Natural variations in flavonoids and triterpenoids of Cyclocarya paliurus leaves

Cyclocarya paliurus is widely distributed in subtropical areas of China.Secondary metabolites in the leaves,including flavonoids and triterpenoids,provide protection against diseases such as hyperlipidemia,diabetes,hypertension,and hypoimmunity.In this study,343 C.paliurus leaves were collected from 32 distinct populations covering most of the main distribution,to deduce the response of flavonoids and triterpenoids to seven environmental factors.Principal component analysis was performed using seven flavonoid and six triterpenoid compounds.The results show that altitude,latitude,and longitude significantly contributed to variations in total flavonoid and triterpenoid contents.In addition,the interaction of these metabolites was extensively correlated with environment changes,and therefore should be considered during selection and cultivation.

Analysis of three types of triterpenoids in tetraploid white birches(Betula platyphylla Suk.) and selection of plus trees

Betulin, oleanolic acid, and betulinic acid are naturally occurring pentacyclic triterpenoids that have significant medicinal value. Considerable amounts of these triterpenoids are available in the outer bark of white birch. In this study, we used ultrasound-assisted extraction （UAE） to extract triterpenoids from birch bark rapidly and with high efficiency. Using high performance liquid chro- matography （HPLC）, three types of triterpenoids were separated and detected. We examined the differences among triterpenoids extracted from diploid versus tetra- ploid white birch. Then, we used factor analysis to screen out tetraploid white birches with comprehensively excel- lent performance. The results indicate that the optimum conditions for extraction include the use of ethanol as an extraction solvent, a solid-to-liquid ratio of 0.1 g/10 ml, ultrasonic power set at 100 W, a temperature of 60 ℃ and an extraction time of 15 min. A reversed-phase C18 col- umn （4.6 mm × 250 mm × 5 μm） with a column tem- perature of 30 ℃ and the mobile phase composed of A （acetonitrile） and B （0.1% aqueous phosphoric acid, v/v） at a flow rate of 0.5 ml/min were used, and the detection wavelength was 195 nm. No significant difference wasobserved between diploid and tetraploid white birch in terms of the content of three types of triterpenoids （at a confidence level of 0.05）. As triterpenoid content, height, and DBH （diameter at breast height） are strongly interre- lated, we used factor analysis to evaluate all individuals, and we screened out six plus trees with excellent com- prehensive characters.

Six New 9,19-Cycloartane Triterpenoids from Cimicifuga foetida L.

Six new 9,19-cycloartane triterpene derivatives,as well as 3 known analogues(7–9),were isolated from the roots of Cimicifuga foetida L.Their structures were established on the basis of extensive spectroscopic analyses(IR,UV,ORD,HRESIMS,1D and 2D NMR).

Lactam Triterpenoids from the Bark of Toona sinensis

Three new limonoid-type triterpenoids,namely toonasins A–C(1–3)with a rare lactam E ring,along with six known compounds(4–9)were isolated from the barks of Toona sinensis.The structures of new compounds were elucidated by interpretation of spectroscopic data,and the relative configuration of compound 1 was further characterized by X-ray crystallographic analyses.The isolated compounds were evaluated for their cytotoxic activities against five human tumor cell lines(HL-60,SMMC-7721,A-549,MCF-7 and SW480),and compounds 3 and 5 showed weak cytotoxicities.

Lanostane Triterpenoids from Fruiting Bodies of Ganoderma leucocontextum

Six new lanostane-type triterpenoids,namely leucocontextins S-X(1-6),together with twelve known compounds,were isolated from the fruiting bodies of Ganoderma leucocontextum.Their structures were established by MS and NMR data.

Intercedenol A and B,Two New Triterpenoids from the Sea Cucumber Mensamaria intercedens

Two new triterpenoids named intercedenol A and B were isolated from the acid hydrolysate of the crude glycoside fraction. The structures were elucidated by ESI-MS and NMR spectrum.

Protective effects of total triterpenoids extracts from Cyclocarya paliurus(Batal.)Iljinskaja on STZ-stimulated INS-1 cells through regulating of autophagy and apoptosis

OBJECTIVE To explore the protective effects of total triterpenoids extracts from Cyclocarya paliurus(Batal.)Iljinskaja on STZ-stimulated INS-1 cells through regulating of autophagy and apoptosis.METHODS INS-1cells were cultured in media containing 3n M STZ and different doses of total triterpenoids extracts from Cyclocarya paliurus(Batal.)Iljinskaja.The proliferation of cells was examined by MTT assay,ROS content were detected by fluorescence enzyme label.The levels of superoxide dismutase(SOD),glutathione peroxidase(GSH-Px),hydrogen peroxidase(CAT),malondialdehyde(MDA)were also measured by colorimetry.The activities of caspase-3,9 were also observed by Caspase colorimetric assay kit in each group.The expressions of Bcl-2 m RNA and Bax m RNA were detected by Real time PCR,protein expression of LC3-Ⅱand PARP were detected by Western blotting.RESULTS Compared with the control group,total triterpenoids extracts from Cyclocarya paliurus(Batal.)Iljinskaja could promote the proliferation of INS-1 cells no matter with STZ or not when its concentration lower than 25μg·m L-1;but when its concentration higher than 100μg·m L-(1use individually)or 50μg·m L-1(combined use),total triterpenoids extracts from Cyclocarya paliurus(Batal.)Iljinskaja might significantly inhibite the growth of the cells whether STZ existed or not.Total triterpenoids extracts from Cyclocarya paliurus(Batal.)Iljinskaja(6.25,12.5,25μg·m L-1)might inhibit INS-1cell apoptosis,decrease intra-cellular ROS contents,improve the s upernatant liquid SOD,GSH-PX,CAT activities,decrease MDA level,promote INS-1 cell secreting insulin,decrease the protein expressions of autophagy protein LC3Ⅱand apoptosis regulating protein cleaved PARP protein,up-regulate the anti-apoptotic protein Bcl-2 m RNA expression,down-regulate the pro-apoptotic protein Bax m RNA expression and Bcl-2and Bax,reduce the activity of caspase-9 and caspase-3(P<0.05 or P<0.01).CONCLUSION Total triterpenoids extracts from Cyclocarya paliurus(Batal.)Iljinskaja has good protective effect on STZ-stimulated INS-1cells.It can inhibit STZ injured INS-1 cells to overproduce ROS production,enhance endogenous antioxidant enzymes(GSH-Px,SOD,CAT activities),reduce the expression of autophagy protein LC3Ⅱand apoptosisregulating protein cleaved PARP,up-reglute the antiapoptosis protein Bcl-2 expression,down-regulate the pro-apoptotic protein Bax expression,decrease the caspase-9 and caspase-3 activities,and improve the INS-1cell survival rate,and then play a protective effect on damaged INS-1 cells.

Intestinal Absorption of Ergostane and Lanostane Triterpenoids from Antrodia cinnamomea Using Caco-2 Cell Monolayer Model

Antrodia cinnamomea is a precious medicinal mushroom.It exhibits promising therapeutic effects on cancer,intoxication,hypertension,hepatitis,and inflammation.Its major bioactive constituents are ergostane and lanostane triterpenoids.In this study,we used intestinal Caco-2 cell monolayer model to reveal the intestinal absorption property of 14 representative triterpenoids from A.cinnamomea.The bidirectional transport through the monolayer at different time points was monitored by a fully validated LC/MS/MS method.In the case of pure compounds,ergostanes 5(25R-antcin H),6(25Santcin H)and 10(25R-antcin B)could readily pass through the Caco-2 cell layer,whereas lanostanes 13(dehydroeburicoic acid)and 14(eburicoic acid)could hardly pass through.When the cells were treated with A.cinnamomea extract,antcins A,B,C,H and K(1–6 and 9–11)were absorbed via passive transcellular diffusion,and showed high PAB and PBA values(>2.5×10^(-5) cm/s).Meanwhile,the lanostanes dehydrosulphurenic acid(8),15a-acetyldehydrosulphurenic acid(12),13 and 14 exhibited poor permeability.Transport features of these compounds were consistent with their pharmacokinetic behaviors in rats.This study could also be helpful in predicting the intestinal absorption of A.cinnamomea in human.

Triterpenoids from Ainsliaea latifolia and Their Cyclooxyenase‑2(COX‑2)Inhibitory Activities

Eight new triterpenoids were isolated from Ainsliaea latifolia.The structures of these compounds were elucidated by interpretation of spectroscopic data,including HRESIMS and NMR data.Compounds 4–6 are identifed as rare trinorcucurbitane or tetranorcucurbitane triterpenoids.The absolute confgurations of compounds 1 and 2 were confrmed by Snatzke’s method.All compounds were evaluated for their inhibition against cyclooxyenase-2(COX-2),in which compound 4 showed signifcant inhibitory efect against COX-2 with IC_(50) value of 3.98±0.32μM,comparable to that of positive control NS-398(IC504.14±0.28μM).

New Dammarane Triterpenoids,Caffruones A–D,from the Cherries of Coffea arabica

In present study,four new dammarane-type triterpenoids,namely caffruones A–D(1–4),were isolated from the cherries of Coffea arabica.Their structures were elucidated by extensive spectroscopic analysis including 1D,2D NMR(HSQC,HMBC,^(1)H–^(1)H COSY,and ROESY),HRMS and IR spectra.This is the first time that tetracyclic triterpenes have been reported in genus Coffea.

Optimization of Extraction Process and Determination of Total Triterpenoids from Semen Trichosanthis by Response Surface Methodology

[Objectives] To optimize the extraction process and determine the total triterpenoids from Semen Trichosanthis.[Methods]The Box-behnken response surface methodology was applied to optimize the extraction conditions of total triterpenoids in Semen Trichosanthis.And the spectrophotometry was used to determine the content of total triterpenoids in Semen Trichosanthis.[Results] The optimal extraction conditions were solid to liquid ratio of 40∶ 1,ultrasonic time of 20 min,and ultrasonic power of 100 W.Under these conditions,the content of total triterpenoids in Semen Trichosanthis was significantly different among the 10 production areas,among which the No.9 production area(Anhui 1) had the highest total triterpenoids content of 45.71 mg/g,while No.7 production area(Shandong) had the lowest total triterpenoids content of 15.22 mg/g.[Conclusions]The Box-behnken response surface methodology is reliable for the extraction of total triterpenoids in Semen Trichosanthis,and the spectrophotometry is proper for determining the content of total triterpenoids in Semen Trichosanthis.There are large differences in the content of total triterpenoids in Semen Trichosanthis produced in different areas.

Three New Triterpenoids from European Mushroom Tricholoma terreum

Three rare triterpenoids,saponaceolides Q–S(1–3),have been isolated from fruiting bodies of the mushroom Tricholoma terreum.Their structures were characterized based on extensive spectroscopic data.Compound 1 showed certain cytotoxicities against four human tumor cell lines.

New apotirucallane-type triterpenoids from Chisocheton paniculatus

Two new apotirucallane triterpenoids,namely chisiamols G(1)and H(2),featuring a 21,23-lactone,together with five known triterpenoids,were isolated from the twigs of Chisocheton paniculatus.The structures of the new compounds were elucidated on the basis of spectroscopic and chemical methods.

The triterpenoids-enriched extracts from Antrodia cinnamomea mycelia attenuate alcohol-induced chronic liver injury via suppression lipid accumulation in C57BL/6 mice

The major pathologic hallmark of the alcoholic liver disease(ALD)is the representation of chronic alcohol-induced hepatocyte lipid accumulation.This study aims to investigate the hepatoprotective role of triterpenoids-enriched extracts from Antrodia cinnamomea mycelia(ACT)in chronic alcohol-induced liver injury mice,establishing in C57BL/6 mice through gradient alcohol feeding for 24 weeks.In longterm alcohol consumption mice,the significantly lost body weight,increased organ indexes,hepatic alanine aminotransferase and aspartate aminotransferase levels were all remissed after 6-week ACT orally administration,showing its hepatoprotective property.ACT suppressed the triglyceride,total cholesterol and low-density lipoprotein levels,and enhanced high-density lipoprotein levels in serum or/and liver of chronic alcohol damaged mice.Combining with the pathological observations,ACT displayed an anti-steatosis effects to restrain the progress of ALD.Based on proteomic analysis and enzyme-linked immunosorbent assay,ACT had been confi rmed to regulate the levels of lipid biogeneration-related factors and depressed the over-accumulation of hepatic reactive oxygen species.According to further data,ACT prevented alcoholic liver injury may be associated with mediating lipid metabolism-related to PGC-1αand NF-κB signaling.In summary,ACT protected the body against chronic alcohol ingest induced liver injury through its regulation lipid on metabolism.

Optimization of Extraction Method of Triterpenoids from Artemisia selengnesis Turcz

[Objectives]The research aimed to optimize the extraction method of triterpenoids from A. selengnesis. [Methods]The ultrasonic extraction of triterpenoids in A. selengnesis was optimized by single factor analysis( including infusion time,ethanol concentration,ultrasonic power,extraction time,and liquid-solid ratio) and response surface method. [Results]The optimum extracting process of triterpenoids was as follows: infusion time of 65 min,ethanol concentration of 80%,ultrasonic power of 275 W,extraction time of 30 min,and liquid-solid ratio of 34 m L/g. Under the optimized condition,the extraction content of triterpenoids reached( 18. 26 ± 0. 10) mg/g. [Conclusions] The optimized extraction had a good modal on practice in developing and utilization.

Limonoids and triterpenoids from the twigs and leaves of Dysoxylum hainanense

Four new limonoids,dysohainanins A-D(1-4),and two new triterpenoids,dysohainanins E and F(5 and 6),together with seven known ones were isolated from the twigs and leaves of Dysoxylum hainanense Merr.The structures of the new compounds were determined by a variety of spectroscopic methods.The cytotoxic activities of these compounds were evaluated,and the known compound ent-19-nor-4,16,18-trihydroxy-8(14)-pomaren-15-one(13)showed in vitro cytotoxicity against HL-60,A-549,MCF-7,and SW480 cells,with IC50 values of 24.3,28.1,30.7,and 22.5mM,respectively.Compounds 2 and 3 were tested their insecticidal activities using brine shrimp and both of them were inactive.

Triterpenoids and Sterols from the Leaves and Twigs of Melia azedarach

Two new triterpenoids(1 and 2)and a new sterol(3),together with six known constituents(4–9),were isolated from the leaves and twigs of Melia azedarach.Their chemical structures were elucidated on the basis of spectroscopic analysis.

3,4-Secocycloartane Triterpenoids from the Cones of Pseudolarix amabilis

Four new 3,4-secocycloartane triterpenoids,pseudolactones A-D(1-4),were isolated from the ethanol extract of the cones of Pseudol arixamabilis.Their structures were established by extensive 1D-and 2D-NMR experiments.The cones of P.arixamabilis are enriched in the ring-expanded or cleaved cycloartane triterpenoids.This work provides new insight into cycloartane triterpenoids from the cones of P.arixamabilis.

Structures,Chemical Conversions,and Cytotoxicity of Tricholopardins C and D,Two Tricholoma Triterpenoids from the Wild Mushroom Tricholoma pardinum

Two undescribed Tricholoma triterpenoids,namely tricholopardins C(1)and D(2),were isolated from the wild mushroom Tricholoma pardinum.Their structures with absolute configurations were elucidated by spectroscopic methods,as well as the single crystal X-ray diffraction.Compounds 1 and 2 were further obtained by chemical conversions from the known analogues.Compound 1 showed significant cytotoxicity to MCF-7 and Hela cell lines with IC_(50)values of 4.7μM and 9.7μM,respectively.Its mechanism of inducing MCF-7 cell apoptosis was studied briefly.

Triterpenoids from Uncaria rhynchophylla and Their PTP1B Inhibitory Activity

Uncaria rhynchophylla(Gouteng)is a famous traditional Chinese medicine used for psychiatric and hypotensive purposes in China.In this study,the ethyl acetate(EtOAc)part of U.rhynchophylla was revealed with protein tyrosine phosphatase 1B(PTP1B)inhibitory activity.Subsequent investigation on the EtOAc part yielded one new triterpenoid,3β-formyloxy-6β,19α-dihydroxyurs-12-en-28-oic acid(1)and four known ones,3β,6β,19α-trihydroxyurs-12-en-28-oic acid(2),2-oxopomolic acid(3),3β,19α-dihydroxy-6-oxo-olean-12-en-28-oic acid(4)and sumaresinolic acid(5).The structure of compound 1 was determined by extensive HRESIMS,IR,1D and 2D NMR spectroscopic analyses.Two ursane-type triterpenoids(2 and 3)showed selective inhibition on PTP1B with IC50 values of 48.2 and 178.7μM.The enzyme kinetic study suggested that compounds 2 and 3 were mixtype inhibitors on PTP1B with Ki values of 15.6 and 132.5μM.This investigation manifests the antidiabetic potency of U.rhynchophylla with triterpenoids as the active constituents.