Soraphen A

Description

Soraphen A was originally isolated from the culture broth of Sorangium cellulosum, a soil-dwelling myxobacterium, for its potent antifungal activity (Gerth et al. 1994, Gerth et al. 2003). This polyketide natural product contains an unsaturated 18-membered lactone ring, an extracyclic phenyl ring, 2 hydroxyl groups, 3 methyl groups, and 3 methoxy groups (Bedorf et al. 1993, Ligon et al. 2002) . There is also a 6-membered ring within the macrocycle formed by a hemiketal between the C3 carbonyl and C7 hydroxyl.

Uses

Soraphen A, an inhibitor of acetyl CoA carboxylase activity, interferes with fatty acid elongation. It has demonstrated strong promise as a broad-spectrum fungicide against various plant pathogenic fungi (Pridzun et al. 1995).

Definition

ChEBI: Soraphen A is a macrolide and an agent highly effective against plant-pathogenic fungi. It was extensively researched for agricultural use until it was discovered to be a teratogen. It has a role as a bacterial metabolite, an EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor and a teratogenic agent. It is a macrolide, an ether, a cyclic hemiketal and an olefinic compound.

References

Total Synthesis of the Acetyl CoA Carboxylase Inhibitor Soraphen A: Asymmetric Tsuji Reduction Enables Successive Olefin Metathesis. DOI:10.1021/jacs.1c12063
Soraphen A, an inhibitor of acetyl CoA carboxylase activity, interferes with fatty acid elongation. DOI:10.1016/j.bcp.2010.12.014
https://www.cell.com/fulltext/S1097-2765(04)00725-7

Raw materials

Preparation Products