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Studies on the Biosynthesis of Iridals and Cycloiridals
Author(s) -
Marner FranzJosef,
Gladtke Dieter,
Jaenicke Lothar
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710544
Subject(s) - chemistry , squalene , methylation , stereochemistry , moiety , rhizome , biosynthesis , methionine , bicyclic molecule , terpenoid , methyl group , side chain , demethylation , biochemistry , organic chemistry , group (periodic table) , enzyme , dna methylation , dna , gene , botany , amino acid , biology , polymer , gene expression
The incorporation of [2‐ 14 C]acetate, [2‐ 14 C]mevalonate, and [ 3 H]squalene proved the squalenoid nature of the iridals, novel triterpenoids from rhizomes of swordlilies. Methionine is readily incorporated into cycloiridalls of Iris pallida dalmatica , thus indicating that the methylation of iridals via S ‐adenosyl‐L‐methionine leads to the formation of the irone moiety of the bicyclic compounds. The 3 H/ 14 C ratio of the transferred labelled methyl group remained unchanged. Therefore, the methylation/cyclization of the terpenoid side chain of iridals must proceed by a concerted mechanism without formation of a cyclopropanoid intermediate.
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