Long-chain alkanoic acid esters of lupeol from Dorstenia harmsiana Engl. (Moraceae)

In addition to lupeol (1a), three long-chain alkanoic acid esters of lupeol, in which two were new, were isolated from the hexane and ethyl acetate twigs extract of Dorstenia harmsiana Engl. (Moraceae). The structures of the new compounds were elucidated on the basis of 1D and 2D NMR experiments. Some isolated compounds were evaluated for their antimicrobial activities. The lupeol and its three long-chain alkanoic acid esters showed antifungal and antibacterial activities.     

A bioactive spirolactone iridoid and triterpenoids from Himatanthus sucuuba.

Himatanthus sucuuba is an Amazonian tree with abundant, yet conflicting ethnobotanical information. Investigation of the polar and non-polar constituents led to the isolation of plumericin, a bioactive spirolactone iridoid, and four known pentacylic triterpenes: lupeol acetate, lupeol cinnamate, lupeol beta-phenyl propionate, and alpha-amyrin cinnamate.     

Novel class of hybrid natural products derived from lupeol as antimalarial agents

Thirty-four novel hybrid lupeol derivatives (4-18) were prepared and evaluated for antimalarial activity in vitro against Plasmodium falciparum. Three compounds (13d, 16a and 17a) have shown antimalarial activity at lower dose (10 microg mL(-1)) than lupeol.     

Studies on the synthesis of biomarkers: V. Synthesis of γ-lupane and its epimer

γ-Lupane ( 2 ) and iso-γ lupane ( 10 ) (3α-isopropyl, 5αH) were synthesized from lupeol. The reaction conditions of conversion of lupeol into lupenes and γ-lupenes and the results of catalytic hydrogenation of lupenes and γ-lupenes under different conditions were studied.     

细胞代谢组学用于羽扇豆醇干预人乳腺癌细胞MCF-7的机理探究

应用基于气相色谱-质谱联用（GC-MS）的代谢组学方法结合细胞周期实验,研究羽扇豆醇体外抑制人乳腺癌细胞MCF-7增殖的作用机理。代谢组学的研究结果表明：通过正交偏最小方差判别分析（OPLS-DA）可以很好地区分羽扇豆醇作用的MCF-7细胞代谢谱与对照组细胞代谢谱,模型参数为：R²Ycum=0.988,Q²Ycum=0.964。VIP（variable importance in the projection）值大于1的差异代谢物进一步用t检验进行单位分析,选择t<0.05（VIP>1）的代谢物作为羽扇豆醇作用组的生物标志物,得到琥珀酸、磷酸、亮氨酸、异亮氨酸等11种代谢差异物。结合羽扇豆醇将细胞周期抑制在G1期这一现象,推测羽扇豆醇可能是主要抑制了三羧酸循环中的琥珀酰辅酶A的生成和底物磷酸化生成ATP的反应来抑制MCF-7细胞的增殖。本实验从代谢组学角度为乳腺癌抗肿瘤机制提供新的线索。     

Inhibitory Effect of Lupeol on MMPs Expression using Aged Fibroblast through Repeated UVA Irradiation

In this study, the aged dermal fibroblast model was constructed by repeated irradiation with UV light and the effect of lupeol, a triterpenoid, on anti‐aging was confirmed. SA‐β‐galactosidase (SA‐β‐gal) stained aged cells increased by about 40% and expression of p‐p53, p21, p16 and MMPs (MMP‐1, ‐2, ‐3) increased in aged fibroblast. As an efficacy result, the treatment of lupeol on aged fibroblast induced by UVA repeated irradiation showed a dose‐dependent reduction of SA‐β‐gal stained aged cells, the expression of p‐p53, p21, p16 and inhibition of MMPs. Interestingly, lupeol increased dephosphorylation of p‐ERK in repeated UV irradiated conditions. Additionally, lupeol compensated MMPs expression when p‐ERK phosphorylation was inhibited by p‐ERK inhibitor PD98059. Thus, these results showed that lupeol has a possible effect on MMPs expression using inhibition of the p‐ERK pathway. Taken together, we confirmed that lupeol inhibits senescence through inhibiting MMP‐1, ‐2, ‐3 as well as p‐p53, p21 and p16 expression and SA‐β‐gal activity in repeated UVA‐irradiated senescent FB models, therefore suggesting that lupeol may be useful as an anti‐aging agent.     

New cycloartenol esters from Ixora coccinea

The air-dried flowers of Ixora coccinea L. afforded two new cycloartenol esters (1a and 1b), lupeol fatty ester, lupeol, ursolic acid, oleanolic acid, and sitosterol. The structures of 1a and 1b were elucidated by extensive 1D and 2D NMR spectroscopy and MS.     

Investigation of antiplasmodial efficacy of lupeol and ursolic acid isolated from Ficus benjamina leaves extract

Abstract

This study emphasizes on the investigation of antiplasmodial activity of triterpenoids isolated from Ficus benjamina leaves. An unsaponified fraction of petroleum ether extract of plant leaves was subjected to silica gel column chromatography which led to the isolation of two known triterpenoids; namely ursolic acid and lupeol. These compounds were evaluated for antiplasmodial activity by schizont maturation inhibition assay using 3D7 Plasmodium strains. Both, ursolic acid and lupeol were found to exhibit significant antiplasmodial effect with an IC₅₀ value of 18?µg/ml and 3.8?µg/ml, respectively. This study further confirms the traditional role of Ficus benjamina plant in the treatment of malaria which may be attributed to ursolic acid and lupeol.     

A new triterpenoid ester from the fruits of Bruguiera parviflora

A new lupane caffeoyl ester (1), 3-(Z)-caffeoyllupeol, together with five known triterpenoids, lupeol caffeate (2), 3-(Z)-coumaroyllupeol (3), dioslupecin A (4), lupeol (5), and lupenone (6), were isolated from the fruits of Bruguiera parviflora. Their structures were elucidated by spectroscopic methods. Compound 1 exhibited antimalarial activity with an EC50 value of 8.6 microg/ml, but compound 2 was inactive.     

Bowdenol, a new 2,3-dihydrobenzofuran constituent from Bowdichia virgilioides

From the stem bark of Bowdichia virgilioides, lupeol, lupeol acetate, sitosterol, stigmasterol and methyl-3-[2-(1-hydroxymethylvinyl)-2,3-dihydrobenzo[b]furan-5-yl]-(E)-2-propenoate have been isolated. The latter is a new compound and it has been named as bowdenol. Their structures were elucidated with the aid of spectroscopic techniques, mostly 1 and 2D NMR. The biogenetic pathway for bowdenol has been suggested.     

Tyrosinase inhibitory potential of natural products isolated from various medicinal plants

Seven secondary metabolites, p-hydroxybenzoic acid (1), 3,4-dihydroxybenzoic acid (2), ferulic acid (3), 2,6-dimethoxy-4-hydroxy acetophenone (4), lupeol (5), 2'-O-ethylmurrangatin (6) and hibiscetin heptamethyl ether (7) were the natural products isolated from various medicinal plants. Their structures were identified by spectral comparison with previously reported data. The compounds 1-7 were screened for their tyrosinase-inhibitory activity. The compound p-hydroxybenzoic acid (1) was found to have potent activity against tyrosinase enzyme, whereas lupeol (5) showed significant activity.     

Thermal Behaviour of Some Terpenoids

The terpenoids acetyl sitosterol, lupeol, acetyl diosgenin and stigmasterol were studied. Comparison of the thermogravimetric curves and the activation energies of the terpenoids suggested the following sequence of thermal stability: acetyl sitosterol < acetyl diosgenin < lupeol < stigmasterol. The DSC curves allowed determination of the melting points and the degrees of purity. Comparison of the TG and DSC curves revealed the presence of phase transitions without mass loss that were attributed to rearrangements in the terpenoid molecules. This revised version was published online in August 2006 with corrections to the Cover Date.     

Isolation and TLC Densitometric Quantification of Gallicin, Gallic Acid, Lupeol and β-Sitosterol from Bergia suffruticosa, a Hitherto Unexplored Plant

Bergia suffruticosa (Elatinaceae family) is an important Indian medicinal plant hitherto unexplored for its chemical constituents and its pharmacological activity. In the present paper we report our work on isolation of gallicin, gallic acid, lupeol and β-sitosterol from the plant. To the best of our knowledge, this is the first report of these four compounds from this plant. Further, these four marker compounds were quantified by thin layer chromatography densitometric methods using high performance thin layer chromatography. The thin layer chromatography densitometric methods were found to be precise with RSD for intra-day in the range of 0.61–1.83, 1.14–1.57, 0.38–0.52 and 0.15–0.52 and for inter-day in the range of 0.97–1.45, 0.58–1.27, 0.42–0.50 and 0.26–0.61 for different concentrations of gallicin, gallic acid, lupeol and β-sitosterol. Instrumental precision was 1.05, 1.20, 0.65 and 0.85 (% RSD) for gallicin, gallic acid, lupeol and β-sitosterol. Accuracy of the method was checked by conducting recovery studies at three different levels for the four compounds and the average percentage recoveries obtained were 99.89, 100.58, 99.79 and 100.11%. B. suffruticosa sample was found to contain 0.34% w/w of gallicin, 0.288% w/w of gallic acid, 0.064% w/w of lupeol and 0.034% w/w of β-sitosterol.     

Separation and identification of some common isomeric plant triterpenoids by thin-layer chromatography and high-performance liquid chromatography

Chromatographic separation of 10 triterpenoids (α-amyrin, β-amyrin, δ-amyrin, lupeol, lupenon, lupeol acetate, cycloartenol, cycloartenol acetate, ursolic acid, oleanolic acid) and 2 sterols (stigmasterol and β-sitosterol) was studied. The chromatographic techniques included silica gel and reversed-phase (C₁₈ RP) thin-layer chromatography (TLC) and C₁₈ RP high-performance liquid chromatography (HPLC) using UV and mass spectrometric (MS) detection with atmospheric pressure chemical ionization (APCI). The TLC separation of the isomeric triterpenols lupeol, α-amyrin, β-amyrin and cycloartenol was achieved for the first time using C₁₈ RP-HPTLC plates. Cycloartenol could be separated from related compounds only on C₁₈ RP-TLC but not on the C₁₈ RP-HPLC. δ-Amyrin isolated from the tomato fruit surface extract could be separated from other amyrins only by HPLC. Tandem mass spectrometry allowed discrimination between the isomers lupeol, α-amyrin, β-amyrin, δ-amyrin, cycloartenol and between lupeol acetate and cycloartenol acetate. The combination of 3 TLC methods and 2 HPLC methods enables qualitative determination of all 12 compounds and proves to be useful for the analysis of plant extracts. It is recommended that TLC screening on silica gel and C₁₈ RP be performed before HPLC analysis.     

Synthesis and in vitro antitumour activities of lupeol derivatives

Nine lupeol derivatives were synthesised and assayed in vitro for their antitumour activities against three human tumour cells lines, A549, LAC and HepG2. Of lupeol derivaties, six were new compounds, and five compounds against A549 cells, four compounds against HepG2 cells and three compounds against LAC cells were effective in reducing viability, and the most promising compounds 5, 6 and 9 exhibited high activities against lung and liver cancer cells, even higher activities than those of adriamycin.     

Concurrent quantification of oleanolic acid, β-sitosterol and lupeol by a validated high-performance thin-layer chromatography method in Urginea indica Kunth bulb

A validated high-performance thin-layer chromatography (HPTLC) method was developed for the simultaneous quantification of oleanolic acid, β-sitosterol and lupeol in the bulb of Urginea indica Kunth. Separation of metabolites was done in mobile phase using toluene‒ethyl acetate‒methanol‒acetone (7:2:0.2:0.2, V/V) and quantification was done after derivatization by dipping in aninsaldehyde‒sulphuric acid; densitometric scan was performed at 530 nm. The proposed method for quantification was linearly calibrated in the range of 200‒1000 ng/spot for oleanolic acid and β-sitosterol; 100‒500 ng/spot for lupeol, and it was found specific and repeatable. The R_F values were found at 0.44 ± 0.03, 0.55 ± 0.05 and 0.68 ± 0.08, limit of detection and limit of quantification were 1.045, 0.524, 0.525 µg/spot and 3.167, 1.588, 1.592 µg/spot for oleanolic acid, β-sitosterol and lupeol, respectively. Precision and recovery study for sample and standards were within the limit of the International Council for Harmonization guidelines. Oleanolic acid, β-sitosterol and lupeol were found to be 0.113%, 0.105% and 0.036%, respectively, in methanolic extract of plant on dry weight basis. This study will help in checking routine quality control of herbal drugs as well as herbal formulations containing U. indica.

     

Absorption and distribution of lupeol in CD‐1 mice evaluated by UPLC–APCI+–MS/MS

Lupeol is a dietary triterpene that shows limited water solubility, which affects its bioavailability. It is well known that poor oral bioavailability is one of the major causes of therapeutic variability. Lupeol has been reported to have multiple biological activities; however, there are no reports about its bioavailability. Therefore, the objective of this research was to evaluate the systemic bioavailability of lupeol. An experimental strategy with three groups of female CD‐1 strain mice was proposed (control, olive oil and lupeol in olive oil), at six experimental times (0.5, 2, 4, 8, 12 and 24 h) with four animals per experimental point. Mice were sacrificed for organs, urine, feces and blood collection. Lupeol was extracted from samples and analyzed by UPLC–APCI⁺–MS/MS, obtaining the pharmacokinetics parameters time to peak concentration 6.444 ± 0.851 h and peak concentration 8.071 ± 2.930 μg/mL. Study of direct digestion and absorption in various organs showed important concentrations of lupeol at earlier post‐administration times (stomach, 137.25 ± 19.94 ng/mg and small intestine, 99.00 ± 12.99 ng/mg). The main excretion route was fecal, with a peak at 12 h post‐administration (163.28 ± 9.83 μg/mg). Absorption of lupeol by the animals was better than expected despite its nonpolar nature (extent of absorption F = 0.645 ± 0.0581).     

New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana

Chromatographic separation ofn-hexane and ethyl acetate fraction of a crude methanol extract obtained from aerial parts of theScorzonera aucherianaDC collected from Sivas province of Turkey yielded nine natural compounds; two new 3-caffeoyl-quinic acid analogs (1-2), one new taraxasterol oleate (3), and six known triterpenoids taraxasterol (4), taraxasterol acetate (5), ptiloepoxide (6), lupeol (7), lupeol acetate (8), andβ-sitosterol (9) were characterized. The structures of the isolated compounds were elucidated on the basis of NMR (¹H,¹³C, COSY, HMBC, HSQC, and TOCSY), UV, FT-IR and LC-Q-TOF-MS spectrometric data.     

New constituents from Mikania laevigata Shultz Bip. ex Baker

A new phenylpropanoid and two new diterpenes were isolated from the leaves of the plant Mikania laevigata Shultz Bip. ex Baker. The structures of these compounds were established by 1D- and 2D-nuclear magnetic resonance spectroscopic techniques and mass spectrometry data. Taraxerol, lupeol, coumarin, syringaldehyde, trans-melilotoside, cis-melilotoside, adenosine, patuletin 3-O-β-d-glucopyranoside, kaempferol 3-O-β-d-glucopyranoside, quercetin 3-O-β-d-glucopyranoside, methyl 3,5-di-O-caffeoyl quinate, and 3,3′,5-trihydroxy-4′,6,7-trimethoxyflavone were isolated too. In addition, the compounds dihydrocoumarin, spathulenol, caryophyllene oxide, kaurenoic acid, beyerenoic acid, and lupeol acetate were identified by GC-MS.