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Open AccessArticle

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

1
Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia
2
Department of Medical Laboratory Technology, Faculty of Applied Medical Sciences, King Abdulaziz University, Jeddah 21589, Saudi Arabia
3
Suez Canal University Hospital, Suez Canal University, Ismailia 41522, Egypt
4
Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia
5
Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt
6
Special Infectious Agents Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia
7
UMR 8038 CiTCoM, Faculté de Pharmacie de Paris, Université Paris Descartes, Avenue de l’observatoire, 75006 Paris, France
8
Molecules of Communication and Adaptation of Microorganisms (UMR 7245), National Museum of Natural History, CNRS, 75231 Paris, France
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2019, 17(10), 584; https://doi.org/10.3390/md17100584
Received: 10 September 2019 / Revised: 12 October 2019 / Accepted: 12 October 2019 / Published: 16 October 2019
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. View Full-Text
Keywords: sponge-derived Streptomyces sp. Call-36; diketopiperazine alkaloids; nucleoside derivatives; NMR and ECD calculations; cytotoxic and antimicrobial activities sponge-derived Streptomyces sp. Call-36; diketopiperazine alkaloids; nucleoside derivatives; NMR and ECD calculations; cytotoxic and antimicrobial activities
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MDPI and ACS Style

Shaala, L.A.; Youssef, D.T.A.; Badr, J.M.; Harakeh, S.M.; Genta-Jouve, G. Bioactive Diketopiperazines and Nucleoside Derivatives from a Sponge-Derived Streptomyces Species. Mar. Drugs 2019, 17, 584.

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