Constitutive Accumulation of 
            cis
            -piceid in Transgenic Arabidopsis Overexpressing a Sorghum Stilbene Synthase Gene

Yu, Christine K.Y.; Lam, Corey N. W.; Springob, Karin; Schmidt, J.; Chu, Ivan K.; Lo, Clive

doi:10.1093/pcp/pcj061

Cited by 49 publications

(53 citation statements)

References 15 publications

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“…5) was similar to that of compound 1, implying that 2 has the same 7S, 8S, 7ЉR, 8ЉS absolute configuration. Furthermore, 1 can be converted to 2 under UV irradiation, similar to other oligostilbenes, [16][17][18] and trans-e-viniferin (4) can also be converted to cis-e-viniferin (5) with UV irradiation in 2H, s)]. In addition, the CD spectrum of compound 7 was similar to that of compound 6 (Fig.…”

mentioning

confidence: 74%

Three New Oligostilbenes from the Seeds of Paeonia suffruticosa

Peng

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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NotePaeonia suffruticosa ANDR. (Paeoniaceae) is found extensively in China. It is an important Chinese medicinal plant from the section Moutan of the genus Paeonia. This genus consists of ca. 35 species placed in three sections: Moutan, Oneapia, and Paeonia.1) The root cortex of this plant (Chinese name: mudanpi) is a well-known Chinese herbal medicine widely used as an analgesic, anaphylactic, antioxidative, and antiinflammatory agent. Numerous studies on the chemistry and pharmacology of this species have been performed.2) Previous phytochemical studies indicated that stilbenes were the primary bioactivity constituents of peony seeds. These stilbenes exhibit potent biological activities such as cytotoxic, antimutagenic, ecdysteroid antagonist, antioxidant, hyperpigmentation, antitumor, and anti-inflammatory activity and can improve bone disease. [3][4][5][6][7][8] In the course of searching for new bioactive natural products from the seeds of this plant, 11 stilbenes, trans-(1) and cis-suffruticosol D (2), trans-resveratrol (3), 9) trans-e-viniferin (4), 7)cis-e-viniferin (5), 7) gnetin H (6), 7) cis-gnetin H (7), suffruticosol A (8),3) suffruticosol B (9), 3) suffruticosol C (10), 3) and cis-ampelopsin E (11), 10) were isolated from the ethyl acetate extract of the seeds of P. suffruticosa. Among them, 1, 2, and 7 were new compounds. Here, we report the isolation and extensive structural elucidation of the new compounds. Results and Discussiontrans-Suffruticosol D (1) Three new oligostilbenes, trans-suffruticosol D (1), cis-suffruticosol D (2), and cis-gnetin H (7), were isolated along with the eight known stilbenes, trans-resveratrol (3), trans-e e-viniferin (4), cis-e e-viniferin (5), gnetin H (6), suffruticosol A (8), suffruticosol B (9), suffruticosol C (10), and cis-ampelopsin E (11) from the seeds of Paeonia suffruticosa. Compounds 3-6 were isolated for the first time from this plant species, and compound 11 was isolated for the first time from the genus Paeonia. The structures of the new compounds were elucidated based on spectral analyses, including 1D and 2D NMR experiments. The absolute configuration of compound 1 was determined by quantum chemical calculation of the electronic circular dichroism and comparison with the experimental circular dichroism spectrum.

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confidence: 74%

Three New Oligostilbenes from the Seeds of Paeonia suffruticosa

Peng

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…To preserve the structures of 2-hydroxyflavanone derivatives, plant samples (10-d-old seedlings extracted in methanol) were analyzed directly by HPLC-MS/MS without acid treatments. Since heterologously expressed phenolics are usually O-glycosylated in Arabidopsis (Yu et al, 2005(Yu et al, , 2006, we performed precursor ion scan analyses to search for 2-hydroxyflavanone O-glycosides in the nonhydrolyzed extracts. During MS/MS experiments, fragmentations by the loss of sugar moiety are easily induced due to the labile nature of the O-glycosidic linkages.…”

Section: Transgenic Arabidopsis Overexpressing Cyp93g2 or Coexpressinmentioning

confidence: 99%

“…The flow rate was maintained at 0.2 mL min 21 , and the elution was monitored by a diode-array detector (200-600 nm) in tandem with an API2000-QTRAP mass spectrometer (Applied Biosystems). Enhanced full-scan, product ion scan, precursor ion scan, and MS 3 spectra were acquired as described previously (Yu et al, 2006;Shih et al, 2008). Quantification of tricin and isovitexin was achieved by multiple-reaction monitoring using the transition reactions m/z 331.2 / 315.3 and m/z 433.3 / 283.3, respectively.…”

Section: Hplc-ms/ms Analysis Of Enzyme Reaction Products and Plant Mementioning

confidence: 99%

CYP93G2 Is a Flavanone 2-Hydroxylase Required for C-Glycosylflavone Biosynthesis in Rice

et al. 2010

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C-Glycosylflavones are ubiquitous in the plant kingdom, and many of them have beneficial effects on human health. They are a special group of flavonoid glycosides in which the sugars are C-linked to the flavone skeleton. It has been long presumed that C-glycosylflavones have a different biosynthetic origin from O-glycosylflavonoids. In rice (Oryza sativa), a C-glucosyltransferase (OsCGT) that accepts 2-hydroxyflavanone substrates and a dehydratase activity that selectively converts C-glucosyl-2-hydroxyflavanones to 6C-glucosylflavones were recently described. In this study, we provide in vitro and in planta evidence that the rice P450 CYP93G2 protein encoded by Os06g01250 is a functional flavanone 2-hydroxylase. CYP93G2 is related to the CYP93B subfamily, which consists of dicot flavone synthase II enzymes. In the presence of NADPH, recombinant CYP93G2 converts naringenin and eriodictyol to the corresponding 2-hydroxyflavanones. In addition, CYP93G2 generates 2-hydroxyflavanones, which are modified by O-glycosylation in transgenic Arabidopsis (Arabidopsis thaliana). Coexpression of CYP93G2 and OsCGT in Arabidopsis resulted in the production of C-glucosyl-2-hydroxyflavanones in the dibenzoylmethane tautomeric form. The same structure was reported previously for the in vitro OsCGT reaction products. Thus, CYP93G2 generates 2-hydroxyflavanone substrates from flavanones for C-glucosylation by OsCGT in planta. Furthermore, knocking down Os06g01250 in rice (O. sativa subsp. japonica 'Zhonghua 11') preferentially depleted the accumulation of C-glycosylapigenin, C-glycosylluteolin, and C-glycosylchrysoeriol but did not affect the levels of tricin, which is frequently present as O-glycosides in cereals. Taken together, our work conclusively assigned CYP93G2 as the first enzyme that channels flavanones to C-glycosylflavone biosynthesis in rice.

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“…In consequence, the ability to synthesize stilbenes can be conferred to many plant species by expressing an STS gene (Hain et al, 1990;Hipskind and Paiva, 2000;Yu et al, 2006). In this work, we used tobacco leaves capable of stilbene biosynthesis due to the transient expression of the grapevine STS VST1 cDNA to characterize the activity of ROMT in planta.…”

Section: Pterostilbene Accumulates As the Major Stilbene Following Inmentioning

confidence: 99%

A Stress-Inducible Resveratrol O-Methyltransferase Involved in the Biosynthesis of Pterostilbene in Grapevine

et al. 2008

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Stilbenes are considered the most important phytoalexin group in grapevine (Vitis vinifera) and they are known to contribute to the protection against various pathogens. The main stilbenes in grapevine are resveratrol and its derivatives and, among these, pterostilbene has recently attracted much attention due both to its antifungal and pharmacological properties. Indeed, pterostilbene is 5 to 10 times more fungitoxic than resveratrol in vitro and recent studies have shown that pterostilbene exhibits anticancer, hypolipidemic, and antidiabetic properties. A candidate gene approach was used to identify a grapevine resveratrol O-methyltransferase (ROMT) cDNA and the activity of the corresponding protein was characterized after expression in Escherichia coli. Transient coexpression of ROMT and grapevine stilbene synthase in tobacco (Nicotiana benthamiana) using the agroinfiltration technique resulted in the accumulation of pterostilbene in tobacco tissues. Taken together, these results showed that ROMT was able to catalyze the biosynthesis of pterostilbene from resveratrol both in vitro and in planta. ROMT gene expression in grapevine leaves was induced by different stresses, including downy mildew (Plasmopara viticola) infection, ultraviolet light, and AlCl 3 treatment.

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Constitutive Accumulation of cis -piceid in Transgenic Arabidopsis Overexpressing a Sorghum Stilbene Synthase Gene

Cited by 49 publications

References 15 publications

Three New Oligostilbenes from the Seeds of Paeonia suffruticosa

Three New Oligostilbenes from the Seeds of Paeonia suffruticosa

CYP93G2 Is a Flavanone 2-Hydroxylase Required for C-Glycosylflavone Biosynthesis in Rice

A Stress-Inducible Resveratrol O-Methyltransferase Involved in the Biosynthesis of Pterostilbene in Grapevine

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