Antiperoxidation activity of triterpenoids from rhizome of Anemone raddeana

Four triterpenoid compounds hederacolchiside E (1), hederasaponin B (2), raddeanoside 20 (3) and raddeanoside 21 (4) were isolated from ethanol extracts of rhizome of Anemone raddeana Regel. The effects of these triterpenoids on superoxide generation, tyrosyl phosphorylation of proteins and translocation of cytosolic compounds, such as p47^phox, p67^phox and Rac to the cell membrane in human neutrophils was investigated. The superoxide generation induced by N-formyl-methionyl-leucyl-phenylalanine (fMLP) was slightly suppressed by hederasaponin B, raddeanoside 20 and raddeanoside 21 in a concentration dependent manner. The superoxide generation induced by arachidonic acid (AA) was suppressed by hederasaponin B and raddeanoside 21 significantly. fMLP- and AA-induced tyrosyl phosphorylation and translocation of the cytosolic proteins: p47^phox, p67^phox, and Rac to the cell membrane were suppressed in parallel with the suppression of stimulus-induced superoxide generation.     

Two new cytotoxic triterpenoid saponins from the roots of Clematis argentilucida

Bioassay-guided fractionation of the n-BuOH extract of the roots of Clematis argentilucida led to the isolation of two new triterpenoid saponins along with a known one, cussonside B (3). By extensive spectral analysis and chemical evidences, the structures of the two new saponins were determined to be 3β-O-[β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] hederagenin-11,13-dien-28-oic acid (1) and 3β-O-{β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl} oleanolic acid (2), respectively. Saponin 1 is the first example of triterpenoid saponins with two double bonds located at C-11 and C-13 in the aglycone from the genus Clematis. The two new saponins exhibited significant cytotoxicity against human leukemia HL-60 cell lines, human hepatocellular carcinoma Hep-G2 cell lines and human glioblastoma U251MG cell lines with a range of IC(50) values from 2.74 to 25.40μM, while 3 showed inactivity against all of the three cancer cell lines.     

山杏叶桦木酸、齐墩果酸和熊果酸的研究

我国山杏资源十分丰富,是绿化荒山的优良树种。采用HydersirBDSC18色谱柱（150×4．6mm,5μm）,流动相体积比为90：10的0．3‰硫酸甲醇溶液一3‰硫酸水溶液,检测波长210nm,建立了山杏叶中三萜酸测定的高效液相色谱法。结果表明：桦木酸、齐墩果酸与熊果酸的浓度在30～2000μg／mL（r桦=0．9971,r齐=0．9986,r熊=0．9978）范围内与色谱峰面积呈良好线性关系;平均加标回收率分别为99．9％、101．1％和98．9％。以山杏叶为材料,采用高效液相色谱法和紫外可见分光光度法分别对山杏叶中的三萜酸成分进行分析,结果表明,山杏叶富含三萜酸,落叶期山杏叶中总三萜酸（17078#g／g）、桦木酸（1842μg／g）、齐墩果酸（2536μg／g）和熊果酸（5706μg／g）含量均高于非落叶期。本研究首次建立了山杏叶中桦木酸、齐墩果酸和熊果酸同时测定的反向高效液相色谱法（HPLC）,发现落叶期山杏叶富含三萜酸,为山杏叶综合开发利用提供了基础数据。     

Bioactive saponins from the fruits of Aesculus pavia L

Continued chemical investigation on the fruits of Aesculus pavia L. resulted in theisolation and identification of two new oleanolic acid saponins, namely vaccaroside A (1) andvaccaroside B (2). The isolated furostanol saponins were evaluated for cytotoxic activity againsthuman normal amniotic and human lung carcinoma cell lines using neutral red and MTT assays.In vitro experiments showed significant cytotoxicity in a dose dependent manner with IC50 valuesin the range of 27.80–79.02 μM.     

Plant growth regulation effects of triterpenoid saponins

 To investigate structure–activity relations between the sugar chain structures of triterpenoid saponins and their plant growth regulation effects, several monodesmosidic saponins with betulin as an aglycon were synthesized by chemical and enzymic reactions. Three triterpenoids (betulin, betulinic acid, oleanolic acid) and synthesized betulin glycosides were submitted to germination and growth regulation tests on alfalfa seeds. We concluded the following. Betulin had a slight growth inhibitory effect on alfalfa radicles. Betulin glycosides exhibited stronger effects than betulin, and betulin glycosides with two to four glucose residues as a sugar moiety had the greatest inhibitory activity. These characteristics of growth inhibitory effects were considerably different from those of phenolic compounds so far reported. Some betulin glycosides also showed a significant growth regulation effect on alfalfa hypocotyls. However, hypocotyl growth was less affected than radicle growth for all betulin glycosides. Among the triterpenoids, betulinic acid had stronger growth inhibitory effects on alfalfa radicles than betulin, suggesting the importance of the carboxyl group at the C-28 position for the inhibitory effects of lupane-type triterpenoids. On the other hand, no germination regulation effects on alfalfa seeds were observed for any of the betulin glycosides or triterpenoids examined. Received: October 9, 2001 / Accepted: February 15, 2002 Acknowledgments This work was supported in part by a research grant (Development of Highly Functional Materials by Structural Modification of Carbohydrates) from the Ministry of Agriculture, Forestry, and Fisheries of Japan. We thank Saori Kudo for her assistance in isolating compounds by chromatography. Correspondence to:S. Ohara     

Three triterpenoid saponins from the roots of Polygala japonica Houtt

Three new triterpenoid saponins polygalasaponins LI-LIII (1-3) with two acylation groups in oligosaccharide chain, together with three known saponins were isolated from the roots of Polygala japonica Houtt. (4-6). The neuroprotective effects of these compounds on neuron-like PC12 cells were evaluated in vitro. Compounds 5 and 6 show neuroprotective effects in Aβ(25-35) model at the concentration of 10μM.     

Two new hepaprotective saponins from Semen celosiae

Two new oleanolic acid saponins, namely celosin C (1) and celosin D (2), were isolated from the ethanol extract of Semen celosiae. Their structures were identified as celosin C (1) and celosin D (2) by spectroscopic and chemical analyses. The hepatoprotective activity of 1 and 2 with oral dose 1.0, 2.0 and 4.0 mg/kg, respectively, were investigated by carbon tetrachloride (CCl₄)-induced hepatotoxicity in mice. The results indicate that they have significant hepatoprotective effects (p < 0.01).     

Sibiricasaponins A–E,five new triterpenoid saponins from the aerial parts of Polygala sibirica L.

Five new triterpenoid saponins, named as sibiricasaponins A–E (1–5), were isolated and identified from the aerial parts of Polygala sibirica L., together with nine known triterpenoid saponins (6–14). The chemical structures of the five new triterpenoid saponins (1–5) were elucidated as 3β,19α-dihydroxyurso-12-ene-23,28-dioic acid 3-O-β-d-glucuronopyranoside (1), pomolic acid 3-O-(3-O-sulfo)-α-l-arabinopyranoside (2), pomolic acid 3-O-(4-O-sulfo)-β-d-xylopyranoside (3), pomolic acid 3-O-(2-O-acetyl-3-O-sulfo)-α-l-arabinopyranoside (4), and 3-O-β-d-glucopyranosyl medicagenic acid 28-O-β-d-galactopyranosyl (1 → 4)-β-d-xylopyranosyl (1 → 4)-α-l-rhamnopyranosyl (1 → 2)-(4-O-acetyl)-[β-d-apiofuranosyl (1 → 3)]-β-d-fucopyranosyl ester (5), respectively, on the basis of spectroscopic data and physicochemical evidences. These isolated compounds (1–14) were evaluated for their anti-ischemic effects on oxygen/glucose deprivation (OGD) model in vitro, and only compound 7 showed a weak anti-ischemia effect, with EC₅₀ value of 46.7 μM.     

Scopoletin suppresses pro-inflammatory cytokines and PGE2 from LPS-stimulated cell line, RAW 264.7 cells

Scopoletin (1-50 microg/ml) inhibited the release of PGE2, TNF-alpha, IL-1beta and IL-6 and suppressed the expression of COX-2 in a concentration-dependent manner. These results suggest that scopoletin might suppress the production of such pro-inflammatory cytokines and exert inhibitory activity on LPS-induced PGE2 production through the depression of COX-2 expression.     

The aphrodisiac and adaptogenic properties of ginseng

Ginseng is the root of the perennial herbs of Panax quinquefolium and Panax ginseng which contain a series of tetracyclic triterpenoid saponins (ginsenosides) as active ingredients. It is considered a tonic or adaptogenic that enhances physical performance (including sexual), promotes vitality and increases resistance to stress and ageing. The adaptogenic properties of ginseng are believed to be due to its effects on hypothalamic-pituitary-adrenal axis, resulting in elevated plasma corticotropin and corticosteroids levels. When used appropriately, ginseng appears to be safe. Nevertheless, documented side effects include hypertension, diarrhoea, restlessness, mastalgia and vaginal bleeding.     

Structure elucidation of two triterpenoid saponins from rhizome of Anemone raddeana Regel

Two new 27-hydroxy-oleanolic acid type triterpenoid saponins, raddeanoside 20 (1) and raddeanoside 21(2) were isolated from the rhizome of Anemone raddeana Regel. The structures of the two compounds were elucidated as 27-hydroxy-oleanolic acid 3-O-α-l-rhamnopyranosyl(1→2) [β-d-glucopyranosyl (1→4)]-α-l-arabinopyranoside (1) and 3-O-α-l-rhamnopyranosyl (1→2)-α-l-arabinopyranosyl-27-hydroxy-oleanolic acid 28-O-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl (1→6)-β-d-glucopyranoside (2) on the basis of chemical and spectral evidence.     

Caffeic and chlorogenic acids in Ilex paraguariensis extracts are the main inhibitors of AGE generation by methylglyoxal in model proteins

The present study concentrates on the evaluation of the anti-glycation effect of some bioactive substances present in yerba maté (Ilex paraguariensis): 5-caffeoylquinic acid, caffeic acid and a sapogenin (oleanolic acid). Bovine serum albumin and histones were incubated in the presence of methylglyoxal with or without the addition of 5-caffeoylquinic acid, caffeic acid and oleanolic acid. After the incubation period, advanced glycation end product (AGE) fluorescence spectra were performed and protein structural changes were evaluated by Sodium Dodecyl Sulfate Polyacrylamide Gel Electrophoresis. Chlorogenic acid, caffeic acid are the main substances responsible for the anti-glycation effect of maté tea.     

Antioxidative and acute antiinflammatory effects of Torreya grandis

The present study was undertaken to investigate the antioxidative and antiinflammatory activities of the ethanolic extract of seeds of Torreya grandis (EST). Exposure of human dermal fibroblasts to the extract at 50 and 250 microg/ml showed significant protective effect against hydrogen peroxide (300 microM). EST not only protected cell survival from H(2)O(2)-induced toxicity, but also inhibited the H(2)O(2)-induced LDH release significantly. It was also found that EST at 100 and 1000 microg/ml showed scavenging activities of radicals and reactive oxygen species with 29.8% and 100.0% of inhibition against DPPH radical and 41.2% and 98.4% against superoxide radicals in the xanthine/xanthine oxidase system, respectively. Topically applied EST dose-dependently inhibited arachidonic acid (AA)- and 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema in mice.     

New cytotoxic triterpenoid saponins from the whole plant of Clematis lasiandra Maxim

Four new oleanane type triterpenoid saponins (1–4) and three known saponins (5–7) were isolated from the whole plant of Clematis lasiandra Maxim. The structures of the four new compounds were elucidated as 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl hederagenin (1), 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl oleanolic acid 28-O-β-d-glucopyranosyl ester (2), 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl hederagenin (3) and 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-α-l-arabinopyranosyl hederagenin (4) on the basis of extensive spectroscopic analysis and chemical evidence. Compounds 1–7 were evaluated for their cytotoxicity against human tumor cell lines HL-60, Hep-G2 and SGC-7901, and all of the evaluated saponins showed significant cytotoxicity to those three tumor cell lines with IC₅₀ in the range from 1.40 to 19.50 μmol/L except for compounds 2 and 6.     

Oleanane glycosides from the leaves of Diploclisia glaucescens

Complete 1H and 13C NMR assignments are described for two known oleanane glycosides, 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyloleanolic acid and 3-O-beta-D-xylopyranosyl(1-->2)-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl oleanolic acid isolated from the methanol extract of the leaves of Diploclisia glaucescens.     

巴东皱皮木瓜发育及主要成分的变化分析

以湖北巴东产的皱皮木瓜为试验材料,分别在皱皮木瓜果实7个不同生长期采样,通过果实颜色、纵横径、鲜果质量等形态特征的测定,并采用HPLC法对不同生长期内的有效成分(齐墩果酸、熊果酸、原儿荼酸、绿原酸)进行检测,综合评价皱皮木瓜最佳的采收季节和质量指标.结果 表明:(1)皱皮木瓜的纵径、横径、鲜果质量增长随生长阶段呈逐渐递...     

Flavonoid-induced autophagy in hormone sensitive breast cancer cells

The activity of 8-prenylapigenin (8-PA) and its 3'-methoxylated analogue isocannflavin B (IsoB) was investigated in estrogen-dependent T47-D and estrogen-independent MDA-MB-231 human breast cancer cell lines. 8-PA showed a biphasic effect on T47-D cell proliferation, while no significant effect was observed on MDA-MB-231 cells. Conversely, IsoB exhibited only an inhibitory effect on T47-D cell proliferation, accompanied by the appearance of an intense intracytoplasmic vacuolization of autophagic origin. Moreover, biochemical analysis showed that IsoB reduced Akt phosphorylation and p21^Cip1 expression in T47-D cells. These data show that the prenylflavone moiety is a versatile platform for the induction and modulation of bioactivity.     

Antihyperglycemic and antioxidant activities of total alkaloids from Catharanthus roseus in streptozotocin-induced diabetic rats

We evaluated the hypoglycemic and antioxidant effects of the total alkaloids of leaves and twigs of Catharanthus roseus Linn.(CTA) in streptozotocin(STZ)-induced diabetic rats. The hypoglycemic effect was measured by blood glucose and plasma insulin level. Oxidative stress was measured in heart, liver and kidney by levels of antioxidant markers, free radical scavengers and lipid peroxides i.e. superoxide dismutase(SOD), catalase(CAT), glutathione(GSH) and thiobarbituric acid reactive substances(TBARS). Biochemical parameters, i.e. aspartate aminotransferase(AST), alanine aminotransferase(ALT), alkaline phosphate(ALP) were observed in diabetic control and treated rats. Oral administration of CTA for30 days was followed by a significant(P \ 0.05) decrease in fasting blood glucose and increase in insulin level as compared with untreated diabetic rats. Also it significantly(P \ 0.05) reduced ALT, AST and ALP. The treatment also resulted in significant(P \ 0.05) reductions in GSH,SOD, CAT, and decrease in TBARS in the heart, liver and kidney of diabetic rats. The results suggest that CTA can effectively normalize the impaired antioxidant status in STZ-induced diabetes in a dose-dependent manner.CTA exerted rapid protective effects against lipid peroxidation by scavenging of free radicals and reducing the risk of diabetic complications.     

A cytotoxic triterpenoid saponin from under-ground parts of Gypsophila pilulifera Boiss.& Heldr

A cytotoxic triterpenoid saponin was isolated from the under-ground parts of Gypsophila pilulifera Boiss.& Heldr. (Caryophyllaceae) naturally grow in the southwestern region of the Turkey. The structures of saponin was elucidated as 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→4]-α-l-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester on the basis of extensive spectral analysis and chemical evidence. The separated triterpenoid saponin was isolated from Gypsophila pilulifera for the first time. The saponin compound displayed significant cytotoxicity against A549 cell line with IC(50) values >16μM.