Synthesis of Optically Active Vomifoliol and Roseoside Stereoisomers

Yamano, Yumiko; Ito, Masayoshi

doi:10.1248/cpb.53.541

Cited by 101 publications

(65 citation statements)

References 19 publications

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“…Eight compounds were isolated from the chloroform layer. Compounds 4-30 were identified by detailed comparisons of their spectroscopic data with those in the literature as kaempferol (4), 13) 16) tiliroside (8), 3) quercetin (9), 17) rutin (10), 18) 24) isorhamnetin 3-O-β-d-glucopyranoside (17), 15) gallic acid (18), 25) methyl gallate (19), 26) 4-hydroxybenzoic acid (20), 27) protocatechuic acid (21), 28) methyl brevifolincarboxylate (22), 29) ursolic acid (23), 30) ursolic aldehyde (24), 31) 28-nor-urs-12-ene-3β,17β-diol (25), 32) pomolic acid (26), 33) 2α-hydroxy ursolic acid (27), 33) 23-hydroxy ursolic acid (28), 34) vomifoliol (29), 35) and β-sitosterol (30) 30) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Inhibitory Effects of the Constituents of <i>Hippophae rhamnoides</i> on 3T3-L1 Cell Differentiation and Nitric Oxide Production in RAW264.7 Cells

Yang

Wen

et al. 2013

Chem. Pharm. Bull.

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Three new flavonol glycosides, hippophaeosides A-C (1-3), together with 27 known constituents, were isolated from Hippophae rhamnoides L. leaves. Their structures were determined by spectroscopic analyses. Their inhibitory activities on 3T3-L1 preadipocyte differentiation and triglyceride accumulation in maturing adipocytes, and nitric oxide production in RAW264.7 cells were examined.Key words Hippophae rhamnoides; flavonol glycoside; triterpenoid; adipocyte; macrophage Hippophae rhamnoides L. (Elaeagnaceae), known as "sea buckthorn," is a deciduous shrub distributed throughout Asia and Europe. The fruit has been used as a traditional medicine for the treatment of cough indigestion and blood stasis in China.1) Investigations of H. rhamnoides have yielded flavonols, 2-4) triterpenoids, 5,6) and tannins.3) The leaf has been reported to have anti-inflammatory, 7) antioxidant, 4) anti-obesity, 8,9) and α-glucosidase inhibitory activities. 4)In our previous study, we investigated anti-obesity and antiinflammatory compounds that not only inhibit triglyceride (TG) accumulation by 3T3-L1 adipocytes but also inhibit the secretion of nitric oxide (NO) from RAW264.7 cells. In that study, several crude drugs were examined. [10][11][12] In the present study, the 80% methanol extract of the leaves of H. rhamnoides L. and the chloroform-and ethyl acetatesoluble portions of the extract were observed to inhibit the TG accumulation in 3T3-L1 cells, and inhibit NO production in lipopolysaccharide (LPS) and interferon-γ (IFN-γ) activated macrophages. Furthermore, an attempt to identify the bioactive compounds present in this plant led to the isolation of three new flavonol glycosides, Hippophaeosides A (1), B (2), and C (3), along with 27 known constituents. Results and DiscussionThe leaves of H. rhamnoides L. were extracted with 80% aqueous methanol, followed by evaporation of the solvent under reduced pressure from the combined extract to give the 80% methanol extract. The extract [TG and NO inhibitory activity: 35% and 63%, respectively (30 µg/mL) [42, 15% (30 µg/mL)]. We focused our efforts on investigating the chemical constituents of the chloroform-and ethyl acetate-soluble fractions. The ethyl acetate layer was separated by Sephadex LH-20 column chromatography to yield four fractions from which 22 compounds including three new compounds 1-3 were isolated. Eight compounds were isolated from the chloroform layer. Compounds 4-30 were identified by detailed comparisons of their

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Section: Resultsmentioning

confidence: 99%

Inhibitory Effects of the Constituents of <i>Hippophae rhamnoides</i> on 3T3-L1 Cell Differentiation and Nitric Oxide Production in RAW264.7 Cells

Yang

Wen

et al. 2013

Chem. Pharm. Bull.

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“…Among them, cleomiscosin C, luteoline, quercetine, and thevetiaflavone were isolated for the first time from the Brucea plants. The NMR spectroscopic data of compounds 3 and 4 were identical with those of cucumegastigmane I and vomifoliol, respectively [7] (7) and HÀC(8) [7] [8]. However, the absolute configuration of C(9) was not determined due to limited sample quantity, though in principle it could be determined by a modified Moshers method [7].…”

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confidence: 77%

“…In addition, ten known compounds including (6S,7E)-6,9,10-trihydroxymegastigma-4,7-dien-3-one (3) [7] and (6S,7E)-6,9-dihydroxymegastigma-4,7-dien-3-one (4) [8] (megastigmane ¼ 2-butyl-1,1,3-trimethylcyclohexane), cleomiscosin A [9 -11], cleo- Table 2.…”

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Bruceines K and L from the Ripe Fruits of Brucea javanica

Zhao

Lau

et al. 2011

Helvetica Chimica Acta

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Bruceine K (1), a pentacyclic C 20 -quassinoid bearing a unique 12,20-epoxy moiety, and bruceine L (2), along with the ten known compounds (6S,7E)-6,9,10-trihydroxy-and (6S,7E)-6,9-dihydroxymegastigma-4,7-dien-3-one (3 and 4, resp.), cleomiscosins A -C, luteoline, quercetine, bruceantinol, pinoresinol, and thevetiaflavone, were isolated from the ripe fruits of Brucea javanica. Bruceines K (1) and L (2) were determined to be (1b,2a,11b,12b,14x,15b)-12,20-epoxy-1,2,11,13,14,15-hexahydroxypicras-3-en-16-one and (1b,2a,11b,12b,15b)-13,20-epoxy-1,2,11,12-tetrahydroxy-16-oxo-15-(senecioyloxy)-picras-3-en-21-oic acid methyl ester (senecioic acid ¼ 3-methylbut-2-enoic acid), respectively, on the basis of NMR ( 1 H-and 13 C-NMR, DEPT, 1 H, 1 H-COSY, NOESY, HMQC, and HMBC) and ESI-MS data. Among the known compounds, (6S,7E)-6,9,10-trihydroxy-and (6S,7E)-6,9-dihydroxymegastigma-4,7-dien-3-one (3 and 4, resp.), cleomiscosin C, luteoline, quercetine, and thevetiaflavone were isolated for the first time from the Brucea plants.Introduction. -The dried ripe fruits of Brucea javanica (L.) Merr. (Simaroubaceae), known as Bruceae Fructus (Ya-Dan-Zi in Chinese), has been used for the treatment of dysenteric disorders, malaria, and tumors in Chinese medicine and is known to be a rich source of quassinoids [1]. In a previous study, an 80% EtOH extract displayed significant cytotoxicity in three pancreatic-cancer cell lines (PANC-1, SW1990, and CAPAN-1) with IC 50 values ranging from 1.5 to 5 mg/ml, while it exerted minimal cytotoxic action on Hs68 cells, a line of normal foreskin fibroblasts, with an IC 50 value larger than 100 mg/ml [2]. A bioassay-guided isolation led to the separation of bruceine K (1), a new pentacyclic C 20 quassinoid bearing a unique 12,20-epoxy bridge, and bruceine L (2), a new naturally occurring quassinoid, from the AcOEtsoluble fraction of the ripe fruits of Brucea javanica. This article reports the detailed structural elucidation of compounds 1 and 2 (Fig. 1).

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“…1, 2) from an 80% acetone extract of the plant. Known compounds were identified from spectroscopic data as 3′-O-methyl-rosmarinic acid (14), 5) isovitexin (19), 6) vicenin-2 (20), 7) (21), 8) (Z)-3-hexenyl β-D-glucopyranoside (23), 9) perilloside E (25), 10) benzyl β-Dglucopyranoside (26), 11) (6S,9S)-roseoside (27), 12) (−)-(1R,2R)-5′-β-D-glucopyranosyloxyjasmonic acid (28), 13) and (3R)-O-β-D-glucopyranosyloxy-5-phenylvaleric acid (29). 14) Other known compounds were directly compared with those isolated previously and identified as caffeic acid (11), 15) clinopodic acid A (12), 16) rosmarinic acid (13), 16) luteolin (15), 15) chrysoeriol (16), 15) apigenin 7-O-β-D-glucuronopyranoside (17), 3) acacenin Regular Article * To whom correspondence should be addressed.…”

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confidence: 99%