Phenylpropane Glycosides from<i>Juniperus phœnicea</i>

Comte, Gilles; Chulia, Albert J.; Vercauteren, Joseph; Allais, Daovy

doi:10.1055/s-2006-957817

Cited by 24 publications

(11 citation statements)

References 3 publications

(3 reference statements)

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“…Fraction G-1 (CHCl 3 :MeOH, 100:8) (3.3 g) was separated via HPLC with MeOH:H 2 O (35:65, v / v ) as the mobile phase to produce compound 2 (82 mg). The structures of compounds 1 – 7 were identified by comparing their spectroscopic data with those reported in the literature [ 33 , 34 , 35 , 36 , 37 ]. The relevant chromatograms and mass spectral data of the active compounds are as follows.…”

Section: Methodsmentioning

confidence: 99%

Preventive Effects of Rhodiola rosea L. on Bleomycin-Induced Pulmonary Fibrosis in Rats

Zhang

Si²,

Huang

et al. 2016

IJMS

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Rhodiola rosea L. (RRL) possesses a wide range of pharmacological properties, including lung-protective activity, and has been utilized in folk medicine for several 100 years. However, the lung-protective mechanism remains unclear. This study investigated the possible lung-protective activity mechanism of RRL in a pulmonary fibrosis (PF) rat model. Lung fibrotic injury was induced in Sprague–Dawley rats by single intratracheal instillation of saline containing bleomycin (BLM; 5 mg/kg). The rats were administered 125, 250, or 500 mg/kg of a 95% ethanol extract of RRL for 28 days. The animals were killed to detect changes in body weight, serum levels of glutathione (GSH) and total superoxide dismutase (T-SOD), as well as lung tissue hydroxyproline (HYP) content. Tumor necrosis factor-α (TNF-α), transforming growth factor-β1 (TGF-β1), and interleukin 6 (IL-6) levels were measured in bronchoalveolar lavage fluid (BALF) by enzyme-linked immunosorbent assay. Hematoxylin and eosin, Masson’s trichrome, and immunohistochemical staining were performed to observe the histopathological changes in lung tissues. Additionally, target-related proteins were measured by Western blotting. RRL alleviated the loss of body weight induced by instilling BLM in PF rats, particularly at the 500 mg/kg per day dose. RRL reduced HYP (p < 0.01) and increased GSH and T-SOD contents. BALF levels of TNF-α, TGF-β1, and IL-6 decreased significantly in the RRL-treated groups. Expression levels of matrix metalloproteinase-9 (MMP-9) and α-smooth muscle actin decreased significantly in a dose-dependent manner in response to RRL. Moreover, the levels of TGF-β1 and tissue inhibitor of metalloproteinase-1 in lung tissues also decreased in the RRL-treated groups. RRL alleviated BLM-induced PF in rats. Our results reveal that the protective effects of RRL against fibrotic lung injury in rats are correlated with its anti-inflammatory, antioxidative, and anti-fibrotic properties. MMP-9 may play important roles in BLM-induced PF.

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Section: Methodsmentioning

confidence: 99%

Preventive Effects of Rhodiola rosea L. on Bleomycin-Induced Pulmonary Fibrosis in Rats

Zhang

Si²,

Huang

et al. 2016

IJMS

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“…It is worth of note that most of studies on J. phoenicea are related to its monoterpene-rich essential oil [14] [25 -29] and the monoterpene hydrocarbon a-pinene emerged as the principal characterizing volatile compound. Conversely, the non-volatile secondary metabolites were investigated to a minor extent, and the following classes of natural products were the main groups of secondary metabolites characterizing the species J. phoenicea: abietane diterpenoids, [19] [30] sesquiterpenes, [31] norterpenoid glucosides, [32] scutellarein derivatives, [33] furanones, phenylpropane glucosides [17] [34] [35] and lignans. [36] However, in this context, J. turbinata has hitherto been poorly explored and showed labdane diterpenes as the main constituents.…”

Section: Introductionmentioning

confidence: 99%

Bioactive Constituents ofJuniperus turbinataGuss. from La Maddalena Archipelago

Venditti

Maggi

Quassinti

et al. 2018

Chemistry & Biodiversity

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A comprehensive phytochemical study of Juniperus turbinata (Cupressaceae) collected from La Maddalena Archipelago (Sardinia, Italy) is reported. Both the essential oil and the ethanolic extract obtained from the aerial parts were analyzed. The essential oil appears to belong to a new chemotype compared to other Mediterranean juniper accessions, as it was favored by geographic isolation of the isles. It showed a low content of monoterpene hydrocarbons and α-terpineol, ent-manoyl oxide, 1,10-di-epi-cubenol as the major constituents. The ethanolic fraction contained mainly diterpenoids. Among these, 15-formyloxyimbricatolic acid (7) is a new natural product since it has hitherto been obtained only by synthetic route. The phenolic fraction contained biflavonoids: cupressuflavone (9), followed by minor amounts of amentoflavone (10) and hinokiflavone (11). The essential oil and six purified compounds (1 - 4, 8 and 9) were assessed for biological activities, namely antioxidant (assessed by DPPH , ABTS and FRAP methods) and cytotoxic effects towards selected human tumor cell lines (MDA-MB 231, A375 and HCT116 cells). Compound 3 exhibited higher radical scavenging activity against ABTS radical than the reference Trolox. Noteworthy, compound 8 showed powerful effects towards tumor cell lines, with IC values in the range of 0.060 - 0.201 μm, which make it a promising anticancer drug candidate.

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“…The methanol-eluted fraction was subjected to normal-and reversed-phase column chromatographies, and finally HPLC to give sachalosides I (1, 0.0004%), II (2, 0.0005%), III (3, 0.0003%), IV (4, 0.0004%), and V (5, 0.0007%), together with 21 known compounds, geranyl 1-O-a-L-arabinofuranosyl(1→6)-b-D-glucopyranoside (7, 0.0029%), 27) kenposide A (8, 0.0028%), 28) sacranoside A (10, 0.0011%), 15) rhodiocyanoside A (11, 0.23%), 14) lotaustralin (12, 0.0014%), 29) hetorodendrin (13, 0.0002%), 30) benzyl b-D-glucopyranoside (14, 0.0022%), 31) 34) salidroside (19, 0.10%), 35) 2-(4-methoxyphenyl)-ethyl b-D-glucopyranoside (20, 0.0004%), 36) trans-cinnamyl b-D-glucopyranoside (23, 0.0046%), 37) rosarin (24, 0.0097%), 38) rosavin (27, 0.034%), 39) 40) gein (29, 0.0007%), 41) nodakenin (31, 0.0021%), 42) leucoside (35, 0.0028%), 32) rhodiosin (36, 0.014%), 43) 1-octyl-a-D-arabinofuranosyl(1→6)-b-D-glucopyranoside (39, 0.0009%).…”

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confidence: 99%

Bioactive Constituents from Chinese Natural Medicines. XXVI. Chemical Structures and Hepatoprotective Effects of Constituents from Roots of Rhodiola sachalinensis

Nakamura

Matsuda

et al. 2007

Chem. Pharm. Bull.

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The roots of the alpine Rhodiola (Crassulaceae) plant, Rhodiolae Radix, have been widely used as a hemostatic, antibechic, tonic, and endermic liniment for burns and contusions in traditional Chinese medicine. Chemical and biological studies on several Rhodiola plants have been reported. [2][3][4][5] For example, the methanolic extract from the roots of R. sachalinensis was reported to show inhibitory activity on prolyl endopeptidase. 4) During the course of our serial studies on the bioactive constituents from Chinese natural medicines, 1,[6][7][8][9][10][11][12][13] we have characterized the structures of several monoterpene oligoglycosides and cyanogenic glycosides from the roots of R. quadrifida (PALL.) FISCH. et MAY and R. sacra (PRAIN ex HAMET) S. H. FU.14,15) Among the isolated constituents, monoterpene oligoglycosides, sacranosides A and B, were found to inhibit histamine release from rat exudate cells induced by an antigen-antibody reaction.15) As a continuing study on the bioactive constituents of Rhodiolae Radix, the methanolic extract from the roots of R. sachalinensis A. BOR. was found to show a protective effect on Dgalactosamine (D-GalN)-induced cytotoxicity in primary cultured mouse hepatocytes. From the methanolic extract, we have isolated two new monoterpene glycosides, sachalosides I and II, two new flavonol bisdesmosides, sachalosides III and IV, a new cyanogenic glycoside, sachaloside V, together with 34 known compounds. Furthermore, we examined the protective effects of principal constituents on D-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. In this paper, we describe the isolation and structure elucidation of the new constituents (1-5) and the hepatoprotective effects of principal constituents from the roots of R. sachalinensis.The roots of R. sachalinensis were extracted with methanol under reflux. The methanolic extract (14.6% from the roots) was partitioned into an EtOAc-H 2 O mixture to furnish an EtOAc-soluble fraction (3.5%) and aqueous layer. The aqueous layer was further extracted with n-BuOH to give n-BuOH and H 2 O-soluble fractions (4.4% and 6.5%, respectively). As shown in Table 1, the methanolic extract and the EtOAc-and n-BuOH-soluble fractions were found to show hepatoprotective effects, but the H 2 O-soluble fractions showed weak effect. The EtOAc-soluble fraction was subjected to normal-phase and reversed-phase column chromatographies, and finally HPLC to give 13 known compounds, geranyl b-D-glucopyranoside (6, 0.0070%), kaempferol (34, 0.023%), 25) tricin (37, 0.0069%), 26) 1-octylb-D-glucopyranoside (38, 0.0019%).18) The n-BuOH-soluble fraction was also subjected to Diaion HP-20 column chromatography (H 2 O→MeOH) to give the water-and methanoleluted fractions (0.8% and 3.5%, respectively). The methanol-eluted fraction was subjected to normal-and reversed-phase column chromatographies, and finally HPLC to give sachalosides I (1, 0.0004%), II (2, 0.0005%), III (3, 0.0003%), IV (4, 0.0004%), and V (5, 0.0007%), together with 21 known compounds, geranyl 1...

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Phenylpropane Glycosides fromJuniperus phœnicea

Cited by 24 publications

References 3 publications

Preventive Effects of Rhodiola rosea L. on Bleomycin-Induced Pulmonary Fibrosis in Rats

Preventive Effects of Rhodiola rosea L. on Bleomycin-Induced Pulmonary Fibrosis in Rats

Bioactive Constituents ofJuniperus turbinataGuss. from La Maddalena Archipelago

Bioactive Constituents from Chinese Natural Medicines. XXVI. Chemical Structures and Hepatoprotective Effects of Constituents from Roots of Rhodiola sachalinensis

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