Pyrane-based cembranoid and 2-dehydro-4-peroxy-sarcophine: two new diterpenes from <i>Sarcophyton glaucum</i>-Reference-Cited by-同舟云学术

Pyrane-based cembranoid and 2-dehydro-4-peroxy-sarcophine: two new diterpenes from Sarcophyton glaucum

Published:2024-03-01 Issue:3-4 Volume:79 Page:81-87
ISSN:0939-5075
Container-title:Zeitschrift für Naturforschung C
language:en
Short-container-title:

Author:

Shaaban Mohamed¹²^ORCID,Ghani Mohamed A.³

Affiliation:

1. Chemistry of Natural Compounds Department, Pharmaceutical and Drug Industries Research Institute , National Research Centre , El-Behoos St. 33 12622 Dokki-Cairo , Egypt

2. Institute of Organic and Biomolecular Chemistry , University of Göttingen , Tammannstrasse 2, D-37077 Göttingen , Germany

3. Red Sea Marine Parks , PO Box 363, Red Sea, A.R , Hurghada , Egypt

Abstract

Abstract Soft corals, particularly Sarcophyton sp. are rich in metabolites with variety of biological activities. In this study, a pyran-based 9-exo-methylene-10-hydroxy-sarcotrocheliol (1) and 2-dehydro-4-peroxy-sarcophine (2), two new cembranoide diterpenes, were isolated together with 9-hydroxy-10,11-dehydro-sarcotrocheliol, sarcotrocheliol, sarcotrocheliol acetate, sarcophine, (+)-7α,8β-dihydroxydeepoxysarcophine, (±)-sarcophytonine B, and peridinin from the organic extract of Sarcophyton glaucum collected at the coasts of Hurghada, Egypt. The structures of the new diterpenes 1–2 were identified based on cumulative analyses of HRESIMS and NMR (1D/2D NMR) spectra. The relative configurations of both compounds were verified by NOESY spectra and comparison with our recently reported analogues. The compounds showed no antimicrobial activity against a set of diverse tested microorganisms.

Publisher

Walter de Gruyter GmbH

Link

https://www.degruyter.com/document/doi/10.1515/znc-2024-0004/pdf

Reference32 articles.

1. Nurrachma, MY, Sakaraga, D, Nugraha, AY, Rahmawati, SI, Bayu, A, Sukmarini, L, et al.. Cembranoids of soft corals: recent updates and their biological activities. Nat Prod Bioprospect 2021;11:243–306. https://doi.org/10.1007/s13659-021-00303-2.

2. Bernstein, J, Schmeuli, U, Zadock, E, Kashman, Y, Neeman, I. Sarcophine, a new epoxy cembranolide from marine origin. Tetrahedron 1974;30:2817–24. https://doi.org/10.1016/s0040-4020(01)97451-4.

3. Kashman, Y, Zadock, E, Neeman, I. Some new cembrane derivatives of marine origin. Tetrahedron 1974;30:3615–20. https://doi.org/10.1016/s0040-4020(01)97044-9.

4. Tursch, B. Some recent developments in the chemistry of alcyonaceans. Pure Appl Chem 1976;48:1–6. https://doi.org/10.1351/pac197648010001.

5. Bowden, F, Coll, JC, Mitchell, SJ, Stoke, GJ. Studies of Australian soft corals. XI. Two new cembranoid diterpenes from a Sarcophyton species. Aust J Chem 1979;32:653–9. https://doi.org/10.1071/ch9790653.