Journal
JOURNAL OF NATURAL PRODUCTS
Volume 75, Issue 2, Pages 175-180Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np2007044
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Funding
- National Science Foundation [DMR-0225180]
- National Institutes of Health [RR-01646]
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Metarhizium acridum, an entomopathogenic fungus, has been commercialized and used successfully for biocontrol of grasshopper pests in Africa and Australia. Its conidia produce two novel 17-membered macrocycles, metacridamides A (1) and B (2), which consist of a Phe unit condensed with a nonaketide. Planar structures were elucidated by a combination of mass spectrometric and NMR techniques. Following hydrolysis of 1, chiral amino acid analysis assigned the L-configuration to the Phe unit. A crystal structure established the absolute configuration of the eight remaining stereogenic centers in 1. Metacridamide A (1) showed cytotoxicity to three cancer lines with IC50's of 6.2, 11.0, and 10.8 mu M against Caco-2 (epithelial colorectal adenocarcinoma), MCF-7 (breast cancer), and HepG2/C3A (hepatoma) cell lines, respectively. In addition, metacridamide B (2) had an IC50 of 18.2 mu M against HepG2/C3A, although it was inactive at 100 mu M against Caco-2 and MCF-7. Neither analogue showed antimicrobial, phytotoxic, or insecticidal activity.
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