Variations of nootkatone and valencene levels during the development of grapefruit

Rı́o, José Antonio del; Ortuño, A.; Garcia-Puig, D.; Porras, I.; Garcı́a-Lidón, A.; Sabater, F.

doi:10.1021/jf00021a003

Cited by 24 publications

(21 citation statements)

References 9 publications

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“…In the chromatographic conditions used, the retention time (Rt) corresponding to this sesquiterpene was 41.70 min, and its mass spectrum was similar to that obtained in other works (Del Rio et al, 1992a;Del Rio and Ortuiio, 1994).…”

Section: Resultssupporting

confidence: 78%

“…For capillary gas-liquid chromatography-mass spectrometry (GLC-MS) a Hewlett-Packard 5993 mass spectrometer was used with a column similar to that used above. The injector and transfer line temperature was 255 "C, ionization energy 70 eV, and scan time 1 s. Peak identification was confirmed by comparing the retention time and mass spectrum with those of authentic sample, as described previously (Del Rio et al, 1992a). Quantitative determinations were based on the known amount of added standard.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Flavanone and Nootkatone Levels in Different Varieties of Grapefruit and Pummelo

Ortuño¹,

Garcia-Puig²,

Fuster³

et al. 1995

J. Agric. Food Chem.

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The effects of variety, rootstock, and geographical location were studied as to their effects on secondary metabolite production in grapefruit and pummelo. The concentration of the flavanones narirutin, naringin, and neohesperidin and of the sesquiterpene nootkatone, which is principally responsible for the grapefruit's aroma, varies during h i t development. The highest flavanone levels are detected during the juvenile stages of fruit development, while nootkatone expression is associated with the processes of maturation and senescence. The possibility of increasing the levels of these metabolites by regulating the associated processes of growth and cell differentiation is discussed.

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Section: Resultssupporting

confidence: 78%

Section: Introductionmentioning

confidence: 99%

Flavanone and Nootkatone Levels in Different Varieties of Grapefruit and Pummelo

Ortuño¹,

Garcia-Puig²,

Fuster³

et al. 1995

J. Agric. Food Chem.

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“…The biosynthetic route to (+)-nootkatone in grapefruit has not been established experimentally, but has been suggested to start from valencene on which a regioselective allylic hydroxylation results in formation of 2-hydroxyvalencene (or nootkatol), followed by oxidation to (+)-nootkatone [4,5].…”

Section: Introductionmentioning

confidence: 99%

A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene

et al. 2010

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a b s t r a c tChicory (Cichorium intybus L.), which is known to have a variety of terpene-hydroxylating activities, was screened for a P450 mono-oxygenase to convert (+)-valencene to (+)-nootkatone. A novel P450 cDNA was identified in a chicory root EST library. Co-expression of the enzyme with a valencene synthase in yeast, led to formation of trans-nootkatol, cis-nootkatol and (+)-nootkatone. The novel enzyme was also found to catalyse a three step conversion of germacrene A to germacra-1(10),4,11(13)-trien-12-oic acid, indicating its involvement in chicory sesquiterpene lactone biosynthesis. Likewise, amorpha-4,11-diene was converted to artemisinic acid. Surprisingly, the chicory P450 has a different regio-specificity on (+)-valencene compared to germacrene A and amorpha-4,11-diene.

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“…Previous studies 21,25,26 report that these compounds are formed in the flavedo in increasing levels as the fruit matures. Coggins et al 25 examined the changes in essential oil constituents from the peel of Navel oranges, with and without gibberellin treatment.…”

Section: Ultimate Value Of Valencenementioning

confidence: 93%

“…They found that valencene concentrations in the untreated fruit generally increased with increasing maturity, which maximized at 350% higher concentrations than when the fruit was first examined. del Rio et al 26 observed the development of valencene and nootkatone in grapefruit as the fruit was allowed to mature. They observed that after 9 weeks valencene levels began to increase and reached a maximum level of approximately 1 mg/100 g fresh weight wax column, only those compounds with similar wax LRI values are considered.…”

Section: Ultimate Value Of Valencenementioning

confidence: 99%

Determination of the role of valencene in orange oil as a direct contributor to aroma quality

2005

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Valencene is the major sesquiterpene in orange peel oil and its concentration has been traditionally used to determine the oil's commercial value. Multidimensional GC-O/GC-MS was employed to determine the contribution of valencene to the aroma quality of a commercial orange oil. Thirty-seven aroma-active components were found in this orange oil. One of these components possessed a citrusy/woody aroma similar to that of valencene and eluted in the expected time region for valencene on a polar column. The volatiles in the valencene region were isolated by the heartcutting technique, directed to a second GC capillary column (DB-5) and split between a mass spectrometer and an olfactory port. Aroma activity was detected only from a peak identified as dodecanal, and not valencene. The identities of both compounds were confirmed from full scan mass spectra and reconfirmed with standards. Valencene concentrations in the original orange oil and three additional commercial orange oils were determined to be 54-68 µ µ µ µ µg/g, using GC-FID with an internal standard. The results indicated that valencene produced no aroma activity at the levels found in orange oil. Its use as a causative indicator of good quality orange oil must be questioned. Valencene may simply be an easy to measure marker for increased fruit maturity, which is known to correlate positively with increased orange flavour quality. This study also demonstrates the need for careful chromatography involving multiple columns whenever assigning aroma activity to a particular compound in GC-O studies.

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Variations of nootkatone and valencene levels during the development of grapefruit

Cited by 24 publications

References 9 publications

Flavanone and Nootkatone Levels in Different Varieties of Grapefruit and Pummelo

Flavanone and Nootkatone Levels in Different Varieties of Grapefruit and Pummelo

A chicory cytochrome P450 mono-oxygenase CYP71AV8 for the oxidation of (+)-valencene

Determination of the role of valencene in orange oil as a direct contributor to aroma quality

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