Immunomodulatory activity of a lupane triterpenoid ester isolated from the eastern Nigeria mistletoe,Loranthus micranthus(Linn)

Objective:To provide further evidence for the ethnomedicinal use of the Eastern Nigeria mistletoe,Loranthus micranthus(L.micranthus),as an immunostimulant.Methods:Solvent fractions from the crude extract of the mistletoe plant was obtained and screened by the cell mediated delayed type hypersensitivity reaction(DTHR) model in mice.Then the immunomodulatory potentials of a major lupane triterpenoid ester isolated from an active hexane fraction of the Eastern Nigeria mistletoe was investigated.Three lupeol-based triterpenoid esters: 7β15α-dihydroxyl-lup-20(29)-ene-3β-palmitate(Ⅰ),7β,15α-dihydroxyl-lup-20(29)- ene-3β-stearate(Ⅱ) and 7β,15α-dihydroxyl-lup-20(29)-ene-3β-decadecanoate(Ⅲ) were isolated from the plant leaves epiphyting on a local kola nut tree and were characterized. Compound 1 was subjected to cell proliferation studies using C57H1/6 splenocvtes at three dose levels(5.25 and 100μg/mL) in presence of controls.Furthermore,the effect of this compound on IL-8 receptor expression was evaluated at three doses(1,5 and 10μg/mL) using the real time polymerase chain reaction assay.Results:This triterpenoid ester produced some enhancement of the splenocytes at the tested doses but at doses higher than 5μg/mL caused inhibition of the IL-8 receptor expression.Conclusions:The present findings support the ethnomedicinal use of the Eastern Nigeria Mistletoe in the management of diseases affecting the immune system.The trilerpenoid(s) have some immunomodulatory abilities on splenocytes and IL-8 receptors and may partly account lor the overall immunomodulatory activity of this plant.

Chemical derivatization strategies for enhancing the HPLC analytical performance of natural active triterpenoids

Triterpenoids widely exist in nature,displaying a variety of pharmacological activities.Determining triterpenoids in different matrices,especially in biological samples holds great significance.High-performance liquid chromatography(HPLC)has become the predominant method for triterpenoids analysis due to its exceptional analytical performance.However,due to the structural similarities among botanical samples,achieving effective separation of each triterpenoid proves challenging,necessitating significant improvements in analytical methods.Additionally,triterpenoids are characterized by a lack of ultraviolet(UV)absorption groups and chromophores,along with low ionization efficiency in mass spectrometry.Consequently,routine HPLC analysis suffers from poor sensitivity.Chemical derivatization emerges as an indispensable technique in HPLC analysis to enhance its performance.Considering the structural characteristics of triterpenoids,various derivatization reagents such as acid chlorides,rhodamines,isocyanates,sulfonic esters,and amines have been employed for the derivatization analysis of triterpenoids.This review comprehensively summarized the research progress made in derivatization strategies for HPLC detection of triterpenoids.Moreover,the limitations and challenges encountered in previous studies are discussed,and future research directions are proposed to develop more effective derivatization methods.

Four new lanostane triterpenoids featuring extendedπ-conjugated systems from the stems of Kadsura coccinea

Four new 14(13→12)-abeolanostane triterpenoids featuring extendedπ-conjugated systems,kadcoccitanes E-H(1-4),were obtained from the stems of Kadsura coccinea through using a HPLC−UV-guided approach.Their structural and configurational determination was accomplished through extensive spectroscopic analysis coupled with quantum chemical calculations.Kadcoccitanes E-H were tested for their cytotoxic activities against five human tumor cell lines(HL-60,A-549,SMMC-7721,MDA-MB-231,SW-480)but none of them exhibited activities at the concentration 40μM.

A New Lupane from the Resin of Boswellia carterii

A new lupane-type triterpene was isolated from the resin of Boswellia carterii Birdw. Based on the spectral methods, its structure was elucidated as lup-20(29)-ene-3a-acetoxy-24-oic acid.

A NEW BACCHARANE-TYPE TRITERPENOID ISOLATED FROM THE ROOTS OF SAUSSUREA LAPPA C.B.CLARKE

A new baccharane-type triterpene, 3-acetoxy-9(11)-baccharene(1),as well as a known compound, a-amyrin(2), has been isolated from the ether extract of the roots of Saussurea lappa C. B. Clarke. The structure of the new compound was identified by spectrum analysis.

Two New Tirucallane-Type Triterpenoid Saponins from Sapindus mukorossi

Two new tirucallane-type triterpenoid saponins, Sapimukoside A (1) and Sapimukoside B (2), were isolated from the roots of Sapindus mukorossi Gaertn. On the basis of spectroscopic and chemical evidence, their structures were elucidated to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-glucopyranosyl-21, 23R-epoxyl tirucall-7, 24R-diene-3beta, 21-diol (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl-21, 23R-epoxyl tirucall-7, 24R-diene-3beta, 21-diol (2).

A New Triterpenoid Saponin from Rhaponticum uniflorum (Compositae)

A new triterpenoid saponin, namely unifloroside, together with five known compounds, was isolated from Rhaponticum uniflorum (L.) DC. The structure of the new triterpenoid saponin was elucidated as 3_O_ α_L_arabinopyranosyl_urs_9(11),12_dien_28_oic acid β_D_glucopyranosyl ester mainly by using 1D, 2D_NMR techniques and chemical methods.

A new bidesmoside triterpenoid saponin from Stauntonia chinensis

A new bidesmoside triterpenoid saponin, named stauntoside C1 （1） has been isolated from Stauntonia chinensis. Its structure was established by means of spectral and chemical methods. C 2009 Guo Ping Zhou. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

A new cucurbitane triterpenoid from Momordica charantia

One new cucurbitane-type triterpenoid saponin, 5β,19-epoxycucurbita-6,23-diene-3β,19,25-triol-3-O-β-D-allopyranoside （1）,named momordicoside P was isolated from the fresh fruits ofMomordica charantia. The structure of the saponin was elucidated by spectral methods, including 2D-NMR spectra.

Cucurbitane triterpenoids from Hemsleya penxianensis

Two new cucurbitacins,jinfushanencins A(1)and B(2),seven new cucurbitane glycosides,jinfushanosides E-K(3-9),along with nine known analogues,were obtained from the tubers of Hemsleya penxianensis.Their structures were elucidated on the basis of extensive spectroscopic and chemical methods.Selected isolates were tested their anti-HIV-1 activities,and compound 5 showed weak anti-HIV-1 in C8166 cell(EC50=5.9μg/mL)with a selectivity index of 13.5.

Diacylated Triterpenoid Saponin from Silene szechuensis

A new triterpenoid saponin, named silenoside, with sugar chains esterified by two different acyl groups was isolated from Silene szechuensis. Its structure was elucidated by chemical and spectral methods.

Studies on Triterpenoid Saponins of Seeds of Aesculus chinensis Bunge var. chekiangensis (Hu et Fang) Fang

Aim To study the saponin constituents of the seeds of Aesculus chinensis Bunge var. chekiangensis (Hu et Fang) Fang. Methods Compounds were separated and purified by macroreticular resin column chromatography and high-performance liquid chromatography. Their structures were elucidated by spectroscopic and hydrolysis analysis. Results Six compounds were isolated from the 70% ethanolic extracts. They were identified as escins IVc, IVd, Ia, Ib, isoescins Ia and Ib, respectively. Conclusion The above compounds were obtained from the seeds of Aesculus chinensis Bunge var.chekiangensis (Hu et Fang) Fang for the first time.

Two New Triterpenoids from Saussurea petrovii

Two new taraxastane-type triterpenes. 3 beta. 21 beta -dihydroxyl-20(30)-en-taraxastane 1 and 3 beta. 30-dihydroxy-20(21)-en-taraxastane 2. were isolated from Saussurea petrovii. Their structures were elucidated by spectral methods (EIMS. IR. 1D and 2DNMR).

Two new tirucallane triterpenoids from Aphanamixis grandifolia

Two new tirucallane triterpenoids,2a-ethoxy-2,3-secotirucalla-2,29-epoxy-7-ene-23-oxo-3-oic acid(1)and(23E)-2a-hydroxytirucalla-7,23,25-triene-3-one(2),along with the known 2,3-secotirucalla-2,3;2,29-diepoxy-7-ene-3,23-dione(3),were isolated from the leaves and twigs of Aphanamixis grandifolia.Their structures were elucidated by extensive NMR and MS data,and compound 3 was further confirmed by X-ray crystal diffraction analysis.Antimicrobial activities and insecticidal activities of these three compounds were also evaluated.Compound 1 showed good antimicrobial activity against Staphylococcus aureus with the MIC value of 1.56μg/mL,while compounds 1 and 2 showed insecticidal activity at 100 ppm,with the corrected mortality 79.1%and 60.6%,respectively.

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).

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.

A New Triterpenoid from Doellingeria scaber

A new oleanane-type triterpene was isolated from the roots of Doellingeria scaber. Its structure was identified as 3-oxo-16a-hydroxy-olean-12-en-28-oic acid based on 1D and 2D NMR spectroscopy and X-ray analysis.

Four 14(13→12)‑Abeolanostane Triterpenoids with 6/6/5/6‑Fused Ring System from the Roots of Kadsura coccinea

Four new rearranged 6/6/5/6-fused lanostane-type triterpenoids,kadcoccitanes A-D(1-4),were isolated from the roots of Kadsura coccinea,and their structures were mainly elucidated by comprehensive analysis of their spectroscopic data.Additionally,the structure of 1 was ambiguously verifed by single-crystal X-ray difraction,while the structure of 2,which features a novel 8,16-epoxy motif,was validated by quantum chemical calculation of NMR parameters and ECD spectrum.Moreover,1 and 4 were found to exhibited anticoagulant activity,while 3 and 4 were found to possess anti-platelet aggregation activity.

Cytotoxic Cycloartane Triterpenoid Saponins from the Rhizomes of Cimicifuga foetida

To enrich the bioactive cycloartane triterpenoid glycoside named actein and find out more cytotoxic cycloartane triterpenes,a phytochemical study of Cimicifuga foetida was conducted.113 g(0.17%)actein was purified by recrystallization while eight cycloartane-type triterpenes(1-8)were isolated from the mother liquid.The chemical structures of new compounds(1-4)were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses.Moreover,new compounds showed moderate and broad-spectrum cytotoxicity against 5 human cancer cell lines with IC_(50) values ranging from 4.02 to 15.80μM.

A new cycloartane triterpenoid from the leaves and stems of Fritillaria hupehensis

A new triterpenoid has been isolated from the leaves and stems of Fritillaria hupehensis Hsiao et K.C. Hsia. Its structure was established as （2329-9,19-cycloart-23-ene-3α,25-diol 1 through chemical and spectroscopic studies including 2D NMR. Another known triterpenoid 9,19-cycloart-25-ene-313,24ζ-diol 2 was also isolated.