Flavaglines and triterpenoids from the leaves of Aglaia forbesii

Three structurally complex flavaglines of the cyclopenta[bc]benzopyran type, named desacetylpyramidaglains A, C, D (1-3), and the triterpene 23, 24, 25-trihydroxycycloartan-3-one (4) were isolated from the leaves of Aglaia forbesii together with the two rare pregnane steroids 2beta,3beta-dihydroxy-5alpha-pregn-17(Z)-en-16-one and 2beta,3beta-dihydroxy-5alpha-pregn-17(E)-en-16-one, as well as the bisamide pyramidatine, the sesquiterpene spathulenol, and the widespread triterpenoids lupeol, lupenone, and a mixture of beta-sitosterol and stigmasterol. Their structures were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. Compounds 3, 4, 5, and 6 were tested for antituberculosis and antiviral activity.     

Dolabellane diterpenoids from Aglaia odorata

Dolabellane diterpenoids, (1R,3E,7E,10S,11S,12R)-dolabella-3,7-dien-10,18-diol (1), (1R,3S,7E,11S,12R)-dolabella-4(16),7-dien-3,18-diol (2), (1R,7E,11S,12R)-18-hydroxydolabella-4(16),7-dien-3-one (3), (1R,3S,4S,7E,11S,12R)-3,4-epoxydolabella-7-en-18-ol (4), and (1R,3R,7E,11S,12R)-dolabella-4(16),7,18-trien-3-ol (5), were obtained from the ornamental plant Aglaia odorata. Their structures were characterized on the basis of spectroscopic analyses and further confirmed by X-ray diffraction. Compounds 1 and 5 showed weak cytotoxicity against the human myeloid leukemia HL-60, hepatocellular carcinoma SMMC-7721, and lung cancer A-549 cells.     

Diterpenoids and triterpenoids from Euphorbia guyoniana

Two new compounds with tigliane and cycloartane skeletons: 4,12-dideoxy(4alpha)phorbol-13-hexadecanoate (1) and 24-methylenecycloartane-3,28-diol (2), respectively, in addition of four known diterpenoids and 13 triterpenoids: 3-benzoyloxy-5,15-diacetoxy-9,14-dioxojatropha-6(17),11-diene (4), ent-abieta-8(14),13(15)-dien-16,12-olide (5), ent-8alpha,14alpha-epoxyabieta-11,13(15)-dien-16,12-olide (6), ent-3-hydroxyatis-16(17)-ene-2,14-dione (7), 3beta-hydroxytaraxer-14-en-28-oic acid (8), beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate (9), multiflorenyl acetate (10), multiflorenyl palmitate (11), peplusol (12), 24-methylenecycloartanol (3), lanosterol (13), euferol (14), butyrospermol (15), cycloartenol (16), obtusifoliol (17), cycloeucalenol (18) and beta-sitosterol (19), were isolated from the roots of Euphorbia guyoniana. Their structures were established on the basis of physical and spectroscopic analysis, including 1D and 2D homo- and heteronuclear NMR experiments (COSY, HSQC, HMBC and NOESY) and by comparison with the literature data.     

Polyhydroxyoleanane-type triterpenoids from Combretum molle and their anti-inflammatory activity

A new oleanane-type triterpene saponin, β-d-glucopyranosyl 2α,3β,6β-trihydroxy-23-galloylolean-12-en-28-oate (1), together with four known oleanane-type pentacyclic triterpenoids, combregenin (2), arjungenin (3), arjunglucoside I (4), and combreglucoside (5) were isolated from the stem bark of Combretum molle. Their structures were established mainly on the basis of 1D and 2D NMR spectral data. Compounds 1–3 exhibited more significant activity against carrageenan-induced paw edema in rat compared to compounds 4 and 5.     

米兰花的水溶性成分研究

目的研究米兰花的水溶性成分。方法通过纯化水加热回流提取米兰花后,对其化学成分进行LC-QTOF分析。结果从米兰花水提取物中分离确定了12种主要成分。结论米兰花水溶性分析得到12种主要化学成分的二级图谱均与数据库有较高的匹配度,为米兰花进一步研究提供理论依据。     

Synthesis of dammarane-type triterpenoids with anti-inflammatory activity in vivo

The 17-alpha-substituted triterpene 1 [(17alpha)-23-(E)-dammara-20,23-diene-3beta,25-diol] showed promising activity in animal models of immunosuppression and inflammation. Using a mouse model for inflammatory skin diseases (oxazolone-induced allergic contact dermatitis, ACD) as the directing in vivo test system, Structure-activity-relationship studies with the aim to understand the necessary structural requirements for the biological activity of 1 were conducted. Furthermore, we anticipated to identify biologically active compounds with the 17beta configuration, which are thermodynamically more stable and much easier to synthesize. This was achieved by identifying the 17-beta substituted dammarane 5B and its analogues.     

Cytotoxic triterpenoids from the bark of Aglaia smithii (Meliaceae)

Two new dammarane triterpenoids, aglinone (1) and aglinin E (20S,24S-epoxy-25-hydroxy-1-en-dammarene) (2) along with three known compounds, 3-epiocotillol (3), aglinin A (4), and eichlerianic acid (5), were isolated from the bark of Aglaia smithii. The chemical structures of the new compound were elucidated on the basis of spectroscopic data interpretation. All the compounds isolated were evaluated for their cytotoxic effects against P-388 murine leukemia cells. Compounds 1, 2, 4 and 5 showed cytotoxicity against P-388 murine leukemia cells with IC₅₀ values of 21, 42, 34, and 11 μg/mL, respectively.     

Structure and stereochemistry of (−)-odorinol,an antileukemic diamide from Aglaia odorata

Bioassay-directed isolation of an antileukemic extract of Aglaia odorata has led to the characterization of (?)-odorinol, a new diamide demonstra     

Two new rocaglamide derivatives from twigs of Aglaia odorata var. microphyllina

Phytochemical investigation of Aglaia odorata var. microphyllina led to the isolation of two new rocaglamide derivatives and three known ones. The structures of the two new compounds were elucidated as 8b-methoxy-desmethylrocaglamide (1) and 3′-hydroxy-8b-methoxy-rocaglamide (2) by spectroscopic techniques (IR, MS, 1D and 2D NMR) and comparing with published data. All the five compounds were evaluated for cytotoxic activity against K562 cell line by MTT method. The results indicated that the OH at 8b position was a decisive group for cytotoxic activity.     

Jatrophane polyesters from the leaves of Euphorbia peplus with anti-inflammatory activity

Three new jatrophane polyesters, Euphopepluanones M-O (1–3), along with eight known ones (4-11), were isolated from the leaves of Euphorbia peplus Linn. Their chemical structures were established based on extensive spectroscopic analysis. The absolute configurations of compound 1 were assigned by X-ray crystallographic analysis. In addition, their anti-inflammatory effects on lipopolysaccharide-induced RAW264.7 macrophages were evaluated in vitro. Among them, 2 and 7 exhibited significant anti-inflammatory activity.     

Three putrescine bisamides from the leaves of Aglaia grandis

Three putrescine (i.e. 1,4-butanediamine) bisamides were isolated from the leaves of Aglaia grandis. Their structures were elucidated by interpretation of spectral data.     

Hypolipidemic and anti-inflammatory properties of phenolic rich Butia odorata fruit extract: potential involvement of paraoxonase activity

Abstract

Aim: This study investigated the effects of polar Butia odorata fruit extract on metabolic, inflammatory, and oxidative stress parameters in rats submitted to a hyperlipidaemia condition induced by tyloxapol.

Methods: Animals were divided into 3 groups: saline, saline plus tyloxapol, and B. odorata extract plus tyloxapol. Animals were treated for 15?days with a saline solution or B. odorata fruit extract and after hyperlipidaemia was induced by tyloxapol.

Results: Treatment with B. odorata extract reduced serum triglyceride, total cholesterol, C-reactive protein, and adenosine deaminase and butyrylcholinesterase activities when compared to the tyloxapol group. HDL-cholesterol and paraoxonase 1 activity were higher in B. odorata extract treated animals when compared to tyloxapol-treated animals. No differences were observed in hepatic oxidative stress parameters. Phenolic compounds present in B. odorata fruit extract were identified and quantified by LC-MS/MS.

Conclusion: These findings indicated that phenolic rich B. odorata extract has hypolipidemic and anti-inflammatory effects in hyperlipidemic rats.     

Stuies on the Chemical Constituents of the Essential Oils from the Leaves of Aglaia odorata Lour

This paper shows the chemical constituents of the essential oils from the leaves of Aglaia odorata Lout. grown in Zhangzhou. By the aid of GC-MS-DS., IR., the following components have been separated and identified: linalool, hendecane, α-copaene, β-elemene, β-caryophyllene, α-humulene, aromadendrene, γ-cadinene, α-himachalene, δ-cadinene, β-guaiene, γ-gurjunene, γ-elemene, humulene epoxide-Ⅰ, humulene epoxide-Ⅱ, β-elemene-9β-ol, β-humulene-7-ol, nerolidol, earyophyllenol-1, farnesol, β-santalol, elemol. This will provide scientific basis for further develophment of the essential oils of the plants of Aglaia Lour.     

Tetracyclic triterpenoids from the leaves of Azadirachta indica

Two new tetracyclic triterpenoids zafaral [24,25,26,27-tetranorapotirucalla-(apoeupha)-6alpha-methoxy-7alpha-acetoxy-1,14-dien-3,16-dione-21-al] (1) and meliacinanhydride [24,25,26,27-tetranorapotirucalla-(apoeupha)-6alpha-hydroxy,11alpha-methoxy-7alpha,12alpha-diacetoxy,1,14,20(22)-trien-3-one] (2) have been isolated from the methanolic extract of neem leaves along with two known constituents nimocinol and isomeldenin. Their structures and the relative configurations were determined by spectroscopic methods ((1)H and (13)C NMR, IR, and MS) and 2D NMR experiments.     

Diterpenoids and triterpenoids in hairy roots of Salvia sclarea

Hairy root culture of Salvia sclarea L. was established following infection with Agrobacterium rhizogenes LBA 9402. The culture was grown in growth regulator-free half-strength B5 Gamborg medium with 30 g l⁻¹ sucrose and was investigated with respect to its capability of producing diterpenoids and triterpenoids. Four diterpenoids (ferruginol, salvipisone, aethiopinone and 1-oxoaethiopinone) and two ursene-type triterpenoids (2α,3α-dihydroxy-urs-12-en-28-oic acid and 2α,3α,24-trihydroxy-urs-12-en-28-oic acid) were isolated from the hairy roots. The presence of three sterols (β-sitosterol, stigmasterol and campesterol), as well as oleanolic and ursolic acids was also shown by GC–MS analysis. The quantitative and qualitative differences in diterpenoid and triterpenoid production patterns between hairy roots grown in the light and in the dark were described.     

Physiological and cellular mechanisms of natural herbicide resource from Aglaia odorata Lour. on bioassay plants

A bioassay-guided fractionation of the allelochemicals of the ethyl acetate fraction extracted from Aglaia odorata led to isolation of a bisamide, odorine. The growth inhibitory effects of odorine and ethyl acetate fraction were studied for comparison on Echinochloa crus-galli. Odorine and ethyl acetate fraction of A. odorata could inhibit the germination and seedling growth of E. crus-galli, with ethyl acetate fraction being more potent. Thus, ethyl acetate fraction was selected for further experiment, E. crus-galli seeds were studied the effects of the ethyl acetate fraction from A. odorata leaves in wettable powder formulation on imbibition and ??-amylase activity. It was found that treated seeds showed lower imbibition and ??-amylase activity. The results of cytogenetic bioassay in Allium cepa roots showed that ethyl acetate fraction inhibited cell mitosis and induced mitotic abnormalities resulting from its action on chromatin organization and mitotic spindle in the exposed roots.     

Pentacyclic triterpenoids and other constituents isolated from the leaves of Gambeya lacourtiana and their antibacterial activity

The phytochemical study was done on the leaves of Gambeya lacourtiana. This plant has been used in traditional medicine to treat of different ailments such as uterine heamorrhage, metritis and other vaginal infections. Chromatographic fractionation and purification on the leaves crude extract afforded lupeol acetate (1), lupenone (2), lupeol (3), taraxerol (4) stigmasterol (5), erythrodiol (6), chamaedrydiol (7), methyl pheophorbide-a (8), corosolic acid (9), tormentic acid (10), epicatechin (11) and 22-dihydrospinasterol 3-O-β-D-glucopyranoside (12). The structures of compounds 1–12 were elucidated on the basis of 1D and 2D NMR, mass spectrometric and the spectroscopic data as well as comparison with the literature. Compounds 4, 7–10 and 12 were isolated for the first time from Gambeya genus. Crude extract, fractions and compounds 6–12 were evaluated for their antibacterial activity. Methyl pheophorbide-a (8) demonstrated moderate activity against Salmonella typhi CPC with MIC values of 62.5 μg/mL. The chemophenetic significance of these compounds is also discussed.     

Cucurbitane-type triterpenoids from the branches and leaves of Elaeocarpus sylvestris

The chemical structures of nine cucurbitane-type triterpenoids from the branches and leaves of Elaeocarpus sylvestris (Elaeocarpaceae), including undescribed 29-hydroxymogroside I E₂, epimogroside I E₂, epimogroside I E₁, 24-oxomogroside I E₁, and 11-O-acetylmogroside I E₁, were determined using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. The absolute configuration of 29-hydroxymogroside I E₂ was confirmed by performing an X-ray diffraction analysis. Cucurbitacin D and 11-O-acetylmogroside I E₁ showed cytotoxicity toward human leukemia HL-60, human lung adenocarcinoma A549, human hepatoma SMMC-7721, human breast cancer MCF-7, and human colon cancer SW480 cell lines. The presence of a 11-O-acetyl group might increase the cytotoxicity of this type of triterpenoids.     

Isolation and Identification of the Constituents of Volatiles of Dry Flowers of Aglaia odorata Lour

The headspace volatiles of the dry flowers of Aglaia odorata were trapped by a modified circulating adsorption method and were analyzed by GC/MS techniques after desorption by solvent. The components were identified by re, ass spectral and temperature-programmed retention index data on two types of glass capillary columns (OV-101 and PEG-20 M). 54 compounds have been identified from the volatiles, including 21 sesquiterpenes, 8 aldehydes, 7 alkyl benzenes, 6 alkanes, 6 other oxygen-containing compounds and I nitrogen containing compound. 29 compounds have not been reported in the studies on the constituents of the essential oil or absolute oil of the flowers.     

Phenylpropanoids and triterpenoids from Tripterygium regelii and their anti-inflammatory activities

Two new compounds named cleroserroside C (1), schisphenlignan O (2), as well as twenty-one known compounds (3–23) were isolated from the roots of Tripterygium regelii. The structures of the new compounds were determined by 1D and ²D NMR spectra and HR-ESI-MS data. The known compounds were determined by comparing the ¹D NMR data in the literature. All compounds were evaluated for anti-inflammatory activity using the LPS-induced RAW264.7 inflammatory cell model, and the results showed that compounds 1, 8-11, 15-16, and 20-21 had good anti-inflammatory activity (IC₅₀ < 20 μM). The cytotoxicity of all compounds was tested by CCK-8 assay, using RAW264.7 cells. The results showed that all compounds had no cytotoxicity to RAW264.7 in the range of 0 ~ 200 μM.