Chemoecological studies on marine natural products: terpene chemistry from marine mollusks

Mudianta, I. Wayan, White, Andrew M., Suciati, Katavic, Peter L., Krishnaraj, Rahul R., Winters, Anne E., Mollo, Ernesto, Cheney, Karen L. and Garson, Mary J. (2014). Chemoecological studies on marine natural products: terpene chemistry from marine mollusks. In: 44th IUPAC World Chemistry Congress: Clean Energy Through Chemistry. Invited Papers. IUPAC 2013: 44th World Chemistry Congress, Istanbul, Turkey, (995-1002). 11-16 August, 2013. doi:10.1515/pac-2013-1111

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Author Mudianta, I. Wayan
White, Andrew M.
Katavic, Peter L.
Krishnaraj, Rahul R.
Winters, Anne E.
Mollo, Ernesto
Cheney, Karen L.
Garson, Mary J.
Title of paper Chemoecological studies on marine natural products: terpene chemistry from marine mollusks
Conference name IUPAC 2013: 44th World Chemistry Congress
Conference location Istanbul, Turkey
Conference dates 11-16 August, 2013
Convener IUPAC Secretariat
Proceedings title 44th IUPAC World Chemistry Congress: Clean Energy Through Chemistry. Invited Papers   Check publisher's open access policy
Journal name Pure and Applied Chemistry   Check publisher's open access policy
Place of Publication Berlin, Germany
Publisher Walter de Gruyter
Publication Year 2014
Year available 2014
Sub-type Fully published paper
DOI 10.1515/pac-2013-1111
Open Access Status File (Publisher version)
ISSN 0033-4545
Volume 86
Issue 6
Start page 995
End page 1002
Total pages 8
Language eng
Formatted Abstract/Summary
Some species of nudibranchs (Mollusca) protect themselves from predatory attacks by storing defensive terpene chemicals acquired from dietary sponges (Porifera) in specialized body parts called MDFs (mantle dermal formations), often advertising their unpalatability to potential predators by means of bright coloration patterns. Consequently, the survival of these trophic specialist species is closely related to the possibility of obtaining the defensive tools from sponges that live in their immediate vicinity; therefore, it is important to determine as precisely as possible the chemical composition of nudibranch extracts prior to any ecological studies addressing issues that involve their alimentary behavior and their defensive strategies, including the significance of their color patterns. Some of our recent studies on the chemical composition of terpene extracts from nudibranchs belonging to the genera Chromodoris and Hypselodoris are summarized. We also report the development of a method to assay extracts and purified metabolites for their feeding deterrent activity against co-occurring generalist predators. In a recent chemoecological study, showing that repugnant terpene chemicals are accumulated at extremely high concentrations in exposed parts of the nudibranchs' bodies, the feeding deterrence assays were carried out on the generalist marine shrimp Palaemon elegans, very common in the Mediterranean. We have modified this assay for use with the Australian shrimp species P. serenus, and confirmed the ecological validity of the assay by analysis of extracts from species of sponges and mollusks that live in the same habitat as P. serenus. The deterrent properties of haliclonacyclamine alkaloids isolated from the sponge Haliclona sp. were demonstrated, with the alkaloid mixture demonstrating palatability deterrence at concentrations as low as 0.05 mg/mL, and complete deterrence at 0.75 mg/mL. In contrast, the diterpene thuridillin metabolites from the sacoglossan mollusk Thuridilla splendens did not deter feeding by P. serenus.
Keyword Assay
Enantioselective synthesis
IUPAC congress-44
Life chemistry
Marine natural products
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes "Article note: A collection of invited papers based on presentations on the Life Chemistry theme at the 44th IUPAC Congress, Istanbul, Turkey, 11–16 August 2013."

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