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Antimicrobial Phenolic Bisabolanes and Related Derivatives from Penicillium aculeatum SD-321, a Deep Sea Sediment-Derived Fungus.
J Nat Prod. 2015 Apr 24; 78(4):844-9.JN

Abstract

Three new phenolic bisabolane sesquiterpenes, peniciaculins A (1) and B (2) and (7S)-(-)-10-hydroxysydonic acid (3), together with a new nor-bisabolane derivative, 1-hydroxyboivinianin A (4), as well as six known bisabolanes (5-10), were identified from the culture of Penicillium aculeatum SD-321, a fungus isolated from deep-sea sediments. The structures of these compounds were mainly determined by analysis of spectroscopic data, and the absolute configurations of compounds 1-4 were established by comparing their ECD spectra with those of known analogues or by TDDFT-ECD calculations. Compound 1 represents the first example of a bisabolane analogue linked to a diphenyl ether moiety via an ether bond, while compound 2 appears to be the first dimeric bisabolane analogue where the two monomers are coupled to each other via an ester bond. The isolated compounds were evaluated for antimicrobial activity against 10 human and aquatic pathogenic bacteria and three plant-pathogenic fungi.

Authors+Show Affiliations

†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China. ‡University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, People's Republic of China.†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China. ‡University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, People's Republic of China.†Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25763602

Citation

Li, Xiao-Dong, et al. "Antimicrobial Phenolic Bisabolanes and Related Derivatives From Penicillium Aculeatum SD-321, a Deep Sea Sediment-Derived Fungus." Journal of Natural Products, vol. 78, no. 4, 2015, pp. 844-9.
Li XD, Li XM, Xu GM, et al. Antimicrobial Phenolic Bisabolanes and Related Derivatives from Penicillium aculeatum SD-321, a Deep Sea Sediment-Derived Fungus. J Nat Prod. 2015;78(4):844-9.
Li, X. D., Li, X. M., Xu, G. M., Zhang, P., & Wang, B. G. (2015). Antimicrobial Phenolic Bisabolanes and Related Derivatives from Penicillium aculeatum SD-321, a Deep Sea Sediment-Derived Fungus. Journal of Natural Products, 78(4), 844-9. https://doi.org/10.1021/acs.jnatprod.5b00004
Li XD, et al. Antimicrobial Phenolic Bisabolanes and Related Derivatives From Penicillium Aculeatum SD-321, a Deep Sea Sediment-Derived Fungus. J Nat Prod. 2015 Apr 24;78(4):844-9. PubMed PMID: 25763602.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antimicrobial Phenolic Bisabolanes and Related Derivatives from Penicillium aculeatum SD-321, a Deep Sea Sediment-Derived Fungus. AU - Li,Xiao-Dong, AU - Li,Xiao-Ming, AU - Xu,Gang-Ming, AU - Zhang,Peng, AU - Wang,Bin-Gui, Y1 - 2015/03/12/ PY - 2015/3/13/entrez PY - 2015/3/13/pubmed PY - 2015/9/4/medline SP - 844 EP - 9 JF - Journal of natural products JO - J Nat Prod VL - 78 IS - 4 N2 - Three new phenolic bisabolane sesquiterpenes, peniciaculins A (1) and B (2) and (7S)-(-)-10-hydroxysydonic acid (3), together with a new nor-bisabolane derivative, 1-hydroxyboivinianin A (4), as well as six known bisabolanes (5-10), were identified from the culture of Penicillium aculeatum SD-321, a fungus isolated from deep-sea sediments. The structures of these compounds were mainly determined by analysis of spectroscopic data, and the absolute configurations of compounds 1-4 were established by comparing their ECD spectra with those of known analogues or by TDDFT-ECD calculations. Compound 1 represents the first example of a bisabolane analogue linked to a diphenyl ether moiety via an ether bond, while compound 2 appears to be the first dimeric bisabolane analogue where the two monomers are coupled to each other via an ester bond. The isolated compounds were evaluated for antimicrobial activity against 10 human and aquatic pathogenic bacteria and three plant-pathogenic fungi. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/25763602/Antimicrobial_Phenolic_Bisabolanes_and_Related_Derivatives_from_Penicillium_aculeatum_SD_321_a_Deep_Sea_Sediment_Derived_Fungus_ DB - PRIME DP - Unbound Medicine ER -