Dataset Information

Trichodermanins C-E, New Diterpenes with a Fused 6-5-6-6 Ring System Produced by a Marine Sponge-Derived Fungus.

ABSTRACT: Trichodermanins C-E (1-3), new diterpenes with a rare fused 6-5-6-6 ring system, have been isolated from a fungus Trichoderma harzianum OUPS-111D-4 separated from a piece of a marine sponge Halichondria okadai, and these chemical structures have been established by spectroscopic analyses using IR, MASS, HRFABMS, and NMR spectra. We established their absolute stereostructures by application of the modified Mosher's method. In addition, 1 inhibited the growth of cancer cell lines potently.

SUBMITTER: Yamada T

PROVIDER: S-EPMC5484119 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Trichodermanins C-E, New Diterpenes with a Fused 6-5-6-6 Ring System Produced by a Marine Sponge-Derived Fungus.

Yamada Takeshi T Suzue Mayo M Arai Takanobu T Kikuchi Takashi T Tanaka Reiko R

Marine drugs 20170609 6

Trichodermanins C-E (1-3), new diterpenes with a rare fused 6-5-6-6 ring system, have been isolated from a fungus Trichoderma harzianum OUPS-111D-4 separated from a piece of a marine sponge Halichondria okadai, and these chemical structures have been established by spectroscopic analyses using IR, MASS, HRFABMS, and NMR spectra. We established their absolute stereostructures by application of the modified Mosher's method. In addition, 1 inhibited the growth of ...[more]

PMID: 28598397

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Project description:The marine sponge Raspailia bouryesnaultae, collected in South Brazil, was selected for detailed investigation considering the results of a screening that pointed to an in vitro antiproliferative effect against non-small cells of human lung cancer (A549) and anti-herpes activity against Herpes Simplex virus type 1 (KOS and 29R strains) of ethanolic extracts. The fractionation and chemical investigation of the sponge's hexanic fraction led to the isolation and structural elucidation of six clerodane diterpenes. The main component was identified as the already-reported raspailol (1), isolated from a sponge of the same genus collected in New Zealand. The structure of a new diterpene (2) with a rearranged skeleton was established by high-resolution mass spectrometry (HRMS) and 1D and 2D Nuclear magnetic resonance spectroscopy (NMR) experiments, and named here as raspadiene. Furthermore, four diterpenes were elucidated as isomers of clerodane diterpenes previously obtained from plants, namely kerlinic acid (3), kerlinic acid methyl ester (4), annonene (5), and 6-hydroxyannonene (6). They differ in their stereochemistry, since these diterpenes are characterized by a trans ring fusion at the decalin moiety and the relative configuration of the two methyl groups at C-8 and C-9 in a cis relationship (type trans/cis). The Raspailia diterpenes have a cis ring fusion at the decalin moiety, and the two methyl groups at C-8 and C-9 are in a trans relationship (type cis/trans). The isolated compounds were evaluated for their potential antiproliferative effects on human cancer cell line A549, and it was observed that the diterpenes bearing a hydroxyl group at C-6 exhibited moderate cytotoxic activity, with 50% inhibitory concentration (IC50) values lower than 25 ?M. The evaluation of the potential anti-herpes activity against Herpes Simplex Virus type 1 (HSV-1, KOS and 29R strains) showed that the more promising results were observed for the new compound 2, since it inhibited HSV-1 (KOS and 29R strains) replication by 83% and 74%, respectively.

Dataset Information

Trichodermanins C-E, New Diterpenes with a Fused 6-5-6-6 Ring System Produced by a Marine Sponge-Derived Fungus.

Publications

Trichodermanins C-E, New Diterpenes with a Fused 6-5-6-6 Ring System Produced by a Marine Sponge-Derived Fungus.

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