Isolation of 19 α‐H‐Lupeol from Maclura pomifera

Gearien, James E.; Klein, Michael D.

doi:10.1002/jps.2600640121

Cited by 10 publications

(10 citation statements)

References 8 publications

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“…In contrast, UGT75L4 was less regio-selective on flavone/flavonol substrates, which contain a C2-C3 double bond in the C-ring. Three glucosylated products were detected for apigenin (5,7,4 0 -trihydroxyflavone) and kaempferol (3,5,7,4 0 -trihydroxyflavone), suggesting that the 5-, 7-, and 4 0 -hydroxyl groups could all be glucosylated. However, when the 3 0 -position of the B ring was substituted by either hydroxylation or methoxylation, as in luteolin (5,7,3 0 ,4 0 -tetrahydroxyflavone), chrysoeriol (5,7,4 0 -trihydroxy 3 0 -methoxyflavone) or quercetin (3,5,7,3 0 ,4 0 -pentahydroxyflavone), only two glucosylated products were observed ( Supplementary Fig.…”

Section: Ugt75l4 Has Broad Substrate Recognition For Flavonoidsmentioning

confidence: 99%

“…2) were tested with the recombinant protein. The number of potential O-glucosylation sites for the isoflavone substrates tested were one for formononetin (7-hydroxy 4 0 -methoxyisoflavone), two for daidzein (7,4 0 -dihydroxyisoflavone) and biochanin A (5,7-dihydroxy 4 0 -methoxyisoflavone), and three for genistein (5,7,4 0 -trihydroxyisoflavone). HPLC analysis showed that only a single product was formed with each substrate (Fig.…”

Section: Ugt75l4 Has Broad Substrate Recognition For Flavonoidsmentioning

confidence: 99%

“…7-O-glucosylation was confirmed for genistein and formononetin, for which authentic 7-O-glucoside standards were available. Liquiritigenin (7,4 0 -dihydroxyflavanone), naringenin (5,7,4 0 -trihydroxyflavanone) and dihydroquercetin (3,5,7,3 0 4 0 -pentahydroxyflavanone) each gave a single glucosylated product, irrespective of the available hydroxyl groups, suggesting that UGT75L4 acted at either the 7-or 4 0 -hydroxyl groups of these flavanones/dihydroflavonols (Supplementary Fig. 3).…”

Section: Ugt75l4 Has Broad Substrate Recognition For Flavonoidsmentioning

confidence: 99%

“…Osage orange fruit accumulates a group of flavonoid, isoflavonoid and triterpene compounds [3][4][5][6][7]. Two predominant isoflavones, pomiferin and osajin, are derived from the simple isoflavone genistein by prenyl substitutions ( [7]; Fig.…”

Section: Introductionmentioning

confidence: 99%

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Phenylpropanoid glycosyltransferases from osage orange (Maclura pomifera) fruit

2006

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Flavonoids and isoflavonoids are well known for their beneficial effects on human health and their anti-insect and antimicrobial activities in plants. Osage orange fruit is rich in prenylated isoflavones and dihydrokaempferol and its glucoside. Four glycosyltransferases were identified from a collection of osage orange fruit expressed sequence tags. Biochemical characterization suggested that the glycosyltransferase UGT75L4 might be responsible for glucosylation of dihydrokaempferol in vivo, although this enzyme exhibited broad substrate recognition toward isoflavonoids and flavonoids in vitro. UGT88A4 was active on coumarin substrates. Identification of highly active phenylpropanoid glycosyltransferases will facilitate the metabolic engineering of glycosylated natural products in plants.

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Section: Ugt75l4 Has Broad Substrate Recognition For Flavonoidsmentioning

confidence: 99%

Section: Ugt75l4 Has Broad Substrate Recognition For Flavonoidsmentioning

confidence: 99%

Section: Ugt75l4 Has Broad Substrate Recognition For Flavonoidsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Phenylpropanoid glycosyltransferases from osage orange (Maclura pomifera) fruit

2006

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“…Lupeol acetate was recrystallized by ethanol. Its melting point was 217 ° C. The structure was established by H-NMR, 13 C-NMR and mass data ( fi g. 1 ) [8,9] .…”

Section: Isolation Of Lupeol Acetatementioning

confidence: 99%

Induction of Antifertility with Lupeol Acetate in Male Albino Rats

Gupta¹,

Bhatnager

Joshi³

et al. 2005

Pharmacology

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The present study was undertaken to evaluate the antifertility activity of the active principle, i.e. lupeol acetate, isolated from benzene extract of Alstonia scholaris in male albino rats. The treatment with lupeol acetateat the dose level of 10 mg/rat/day did not cause any significant change in the body weights, but significant reduction in the weight of reproductive organs, i.e. testes, epididymides, seminal vesicle and ventral prostate, was observed. Testicular sperm count, epididymal sperm count and motility were found significantly declined when compared with controls, which resulted in reduction of male fertility by 100%. Arrest of spermatogenesis was noted at various stages with production of primary spermatocytes (preleptotene and pachytene), secondary spermatocytes and step-19 spermatids were decreased by 52.36, 54.91, 55.67 and 69.65%, respectively. The seminiferous tubules appeared reduced in size by 24.62%. Cross-sectional surface area of Sertoli cells as well as their counts were found to be significantly depleted. Leydig cell nuclear area and number of mature Leydig cells were decreased by 27.65 and 35.47%. Biochemical parameters of tissues i.e. protein, sialic acid, glycogen and cholesterol content of testes and seminal vesicular fructose also showed significant reduction.

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Osage orange (Maclura pomifera): History and economic uses

Smith

Perino

1981

Econ Bot

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Isolation of 19 α‐H‐Lupeol from Maclura pomifera

Cited by 10 publications

References 8 publications

Phenylpropanoid glycosyltransferases from osage orange (Maclura pomifera) fruit

Phenylpropanoid glycosyltransferases from osage orange (Maclura pomifera) fruit

Induction of Antifertility with Lupeol Acetate in Male Albino Rats

Osage orange (Maclura pomifera): History and economic uses

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