Journal
HELVETICA CHIMICA ACTA
Volume 94, Issue 6, Pages 1012-1018Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.201100117
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Funding
- NSF [IOS-0324435, IOS-0614685, IOS-1036742]
- Division Of Integrative Organismal Systems
- Direct For Biological Sciences [1036742] Funding Source: National Science Foundation
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Three new mycosporine-like amino acids (MAAs), aplysiapalythines A, B, and C (1, 2, and 3, resp.) were isolated from opaline, a glandular component of the defensive ink secretion of sea hares (Aplysia californica) collected from waters off southern California. Here, we report the structure of these MAAs determined by mass spectrometry and NMR data. These new MAAs are structurally related to two known MAAs that are also present in sea hare opaline, i.e., asterina 330 (4) and palythine (5), and for which we also provide detailed data here for comparison. The fact that three of the five MAAs that we identified from sea hare opaline are novel molecules is interesting given that this represents a relatively large addition to the current list of known MAAs. This is likely because most researchers have identified MAAs through HPLC with UV detection, which is imprecise given similarities in UV spectra for different MAAs. Our findings suggest that there is much greater diversity of MAAs than is currently known. Results published elsewhere show that 1, 2, and 4 are alarm cues for conspecific sea hares at natural concentrations, but 3 and 5 are not.
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