Caryophyllene Sesquiterpenoids from a Fungicolous Isolate of Pestalotiopsis disseminata

• Published in: Journal of natural products (Washington, D.C.) Vol. 69; no. 4; pp. 608 - 611
• Main Authors: Deyrup, Stephen T, Swenson, Dale C, Gloer, James B, Wicklow, Donald T
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.2006; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: 6-hydroxypunctaporonin; antibacterial properties; Antibiotics (antibacterial agents, antifungal agents); Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; antifungal properties; Applied microbiology; Ascomycota - chemistry; Aspergillus flavus - drug effects; Bacillus subtilis - drug effects; Biological and medical sciences; biological control agents; Candida albicans - drug effects; caryophyllene; chemical structure; Chemistry, Medicinal; Escherichia coli - drug effects; Fundamental and applied biological sciences. Psychology; fungal antagonists; Fusarium - drug effects; Life Sciences & Biomedicine; Microbiology; Molecular Structure; Pestalotiopsis; Pestalotiopsis disseminata; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; sesquiterpenoids; spectral analysis; Staphylococcus aureus - drug effects; stereochemistry; ALCOHOLS; FUNGUS PORONIA-PUNCTATA; METABOLITES; PENICILLIUM; TAXUS-BREVIFOLIA; ANALOGS; Terpenoid; Molecular structure; Tricyclic compound; X ray diffraction; In vitro; Pestalotiopsis; Biological activity; Fungi; Microbial origin; Gram positive bacteria; Sesquiterpenes; Absolute configuration; Isolation; Fungi Imperfecti; Polyol; Antibacterial agent; Thallophyta; Structural analysis; Crystalline structure
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np050460b

Three new caryophyllene-type sesquiterpene alcohols, 6-hydroxypunctaporonin E (1), 6-hydroxypunctaporonin B (2), and 6-hydroxypunctaporonin A (3), have been isolated from cultures of the fungicolous fungus Pestalotiopsis disseminata. The structures of 1−3 were determined mainly by analysis of 1D and 2D NMR data. The structure and absolute configuration of 6-hydroxypunctaporonin E (1) was confirmed through X-ray crystallographic analysis of its mono-bromobenzoate derivative. Compounds 1 and 2 showed activity against Gram-positive bacteria.