Phenolic glucosides from Parabenzoin praecox

Shimomura, Hiroko; Sashida, Yutaka; Oohara, Motomu; Tenma, Hiroko

doi:10.1016/0031-9422(88)83166-2

Cited by 47 publications

(21 citation statements)

References 5 publications

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“…IR Spectra (KBr) were recorded on a Bio-Rad FTS-135 spectrophotometer; in cm ÀC6'')); 4.37 (t, J 6.9, HÀC(3'')); 4.35 (t, J 6.5, HÀC(2'')); 4.27 (t, J 6.6, HÀC(4'')); 4.23 ± 4.27 (m, HÀC(5'')); 3.76 (s, 2 MeO). [9]; and 3 gave 3,4,5-trimethoxyphenol [11].…”

Section: Experimental Partmentioning

confidence: 99%

New Antioxidant Phenolic Glycosides from Walsura yunnanensis

Luo

Cai

et al. 2006

Chemistry & Biodiversity

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Four new polyphenolic glycosides (1-4) were isolated from the BuOH extract of the bark of Walsura yunnanenis C. Y. Wu. These compounds comprise two lignans, i.e., the 9-O-alpha-L-arabinopyranosides 1 and 2 of (-)-isolariciresinol and of (+)-5-methoxyisolariciresinol, respectively, and the two phenolic glycosides 3,4,5-trimethoxyphenyl 2-O-(alpha-L-fucopyranosyl)-beta-D-glucopyranoside (3) and 3,5-dihydroxyphenyl 6-O-(4-hydroxy-3,5-dimethoxybenzoyl)-beta-D-glucopyranoside (walsuraside; 4). In addition, three known compounds, 3,4,5-trimethoxyphenyl beta-D-glucopyranoside, asperglaucide, and butyl alpha-D-fructofuranoside were identified. Their structures were elucidated spectroscopically and by chemical transformation (hydrolysis). The new compounds 1, 2, and 4 displayed significant antioxidant activities, with IC(50) values in the range of ca. 42 to 49 microg/ml.

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Section: Experimental Partmentioning

confidence: 99%

New Antioxidant Phenolic Glycosides from Walsura yunnanensis

Luo

Cai

et al. 2006

Chemistry & Biodiversity

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“…17) Compounds 15 and 16 were identified as the oleanane-type triterpenes maslinic acid (15) 17) and erythrodiol (16). 19) Compounds 17-22 were identified as aromatic and flavonoid derivatives; 1-b-D-glucopyranosyloxy-3,4,5-trimethoxybenzene (17), 20) avicularin (18), 21) …”

Section: Antitumor-promoting Constituents Frommentioning

confidence: 99%

Antitumor-Promoting Constituents from Chaenomeles sinensis KOEHNE and Their Activities in JB6 Mouse Epidermal Cells

Gao

Kuroyanagi

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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Primary screening of antitumor-promoting activity using soft agar colony assays with JB6 cells was employed to isolate 22 compounds from Chaenomeles sinensis KOEHNE. These compounds were lyoniresinol-2a-O-a a- Compound 1, having a rhamnosyl group, showed greater activity than 2, having a glucosyl group, and 3, which was a bis-demethoxy derivative of 1. Betulinic acid (4), having a C-28 carboxyl group, 3-O-(E )-caffeoylbetulin (7), and tormentic acid (12) showed more potent activity than betulin (5), which has a C-28 hydroxymethyl group.

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“…Ther first characterization of glucoside 1a as 1-O-b-D-glucopyranosyl anthranilate and 2a as 3,4-dimethoxyphenyl b-D-glucopyranoside has been published elsewhere [3,4] [12] except for the d of H29 and H49 which in our case were 5.25 (1H, dd, J = 9.5, 7.6) and 5.16 (1H, dd, J = 9.6, 9.6), respectively. Furthermore, the coupling constants for H6a9 and H6b9 were interchanged in the paper published by Shimomura et al [12]. After deacetylation and enzymatic hydrolysis (Rohapect D5L) the liberated aglycon was identified by capillary GC and capillary GC-MS as 3,4,5-trimethoxyphenol.…”

Section: Isolation Of Glucoconjugatesmentioning

confidence: 94%

“…Previously it was isolated from the bark of Parabenzoin praecox [12], in contrast, (6S,9R)-vomifolyl b-D-glucopyranoside is an ubiquitous natural compound that has been detected in various fruit species [13]. Finally, it is important to note that glucosides 3 and 4 after enzymatic degradation with a glucosidase produced 3,4,5-trimethoxyphenol and vomifoliol, respectively important volatiles in flavor industry.…”

Section: Isolation Of Glucoconjugatesmentioning

confidence: 96%