Two New Triterpenes from Neonauclea sessilifolia

Two new triterpenoids, 3 β, 15α, 21 β, 23-tetrahydroxy-12-oleanen-28-oic acid (1), 3β , 6 α , 21β, 23-tetrahydroxy-12-oleanen-28-oic acid (2), together with seven known compounds, viz., paeonol (3), 3, 4-dihydroxybenzoic acid (4), scosoletin (5), anthraquinones chrysophanol (6), 4H-1-benzopyran-4-one, 5, 7-dihydroxy-2-methyl (7),β-sitosterol (8) and stigmasterol glucoside (9) were isolated by the chromatography of the silica gel, RP-18 and Sephadex-LH 20 from the EtOAc extract of Neonauclea sessilifolia (Roxb.) Merr. ( Rubiaceae ). Their structures were elucidated based on spectral analysis including 1D-, 2D-NMR (HMQC, HMBC), IR and EIMS. Among them, compound 6 was shown to possess inhibitory activity on the growth of Mycobacterium tuberculosis (Zopf) Lehmann et Neumann with a minimum inhibitory amount of 25μg, compounds 2 and 4 also showed weak inhibitory activities on the growteof M. tuberculosis.

A new triterpene glycoside from sea cucumber Holothuria leucospilota

A new triterpene glycoside, leucospilotaside A, along with a known saponin, isolated from sea cucumber Holothuria leucospilota, and its structure was elucidated as 3β-O-[4-O-sodiumsulfate-β-d-quinovopyranosyl-(1 → 2)-β-d-xylopyranosyl]-holosta-22-ketone-9-en-17α,25α-diol (1) by extensive spectroscopic analysis and chemical methods. Leucospilotaside A (1) has a ketone carbonyl group (22) in the aglycon side chain.

Two New Pentacyclic Triterpenes from Sabia parviflora

Two new pentacyclic triterpene acids, 1a, 3b-dihydroxyl-olean-12-en-28-oic acid and 1a, 2a, 3b-trihydroxyl-olean-12-en-28-oic acid, were isolated from the arial parts of Sabia parviflora.

A New Triterpene from Cephalomappa sinensis

A new triterpene 1, 1 beta, 2 alpha, 3 beta -trihydroxylup-20 (29) -ene was isolated from Cephalomappa sinensis. The structure was elucidated mainly on the basis of 1D and 2D NMR spectral means.

Oleanane-triterpene Saponins from Clinopodium urticifolium

Four new oleanane triterpene saponins were isolated and purified from the whole plant of Clinopodium urticifolium. They were 3B 16B, 23, 28-tetrahydroxyoleana-9 (11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 1; 3B, 16B, 21B, 23, 28-pentahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-2)]-[B-D-glucopyranosyl-(1-3)]- B-D-fucopyranoside 2; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]-B-D-fucopyranoside 3; 3B, 16B, 23, 28-tetrahydroxyoleana-9(11), 12(13)-diene-3-yl-[B-D-gluco-pyranosyl-(1-4)-B-D-glucopyranosyl-(1-6)-B-D-glucopyranosyl-(1-3)]-[B-D-glucopyranosyl-(1-2)]- B-D-fucopyranoside 4. Their structures were elucidated on the basis of interpretation of NMR and MS data and from chemical evidence.

Leucospilotaside C,a new sulfated triterpene glycoside from sea cucumber Holothuria leucospilota

A new triterpene glycoside, leucospilotaside C, along with two known saponin, was isolated from sea cucumber Holothuria leucospilota collected from the South China Sea, and its structure was elucidated as 3-0-{4′-O-sodiumsulfate-β′-D-xylopyranosyl}- holosta-22,25-epoxy-9-ene-3β,12α,17α-triol （1） by extensive spectroscopic analysis and chemical methods. The glycosides have the same triterpene aglycone, but differ in the oligosaccharide moieties.

A new dammarane-type triterpene saponin from Gynostemma pentaphyllum

One new dammarane-type triterpene saponin,named(20S)-3β,20,21-trihydroxydammar-24-ene 3-O-[α-L-rhamnopyranosyl- (1→2)][β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(1),was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino.Its structural elucidation was accomplished mainly on the basis of the interrelation of spectroscopic methods, such as IR,HR-TOF-MS,NMR.

A new derivative of triterpene with anti-melanoma B16 activity from Conyza canadensis

A new derivative of triterpene named Erigeronol 1 was isolated from the EtOH extract of the aerial part of Conyza canadensis together with 15 known compounds for the first time from this plant.The structure of Erigeronol 1 was elucidated as 3-O-（hydroxyacetyl） -23,28-dihydroxy-β-amyrin by hydrolysis and spectroscopic analysis.Erigeronol 1 showed potent cytotoxic activity with IC_（50） value of 7.77±0.47μg/mL against melanoma B16 determined by the 3-（4,5-dimethylthiazo-2-yl）-2,5-diphenyltetrazolium bromide（MTT） method.

Antiglycation,antioxidant,antiacne,and photoprotective activities of crude extracts and triterpene saponin fraction of Sapindus saponaria L.fruits:An in vitro study

Objective:To evaluate the photoprotective,antioxidant,antiglycation,and antiacne activities of crude extract(CESs)and triterpene saponin fraction(TSSs)of Sapindus saponaria.Methods:HPLC-MS purification was performed on a Symmetry TM C18 column.The saponins were identified by a UV detector.Antioxidant activity was evaluated by DPPH and O_(2)^(−)radicals scavenging,and FRAP and TBARS assays.Glycation activity was assessed by relative electrophoretic mobility and inhibition of advanced glycation end products(AGEs)formation.Additionally,antiacne activity was determined by inhibition of Cutibacterium acnes,and photoprotective effect was evaluated by Mansur’s method.Results:Most of the triterpene saponins detected in the fraction by HPLC-MS analysis were hederagenin as the aglycon.CESs and TSSs presented varying antioxidant activity in DPPH(CESs:75.69%and TSSs:83.65%),FRAP(CESs:425.39μM TE/g DW and TSSs:649.36μM TE/g DW),TBARS(CESs:42.96%and TSSs:52.16%)and O_(2)^(−)radicals scavenging(CESs:61.33%and TSSs:86.69%)tests.CESs and TSSs also exhibited antiglycation activity comparable to bovine serum albumin treated with aminoguanidine.In addition,CESs and TSSs showed inhibition of AGE formation(34.48%and 61.85%,respectively).Antiacne activity against Cutibacterium acnes was observed with a minimum inhibitory concentration equal to minimum bactericidal concentration(CESs:36.11µg/mL and TSSs:18.34µg/mL).In photoprotective assays,CESs and TSSs showed maximum absorbance of 1.42 to 0.20 and 2.80 to 1.30,respectively,in the wavelength range of 260 to 400 nm.Furthermore,CESs and TSSs showed sun protection factors of 8.89 and 14.89,respectively.Conclusions:Sapindus saponaria fruit extracts show strong antioxidant potential and antiglycation activity against bovine serum albumin glycation and AGE formation.Besides,they presented antibacterial activity against Cutibacterium acnes and photoprotective effect against UV-A and UV-B.

A new triterpene saponin from Panax japonicus C.A.Meyer var major(Burk.) C.Y.Wu et K.M.Feng

One new Iriterpene saponin was isolated from Panaxjaponicus C. A. Meyer var major （Burk.） C. Y. Wu et K. M. Feng, and established as oleanolic acid 3-O-[β-D-glucopyranosyl-（1 →2）-β-D-glucuronopyranosyl-6＇-O-n-butyl ester] which showed mod- erate antitumor activities against the A2780 cells and OVCAR-3 cells. Its structure was established by means of spectral data, particularly NMR, including HSQC and HMBC techniques.

Two New Cycloartane Triterpenes from The Leaves of Quercus valiabilis Blume

Two new cycloartane triterpenes were separated from the leaves of Quercus valiabilis Blume. The structures were identified as 4α,14α-dimethyl-9β,19-cycloergost-3α-yl-24-one and 4α,14α-dimethyl-9β,19-cycloergost-24(24′)-en-3α-yl-acetate.

Comprehensive metabolic profiling of Alismatis Rhizoma triterpenes in rats based on characteristic ions and a triterpene database

Alismatis Rhizoma(AR)is widely used in Chinese medicine,and its major bioactive components,triterpenes,reportedly possess various pharmacological activities.Therefore,it is very important to study the metabolism of triterpenes in vivo.However,the metabolism of AR triterpene extract has not been comprehensively elucidated due to its complex chemical components and metabolic pathways.In this study,an ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry method,which was based on the characteristic ions from an established database of known triterpenes,was used to analyze the major metabolites in rats following the oral administration of Alismatis Rhizoma extracts(ARE).As a result,a total of 233 constituents,with 85 prototype compounds and 148 metabolites,were identified for the first time.Hydrogenation,oxidation,sulfate and glucuronidation conjugation were the major metabolic pathways for triterpenes in AR.In addition,the mutual in vivo transformation of known ARE triterpenes was discovered and confirmed for the first time.Those results provide comprehensive insights into the metabolism of AR in vivo,which will be useful for future studies on its pharmacodynamics and pharmacokinetics.Moreover,this established strategy may be useful in metabolic studies of similar compounds.

Cycloartane triterpenes from marine green alga Cladophora fascicularis

Six cycloartanes were isolated from ethanol extract of marine green alga Cladophora fascicularis by column chromatography. Procedure of isolation and description of these compounds are given in this paper. The structures were elucidated as （1）. 24-hydroperoxycycloart-25- en-3β-ol; （2）. cycloart-25-en-3β 24-diol; （3）. 25-hydroperoxycycloart-23-en-3β-ol; （4）. cycloart-23-en-3β, 25-diol; （5）. cycloart-23, 25-dien-3β-ol; and （6）. cycloart-24-en-3β-ol by spectroscopic （MS, 1D and 2D NMR） data analysis. Cycloartane derivatives are widely distributed the alga. All these compounds that have been isolated alga for the first time. in terrestrial plants, but only few were obtained in from terrestrial plants, were found in the marine alga for the first time.

Symplocosionosides A-C, Three Megastigmane Glycosides, a Neolignan Glucoside, and Symplocosins A and B, Two Triterpene Glycosyl Esters from the Leaves of <i>Symplocos cochinchinensis</i>var. <i>Philippinensis</i>

From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Symplocos cochinchinensis var. philippinensis, 12 compounds were isolated. Spectroscopic analyses of compounds 1 - 3 established their structures to be megastig-mane glycosides, named symplocosionosides A-C. The absolute structure of 1 was determined by the modified Mosher’s method. Compound 4 was found to be a neolignan glucoside and named symplocosneolignan. The structures of com-pounds 5 and 6, named symplocosins A and B, were elucidated to be the saponins of hederagenin sugar esters. The structures of the remaining known compounds (7 - 12) were identified by comparison of spectroscopic data with those reported in the literature.

Inhibition of DNA-Topoisomerase I by Acylated Triterpene Saponins from Pittosporum angustifolium Lodd.

Previous phytochemical investigation of the leaves and seeds of Pittosporum angustifolium Lodd.led to the isolation and structural elucidation of polyphenols and triterpene saponins.Evaluation for cytotoxicity of isolated saponins revealed that the predominant structural feature for a cytotoxic activity are acyl substituents at the oleanane aglycon backbone.The present work reports the results of a screening of 10 selected acylated saponins for their potential to inhibit the human DNA-topoisomerase I,giving rise to IC50 values in a range of 2.8-46.5 lM.To clarify the mode of observed cytotoxic action and,moreover,to distinguish from a pure surfactant effect which is commonly accompanied with saponins,these results indicate an involvement of the topoisomerase I and its role as a possible target structure for a cytotoxic activity.In addition,computational predictions of the fitting of saponins to the topoisomerase I-DNA complex,indicate a similar binding mode to that of clinically used topoisomerase I inhibitors.Graphical Abstract Ten acylated triterpene saponins from Pittosporum angustifolium were investigated for their potential to inhibit the human DNA-topoisomerase I and computational predictions of the fitting of saponins to the topoisomerase I-DNA complex were carried out.

Antitumor triterpene saponins from Anemone flaccida

A new triterpenoid saponin, 3-O-[（6′-butyryl）-β-D-glucopyranosyl]-28-O-[α-L-rhamnopyranosyl-（1→4）-β-D-glucopyranosyl-（1→6）-β-D-glucopyranosyl] oleanolic acid, as well as three known triterpenoid saponins were isolated from the rhizomes of Anemone flaccida. Their structures were elucidated by spectroscopic methods. These compounds showed significant antitumor activities.

Two triterpene glycosides from the sea cucumber Bohadschia marmorata Jaeger

Further studies on the sea cucumber Bohadschia marmorata Jaeger led to the isolation of a new holostan-type triterpene glycoside,Marmoroside C（1）together with a known triterpene glycoside（2）.On the basis of spectroscopic analyses,including two- dimensional NMR techniques,and chemical reactions,the structure of the new triterpene glycoside was elucidated as 3-O-[3-O- methyl-β-D-glucopyranosyl-（1→3）-β-D-glucopyranosyl-（1→4）-β-D-quinovopyranosyl-（1→2）-4-O-sodium-sulfato-β-D-xylo- pyranosyl]-25-acetoxy-22-oxo-9（11）-holostene-3β,12α,17α-triol.

Two new olean-type triterpene fatty esters from Scorzonera mongolica

Two new triterpene fatty esters, 3β-tetradecanoyl moradiol 1 and 3β-dodecanoyl moradiol 2, were isolated from Scorzonera mongolica. Their structures were elucidated as 3β-tetradecanoyloxy-28-hydroxylolean-18-ene and 3β-dodecanoyl-28-hydroxyl-olean-18-ene on the basis of IR, MS, 1D NMR and extensive 2D NMR spectroscopic analyses.

Anti‑inflammatory and Cytotoxic Triterpenes from the Rot Roots of Panax notoginseng

Four new protopanaxatriol-type triterpenes(1-2)and glucosides(3-4),were isolated from the rot roots of Panax notoginseng(Burk.)Chen,along with four known ones(5-8).Their structures were elucidated on the basis of extensive spectroscopic analysis(HRESIMS,NMR,UV,IR,and OR)and acidic hydrolysis.The possible transformation pathway of these compounds were also speculated from ginsenoside Rg_(1).Compound 1,with a uniqueα,β-unsaturated ketene in its side chain,showed significant inhibitory effects against NO production on Murine macrophage cells(IC_(50)=4.12±0.20μM)and comparable cytotoxicities against five human cancer cell lines(myeloid leukemia HL-60,lung cancer A-549 cells,hepatocellular carcinoma SMMC7721,breast cancer MCF-7,and colon cancer SW480)to positive control,cisplatin(DDP).

17-Dehydroxyholothurin A, a New Sulfated Triterpene Glycoside from Sea Cucumber Holothuna impatiens

Abstract： A new sulfated triterpene glycoside named as 17-dehydroxyholothurin A 1 was isolated from the sea cucumber Holothuria impatiens. Its structure was elucidated on the basis of spectroscopic data （2D NMR and MS） and chemical evidence. Compound 1 showed cytotoxic activity against cancer cell lines MKN-28, MFC-7, KB, HL-60 and Hep G2 with IC50 values of 1.98, 4.53, 2.01, 4.69 and 2.80 ×10^-6 tool/L, respectively.