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Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388.

ABSTRACT: Four new thiodiketopiperazine alkaloids, namely, 5'-hydroxy-6'-ene-epicoccin G (1), 7-methoxy-7'-hydroxyepicoccin G (2), 8'-acetoxyepicoccin D (3), and 7'-demethoxyrostratin C (4), as well as a pair of new enantiomeric diketopiperazines, (±)-5-hydroxydiphenylalazine A (5), along with five known analogues (6-10), were isolated and identified from the culture extract of Epicoccum nigrum SD-388, a fungus obtained from deep-sea sediments (-4500 m). Their structures were established on the basis of detailed interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis confirmed the structures and established the absolute configurations of compounds 1-3, while the absolute configurations for compounds 4 and 5 were determined by ECD calculations. Compounds 4 and 10 showed potent activity against Huh7.5 liver tumor cells, which were comparable to that of the positive control, sorafenib, and the disulfide bridge at C-2/C-2' is likely essential for the activity.

SUBMITTER: Chi LP 

PROVIDER: S-EPMC7143119 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus <i>Epicoccum nigrum</i> SD-388.

Chi Lu-Ping LP   Li Xiao-Ming XM   Li Li L   Li Xin X   Wang Bin-Gui BG  

Marine drugs 20200313 3

Four new thiodiketopiperazine alkaloids, namely, 5'-hydroxy-6'-ene-epicoccin G (<b>1</b>), 7-methoxy-7'-hydroxyepicoccin G (<b>2</b>), 8'-acetoxyepicoccin D (<b>3</b>), and 7'-demethoxyrostratin C (<b>4</b>), as well as a pair of new enantiomeric diketopiperazines, (±)-5-hydroxydiphenylalazine A (<b>5</b>), along with five known analogues (<b>6</b>-<b>10</b>), were isolated and identified from the culture extract of <i>Epicoccum nigrum</i> SD-388, a fungus obtained from deep-sea sediments (-4500  ...[more]

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