On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol

Davin, Laurence B.; Bedgar, Diana L.; Katayama, Takuya; Lewis, Norman

doi:10.1016/s0031-9422(00)97544-7

Cited by 124 publications

(71 citation statements)

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“…A library containing 3.5 ϫ 10 5 recombinants was made, and its 1.4 ϫ 10 5 plaques were screened. The second cDNA library was constructed using a TimeSaver cDNA Synthesis kit (Pharmacia) with oligo(dT) [12][13][14][15][16][17][18] primer. Packaging by Lambda Inn packaging system (Nippon Gene, Japan) resulted in a library comprising of 2 ϫ 10 6 plaque-forming units, of which approximately 98% were recombinants.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, they purified a cytochrome P-450 enzyme that mediates specific intermolecular phenol oxidative coupling reaction to form bisbenzylisoquinoline alkaloid berbamunine (16). Presence of peroxidaselike stereoselective phenol coupling enzyme is reported for lignan biosynthesis (17). Therefore, it is very interesting to know how the same type of phenol oxidative coupling reactions are driven by the different kind of oxidation enzymes such as cytochrome P-450s, peroxidase-like enzymes in plants, and * This work was supported in part by grants-in-aid for scientific research from the Ministry of Education, Science, and Culture of Japan.…”

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confidence: 99%

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Molecular Cloning and Heterologous Expression of the Gene Encoding Dihydrogeodin Oxidase, a Multicopper Blue Enzyme from Aspergillus terreus

Huang

Fujii

Ebizuka

et al. 1995

Journal of Biological Chemistry

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Aspergillus terreus dihydrogeodin oxidase (DHGO) is an enzyme catalyzing the stereospecific phenol oxidative coupling reaction converting dihydrogeodin to (؉)-geodin. We previously reported the purification of DHGO from A. terreus and raised polyclonal antibody against DHGO. From the first cDNA library constructed in gt11 using mRNA from 3-day-old mycelium of A. terreus, four clones were identified using anti-DHGO antibody, but all contained partial cDNA inserts around 280 base pairs. This cDNA fragment was used as a probe to clone the genomic DNA and cDNA for dihydrogeodin oxidase from A. terreus.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Molecular Cloning and Heterologous Expression of the Gene Encoding Dihydrogeodin Oxidase, a Multicopper Blue Enzyme from Aspergillus terreus

Huang

Fujii

Ebizuka

et al. 1995

Journal of Biological Chemistry

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“…The substance (þ )-pinoresinol is a common compound of the lignan fraction of several plants, such as the seeds of the species Forsythia (Oleaceae family) (Davin et al 1992) and Sesamum indicum (sesame) (Kato et al 1998), while (þ )-1-acetoxypinoresinol, (þ )-1-hydroxypinoresinol and their glycosides have been found in the bark of the Olea europeae L. (olive) (Tsukamoto et al 1984(Tsukamoto et al , 1985. How lignans are transformed into the main component of the phenolic fraction of olive oil is not known.…”

Section: Chemical Structurementioning

confidence: 99%

The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health

et al. 2005

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The Mediterranean diet is rich in vegetables, cereals, fruit, fish, milk, wine and olive oil and has salutary biological functions. Epidemiological studies have shown a lower incidence of atherosclerosis, cardiovascular diseases and certain kinds of cancer in the Mediterranean area. Olive oil is the main source of fat, and the Mediterranean diet's healthy effects can in particular be attributed not only to the high relationship between unsaturated and saturated fatty acids in olive oil but also to the antioxidant property of its phenolic compounds. The main phenolic compounds, hydroxytyrosol and oleuropein, which give extra-virgin olive oil its bitter, pungent taste, have powerful antioxidant activity bothin vivoandin vitro. The present review focuses on recent works analysing the relationship between the structure of olive oil polyphenolic compounds and their antioxidant activity. These compounds' possible beneficial effects are due to their antioxidant activity, which is related to the development of atherosclerosis and cancer, and to anti-inflammatory and antimicrobial activity.

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“…For experimental convenience, attention was directed towards Forsythia species where the lignan biosynthetic pathway has now been established to follow the scheme shown in Figure 7 (103,109,(125)(126)(127)(128)(129)(130)(131)(132)(133)(134)(135). As can be seen, the entry point involves stereoselective coupling of two ^-coniferyl alcohol molecules to afford (+)-pinoresinol (109).…”

Section: Biosynthesis Of Lignansmentioning

confidence: 99%

Lignin and Lignan Biosynthesis: Distinctions and Reconciliations

Lewis

Davin

Sarkanen

1998

ACS Symposium Series

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Before 1996, the framework within which lignin biosynthesis was understood at the molecular level had not fundamentally changed for 4 decades. During the same period nothing at all had been explicitly proposed about the mechanistic basis for lignan formation in vivo. The associated deficit in plant biochemistry was not minor: lignins and lignans together account for roughly 30% of the organic carbon in vascular plants. On the other hand, the biochemical transformations in phenylpropanoid metabolism leading, via the shikimate-chorismate pathway through phenylalanine or tyrosine, to the so-called monolignols (namely, the monomeric lignin/lignan precursors) came to be reasonably well documented. Indeed, attention has more recently been drawn to the identification of de facto rate-limiting steps in the various metabolic segments of the pathway as potential control-points for biotechnological manipulation. The most curious characteristic usually attributed to the lignin/lignan biosynthetic pathway is that the monolignol-derived radical coupling processes leading to lignans are regio-and stereospecific, whereas those resulting in lignin macromolecules ostensibly are not. Now that the molecular basis for the dehydrogenative dimerization of monolignols to lignans has been unraveled, however, it appears likely that an analogous mechanism may be operative in the dehydrogenative polymerization of monolignols to lignins. The investigation of this possibility has indeed become a central concern in the field of lignin biosynthesis.It has been almost three decades (7) since a comprehensive attempt had been made to summarize and evaluate contending views about lignin biosynthesis. Accordingly, the present volume draws together the current, yet conceptually vastly differing, ideas about how lignin composition and structure are established in living plants. It differs from all prior contributions, not only in introducing fresh evidence to support a compelling new paradigm that seeks to understand how lignin structure is established in vivo, but also in including lignan biosynthesis for comparative purposes. Indeed it appears that the first committed step in lignan biosynthesis bears an important relationship to the manner in which the configurations of lignins are specified in vivo.

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On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol

Cited by 124 publications

References 13 publications

Molecular Cloning and Heterologous Expression of the Gene Encoding Dihydrogeodin Oxidase, a Multicopper Blue Enzyme from Aspergillus terreus

Molecular Cloning and Heterologous Expression of the Gene Encoding Dihydrogeodin Oxidase, a Multicopper Blue Enzyme from Aspergillus terreus

The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health

Lignin and Lignan Biosynthesis: Distinctions and Reconciliations

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