Chemical constituents and biological activities from branches of Colubrina asiatica

Sixteen compounds were isolated from a Thai medicinal plant, Colubrina asiatica. The isolated compounds were elucidated on the basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene acids (1–6), five steroids (7–11), one benzoic acid derivative (12), two peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin (16). Compounds 3 and 10 showed antimalarial activity against Plasmodium falciparum. Compound 5 showed antimycobacterial activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak cytotoxicity against cancer cell lines. Compounds 1–15 have been isolated for the first time from this plant.     

Three New Cycloartane Triterpene Glycosides from Actaea asiatica

Three new cycloartane triterpene glycosides were isolated from the rhizomes of Actaea asiatica. Their structures were elucidated as 25-ethoxyl-cimigenol-3-O-β-D-xylopyranoside 1, 2'-O-acetyl soulieoside C 2, 2'-O-acetyl cimiracemoside M 3.     

Coumarins and alkaloids from the roots of Toddalia asiatica

The EtOAc and MeOH extracts of the roots of Toddalia asiatica Lam. were investigated for the roots’ chemical constituents. Two new compounds including 2′R-acetoxytoddanol (1) and 8S-10-O-demethylbocconoline (3) as well as 15 known compounds were isolated. Compound 10 showed strong cytotoxicity against KB cells with an IC₅₀ value of 2.60 μg/mL, which is nearly equal to the ellipticine standard, but showed no activity against Vero cells. Alkaloid 3 displayed weak cytotoxicity against the KB cell line with an IC₅₀ value of 21.69 μg/mL.     

Catomentosaponin,a new triterpene saponin from the roots of Catunaregam tomentosa

A new triterpene saponin, catomentosaponin (1) and 11 known analogues (2–12) were isolated from the roots of Catunaregam tomentosa. The structures of 1–12 were determined on the basis of extensive NMR and MS data analysis. The sugar residues were identified by co-TLC and HPLC analysis after hydrolysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines. Compound 2 showed moderate cytotoxicity against KB cell with IC₅₀ value of 24.84 μM.     

Two new lupene-type triterpenoids from the roots of Liquidambar formosana

Two new lupene-type triterpenoids, 3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (1) and 2α-acetoxyl-3β,6β-dihydroxylup-20(29)-en-28-oic acid β-glucopyranosyl ester (2), along with 18 known compounds, were isolated from Liquidambar formosana. The structures were elucidated on the basis of spectroscopic methods, including UV, IR, ESIMS, 1D- and 2D-NMR experiments, as well as by comparison of the spectral data with those of related compounds.     

Two New Pentacyclic Triterpenoids from Centella asiatica

Two new pentacyclic triterpenoids, named centelloside D ( 1 ) and centelloside E ( 9 ), together with the seven known compounds 2 – 8 , were isolated from the whole plants of Centella asiatica. Compound 5 was reported for the first time from this genus. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D ‐ and 2D ‐NMR, and HR‐MS experiments, and by comparison with literature data. Compounds 1 – 4, 6 , and 8 did not show any cytotoxicity against L929 (mouse embryonic fibroblast).     

Saponins from the roots of Chenopodium bonus-henricus L.

Two new glycosides of phytolaccagenin and 2β-hydroxyoleanoic acid, namely bonushenricoside A (3) and bonushenricoside B (5) together with four known saponins, respectively compounds 3-O-L-α-arabinopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (1), 3-O-β-glucuronopyranosyl-2β-hydroxygypsogenin-28-O-β-glucopyranosyl ester (2), 3-O-β-glucuronopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (4) and 3-O-β-glucuronopyranosyl-medicagenic acid-28-β-xylopyranosyl(1→4)-α-rhamnopyranosyl(1→2)-α-arabinopyranosyl ester (6) were isolated from the roots of Chenopodium bonus-henricus L. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, IR and HRMS). The MeOH extract and compounds were tested for cytotoxic activity on five leukemic cell lines (HL-60, SKW-3, Jurkat E6-1, BV-173 and K-562). In addition, the ability of metanolic extract and saponins to modulate the interleukin-2 production in PHA/PMA stimulated Jurkat E6-1 cells was investigated as well.     

Two new 14, 15-secopregnane-type steroidal glycosides from the roots of Cynanchum limprichtii

Two new steroidal glycosides 1 and 2, along with three known ones (3–5), were isolated from the 95% ethanol extract of the roots of Cynanchum limprichtii Schltr. The structure of the new compounds was elucidated as 3-O-α-L-diginopyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-thevetopyranosyl-14, 16:15, 20:18, 20-triepoxy-14, 15-secopregn-4, 6, 8 (14)-triene (1) and 3-O-α-L-cymaropyranosyl-(1→4)-β-D-digitoxopyranosyl- (1→4)-β-D-3-demethyl-2-deoxythevetopyranosyl-14, 16: 15, 20: 8, 20-triepoxy-14, 15-secopregn-5, 8 (14)-diene (2) on the basis of spectroscopic analysis together with acidic hydrolysis. All compounds showed cytotoxic activity against the human cancer cell line HL60, with IC₅₀ values of 55.36, 65.41, 17.88, 17.68 and 33.5 μM, respectively. While, only compound 3 showed cytotoxicity against the Caco-2 cell line, with an IC₅₀ value of 67.47 μM.     

UHPLC–Q-ToF-MS-guided enrichment and purification of triterpenoids from Centella asiatica (L.) extract with macroporous resin

The aim of the study is to standardize a simple and an effective extraction method for industrial preparation of Centella asiatica (L.) extract rich in triterpenoids. Macroporous resin purification process was adapted to enrich the triterpenes extracted from the herb. A sensitive analytical method with good resolution, linearity, and a shorter run time of 10?min was developed in ultra high-performance liquid chromatography–quadrupole-time-of-flight mass spectrometer for monitoring the triterpene (madecassoside, asiaticoside, madecassic acid, and asiatic acid) content at each stage of the extraction process. The standardized process could enrich the triterpene, madecassoside in the product up to a purity of 72.51% with overall recovery of the compound to 90.79%. A purified form of asiaticoside with a purity of 85% was obtained by dealcoholization and precipitation process exploiting the differential water solubility of the two major triterpenes. The binding and recovery of the aglycones (madecassic acid and asiatic acid) were observed to be poor, and hence the overall recovery of aglycones by this process was found to be very low. The purified triterpenoids were also confirmed by the ¹H NMR. Thus, the results suggest that the standardized process can be converted to industrial-scale preparation of high-value C. asiatica (L.) products rich in madecassoside or asiaticoside.     

Antimalarial and cytotoxic activities of pregnene-type steroidal alkaloids from Holarrhena pubescens roots

The phytochemical investigation of an alkaloidal extract of Holarrhena pubescens roots led to the isolation and identification of a new pregnene-type alkaloid, mokluangin D (1), together with nine known steroidal alkaloids (2–10). The structure of the new metabolite was determined on the basis of spectroscopic analyses including 1D- and 2D-NMR spectroscopy and mass spectrometry. Compounds 3 and 4 showed potent antimalarial activity against Plasmodium falciparum K1 stain with IC₅₀ values of 1.2 and 2.0 μM, respectively, and showed weak cytotoxic activity against the NCI-H187 cell line with IC₅₀ values of 27.7 and 30.6 μM, respectively. The substituent groups at C-3 and the carbonyl group at C-18 are important for the activity against the P. falciparum K1 stain.     

Two new triterpenoids from Photinia serrulata

Two new triterpenoids, 2alpha,3beta,11alpha,13beta-tetrahydroxy-12-ketooleanan-28-oic acid(1) and 3beta-hydroxy-12-keto-9(11)-ursen-28,13beta-olide (2) were isolated from the leaves ofPhotinia serrulata. Their structures were identified by spectral methods. Compounds 1 and2 were assessed for cytotoxic activity against three human tumor cell lines (A-549, HCT-8,and BEL-7402), and they showed no cytotoxic effects at concentrations up to 5microg/mL.     

Two new triterpenoids from Gypsophila oldhamiana

Two new triterpenoids (1–2) were isolated and elucidated from the roots of Gypsophila oldhamiana, together with four known triterpenoids (3–6). Their structures were identified to be 3β-hydroxyolean-13(18)-ene-23, 28-dioic acid (1), 3β, 12α-dihydroxy-23-carboxyolean-28, 13β-olide (2), 3β, 16α-dihydroxy-23-oxoolean-13(18)-en-28-oic acid (3), gypsogenin (4), quillaic acid (5) and gypsogenic acid (6) by spectral methods. All compounds were tested for their cytotoxicities against human tumour cell lines (lung cancer H460 and gastric cancer SGC-7901) and for their antiangiogenic effects using a zebra fish model. All compounds showed interesting antiangiogenic activities and the significant cytotoxicities against H460.     

Two new triterpenoids from Zygophyllum eurypterum

Two new triterpenoids trivially named as atriplicoide A and B were isolated from the n-BuOH extract of the whole plant of Zygophyllum eurypterum. Based on EI-MS, IR, 1H- and 13C-NMR, and 2D-NMR (HMQC, HMBC, COSY and NOESY) data, the structures of the new compounds were determined as 30-carboxy-3beta,24-dihydroxy-urs-28,13beta-lactam-N-acetate (1) and 3beta,24-dihydroxyursan-28,13beta-olide (2).     

Two new triterpenoids from Nauclea officinalis

Two new triterpenoids and three 27-nor-triterpenoids were isolated from the stems (with bark) of Nauclea officinalis. Their structures were identified to be 2β,3β,19α,23-tetrahydroxy-urs-12-en-28-oic acid (1), 2β,3β,19α,23-tetrahydroxy-urs-12-en-28-O-[β-d-glucopyranosyl (1-2)-β-d-glucopyranosyl] ester (2), pyrocincholic acid 3β-O-α-l-rhamnopyranoside (3), pyrocincholic acid 3β-O-α-l-rhamnopyranosy1-28-O-β-d-glucopyranosyl ester (4), pyrocincholic acid 3β-O-α-l-rhamnopyranosy1-28-O-β-d-glucopyranosyl-(1-6)-β-d-glucopyranosyl ester (5) by spectroscopic methods including 1D, 2D NMR and HR-MS analyses. The cytotoxic activity of 1–5 against lung cancer A-549 cells was also investigated.     

Two new triterpenoids from Psidium guajava

Two new triterpenoids,named as 2 α,3 β,23-trihydroxylurs-12,20(30)-dien-28-oic acid β-D-glucopyranoside(1),and 2 α,3 β,6 β,20 β,23,30-hexahydroxyurs-12-en-28-oic acid(2),together with four known triterpenoids were isolated from the leaves of Psidium guajava L.Their structures were elucidated on the basis of mass and spectral evidence.     

New Pentacyclic Triterpenoids from Centella asiatica

Three new pentacyclic triterpenoids, named centellasaponins G, H, and F ( 1 – 3 , resp.), together with four known compounds, 4 – 7 , were isolated from the whole plants of Centella asiatica. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D‐ and 2D‐NMR and HR‐MS experiments, and by comparison with literature data.     

Two new triterpenoids from the fungus Diplodia cupressi

Abstract

One new pentanortriterpenoid, 23,24,25,26,27-pentanorlanost-7,9(11)-dien-3β,22-diol (1), one new triterpenoid, lanost-8-en-3β,22S,23S-triol (2), together with the known triterpenoid, 23,24,25,26,27-pentanorlanost-8-en-3β,22-diol (3), were obtained from culture of the fungus Diplodia cupressi associated with the moss Polytrichum commune. The structures of the new compounds were elucidated by extensive spectroscopic techniques including HR-ESIMS and 1?D and 2?D NMR experiments. The cytotoxicity of these compounds against human cancer cell lines (A549, Hep G2, Hepa 1c1c7, and Hela) was evaluated and compound 2 exhibited weak inhibitory activity with IC₅₀ value of 35.0?±?2.3?μM against the proliferation of the Hepa 1c1c7 cells.     

A new cycloartane triterpene glycoside from Souliea vaginata

A new cycloartane-type triterpene glycoside, namely soulieoside M (1), and one known compound, beesioside I (2), were isolated from the ethanolic extract of the rhizomes of Souliea vaginata. Their structures were determined spectroscopically and compared with previously reported spectral data. Compounds 1 and 2 were evaluated for their cytotoxic activities against three human cancer cell lines.     

Two new triterpenoids from Gardenia jasminoides fruits

A new cycloartane triterpenoid, named gardenolic acid C (1), a new ursane triterpenoid, named 3β,16β,21β,23,24-pentahydroxy urs-12,18,20-trien-28-oic acid γ-lactone (2), together with three know triterpenoids, gardenolic acid A (3), gardenolic acid B (4), and 3α,16β,23,24-tetrahydroxy-28-nor-ursane-12,17,19,21-tetraen (5) were isolated from the fruits of Gardenia jasminoides Ellis. The structures of these compounds were elucidated by analyses of spectroscopic data. All isolates were evaluated for their neuroprotective effects in vitro.

     

Two new lanostane triterpenoids from Abies sachalinensis

The continuous chemical investigation on the ethyl acetate (EtOAc) soluble fraction of the MeOH extract afforded two new lanostane triterpenoid derivatives including one with a rearranged lanostane skeleton. They were identified as 3,4-seco-8-(14→,13R)abeo-17,13-friedo-9β-lanosta-4(28), 7,14(30),24-tetraen-26,23-olide-23-hydroxy-3-oic acid (1) and 7,14-mariesa-dien-3a-hydroxy-25-methoxy-26-oic acid (2). Structural determination of these compounds were carried out by the spectral studies especially by the two digital (2D)-NMR and high-resolution MS experiences.