97134-11-7Relevant academic research and scientific papers
Molecular characterization of NbEH1 and NbEH2, two epoxide hydrolases from Nicotiana benthamiana
Huang, Fong-Chin,Schwab, Wilfried
, p. 6 - 15 (2013/07/11)
Plant epoxide hydrolases (EH) form two major clades, named EH1 and EH2. To gain a better understanding of the biochemical roles of the two classes, NbEH1.1 and NbEH2.1 were isolated from Nicotiana benthamiana and StEH from potato and heterologously expressed in Escherichia coli. The purified recombinant proteins were assayed with a variety of substrates. NbEH1.1 only accepted some aromatic epoxides, and displayed the highest enzyme activity towards phenyl glycidyl ether. In contrast, NbEH2.1 displayed a broad substrate range and similar substrate specificity as StEH. The latter enzymes showed activity towards all fatty acid epoxides examined. The activity (Vmax) of NbEH1.1 towards phenyl glycidyl ether was 10 times higher than that of NbEH2.1. On the contrary, NbEH2.1 converted cis-9,10-epoxystearic acid with Vmax of 3.83 μmol min mg-1 but NbEH1.1 could not hydrolyze cis-9,10- epoxystearic acid. Expression analysis revealed that NbEH1.1 is induced by infection with tobacco mosaic virus (TMV) and wounding, whereas NbEH2.1 is present at a relatively constant level, not influenced by treatment with TMV and wounding. NbEH1.1 transcripts were present predominantly in roots, whereas NbEH2.1 mRNAs were detected primarily in leaves and stems. Overall, these two types of tobacco EH enzymes are distinguished not only by their gene expression, but also by different substrate specificities. EH1 seems not to participate in cutin biosynthesis and it may play a role in generating signals for activation of certain defence and stress responses in tobacco. However, members of the EH2 group hydrate fatty acid epoxides and may be involved in cutin monomer production in plants.
Efficient and specific conversion of 9-lipoxygenase hydroperoxides in the beetroot. formation of pinellic acid
Hamberg, Mats,Olsson, Ulrika
experimental part, p. 873 - 878 (2012/02/01)
The linoleate 9-lipoxygenase product 9(S)-hydroperoxy-10(E),12(Z)- octadecadienoic acid was stirred with a crude enzyme preparation from the beetroot (Beta vulgaris ssp. vulgaris var. vulgaris) to afford a product consisting of 95% of 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid (pinellic acid). The linolenic acid-derived hydroperoxide 9(S)-hydroperoxy-10(E) ,12(Z),15(Z)-octadecatrienoic acid was converted in an analogous way into 9(S),12(S),13(S)-trihydroxy-10(E),15(Z)-octadecadienoic acid (fulgidic acid). On the other hand, the 13-lipoxygenase-generated hydroperoxides of linoleic or linolenic acids failed to produce significant amounts of trihydroxy acids. Short-time incubation of 9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid afforded the epoxy alcohol 12(R),13(S)-epoxy-9(S)-hydroxy-10(E)-octadecenoic acid as the main product indicating the sequence 9-hydroperoxide → epoxy alcohol → trihydroxy acid catalyzed by epoxy alcohol synthase and epoxide hydrolase activities, respectively. The high capacity of the enzyme system detected in beetroot combined with a simple isolation protocol made possible by the low amounts of endogenous lipids in the enzyme preparation offered an easy access to pinellic and fulgidic acids for use in biological and medical studies.
A chemoenzymatic asymmetric synthesis of (9S,12S,13S)- and (9S,12RS,13S)-pinellic acids
Sharma, Anubha,Mahato, Seema,Chattopadhyay, Subrata
scheme or table, p. 4986 - 4988 (2009/12/03)
A brief and facile synthesis of the title compounds has been developed by using an efficient lipase-catalyzed acylation and a chiral template-directed diastereoselective alkylation for incorporating the stereogenic centres. A cross-metathesis was employed to get the required E-olefin geometry.
Synthesis of (-)-pinellic acid and its (9R,12S,13S)-diastereoisomer
Sabitha, Gowravaram,Bhikshapathi, Martha,Reddy, Erigala Venkata,Yadav, Jhillu S.
experimental part, p. 2052 - 2057 (2010/01/11)
The total synthesis of (-)-pinellic acid with (9S,12S,13S)-configuration and its (9R,12S,13S)-diastereoisomer was achieved in high overall yields from a common intermediate derived from (+)-L-diethyl tartrate.
A concise synthesis of pinellic acid using a cross-metathesis approach
Miura, Ayako,Kuwahara, Shigefumi
experimental part, p. 3364 - 3368 (2009/09/06)
A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin interm
Enantioselective syntheses of (-)-pinellic acid, α- and β-dimorphecolic acid
Naidu, S. Vasudeva,Gupta, Priti,Kumar, Pradeep
, p. 7624 - 7633 (2008/02/07)
An efficient enantioselective convergent approach for the synthesis of (-)-pinellic acid 1, α- and β-dimorphecolic acid (2 and 3) from 1,9-nonane diol is described. The synthetic strategy features Sharpless asymmetric hydroxylation, Sonogashira coupling and Birch reduction.
Enantioselective synthesis of (-)-pinellic acid
Naidu, S. Vasudeva,Kumar, Pradeep
, p. 2279 - 2282 (2007/10/03)
An enantioselective convergent approach toward the total synthesis of pinellic acid 1 from 1,9-nonanediol is described. The synthetic strategy features iterative Sharpless asymmetric dihydroxylation, Sonogashira coupling and Birch reduction.
Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acids
Shirahata, Tatsuya,Sunazuka, Toshiaki,Yoshida, Kiminari,Yamamoto, Daisuke,Harigaya, Yoshihiro,Kuwajima, Isao,Nagai, Takayuki,Kiyohara, Hiroaki,Yamada, Haruki,Omura, Satoshi
, p. 9483 - 9496 (2007/10/03)
Pinellic acid from the tuber of Pinellia ternate, an active herbal component of the traditional Japanese herbal (Kampo) medicine Sho-seiryu-to, is a C18 trihydroxy fatty acid whose absolute stereochemistry has now been determined. All stereoisomers of pinellic acid were synthesized via regioselective asymmetric dihydroxylation, regioselective inversion, and stereoselective reduction in order to determine their absolute stereochemistries and adjuvant activities. Among this series of isomers, the (9S,12S,13S)-compound, which is a natural product, exhibited the most potent adjuvant activity. Spectral data for all of the stereoisomers of the 1,2-allylic diols were compared and related to their stereochemistries.
VACCINE PREPARATION CONTAINING FATTY ACID AS COMPONENT
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, (2008/06/13)
The present invention provides an adjuvant that is a hydroxy unsaturated fatty acid or a derivative thereof, as well as a vaccine preparation containing the adjuvant as a constituent. For example, a vaccine shows sufficient activity to enhance the immunity when a hydroxy unsaturated fatty acid having the following structure is administered:
Total synthesis of pinellic acid, a potent oral adjuvant for nasal influenza vaccine. Determination of the relative and absolute configuration
Sunazuka, Toshiaki,Shirahata, Tatsuya,Yoshida, Kiminari,Yamamoto, Daisuke,Harigaya, Yoshihiro,Nagai, Takayuki,Kiyohara, Hiroaki,Yamada, Haruki,Kuwajima, Isao,Omura, Satoshi
, p. 1265 - 1268 (2007/10/03)
Pinellic acid (1), isolated from a medicinal plant Pinelliae tuber, has potent adjuvant activity. The absolute configuration of pinellic acid was expected by derivatization of this compound and CD exciton chirality method. A convergent synthetic route to pinellic acid has been developed via regioselective asymmetric dihydroxylation and stereoselective reduction. The absolute configuration of pinellic acid was determined to be 9S,12S,13S, by comparing with the spectra data of natural and synthetic compounds.
