Journal of Agricultural and Food Chemistry p. 1647 - 1653 (1995)
Update date:2022-08-04
Topics:
Neugebauer, Wolfgang
Schreier, Peter
Acid-catalyzed degradation (simultaneous distillation-extraction; pH 2.5) of glycosidically bound 3-hydroxy-α-ionol from stinging nettle (Urtica dioica L.) yielded 2,2,6-trimethyl-7-methylenebicyclo<4.3.0>nona-4,8-diene and 2,2,6,7-tetramethylbicyclo<4.3.0>nona-4,7,9-triene as well as 1-(2-butenylidene)-2,6,6-trimethylcyclohexa-2.4-diene(1),1-(2-butenylidene)-6,6-dimethyl-2-methylenecyclohex-3-ene (2),and isomeric 4-(2,6,6-trimethylcyclohexa-2,4-dien-1-yl)but-3-en-2-ol(2,3-didehydro-α-ionol) (3a-d) and 4-(6,6-dimethyl-2-methylenecyclohex-3-en-1-yl)but-3-en-2-ol(3,4-didehydro-γ-ionol) (4a-d), which were identified by comparison of their chromatographic and spectral (MS; vapor phase FTIR) data with those of synthesized reference compounds.Configuration of the butenylidene chain of 1 and 2 was established by NOE experiments.The absolute configuration of the stereoisomers of 3 and 4 was elucidated using optically pure reference compounds.Enantiodifferentiation carried out by on-line coupled multidimensional gas chromatography-mass spectrometry revealed the occurrence of 1'R,2R and 1'R,2S diastereomers (3a/3c and 4a/4c) in stinging nettle. Keywords: 1-(2-Butenylidene)-2,6,6-trimethylcyclohexa-2,4-diene; 1-(2-butylidene)-6,6-dimethyl-2-methylenecyclohex-3-ene; 2,3-didehydro-α-ionol; 3,4-didehydro-γ-ionol; enantiodifferentiation; 3-hydroxy-α-ionol; stinging nettle
View MoreHuangshi Meifeng Chemical Co.,ltd.
Contact:+86-714-6516706
Address:1941-4-3#,Hubin Avenue,Huangshi,Hubei,China
Contact:+86-13666670345
Address:Agricultural Development Zone, Haining, Jiaxing, Zhejiang
Tangshan Wisdom Trading Co.,Ltd
Contact:86 315 2222979
Address:No.41 BeiXinXi Road, Yangguang building 1-1102 , Tangshan, Hebei, China
SHIFANG SUHONG CHEMICAL CO.,LTD
Contact:+86-838-2224563
Address:Room 1207 Zongchen Sunshine No.128 Taishan South Road,Deyang City,Sichuan China
Jinan Jianfeng Chemical Co., Ltd
Contact:0086-531-88110457
Address:sales01(-a-t-)pharmachemm{dot}c+o+m
Doi:10.1055/s-2000-7605
(2000)Doi:10.1039/b005552m
(2000)Doi:10.1007/s12009-001-0047-4
(1930)Doi:10.1021/jm00294a027
(1971)Doi:10.1016/S0957-4166(97)00256-5
(1997)Doi:10.1016/S0960-894X(03)00684-X
(2003)