Glucosylation of exogenous flavanones by grapefruit (Citrus paradisi) cell cultures

Lewinsohn, Efraim; Berman, Elisha; Mazur, Yehuda; Gressel, Jonathan

doi:10.1016/s0031-9422(00)84502-1

Cited by 70 publications

(35 citation statements)

References 20 publications

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“…3, lanes 1 In conclusion, we have demonstrated the enzymatic formation ofthe aglycone naringenin from p-coumaryl-CoA and malonyl-CoA in cell-free extracts derived from young Citrus tissues (Table I), indicating that chalcones are biosynthesized before their glucosylation at the developmental times expected. We have also shown that the glucosylation of naringenin and hesperetin at position 7 occurs in Citrus cell cultures (21,22), and is catalyzed by cell-free extracts of Citrus (Table II and Fig. 2).…”

Section: Chalcone Synthasementioning

confidence: 70%

“…Our earlier studies showed that the glycosylation of the aglycone in undifferentiated Citrus cells is not by the addition of a disaccharide; there was an initial glucosylation (21,22) and in one case a further rhamnosylation (22) of exogenous presented aglycones. Prunin (naringenin-7-O-glucoside) was shown to be a likely intermediate in the biosynthesis of naringin in immature grapefruit fruits (2).…”

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confidence: 95%

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Flavanone Glycoside Biosynthesis in Citrus

Lewinsohn

Britsch²,

Mazur³

et al. 1989

Plant Physiol.

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Previous indirect evidence suggested that the biosynthesis of flavonoids in Citrus may not proceed via the usual chalcone synthase reaction and that glycosylation occurs during chalcone formation and not afterward, as has been reported in other species. We detected chalcone-synthase and UDP-glucose:flavanone-7-O-glucosyl-transferase activities in cell-free extracts of Citrus. The glucosylated flavanone was further rhamnosylated when exogenous UDP-glucose and NADPH were added to the extract. Chalcone-synthase activity was detected in cellfree extracts derived from young leaves and fruits. Young fruits (2 millimeter diameter) had the highest chalcone synthase activity. UDP-glucose:flavanone-7-0-glucosyl-transferase activity was measured in cell-free extracts derived from young leaves and fruits of Citrus mitis and Citrus maxima. The highest UDP-glucose:flavanone-7-O-glucosyl-transferase activity was found in young C. maxima leaves. These data indicate that Citrus contains a flavonoid pathway similar to that studied in other species.Several Citrus spp. (Rutaceae) contain bitter tasting flavanone-disaccharides (18). They are used as food additives for their flavor or can be converted by hydrogenation into the extremely sweet dihydrochalcone derivatives (18). Little information is available on the biosynthetic pathways to flavanone-glycosides in Citrus (16). Chalcone-synthase is a key enzyme in the flavonoid pathway in several plants (13), but has not previously been reported in Citrus tissues. Chalconesynthase catalyzes the condensation of p-coumaryl-CoA with three molecules of malonyl-CoA yielding naringenin-chalcone (20). The substrate specificity of a 'naringin-chalconecyclase' activity, from immature grapefruit fruit (25), suggested that the flavonoid pathways in Citrus, might be different from the more studied flavonoid pathways of other plants (13,14) (Fig. 1). They interpreted their results (25) as suggesting that glucosylation and rhamnosylation occurred during chalcone formation in Citrus, as the aglycones were not ' Supported by a Minerva foundation travel grant. Present address:

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Section: Chalcone Synthasementioning

confidence: 70%

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confidence: 95%

Flavanone Glycoside Biosynthesis in Citrus

Lewinsohn

Britsch²,

Mazur³

et al. 1989

Plant Physiol.

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“…One might expect that flavonoids would be found in exponential phase tissue cultures, because they are continuously juvenile. Flavonoids were not detected in undifferentiated grapefruit calli nor in cell suspensions; however, these same cultures catalyzed the glucosylation of exogenous naringenin to prunin (Lewinsohn et al, 1986). We could not detect I-2-rhamnosyltransferase in undifferentiated grapefruit calli with the antibody (data not shown).…”

Section: Discussionmentioning

confidence: 86%

Juvenile-Specific Localization and Accumulation of a Rhamnosyltransferase and Its Bitter Flavonoid in Foliage, Flowers, and Young Citrus Fruits

1993

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“…Further separation and purification on column chromatograpy and HPLC yielded a new diterpenoid, 16-hydroxy communic acid (1), along with 31 known compounds including five norditerpenes (2-6), four biflavonoids (7)(8)(9)(10), nine monoflavonoids (11)(12)(13)(14)(15)(16)(17)(18)(19), nine flavanoid glycosides (20)(21)(22)(23)(24)(25)(26)(27)(28), and four aromatic derivatives (29)(30)(31)(32). Structural elucidation of 1 was based on spectroscopic analysis, mainly using HR-ESI-MS, IR, 1 H-, 13 C-, and 2D-NMR experiments.…”

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confidence: 99%

“…56, No. 4 (11), [20][21][22] kaempferol (12), [20][21][22] quercetin (13), [20][21][22] luteolin (14), 23) acacetin (15), [20][21][22] 5-hydroxy-7-methoxy-2-(4-methoxy-phenyl)-chromen-4-one (16), 24) catechin (17), 25) 6Ј-hydroxy-catchin (18), 25) and naringenin (19) 26) ; the nine flavanoid glycosides naringin (20), 27) orientin (21), [28][29][30] luteolin-7-glucoside (22), [28][29][30] rutin (23), [28][29][30] kaempferol-3-glucoside (24), [28][29][30] quercetin-3-glucoside (25), [28][29][30] quercetin-7-glucoside (26), [28][29][30] and (27) 28-30) and kaempferol-7-glucoside (28), [28][29]…”

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confidence: 99%