Phytochemistry p. 905 - 918 (1993)
Update date:2022-09-26
Topics:
Lamb, Nancy
Shaw, Angela C.
Abrams, Suzanne R.
Reaney, Martin J.
Ewan, Bruce
et al.
The metabolism of a biologically active abscisic acid (ABA) analogue, (+)-1'S,2'S)-2',3'-dihydroabscisic acid <(+)-4-(1E,3Z)-(4S,5S)-4-(4-carboxy-3-methyl-1,3-butadienyl)-4-hydroxy-3,3,5-trimethylcyclohexanone>, which cannot form phaseic acid was studied in a cell suspension culture of bromegrass (Bromus inermis).The analogue induced freezing tolerance in bromegrass cells similar to (S)-(+)-ABA and was oxidized to (1'S,2'S)-8'-hydroxy-2',3'-dihydroabscisic acid <4-(1E,3Z)-(3R,4S,5S)-4-(4-carboxy-3-methyl-1,3-butadienyl)-4-hydroxy-3-hydroxymethyl-3,5-dimethylcyclohexanone>.The enantiomer (-)-(1'R,2'R)-2',3'-dihydroabscisic acid, which was inactive in inducing freezing tolerance, was converted to two metabolites, viz., the corresponding enantiomeric (1'R,2'R)-8'-hydroxy-2',3'-dihydroabscisic acid <4-(1E,3Z)-(3S,4R,5R)-4-(4-carboxy-3-methyl-1,3-butadienyl)-4-hydroxy-3-hydroxymethyl-3,5-dimethylcyclohexanone> and reduction product (-)-(1E,3Z)-(1R,4S,6R)-1-(4carboxy-3-methyl-1,3-butadienyl)-2,2,6-trimethylcyclohexan-1,4-diol.Both enantiomers of the analogue were transformed to the glucose esters.The structures of the metabolites were established by both spectrometric analyses and chemical synthesis.The metabolite 8'-hydroxy-2',3'-hydroxyabscosic acid is a cyclohexanone analogue of 8'-hydroxyabscisic acid, the transient oxidation product in the metabolism of ABA to phaseic acid.Like phaseic acid, the racemic form of 8'-hydroxy-2',3'-dihydroabscisic acid was inactive in inducing freezing tolerance in bromegrass cells, suggesting that ABA and (+)-(1'S,2'S)-2',3'-dihydroabscisic acid were the active compounds.
View MoreShenyang Xinyihan Chemical Technology Co., Ltd.
Contact:+86-18525026267
Address:362, aigongbeijei street 23 , tiexi district,Shenyang, Liaoning, China
Shanghai Korey Pharm Co.,Ltd.(expird)
Contact:021-61840961 021-61840962
Address:No.157,Zhuguang Rd, Qingpu, Shanghai, China
KangZhiYuan Pharmaceutical Company Limited
Contact:(Sabrina)86-20-85273232
Address:4th floor, building B, Dadi industry zone, Tangxia, Tianhe, Guangzhou, China
Hangzhou Ocean Chemical Co., Ltd.
website:http://www.hzoceanchem.com
Contact:+86-571-88025872, 28272092, 28272096
Address:Room 623 ,Building No 1 , COFCO Radius Commercial Center Xiwen Road, Xiacheng District, Hangzhou, Zhejiang Province, China
Zhengzhou Xinlian Chemical Tech Co. ,Ltd
Contact:0371-65771781 021-52042910
Address:H Part, Building I, No. 700 Gonglu Road, Pudong New Area, Shanghai
Doi:10.1016/j.tetlet.2015.09.076
(2015)Doi:10.1021/ol403351x
(2014)Doi:10.1021/jo402485h
(2014)Doi:10.1002/(SICI)1099-1344(199712)39:12<1019::AID-JLCR43>3.0.CO;2-T
(1997)Doi:10.1021/jm00031a014
(1994)Doi:10.1016/j.tetlet.2021.153091
(2021)