5,5‐Dimethyloxazolidine‐2‐thione formation from glucosinolate inLimnanthes alba Benth. seed

Abstract

A crystalline compound, identified as 5,5-dimethyloxazolidine-2-thione was isolated from defatted Limnanthes alba vat. alba (meadowfoam) seed meal by either of two procedures, described below. The precursor glucosinolate was separated and then hydrolyzed with an added thioglucosidase prepared from mustard seed. Alternatively, endogenous thioglucosidase was allowed to act in an aqueous slurry of the Limnanthes alba meal, and subsequently 5,5-dimethyloxazolidine-2-thione was purifed from the autholysis products. Previous workers reported 5,5dimethyloxazolidine-2-thione formation in seed meals of only two Cruciferae genera. Among seed samples we analyzed representing the Limnanthaceae species, production of the rare oxazolidinethione derivative was unique to Limnanthes alba.

Glucosinolates in the new oilseed crop meadowfoam: natural variation in Section Inflexae of Limnanthes, a new glucosinolate in L. floccosa, and QTL analysis in L. alba

“…In general, different QTL controlled each class of glucosinolate and QTLs in leaf and seed material were not coincident, suggesting independent regulation of each class and each tissue. Genetic control of seed glucosinolate content in Limnanthes , however, may be less complex than in the brassicas, as aliphatic and indolic glucosinolates have not been reported except for small amounts of glucoconringiin (2‐methyl‐2‐hydroxypropyl glucosinolate) in some L. alba individuals (Daxenbichler and VanEtten 1974).…”

Transformation of the Glucosinolate-Derived Allelochemicals Allyl Isothiocyanate and Allylnitrile in Soil

“…Heterocyclic compounds are often produced in reactions between isothiocyanates and a nucleophilic reaction partner, either spontaneously or by additional external influence from a-mercapto acids or a-amino acids. Isothiocyanates with sufficiently acid a-hydrogen atoms react with aldehydes and ketones to produce 1,3oxazolidine-2-thiones (Daxenbichler and VanEtten, 1974). Thus, the isothiocyanate functional group can react with nucleophilic groups commonly found in organic matter and a negative correlation of AI half-life with soil organic matter concentration is expected.…”

Biodiesel from meadowfoam (Limnanthes alba L.) seed oil: oxidative stability and unusual fatty acid composition

“…39 Other agricultural byproducts from the processing of meadowfoam have been explored and reported. Agricultural feeding studies have been explored but defatted seed meal contains significant levels of glucosinolates 40 and would require detoxification prior to inclusion in livestock diets. 41 Other defatted seed meal applications include direct use as a soil amendment.…”