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Oxidation of the Phytoalexin Maackiain to 6,6-dihydroxy-maackiain by Colletotrichum Gloeosporioides

Oxidation of the Phytoalexin Maackiain to 6,6-dihydroxy-maackiain by Colletotrichum Gloeosporioides

S Soby, R Bates, H van Etten

Phytochemistry. 1997 Jul;45(5):925-9.

PMID: 9214775

Abstract:

Phytoalexins are low molecular weight antibiotic compounds produced by plants in response to infection by microbes. These antimicrobial compounds are thought to provide resistance to microbial invasion and colonization. (-)Maackiain and its pterocarpan relatives can be oxidized at a number of sites, including at the 6 carbon. A previously unknown metabolite was produced for (-)maackiain by the broad host-range pathogen Colletotrichum gloeosporioides (Glomerella cingulata). This unknown was identified by LC-MS-MS and NMR spectroscopy to be 6,6a-di-OH-maackiain (3,6,6a-trihydroxy-8,9,methylenedioxy-pterocarpan). It is produced by isolates that represent all four races and pathotypes of C. gloeosporioides isolated from the tropical forage legume Stylosanthes spp. We present evidence that the primary metabolite (-)6a-OH-maackiain is subsequently hydroxylated at carbon 6, a step resulting in a compound that is increased in polarity and decreased in toxicity relative to the parent compound and (-)6a-OH-maackiain. This further oxidation may be required for efficient excretion or carbon source scavenging.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2035156	(−)-Maackiain		2035-15-6	Price

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