Naturally Occurring Iridoids and Secoiridoids. An Updated Review, Part 4

Dinda, Biswanath; Debnath, Sudhan; Banik, Rajarshi

doi:10.1248/cpb.59.803

Cited by 132 publications

(72 citation statements)

References 91 publications

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“…Although extensive monoterpenol (especially linalool) oxidative metabolism has been described in many plant species, leading to fragrant and bioactive compounds as diverse as alcohols, aldehydes, acids, and epoxides (Williams et al, 1982;Matich et al, 2003Matich et al, , 2011Luan et al, 2005Luan et al, , 2006Ginglinger et al, 2013), pyranoid or furanoid linalool derivatives (Pichersky et al, 1994;Raguso and Pichersky, 1999), and geraniol-derived iridoids and secoiridoids (Dinda et al, 2007a(Dinda et al, , 2007b(Dinda et al, , 2011Tundis et al, 2008), limited information is available on the enzymes generating these oxygenated compounds. Involvement of a cytochrome P450 (P450) enzyme extracted from Vinca rosea (now renamed Catharanthus roseus) in the hydroxylation of geraniol and nerol was suggested as early as 1976 (Madyastha et al, 1976).…”

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confidence: 99%

Dual Function of the Cytochrome P450 CYP76 Family from Arabidopsis thaliana in the Metabolism of Monoterpenols and Phenylurea Herbicides

et al. 2014

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Comparative genomics analysis unravels lineage-specific bursts of gene duplications related to the emergence of specialized pathways. The CYP76C subfamily of cytochrome P450 enzymes is specific to Brassicaceae. Two of its members were recently associated with monoterpenol metabolism. This prompted us to investigate the CYP76C subfamily genetic and functional diversification. Our study revealed high rates of CYP76C gene duplication and loss in Brassicaceae, suggesting the association of the CYP76C subfamily with species-specific adaptive functions. Gene differential expression and enzyme functional specialization in Arabidopsis thaliana, including metabolism of different monoterpenols and formation of different products, support this hypothesis. In addition to linalool metabolism, CYP76C1, CYP76C2, and CYP76C4 metabolized herbicides belonging to the class of phenylurea. Their ectopic expression in the whole plant conferred herbicide tolerance. CYP76Cs from A. thaliana. thus provide a first example of promiscuous cytochrome P450 enzymes endowing effective metabolism of both natural and xenobiotic compounds. Our data also suggest that the CYP76C gene family provides a suitable genetic background for a quick evolution of herbicide resistance.Although extensive monoterpenol (especially linalool) oxidative metabolism has been described in many plant species, leading to fragrant and bioactive compounds as diverse as alcohols, aldehydes, acids, and epoxides

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confidence: 99%

Dual Function of the Cytochrome P450 CYP76 Family from Arabidopsis thaliana in the Metabolism of Monoterpenols and Phenylurea Herbicides

et al. 2014

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“…C-NMR signals were similar to those of genipin by comparing with the reported data. 5,10) It suggested that 1 should be an iridoid glycoside with a transferuloyl, and gentiobiosyl moieties, which were confirmed by 1 H-1 H correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC), and HMBC spectra. The nuclear Overhauser effect spectroscopy (NOESY) spectrum showed the correlations between proton at δ H 2.69 (H-9) and proton at δ H 2.13 (H-6β), and between two protons at δ H 3.14 (H-5) and at δ H 2.69 (H-9), confirming that the β-orientation of H-5 and H-9.…”

Section: Resultsmentioning

confidence: 95%

Three New Iridoid Glycosides from the Fruit of <i>Gardenia jasminoides</i> var. <i>radicans</i>

Qin¹,

Meng²,

Zou³

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Three new iridoid glycosides, 6″-O-trans-feruloylgenipin gentiobioside (1), 2′-O-trans-p-coumaroylgardoside (2), 2′-O-trans-feruloylgardoside (3), were isolated from the fruit of Gardenia jasminoides var. radicans MAKINO (Rubiaceae). The structures of these compounds were elucidated on the basis of MS, NMR spectra analysis, glycoside hydrolysis, and sugar derivatization coupled with HPLC analysis.

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“…Reference compounds of M1 to M18 (Figure 1) were isolated previously from ZYQL by author, structures of which were elucidated by comparison of spectral data (UV, MS, 1 H NMR, and 13 C NMR) with the literature data (Lin et al 2006;Okamurα et al 1998;Huang et al 2012;Zhang and Chen 1997;Ma et al 2009;Miyake et al 2007;Liu et al 2011;Chen et al 2008;Rayyan et al 2005;Kumarasamy et al 2004;Ke et al 1999;Yoo et al 2002;Dinda et al 2011;Esteban et al 1986;Ballester et al 2013;Wang et al 2010;Hòrie et al 1998). The purity of each reference standard was determined to be above 98% by HPLC analysis based on a peak area normalization method, detected by HPLC-PDA and confirmed by HR-ESI-TOF-MS and NMR spectroscopy.…”

Section: Chemicals and Materialsmentioning

confidence: 99%

Simultaneous quantification of major bioactive constituents from Zhuyeqing Liquor by HPLC-PDA

Gao

Wang

et al. 2014

J Anal Sci Technol

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Background: Zhuyeqing Liquor (ZYQL) is a famous traditional Chinese functional liquor. For quality control of ZYQL products, quantitative analysis using high-performance liquid chromatography coupled with photodiode array detector (HPLC-PDA) was undertaken. Methods: Eighteen compounds from ZYQL were simultaneously detected and used as chemical markers in the quantitative analysis, including 3-hydroxy-4, −4 and 64.90 × 10 −4 μg/μL for the different analytes. Furthermore, the optimum sample preparation was obtained from HPD 100 column eluted with water and 95% ethanol, respectively. Conclusions: Quality control of ZYQL products, in total seven samples and twelve parent plants, was examined by this method, and results confirmed its feasibility and reliability in practice.

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Naturally Occurring Iridoids and Secoiridoids. An Updated Review, Part 4

Cited by 132 publications

References 91 publications

Dual Function of the Cytochrome P450 CYP76 Family from Arabidopsis thaliana in the Metabolism of Monoterpenols and Phenylurea Herbicides

Dual Function of the Cytochrome P450 CYP76 Family from Arabidopsis thaliana in the Metabolism of Monoterpenols and Phenylurea Herbicides

Three New Iridoid Glycosides from the Fruit of <i>Gardenia jasminoides</i> var. <i>radicans</i>

Simultaneous quantification of major bioactive constituents from Zhuyeqing Liquor by HPLC-PDA

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