Indonesian Medicinal Plants. IV. On the Constituents of the Bark of Fagara rhetza (Rutaceae). (2). Lignan Glycosides and Two Apioglucosides.

Shibuya, Hitoshi; Takeda, Yasuharu; Zhang, Rusong; Tanitame, Akihiko; Tsai, Yen-Li; Kitagawa, Isao

doi:10.1248/cpb.40.2639

Cited by 47 publications

(32 citation statements)

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“…12,15) The BuOH soluble fraction of the extract was subjected to ODS column chromatography followed by ODS HPLC to afford 6 (5.2 mg, 1.0ϫ10 Ϫ3 %) 14) and 8 (22.9 mg, 4.6ϫ10 Ϫ3 %). 14,18) The aqueous fraction of the extract was subjected to ODS column chromatography followed by ODS HPLC to afford 5 (2.0 mg, 4.0ϫ10 Ϫ4 %), 21,22) (Table 1). Among nine compounds isolated, 3, 7, and 5 showed potent CYP3A4 inhibitory activities with IC 50 values of 3.6, 17, and 20 mM, respectively.…”

Section: Resultsmentioning

confidence: 99%

CYP3A4 Inhibitors Isolated from Licorice

Tsukamoto

Aburatani

Yoshida

et al. 2005

Biological & Pharmaceutical Bulletin

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Cytochrome P450 (CYP) enzymes are responsible for metabolism of a wide range of endogeneous compounds and xenobiotics, e.g. drug molecules, pollutants, and environmental compounds. Among members of the CYP enzyme family, CYP3A4 is the most abundant enzyme in human liver microsomes and intestinal epithelium; approximately 30% of the total CYP was suggested to be CYP3A4, 1) and more than 50% of clinically used drugs are oxidized by CYP3A4.2,3) It is well known that concomitant oral administration of several foods and herbs affects drug metabolism in humans by inhibiting CYP3A4 activity. In the course of our study on CYP inhibitors from foods, we have reported the isolation and structure elucidation of CYP inhibitors from grapefruit (Citrus paradisii) juice, [4][5][6] white pepper, Piper nigrum, 7,8) strawberry fruit, Fragaria ananassa, 9) and the commercially available black cohosh, Cimicifuga racemosa. 10) Licorice is prescribed in many Chinese traditional medicines and has been reported to contain flavonoids and triterpenoids. [11][12][13][14][15][16][17][18][19] Recently, we found that the extract of licorice (Glycyrrhiza uralensis FISHER, Leguminosae) showed potent CYP3A4 inhibitory activity with the IC 50 value of 0.022 mg/ml. This paper reports the isolation, structure identification, and CYP inhibitory activity of the constituents of licorice. MATERIALS AND METHODS General ProceduresOptical rotations were determined with a Horiba SEPA-300 high sensitive polarimeter. NMR spectra were recorded on a JEOL GSX500 NMR spectrometer. Mass spectra were measured on a JEOL SX-102 mass spectrometer.Plant Materials The rhizomes of G. uralensis were purchased from Tochimoto Co., Ltd. (Osaka, Japan). A voucher specimen is deposited in the Laboratory of Pharmacognosy and Chemistry of Natural Products, Graduate School of Natural Science and Technology, Kanazawa University, Japan.Isolation of Compounds 1-9 The rhizomes (0.5 kg) of G. uralensis were extracted with methanol (MeOH) (3 lϫ3) at room temperature. The extract was evaporated in vacuo, and the residue was partitioned between ethyl acetate (EtOAc) and water (H 2 O). The aqueous fraction was then partitioned between butanol (BuOH) and water. The EtOAc soluble fraction (34.7 g) was subjected to column chromatography on silica gel with hexane/EtOAc followed by ODS column chromatography with MeOH/H 2 O to afford 1-4 (Fig. 1). The BuOH soluble fraction (34.9 g) was subjected to column chromatography on ODS with MeOH/H 2 O followed by ODS HPLC with MeOH/H 2 O to afford 6 and 8. The aqueous fraction (31.3 g) was subjected to column chromatography on ODS with MeOH/H 2 O followed by ODS HPLC with MeOH/H 2 O to afford 5, 7, and 9.Assay of CYP3A4 Inhibition CYP3A4 activity was measured based on nifedipine oxidation. Various amounts (0-10 mM, final concentration) of samples in 1 ml of dimethylsulfoxide (DMSO) were added to 192 ml of 100 mM phosphate buffer (pH 7.4) containing 50 mM nifedipine (Wako Pure Chemical Industries, Ltd., Osaka, Japan), 5 mM glucose-6-phosphate (Oriental...

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Section: Resultsmentioning

confidence: 99%

CYP3A4 Inhibitors Isolated from Licorice

Tsukamoto

Aburatani

Yoshida

et al. 2005

Biological & Pharmaceutical Bulletin

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“…In this study, purification of the EtOAc and n-BuOH fractions of Z. schinifolium stems by silica gel and YMC column chromatography afforded one new neolignan glycoside, zanthoxyloside A (1), and one newly monoterpenoid glycoside, zanthoxyloside B (2), together with 15 known glycosides (3)(4)(5)(6)(7)(8)(9)(10)(11)(12) and alkaloids (13)(14)(15)(16)(17). Their structures were elucidated as zanthoxyloside A (1), zanthoxyloside B (2), betulalbuside A (3), 13) 15) isopropyl apioglucoside (6), 16) benzyl 6-O-β-apiofuranosyl-O-β-glucopyranoside (7), 17) osmanthuside H (8), 18) coniferin (9), 19) syringin (10), 19) homovanillyl alcohol-4′-glycoside (11), 20) roseoside A (12), 21) skimmianine (13), 22) haplopine (14), 23) glycohaplopine (15), 24) norchelerythrine (16), 25) and nornitidine (17).…”

Section: Resultsmentioning

confidence: 89%

“…Their structures were elucidated as zanthoxyloside A (1), zanthoxyloside B (2), betulalbuside A (3), 13) 15) isopropyl apioglucoside (6), 16) benzyl 6-O-β-apiofuranosyl-O-β-glucopyranoside (7), 17) osmanthuside H (8), 18) coniferin (9), 19) syringin (10), 19) homovanillyl alcohol-4′-glycoside (11), 20) roseoside A (12), 21) skimmianine (13), 22) haplopine (14), 23) glycohaplopine (15), 24) norchelerythrine (16), 25) and nornitidine (17). 25) Compounds 4, 5, 8, 11, 15, and 17 were isolated from Z. schinifolium for the first time (Fig.…”

Section: Resultsmentioning

confidence: 99%

NF-κB Inhibitory Activities of Glycosides and Alkaloids from <i>Zanthoxylum schinifolium</i> Stems

Yang

Yan

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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Zanthoxylum schinifolium is an aromatic shrub, the pericarp and leaves of which are widely used in culinary applications in East Asian countries. In the present study, one new neolignan glycoside, zanthoxyloside A (1) together with 16 known glycosides (2-12) and alkaloids (13-17), were isolated from methanol extract of the stems of Z. schinifolium. The absolute configuration of one known monoterpenoid glycoside (2) was determined. The structures of the isolated compounds were established by one dimensional (1D), 2D NMR and mass spectrometry. The nuclear factor-κB (NF-κB) inhibitory activities of the isolated compounds stimulated with tumor necrosis factor alpha (TNFα) were measured using a luciferase reporter system. Compounds 1, 5, 16, and 17 exhibited significant inhibition of NF-κB activation in a dose-dependent manner. Furthermore, compounds 1, 5, 16, and 17 inhibited TNFα-induced expression of inducible nitric oxide synthase (iNOS) and intercellular adhesion molecule-1 (ICAM-1) mRNA and dose-dependent inhibition of iNOS promoter activity.Key words Zanthoxylum schinifolium; Rutaceae; glycoside; alkaloid; nuclear factor-κB (NF-κB) inhibitory activity Zanthoxylum schinifolium SIEB. & ZUCC., which belongs to the Rutaceae family, is an aromatic plant, widely used as a pungent condiment and seasoning in Korea, China, Japan and other East Asian countries because of its unique aroma and taste.1) The leaves and seeds of Z. schinifolium have been used primarily for treatment of various types of pain, the common cold, diarrhea, and jaundice in traditional Chinese medicine. Pharmacological research on Z. schinifolium has focused on its inhibitory effect on monoamine oxidase and its anti-platelet, anti-diabetes, and anti-inflammatory activities. 2-4)Phytochemical studies on Z. schinifolium indicated the main constituents to be coumarins, essential oils, triterpenoids, monoterpenoids, steroids, and flavonoids. [5][6][7] Coumarins were shown to have significant platelet aggregation activity. Essential oils were found to have antioxidant activity and are used in skin care products. Alkaloids have various bioactivities such as antimicrobial effects. 8) Although there have been many investigations of the active constituents of Z. schinifolium, there have been no detailed reports of the isolation and structural elucidation of glycosides and alkaloids from the stems of this plant or their bioactivities.Nuclear factor-κB (NF-κB) represents a family of Rel domain-containing proteins, which includes five NF-κB units that can form 15 transcription factors through homo-and heterodimerization. NF-κB plays an important role in the transcriptional regulation of numerous cytokines and adhesion molecules. It is the most extensively studied transcription factor in the immune system. Known inducers of NF-κB activity are highly variable and include reactive oxygen species (ROS), tumor necrosis factor alpha (TNFα), interleukin (IL)-1β, bacterial lipopolysaccharides (LPS), isoproterenol, cocaine, and ionizing radiation. The activation of NF-...

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“…On the basis of the comparison of their NMR spectroscopic data with those reported in the literature, the 28 known compounds were identified to be 2-benzoxazolinone (3), 6) tryptanthrin (4), 7) 2-hydroxy-1,4-benzoxazin-3-one (5), 8) 3-(2′-hydroxyphenyl)-4(3H)-quinazolinone (6), 9) 1H-indole-3-carbaldehyde (7), 10) benzouracil (8), 11) 2H-1,4-benzoxazin-3-one (9), 12) 3-carboxyindole (10), 13) acanthaminoside (11), 14) 4(3H)-quinazolinone (12), 15) deoxyvasicinone (13), 16) acanthaminoside isomer (14), 14) lupeol (15), 17) betulin (16), 18) betulinic acid (17), 19) ursolic acid (18), 20) lup-20(29)-en-3β,30-diol (19), 21) maslinic acid (20), 22) guaiacylglycerol-β-ferulic acid ether (21), 23) (2S,3R,4S)-lyoniresinol-3α-O-β-D-glucopyranoside (22), 24) (2R,3S,4R)-lyoniresinol-3α-O-β-D-glucopyranoside (23), 24) (+)-5,5′-dimethoxy-9-O-β-D-glucopyranosyl secoisolariciresinol (24), 25) tyrosol (25), 26) β-hydroxy-benzenepentanoic acid (26), 27) acteoside (27), 28) acteoside isomer (28), 28) loliolide (29), 29) hispiduloside (30). 30) Among these, compounds 3-14 belong to alkaloids (Fig.…”

Section: Resultsmentioning

confidence: 99%