Structures and Absolute Configurations of Penicillactones A–C from an Endophytic Microorganism, Penicillium dangeardii Pitt

Penicillactones A–C (1–3) are structurally related natural products with a spirocyclic anhydride structure and were isolated from the endophytic fungus Penicillium dangeardii Pitt. Penicillactones B and C showed inhibition of the release of β-glucuronidase from polymorphonuclear leukocytes with ED50...

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Veröffentlicht in:	Organic letters 2013-10, Vol.15 (20), p.5206-5209
Hauptverfasser:	Liu, Yunbao, Ding, Guangzhi, Li, Yong, Qu, Jing, Ma, Shuanggang, Lv, Haining, Liu, Yang, Wang, Wenjie, Dai, Jungui, Tang, Yi, Yu, Shishan
Format:	Artikel
Sprache:	eng
Schlagworte:	Dose-Response Relationship, Drug Enzyme Inhibitors - chemistry Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology Glucuronidase - antagonists & inhibitors Glucuronidase - metabolism Humans Lactones - chemistry Lactones - isolation & purification Models, Molecular Molecular Structure Neutrophils - enzymology Neutrophils - metabolism Penicillium - chemistry Spiro Compounds - chemistry Spiro Compounds - isolation & purification Stereoisomerism Structure-Activity Relationship
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Zusammenfassung:	Penicillactones A–C (1–3) are structurally related natural products with a spirocyclic anhydride structure and were isolated from the endophytic fungus Penicillium dangeardii Pitt. Penicillactones B and C showed inhibition of the release of β-glucuronidase from polymorphonuclear leukocytes with ED50 values of 2.58 and 1.57 μM. A 2D INADEQUATE experiment of 1 was performed at natural abundance to confirm the arrangement of its carbon skeleton. The configurations of 1–3 were established through extensive NMR spectroscopic analysis, selective structural modifications, and CD analysis.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol4023485