Friedelin, the Major Component of Grapefruit Epicuticular Wax

Nordby, Harold E.; McDonald, Roy E.

doi:10.1021/jf00039a021

Cited by 24 publications

(14 citation statements)

References 24 publications

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“…Recently, the biological properties of this compound, including antiinflammatory, analgestic and antipyretic activities, were investigated (Antonisamy et al 2011). Other triterpenoids, including α- and β-amyrin, α- and β- amyrin acetate, the ketones: α- and β-amyrone, and 24-methylenecycloartanol (Table 2) were also detected in the fruit cuticular wax of Marsch grapefruit grown in central Florida (Norby and McDonald 1994). Lupeol and two other compounds, tentatively assigned as D:B-friedo-B′:A′-neogammacer-5-en-ol and D:C-friedooleanen-3-one (another ketone), were subsequently added to this triterpenoid profile (Norby and McDonald 1995).…”

Section: Edible Fruits With Inedible Peelmentioning

confidence: 99%

“…cv. Marshα-amyrin; β-amyrin; α-amyrin acetate; β-amyrin acetate; α-amyrone; β-amyrone; friedelin; 24-methylenecycloartanol49.3 % of the total wax extractFriedelin (27.9 % of wax extract)Immersion of whole fruits in chloroformGC–MSNorby and McDonald (1994)Sweet cherry ( P. avium L.) cv. Kordiaα-amyrin; hederagenin and its isomers*; oleanolic acid; ursolic acid; uvaol75.6 % of the total wax extract (in mature fruit)Ursolic acid (60 % of wax extract); oleanolic acid (7.5 % of wax extract)Extraction of enzymatically isolated cuticle with chloroformGC–MSPeschel et al (2007)

* Tentative identification

GC – MS gas chromatography–mass spectrometry

…”

Section: Other Fruits With Edible Peelmentioning

confidence: 99%

“…), where they account for 50 % of total wax. Furthermore, ursolic acid was not detected in grapefruit cuticular waxes, and the predominant compound was identified as the triterpene ketone, friedelin (Norby and McDonald 1994). Friedelin (Fig.…”

Section: Edible Fruits With Inedible Peelmentioning

confidence: 99%

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Fruit cuticular waxes as a source of biologically active triterpenoids

et al. 2012

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Section: Edible Fruits With Inedible Peelmentioning

confidence: 99%

* Tentative identification

GC – MS gas chromatography–mass spectrometry

…”

Section: Other Fruits With Edible Peelmentioning

confidence: 99%

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Fruit cuticular waxes as a source of biologically active triterpenoids

et al. 2012

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“…In summary, alkanes, aldehydes, primary alcohols, fatty acids and triterpenoids are the major wax fractions in citrus fruits (Albrigo 1972;Baker et al 1975;Freeman et al 1979;El-Otmani and Coggins 1985;El-Otmani et al 1986;Sala et al 1992;McDonald et al 1993;Nordby and McDonald 1994;Sala 2000;Cajuste et al 2010;Liu et al 2012;Wang et al 2014). However, in most previous studies, fruit waxes were extracted by dipping the intact surface of an organ into organic solvents.…”

Section: Aliphatic Compounds Dominated the Epicuticular Waxes Whereamentioning

confidence: 99%

Analysis of cuticular wax constituents and genes that contribute to the formation of ‘glossy Newhall’, a spontaneous bud mutant from the wild-type ‘Newhall’ navel orange

et al. 2015

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Navel orange (Citrus sinensis [L.] Osbeck) fruit surfaces contain substantial quantities of cuticular waxes, which have important eco-physiological roles, such as water retention and pathogen defense. The wax constituents of ripe navel orange have been studied in various reports, while the wax changes occurring during fruit development and the molecular mechanism underlying their biosynthesis/export have not been investigated. Recently, we reported a spontaneous bud mutant from the wild-type (WT) 'Newhall' Navel orange. This mutant displayed unusual glossy fruit peels and was named 'glossy Newhall' (MT). In this study, we compared the developmental profiles of the epicuticular and intracuticular waxes on the WT and MT fruit surfaces. The formation of epicuticular wax crystals on the navel orange surface was shown to be dependent on the accumulation of high amounts of aliphatic wax components with trace amounts of terpenoids. In sharp contrast, the underlying intracuticular wax layers have relatively low concentrations of aliphatic wax components but high concentrations of cyclic wax compounds, especially terpenoids at the late fruit developmental stages. Our work also showed that many genes that are involved in wax biosynthesis and export pathways were down-regulated in MT fruit peels, leading to a decrease in aliphatic wax component amounts and the loss of epicuticular wax crystals, ultimately causing the glossy phenotype of MT fruits.

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“…Cuticular waxes are complex mixtures consisting mostly of very-long-chain (VLC, i.e., >C 20 ) aliphatics, such as fatty acids, primary alcohols, alkyl esters, aldehydes, alkanes, secondary alcohols and ketones [3]. In many species, the wax mixtures also comprise alicyclics, including a wide variety of triterpenoids [4][5][6][7][8], and in some species also aromatics such as 5-alkylresorcinols [9,10], benzyl and phenethyl esters [11][12][13][14][15], and 4-hydroxyphenylpropyl, 3,4-dihydroxyphenylpropyl and 3,4-dihydroxyphenylbutyl esters [16,17].…”

Section: Introductionmentioning

confidence: 99%

Identification of Polyketides in the Cuticular Waxes of Triticum aestivum cv. Bethlehem

Racoviţǎ

Jetter

2016

Lipids

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Cuticular waxes are complex mixtures consisting mostly of very-long-chain aliphatics with single, primary functional groups. However, the waxes of many plant species also include aliphatics with one or more functional groups residing on subterminal or mid-chain carbons. In the present work, the cuticular wax mixtures from flag leaf blades and peduncles of Triticum aestivum cv. Bethlehem were analyzed in a search for novel wax constituents with in-chain functionalities, potentially of polyketide origin. The structures of compounds belonging to six different compound classes were elucidated using gas chromatography-mass spectrometry of various derivatives. Among them, a series of 2,4-ketols was identified, with odd carbon numbers ranging from C to C and peaking at C. The analogous C 2,4-diketone was identified as well, together with a pair of co-eluting C mid-chain β-ketol isomers (16-hydroxyhentriacontan-14-one and 14-hydroxyhentriacontan-16-one), a pair of co-eluting C mid-chain α-ketol isomers (15-hydroxytriacontan-14-one and 14-hydroxytriacontan-15-one), the corresponding C 14,15-diketone, and a pair of co-eluting C ketones (hentriacontan-14-one and hentriacontan-16-one). All newly discovered structures contain ketone functional groups, with similar CH and CH alkyl chains on either side of the functionalities, thus resembling the previously reported very-long-chain β-diketones dominating the wheat wax mixtures. Based on these structural characteristics, possible biosynthetic pathways leading to the newly identified polyketide-like compounds are proposed.

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Friedelin, the Major Component of Grapefruit Epicuticular Wax

Cited by 24 publications

References 24 publications

Fruit cuticular waxes as a source of biologically active triterpenoids

Fruit cuticular waxes as a source of biologically active triterpenoids

Analysis of cuticular wax constituents and genes that contribute to the formation of ‘glossy Newhall’, a spontaneous bud mutant from the wild-type ‘Newhall’ navel orange

Identification of Polyketides in the Cuticular Waxes of Triticum aestivum cv. Bethlehem

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