Nodulisporic acids D-F: structure, biological activities, and biogenetic relationships

Journal of Natural Products
Sheo B SinghJan S Tkacz

Abstract

Nodulisporic acids D, E, and F are the newest members of a family of nontremorogenic indole-diterpenoids that are potent, orally bioavailable, antiflea agents derived from a fungus belonging to the genus Nodulisporium. The four members of the D series are each devoid of an isoprene residue that is present at C-26 in the three nodulisporic acids described originally (the A series). Nodulisporic acid E (11a) has a simpler structure, which lacks not only the isoprene residue at C-26 but also two that form the A/B rings. Nodulisporic acid F is the simplest of all nodulisporic acids and is devoid of all three isoprene residues of the indole unit; as such, it represents the earliest biosynthetic intermediate in this series. A biogenetic grid based on mutation studies is proposed that encompasses all the known nodulisporic acids. Structure-activity relationships of the known natural nodulisporic acids have been elucidated. Within a series the most active compound possesses a dienoic acid chain, and overall, the end product of the biogenetic grid, i.e., nodulisporic acid A, exhibits the most potent antiflea activity. Additionally, the stereochemistries of C-3' ' and C-4' ' of nodulisporic acid D(2) and therefore of nodulisporic acids A...Continue Reading

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Citations

Mar 26, 2013·Applied Microbiology and Biotechnology·Chengwei LiuTohru Dairi
Oct 5, 2007·Journal of the American Chemical Society·Yang S Tran, Ohyun Kwon
Mar 15, 2013·Organic Letters·Ronald BesandreJeremy A May
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Jan 13, 2018·Genome Announcements·Matthew J NicholsonEmily J Parker
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Feb 13, 2021·Bioscience, Biotechnology, and Biochemistry·Masaru Enomoto
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