- SYNTHESIS OF STABLY DEUTERIATED ABSCISIC ACID, PHASEIC ACID AND RELATED COMPOUNDS
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Methyl esters of abscisic acid (ABA) analogues and metabolites dissolved in 0.1-1.0 M sodium methoxide in MeO(2)H replaced four of their sidechain (1)H atoms with (2)H (C-4 and C-6) over a period of 4 to 8 weeks.The esters were hydrolysed by adding (2)H20
- Willows, R. D.,Netting, A. G.,Milborrow, B. V.
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- 3'-SUBSTITUTED-ABSCISIC ACID DERIVATIVES
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The invention relates to a novel class of (S)-3′-substituted-abscisic acid derivatives and (±)-3′-substituted-abscisic acid derivatives, and methods of synthesizing the derivatives.
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Paragraph 0059-0060
(2016/02/03)
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- (S)-3′-methyl-abscisic acid and esters thereof
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The invention relates to (S)-3′-methyl-abscisic acid, and esters thereof, and methods of using and making these compounds.
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Page/Page column 6
(2016/05/24)
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- (S)-2′-vinyl-abscisic acid derivatives
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The invention relates to a novel class of (S)-2′-vinyl-substituted-abscisic acid derivatives, and to methods of synthesizing and using the derivatives.
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Page/Page column 6
(2016/10/17)
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- (S)-3'-METHYL-ABSCISIC ACID AND ESTERS THEREOF
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The invention relates to (S)-3′-methyl-abscisic acid, and esters thereof, and methods of using and making these compounds.
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Paragraph 0039; 0040
(2015/07/22)
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- Synthesis and biological activity of abscisic acid esters
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Abstract 16 ABA esters including 11 new compounds were prepared by two different esterification routes. All the structures of ABA esters were confirmed by 1H NMR, 13C NMR and HRMS. Their biological activity and hydrolysis stability were investigated. Fortunately, there were 15 and 9 compounds which displayed much better or nearly the same inhibition activity for rice seedling growth and Arabidopsis thaliana seed germination compared to ABA, respectively. Especially, compounds 2d and 2g showed better biological activities than ABA in the three tests. Moreover, we found that chemical hydrolysis ability of the esters in vitro had little relationship to their biological activity.
- Wan, Chuan,Zhang, Yuanzhi,Yang, Dongyan,Han, Xiaoqiang,Li, Xiuyun,Li, Hong,Xiao, Yumei,Qin, Zhaohai
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p. 267 - 272
(2015/06/22)
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- Electrolytic reduction of abscisic acid methyl ester and its free acid
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Abscisic acid (ABA, 1), a plant hormone, has electrophilicity derived almost entirely from the side-chain, 3-methylpenta-2,4-dienoic acid. The electrochemical property of ABA was investigated by analysis of its cathodic reaction. ABA methyl ester (1-Me) w
- Hirai, Nobuhiro,Iwami, Kumiko,Horiuchi, Mari,Kano, Kenji,Todoroki, Yasushi,Ohigashi, Hajime
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body text
p. 89 - 98
(2012/08/28)
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- Asymmetrical ligand binding by abscisic acid 8′-hydroxylase
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Abscisic acid (ABA), a plant stress hormone, has a chiral center (C1′) in its molecule, yielding the enantiomers (1′S)-(+)-ABA and (1′R)-(-)-ABA during chemical synthesis. ABA 8′-hydroxylase (CYP707A), which is the major and key P450 enzyme in ABA catabol
- Ueno, Kotomi,Yoneyama, Hidetaka,Mizutani, Masaharu,Hirai, Nobuhiro,Todoroki, Yasushi
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p. 6311 - 6322
(2008/09/17)
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- Synthesis and biological activity of 4'-methoxy derivatives of abscisic acid
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Replacing the 4'-carbonyl group of abscisic acid with a methoxy group does not affect the abscisic acid (ABA)-like activities of the product in barley aleurone protoplasts, although the reduction of ABA to 4'-hydroxyl derivatives significantly reduces the
- Asami, Tadao,Min, Yong Ki,Nakano, Takeshi,Matsuyama, Tomoki,Murofushi, Noboru,Yamaguchi, Isomaro,Yoshida, Shigeo
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p. 1571 - 1574
(2007/10/03)
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- Simple methods for the preparation of enantiomerically pure abscisic acid (ABA) analogues from (S)-(+)-ABA
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(1'S, 2Z, 4E)-3-Methyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2- cyclohexenyl)-2,4-pentadienoic acid (abscisic acid, ABA) is efficiently converted into the corresponding aldehyde, primary alcohol, and triol derivatives using readily available reagents (oxalyl
- Ward, Dale E.,Gai, Yuanzhu
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p. 2133 - 2142
(2007/10/03)
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- Chemical Constituents from the Root and Aerial Parts of Rosa taiwanensis
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The root and aerial parts of Rosa taiwanensis Nakai contain the chemical constituents phenols, unsaturated acids, liolide, abscisic acid, flavones, sterols, lupeol, betulin, betulinic acid, oleanolic acid and ursolic acid derivatives.Among them, 2α,3α-dihydroxyurs-12,19-dien-28-oic acid and its C-3 epimer are new compounds.Key Words Rosa taiwanensis; Rosaceae; Aerial part; Root; Flavones; Ursolic acid derivatives; Lupeol; Betulin; Oleanolic acid.
- Yang, Shen-Chyun,Fang, Jim-Min,Cheng, Yu-Shia
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p. 573 - 578
(2007/10/02)
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- Synthesis, Biological Activity and Metabolism of (S)-(+)-3'-Fluoroabscisic Acid
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(S)-(+)-3'-Fluoroabscisic acid (5a) was synthesized as an analogue of abscisic acid that can resist the metabolic cyclization of 8'-hydroxyabscisic acid to phaseic acid due to increased electron density at C-2'.The inhibitory activity of 5a was slightly h
- Todoroki, Yasushi,Hirai, Nobuhiro,Ohigashi, Hajime
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p. 6911 - 6926
(2007/10/02)
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- Facile Preparation of Chiral Abscisic Acid
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The asymmetric epoxidation of (+/-)-methyl (2Z,4E)-1',4'-dihydroxy-α-ionylideneacetates is described for the preparation of chiral abscisic acid.A conventional Sharpless kinetic resolution of (+/-)-1',4'-cis-dihydroxyacetate with diethyl L-tartrate and then two simple steps of conversion gave (S)-abscisic acid, which was also obtained by combination of (+/-)-1',4'-trans-dihydroxyacetate with diethyl D-tartrate.Finally, (S)-abscisic acid was obtained in a 25percent overall yield from the racemic mixture.
- Yamamoto, Hiroshi,Oritani, Takayuki
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p. 992 - 994
(2007/10/02)
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- Facile Aromatisation of Abscisic Acid
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Treatment of abscisic acid (ABA) or its methyl ester either with acetic anhydride and toluene-p-sulfonic acid or with lithium diisopropylamide and methyl chloroformate led to aromatisation of the cyclohexene ring.A mechanism for the reaction is proposed w
- Beale, Michael H.,Chen, Angi,Harrison, Polly A.,Willis, Christine L.
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p. 3061 - 3064
(2007/10/02)
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- Syntheses of Chiral 4'-Hydroxy and 1',4'-Dihydroxy-γ-ionylideneacetic Acids, Fungal Biosynthetic Intermediates of Abscisic Acid
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Both chiral 4'-hydroxy and 1',4'-dihydroxy-γ-ionylideneacetic acids (3, 4 and 5), biosynthetic intermediates of abscisic acid produced by Cercospora cruenta, were synthesized from a chiral starting material, (R)- or (S)-4-hydroxy-2,2-dimethyl-1-cyclohexanone (7). -Sigmatropic rearrangement of (S)-1-chloromethyl-3,3-dimethyl-5-tetrahydropyranyl(THP)oxy-1-cyclohexene (8), followed by the Reformatsky reaction with 4-bromo-3-methyl-2-butenoate (10) gave (1'R,4'S)-4.The diastereomeric isomer, (1'R,4'R)-3, was synthesized in the same manner.The reaction of (S)-2,2-dimethyl-5-methylene-4-THPoxy-1-cyclohexanone (14) with a Grignard reagent prepared from (Z)-3-methyl-2-penten-4-ynyl THP ether (15) and subsequent conversion of the side chain gave (1'S,4'S)-5.These synthetic compounds confirmed the stereochemistry of natural 3, 4 and 5.
- Yamamoto, Hiroshi,Oritani, Takayuki,Yamashita, Kyohei
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p. 1923 - 1929
(2007/10/02)
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- Syntheses of Enantiomerically Pure Violaxanthins and Related Compounds
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The epoxides 16 and ent-16, prepared by Sharpless-Katsuki oxidation of 15 in excellent yield and very high enantiomeric purity, were used as synthons for the preparation of (+)-(S)-didehydrovomifoliol (45), (+)-(6S,7E,9E)-abscisic ester 46, (+)-(6S,7E,9Z)-abscisic ester 47, (-)-(3S,7E,9E)-xanthoxin (49), (-)-(3R,7E,9E)-xanthoxin (50), (3S,5R,6S,3'S,5'R,6'S,all-E)-violaxanthin (1), (3R,5R,6S,3'R,5'R,6'S,all-E)-violaxanthin (55) and their (9Z) (see 53, 57), (13Z) (see 54, 58), and (15Z) (see 60) isomers.The novel violadione (61) was prepared from 1 by oxidation with DMSO/Ac2O.By base treatment, 61 was converted into violadienedione (62), a potential precursor of carotenoids with phenolic end groups.
- Acemoglu, Murat,Uebelhart, Peter,Rey, Max,Eugster, Conrad Hans
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p. 931 - 956
(2007/10/02)
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- IDENTIFICATION OF ABSCISIC ACID IN THE SEAWEED ASCOPHYLLUM NODOSUM
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Abscisic acid (ABA) has been isolated from commercial preparations and freeze-dried samples of the brown algae Ascophyllum nodosum.Purification by established methods yielded 0.03-0.15 μg ABA/g dry weight in lyophilized powders and 0.10-0.46 μg ABA/g dry wt in a commercial extract.These values are similar to those reported for higher plants.The presence of abscisic acid was confirmed by mass spectroscopy, providing an unambiguous identification of ABA in extracts of macroalgae.Key Word Index - Ascophyllum nodosum, Phaeophyta, seaweed, algae, abscisic acid, phytohormone, growth regulator.
- Boyer, Gregory L.,Dougherty, Susan S.
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p. 1521 - 1522
(2007/10/02)
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- ABSCISIC ACID FROM ALTERNARIA BRASSICAE
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Ket Word Index - Alternaria brassicae; black spot fungus; abscisic acid, identification.Abstract - Abscisic acid has been characterized in the mycelium of the black spot fungus, Alternaria brassicae.
- Dahiya, Jagroop S.,Tewari, Jalpa P.,Woods, Donald L.
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p. 2983 - 2984
(2007/10/02)
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- Isolation and Structure of 4'-Hydroxy-γ-ionylideneacetic Acids from Cercospora cruenta, a Fungus Producting (+)-Abscisic Acid
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From a culture broth of Cercospora cruenta were isolated some new metabolites structurally related to (+)-abscisic acid: (+)-(2Z,4E)-(1'R,4'S)-4'-hydroxy-γ-ionylideneacetic acid and (2E,4E)-1',4'-dihydroxy-γ-ionylideneacetic acid.The stereochemistry of th
- Oritani, Takayuki,Yamashita, Kyohei
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p. 275 - 278
(2007/10/02)
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- Germination Inhibition in Stigma Extracts of Tobacco and Identification of MeABA, ABA, and ABA-&β-D-Glucopyranoside
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Extracts of various flower tissues of tobaccowith 70percent methanol inhibited tobacco seed germination differently.Among them, extracts of stigma and anther were partitioned between ethyl acetate and water, the activity of the ethyl acetate layer was str
- Matsuzaki, Toshiake,Koiwai, Akira
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p. 2193 - 2200
(2007/10/02)
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- ISOLATION OF 4'-DIHYDROABSCISIC ACID FROM IMMATURE SEEDS OF VICIA FABA
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4'-Dihydroabscisic acid was isolated from immature seeds of Vicia faba.Its identity was proved by TLC and MS. - Key Word Index: Vicia faba; Leguminosae; seed; identification; sesquiterpene; 4'-dihydroabscisic acid.
- Dathe, Wilfried,Sembdner, Guenther
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p. 1798 - 1799
(2007/10/02)
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- ABSCISIC ACID LEVELS IN THE ROOT TIPS OF SEVEN ZEA MAYS VARIETIES
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Key Word Index - Zea mays; Graminae; endogenous abscisic acid; inhibitors; GC-MS; mass fragmentography; stable isotope dilution. Seven varieties of Zea mays were analyzed for cis-abscisic acid (ABA) and trans-ABA levels in the primary root tips by a stabl
- Rivier, L.,Pilet, P. E.
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- GC-MS IDENTIFICATION OF ABSCISIC ACID AND ABSCISIC ACID METABOLITES IN SEED OF VIGNA UNGUICULATA
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Abscisic acid, phaseic acid and 4'-dihydrophaseic acid were identified by GC-MS of derivatized (Me, MeTMSi) extracts from immature fruits of Vigna unguiculata.The fruits also contained some other ABA-related compounds, one of which might be epi-4'-dihidro
- Adesomoju, Akinbo A.,Okogun, Joseph I.,Ekong, Donald E. U.,Gaskin, Paul
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p. 223 - 226
(2007/10/02)
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