BIOACTIVE TERPENOID FROM THE BALINESE NUDIBRANCH Hypselodoris infucata

Abstract

Marine organisms, in particular nudibranchs (Mollusca: nudibranchia), are known as a rich source of chemically diverse secondary metabolites exhibiting potential as antimalarial, antiinflammatory, 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.

Bioprospecting of the Balinese marine sponges and nudibranchs

“…Recently, (-)-(6R,11R)-furodysinin (2) has been isolated from D. herbacea (Fiji) [16], from H. bayeri collected from Cuba [17], and from H. jacksoni from South-East Queeensland, Australia. (-)-Furodysinin isolated from H. infucata in the current study has consistently been associated with a 6R,11R configuration, whereas the positive counterpart shows a 6S,11S configuration [18]. …”

Secondary Metabolites from Marine Sources with Potential Use as Leads for Anticancer Applications

“…In the last 5 years, several studies have been carried out with the aim of evaluating the bioactive properties of marine organisms. Several studies have tested the extracts and the isolated compounds from extracts of marine organisms for bioactivities [ 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 ], of which the cytotoxic activity [ 27 , 30 , 32 , 33 , 35 , 36 , 37 , 38 , 40 , 41 , 44 , 45 , 46 , 47 , 48 ] stands out. However, only in some studies was it possible to isolate the compounds and test them for cytotoxic activity [ 32 , 33 , 35 , 36 , 37 , 38 , 40 , 41 ].…”

“…Compound ( 32 ) ( Figure 4 ), a sesquiterpene isolated from the coral H. fuscescens , showed moderate cytotoxic activity against MCF-7 (IC 50 86.45 ± 12.00 μM) ( Table 2 ), with an IC 50 that is half that reported for the positive control (vinblastine), and against OVK-18 (IC 50 141.64 ± 9.80 μM) [ 37 ]. In the case of compound ( 33 ) ( Figure 4 ), isolated from the sea slug H. infucata , the IC 50 against the human cervical cancer cell line HeLa is 474.76 μM, a very high value, especially when compared to the positive control, doxorubicin (IC 50 4.23 μM) [ 38 ].…”

Terpenoids in Marine Heterobranch Molluscs

“…Pallescensin A and several other terpenes are found in the Patagonian doridacean Tyrinna nobilis [89]. Hypselodoris infucata from Bali yielded the known (−)-furodysinin (34) ( Figure 5), being active against the HeLa cell line with an IC 50 at 102.7 µg/mL, while its crude extract is repellent to the sympatric shrimp Penaeus vannamei at natural concentration [169]. Similarly, the species H. kanga from India possesses furodysinin, suggesting a trophic relationship, since furodysinin is also found in the associated demosponge Dysidea sp.…”