Natural Products Isolated From Species of Halgerda Bergh, 1880 (Mollusca: Nudibranchia) and Their Ecological and Evolutionary Implications

Shireen J Fahey; A R Carroll

doi:10.1007/s10886-007-9288-z

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Natural Products Isolated From Species of Halgerda Bergh, 1880 (Mollusca: Nudibranchia) and Their Ecological and Evolutionary Implications

Journal article

Peer reviewed

Natural Products Isolated From Species of Halgerda Bergh, 1880 (Mollusca: Nudibranchia) and Their Ecological and Evolutionary Implications

Shireen J Fahey and A R Carroll

Journal of Chemical Ecology, Vol.33(6), pp.1226-1234

2007

DOI: https://doi.org/10.1007/s10886-007-9288-z

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Abstract

Ecology

Other Chemical Sciences

halgerdamine

tryptophan conjugates

C2-a-dmannosylpyranosyl-L-tryptophan

tryptophan metabolism

muscarinic agonist

cytotoxicity

marine sponges

evolutionary relationships

Chemical investigations of five species of molluscan nudibranchs, Halgerda, collected from Australia and Japan were carried out. We identified a novel tryptophan derivative halgerdamine (1) along with the known compounds trigonellin (3), esmodil (4), zooanemonin (5), and C2-α-D-mannosylpyranosyl-L-tryptophan (2) from Halgerda aurantiomaculata. C2-α-D-mannosylpyranosyl-L-tryptophan (2) was previously thought to be a by-product of tryptophan metabolism exclusive to humans. The only other chordates reported to contain this compound are a number of ascidian species from New Caledonia and Australia including Atriolum robustum and Leptoclinides dubius. The occurrence of 2 in a mollusc has not been previously reported. Structure elucidation of 1 was achieved by using high-field 2D NMR spectroscopy. No secondary metabolites were detected in extracts from five of the six other species studied, whereas Halgerda gunnessi contained mixtures of acylated tetrasaccharides. The compounds isolated from Halgerda are different from those found in the close sister taxon, Asteronotus. Specifically, species of Halgerda contain no terpenes, spirodysin, or bromophenols, as does Asteronotus. Furthermore, in contrast to other members of the Nudibranchia such as Chromodoris and Phyllidia, in which compound yields are quite high, several cryptic species of Halgerda seem to lack secondary metabolites, whereas the two highly conspicuous species yield mildly cytotoxic MeOH extracts. Our findings support recent hypotheses regarding progressive evolution of opisthobranchs. In particular, opisthobranchs have evolved to exploit a wider range of food and metabolites than did their ancestors, a demonstration of physiological innovation. Some species of Halgerda may not be chemically protected either via de novo synthesis or by sequestering particularly toxic compounds.

Details

Title: Natural Products Isolated From Species of Halgerda Bergh, 1880 (Mollusca: Nudibranchia) and Their Ecological and Evolutionary Implications
Authors: Shireen J Fahey (Author) - California Academy of Sciences, United States
A R Carroll (Author) - Griffith University
Publication details: Journal of Chemical Ecology, Vol.33(6), pp.1226-1234
Publisher: Springer New York LLC
Date published: 2007
DOI: 10.1007/s10886-007-9288-z
ISSN: 0098-0331
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449715702621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Biochemistry & Molecular Biology; Ecology

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