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Molecules 2016, 21(11), 1438; doi:10.3390/molecules21111438

Penicitroamide, an Antimicrobial Metabolite with High Carbonylization from the Endophytic Fungus Penicillium sp. (NO. 24)

1
Hubei Key Laboratory of Natural Product Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002, China
2
Institut für Pharmazeutische Biologie und Biotechnologie, Heirich-Heine University Dusseldorf, Universitätsstr. 1, Gebäude 26.23, Dusseldorf 40225, Germany
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 5 September 2016 / Revised: 21 October 2016 / Accepted: 25 October 2016 / Published: 28 October 2016
(This article belongs to the Special Issue Diversity of Alkaloids)
View Full-Text   |   Download PDF [1061 KB, uploaded 28 October 2016]   |  

Abstract

Penicitroamide (1), a new metabolite with a new framework, was isolated from the ethyl acetate extract of the PDB (Potato Dextrose Broth) medium of Penicillium sp. (NO. 24). The endophytic fungus Penicillium sp. (NO. 24) was obtained from the healthy leaves of Tapiscia sinensis Oliv. The structure of penicitroamide (1) features a bicyclo[3.2.1]octane core unit with a high degree of carbonylization (four carbonyl groups and one enol group). The chemical structure of penicitroamide (1) was elucidated by analysis of 1D-, 2D-NMR and MS data. In bioassays, penicitroamide (1) displayed antibacterial potency against two plant pathogens, Erwinia carotovora subsp. Carotovora (Jones) Bersey, et al. and Sclerotium rolfsii Sacc. with MIC50 at 45 and 50 μg/mL. Compound 1 also showed 60% lethality against brine shrimp at 10 μg/mL. Penicitroamide (1) exhibited no significant activity against A549, Caski, HepG2 and MCF-7 cells with IC50 > 50 μg/mL. Finally, the possible biosynthetic pathway of penicitroamide (1) was discussed. View Full-Text
Keywords: endophytic fungus; penicitroamide; Penicillium sp.; antibacterial activity; brine shrimp lethality endophytic fungus; penicitroamide; Penicillium sp.; antibacterial activity; brine shrimp lethality
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MDPI and ACS Style

Feng, Z.-W.; Lv, M.-M.; Li, X.-S.; Zhang, L.; Liu, C.-X.; Guo, Z.-Y.; Deng, Z.-S.; Zou, K.; Proksch, P. Penicitroamide, an Antimicrobial Metabolite with High Carbonylization from the Endophytic Fungus Penicillium sp. (NO. 24). Molecules 2016, 21, 1438.

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