A mini-review on oxysporone

Trends in Phytochemical Research

مقاله 2، دوره 1، شماره 2، شهریور 2017، صفحه 55-60   

نوع مقاله: Review article

نویسندگان

Satyajit D. Sarker^{* 1}؛ Lutfun Nahar¹؛ Tauhidur Rahman Nurunnabi^{1، 2}؛ S.M. Mahbubur Rahman²؛ Md. Hossain Sohrab³؛ Md. Morsaline Billah²؛ Fyaz M. D. Ismail¹؛ George P. Sharples¹

¹Medicinal Chemistry and Natural Products Research Group, School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, James Parsons Building, Byrom Street, Liverpool L3 3AF, United Kingdom

²Biotechnology and Genetic Engineering Discipline, Khulna University, Khulna, Bangladesh

³Pharmaceutical Sciences Research Division, BCSIR Laboratories, Dhaka

چکیده

Oxysporone, possessing a 4H-furo(2,3-b)pyran-2(3H)-one structure, is a fungal metabolite, first isolated from Fusarium oxysporum. Later, this compound was also reported from the fungal genera, Diplodia, Pestalotia and Pestalotiopsis. Oxysporone was patented as an antibiotic for the treatment of dysentery, and its phytotoxic property has been well-established. Interesting biological and chemical properties of oxysporone make this compound attractive for its potential biotechnological applications in agriculture, especially as a new agrochemical with a lower environmental impact. However, it requires further extensive bioactivity screening looking at beyond its established phytotoxicity and preliminary antifungal property. It has a simple chemical structure (C₇H₈O₄), and the hydroxyl group at C-4 provides options for synthesising numerous analogues by simply incorporating various functionalities at C-4, whilst keeping the main skeleton intact. This mini-review provides a critical overview on the occurrence, production, synthesis, structure elucidation and bioactivities of oxysporone.

کلیدواژه‌ها

Bioactivities؛ Fungal metabolite؛ Fusarium oxysporum؛ Oxysporone؛ Phytotoxicity؛ Structure elucidation

مراجع

Adesogan, E. K., Alo, B. I., 1979. Oxysporone, a new metabolites from Fusarium oxysporum. Phytochemistry 18, 1886-1887.

Andolfi, A., Maddau, L., Linaldeddu, B. T., Scanu, B., Cimmino, A., Basso, S., Evidente, A., 2014. Bioactivity studies of oxysporone and several derivatives. Phytochem. Lett. 10, 40-45.

Brian, P. W., Curtis, P. J, Heming, H. G., 1946. A substance causing abnormal development of fungal hyphae produced by Penicillium janczewskii Zal. Trans. Brit. Mycol. Soc. 29, 173.

Evidente, A., Masi, M., Linaldeddu, B. T., Franceschini, A., Scanu, B., Cimmino, A., Andolfi, A., Motta, A., Maddau, L., 2012. Afritoxinones A and B, dihydrofuropyran-2-ones produced by Diplodia africana, the causal agent of branch dieback on Juniperus phoenicea. Phytochemistry 77, 245-250.

Hirota, A., Horikawa, T., Fujiwara, A., 1993. Isolation of phenylacetic acid from a phytopathogenic fungus Glomerella cingulate. Biosci. Biotech. Biochem. 57 (3), 492.

Luo, D. Q., Zhang, L., Shi, B. Z., Song, X. M., 2012. Two new oxysporone derivatives from the fermentation broth of the endophytic plant fungus Pestalotiopsis karstenii isolated from stems of Camellia sasanqua. Molecules 17, 8554-8560.

Mazzeo, G., Santoro, E., Andolfi, A., Cimmino, A., Troselj, P., Petrovic, A. G., Superchi, S., Evidente, A., Berova, N., 2013. Absolute configurations of fungal and plant metabolites by chiroptical methods. ORD, ECD, and VCD studies on phyllostin, scytolide, and oxysporone. J. Nat. Prod. 76, 588-599.

Nagata, T., Ando, Y., 1989. Oxysporone, a phytotoxin isolated from tea gray blight fungus Pestalotia longiseta. Agric. Biol. Chem. 53 (10), 2811.

VanderMolen, K. M., Raja, H. A., El-Elimat, T., Oberlies, N. H., 2013. Evaluation of culture media for the production of secondary metabolites in a natural products screening program. AMB Express 3, 71-90.

Venkatasubbaiah, P., Van Dyke, C. G., Chilton, W. S., 1991. Phytotoxins produced by Pestalotiopsis oenotheare, a pathogen of evening primrose. Phytochemistry 30 (5), 1471-1474.