Enantiomeric compositions and biosynthesis ofWikstroemia sikokiana lignans

Okunishi, Tomoya; Umezawa, Toshiaki; Shimada, Morimi

doi:10.1007/bf00776455

Cited by 29 publications

(27 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Reverse-phase high performance liquid chromatography (HPLC) of lariciresinol and pinoresinol and chiral HPLC analyses of pinoresinol were done as previously described (9). Chiral liquid chromatography-mass spectrometry (LC-MS) of lariciresinol was done as follows.…”

Section: Instruments and Chromatography-mentioning

confidence: 99%

Characterization of Arabidopsis thaliana Pinoresinol Reductase, a New Type of Enzyme Involved in Lignan Biosynthesis

Nakatsubo

Mizutani

Suzuki

et al. 2008

Journal of Biological Chemistry

Self Cite

103

View full text Add to dashboard Cite

A lignan, lariciresinol, was isolated from Arabidopsis thaliana, the most widely used model plant in plant bioscience sectors, for the first time. In the A. thaliana genome database, there are two genes (At1g32100 and At4g13660) that are annotated as pinoresinol/lariciresinol reductase (PLR). The recombinant AtPLRs showed strict substrate preference toward pinoresinol but only weak or no activity toward lariciresinol, which is in sharp contrast to conventional PLRs of other plants that can reduce both pinoresinol and lariciresinol efficiently to lariciresinol and secoisolariciresinol, respectively. Therefore, we renamed AtPLRs as A. thaliana pinoresinol reductases (AtPrRs).

show abstract

Section: Instruments and Chromatography-mentioning

confidence: 99%

Characterization of Arabidopsis thaliana Pinoresinol Reductase, a New Type of Enzyme Involved in Lignan Biosynthesis

Nakatsubo

Mizutani

Suzuki

et al. 2008

Journal of Biological Chemistry

Self Cite

103

View full text Add to dashboard Cite

show abstract

“…26) Chemical syntheses and chemicals. Syntheses of the following compounds were as reported previously: [9, H2, OC 2 H3]coniferyl alcohol [1-d5]*, 11) [9, H2]coniferyl alcohol [1-d2], 16) (±)-2, 11) (±)- [9,9,9?,9?-2 H4]pinoresinols [(±)-2-d4], 16) (±)-lariciresinols [(±)-3], 28) (±)- [9,9,9?,9?-2 H 4 ] lariciresinols [(±)-3-d4], 16) (±)-secoisolariciresinols [(±)-4], 11) (±)- [9,9,9?,9?-2 H4]secoisolariciresinols [(±)-4-d4], 16) (±)-[arom-2 H]secoisolariciresinols [(±)-4-ARd ], 16) (±)-matairesinols [(±)-5], 26) and (±)-arctigenins [(±)-6]. 26) All solvents and reagents used were of reagent grade unless otherwise stated.…”

Section: Methodsmentioning

confidence: 99%

“…GC-MS was conducted as previously described. 11,16) Reversed-phase HPLC separation 11) and chiral HPLC separation of 2, 11) 3, 16) 4, 16) 5, 7) and 6 26) were conducted as previously described. Silica gel TLC and silica gel column chromatography employed Kieselgel 60 F254 (Merck) and Kieselgel 60 (Merck), respectively.…”

Section: Methodsmentioning

confidence: 99%

“…[2][3][4][5][14][15][16][17] In addition, phytochemical studies of such lignans as 2, 3 and 4, which are the furthest upstream on the biosynthetic pathway, have revealed that not only the sign of the optical rotation, i.e. predominant enantiomers of the lignans, but also the enantiomeric composition, z enantiomeric excess (e.e.)…”

Section: Please Scroll Down For Articlementioning

confidence: 99%

See 1 more Smart Citation

Stereochemical Diversity in Lignan Biosynthesis ofArctium lappaL.

Suzuki

Umezawa

Shimada

2002

Bioscience, Biotechnology, and Biochemistry

Self Cite

View full text Add to dashboard Cite

The stereochemistry of lignan biosynthesis in Arctium lappa L. is regulated organ-specifically. (+)-Secoisolariciresinol [81% enantiomeric excess (e.e.)] was isolated from A. lappa petioles. In sharp contrast, lignans whose predominant enantiomers have the opposite absolute configuration to that of (+)-secoisolariciresinol [i.e., (-)-matairesinol (>99% e.e.), (-)-arctigenin (>99% e.e.), and (-)-secoisolariciresinol (65% e.e.)] were isolated from seeds of the species. The stereochemical diversity of secoisolariciresinol was demonstrated with enzyme preparations from A. lappa petioles and seeds. Thus, a petiole enzyme preparation catalyzed the formation of (+)-pinoresinol (33% e.e.), (+)-lariciresinol (30% e.e.), and (+)-secoisolariciresinol (20% e.e.) from achiral coniferyl alcohol in the presence of NADPH and H202, whereas that from ripening seeds catalyzed the formation of (-)-pinoresinol (22% e.e.), (-)-lariciresinol (>99% e.e.), and (-)-secoisolariciresinol (38% e.e.) under the same conditions. In addition, the ripening seed enzyme preparation mediated the selective formation of the optically pure (>99% e.e.) (-)-enantiomer of matairesinol from racemic (+/-)-secoisolariciresinols in the presence of NADP. These results indicate that the stereochemical mechanism for lignan biosynthesis in A. lappa varies with organs, suggesting that multiple lignan-synthesizing isozymes are involved in the stereochemical control of lignan formation in A. lappa.

show abstract

“…The dry CHCl 3 extract of powdered roots of W. indica was separated by MPLC, followed by purification by preparative TLC, to give one new (1) and two known guaian-type sesquiterpenes, oleodaphnal (2) [7] and 1,7,10H-guaia-4,11-dien-3-one (3) [8], together with twelve known compounds: (+)-arctigenin [9], (+)matairesinol [9], (+)-trachelogenin [10], (+)-nortrachelogenin [11], (+)-hinokinin [8], (+)-kusunokinin [9], 7-methoxycoumarin [12], 7-hydroxycoumarin (umbelliferone) [13,14], daphnogitin [14,15], daphnoretin [14,16], salicifoliol [17], and (−)-pinoresinol [18,19].…”

mentioning

confidence: 99%

New Guaian-type Sesquiterpene from Wikstroemia indica

Kato

Dibwe

et al. 2014

Natural Product Communications

View full text Add to dashboard Cite

From a MeOH extract of powdered roots of Wikstroemia indica, we isolated a new guaian-type sesquiterpene (1) and two known guaian-type sesquiterpenes [oleodaphnal (2), 1,7,10H-guaia-4,11-dien-3-one (3)], together with twelve known compounds: (+)-arctigenin, (+)-matairesinol, (+)-trachelogenin, (+)-nortrachelogenin, (+)-hinokinin, (+)-kusunokinin, 7-methoxycoumarin, 7-hydroxycoumarin (umbelliferone), daphnogitin, daphnoretin, salicifoliol, and (−)-pinoresinol. The structure of compound 1 was determined to be 4,10,11-guaiatrien-3-one-14-oic acid, by the analyses of spectral data.

show abstract

Enantiomeric compositions and biosynthesis ofWikstroemia sikokiana lignans

Cited by 29 publications

References 18 publications

Characterization of Arabidopsis thaliana Pinoresinol Reductase, a New Type of Enzyme Involved in Lignan Biosynthesis

Characterization of Arabidopsis thaliana Pinoresinol Reductase, a New Type of Enzyme Involved in Lignan Biosynthesis

Stereochemical Diversity in Lignan Biosynthesis ofArctium lappaL.

New Guaian-type Sesquiterpene from Wikstroemia indica

Contact Info

Product

Resources

About