C-2 stereochemistry of naringin and its relation to taste and biosynthesis in maturing grapefruit

Gaffield, William; Lundin, Robert E.; Gentili, Bruno; Horowitz, Robert M.

doi:10.1016/0045-2068(75)90036-x

Cited by 49 publications

(37 citation statements)

References 16 publications

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“…Our observations, made on many samples of grapefruit taken during the entire season confirm the study of Horowitz et al 3 and add new details to the variation of C-2 chirality on naringin and relative amount of it and narirutin as a function of grapefruit maturity. Table 3 reports the changes in (2R) and (2S)-naringin and (2R/2S)-narirutin in albedo throughout the maturation of grapefruits collected in various habitat areas.…”

Section: Phytochemical Resultssupporting

confidence: 70%

“…The curve is somewhat different from that obtained by Horowitz et al 3 using unfractionated samples of albedo, particularly in small-size fruits. It was obtained by determining the C-2 diastereomeric composition by CD and 1 H NMR at 100 Mhz, without the separation of naringin from other flavanone glycosides still present in the albedo.…”

Section: Phytochemical Resultscontrasting

confidence: 46%

“…It has been reported that immature grapefruit contains only (2S)-naringin, whereas both diastereomers are present in the mature fruit. 3 The results of this study were obtained, however, by circular dichroism (CD) and 1 H NMR spectroscopy without separation of (2R)-and (2S)-naringin.…”

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confidence: 99%

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Chiral HPLC separation and CD spectra of the C‐2 diastereomers of naringin in grapefruit during maturation

2003

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Naringin is the chief flavanone glycoside of grapefruit (Citrus paradisi). It is responsible for part of the bitter taste of the fruit and can cause the inhibition of some cytochrome P450s. The direct separation of (2R)-and (2S)-naringin in the albedo of grapefruits was obtained in normal phase HPLC mode using Chiralcel OD as chiral stationary phase and n-hexane/ethanol with 0.1% of TFA as mobile phase. Chiralpak AD was almost ineffective in the separation. This procedure was used to evaluate the stereochemistry at C-2 during maturation of the grapefruit. The CD curves of (2R)-and (2S)-naringin isolated by semipreparative chiral HPLC were determined and the elution order of the chromatographic peaks was related to the absolute C-2 configuration. Partial resolution of the C-2 diastereomers of narirutin was obtained on Chiralpak AD. Chirality 15:661 -667,

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Section: Phytochemical Resultssupporting

confidence: 70%

Section: Phytochemical Resultscontrasting

confidence: 46%

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Chiral HPLC separation and CD spectra of the C‐2 diastereomers of naringin in grapefruit during maturation

2003

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“…In immature fruits (ca. 3 cm Ø) NAR appears only in its 2S-form, whereas mature fruits contain both 2S-and 2R-diastereomers [22,23]. PRU was found only in immature grapefruits and in its 2S-configuration, exclusively [22,24].…”

Section: Ce and Hplc Analysis Of Fgs In Mature And Immature Grapefruitsmentioning

confidence: 97%

Chiral separation of diastereomeric flavanone‐7‐O‐glycosides in citrus by capillary electrophoresis

Gel-Moreto¹,

Streich²,

Galensa³

2003

Electrophoresis

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The 2S- and 2R-diastereomers of major flavanone-7-O-glycosides found in sweet orange (Citrus sinensis), mandarine (Citrus deliciosa), grapefruit (Citrus paradisi), lemon (Citrus limon), and sour or bitter orange juice (Citrus aurantium) were separated for the first time by chiral capillary electrophoresis (CE) employing various buffers with combined chiral selectors. Native cyclodextrins (CDs), neutral and charged CD derivatives were examined as chiral additives to the background electrolyte (BGE). Separation efficiency has not proved satisfactory with one single CD as chiral selector in the buffer, a full and simultaneous separation could often be achieved only by using combined buffer with two different CDs. Chiral separation of major flavanones in sweet orange, mandarine and grapefruit juices raised more difficulties than in lemon and sour orange juices as narirutin will not readily build complexes with most CDs. Diastereomeric flavanones of mature and immature grapefruits were compared and some differences were found: naringin showed different diastereomeric ratio and 2S-prunin appeared only in immature grapefruit. Marmalade was also examined by chiral CE. Its major flavanones corresponded to flavanone pattern of mixed sour and sweet oranges.

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“…For the first time in 1886, Piutti isolated D-asparagine, the M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 4 enantiomer of L-asparagine, demonstrating that these compounds are sweet and tasteless, respectively [9]. After this discovery, other compounds were shown to have different taste characteristics according to their stereochemistry, such as naringin diastereoisomers with their distinct bitterness [10], and alapyridaine enantiomers whose dextrorotary form has a sweet taste whereas the levorotatory form has no taste at all [11].…”

Section: Introductionmentioning

confidence: 99%

How stereochemistry influences the taste of wine: Isolation, characterization and sensory evaluation of lyoniresinol stereoisomers

Cretin

Sallembien

Sindt

et al. 2015

Analytica Chimica Acta

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C-2 stereochemistry of naringin and its relation to taste and biosynthesis in maturing grapefruit

Cited by 49 publications

References 16 publications

Chiral HPLC separation and CD spectra of the C‐2 diastereomers of naringin in grapefruit during maturation

Chiral HPLC separation and CD spectra of the C‐2 diastereomers of naringin in grapefruit during maturation

Chiral separation of diastereomeric flavanone‐7‐O‐glycosides in citrus by capillary electrophoresis

How stereochemistry influences the taste of wine: Isolation, characterization and sensory evaluation of lyoniresinol stereoisomers

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