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alpha-Pyrones with Diverse Hydroxy Substitutions from Three Marine-Derived Nocardiopsis Strains
Zhang, Haibo; Saurav, Kumar; Yu, Ziquan; Mandi, Attila; Kurtan, Tibor; Li, Jie; Tian, Xinpeng; Zhang, Qingbo; Zhang, Wenjun; Zhang, Changsheng; Zhang, CS (reprint author), Chinese Acad Sci, CAS Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med, RNAM Ctr Marine Microbiol,South China Sea Inst Oc, 164 West Xingang Rd, Guangzhou 510301, Guangdong, Peoples R China.
2016
Source PublicationJOURNAL OF NATURAL PRODUCTS
Volume79Issue:6Pages:1610-1618
AbstractEight new alpha-pyrones 1-8 and three known alpha-pyrones 9-11 were isolated from three marine-derived Nocardiopsis strains SCSIO 10419, SCSIO 04583, and SCSIO KS107. The structures of compounds 1-8 were elucidated by comprehensive spectral analyses. The absolute configurations of 4-deoxyphomapyrone C (1), 4-deoxy-11-hydroxyphomapyrone C (3), 4-deoxy-7R-hydroxyphomapyrone C (5), and phomapyrone C (11) were determined by TDDFT-ECD calculations for the solution conformers, which revealed that the conformation of the side chain was decisive for the sign of the characteristic high-wavelength ECD transition. (-)-4-Deoxy-8-hydroxyphomapyrone C (4) was isolated from SCSIO 10419 and was deduced as a diastereomeric mixture containing (8S)- and (8R)-4-deoxy-8-hydroxyphomapyrone C in a ratio of 2.6:1 (8R:8S), by chiral phase HPLC analysis and Mosher's ester analysis. Interestingly, 7-hydroxymucidone (9) was isolated from both SCSIO 04583 and SCSIO KS107, as an enantiomeric mixture containing (7S)-hydroxymucidone (major in 9 from SCSIO 04583) and (7R)-hydroxymucidone (major in 9 from SCSIO KS107). alpha-Pyrones 3-5 were identified as three isomers of phomapyrone C (II) with diverse hydroxy substitutions. alpha-Pyrones 10-hydroxymucidone (6), 4-hydroxymucidone (8), and 9, differed in the position of the hydroxy group. Several alpha-pyrones exhibited moderate growth inhibitory activity against Micrococcus luteus and Bacillus subtilis.
Department[Zhang, Haibo; Saurav, Kumar; Yu, Ziquan; Li, Jie; Tian, Xinpeng; Zhang, Qingbo; Zhang, Wenjun; Zhang, Changsheng] Chinese Acad Sci, CAS Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med, RNAM Ctr Marine Microbiol,South China Sea Inst Oc, 164 West Xingang Rd, Guangzhou 510301, Guangdong, Peoples R China; [Yu, Ziquan] Hunan Normal Univ, Sch Life Sci, 36 Lushan Rd, Changsha 410081, Hunan, Peoples R China; [Mandi, Attila; Kurtan, Tibor] Univ Debrecen, Dept Organ Chem, POB 400, H-4002 Debrecen, Hungary ; LMB
Subject AreaPlant Sciences ; Pharmacology & Pharmacy
Document Type期刊论文
Identifierhttp://ir.scsio.ac.cn/handle/344004/15404
Collection中科院海洋生物资源可持续利用重点实验室
Corresponding AuthorZhang, CS (reprint author), Chinese Acad Sci, CAS Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med, RNAM Ctr Marine Microbiol,South China Sea Inst Oc, 164 West Xingang Rd, Guangzhou 510301, Guangdong, Peoples R China.
Recommended Citation
GB/T 7714
Zhang, Haibo,Saurav, Kumar,Yu, Ziquan,et al. alpha-Pyrones with Diverse Hydroxy Substitutions from Three Marine-Derived Nocardiopsis Strains[J]. JOURNAL OF NATURAL PRODUCTS,2016,79(6):1610-1618.
APA Zhang, Haibo.,Saurav, Kumar.,Yu, Ziquan.,Mandi, Attila.,Kurtan, Tibor.,...&Zhang, CS .(2016).alpha-Pyrones with Diverse Hydroxy Substitutions from Three Marine-Derived Nocardiopsis Strains.JOURNAL OF NATURAL PRODUCTS,79(6),1610-1618.
MLA Zhang, Haibo,et al."alpha-Pyrones with Diverse Hydroxy Substitutions from Three Marine-Derived Nocardiopsis Strains".JOURNAL OF NATURAL PRODUCTS 79.6(2016):1610-1618.
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