Pheromone Study on Acarid Mites XI. Function of Mite Body as Geometrical Isomerization and Reduction of Citral (the Alarm Pheromone)

Kuwahara, Yasumasa; Suzuki, Hiroshi; Matsumoto, Katsuhiko; Wada, Yoshitake

doi:10.1303/aez.18.30

Cited by 37 publications

(25 citation statements)

References 9 publications

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“…This disagreement suggests that the geranial produced by ZoGeDH in vivo is secreted into specialized cells under a structurally stable condition. The ratio of cis-trans isomerization of citral is reported to be dependent on solvent (Kuwahara et al 1983). Therefore, the condition where geranial was stored should be the key factor for structural stability of geranial.…”

Section: Discussionmentioning

confidence: 99%

Biosynthesis of geranial, a potent aroma compound in ginger rhizome (<i>Zingiber officinale</i>): Molecular cloning and characterization of geraniol dehydrogenase

Iijima

Koeduka

Suzuki

et al. 2014

Plant Biotechnology

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Fresh ginger (Zingiber officinale) rhizome is characterized by a pleasant citrus aroma and pungent flavor. The majority of the aroma-contributing volatiles are monoterpenoids, especially geraniol derivatives such as geranial, geranyl acetate, geraniol and citronellol. In this study, we investigated the interconversion of geraniol derivatives by incorporation experiments using deuterium-labeled geraniol and geranyl acetate. GC-MS analysis revealed that the incorporated geraniol and geranyl acetate were transformed and detected as geranial, geraniol, geranyl acetate and citronellol; however, nerol and neral were hardly detected. Next, we isolated and characterized a cDNA encoding geraniol dehydrogenase (ZoGeDH) by expressed sequence tag database mining. Phylogenic analysis of ZoGeDH resulted in its categorization into the cinnamyl alcohol dehydrogenase (CAD) group, along with the previously reported GeDHs of sweet basil (Ocimum basilicum) and wild perilla (P. setoyensis, P. citriodora, and P. frutescens). The recombinant ZoGeDH catalyzed the NADP-dependent oxidation from geraniol to citral. Furthermore, its substrate specificity was the highest for geraniol and nerol, while that for cinnamyl alcohol was 32% of the activity observed for geraniol. The expression levels of ZoGeDH in various ginger plant tissues were in accordance with the accumulation of geranial, except in old rhizome.

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Section: Discussionmentioning

confidence: 99%

Biosynthesis of geranial, a potent aroma compound in ginger rhizome (<i>Zingiber officinale</i>): Molecular cloning and characterization of geraniol dehydrogenase

Iijima

Koeduka

Suzuki

et al. 2014

Plant Biotechnology

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“…These two products are measurable quickly after disturbance in mite whole-body extracts, indicating rapid and spontaneous chemical reactions. The mechanism of this breakdown is unknown, but it has been shown that mites possess surface-associated enzymes that contribute to previously unsuspected chemical reactions (29)(30)(31). Finally, when exposed to water in the humid environment, benzoyl cyanide hydrolyzes to benzoic acid and HCN (32,33).…”

Section: Resultsmentioning

confidence: 99%

Storage and release of hydrogen cyanide in a chelicerate ( Oribatula tibialis )

Brückner

Raspotnig

Wehner

et al. 2017

Proc. Natl. Acad. Sci. U.S.A.

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Cyanogenesis denotes a chemical defensive strategy where hydrogen cyanide (HCN, hydrocyanic or prussic acid) is produced, stored, and released toward an attacking enemy. The high toxicity and volatility of HCN requires both chemical stabilization for storage and prevention of accidental self-poisoning. The few known cyanogenic animals are exclusively mandibulate arthropods (certain myriapods and insects) that store HCN as cyanogenic glycosides, lipids, or cyanohydrins. Here, we show that cyanogenesis has also evolved in the speciose Chelicerata. The oribatid mite Oribatula tibialis uses the cyanogenic aromatic ester mandelonitrile hexanoate (MNH) for HCN storage, which degrades via two different pathways, both of which release HCN. MNH is emitted from exocrine opisthonotal oil glands, which are potent organs for chemical defense in most oribatid mites.

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“…Citral is also used as a flavour and for fortifying lemon oil. It also has strong anti-microbial qualities [4] and pheromonal effects in insects [5]. Citrals are basic intermediate for synthesis of flavouring and fragrance components such as Ionones, methyl ionones and vitamins A and E [6,7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3, 7-Dimethyl-2, 6-Octadienal Acetals from Citral Extracted from Lemon Grass, Cymbopogon citrates L.

Shahzadi¹,

Muhammad²,

Mehmood³

et al. 2014

J Antivir Antiretrovir

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Citral (3, 7-dimethyl-2, 6-octadienal)was hydro distilled from lemon grass and 3, 7-dimethyl-2, 6-octadienal acetals (Citral acetals) were synthesized from it. The latter was redistilled under vacuum and collected fractions at constant temperature. Para toluene sulphonic acid catalyst was used for the preparation of citral ethylene glycol acetal and citral propylene glycol acetal which are used in perfumery, flavor, for fortifying lemon oil. GC, IR of synthesized product is recorded and graphs were determined.

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Pheromone Study on Acarid Mites XI. Function of Mite Body as Geometrical Isomerization and Reduction of Citral (the Alarm Pheromone)

Cited by 37 publications

References 9 publications

Biosynthesis of geranial, a potent aroma compound in ginger rhizome (<i>Zingiber officinale</i>): Molecular cloning and characterization of geraniol dehydrogenase

Biosynthesis of geranial, a potent aroma compound in ginger rhizome (<i>Zingiber officinale</i>): Molecular cloning and characterization of geraniol dehydrogenase

Storage and release of hydrogen cyanide in a chelicerate ( Oribatula tibialis )

Synthesis of 3, 7-Dimethyl-2, 6-Octadienal Acetals from Citral Extracted from Lemon Grass, Cymbopogon citrates L.

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