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Penipyridones A-F, Pyridone Alkaloids from Penicillium funiculosum.
J Nat Prod. 2016 07 22; 79(7):1783-90.JN

Abstract

Six new pyridone alkaloids, named penipyridones A-F (1-6), were isolated from the fermentation broth of an Antarctic moss-derived fungus, Penicillium funiculosum GWT2-24. Their structures were elucidated from extensive NMR and MS data. Although they possess the same major chromophore and some of them presented almost mirror ECD spectra, their absolute configurations were found to be uniformly S, as evidenced by X-ray single-crystal diffraction analysis, stereocontrolled total synthesis, and chemical conversions. TDDFT-ECD calculations of compounds 3 and 6 revealed that subtle conformational changes are responsible for the significantly different ECD curves. None of the compounds were cytotoxic (IC50 > 50 μM), while compounds 1, 2, 5, and 7 elicited lipid-lowering activity in HepG2 hepatocytes.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhou H
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
Li L
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
Wu C
Pharmacology and Toxicology Research Center, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College , Beijing 100193, People's Republic of China.
Kurtán T
Department of Organic Chemistry, University of Debrecen , POB 20, 4010 Debrecen, Hungary.
Mándi A
Department of Organic Chemistry, University of Debrecen , POB 20, 4010 Debrecen, Hungary.
Liu Y
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
Gu Q
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
Zhu T
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.
Guo P
Pharmacology and Toxicology Research Center, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College , Beijing 100193, People's Republic of China.
Li D
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao 266003, People's Republic of China.

MeSH

AlkaloidsAntarctic RegionsCrystallography, X-RayHep G2 CellsHumansHypolipidemic AgentsMolecular ConformationMolecular StructureNuclear Magnetic Resonance, BiomolecularPenicilliumPyridones

Pub Type(s)

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

Language

eng

PubMed ID

27359163

Citation

Zhou, Haibo, et al. "Penipyridones A-F, Pyridone Alkaloids From Penicillium Funiculosum." Journal of Natural Products, vol. 79, no. 7, 2016, pp. 1783-90.
Zhou H, Li L, Wu C, et al. Penipyridones A-F, Pyridone Alkaloids from Penicillium funiculosum. J Nat Prod. 2016;79(7):1783-90.
Zhou, H., Li, L., Wu, C., Kurtán, T., Mándi, A., Liu, Y., Gu, Q., Zhu, T., Guo, P., & Li, D. (2016). Penipyridones A-F, Pyridone Alkaloids from Penicillium funiculosum. Journal of Natural Products, 79(7), 1783-90. https://doi.org/10.1021/acs.jnatprod.6b00218
Zhou H, et al. Penipyridones A-F, Pyridone Alkaloids From Penicillium Funiculosum. J Nat Prod. 2016 07 22;79(7):1783-90. PubMed PMID: 27359163.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Penipyridones A-F, Pyridone Alkaloids from Penicillium funiculosum. AU - Zhou,Haibo, AU - Li,Liyuan, AU - Wu,Chongming, AU - Kurtán,Tibor, AU - Mándi,Attila, AU - Liu,Yankai, AU - Gu,Qianqun, AU - Zhu,Tianjiao, AU - Guo,Peng, AU - Li,Dehai, Y1 - 2016/06/30/ PY - 2016/7/1/entrez PY - 2016/7/1/pubmed PY - 2017/5/11/medline SP - 1783 EP - 90 JF - Journal of natural products JO - J Nat Prod VL - 79 IS - 7 N2 - Six new pyridone alkaloids, named penipyridones A-F (1-6), were isolated from the fermentation broth of an Antarctic moss-derived fungus, Penicillium funiculosum GWT2-24. Their structures were elucidated from extensive NMR and MS data. Although they possess the same major chromophore and some of them presented almost mirror ECD spectra, their absolute configurations were found to be uniformly S, as evidenced by X-ray single-crystal diffraction analysis, stereocontrolled total synthesis, and chemical conversions. TDDFT-ECD calculations of compounds 3 and 6 revealed that subtle conformational changes are responsible for the significantly different ECD curves. None of the compounds were cytotoxic (IC50 > 50 μM), while compounds 1, 2, 5, and 7 elicited lipid-lowering activity in HepG2 hepatocytes. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/27359163/Penipyridones_A_F_Pyridone_Alkaloids_from_Penicillium_funiculosum_ DB - PRIME DP - Unbound Medicine ER -