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A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens.

ABSTRACT: Lyngbyatoxin A from the marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) is known as the causative agent of "swimmer's itch" with its highly inflammatory effect. A new toxic compound was isolated along with lyngbyatoxin A from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies revealed the isolated compound had the same planar structure with that of lyngbyatoxin A. The results of optical rotation and CD spectra indicated that the compound was a new lyngbyatoxin A derivative, 12-epi-lyngbyatoxin A (1). While 12-epi-lyngbyatoxin A showed comparable toxicities with lyngbyatoxin A in cytotoxicity and crustacean lethality tests, it showed more than 100 times lower affinity for protein kinase C? (PKC?) using the PKC?-C1B peptide when compared to lyngbyatoxin A.

SUBMITTER: Jiang W

PROVIDER: S-EPMC4052313 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens.

Jiang Weina W Zhou Wei W Uchida Hajime H Kikumori Masayuki M Irie Kazuhiro K Watanabe Ryuichi R Suzuki Toshiyuki T Sakamoto Bryan B Kamio Michiya M Nagai Hiroshi H

Marine drugs 20140512 5

Lyngbyatoxin A from the marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) is known as the causative agent of "swimmer's itch" with its highly inflammatory effect. A new toxic compound was isolated along with lyngbyatoxin A from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies revealed the isolated compound had the same planar structure with that of lyngbyatoxin A. The results of optical rotation and CD spectra indicate ...[more]

PMID: 24824022

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