Four secoiridoid glucosides from fraxinus insularis

Tanahashi, Takao; Parida,; Takenaka, Yasuhiro; Nagakura, Naotaka; Inoue, Ken‐ichiro; Kuwajima, Hiroshi; Chen, Chen-Chang

doi:10.1016/s0031-9422(97)00697-3

Cited by 20 publications

(5 citation statements)

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“…The ethanolic extract of the stem bark of F. sieboldiana was partitioned between H 2 O and EtOAc. The H 2 O phase was subjected to separation using various column chromatographic techniques to afford nine new glycosides (1)(2)(3)(4)(5)(6)(7)(8)(9).…”

Section: Resultsmentioning

confidence: 99%

“…Its dried bark has long been used as a folk medicine "Qin Pi" in China and Japan, as it is reported to have diuretic, antifebrile, analgesic, and antirheumatic activities. 1,2 Many coumarins, 3,4 lignans, 5 secoiridoid glucosides, [6][7][8] and phenylethanoids 9 have been reported from species of this genus. As part of a program to assess the chemical and biological diversity of traditional Chinese medicines, we undertook investigation of the stem bark of F. sieboldiana and describe herein isolation and structural elucidation of a new norditerpene glucopyranoside (1) and eight new aromatic glycosides (2)(3)(4)(5)(6)(7)(8)(9), along with 25 known glycosides.…”

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confidence: 99%

“…1,2 Many coumarins, 3,4 lignans, 5 secoiridoid glucosides, [6][7][8] and phenylethanoids 9 have been reported from species of this genus. As part of a program to assess the chemical and biological diversity of traditional Chinese medicines, we undertook investigation of the stem bark of F. sieboldiana and describe herein isolation and structural elucidation of a new norditerpene glucopyranoside (1) and eight new aromatic glycosides (2)(3)(4)(5)(6)(7)(8)(9), along with 25 known glycosides. Some biological assay results are also reported.…”

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confidence: 99%

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Glycosides from the Stem Bark of Fraxinus sieboldiana

et al. 2007

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A norditerpene glucopyranoside with a novel carbon skeleton (1), eight new aromatic glycosides (2-9), and 25 known glycosides have been isolated from a H2O-soluble portion of an ethanolic extract of the stem bark of Fraxinus sieboldiana. Their structures were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo- and erythro-arylglycerols in different solvents, an application of Delta delta C8-C7 values to distinguish threo-arylglycerol and erythro-arylglycerol isomers was proposed. In the in vitro assays, compound 5 displayed TNF-alpha secretion inhibitory activity with an IC50 value of 1.6 microM, compound 6 showed antioxidative activity inhibiting Fe+2-cystine-induced rat liver microsomal lipid peroxidation with an IC50 value of 0.9 microM, and plantasioside (10) showed selective activity against the human colon cancer cell line (HCT-8) with an IC50 value of 3.4 microM.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Glycosides from the Stem Bark of Fraxinus sieboldiana

et al. 2007

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“…The genus Fraxinus , a member of the Oleaceae family, is a rich source of bioactive metabolites including coumarins, lignans, secoiridoid glucosides, and phenylethanoids. − Our previous investigation of the stem bark of Fraxinus sieboldiana Blume (Oleaceae), a folk medicine with diuretic, antifebrile, analgesic, and antirheumatic activities, resulted in characterization of a unique norditerpene glucopyranoside and 33 aromatic glycosides from the water-soluble fraction of an ethonolic extract . As part of our ongoing effort to study the chemical and biological diversity of this plant, we report herein the isolation, structure elucidation, and biological assays of 14 new abietane diterpenes ( 1 − 14 ), seven new C 20 -norabietane diterpenes ( 15 − 21 ), and five known analogues from the EtOAc-soluble fraction of the ethonolic extract.…”

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Abietane and C₂₀-Norabietane Diterpenes from the Stem Bark of Fraxinus sieboldiana and Their Biological Activities

et al. 2010

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Fourteen new abietane (1-14) and seven new C(20)-norabietane (15-21) diterpenes, together with five known analogues, have been isolated from the stem bark of Fraxinus sieboldiana. Their structures were elucidated by spectroscopic data analysis. In the in vitro assays, at 10(-5) M, compounds 8, 16, and 22 showed inhibitory activity against the release of β-glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor, with 59.7 ± 4.8%, 56.1 ± 5.6%, and 65.9 ± 3.1% inhibition, respectively. Compound 23 was active against H5N1 avian influenza virus with an IC(50) value of 4.8 μM. Compounds 3 and 5 exhibited selective cytotoxic activities against A2780 (IC(50) 1.7 μM) and A549 (IC(50) 6.0 μM), respectively.

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“…Previous phytochemical studies of the species resulted in isolation of caffeic glycoside esters . In the course of our chemical studies on the secoiridoid glucosides from oleaceous plants, we have investigated the leaves and stems of J. nudiflorum . We report here the isolation and structure elucidation of three glucosides ( 1 − 3 ), each consisting of oleoside units and a cyclopentanoid monoterpene unit.…”

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confidence: 99%