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Objective: To study the antitumor constituents from Chloranthus fortunei. Methods: Various chromatographic techniques and spectroscopic methods were applied to investigate the chemical constituents from C. fortunei, and some of the compounds were screened for their antitumor activities by MTT method. Results: Sixteen compounds were obtained from the whole plants of C. fortunei and identified as rosmarinic acid (1), 2’-hydroxy-4,3’,4’,6’-tetramethoxychalcone (2), flavokawain A (3), cycloshizukaol A (4), atractylenolide III (5), 4β-hydroxy-8,12-epoxyeudesma-7,11-diene-1,6-dione (6), (8α)-6,8-dihydroxycadina-7 (11),10 (15)-dien-12-oic acid γ-lactone (7), curcolonol (8), 11-hydroxyldrim-8,12-en-14-oic acid (9), friedelin (10), isovanillic acid (11), 6β-hydroxystigmast-4-en-3-one (12), 3,4-dihydroxybenzoic acid (13), shikimic acid (14), scopolin (15) and N-acetyltyramine 1-O-β-D-glucoside (16). Compounds 4 and 5 showed weak cytotoxicity with IC50 ranged from 46 to 85 μmol/L. Conclusion: Compounds 2, 10, 11, and 13-15 are obtained from the genus Chloranthus for the first time and compounds 1-3 and 6-16 are isolated from C. fortunei for the first time. Some sesquiterpenoids from C. fortunei exhibited weak antitumor activities.
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Objective To investigate the effects of friedelin (terpenoid) and 8-hydroxyisocapnolactone-2-3-diol (coumarin) with concentration 10 μM, 30 μM, and 100 μM on inhibiting mast cells (MCs) degranulation. Methods The investigation was performed in vitro by administering each compound into rat peritoneal MCs and rat basophilic leukemia-2H3 cells followed by activation with 50 μg/mL of compound 48/80 or 1 μM of ionomycin. The concentration of histamine released from each group was measured by a high-performance liquid chromatography-fluorometry system with post-column derivatization using o-phthalaldehyde. Results 8-Hydroxyisocapnolactone-2-3-diol inhibited degranulation of compound 48/80 activated-rat peritoneal MCs with the histamine release percentages of 74.57%, 72.21% and 51.79% when the 10 μM, 30 μM and 100 μM concentrations were used, respectively. Where as about 81% histamine was released by the control group. Degranulation inhibition ability was also observed in ionomycin-activated rat basophilic leukemia-2H3 cells. In contrast, friedelin failed to inhibit degranulation in either cell type. The inhibition of 8-hydroxyisocapnolactone-2-3-diol was not related to the depletion of histamine synthesis as implied by the total histamine measurement. Conclusions These results exhibit the promising of 8-hydroxyisocapnolactone-2-3-diol is a potential parent structure for developing a MCs stabilizer.
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OBJECTIVE@#To investigate the effects of friedelin (terpenoid) and 8-hydroxyisocapnolactone-2-3-diol (coumarin) with concentration 10 μM, 30 μM, and 100 μM on inhibiting mast cells (MCs) degranulation.@*METHODS@#The investigation was performed in vitro by administering each compound into rat peritoneal MCs and rat basophilic leukemia-2H3 cells followed by activation with 50 μg/mL of compound 48/80 or 1 μM of ionomycin. The concentration of histamine released from each group was measured by a high-performance liquid chromatography-fluorometry system with post-column derivatization using o-phthalaldehyde.@*RESULTS@#8-Hydroxyisocapnolactone-2-3-diol inhibited degranulation of compound 48/80 activated-rat peritoneal MCs with the histamine release percentages of 74.57%, 72.21% and 51.79% when the 10 μM, 30 μM and 100 μM concentrations were used, respectively. Where as about 81% histamine was released by the control group. Degranulation inhibition ability was also observed in ionomycin-activated rat basophilic leukemia-2H3 cells. In contrast, friedelin failed to inhibit degranulation in either cell type. The inhibition of 8-hydroxyisocapnolactone-2-3-diol was not related to the depletion of histamine synthesis as implied by the total histamine measurement.@*CONCLUSIONS@#These results exhibit the promising of 8-hydroxyisocapnolactone-2-3-diol is a potential parent structure for developing a MCs stabilizer.
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Abstract The hypolipidemic activity of friedelin isolated from Azima tetracantha Lam., Salvadoraceae, was studied in Triton WR-1339 and high-fat diet-induced hyperlipidemic rats. In Triton WR-1339 induced hyperlipidemic rats, treatment with friedelin (50 and 70 mg/kg) showed a significant (p < 0.01) lipid-lowering effect as assessed by reversal of plasma levels of total cholesterol (TC), triacylglycerides (TG), high-density lipoprotein cholesterol (HDL-C) and low-density lipoprotein cholesterol (LDL-C). In high-fat diet fed hyperlipidemic rats, treatment with friedelin (50 and 70 mg/kg) caused lowering of lipid levels in plasma and liver. The hypolipidemic activity of friedelin was compared with fenofibrate, a known lipid-lowering drug, in both models.
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The triterpenes, squalene (1), friedelin (2) and a mixture of ursolic acid (3a) and oleanolic acid (3b) in a 2:3 ratio, and a mixture of β-sitosterol (4a) and stigmasterol (4b) in a 2:1 ratio, obtained from the dichloromethane extract of Pipturus arborescens (Link) C.B. Rob., were evaluated for their anti-proliferative activities against three human cancer cell lines, breast (MCF-7) and colon (HT-29 and HCT-116), and a normal cell line, human dermal fibroblast- neonatal (HDFn) using the in vitro PrestoBlue® cell viability assay. The HCT-116 cell line was most susceptible to the compounds and mixtures tested. Triterpene 1 was most cytotoxic against HCT-116 and MCF-7 with IC50 values of 4.21 and 5.92 μg/mL, respectively. Triterpene 2 and the mixture of 3a and 3b were highly anti-proliferative against HCT-116 cells (IC50 of 1.22 and 1.66 μg/mL, respectively) and moderately inhibitory against MCF-7 cells (IC50 of 16.51 and 23.97 μg/mL, respectively). The mixture of 4a and 4b exhibited high cytotoxicity against HCT-116 cells (IC50 of 1.14 μg/mL). Compounds 1-4b showed the least activity against HT-29 cells (IC50 of 11.97 to 52.52 μg/mL). Cytotoxic effect was not observed against HDFn cells (>100 μg/mL). Comparing the effects of 1-4b on the two colon cancer cell lines, the IC50 values of 1-4b against HCT-116 were lower than those of HT-29.
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To study the non-alkaloid constituents from the stems and leaves of Ochrosia borbonica. The chemical constituents were separated and purified by silica gel, Sephadex LH-20, ODS column chromatographies, and preparative HPLC. Their structures were determined by physicochemical properties, spectral data, as well as comparison with the data in literature. Fifteen compounds were isolated from the petroleum ether fraction of 70% ethanol extract from the stems and leaves of O. borbonica, and identified as lupeol (1), lupine ketone (2), betulinic alcohol (3), betulinic acid (4), ursolic acid (5), 2α, 3β-dihydroxy-ursolic acid (6), 11, 12-dehydroursolic acid lactone (7), β-amyrin (8), oleanolic lactone (9), alphitolic acid (10), friedelin (11), cholesterol (12), 24R-ethyl-5α-cholestane-3β, 6α-diol (13), stigmast-7-en-3β-ol (14), and β-sitosterol (15). All the compounds are isolated from the plants of Ochrosia Juss. for the first time.
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Combretum duarteanum Cambess, Combretaceae, is a plant widely distributed in Northeastern Brazil and, in folk medicine, stems and leaves are used for pain treatment. We investigated the antinociceptive effects of the hexanic extract of leaves from C. duarteanum and of friedelin, its main compound, in formalin-, glutamate- and capsaicin- induced orofacial nociception models. In order to isolate friedelin from the hexanic extract, flash chromatography technique was used. Male mice (n = 8/group) were pretreated with hexanic extract, friedelin, morphine or vehicle, before the injection of algogen agents into the right upper lip (perinasal area). The test of formalin-induced orofacial nociception showed that hexanic extract and friedelin significantly reduced nociception (p < 0.001) in both phases of testing. In the glutamate and capsaicin-induced orofacial nociception tests, pre-treatment with hexanic extract produced a significant reduction of orofacial nociception (p < 0.001) at all doses tested.The results suggest the hexanic extract and friedelin possess antinociceptive effects in models of orofacial nociception in rodents.
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Objective: To study the chemical constituents from Kalimeris indica. Methods: Chemical constituents were isolated by column chromatography and semi-prepared HPLC, and the structures were elucidated by spectral data and physical-chemical properties. Results: Fifthteen compounds were isolated and respectively identified as friedelin (1), epifriedelanol (2), stimasterol (3), β-sitosterol (4), α-spinasterol (5), erythodiol (6), octadecanoic acid (7), fraxinellone (8), β-daucosterol (9), hexacosanol (10), ergoaterol (11), sphondin (12), dibntyl phthalate (13), oleanic acid (14), and dammerdienly acetate (15). Conclusion: Compounds 5, 8-13 are isolated from K. indica for the frist time. Compounds 1, 3, 5, 8, and 12 have inhibitory effects on Cytospora sp. and Rhizoctonia solani.
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Objective: To investigate the chemical constituents of Daphne gracilis. Methods: The constituents were separated and purified by chromatographic methods and their structures were elucidated by spectroscopic methods and chemical analyses. Results: Fifteen compounds were obtained and identified as β-sitosterol (1), friedelin (2), stigmast-4-ene-3-one (3), stigmast-4-ene-3, 6-dione (4), lupeol (5), stigmasterol (6), 1, 3-distearate glycerol (7), glycerin-docosanate (8), octadecanol (9), phytol (10), dehydrodiconiferyl alcohol (11), epoxyconiferyl alcohol (12), oleodaphnone (13), 14-gingerol (14), and matairesinol (15). Conclusion: All the compounds are isolated from the plants of D. gracilis for the first time. Among them, compound 2-4, 7-9, 11, 12, and 14 are isolated from the plants in Daphne L. for the first time; Compounds 11, 12, and 14 are isolated from the plants of family Thymelaeaceae for the first time.
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Objective: To isolate and identify the chemical constituents of Ainsliaea latifolia. Methods: Compounds were isolated by various kinds of column chromatographies on silica gel, Sephadex LH-20, MPLC, and HPLC, and their structures were elucidated by the physicochemical properties and spectral analyses. Results: Thirteen chemical constituents were obtained and identified as friedelin (1), taraxeryl acetate (2), 3β-hydroxy-11α, 12α-epoxy-friedoolean-14-ene (3), careborin (4), cis-careborin (5), 3α-E-feruloyltaraxerol (6), 3α-Z-feruloyltaraxerol (7), 3-oxo-11α-methoxyolean-12-ene (8), diaspanolide A (9), diaspanolide B (10), ainsliaolide A (11), stigmasterol (12), and β-sitosterol (13). Conclusion: Among the isolated 13 compounds, there are 8 triterpenoids (1-8), 3 sesquiterpenoids (9-11), and 2 steroidals (12-13). All the compounds are isolated from A. latifolia for the first time.
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Objective: To study the chemical constituents from Liparis nervosa. Methods: The column chromatography on silica gel, MCI gel, ODS, and Sephadex LH-20 columns was applied for the isolation and purification of the chemical constituents. The structures were identified based on physicochemical property and spectral data. Results: Nine compounds were isolated and identified as (hexahydro-1H-pyrrolizin-1-yl) methyl-2, 2-dimethyl-8-(3-hydroxyisoamyl) chroman-6-carboxylate (1), friedelin (2), α-spinasterol (3), p-hydroxybenzaldehyde (4), swertisin (5), 6, 8-di-C-α-L-arabinopyranosyl apigenin (6), 6, 8-di-C-α-L-arabinopyranosyl genkwanin (7), 8-C-α-L-arabinopyranosyl apigenin (8), and thymidine (9). Conclusion: Compound 1 is a new compound named nervosine B, and compounds 2-9 are isolated from L. nervosa for the first time.
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A espécie Celtis iguanaea (Jacq.) Sargent é popularmente conhecida como esporão de galo ou grão de galo. As folhas são indicadas pelo uso popular para o tratamento de dores no corpo e no peito, para reumatismo, asma, cólicas, má digestão e como diurético; as raízes são utilizadas para infecções urinárias e as cascas para a febre. O presente trabalho objetivou contribuir para o estudo fitoquímico e atividade fitotóxica com enfoque alelopático das cascas de Celtis iguanaea. O extrato etanólico foi submetido à partição com os solventes hexano, clorofórmio e acetato de etila. As substâncias friedelina e epifriedelinol (triterpenos) foram isoladas da fração hexano e identificadas por meio de métodos espectroscópicos de RMN de ¹H e 13C. O extrato bruto na concentração de 0,1 mg mL-1 causou inibição acentuada do hipocótilo em 34,97% e estimulou o crescimento da radícula em 29,64% de plântulas de Lactuca sativa. No ensaio de toxicidade frente à Artemia salina o extrato bruto e frações apresentaram uma CL50 superior a 1000 μg mL-1, indicando que o mesmo não possui efeito tóxico.
The species Celtis iguanaea (Jacq.) Sargent is popularly known as "esporão de galo" or "grão de galo". Its leaves are recommended by the popular use for the treatment of body and chest aches, as well as for rheumatism, asthma, cramps, indigestion and as diuretic; its roots are used for urinary infections and its bark for fever. This study aimed to contribute to the phytochemical investigation of the toxic activity focused on the allelopathic effect of the bark of Celtis iguanaea. The ethanol extract was subjected to solvent partition with hexane, chloroform and ethyl acetate. The substances friedelin and epifriedelinol (triterpenes) were isolated from the hexane fraction and identified by spectroscopic methods ¹H and 13C NMR. The crude extract at a concentration of 0.1 mg mL-1 caused marked inhibition of hypocotyl in 34.97% and stimulated radicle growth in 29.64% seedlings of Lactuca sativa. In the toxicity test against Artemia salina the crude extract and fractions showed an LC50 higher than 1000 μg mL-1, indicating that it has no toxic effect.