Sesquiterpenes. I. Nootkatone, A New Grapefruit Flavor Constituent

MacLeod, William D.; Buigues, Nelida M.

doi:10.1111/j.1365-2621.1964.tb00411.x

Cited by 107 publications

(44 citation statements)

References 8 publications

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“…Octyl acetate was a major component of esters. Nootkatone is an important indicator for identifying the species of C. grandis and C. paradisi (Sawamura et al, 1991(Sawamura et al, , 1994b, as well as one of the character-impact compounds of grapefruit (MacLeod & Buigues, 1964;Nursten, 1979;Demole & Enggist, 1983). Thirteen additional compounds identified in the CPO analysis of the oxygenated fraction were: hexyl acetate, allyl caproate, isopulegol, camphene hydrate, menthol, isooctanol, citronellyl acetate, dodecanal, geranyl propionate, cis-caryophyllene oxide, a-eudesmol, isopinocampherol and b-ionol.…”

Section: Resultsmentioning

confidence: 99%

Characteristic Aroma Components of Tosa-buntan(Citrus grandis Osbeck forma Tosa) Fruit.

Sawamura

Song

Choi

et al. 2001

FSTR

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The volatile components of Tosa-buntan (Citrus grandis Osbeck forma Tosa) cold-pressed peel oil were studied by GC and GC-MS. The characteristic aroma compounds were investigated by GC-olfactometry in which a semi-bore capillary column, DB-Wax, was used for effective separation of the volatile components of the oil. Hydrocarbons including mono and sesquiterpenes of the oil accounted for about 98% of the volatile components. The characteristic flavor was also present in the oxygenated fraction. Flavor dilution (FD) factors of the volatile flavor components of the cold-pressed oil were determined by aroma extraction dilution analysis. The relative flavor activity derived from FDfactor and peak area percent was used in this experiment. It was suggested that compounds with higher relative flavor activity such as decanoic acid, heptyl acetate, a a a a-bisabolol, nonanal, cis, trans-farnesol, trans-nerolidol and 2-dodecenal would contribute to Tosa-buntan flavor. Careful sniff testing revealed 2-dodecenal to be a characteristic or key compound of Tosa-buntan aroma. A solution of this authentic compound below 2 ppm gave a pleasant and refreshing aroma similar to Tosa-buntan flavor.

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Section: Resultsmentioning

confidence: 99%

Characteristic Aroma Components of Tosa-buntan(Citrus grandis Osbeck forma Tosa) Fruit.

Sawamura

Song

Choi

et al. 2001

FSTR

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“…The sesquiterpenes valencene and a-and b-sinensal, although present in minor quantities in oranges, play an important role in the overall flavor and aroma of orange fruit (Maccarone et al, 1998;Vora et al, 1983;Weiss, 1997). Nootkatone, a putative derivative of valencene, is a small fraction of the essential oils, but has a dominant role in the flavor and aroma of grapefruit (MacLeod and Buigues, 1964;Shaw and Wilson, 1981), while the monoterpene S-linalool was found to be an important general strawberry aroma compound Larsen and Poll, 1992) and is found in many other fruits including peaches, guavas, nectarines, papayas, mangoes, passion fruits, tomatoes, litchi, oranges, prickly pears and koubos (Baldwin et al, 2000;Bernreuther and Schreier, 1991;Flath and Takahashi, 1978;Idstein et al, 1985;Ninio et al, 2003;Ong and Acree, 1998;Visai and Vanoli, 1997). The combination of the monoterpenes geraniol, citronellol and rose oxide is a key component of the characteristic aroma of aromatic muscat grapes as well as the special scent of roses (Bayrak, 1994;Dunphy and Allcock, 1972;Luan et al, 2005).…”

Section: Carbohydrate-derived Flavor Compoundsmentioning

confidence: 99%

Biosynthesis of plant‐derived flavor compounds

Schwab¹,

Davidovich‐Rikanati²,

Lewinsohn³

2008

The Plant Journal

944

704

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SummaryPlants have the capacity to synthesize, accumulate and emit volatiles that may act as aroma and flavor molecules due to interactions with human receptors. These low-molecular-weight substances derived from the fatty acid, amino acid and carbohydrate pools constitute a heterogenous group of molecules with saturated and unsaturated, straight-chain, branched-chain and cyclic structures bearing various functional groups (e.g. alcohols, aldehydes, ketones, esters and ethers) and also nitrogen and sulfur. They are commercially important for the food, pharmaceutical, agricultural and chemical industries as flavorants, drugs, pesticides and industrial feedstocks. Due to the low abundance of the volatiles in their plant sources, many of the natural products had been replaced by their synthetic analogues by the end of the last century. However, the foreseeable shortage of the crude oil that is the source for many of the artifical flavors and fragrances has prompted recent interest in understanding the formation of these compounds and engineering their biosynthesis. Although many of the volatile constituents of flavors and aromas have been identified, many of the enzymes and genes involved in their biosynthesis are still not known. However, modification of flavor by genetic engineering is dependent on the knowledge and availability of genes that encode enzymes of key reactions that influence or divert the biosynthetic pathways of plant-derived volatiles. Major progress has resulted from the use of molecular and biochemical techniques, and a large number of genes encoding enzymes of volatile biosynthesis have recently been reported.

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“…The sesquiterpenes valencene, alpha-and beta-sinensal, which are present in minor quantities in oranges, play an important role in the overall avor and aroma of orange fruit (Maccarone et al, 1998;Vora et al, 1983;Weiss, 1997). Nootkatone, a putative derivative of valencene, composes a small fraction of the essential oils, but has a dominant role in the¯avor and aroma of grapefruit (Macleod and Buigues, 1964;Shaw and Wilson, 1981). The pro®le of these and other terpenoid volatiles in various citrus species and their importance as aroma compounds are well known.…”

Section: Introductionmentioning

confidence: 99%

Citrus fruit flavor and aroma biosynthesis: isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene

Sharon-Asa¹,

Shalit²,

Frydman³

et al. 2003

The Plant Journal

190

125

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SummaryCitrus fruits possess unique aromas rarely found in other fruit species. While fruit flavor is composed of complex combinations of soluble and volatile compounds, several low‐abundance sesquiterpenes, such as valencene, nootkatone, alpha‐sinensal, and beta‐sinensal, stand out in citrus as important flavor and aroma compounds. The profile of terpenoid volatiles in various citrus species and their importance as aroma compounds have been studied in detail, but much is still lacking in our understanding of the physiological, biochemical, and genetic regulation of their production. Here, we report on the isolation, functional expression, and developmental regulation of Cstps1, a sesquiterpene synthase‐encoding gene, involved in citrus aroma formation. The recombinant enzyme encoded by Cstps1 was shown to convert farnesyl diphosphate to a single sesquiterpene product identified as valencene by gas chromatography–mass spectrometry (GC–MS). Phylogenetic analysis of plant terpene synthase genes localized Cstps1 to the group of angiosperm sesquiterpene synthases. Within this group, Cstps1 belongs to a subgroup of citrus sesquiterpene synthases. Cstps1 was found to be developmentally regulated: transcript was found to accumulate only towards fruit maturation, corresponding well with the timing of valencene accumulation in fruit. Although citrus fruits are non‐climacteric, valencene accumulation and Cstps1 expression were found to be responsive to ethylene, providing further evidence for the role of ethylene in the final stages of citrus fruit ripening. Isolation of the gene encoding valencene synthase provides a tool for an in‐depth study of the regulation of aroma compound biosynthesis in citrus and for metabolic engineering for fruit flavor characteristics.

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Sesquiterpenes. I. Nootkatone, A New Grapefruit Flavor Constituent

Cited by 107 publications

References 8 publications

Characteristic Aroma Components of Tosa-buntan(Citrus grandis Osbeck forma Tosa) Fruit.

Characteristic Aroma Components of Tosa-buntan(Citrus grandis Osbeck forma Tosa) Fruit.

Biosynthesis of plant‐derived flavor compounds

Citrus fruit flavor and aroma biosynthesis: isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene

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