To investigate chemical constituents contained in cytotoxic petroleum ether extractive fractions from ethanol extracts of Cirsium setosum. The constituents were separated and purified by a combination of various chromatographic methods including silica gel, Sephadex LH-20, and preparative HPLC. Structures of the isolates were elucidated by spectroscopic methods including 1D, 2D NMR and MS methods. The compound structures were also determined by reference to literature. Twelve compounds were separated from the petroleum ether fraction of ethanolic extract and elucidated as lupenyl acetate (1), lupeol (2), lupenone (3), beta-amyrin (4), psi-taraxasterol (5), psi-taraxasteryl acetate (6), taraxasteryl acetate (7), marsformoxide B (8), alpha-amyrenone (9), beta-amyrenone (10), taraxasterone (11) and psi-taraxasterone (12). Of them, compounds 3, 5, 7-12 were separated from this genus for the first time.
Chromatography, High Pressure Liquid ; Cirsium ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Magnetic Resonance Spectroscopy ; Oleanolic Acid ; analogs & derivatives ; chemistry ; Pentacyclic Triterpenes ; chemistry ; Sterols ; chemistry ; Triterpenes ; chemistry

OBJECTIVETo investigate the chemical constituents in Bruguiera sexangula var. rhynchopetala.

METHODSilica gel flash chromatography together with Sephadex LH - 20 were performed for the isolation and purification of the petrol ether fraction of this plant, and the structures were elucidated by spectral analysis as well as the comparison of the spectral data with those reported in the literatures.

RESULTNine compounds were obtained and identified as lupeol (1), lupeone (2), trans-hydroxy-cinnamoyl ester of lupeol (3), taraxerone (4), beta-amyril-palmitate (5), squalene (6),beta-sitosterol (7), daucosterol (8) and 7alpha-hydroxy-sitosterol (9).

CONCLUSIONAll the compounds were first isolated from B. sexangula var. rhynchopetala.

Oleanolic Acid ; analogs & derivatives ; chemistry ; isolation & purification ; Pentacyclic Triterpenes ; Plants, Medicinal ; chemistry ; Rhizophoraceae ; chemistry ; Sitosterols ; chemistry ; isolation & purification ; Triterpenes ; chemistry ; isolation & purification

Tripterygium hypoglaucum (Levl.) Hutch, a traditional Chinese medicinal herb with a long history of use, is widely distributed in China. One of its main active components, celastrol, has great potential to be developed into anti-cancer and anti-obesity drugs. Although it exhibits strong pharmacological activities, there is a lack of sustainable sources of celastrol and its derivatives, making it crucial to develop novel sources of these drugs through synthetic biology. The key step in the biosynthesis of celastrol is considered to be the cyclization of 2,3-oxidosqualene into friedelin under the catalysis of 2,3-oxidosqualene cyclases. Friedelin was speculated to be oxidized into celastrol by cytochrome P450 oxidases (CYP450s). Here, we reported a cytochrome P450 ThCYP712K1 from Tripterygium hypoglaucum (Levl.) Hutch that catalyzed the oxidation of friedelin into polpuonic acid when heterologously expressed in yeast. Through substrate supplementation and in vitro enzyme analysis, ThCYP712K1 was further proven to catalyze the oxidation of friedelin at the C-29 position to produce polpunonic acid, which is considered a vital step in the biosynthesis of celastrol, and will lay a foundation for further analysis of its biosynthetic pathway.
Anti-Obesity Agents ; Cytochrome P-450 Enzyme System/metabolism* ; Pentacyclic Triterpenes ; Squalene/analogs & derivatives* ; Tripterygium/metabolism* ; Triterpenes/metabolism*

Five compounds were separated from Sambucus chinensis and identified as maslinic acid(1), 12alpha, 13-dihydroxyolean-3-oxo-28-oic acid(2), 13-hydroxyolean-3-oxo-28-oic acid (3), 3-oxo oleanolic acid (4), corosolic acid (5). Of them,compound 3 was a new compound, and compounds 1, 2, 4, and 5 were seperated from this plant for the first time.
Oleanolic Acid ; analysis ; Sambucus ; chemistry ; Triterpenes ; analysis

OBJECTIVETo study the chemical constituents of root of Actinidia macrosperma.

METHODChromatographic methods were used to isolate compounds from A. macrosperma and spectroscopic methods were used to identify the structures of the isolated compounds.

RESULTEight compounds were obtained and identified as 12-oleanene-2alpha, 3alpha, 24-triol (1), isotachioside (2), asiatic acid (3), catechin (4), epicatechin (5), ursolic acid (6), beta-daucosterol (7), beta-sitosterol (8).

CONCLUSIONAll these compounds were isolated from this plant for the first time, compound 1, 2 were obtained from this genus for the first time.

Actinidia ; chemistry ; Catechin ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Hydroquinones ; chemistry ; isolation & purification ; Oleanolic Acid ; analogs & derivatives ; chemistry ; isolation & purification ; Pentacyclic Triterpenes ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Triterpenes ; chemistry ; isolation & purification

Azadirachtin, as a botanical insecticide, is a highly oxidized limonoid triterpenoid existing in the seeds of Azadirachta indica. However, due to the low content in the seeds, the production of azadirachtin by seed extraction has low yield. Chemical synthesis of azadirachtin is characterized by complex process and low yield. Synthetic biology provides an alternative for the supply of azadirach-tin. In this study, two oxidosqualene cyclases AiOSC1 and MaOSC1 respectively derived from A. indica and Melia azedarach were identified in yeast. A yeast strain producing tirucalla-7,24-dien-3β-ol was constructed by integration of AiOSC1, Arabidopsis thaliana-derived squalene synthase gene(AtAQS2), and Saccharomyces cerevisiae-derived truncated 3-hydroxy-3-methyl-glutaryl coenzyme A reductase gene(PgtHMGR) into the delta site of yeast. Then, the function of MaCYP71BQ5 was successfully verified in yeast after this gene was introduced into the constructed yeast strain. This study not only laid a foundation for the biosynthesis of tirucalla-7,24-dien-3β-ol, but also provided a chassis cell for the functional identification of cytochrome oxidases(CYP450 s) in azadirachtin biosynthesis pathway.
Azadirachta ; Limonins ; Saccharomyces cerevisiae/genetics* ; Triterpenes

Panax ginseng C.A. Meyer (Panax ginseng) has been used for several thousand years to prolong longevity in Asian countries. Ginsenosides are the most active components isolated from ginseng and belong to damarane saponin which are separated into protopanaxadiol and protopanaxtriol. To evaluate the complex effect of ginsenoside in apo E null mice, ginseng extract were intraperioneally (i.p.) injected and provided high-cholesterol diet for 12 weeks. Ginseng extract came from were i.p. injected with dose of 100 mg/kg/day for 4 weeks in the last experimental duration. Ginseng extract used experiment was abundant Rb1, Rc, Re, and Rg1 and PD:PT ratio was 1.2. The high-cholesterol diet induced liver damage was significantly reduced by ginseng extract. Results from plasma lipid profiles and atherogenic index were improved by ginseng extracts. The GE group significantly decreased plasma TG and TC by 73% and 61% compared to apo E (-/-) group. Also ginseng extract tend to decrease lipid profiles and lipidperoxidation contents in liver and heart. Ginseng extract with an abundant amount of Rg1 significantly suppressed the apoptosis induction of cardiac tissue. In conclusion, ginseng extract (PD:PT = 1) was improved lipid profiles and anti-oxidant effects.
Animals ; Antioxidants ; Apolipoproteins E ; Apoptosis ; Asian Continental Ancestry Group ; Diet ; Ginsenosides ; Heart ; Humans ; Liver ; Longevity ; Mice ; Panax ; Plasma ; Porphyrins ; Sapogenins ; Saponins ; Triterpenes

The current study aims to investigate the pharmacokinetic properties of Huangqin Tang on different oral doses. An LC-MS method for simultaneous determination of flavonoids and terpenoids in rat plasma was developed and validated. Plasma samples were treated with hydrochloric acid (containing 1% ascorbic acid), precipitated with acetonitrile, separated on a Zorbax SB-C18 column, detected by single quadruple mass spectrometry with an electrospray ionization interface, and quantified using selected ion monitoring mode. All pharmacokinetic parameters were processed by non-compartmental analysis using WinNonlin software. The results of specificity, linearity, intra-day and inter-day precisions, accuracy, and stability for LC-MS assay were suitable for the quantification of paeoniflorin, baicalin, wogonoside, baicalein, wogonin, oroxylin A, glycyrrhizic acid and glycyrrhetinic acid in rat plasma. The concentration-time profiles of baicalin, wogonoside, baicalein, wogonin, oroxylin A and glycyrrhizic acid showed double-peak phenomenon after Huangqin Tang was orally administered at 40 g x kg(-1) dose; all eight constituents in rat plasma showed good dose-exposure relationship within the dosage of 10-40 g x kg(-1); although plasma concentrations were different, the flavonoids with the same backbone showed the similar fate in the body with the corresponding dosage. In conclusion, the LC-MS assay was successfully applied for the pharmacokinetic study of multi-constituents of Huangqin Tang with different doses. Additionally, these constituents demonstrated good pharmacokinetic properties in the body.
Administration, Oral ; Animals ; Chromatography, Liquid ; Dose-Response Relationship, Drug ; Drugs, Chinese Herbal ; administration & dosage ; chemistry ; Flavanones ; blood ; pharmacokinetics ; Flavonoids ; blood ; pharmacokinetics ; Glucosides ; blood ; pharmacokinetics ; Glycyrrhetinic Acid ; blood ; pharmacokinetics ; Glycyrrhizic Acid ; blood ; pharmacokinetics ; Male ; Monoterpenes ; blood ; pharmacokinetics ; Pentacyclic Triterpenes ; blood ; pharmacokinetics ; Rats ; Rats, Wistar ; Spectrometry, Mass, Electrospray Ionization

OBJECTIVETo investigate the chemical constituents of Ilex cornuta.

METHODThe chemical constituents were isolated by column chromatographic methods. And the structures were identified by spectral data.

RESULTSeven compounds were isolated and identified as follows: 2alpha-hydroxy ursolic acid (1), arjunolic acid (2), 23-hydroxy ursolic acid (3), 27-0-p-(Z) -coumaroyl ursolic acid (4), 27-O-p-(E)-coumaroyl ursolic acid (5), asiatic acid (6).

CONCLUSIONCompound 1, 2 were obtained from this genus for the first time and 3-6 from this plant for the first time.

Ilex ; chemistry ; Magnetic Resonance Spectroscopy ; Pentacyclic Triterpenes ; Plant Leaves ; chemistry ; Triterpenes ; chemistry

OBJECTIVEIsolation and structural elucidation of the constituents of China mangrove Sonneratia apetala.

METHODchromatography methods were used for isolation of compounds, spectroscopic methods were used for structural identifyication.

RESULTseven known compounds named (+/-) symgaresinol, betulinic acid, lupeol, lupeone, stigmast-5-ene-3beta, 7alpha-diol, beta-alpha myrin hexadecaneate, physcoion were isolated.

CONCLUSIONthese known compouns were unreported previously from this plant.

Magnoliopsida ; chemistry ; Pentacyclic Triterpenes ; Plants, Medicinal ; chemistry ; Triterpenes ; chemistry ; isolation & purification