The essential oil of patchouli,<i>Pogostemon cablin</i>: A review

Beek, T.A. van; Joulain, Daniel

doi:10.1002/ffj.3418

Cited by 125 publications

(105 citation statements)

References 184 publications

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“…8 Main component responsible for the typical woody patchouli scent is the terpene alcohol (−)-patchoulol with a percentage of 40-50%. [9][10][11] However, patchouli oil contains more than 20 other different terpenes that determine the complex composition of the oil. 5,8,11 The contained sesquiterpenoids have functionalized cyclic structures such as (−)-patchoulol, which are difficult to synthesize by chemical synthesis.…”

mentioning

confidence: 99%

Optimization of factors influencing enzyme activity and product selectivity and the role of proton transfer in the catalytic mechanism of patchoulol synthase

Ekramzadeh¹,

Brämer²,

Frister³

et al. 2019

Biotechnology Progress

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The patchoulol synthase (PTS) from Pogostemon cablin is a versatile sesquiterpene synthase and produces more than 20 valuable sesquiterpenes by conversion of the natural substrate farnesyl pyrophosphate (FPP). PTS has the potential to be used as a biocatalyst for the production of valuable sesquiterpenes such as (−)‐patchoulol. The objective of the present study is to develop an efficient biotransformation and to characterize the biocatalytic mechanism of the PTS in detail. For this purpose, soluble PTS was prepared using an optimized cultivation protocol and continuous downstream process with a purity of 98%. The PTS biotransformation was then optimized regarding buffer composition, pH‐value, and temperature for biotransformation as well as functional and kinetic properties to improve productivity. For the bioconversion of FPP, the highest enzyme activity was reached with the 2‐(N‐morphlino)ethanesulfonic acid (MES) buffer containing 10% (v/v) glycerol and 10 mM MgCl2 at pH 6.4 and 34°C. The PTS showed an unusual substrate inhibition for sesquiterpene synthases indicating an intermediate sesquiterpene formed in the active center. Deuteration experiments were used to gain further insights into the biocatalytic mechanism described in literature. Thus it could be shown that a second substrate binding site must be responsible for substrate inhibition and that further protonation and deprotonation steps are involved in the reaction mechanism.

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mentioning

confidence: 99%

Optimization of factors influencing enzyme activity and product selectivity and the role of proton transfer in the catalytic mechanism of patchoulol synthase

Ekramzadeh¹,

Brämer²,

Frister³

et al. 2019

Biotechnology Progress

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“…12 In general, EOs are considered to be safe, and they have been classified as generally recognized as safe (GRAS) by the American Food and Drug Administration. [13][14][15][16][17][18] The structure and characteristics of EOs and active compounds 19 and their prospective application in meat and bakery industries have been extensively studied. 5,[20][21][22][23][24][25] One interesting alternative to extend the shelf life of fish breading products is the incorporation of these natural additives to edible films.…”

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confidence: 99%

Shelf life extension of refrigerated breaded hake medallions packed into active edible fish gelatin films

et al. 2019

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Fish consumption has increased in recent years. However, fish meat is highly perishable, which demonstrates the need for technologies to preserve its quality. Edible films might provide an alternative to extend the shelf life of fish. The goal of this study was to evaluate the efficiency of edible fish gelatin films added with carvacrol (blended: FG-0.6CRV and grafted: FG/CRV-g-FG) on the quality retention of commercially available prefried breaded hake medallions (BHMs). Samples of BHM were wrapped into films, heat sealed, and stored at −4 ± 1°C for 49 days. Free carvacrol gelatin films and the unwrapped medallions were used as controls. After predetermined periods of time, samples were analysed in terms of microbiological and physicochemical properties. Overall the storage period, the total volatile basic nitrogen value (TVBN) and the total psychrotrophic bacteria counts (TPC) were significantly lesser in BHM wrapped in FG-0.6CRV than in the other samples. The total oxidation index (TOI), peroxide value (PV), and p-anisidine value (AV) were reduced by 18%, 30%, and 16%, respectively, compared with controls. FG/CRV-g-FG film was not efficient to reduce the microbial spoilage or the oxidation, probably due to the retention of CRV into the matrix avoiding its migration towards the foodstuff, proving the importance of checking the films functionality in real food systems. Sensory evaluation of fried samples wrapped in FG-0.6CRV was also performed. The results indicate that the medallions can be directly cooked and consumed without removing the packaging with a good acceptance by the consumer. KEYWORDS active films, breaded hake medallions, carvacrol, fish gelatin, shelf life

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“…The history of patchouli alcohol 39 from its isolation till date has narrated in a recent exhaustive review article [26]. Biosynthetic pathways were proposed based on experimental work for the conversion of FPP to patchouli alcohol 39 (Scheme 14).…”

Section: Biosynthesis Of Patchouli Alcohol (Patchoulol)mentioning

confidence: 99%

Recent Developments in Selected Sesquiterpenes: Molecular Rearrangements, Biosynthesis, and Structural Relationship among Congeners

Paknikar¹,

Fondekar²

2018

Terpenes and Terpenoids

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Recent developments in selected sesquiterpenoids are reviewed for the past one decade (2005-2017) with special reference to Mechanisms of multistep molecular rearrangements of some sesquiterpenes or derivatives based on isotopic labeling studies and extensive spectroscopic analysis such as molecular rearrangement of acetyl cedrene to cedrene follower, acid catalyzed rearrangement of moreliane-based triketone, synthesis of (−)-isocomene and (−)-triquinane by acid-catalyzed rearrangement of (−)-modhephene, Total synthesis of (+)-cymbodiacetal, BF 3 catalyzed molecular rearrangements of mono epoxides of α-and β-himachalenes, santonic acid: Zn-HCl-ether reduction. Insights into biosynthesis of albaflavenone, caryol-1(11)-ene-10-ol, (+)-koraiol, pogostol, patchouli alcohol and valerenadiene are discussed. Congeners for probing structure-biosynthetic relationship. This approach is discussed with the availability of very interesting results on the isolation of highly oxygenated secondary metabolites from endophytic fungi, Xylaria sp.

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The essential oil of patchouli,Pogostemon cablin: A review

Cited by 125 publications

References 184 publications

Optimization of factors influencing enzyme activity and product selectivity and the role of proton transfer in the catalytic mechanism of patchoulol synthase

Optimization of factors influencing enzyme activity and product selectivity and the role of proton transfer in the catalytic mechanism of patchoulol synthase

Shelf life extension of refrigerated breaded hake medallions packed into active edible fish gelatin films

Recent Developments in Selected Sesquiterpenes: Molecular Rearrangements, Biosynthesis, and Structural Relationship among Congeners

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