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Zeng LW, Zhou CX, Liu JD, et al. Design, synthesis, and antimicrobial activities of new tanshinone IIA esters. Nat Prod Res. 2016;30(23):2662-2668doi: 10.1080/14786419.2016.1138302.
Zeng, L. W., Zhou, C. X., Liu, J. D., Liu, C. H., Mo, J. X., Hou, A. F., Yao, W., Wang, Z. Z., & Gan, L. S. (2016). Design, synthesis, and antimicrobial activities of new tanshinone IIA esters. Natural product research, 30(23), 2662-2668. https://doi.org/10.1080/14786419.2016.1138302
Zeng, Lin-Wei, et al. "Design, synthesis, and antimicrobial activities of new tanshinone IIA esters." Natural product research vol. 30,23 (2016): 2662-2668. doi: https://doi.org/10.1080/14786419.2016.1138302
Zeng LW, Zhou CX, Liu JD, Liu CH, Mo JX, Hou AF, Yao W, Wang ZZ, Gan LS. Design, synthesis, and antimicrobial activities of new tanshinone IIA esters. Nat Prod Res. 2016 Dec;30(23):2662-2668. doi: 10.1080/14786419.2016.1138302. Epub 2016 Feb 01. PMID: 26829106.
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Nat Prod Res. 2016 Dec;30(23):2662-2668. doi: 10.1080/14786419.2016.1138302. Epub 2016 Feb 01.

Design, synthesis, and antimicrobial activities of new tanshinone IIA esters.

Natural product research

Lin-Wei Zeng, Chang-Xin Zhou, Jia-Dong Liu, Chang-Hong Liu, Jian-Xia Mo, A-Fang Hou, Wei Yao, Zhen-Zhen Wang, Li-She Gan

Affiliations

  1. a College of Pharmaceutical Sciences , Zhejiang University , Hangzhou , P.R. China.
  2. b State Key Lab of Pharmaceutical Biotechnology, School of Life Sciences , Nanjing University , Nanjing , P.R. China.
  3. c Zhejiang Chemical Industry Research Institute Co. Ltd , Hangzhou , P.R. China.

PMID: 26829106 DOI: 10.1080/14786419.2016.1138302

Abstract

Sixteen new ester derivatives with various partition coefficient (ClogP) values of tanshinone IIA (TSIIA), a major lipophilic component of Salvia miltiorrhiza, were designed and synthesised, including six aliphatic esters (3a-e, 5a), one phosphate ester (4c) and nine aromatic esters (5b-j). Their antimicrobial activities against three Gram-positive bacteria strains, Staphylococcus aureus, Bacillus subtilis, and Bacillus amyloliquefaciens, and two Gram-negative bacteria strains, Pseudomonas aeruginosa and Escherichia coli, as well as two fungi species, Candida albicans and Saccharomyces cerevisiae, were evaluated in vitro by broth microdilution susceptibility tests. The results showed that keeping ClogP values in a certain range is necessary for their antimicrobial activities. For those compounds with ClogP values between 5 and 10, their MIC values showed positive correlations with ClogP values. In particular, compound 3e exhibited fourfold and twofold higher potency than the standard drug amphotericin B against fungi C. albicans and S. cerevisiae with MIC values of 1.95 and 7.81 μg/mL, respectively.

Keywords: ClogP; Tanshinone IIA; antimicrobial; ester derivatives; synthesis

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