Biosynthesis of floral scent 2-phenylethanol in rose flowers

Hirata, Hiroshi; Ohnishi, Toshiyuki; Watanabe, Naoharu

doi:10.1080/09168451.2016.1191333

Cited by 43 publications

(24 citation statements)

References 63 publications

(68 reference statements)

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“…Another detected compound was phenylethyl alcohol (Table 1), an aromatic alcohol produced by some Streptomyces spp. [18,63,64,125] and by plants such as rose [65]. It has been shown to function as an insect repellent against Rhodnius prolixus (Family: Reduviidae) and Triatoma infestans (kissing bug), both of which are vectors of the Chagas disease parasite [77].…”

Section: Identification Of Previously Reported Streptomyces-specific mentioning

confidence: 99%

Production of Plant-Associated Volatiles by Select Model and Industrially Important Streptomyces spp.

et al. 2020

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The Streptomyces produce a great diversity of specialized metabolites, including highly volatile compounds with potential biological activities. Volatile organic compounds (VOCs) produced by nine Streptomyces spp., some of which are of industrial importance, were collected and identified using gas chromatography–mass spectrometry (GC-MS). Biosynthetic gene clusters (BGCs) present in the genomes of the respective Streptomyces spp. were also predicted to match them with the VOCs detected. Overall, 33 specific VOCs were identified, of which the production of 16 has not been previously reported in the Streptomyces. Among chemical classes, the most abundant VOCs were terpenes, which is consistent with predicted biosynthetic capabilities. In addition, 27 of the identified VOCs were plant-associated, demonstrating that some Streptomyces spp. can also produce such molecules. It is possible that some of the VOCs detected in the current study have roles in the interaction of Streptomyces with plants and other higher organisms, which might provide opportunities for their application in agriculture or industry.

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Section: Identification Of Previously Reported Streptomyces-specific mentioning

confidence: 99%

Production of Plant-Associated Volatiles by Select Model and Industrially Important Streptomyces spp.

et al. 2020

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“…In the phenyllactic acid-producing fungal strains, phenylalanine aminotransferase and phenylpyruvate reductase act sequentially in the transformation of phenylalanine to phenyllactic acid ( Fujii et al, 2011 ). Phenylalanine aminotransferase was also identified from rose ( Hirata et al, 2012 , 2016 ) and Cucumis melo ( Gonda et al, 2010 ). Although phenyllactic acid was not detected from Arabidopsis , both HPPR2 and HPPR3 can use phenylpyruvic acid as substrate ( Table 1 ).…”

Section: Discussionmentioning

confidence: 99%

Characterization of Arabidopsis thaliana Hydroxyphenylpyruvate Reductases in the Tyrosine Conversion Pathway

Fang

et al. 2018

Front. Plant Sci.

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Tyrosine serves as a precursor to several types of plant natural products of medicinal or nutritional interests. Hydroxyphenylpyruvate reductase (HPPR), which catalyzes the reduction of 4-hydroxyphenylpyruvic acid (pHPP) to 4-hydroxyphenyllactic acid (pHPL), has been shown to be the key enzyme in the biosynthesis of rosmarinic acid (RA) from tyrosine and, so far, HPPR activity has been reported only from the RA-accumulating plants. Here, we show that HPPR homologs are widely distributed in land plants. In Arabidopsis thaliana, which does not accumulate RA at detectable level, two homologs (HPPR2 and HPPR3) are functional in reducing pHPP. Phylogenetic analysis placed HPPR2 and HPPR3 in two separate groups within the HPPR clade, and HPPR2 and HPPR3 are distinct from HPR1, a peroxisomal hydroxypyruvate reductase (HPR). In vitro characterization of the recombinant proteins revealed that HPPR2 has both HPR and HPPR activities, whereas HPPR3 has a strong preference for pHPP, and both enzymes are localized in the cytosol. Arabidopsis mutants defective in either HPPR2 or HPPR3 contained lower amounts of pHPL and were impaired in conversion of tyrosine to pHPL. Furthermore, a loss-of-function mutation in tyrosine aminotransferase (TAT) also reduced the pHPL accumulation in plants. Our data demonstrate that in Arabidopsis HPPR2 and HPPR3, together with TAT1, constitute to a probably conserved biosynthetic pathway from tyrosine to pHPL, from which some specialized metabolites, such as RA, can be generated in specific groups of plants. Our finding may have broad implications for the origins of tyrosine-derived specialized metabolites in general.

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“…The main flavor component on the scent of rose flowers are -damascone and damascenone (Pal, 2013). Nevertheless, it is also known that characteristic odor of rose flowers came from 2-phenylethyl alcohol which being a principal component in rose water (Watanabe et al 2001;Sakai et al 2007;Sakai et al 2008;Kumar et al 2014;Gunes, 2005;Hirata et al 2016). Previous researches explained that bioactive molecule of 2phenylethyl alcohol inside rose flowers is in the form of 2-phenylethyl-D-glucopyranoside (Eikani et al 2005;Watanabe et al 2002).…”

Section: Introductionmentioning

confidence: 99%

Essential Oil Composition of Rose Flowers from Karangpring Village Jember District Extracted by Distillation and Enfleurage

et al. 2019

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Karangpring is one tourist destination villages in Jember district which is popular with beautiful large rose field areas. Therefore, this area grows to be a leading producer of rose flowers in Jember district. However, the bulky presence of these flowers made its price becomes lower in regular days. Local community only uses and sells these fresh flowers as the flower for funeral. The rose flower has a great potency to be explored as a source of rose essential oil production. To date, there is no previous research on studying rose flowers from Karangpring village for its potency on the essential oil production. In this research, rose flowers were subjected to be extracted of its essential oil using two extraction methods, distillation, and enfleurage. Hydrodistillation resulted two phases of distillates, above part formed a cloudy white phase as a normal essential oil extracted from plants, and the lower phase was an aqueous phase containing rose hydrosols. Both phases of these condensates were analyzed using GCMS. Data explained that above phase, with a yield oil of 0.07%, only contains long-chain hydrocarbons such as n-nonadecane, n-heptadecane, 9-nonadecene, and eicosane, while the lower phase only contains 2-phenylethyl alcohol. On the other hand, enfleurage of fresh rose flowers resulted in 0.06% oil yield. GCMS analysis of this oil shows that 2-phenylethyl alcohol, eugenol, and phenylacetic acid are three major compounds which take more than 85% of total rose absolute. The results show that enfleurage is a better method for extracting rose oil in better quality than using the distillation method, in term of the variety of volatile components. Meanwhile, hydrodistillation is still benefiting from producing rose water that is qualified as an industrial additive agent for food and cosmetic productions or even a new potent of agromedicine products. Keywords: rose, rose oil, rose water, rose absolute, distillation, enfleurage.

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Biosynthesis of floral scent 2-phenylethanol in rose flowers

Cited by 43 publications

References 63 publications

Production of Plant-Associated Volatiles by Select Model and Industrially Important Streptomyces spp.

Production of Plant-Associated Volatiles by Select Model and Industrially Important Streptomyces spp.

Characterization of Arabidopsis thaliana Hydroxyphenylpyruvate Reductases in the Tyrosine Conversion Pathway

Essential Oil Composition of Rose Flowers from Karangpring Village Jember District Extracted by Distillation and Enfleurage

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