Journal of Natural Products, volume 79, issue 7, pages 1891-1895

Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete Saccharothrix sp. and Their Structure–Activity Relationship

Lu Shan 1
Ito Masashi 2
Tsuchida Toshio 2
Kakeya Hideaki 1
1
 
Department of System Chemotherapy and Molecular Sciences, Division of Bioinformatics and Chemical Genomics, Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto 606-8501, Japan
2
 
Bioresource Laboratories, MicroBioPharm Japan Co., Ltd. (MBJ), Iwata, Shizuoka 438-0078, Japan
Publication typeJournal Article
Publication date2016-06-22
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor5.1
ISSN01633864, 15206025
Organic Chemistry
Drug Discovery
Pharmacology
Pharmaceutical Science
Molecular Medicine
Complementary and alternative medicine
Analytical Chemistry
Abstract
Three new 10-membered macrolides, saccharothriolides D-F (1-3), were isolated from a rare actinomycete, Saccharothrix sp. A1506. The planar structures were determined from analysis of extensive NMR and HR-ESI-MS data, and the absolute configurations were established by ECD spectroscopy analysis. Saccharothriolides D (1) and E (2) were determined to be C-2 epimers of saccharothriolides A (4) and B (5), respectively. Saccharothriolide F (3) was identified to be a demethylated congener of saccharothriolides D (1) and A (4) at the C-2 position. The availability of compounds 1-6 enabled a structure-activity relationship study that revealed the importance of the phenolic hydroxy group at C-2″ and the stereochemistry of C-2 for the inhibition of human fibrosarcoma HT1080 cell growth.

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Lu S. et al. Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete Saccharothrix sp. and Their Structure–Activity Relationship // Journal of Natural Products. 2016. Vol. 79. No. 7. pp. 1891-1895.
GOST all authors (up to 50) Copy
Lu S., Nishimura S., Ito M., Tsuchida T., Kakeya H. Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete Saccharothrix sp. and Their Structure–Activity Relationship // Journal of Natural Products. 2016. Vol. 79. No. 7. pp. 1891-1895.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1021/acs.jnatprod.6b00372
UR - https://doi.org/10.1021%2Facs.jnatprod.6b00372
TI - Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete Saccharothrix sp. and Their Structure–Activity Relationship
T2 - Journal of Natural Products
AU - Lu, Shan
AU - Ito, Masashi
AU - Tsuchida, Toshio
AU - Nishimura, Shin-ichi
AU - Kakeya, Hideaki
PY - 2016
DA - 2016/06/22 00:00:00
PB - American Chemical Society (ACS)
SP - 1891-1895
IS - 7
VL - 79
SN - 0163-3864
SN - 1520-6025
ER -
BibTex |
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BibTex Copy
@article{2016_Lu,
author = {Shan Lu and Masashi Ito and Toshio Tsuchida and Shin-ichi Nishimura and Hideaki Kakeya},
title = {Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete Saccharothrix sp. and Their Structure–Activity Relationship},
journal = {Journal of Natural Products},
year = {2016},
volume = {79},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021%2Facs.jnatprod.6b00372},
number = {7},
pages = {1891--1895},
doi = {10.1021/acs.jnatprod.6b00372}
}
MLA
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MLA Copy
Lu, Shan, et al. “Isolation and Structure Elucidation of Cytotoxic Saccharothriolides D to F from a Rare Actinomycete Saccharothrix sp. and Their Structure–Activity Relationship.” Journal of Natural Products, vol. 79, no. 7, Jun. 2016, pp. 1891-1895. https://doi.org/10.1021%2Facs.jnatprod.6b00372.
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