On the Scent of Orchids

Kaiser, Roman

doi:10.1021/bk-1993-0525.ch018

Cited by 140 publications

(47 citation statements)

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“…(E)-␤-Ocimene constitutes 87% of the scent of the orchid Laelia anceps (Kaiser, 1993), whereas the scent of Brugmansia ϫ candida, a member of the Solanaceae, contains as much as 52% (E)-␤-ocimene (Kite and Leon, 1995). In snapdragon, the monoterpene fraction of the floral scent bouquet is dominated by (E)-␤-ocimene and myrcene, which account for 20 and 8% of total floral volatiles, respectively .…”

Section: Monoterpene Synthases Involved In Snapdragon Floral Scent Bimentioning

confidence: 99%

(E)-β-Ocimene and Myrcene Synthase Genes of Floral Scent Biosynthesis in Snapdragon: Function and Expression of Three Terpene Synthase Genes of a New Terpene Synthase Subfamily

et al. 2003

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Snapdragon flowers emit two monoterpene olefins, myrcene and ( E )-␤ -ocimene, derived from geranyl diphosphate, in addition to a major phenylpropanoid floral scent component, methylbenzoate. Emission of these monoterpenes is regulated developmentally and follows diurnal rhythms controlled by a circadian clock. Using a functional genomics approach, we have isolated and characterized three closely related cDNAs from a snapdragon petal-specific library that encode two myrcene synthases ( ama1e20 and ama0c15 ) and an ( E )-␤ -ocimene synthase ( ama0a23 ). Although the two myrcene synthases are almost identical (98%), except for the N-terminal 13 amino acids, and are catalytically active, yielding a single monoterpene product, myrcene, only ama0c15 is expressed at a high level in flowers and contributes to floral myrcene emission. ( E )-␤ -Ocimene synthase is highly similar to snapdragon myrcene synthases (92% amino acid identity) and produces predominantly ( E )-␤ -ocimene (97% of total monoterpene olefin product) with small amounts of ( Z )-␤ -ocimene and myrcene. These newly isolated snapdragon monoterpene synthases, together with Arabidopsis AtTPS14 (At1g61680), define a new subfamily of the terpene synthase (TPS) family designated the Tps-g group. Members of this new Tps-g group lack the RRx 8 W motif, which is a characteristic feature of the Tps-d and Tps-b monoterpene synthases, suggesting that the reaction mechanism of Tps-g monoterpene synthase product formation does not proceed via an RR-dependent isomerization of geranyl diphosphate to 3S -linalyl diphosphate, as shown previously for limonene cyclase. Analyses of tissue-specific, developmental, and rhythmic expression of these monoterpene synthase genes in snapdragon flowers revealed coordinated regulation of phenylpropanoid and isoprenoid scent production.

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Section: Monoterpene Synthases Involved In Snapdragon Floral Scent Bimentioning

confidence: 99%

(E)-β-Ocimene and Myrcene Synthase Genes of Floral Scent Biosynthesis in Snapdragon: Function and Expression of Three Terpene Synthase Genes of a New Terpene Synthase Subfamily

et al. 2003

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“…Specifically, benzylacetate, benzylbenzoate, and methylsalicylate are found in the scent of many mothpollinated flowers (Kaiser, 1993;. In addition, methylsalicylate is also reported to be important in plant defense and communication (Dicke et al, 1990;Shulaev et al, 1997).…”

Section: Beat and Samt Activity In Flower Partsmentioning

confidence: 99%

Floral Scent Production in Clarkia breweri1

et al. 1998

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The fragrance of Clarkia breweri (Onagraceae), a California annual plant, includes three benzenoid esters: benzylacetate, benzylbenzoate, and methylsalicylate. Here we report that petal tissue was responsible for the benzylacetate and methylsalicylate emission, whereas the pistil was the main source of benzylbenzoate. The activities of two novel enzymes, acetyl-coenzyme A:benzylalcohol acetyltransferase (BEAT), which catalyzes the acetyl esterification of benzylalcohol, andS-adenosyl-l-methionine:salicylic acid carboxyl methyltransferase, which catalyzes the methyl esterification of salicylic acid, were also highest in petal tissue and absent in leaves. In addition, the activity of both enzymes in the various floral organs was developmentally and differentially regulated.S-Adenosyl-l-methionine:salicylic acid carboxyl methyltransferase activity in petals peaked in mature buds and declined during the next few days after anthesis, and it showed a strong, positive correlation with the emission of methylsalicylate. The levels of BEAT activity and benzylacetate emission in petals also increased in parallel as the buds matured and the flowers opened, but as emission began to decline on the 2nd d after anthesis, BEAT activity continued to increase and remained high until the end of the lifespan of the flower.

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“…Thus, its natural occurrence in plants might be much more common than we ever realized. In fact, the emission of this isoprene alcohol from plants had been observed before; the orchid Aerides lawrenceae produces MB [18]. Interestingly, MB is also a hop constituent with sedative hypnotic activity [19] and formed from humulones and lupulones by reaction with OH radicals in the presence of atmospheric oxygen [20].…”

Section: Plantmentioning

confidence: 99%

2-methyl-3-buten-2-ol: A Pheromone Component of Conifer Bark Beetles Found in the Bark of Nonhost Deciduous Trees

Zhang

Schlyter

Birgersson

2012

Psyche: A Journal of Entomology

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Volatiles from bark of aspen, Populus tremula L. and two species of birch: silver birch (Betula pendula Roth.) and common birch (B. pubescens Ehrh.), were collected by direct solvent extraction and aeration of both newly cut bark chips and undamaged stems in June 1998 and subjected to GC-MS analysis. The results showed the presence of 2-methyl-3-buten-2-ol (MB), one of the two principal aggregation pheromone components of the spruce bark beetle, Ips typographus, in bark extraction samples of all the three deciduous tree species tested. In addition, one more oxygenated hemiterpene, 3-methyl-3-buten-2-one, and (E)-3-penten-2-ol were also found in the bark extracts. Only trace amounts of MB were detected in some aeration samples of the fresh bark chips, and no MB was found from the aeration samples of undamaged stems at detectable levels. The occurrence of this compound was also confirmed in the bark of four exotic birch species: B. albosinensis Schneid., B. ermanii Cham., B. jacquemontii Spach, and B. maximowicziana Regel, but not yet in the European pines/spruces and the common yeasts. Our results raise major questions regarding the evolution, the tropospheric chemistry, and the ecological role of this hemiterpene alcohol. They also suggest that comparative studies on the biosynthetic pathways for MB in different sources would be of considerably evolutionary interest.

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On the Scent of Orchids

Cited by 140 publications

References 0 publications

(E)-β-Ocimene and Myrcene Synthase Genes of Floral Scent Biosynthesis in Snapdragon: Function and Expression of Three Terpene Synthase Genes of a New Terpene Synthase Subfamily

(E)-β-Ocimene and Myrcene Synthase Genes of Floral Scent Biosynthesis in Snapdragon: Function and Expression of Three Terpene Synthase Genes of a New Terpene Synthase Subfamily

Floral Scent Production in Clarkia breweri1

2-methyl-3-buten-2-ol: A Pheromone Component of Conifer Bark Beetles Found in the Bark of Nonhost Deciduous Trees

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