Response surface methodology-based optimization of ultrasound-assisted extraction of β-sitosterol and lupeol from astragalus atropilosus (roots) and validation by HPTLC method

Objective: To optimize the ultrasonication method for efficient extraction of P-sitosterol and lupeol from the roots of Astragalus atropilosus using Box-Behnken design of response surface methodology (RSM), and its validation by high performance thin layer chromatography (HPTLC) method. Methods: Ultrasonication method was used to extract β-sitosterol and lupeol from Astragalus atropilosus (roots). RSM was used to optimize the different extraction parameters viz. liquid to solid ratio (10-14 mL/g), temperature (60-80 °C) and time (40-60 min) to maximize the yield of β-sitosterol and lupeol. The quantitative estimation of β-sitosterol and lupeol was done in chloroform extract of Astragalus atropilosus by validated HPTLC method on 10 cm × 20 cm glass-backed silica gel 60F

Ethnopharmacological activity of Hedera nepalensis K. Koch extracts and lupeol against alloxan-induced type I diabetes

In this study, we investigated the protective effects of Hedera nepalensis crude extract, its fractions and lupeol in alloxan-induced diabetic rats. Lupeol and n-hexane (HNN) fraction significantly reduced the blood glucose level by increasing insulin level in time dependent manner, and also significantly increased amylase and lipase activity in diabetic rats. Elevated levels of alanine transaminases (ALT), aspartate transaminases (AST), thiobarbituric acid reactive substances (TBARS), nitrite, hydrogen peroxide (H2O2), total bilirubin and total protein in blood serum were efficiently restored to normal levels. Suppressed enzymatic activity of catalase (CAT), superoxide dismutase (SOD), reduced glutathione (GSH) and peroxidase (POD) were also restored to their normal levels. Kidney functions were also restored to normal level after treatment with HNN and lupeol. HNN fraction and lupeol of H. nepalensis prevented oxidative stress in alloxan-induced diabetic rats. This study signifies the importance of H. nepalensis and lupeol in ameliorating diabetes by inducing insulin secretion in diabetic model rats.

Chemical constituents from Rhynchosia volubilis / 中草药

Objective: To study the chemical constituents from Rhynchosia volubilis. Methods: The compounds were isolated and purified by a combination of various chromatographic techniques including silica gel, ODS, Toyopearl HW-40C, Sephadex LH-20, and semi-preparative HPLC chromatography. Their structures were identified by physicochemical properties and spectroscopic data. Results: Thirteen compounds were isolated from the petroleum ether extracts of R. volubilis and their structures were elucidated as (-)-sigmoidin E (1), lupinifolin (2), precatorin B (3), cajanone (4), sophoraisoflavanone B (5), 5,3’-dihydroxy-4’-methoxy-5’- γ,γ-dimethylallyl-2″,2″-dimethylpyrano [5,6:6,7] isoflavanone (6), genistein (7), licoisoflavone A (8), erylatissin B (9), neo-bavaisoflavone (10), lupeol (11), betulinic aldehyde (12), and clionasterol (13). Compounds 1-10 were all prenylated flavonoids, of which compounds 1-2 were dihydroflavones, compounds 3-6 were dihydroisoflavones, and compounds 7-10 were isoflavones. Compounds 11-12 were lupine triterpenoids, and compounds 13 was a sterol. Conclusion: Compounds 1, 5-6, 8-10, 12 and 13 are isolated from the genus for the first time, while compounds 1-3 and 5-13 are separated from this plant for the first time.

Enhancing effect of Lupeol on migration and invasion abilities of ST3Gaim-silenced MDA-MB-231 cells / 解剖学报

Objective In this study, we expored the enhancing effect of Lupeol on migration and invasion abilities of ST3Gal III-silenced MDA-MB-231 cells. Methods Human breast cancer cell line ST3Gal III -silenced MDA-MB-231 was cultured in vitro. The cell adhesion, Transwell and woud healing test were utilized to test the effect of Lupeol on ST3GalM-silenced MDA-MB-231 cells. The expression of matrix metalloproteinase( MMP)-2, -9, phosphatidylinositol 3-kinase/protein kinase B/nuclear factor κB ( PI3K/Akt/NF-KB) signaling pathway were examined by Western blotting. Results No significant influence of the decreased expression of ST3Gal III and Lupeol ( 5μmol/L) on proliferation and apoptosis of MDA-MB-231 cells were found. Lupeol inhibited the migration and invasion of ST3Gal III -silenced MDA-MB-231 cells in vilro( P<0. 05). Furthermore, the expression of NF-κB p65, p-Akt, Akt, p85, MMP-2 and MMP-9 levels were significantly down-regulated. Conclusion These observations suggest that Lupeol may inhibit the abilities of migration and invasion of ST3Gal III-silenced MDA-MB-231 cells in vitro by inhibiting the protein expression of MMP-2, -9 and effect the signaling pathway of PI3K/Akt/NF-κB.

Response surface methodology-based optimization of ultrasound-assisted extraction of β-sitosterol and lupeol from Astragalus atropilosus (roots) and validation by HPTLC method

Objective: To optimize the ultrasonication method for efficient extraction of β-sitosterol and lupeol from the roots of Astragalus atropilosus using Box-Behnken design of response surface methodology (RSM), and its validation by high performance thin layer chromatography (HPTLC) method.Methods: Ultrasonication method was used to extract β-sitosterol and lupeol from Astragalus atropilosus (roots). RSM was used to optimize the different extraction parameters viz. liquid to solid ratio (10–14 mL/g), temperature (60-80 ℃) and time (40–60 min) to maximize the yield of β-sitosterol and lupeol. The quantitative estimation of β-sitosterol and lupeol was done in chloroform extract of Astragalus atropilosus by validated HPTLC method on 10 cm × 20 cm glass-backed silica gel 60F254 plate using hexane and ethyl acetate (8:2, v/v) as mobile phase. Results: A quadratic polynomial model was found to be most appropriate with regard to R1 (yield of total extraction; R2/％ CV = 0.9948/0.28), R2 (β-sitosterol yield; R2/％ CV = 0.9923/0.39) and R3 (lupeol yield; R2/％ CV = 0.9942/0.97). The values of adjusted R2/predicted R2/signal to noise ratio for R1, R2, and R3 were 0.9782/0.9551/48.77, 0.9904/0.9110/31.33, and 0.9927/0.9401/36.08, respectively, indicating a high degree of correlation and adequate signal. The linear correlation plot between the predicted and experimental values for R1, R2, and R3 showed high values of R2 ranging from 0.9905-0.9973. β-sitosterol and lupeol in chloroform extract of Astragalus atropilosus were detected at Rf values of 0.22 and 0.34, respectively, at λ max = 518 nm. The optimized ultrasonic extraction produced 8.462％ w/w of R1, 0.451％ w/w of R2 and 0.172％ w/w of R3 at 13.5 mL/g liquid to solid ratio,78 ℃ of temperature and 60 min of time.Conclusions: The experimental findings of RSM optimized extraction and HPTLC analysis can be further applied for the efficient extraction of β-sitosterol and lupeol in other species of Astragalus.

Effect of lupeol on invasion and metastasis of human hepatoma HepG2 and SK-HEP-1 cells and its mechanism / 中国中药杂志

Epithelial-mesenchymal transformation(EMT) exists in embryonic development and is closely related to cell migration and invasion. The increased EMT level in tumors showed that E-cadherin was replaced by N-cadherin, and the expression of interstitial markers such as α-SMA and vimentin was up-regulated. It has been reported that lupeol can reduce the expression of matrix metalloproteinase-2(MMP-2), matrix metalloproteinase-9(MMP-9) and N-cadherin to inhibit the metastasis of osteoma cells. However lupeol has been less studied in liver cancer. Therefore, this paper investigated the effect of lupanol on invasion and metastasis of human hepatoma cell line HepG2 and SK-HEP-1 and its possible mechanism. MTT assay and Annexin V/PI double staining were used to investigate the effect of lupeol on activity and apoptosis of HepG2 cells and SK-HEP-1 cells. Moreover, the effect of lupeol on the invasion of HepG2 cells and SK-HEP-1 cells were evaluated by Transwell assay. The expressions of E-cadherin, N-cadherin, α-SMA, vimentin and MMP-9 were measured by Western blot. The model of subcutaneous transplantation of nude mice and the lung metastasis model of H22 hepatocellular carcinoma cells were established to evaluate the efficacy of lupeol in vivo on tumor growth and lung metastasis by HE staining combined with immunohistochemical assay. The results showed that lupeol inhibited the activity and invasion of HepG2 cells and SK-HEP-1 cells in a dose-dependent manner and induced apoptosis. Western blot showed that the expression of E-cadherin, a landmark protein for EMT, was induced by lupeol, and the expressions of N-cadherin, α-SMA, vimentin and MMP-9 were decreased. In vivo experiments showed that lupeol inhibited tumor growth in mice bearing xenograft. In addition, immunohistochemical experiments confirmed that lupeol could up-regulate the expression of E-cadherin in tumor tissues of nude mice, reduce the expression of N-cadherin, and inhibit the metastasis of liver cancer H22 cells in the lungs of mice. The above results indicated that the mechanism of lupeol inhibiting the invasion and metastasis of HCC cells may be related to the regulation of EMT process.

Antinociceptive and anti-inflammatory activities of a triterpene-rich fraction from Himatanthus drasticus

Himatanthus drasticus (Mart.) Plumel belongs to the Apocynaceae family and the latex from its trunk bark (Hd) is known as "janaguba milk". This latex is widely used in Northeast Brazil, mainly in the Cariri region, for its gastroprotective, anti-inflammatory, and antitumor properties. The objective of this study was to investigate a triterpene-rich fraction (FJNB) from H. drasticus latex on acute models of nociception and inflammation and to clarify its mechanisms of action. Wistar rats or Swiss mice were subjected to the carrageenan-induced paw edema test or the formalin test, respectively, after the acute oral treatment with FJNB. The inflamed paws from the carrageenan-induced paw edema and formalin tests were processed for histological and immunohistochemical assays, respectively. The results were analyzed by ANOVA and considered significant at P<0.05. FJNB (10 mg/kg) decreased the paw edema by 25% at the 3rd h after the carrageenan injection. Indomethacin, used as reference, inhibited the paw edema by 59% at the same time-point. In the formalin test, FJNB inhibited the 1st phase by 27, 49, and 52% and the 2nd phase by 37, 50, and 67%, at the doses of 1, 5, and 10 mg/kg, respectively. In addition, FJNB significantly inhibited the expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and the inflammatory cytokine tumor necrosis factor (TNF)-alpha. The histone deacetylase (HDAC) expression and the transcription factor nuclear factor kappa (NF-kB) were also inhibited at the same doses. In conclusion, the FJNB inhibitory actions on iNOS, COX-2, TNF-α, HDAC, and NF-kB could be involved with the drug anti-inflammatory activity.

Non-polysaccharide chemical constituents of Poria cocos and their anti-complementary activity / 中草药

Objective: To investigate the non-polysaccharide chemical constituents of Poria cocos and their anti-complementary activity. Methods: The anti-complementary bioassay-guided isolation was carried out with the hemolysis test as guide. All isolates were evaluated for their in vitro anti-complementary activities on the classical pathway. The structures were identified by various spectroscopic data including ESI-MS, 1H-NMR, and 13C-NMR data. Results: Eleven compounds were isolated from the EtOAc fraction of P. cocos extracts, including stigmasterol (1), lupeol (2), oleanolic acid (3), ursolic acid (4), polyporenic acid C (5), tumulosic acid (6), dehydrotumulosic acid (7), 3-epi-dehydrotumulosic acid (8), pachymic acid (9), dehydropachymic acid (10), and dehydrotrametenolic acid (11). Compounds 1-4 were obtained from this plant for the first time, and compounds 3-11 showed the anti-complementary activity in different degrees. Conclusion: Triterpenoid acids are the main anti-complementary constituents in the chemical constituents of P. cocos non-polysaccharides (CH50 0.10-0.27 g/L).

Study on the Inhibitory Effects of Lupeol on the Proliferation of Human Breast Cancer MCF- 7 Cells by MAPKs Signaling Pathway / 中国药房

OBJECTIVE： To investigate inhibitory effects of lupeol on the proliferation of human breast cancer MCF-7 cells and its possible mechanism. METHODS： Taking MCF-7 cells as research object， MTT assay was used to detect the proliferation of MCF-7 cells after treated with different doses of lupeol （7.5， 15， 30， 60， 90 mg/L） for 24 h. Survival rate and IC50 of MCF-7 cells were calculated. The inverted microscope and cell cloning experiment were used to observe and detect the morphological characteristics of MCF-7 cells and clonal colony formation after treated with different doses of lupeol （15， 30， 60 mg/L） for 24 h. The rate of clonal colony formation was calculated. MTT method and Western blotting assay were used to detect the proliferation of MCF-7 cells and the expression of related regulatory proteins （ERK1/2， p-ERK1/2， JNK， p-JNK， p38 MAPK， p-p38 MAPK） after additionally treated with MAPKs signaling pathway-related regulation protein inhibitors PD98059， SP600125 and SB203580. RESULTS： After treated with 15， 30， 60， 90 mg/L lupeol， survival rates of MCF-7 cells were decreased significantly （P＜0.05 or P＜0.01）. IC50 value of the compound was 52.94 mg/L. After treated with 15， 30， 60 mg/L lupeol， the morphological characteristics of cells in each group changed， and the phenomena of cell exfoliation， floating， solid shrinkage， roundness， volume reduction and necrosis were observed. The formation of clonal colony decreased and the rate of clonal colony formation decreased significantly （P＜0.05 or P＜0.01）. When lupeol used alone， compared with control group， survival rate （60 mg/L lupeol）of MCF-7 cells was decreased significantly； the expression of p-ERK1/2 （15， 30， 60 mg/L lupeol）， p-JNK （30， 60 mg/L lupeol） and p-p38 MAPK （30， 60 mg/L lupeol） were increased significantly （P＜0.05 or P＜0.01）. After additional use of relevant inhibitors， compared with 60 mg/L lupeol group， survival rates of MCF-7 cells in combination groups were increased significantly， while relative expression of p-ERK1/2， p-JNK and p-p38 MAPK were decreased significantly （P＜0.05 or P＜0.01）. CONCLUSIONS： Lupeol can inhibit the proliferation of human breast cancer MCF-7 cells， the mechanism of which may be related to the phosphorylation of MAPKs signaling pathway-related regulatory proteins.

Lupeol and its esters: NMR, powder XRD data and in vitro evaluation of cancer cell growth

ABSTRACT The triterpene lupeol (1) and some of its esters are secondary metabolites produced by species of Celastraceae family, which have being associated with cytotoxic activity. We report herein the isolation of 1, the semi-synthesis of eight lupeol esters and the evaluation of their in vitro activity against nine strains of cancer cells. The reaction of carboxylic acids with 1 and DIC/DMAP was used to obtain lupeol stearate (2), lupeol palmitate (3) lupeol miristate (4), and the new esters lupeol laurate (5), lupeol caprate (6), lupeol caprilate (7), lupeol caproate (8) and lupeol 3',4'-dimethoxybenzoate (9), with high yields. Compounds 1-9 were identified using FT-IR, 1H, 13C-NMR, CHN analysis and XRD data and were tested in vitro for proliferation of human cancer cell activity. In these assays, lupeol was inactive (GI50> 250µg/mL) while lupeol esters 2 -4 and 7 - 9 showed a cytostatic effect. The XRD method was a suitable tool to determine the structure of lupeol and its esters in solid state. Compound 3 showed a selective growth inhibition effect on erythromyeloblastoid leukemia (K-562) cells in a concentration-dependent way. Lupeol esters 4 and 9 showed a selective cytostatic effect with low GI50 values representing promising prototypes for the development of new anticancer drugs.

Chemical constituents of petroleum ether soluble part from whole herbs of Mulgedium tataricum / 中草药

Objective: To isolate and identify the chemical constituents of petroleum ether soluble part of 60% aq. ethanol extracts from the whole herb of Mulgedium tataricum. Methods: Separation and purification were performed on silica gel column chromatography and recrystallization, PTLC, PHPLC, and related techniques. Their chemical structures were elucidated through spectroscopic analyses (NMR). Results: Nine compounds were isolated and identified as taraxasterol (1), pseudotaraxasterol (2), lupeol (3), olean-18-en-3β-ol (4), β-sitosterol (5), olean-18-en-3-one (6), 3β-hydroxy-taraxaster-20(30)-ene-28-oic acid (7), stigmasterol (8), and lupenone (9), respectively. Conclusion: Compounds 3, 4, 6, 7, and 9 are separated from this plant for the first time.

Comparative molecular docking studies of lupeol and lupenone isolated from Pueraria lobata that inhibits BACE1: Probable remedies for Alzheimer's disease

Objective To discover lead lupane triterpenoid's potential isolated from Pueraria lobata roots against β-site amyloid precursor protein cleaving enzyme 1 (BACE1), which serve as a rate limiting step in amyloid beta (Aβ) production altering the course of Alzheimer's disease. In addition, enzyme kinetics study and molecular docking were conducted to establish the inhibition type and structure activity relationship. Methods A systematic study of 70% ethanolic P. lobata root extract was employed to identify its BACE1 inhibitory potential. Further, BACE1 inhibitory potential of two lupane terpenoids, yielded from ethanolic extract, was assessed. In order to determine their inhibition mode, Lineweaver–Burk plots and Michaelis–Menten model for BACE1 was performed. AutoDock 4.2 program in addition determined the molecular interaction of BACE1 with isolated terpenoids. Results Considering the inhibitory potential of 70% ethanolic extract of P. lobata against BACE1 (IC

Comparative molecular docking studies of lupeol and lupenone isolated from Pueraria lobata that inhibits BACE1: Probable remedies for Alzheimer's disease

OBJECTIVE@#To discover lead lupane triterpenoid's potential isolated from Pueraria lobata roots against β-site amyloid precursor protein cleaving enzyme 1 (BACE1), which serve as a rate limiting step in amyloid beta (Aβ) production altering the course of Alzheimer's disease. In addition, enzyme kinetics study and molecular docking were conducted to establish the inhibition type and structure activity relationship.@*METHODS@#A systematic study of 70% ethanolic P. lobata root extract was employed to identify its BACE1 inhibitory potential. Further, BACE1 inhibitory potential of two lupane terpenoids, yielded from ethanolic extract, was assessed. In order to determine their inhibition mode, Lineweaver-Burk plots and Michaelis-Menten model for BACE1 was performed. AutoDock 4.2 program in addition determined the molecular interaction of BACE1 with isolated terpenoids.@*RESULTS@#Considering the inhibitory potential of 70% ethanolic extract of P. lobata against BACE1 (IC = 80.35 μg/mL), lupeol and lupenone were subsequently isolated and exhibited notable or moderate BACE1 inhibitory activity with IC values of 5.12 and 62.98 μmol/L, respectively, as compared to the positive control quercetin (IC = 21.28 μmol/L). The enzyme kinetics study enabled us to identify both compounds as competitive inhibitors, where lupeol displayed a very potent inhibition against BACE1 with low inhibition constant (K) value of 1.43 μmol/L, signifying greater binding affinity. In order to understand the binding mechanism and structure-activity relationship of two triterpene-based BACE1 inhibitors, we employed computer aided docking studies which evidently revealed that hydroxyl group of lupeol formed two hydrogen bonds with the ASP32 (catalytic aspartic residue) and SER35 residues of BACE1 with the binding energy of (-8.2 kcal/mol), while the ketone group of lupenone did not form any hydrogen bonds with BACE1 giving evidence for less binding affinity. These results in turn have predicted the dependence of the inhibitory activity in the presence of hydroxyl group which has provided a new basis for BACE1 blockade.@*CONCLUSIONS@#Our results have successfully explored the molecular mechanism of lupane triterpenoids via BACE1 inhibition, suggesting that lupeol in particular could be utilized as a useful therapeutic and preventive agent to mitigate Alzheimer's disease.

Triterpenes and sterols from Hoya diversifolia Blume.

Chemical investigation of the dichloromethane extracts of Hoya diversifolia Blume led to the isolation of β-amyrin cinnamate (1), squalene (2), β-sitosterol (3), a mixture of β-amyrin (4a), α-amyrin (4b) and lupeol (4c) in a 4:2:1 ratio and saturated hydrocarbons from the leaves; and 2, taraxerol (5), lupeol cinnamate (6), and a mixture of 3 and stigmasterol (7) in a 2:1 ratio from the stems. The structures of 1-7 were identified by comparison of their NMR data with those reported in the literature.

Studies on chemical constituents from Artabotrys pilosus / 中草药

Objective: To study the chemical constituents from twigs and leaves of Artabotrys pilosus. Methods: The chemical constituents of A. pilosus were separated and purified by silica gel, ODS, Sephadex LH-20 gel column chromatographies, and preparative HPLC. Their structures were determined by physicochemical properties, spectral data, as well as comparisons with the data in literature. Results: Sixteen compounds were isolated from the acetic ether fraction of 90% ethanol extract from the twigs and leaves of A. pilosus, and identified as dammaradienylacetate (1), lupeol (2), lupenyl acetate (3), betulinic acid (4), uvaol (5), ursolic acid (6), β-amyrin (7), erythrodiol (8), friedelinol (9), friedelin (10), α-spinasterone (11), stigmast-7-ene-3β-ol (12), stigmast-5-ene-3β-ol-7-one (13), stigmastan-3,6-diketone (14), stigmasterol (15), and β-sitosterol (16). Conclusion: All compounds are isolated from A. pilosus for the first time. Except for compounds 15 and 16, other compounds are isolated from the plants of Artabotrys R. Br. for the first time.

Effect of lupeol on migration and invasion of human breast cancer MDA-MB-231 cells and its mechanism / 药学学报

In this study, we examined the inhibitory effects of lupeol, an extract of Euphorbia fischerana Steud, on human breast cancer MDA-MB-231 cells migration and invasion. Lupeol was found to inhibit the invasion of MDA-MB-231 in the cell adhesion assay, transwell test and wound healing assay. The expression of cyclooxygenase-2(COX-2), matrix metalloproteinase-2(MMP-2), -9(MMP-9) and nuclear transcription factor-kappa B (NF-κB) p65 in breast cancer following treatment with different concentrations of lupeol was analyzed with Western blot. Lupeol inhibited the migration and invasion of MDA-MB-231 cells in a dosedependent manner in vitro (PκB p65 levels was significantly down-regulated. These observations suggest that lupeol can inhibit the abilities of invasion of MDA-MB-231 cells by inhibiting the protein expression of COX-2, MMP-2 and MMP-9. Its mechanism may be related to inhibition of the nuclear NF-κB signal pathway.

Construction of cell factories for production of lupeol in Saccharomyces cerevisiae / 中国中药杂志

Lupane-type triterpenoids, such as betulinic acid, are derived from lupeol and have excellent properties in anti-HIV, anti-cancer activities and so on. For realizing heterogenous production of lupane-type triterpenoids, our research firstly integrated all the seven genes in the MVA pathway in Saccharomyces cerevisiae to increase the supply of squalene (triterpenoids universal precursor) in a single step using the DNA assembler method. Next, cell factories for production of lupeol was constructed by integrating Arabidopsis thaliana lupeol synthetic gene (AtLUP) into chromosome of triterpenoid chassis strain. Results showed that the MVA pathway, about 20 kb nucleotide length, could be assembled in one-pot process and the doubled MVA pathway could significantly improve squalene by 500-fold, reaching 354.00 mg•L⁻¹. NK2-LUP was obtained by introducing AtLUP gene on chromosome, and could produce 8.23 mg•L⁻¹ lupeol. This study supports the possibility of large-scale biosynthetic pathway assembly in S.cerevisiae and lays the foundation of obtaining cell factories for production of lupan-type triterpenoids at the same time.

Anti-proliferative Effect of Lupeol on Human Bladder Cancer T24 Cell Line via p53/miR-34 a Signaling / 中国药师

Objective:To study the anti-proliferative effect of lupeol on human bladder cancer T24 cell line and the regulating mechanism for p53/miR-34a signaling. Methods:CCK-8 assay was performed to evaluate the effects of lupeol at different concentra-tions on cell viability in 24 h and 48 h. Caspase inhibitors were used to identify the subtypes of Caspase during lupeol induced cell death. The effects of lupeol on the expression of total p53 protein and miR-34a were evaluated by western blot and real-time PCR, re-spectively. The effects of lupeol on downstream targets of miR-34a were quantified by real-time PCR. Results:Lupeol could inhibit the proliferation of T24 cells in a dose-dependent manner. The IC50 of lupeol was (77. 23 ± 6. 78) μmol·L-1 in 24 h. Compared with the control group, lupeol could elevate the expressions of p53 and miR-34a (P<0. 01). Moreover, the mRNA expression of miR-34a tar-gets, Bcl-2, CD44 and c-Myc were significantly down-regulated after the treatment with lupeol (P<0. 01). Conclusion:Lupeol can inhibit T24 cell proliferation, which is related with the regulating effects on p53/miR-34a signaling.

Chemical Constituents of Ixora philippinensis Merr.

Chemical investigations of the dichloromethane extracts of Ixora philippinensis Merr., a plant endemic to the Philippines, led to the isolation of syringaresinol (1), pinoresinol (2), isoscopoletin (3), squalene (4), β-sitosterol (5a), and stigmasterol (5b) from the stems; and 4, 5a, 5b, lupeol (6), and lutein (7) from the leaves. The structures of 1 and 3 were elucidated by extensive 1D and 2D NMR spectroscopy, while those of 2 and 4-7 were identified by comparison of their NMR data with literature data.

Triterpenes and Acylglycerols from Canarium ovatum.

Chemical investigations of the dichloromethane extracts of the leaves of Canarium ovatum Engl. afforded β- amyrin (1a), α-amyrin (1b), epi-β-amyrin (2a), epi-α-amyrin (2b), epi-lupeol (2c), β-carotene (3) and lutein (4); while the twigs yielded 1a-1b. The dichloromethane extracts of the fruits of C. ovatum yielded triacylglycerols (5); the mesocarp also afforded 1a, 1b, 1,2-dioleylglycerol (6), and monounsaturated and saturated fatty acids; the nutshell also provided 6; and the kernel also yielded monounsaturated and saturated fatty acids. The structures of 1-6 and the fatty acids were identified by comparison of their 1H and/or 13C NMR data with those reported in the literature.