Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step

Hanamura, Shun; Hanaya, Kengo; Shoji, Mitsuru; Sugai, Takeshi

doi:10.1016/j.molcatb.2016.03.001

Cited by 20 publications

(12 citation statements)

References 29 publications

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“…Dehydrogenation [32] of 9 and subsequent acetylation provided peracetylated 15 a in 79 %y ield from 9.C ompound 15 a was transformed into 15 b in 69 %y ield by chemoselective removal of the phenolic acetates with sodium perborate [34] withouta ffecting the aliphatic or alicyclic acetyl protective groups. [23] Subsequent site-selective methylation at C-3' furnished 15 c in 82 %y ield. Diglycosylated 7 was obtained in 60 %y ield by removal of the remaininga cetate groups under mild conditions with triethylamine in methanol.…”

Section: Resultsmentioning

confidence: 99%

“…We are currently investigating site‐selective synthetic approaches to bioactive flavonoids from naturally abundant and easily available glycosylated forms . We therefore became interested in the derivatives 6 – 8 (Scheme ) in which the hydroxy group at C‐7 is capped with a mono‐, di‐ or triglycoside, respectively, rather than the methoxy group in 4 and 5 .…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 5‐Hydroxy‐3′,4′,7‐trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2‐Mediated Anticancer Drug Resistance

et al. 2018

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3',4',7-Trimethoxyflavone (TMF) has been reported to show a potent reversal effect on drug resistance mediated by breast cancer resistance protein (BCRP)/ATP-binding cassette subfamily G member 2 (ABCG2). In this study, we designed and synthesized five derivatives with either a hydroxy group or a fluorine atom at C-5 and several kinds of capping moiety at the C-7 hydroxy group, on the same 3',4'-dimethoxy-substituted flavone skeleton. We subsequently evaluated the efficacies of these compounds against BCRP-expressing human leukaemia K562/BCRP cells. Reversal of drug resistance was expressed as the concentration of compound causing a twofold reduction in drug sensitivity (RI ). Of the synthesized compounds, the reversal effect of 5-hydroxy-3',4',7-trimethoxyflavone (HTMF, RI 7.2 nm) towards 7-ethyl-10-hydroxycamptothecin (SN-38) was stronger than that of TMF (RI 18 nm). Fluoro-substituted 5-fluoro-3',4',7-trimethoxyflavone (FTMF, RI 25 nm) and monoglycosylated 7-(β-glucosyloxy)-5-hydroxy-3',4'-dimethoxyflavone (GOHDMF, 91 nm) also exhibited reversal effects, whereas the di- and triglycoside derivatives did not. TMF, HTMF and FTMF at 0.01-10 μm upregulated the K562/BCRP cellular accumulation of Hoechst 33342 nuclear staining dye. In addition, western blotting revealed that treatment of K562/BCRP cells with 0.1 μm TMF, HTMF or FTMT suppressed the expression of BCRP. HTMF showed the strongest inhibition of BCRP-mediated efflux and suppression of BCRP expression of the three effective synthesized flavones.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of 5‐Hydroxy‐3′,4′,7‐trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2‐Mediated Anticancer Drug Resistance

et al. 2018

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“…For the synthesis of 2a, we recently reported the preparation of a related hydroxylation precursor 4e by the acetylation of piceid (4a) and the subsequent lipase-catalyzed site-selective deacetylation of 4d (Scheme 4). 40,41) Our first attempt, the oxidation of 4e with IBX in DMSO at room temperature 39) only resulted in the complex mixture. By the change of solvent to DMF under low temperature, the oxidation proceeded smoothly.…”

Section: Resultsmentioning

confidence: 99%

Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

Yamashita

Biard

Hanaya

et al. 2017

Bioscience, Biotechnology, and Biochemistry

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“…Such a property of lipases is of tremendous importance to chemical and pharmaceutical industries especially in the production of isomeric compounds that exhibit optimal function only under specific configuration. Some of the recent findings of regioselective lipases include acylation of quercetin with ferulic acid using Rhizopus (R.) oryzae lipase to synthesize flavonoid derivatives, deprotection process of per‐O‐acetylated thymidine, producing the 3′‐OH‐5′‐OAc‐thymidine using lipase from C. rugosa, synthesis of acacetin and resveratrol 3,5‐di‐O‐beta‐glucopyranoside using C. antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS‐IM), etc. The regioselective lipases can be further classified based on their selective functionality as follows:…”

Section: Lipase Structure and Classificationmentioning

confidence: 99%

Recent advances on sources and industrial applications of lipases

Sarmah

Revathi

Sheelu

et al. 2017

Biotechnology Progress

302

148

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Lipases are the industrially important biocatalysts, which are envisioned to have tremendous applications in the manufacture of a wide range of products. Their unique properties such as better stability, selectivity and substrate specificity position them as the most expansively used industrial enzymes. The research on production and applications of lipases is ever growing and there exists a need to have a latest review on the research findings of lipases. The present review aims at giving the latest and broadest overall picture of research and development on lipases by including the current studies and progressions not only in the diverse industrial application fields of lipases, but also with regard to its structure, classification and sources. Also, a special emphasis has been made on the aspects such as process optimization, modeling, and design that are very critical for further scale-up and industrial implementation. The detailed tabulations provided in each section, which are prepared by the exhaustive review of current literature covering the various aspects of lipase including its production and applications along with example case studies, will serve as the comprehensive source of current advancements in lipase research. This review will be very useful for the researchers from both industry as well as academia in promoting lipolysis as the most promising approaches to intensified, greener and sustainable processes. © 2017 American Institute of Chemical Engineers Biotechnol. Prog., 34:5-28, 2018.

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Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step

Cited by 20 publications

References 29 publications

Synthesis of 5‐Hydroxy‐3′,4′,7‐trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2‐Mediated Anticancer Drug Resistance

Synthesis of 5‐Hydroxy‐3′,4′,7‐trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2‐Mediated Anticancer Drug Resistance

Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

Recent advances on sources and industrial applications of lipases

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