The Antifungal Activity of Widdrol and Its Biotransformation by Colletotrichum gloeosporioides (penz.) Penz. & Sacc. and Botrytis cinerea Pers.:  Fr

• Published in: Journal of agricultural and food chemistry Vol. 54; no. 20; pp. 7517 - 7521
• Main Authors: Nuñez, Yarelis Ortíz, Salabarria, Iraida Spengler, Collado, Isidro G, Hernández-Galán, Rosario
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 04.10.2006; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; antifungal properties; Benzocycloheptenes - metabolism; Benzocycloheptenes - pharmacology; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; biotransformation; Botrytis - drug effects; Botrytis - metabolism; Botrytis cinerea; chemical structure; Chemistry; Chemistry, Applied; Colletotrichum - drug effects; Colletotrichum - metabolism; Colletotrichum gloeosporioides; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Fungicides, Industrial - metabolism; Fungicides, Industrial - pharmacology; Glomerella cingulata; Juniperus; Juniperus lucayana; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; metabolic detoxification; metabolism; Methods. Procedures. Technologies; Physical Sciences; plant pathogenic fungi; Science & Technology; secondary metabolites; widdrol; biotransformation; CLOVANES; Colleotrichum gloeosporioides; Botrytis cinerea; antifungal activity; widdrol; Fungi; Antifungal agent; Biotransformation; Fungi Imperfecti; Colletotrichum gloeosporioides; Thallophyta
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf061436m

Widdrol (1) was tested against the necrotrophic plant pathogens Botrytis cinerea and Colletotrichum gloeosporioides. While 1 was found to be inactive against C. gloeosporioides, it showed a selective and effective control of B. cinerea, significantly inhibiting the mycelial growth of the fungus at concentrations of 100 ppm and above. In addition, the biotransformation of 1 by both fungi was studied. Incubation with C. gloeosporioides and B. cinerea afforded four and one biotransformation products (2−6), respectively. Biotransformation with C. gloeosporioides was highly regioselective, yielding for the most part oxidation products at C-10:  10-oxowiddrol (2), 10β-hydroxywiddrol (3), 10α-hydroxywiddrol (4), and 14α-hydroxywiddrol (5). The structures of all products were determined on the basis of their spectroscopic data, including coupling constants, two-dimensional NMR analysis (heteronuclear multiple quantum coherence, heteronuclear multiple bond correlation, and nuclear Overhauser enhancement spectroscopy), and nuclear Overhauser effect. The biotransformation products were then tested against B. cinerea and found to be inactive. These results shed further light on the structural modifications, which may be necessary to develop selective fungal control agents against B. cinerea. Keywords: Biotransformation; widdrol; Botrytis cinerea; Colleotrichum gloeosporioides; antifungal activity