title: Structure and bioactivity of thiosulfinates resulting from suppression of lachrymatory factor synthase in onion.
abstract: In normal onion (Allium cepa), trans-S-1-propenyl-L-cysteine sulfoxide is transformed via 1-propenesulfenic acid into propanethial S-oxide, a lachrymatory factor, through successive reactions catalyzed by alliinase and lachrymatory factor synthase (LFS). A recent report showed that suppression of the LFS activity caused a dramatic increase in thiosulfinates previously reported as "zwiebelane isomers". After purification by recycle high-performance liquid chromatography and subsequent analyses, we established the planar structure of the putative "zwiebelane isomers" as S-3,4-dimethyl-5-hydroxythiolane-2-yl 1-propenethiosulfinate, in which two of the three molecules of 1-propenesulfenic acid involved in the formation gave the thiolane backbone, and the third molecule gave the thiosulfinate structure. Of at least three stereoisomers observed, one in the (2'R,3'R,4'R,5'R)-configuration was collected as an isolated fraction, and the other isomers were collected as a combined fraction because spontaneous tautomerization prevented further purification. Both fractions showed inhibitory activities against cyclooxygenase-1 and α-glucosidase in vitro.
authors: Somatech Center, House Foods Corporation, 1-4 Takanodai, Yotsukaido, Chiba, 284-0033, Japan. morihiro-aoyagi@house-wf.co.jp
authors: Morihiro
authors: M
authors: Aoyagi
authors: Takahiro
authors: T
authors: Kamoi
authors: Masahiro
authors: M
authors: Kato
authors: Hiroshi
authors: H
authors: Sasako
authors: Nobuaki
authors: N
authors: Tsuge
authors: Shinsuke
authors: S
authors: Imai
mesh_terms: D013437:Carbon-Sulfur Lyases / Q000378:metabolism; D051545:Cyclooxygenase 1; D016861:Cyclooxygenase Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D019746:Intramolecular Oxidoreductases / Q000037:antagonists & inhibitors*; D019697:Onions / Q000737:chemistry* / Q000201:enzymology*; D010975:Platelet Aggregation Inhibitors; D011993:Recombinant Fusion Proteins / Q000037:antagonists & inhibitors; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D016861:Cyclooxygenase Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D010975:Platelet Aggregation Inhibitors; D011993:Recombinant Fusion Proteins; D013441:Sulfinic Acids; C100040:thiosulfinic acids; D051545:Cyclooxygenase 1; D013437:Carbon-Sulfur Lyases; C019243:alliin lyase; D019746:Intramolecular Oxidoreductases; C570346:lachrymatory factor synthase, Allium cepa