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Antibacterial sorbicillin and diketopiperazines from the endogenous fungus Penicillium sp. GD6 associated Chinese mangrove Bruguiera gymnorrhiza.
Chin J Nat Med. 2018 May; 16(5):358-365.CJ

Abstract

One new sorbicillin derivative, 2-deoxy-sohirnone C (1), one new diketopiperazine alkaloid, 5S-hydroxynorvaline-S-Ile (2), and two naturally occurring diketopiperazines, 3S-hydroxylcyclo(S-Pro-S-Phe) (3) and cyclo(S-Phe-S-Gln) (4), together with three known compounds were isolated from the Chinese mangrove endophytic fungus Penicillium sp. GD6. Their structures were determined on the basis of extensive spectroscopic analyses and by comparison with literature data. The absolute configuration of 3-hydroxyl moiety in 3 was determined by Mosher's method, while the absolute stereochemistry of 2 and 4 was established by comparison with the CD spectra of natural and synthesized diketopiperazines. Compound 1 showed moderate antibacterial activity against Methicillin-resistant Staphylococcus aureus with a MIC value of 80 μg·mL-1.

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Authors+Show Affiliations

Jiang CS
China State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; School of Biological Science and Technology, University of Jinan, Jinan 250022, China.
Zhou ZF
China State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
Yang XH
School of Life Science & Technology, China Pharmaceutical University, Nanjing 210009, China.
Lan LF
China State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China.
Gu YC
Syngenta Jealott's Hill International Research Centre, Berkshire RG42 6EY, United Kingdom.
Ye BP
School of Life Science & Technology, China Pharmaceutical University, Nanjing 210009, China. Electronic address: yebp@cpu.edu.cn.
Guo YW
China State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. Electronic address: ywguo@simm.ac.cn.

MeSH

AlkaloidsAnti-Bacterial AgentsChinaCircular DichroismDiketopiperazinesMethicillin-Resistant Staphylococcus aureusMicrobial Sensitivity TestsMolecular StructureNuclear Magnetic Resonance, BiomolecularPenicilliumResorcinolsRhizophoraceaeWetlands

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29860997

Citation

Jiang, Cheng-Shi, et al. "Antibacterial Sorbicillin and Diketopiperazines From the Endogenous Fungus Penicillium Sp. GD6 Associated Chinese Mangrove Bruguiera Gymnorrhiza." Chinese Journal of Natural Medicines, vol. 16, no. 5, 2018, pp. 358-365.
Jiang CS, Zhou ZF, Yang XH, et al. Antibacterial sorbicillin and diketopiperazines from the endogenous fungus Penicillium sp. GD6 associated Chinese mangrove Bruguiera gymnorrhiza. Chin J Nat Med. 2018;16(5):358-365.
Jiang, C. S., Zhou, Z. F., Yang, X. H., Lan, L. F., Gu, Y. C., Ye, B. P., & Guo, Y. W. (2018). Antibacterial sorbicillin and diketopiperazines from the endogenous fungus Penicillium sp. GD6 associated Chinese mangrove Bruguiera gymnorrhiza. Chinese Journal of Natural Medicines, 16(5), 358-365. https://doi.org/10.1016/S1875-5364(18)30068-2
Jiang CS, et al. Antibacterial Sorbicillin and Diketopiperazines From the Endogenous Fungus Penicillium Sp. GD6 Associated Chinese Mangrove Bruguiera Gymnorrhiza. Chin J Nat Med. 2018;16(5):358-365. PubMed PMID: 29860997.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antibacterial sorbicillin and diketopiperazines from the endogenous fungus Penicillium sp. GD6 associated Chinese mangrove Bruguiera gymnorrhiza. AU - Jiang,Cheng-Shi, AU - Zhou,Zhen-Fang, AU - Yang,Xiao-Hong, AU - Lan,Le-Fu, AU - Gu,Yu-Cheng, AU - Ye,Bo-Ping, AU - Guo,Yue-Wei, PY - 2017/05/10/received PY - 2018/6/5/entrez PY - 2018/6/5/pubmed PY - 2018/8/14/medline KW - Diketopiperazine alkaloids KW - Mangrove KW - Penicillium sp. KW - Sorbicillin derivative SP - 358 EP - 365 JF - Chinese journal of natural medicines JO - Chin J Nat Med VL - 16 IS - 5 N2 - One new sorbicillin derivative, 2-deoxy-sohirnone C (1), one new diketopiperazine alkaloid, 5S-hydroxynorvaline-S-Ile (2), and two naturally occurring diketopiperazines, 3S-hydroxylcyclo(S-Pro-S-Phe) (3) and cyclo(S-Phe-S-Gln) (4), together with three known compounds were isolated from the Chinese mangrove endophytic fungus Penicillium sp. GD6. Their structures were determined on the basis of extensive spectroscopic analyses and by comparison with literature data. The absolute configuration of 3-hydroxyl moiety in 3 was determined by Mosher's method, while the absolute stereochemistry of 2 and 4 was established by comparison with the CD spectra of natural and synthesized diketopiperazines. Compound 1 showed moderate antibacterial activity against Methicillin-resistant Staphylococcus aureus with a MIC value of 80 μg·mL-1. SN - 1875-5364 UR - https://www.unboundmedicine.com/medline/citation/29860997/Antibacterial_sorbicillin_and_diketopiperazines_from_the_endogenous_fungus_Penicillium_sp__GD6_associated_Chinese_mangrove_Bruguiera_gymnorrhiza_ DB - PRIME DP - Unbound Medicine ER -