title: A putative precursor of isomalabaricane triterpenoids from lanosterol synthase mutants.
abstract: [reaction: see text]. Known lanosterol synthase mutants produce monocyclic or tetracyclic byproducts from oxidosqualene. We describe Erg7 Tyr510 mutants that cause partial substrate misfolding and generate a tricyclic byproduct. This novel triterpene, (13alphaH)-isomalabarica-14(27),17E,21-trien-3beta-ol, is the likely biosynthetic precursor of isomalabaricane triterpenoids in sponges. The results suggest the facile evolution of protective triterpenoids in sessile animals.
authors.affiliation: Department of Chemistry and Department of Biochemistry and Cell Biology, Rice University, 6100 South Main Street, Houston, Texas 77005, USA.
authors.forename: Silvia
authors.initials: S
authors.lastname: Lodeiro
authors.forename: William K
authors.initials: WK
authors.lastname: Wilson
authors.forename: Hui
authors.initials: H
authors.lastname: Shan
authors.forename: Seiichi P T
authors.initials: SP
authors.lastname: Matsuda
mesh_terms: D000818:Animals; D005075:Biological Evolution; D000075202:Contraindications; D019751:Intramolecular Transferases / Q000235:genetics* / Q000378:metabolism*; D015394:Molecular Structure; D009154:Mutation; D011161:Porifera / Q000737:chemistry*; D013185:Squalene / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification
chemical_list: C514122:(13alphaH)-isomalabarica-14(27),17E,21-trien-3beta-ol; C002821:2,3-oxidosqualene; D014315:Triterpenes; D013185:Squalene; D019751:Intramolecular Transferases; C021924:lanosterol synthase