A chemoecological approach. Proc. Natl. Acad. Sci. 105:4582-6

Mudianta IW, White AM, Suciati, Katavic PL, Krishnaraj RR, et al. 2014. Chemoecological studies on marine natural products: terpene chemistry from marine mollusks. Pure Appl. Chem. 86:995–1002

Richou O, Vaillancourt V, Faulkner DJ, Albizati KF. 1989. Synthesis and Absolute Configuration of (-)-Furodysinin. New Transformations of Camphor Derivatives. J. Org. Chem. 54:4729-30

Searle PA, Jamal NM, Lee GM, Molinski TF. 1994. Configurational analysis of new furanosesquiterpenes from Dysidea. Tetrahedron 50:3879-88

Vaillancourt V, Agharahimi MR, Sundram UN, Richou O, Faulkner DJ, Albizati KF. 1991. Synthesis and Absolute Configuration of the Antiparasitic Furanosesquiterpenes (-)-Furodysin and (-)-Furodysinin. Camphor as a Six-Membered Ring Chiral Pool Template. J. Org. Chem. 56:378-87




DOI: http://dx.doi.org/10.14499/indonesianjpharm27iss2pp104

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