Research Article Volume 27 Issue 2 (2016) 104 Indonesian J. Pharm. Vol. 27 No. 2 : 104 – 110 ISSN-p : 2338-9427 DOI: 10.14499/indonesianjpharm27iss2pp104 BIOACTIVE TERPENOID FROM THE BALINESE NUDIBRANCH Hypselodoris infucata I Wayan Mudianta 1 *, Ni Wayan Martiningsih 1 , I Nyoman Dodik Prasetia 2 , Muhammad Nursid 3 . 1 Dept of Analytical Chemistry, Ganesha Univ. of Education, Jl. Udayana No. 11 Singaraja, Bali 81116 2 Dept. of Marine Culture, Ganesha Univ. of Education, Jl. Udayana No. 11 Singaraja, Bali 81116 3 Res. and Dev.t Center for Marine and Fisheries Product Processing and Biotechnology, Jl. KS. Tubun Petamburan VI Jakarta, 10260 Submitted: 02-02-2016 Revised: 25-02-2016 Accepted: 24-03-2016 *Corresponding author I Wayan Mudianta Email: mudianta@undiksha.ac.id 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 1 H 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 INTRODUCTION Secondary metabolites play an important role as a starting point in the drug discovery process. Marine organisms offer an abundant source of chemically diverse and biologically active secondary metabolites. Among marine organisms, sponges and nudibranchs are prolific sources of diverse natural products, and the study of their chemical properties has led to the discovery of many biologically potent chemicals with antimalarial, anti-inflammatory, antiviral and anticancer activity (Blunt et al., 2015). Nudibranchs (Mollusca: nudibranchia) are slow-moving marine molluscs with soft bodies and often present bright and attractive coloration. However, despite slow movements and the absence of physical attributes, only few predators have been documented. Chemoeco- logical studies showed that nudibranchs may employ secondary metabolites as chemical defence mechanism against predators (Cimino and Ghiselin, 2009; Mudianta et al., 2014). The metabolites are either derived from their diets mainly sponges or biosynthesized in de novo fashion (Fontana et al., 2012). This sponge- prey relationship has resulted an array of metabolites with intriguing framework, which are not found in their terrestrial counterparts and showed the potential as new pharmaceutical agents (Gerwick and Moore, 2012). Furanosesquiterpenoids are the most dominant metabolites characterised from nudibranchs of the genus Hypselodoris (Gastropoda: nudibranchia) and they seem to be a specific chemotaxonomic marker in these organisms (Fontana et al., 2001). Additionally, some species within this genus have also been reported to produce diterpenoids (Hochlowski et al., 1982) as well as sesterpenoids (Cimino et al., 1993). There have been 17 different species of Hypselodoris chemically investigated and reported from 1982 until 2012. The animals were collected from disparate geographical regions including California (USA), Brazil (Latin America), the Mediterranean (Europe), South Africa, and India.