Benzodioxans by oxidative phenol coupling. Synthesis of silybin

Merlini, L.; Zanarotti, A.; Pelter, Andrew; Rochefort, Malcolm P.; Hänsel, Rudolf

doi:10.1039/p19800000775

Cited by 77 publications

(70 citation statements)

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“…Peroxidases also produce semiquinone as the primary products. Semiquinones possessing related structures have been shown to undergo radical coupling to generate similar benzodioxan dimeric products (Merlini et al, 1980). The radical coupling observed during the laccase reaction is quite surprising given the fact that similar free radicals only exhibit Fig.…”

Section: Resultsmentioning

confidence: 97%

Reexamination of the mechanisms of oxidative transformation of the insect cuticular sclerotizing precursor, 1,2-dehydro-N-acetyldopamine

Abebe

Zheng

Evans

et al. 2010

Insect Biochemistry and Molecular Biology

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Section: Resultsmentioning

confidence: 97%

Reexamination of the mechanisms of oxidative transformation of the insect cuticular sclerotizing precursor, 1,2-dehydro-N-acetyldopamine

Abebe

Zheng

Evans

et al. 2010

Insect Biochemistry and Molecular Biology

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“…There was further proof by NOE experiment; no NOE effect between the protons at H-2 and H-3 indicated both protons in trans-configuration. 14 From the above spectral data, compound 10 was identified with the proposed structure and named as origalignanol.…”

Section: Resultsmentioning

confidence: 99%

Benzolignanoid and Polyphenols from Origanum Vulgare

Lin

Wang

Shiao

et al. 2003

J Chinese Chemical Soc

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A new dihydrobenzodioxane derivative, origalignanol (10), together with nine polyphenolic compounds, salvianolic acid A (1), salvianolic acid C (2), lithospermic acid (3), apigenin (8), and luteolin 7-O-b-D-xylopyranoside (9), were isolated from the aqueous ethanolic extract of the aerial parts of Origanum vulgare for the first time. The structure of new compound 10 was determined on the basis of spectroscopic methods. Compound 5 is probably an artifact formed during the isolation. Compounds 1, 2 and 3 showed strong DPPH radical scavenging activity with an EC50 of 7.2 ± 0.4, 9.6 ± 0.9, and 9.5 ± 0.7 mM, respectively, and protected rat hepatocytes from CCl4-damage at 100 mM.

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“…64,65 It was revealed that the substituents on the catechol fragment (i.e. 28 in Scheme 3) have a strong effect on the regioselectivity of the reaction; electron donating substituents, like methyl as in 28, strongly favour the formation of 3-aryl products (e.g.…”

Section: Further Developments and Application Of Biomimetic Methodsmentioning

confidence: 99%