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Mar. Drugs 2018, 16(10), 345; https://doi.org/10.3390/md16100345

Seco-Tetracenomycins from the Marine-Derived Actinomycete Saccharothrix sp. 10-10

1
Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
2
College of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China
3
Key Laboratory of Medicinal Chemistry and Molecular Diagnostic of Ministry of Education, College of Pharmacy, Hebei University, Baoding 071002, China
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 30 August 2018 / Revised: 17 September 2018 / Accepted: 18 September 2018 / Published: 20 September 2018
(This article belongs to the Special Issue Natural Products from Marine Actinomycetes)
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Abstract

Six new tetracenomycin congeners, saccharothrixones E–I (15) and 13-de-O-methyltetracenomycin X (6), were isolated from the rare marine-derived actinomycete Saccharothrix sp. 10-10. Their structures were elucidated by spectroscopic analysis and time-dependent density functional theory (TDDFT)-electronic circular dichroism (ECD) calculations. Saccharothrixones G (3) and H (4) are the first examples of tetracenomycins featuring a novel ring-A-cleaved chromophore. Saccharothrixone I (5) was determined to be a seco-tetracenomycin derivative with ring-B cleavage. The new structural characteristics, highlighted by different oxidations at C-5 and cleavages in rings A and B, enrich the structural diversity of tetracenomycins and provide evidence for tetracenomycin biosynthesis. Analysis of the structure–activity relationship of these compounds confirmed the importance of the planarity of the naphthacenequinone chromophore and the methylation of the polar carboxy groups for tetracenomycin cytotoxicity. View Full-Text
Keywords: marine actinomycete; Saccharothrix sp.; seco-tetracenomycin; saccharothrixone; structure-activity relationship marine actinomycete; Saccharothrix sp.; seco-tetracenomycin; saccharothrixone; structure-activity relationship
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Liu, B.; Li, J.; Chen, M.; Hao, X.; Cao, F.; Tan, Y.; Ping, Y.; Wang, Y.; Xiao, C.; Gan, M. Seco-Tetracenomycins from the Marine-Derived Actinomycete Saccharothrix sp. 10-10. Mar. Drugs 2018, 16, 345.

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