Biosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units

De-Eknamkul, Wanchai; Potduang, Buppachart

doi:10.1016/s0031-9422(02)00555-1

Cited by 136 publications

(82 citation statements)

References 16 publications

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“…Although phytosterols are usually considered to be exclusively MVA derived, an equal contribution of the MVA and MEP pathways to their biosynthesis already has been reported in Croton sublyratus callus culture (De-Eknamkul and Potduang, 2003). While the relative contribution of the MEP and MVA pathways to phytosterol biosynthesis could not be quantitated, it was clear that osmotic stress enhanced the MEP pathway input.…”

Section: Dolmentioning

confidence: 95%

Modeling of Dolichol Mass Spectra Isotopic Envelopes as a Tool to Monitor Isoprenoid Biosynthesis

et al. 2017

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The cooperation of the mevalonate (MVA) and methylerythritol phosphate (MEP) pathways, operating in parallel in plants to generate isoprenoid precursors, has been studied extensively. Elucidation of the isoprenoid metabolic pathways is indispensable for the rational design of plant and microbial systems for the production of industrially valuable terpenoids. Here, we describe a new method, based on numerical modeling of mass spectra of metabolically labeled dolichols (Dols), designed to quantitatively follow the cooperation of MVA and MEP reprogrammed upon osmotic stress (sorbitol treatment) in Arabidopsis (Arabidopsis thaliana). The contribution of the MEP pathway increased significantly (reaching 100%) exclusively for the dominating Dols, while for long-chain Dols, the relative input of the MEP and MVA pathways remained unchanged, suggesting divergent sites of synthesis for dominating and long-chain Dols. The analysis of numerically modeled Dol mass spectra is a novel method to follow modulation of the concomitant activity of isoprenoid-generating pathways in plant cells; additionally, it suggests an exchange of isoprenoid intermediates between plastids and peroxisomes.Isopentenyl diphosphate (IPP), the building block of isoprenoids, the most numerous class of secondary metabolites, is derived in plants from two pathways operating in parallel: the cytoplasmic mevalonate (MVA) and the plastidic methylerythritol phosphate (MEP) pathways (Rohmer, 1999;Pulido et al., 2012).Analysis of over 130 isoprenoids has shown that, in angiosperms under standard growth conditions, carotenoids and chlorophyll phytyl chains on the one hand and phytosterols on the other are made nearly exclusively via a single pathway (MEP and MVA, respectively), while numerous other isoprenoids, including dolichols (Dols; Skorupinska-Tudek et al., 2008), are of mixed origin (Hemmerlin et al., 2012).The cooperation of the two pathways (often called cross talk) is considered essential for plant adaptive responses to biotic and abiotic stresses. Consequently, their relative contributions to the formation of IPP are modulated, and the expression of particular genes of the MVA and MEP pathways is frequently correlated with stress (pathogen attack, elicitation, wounding, etc.;Hemmerlin et al., 2012) or plant development (Opitz et al., 2014). Interestingly, the effect of stress on the regulation of the MEP-MVA balance has so far been analyzed only qualitatively.Several methodologies have been employed to unravel the relative contributions of the MVA and MEP pathways to isoprenoids, such as metabolic labeling with isotopically labeled precursors (stable isotopes or radioisotopes were used), followed by structural analysis of the product of interest or blockage of the pathway (chemical, with pathway-specific inhibitors, or genetic), followed by quantification of the isoprenoid intermediates and/or end products. The advantages

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Section: Dolmentioning

confidence: 95%

Modeling of Dolichol Mass Spectra Isotopic Envelopes as a Tool to Monitor Isoprenoid Biosynthesis

et al. 2017

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“…The isolated compound was identified as SMR by comparison with the mass spectrum and NMR spectra with the published reference data [19]. SMR: white amorphous powder; 1 H NMR (CDCl 3 , 600 MHz): δ H 0.67 (3H, s, H-18), 0.78 (3H, s, H-27), 0.79 (3H, s, H-19), 0.81 (3H, s, H-29), 0.82 (3H, s, H-26), 1.02 (3H, brs, H-21), 3.36 (1H, m, H-3α), 5.12 (1H, dd, J = 15.4, 8.4, H-22), 5.33 (1H, d, J = 4.7 Hz, H-6); 13 C NMR (CDCl 3 , 150 MHz): δ C 37.3 (C-1), 31.8 (C-2), 71.8 (C-3), 41.3 (C-4), 140.7 (C-5), 121.7 (C-6), 31.8 (C-7), 31.9 (C-8), 50.2 (C-9), 36.6 (C-10), 21.2 (C-11), 39.8 (C-12), 42.3 (C-13), 56.9 (C-14), 24.3 (C-15), 29.1 (C-16), 56.1 (C-17), 11.9 (C-18), 19.4 (C-19), 40.5 (C-20), 21.1 (C-21), 138.3 (C-22), 129.2 (C-23), 51.2 (C-24), 31.7 (C-25), 19.0 (C-26), 21.2 (C-27), 25.4 (C-28), 12.0 (C-29); EIMS: 412 M + .…”

Section: Methodsmentioning

confidence: 99%

Anti-diabetic activity of stigmasterol from soybean oil by targeting the GLUT4 glucose transporter

Wang

Yang

et al. 2017

Food & Nutrition Research

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The present study investigated the anti-diabetic activity and potential mechanism of stigmasterol (SMR), which is a kind of phytosterols derived from the edible soybean oil in vitro and in vivo. SMR displayed a mild GLUT4 translocation activity by 1.44-fold in L6 cells. L6 cells were treated with different concentration of SMR, showing significant effects on the enhancing glucose uptake. SMR administrated orally to the KK-Ay mice significantly alleviated their insulin resistance and oral glucose tolerance with reducing fasting blood-glucose levels and blood lipid indexes such as triglyceride and cholesterol. Moreover, the GLUT4 expression in L6 cells, skeletal muscle and white adipose tissue had been also enhanced. In this paper we conclude that, stigmasterol seems to have potential beneficial effects on the treatment of type 2 diabetes mellitus with the probable mechanism of targeting GLUT4 glucose transporter included increasing GLUT4 translocation and expression.

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“…albida yielded one new iridoid glucoside, 6′-O-Ecaffeoyl-mussaenosidic acid 1 , the iridoid glucoside 6′-O-Ecaffeoylcatalpol 14 , one known iridoid aglycon, rehmaglutin 15 and one known flavonoid, 4′-hydroxywogonin-7-O-β-D-glucuronic acid glycoside 16 . Also, the acetonic extract, offered four known triterpenes, stigmasterol 17 , β-sitosterol 18,19 , betulin 20 , and betulinic acid 20,21 . The plant material has been extracted as previously described 2 .…”

Section: Extraction and Isolationmentioning

confidence: 99%

Minor iridoids from Scutellaria albida ssp. albida. Inhibitory potencies on lipoxygenase, linoleic acid lipid peroxidation and antioxidant activity of iridoids from Scutellaria sp.

Gousiadou

Gotfredsen

Matsa

et al. 2012

Journal of Enzyme Inhibition and Medicinal Chemistry

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Biosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units

Cited by 136 publications

References 16 publications

Modeling of Dolichol Mass Spectra Isotopic Envelopes as a Tool to Monitor Isoprenoid Biosynthesis

Modeling of Dolichol Mass Spectra Isotopic Envelopes as a Tool to Monitor Isoprenoid Biosynthesis

Anti-diabetic activity of stigmasterol from soybean oil by targeting the GLUT4 glucose transporter

Minor iridoids from Scutellaria albida ssp. albida. Inhibitory potencies on lipoxygenase, linoleic acid lipid peroxidation and antioxidant activity of iridoids from Scutellaria sp.

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