Pestalazines and Pestalamides, Bioactive Metabolites from the Plant Pathogenic Fungus Pestalotiopsis theae

Pestalazines A (1) and B (2), two new diketopiperazine heterodimers, and pestalamides A−C (3−5), three new amides, have been isolated from cultures of the plant pathogenic fungus Pestalotiopsis theae. The structures of these compounds were elucidated mainly by NMR spectroscopy. The absolute configur...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2008-11, Vol.71 (11), p.1861-1865
Main Authors: Ding, Gang, Jiang, Lihua, Guo, Liangdong, Chen, Xulin, Zhang, Hua, Che, Yongsheng
Format: Article
Language:English
Subjects:
amides
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Anti-HIV Agents - pharmacology
antifungal properties
antiviral properties
Ascomycota - chemistry
asperazine
Aspergillus fumigatus
Aspergillus fumigatus - drug effects
aspernigrin
bioactive properties
Biological and medical sciences
Camellia sinensis
Camellia sinensis - microbiology
carbonarone
chemical structure
Diketopiperazines - chemistry
Diketopiperazines - isolation & purification
Diketopiperazines - pharmacology
General pharmacology
Human immunodeficiency virus 1
Humans
Indole Alkaloids - chemistry
Indole Alkaloids - isolation & purification
Indole Alkaloids - pharmacology
Medical sciences
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
pestalamides
pestalazines
Pestalotiopsis
Pestalotiopsis theae
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
piperazine
plant pathogenic fungi
spectral analysis
virus replication
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Summary:Pestalazines A (1) and B (2), two new diketopiperazine heterodimers, and pestalamides A−C (3−5), three new amides, have been isolated from cultures of the plant pathogenic fungus Pestalotiopsis theae. The structures of these compounds were elucidated mainly by NMR spectroscopy. The absolute configurations of 1 and 2 were determined using Marfey’s method on their acid hydrolysates and by comparison of their CD spectra with that of a model compound. Compounds 1, 3, and 6 displayed inhibitory effects on HIV-1 replication in C8166 cells. Compound 3 also showed potent antifungal activity against Aspergillus fumigatus.
ISSN:0163-3864
1520-6025
DOI:10.1021/np800357g