Seven aromatic compounds from bark of Cinnamomum cassia

Miyamura, Mitsuhiko; Nohara, Toshihiro; Tomimatsu, Toshiaki; Nishiokat, Itsuo

doi:10.1016/s0031-9422(00)80092-8

Cited by 86 publications

(49 citation statements)

References 19 publications

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“…Tables 1 and 2) indicated the presence of three fragments, including a lyoniresinol [5] and a syringoyl group (d(H) 7.26 (s, HÀC(2''',6''')), 3.76 (s, MeOÀC(3'''), MeOÀC(5''')); d(C) 168.4 (C(7''')), 118.6 (C(1''')), 56.7 (MeOÀC(3'''), MeOÀC(5'''))), and a glucopyranose unit. Acid hydrolysis of 1 and chromatographic purification afforded d-glucose and (þ)-lyoniresinol, which were detected by TLC.…”

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“…These were compared with authentic samples of d-glucose and (À)-lyoniresinol (10), and the configurations were determined by measurement of the optical rotations. The b-anomeric configuration for the glucose was deduced from its large [5], the downfield shift of C(6'') in the glucopyranose unit from d(C) 62.9 to 65.0 established the attachment of the syringoyl group at C(6''). The assumption was confirmed by an HMBC correlation of HÀC(6'') (d(H) 4.58 and 4.34, each 1 H) to the ester C(7''')¼O group (d(C) 168.4) of the syringoyl group (Fig.…”

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confidence: 99%

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Tarennanosides A–H, Eight New Lignan Glucosides from Tarenna attenuata and Their Protective Effect on H₂O₂‐Induced Impairment in PC12 Cells

Yang

et al. 2009

Chemistry & Biodiversity

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Eight new lignan glucosides, tarennanosides A-H (1-8, resp.), were isolated from the whole plant of Tarenna attenuata, together with three known compounds, fernandoside, (-)-lyoniresinol, and (-)-isolariciresinol. The planar structures of new compounds were elucidated mainly by analysis of physical and spectroscopic data, and the absolute configurations were determined by acid hydrolysis as well as CD spectroscopy. Compounds 1 and 2 exhibited potent antioxidant activities against H2O2-induced impairment in PC12 cells. Preliminary mechanism study by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) method showed that these two compounds could act as radical scavengers.

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Tarennanosides A–H, Eight New Lignan Glucosides from Tarenna attenuata and Their Protective Effect on H₂O₂‐Induced Impairment in PC12 Cells

Yang

et al. 2009

Chemistry & Biodiversity

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“…All these data were consistent with those reported in the literature. 20 The anomalous chemical shifts of the methoxyl group at C-3 in compound 1 (δ 3.37) and the acetate analogous 1a (δ 3.18) suggest that this group may be shielded by the phenyl group at C-7'.…”

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Isolation and antitrichomonal activity of the chemical constituents of the leaves of Maytenus phyllanthoides Benth. (Celastraceae)

et al. 2014

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Cyclolignan (+)-lyoniresinol (1), veratric acid (2), vanillic acid (3), lupeol, oleanolic acid, 3β-hydroxy-urs-11-en-28,13β-lactone (4), the mixture of α-and β-amyrin, trans-polyisoprene, and β-sitosterol were isolated from the leaves of Maytenus phyllanthoides. The structures of the isolated compounds were established based on spectroscopic data, mainly 1 H and 13 C nuclear magnetic resonance (NMR). Compound 1, its acetate analog 1a, and compounds 2, 3, and 4 were tested against Trichomonas vaginalis. (+)-Lyoniresinol showed activity corresponding to IC 50 17.57 µM. This is the first report on the occurrence of 3β-hydroxy-urs-11-en-28,13β-lactone (4) in the Celastraceous family and lyoniresinol in the Maytenus genus, and on the antitrichomonal activity of lyoniresinol.

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“…Thus, compound 1 was determined as a derivative of lyoniresinol. 8,9) In the HMBC experiment of 1, the correlations were obtained between H-9Ј (d H 13,14) it is suggested that compound 4 was a racemic mixture of (7ЈS,8ЈR,8R)-lyoniresinol and (7ЈR,8ЈS,8S)-lyoniresinol; the former enantiomer was dominant. Owing to the aglycone of compounds 1, 4 came from the same plant, the configuration should not change.…”

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Rhusemialins A-C, New Cyclolignan Esters from the Roots of Rhus javanica var. roxburghiana

Ouyang

Wein

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Rhus javanica is one of five Rhus species (Anacardiaceae), distributing in the island of Taiwan. In the early days, the pericarp of R. semialata had been commonly used a substitute of salt by indigenous mountain people. The roots of it also do a folk herb for treating diarrhea, spermatorrhea and malaria.1) Early investigation in Rhus was only the plants of R. semialata and R. succedanea. Flavones, triterpenes, aromatics, tannins were isolated from them.2-8) This paper describes the isolation and structural elucidation of new cyclolignan esters (1), (2) and (3), and sever known compounds: lynoiresinol (4), [9][10][11] isolariciresinol, 12) methyl ferulate, vanillin, 4-hydroxy-3,5-dimethoxybenaldehyde, 4-methoxygallic acid, and gallic acid. They were isolated from the n-butanol extract of R. javanicaThe n-butanol fraction of methanol extract was fractionated by a combination of silica gel, Sephadex LH-20, and RP-18 columns to yield ten compounds, their structures were elucidated by 1D and 2D NMR spectra and comparison with literature data.Compound 1 was isolated a colorless powder. Its molecular formula C 31 H 34 O 11 was obtained from HR-FAB-MS representing fifteen unsaturations. The IR spectrum exhibited functional groups, hydroxyl (3396 cm Three new cyclolignan esters and seven known compounds including two cyclolignan isolariciresinol, lynoiresinol, and five aromatic compounds methyl ferulate, vanillin, 4-hydroxy-3,5-dimethoxybenaldehyde, 4-methoxygallic acid, gallic acid were isolated from n-butanol extract of Rhus semialata (Anacardiaceae). The structural elucidations of rhusemialins A (1), B (2), and C (3) were based on FAB-MS, 1D and 2D NMR spectra.

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Seven aromatic compounds from bark of Cinnamomum cassia

Cited by 86 publications

References 19 publications

Tarennanosides A–H, Eight New Lignan Glucosides from Tarenna attenuata and Their Protective Effect on H₂O₂‐Induced Impairment in PC12 Cells

Tarennanosides A–H, Eight New Lignan Glucosides from Tarenna attenuata and Their Protective Effect on H₂O₂‐Induced Impairment in PC12 Cells

Isolation and antitrichomonal activity of the chemical constituents of the leaves of Maytenus phyllanthoides Benth. (Celastraceae)

Rhusemialins A-C, New Cyclolignan Esters from the Roots of Rhus javanica var. roxburghiana

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Seven aromatic compounds from bark of Cinnamomum cassia

Cited by 86 publications

References 19 publications

Tarennanosides A–H, Eight New Lignan Glucosides from Tarenna attenuata and Their Protective Effect on H2O2‐Induced Impairment in PC12 Cells

Tarennanosides A–H, Eight New Lignan Glucosides from Tarenna attenuata and Their Protective Effect on H2O2‐Induced Impairment in PC12 Cells

Isolation and antitrichomonal activity of the chemical constituents of the leaves of Maytenus phyllanthoides Benth. (Celastraceae)

Rhusemialins A-C, New Cyclolignan Esters from the Roots of Rhus javanica var. roxburghiana

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Tarennanosides A–H, Eight New Lignan Glucosides from Tarenna attenuata and Their Protective Effect on H₂O₂‐Induced Impairment in PC12 Cells

Tarennanosides A–H, Eight New Lignan Glucosides from Tarenna attenuata and Their Protective Effect on H₂O₂‐Induced Impairment in PC12 Cells