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Bioactive Diketopiperazines and Nucleoside Derivatives from a Sponge-Derived Streptomyces Species.


ABSTRACT: Fractionation and purification of the ethyl acetate extract of the culture of a sponge-derived actinomycete, Streptomyces species Call-36, resulted in the isolation and identification of a new diketopiperazine, actinozine A (1), cyclo(2-OH-d-Pro-l-Leu) (2), two new nucleosides, thymidine-3-mercaptocarbamic acid (3) and thymidine-3-thioamine (4), together with cyclo(d-Pro-l-Phe) (5) and cyclo(l-Pro-l-Phe) (6). The structure assignments of the compounds were carried out by interpretation of 1D and 2D NMR data and mass spectral determinations. The absolute configurations of 1 and 2 were determined by Marfey's method and by comparison of the experimental and TDDFT-calculated ECD spectra. Actinozine A possesses an unprecedented hydroperoxy moiety at C-2 of the proline moiety, while 3 and 4 possess unusual mercaptocarbamic acid and thiohydroxylamine functionalities at N-3 of the thymine moiety. The isolated compounds displayed variable cytotoxic and antimicrobial activities.

SUBMITTER: Shaala LA 

PROVIDER: S-EPMC6835933 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Bioactive Diketopiperazines and Nucleoside Derivatives from a Sponge-Derived <i>Streptomyces</i> Species.

Shaala Lamiaa A LA   Youssef Diaa T A DTA   Badr Jihan M JM   Harakeh Steve M SM   Genta-Jouve Grégory G  

Marine drugs 20191016 10


Fractionation and purification of the ethyl acetate extract of the culture of a sponge-derived actinomycete, <i>Streptomyces</i> species Call-36, resulted in the isolation and identification of a new diketopiperazine, actinozine A (<b>1</b>), cyclo(2-OH-d-Pro-l-Leu) (<b>2</b>), two new nucleosides, thymidine-3-mercaptocarbamic acid (<b>3</b>) and thymidine-3-thioamine (<b>4</b>), together with cyclo(d-Pro-l-Phe) (<b>5</b>) and cyclo(l-Pro-l-Phe) (<b>6</b>). The structure assignments of the compo  ...[more]

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