Analgesic, anti-inflammatory, and CNS depressant activities of new constituents of Nepeta clarkei

Two new pentacyclic triterpenes named kirmanoic acid (1) and kurramanoic acid (2) have been isolated from the chloroform-soluble portion of the whole plant of Nepeta clarkei Hook. The structures of the two new compounds were assigned on the basis of their 1H and 13C NMR spectra including two-dimensional NMR techniques such as COSY, HMQC, and HMBC experiments. Kirmanoic acid (1) was investigated for analgesic, anti-inflammatory, and CNS depressant activities. Interestingly kirmanoic acid (1) showed strong analgesic activity than standard drug in acetic induced writhing and formalin tests. Similarly kirmanoic acid (1) also showed strong anti-inflammatory activity than its standard drug. The gross behavioral study of kirmanoic acid (1) revealed that it exhibited mild CNS stimulant and muscle relaxant in the mice. Compound 1 showed a slight increase in Locomotor activity and possesses the antidepressant effect.     

Phomopsidone A,a novel depsidone metabolite from the mangrove endophytic fungus Phomopsis sp. A123

One novel pentacyclic depsidone containing an oxetane unit, phomopsidone A (1), together with the reported excelsione (also named as phomopsidone) (2), and four known isobenzofuranones (3–6) were isolated from the mangrove endophytic fungus Phomopsis sp. A123. Their structures were elucidated by 1D and 2D NMR spectroscopic analysis and high resolution mass spectrometry. The bioactivity assays showed that these compounds possess cytotoxic, antioxidant, and antifungal activities.     

Cytotoxic 9,19-cycloartane triterpenes from the aerial parts of Cimicifuga yunnanensis

Six new 9,19-cycloartane triterpenes (1–6) were isolated from the aerial parts of Cimicifuga yunnanensis. The new chemical structures were determined by extensive analyses of 1D and 2D NMR spectroscopy. Compounds 1 and 2 are the first 9,19-cycloartane triterpenes characterized by CH₃-18 shifting from C-13 to C-12 in the Cimicifuga spp. The evaluation of inhibition activity against human HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines indicated that compounds 1–6 showed different levels of cytotoxic activities with IC₅₀ values ranging from 1.2 to 27.8 μm.     

A new 1,3-diketofriedelane triterpene from Salacia verrucosa

A new 1,3-diketofriedelane triterpene, 21α-hydroxyfriedelane-1,3-dione (1) together with six known friedelane triterpenes, 30-hydroxyfriedelane-1,3-dione (2), friedelane-1,3-dione (3), 26-hydroxyfriedelane-1,3-dione (4), friedelin (5), 21α-hydroxy-D:A-friedo-olean-3-one (6) and kokoonol (7), were isolated from the stems of Salacia verrucosa (Celastraceae). The structures of these triterpenes were characterized by spectroscopic methods (IR, MS and NMR). Compound 3 was strongly cytotoxic against SW620 cell line, whereas compounds 4 and 6 were moderately active against SW620, HepG2 and KATO-III cancer cell lines.     

Hepatoprotective effect of lupeol and lupeol linoleate on tissue antioxidant defence system in cadmium-induced hepatotoxicity in rats.

Lupeol, a pentacyclic triterpene and its ester derivative, lupeol linoleate, were investigated for their possible hepatoprotective effect against cadmium-induced toxicity in rats. Cadmium intoxicated rats showed elevated levels of malondialdehyde (basal and induced), and decreased levels of antioxidants and antioxidising enzymes in the liver. The oral administration of triterpenes (150 mg/kg, once a day for 3 days before injection of cadmium chloride) changed the tissue redox system by scavenging the free radicals and by improving the antioxidant status of the liver. Lupeol linoleate had a better effect on the antioxidant status of the liver, when compared to lupeol.     

Three new ursane-type triterpenes from the leaves of Rehmannia glutinosa

Three new ursane-type triterpenes, glutinosalactone A–C (1–3), were isolated from the 50% aqueous acetone extract of the leaves of Rehmannia glutinosa. Their structures were elucidated on the basis of spectral analysis (IR, NMR and MS spectroscopy). The cytotoxic effects of compounds 1–3 against three human cancer cell lines (MCF-7, MG63 and HepG2) were also evaluated. Compound 3 showed cytotoxic activities with IC₅₀ values of 8.35–39.25 μM.     

Study on the hypoglycemic activities and metabolism of alcohol extract of Alismatis Rhizoma

The Alisma rhizoma is widely used in the therapy of diabetes in traditional folk medicine of China. Compositional analysis of the alcohol extract of Alismatis Rhizoma (AEA) revealed that the eight compounds gotten from AEA are all belonging to protostane-type triterpenes. The AEA and compounds were incubated with 3T3-L1 preadipocytes, glucose level in the 3T3-L1 adipocytes culture medium and lipid content in 3T3-L1 adipocytes were measured, and analysis of alpha-glucosidase inhibition of AEA and compounds. At the same time, the uptake of AEA by 3T3-L1 adipocytes and the metabolism of AEA in SD rats were analyzed by HPLC-ESI/MS. As result, AEA increased glucose uptake in 3T3-L1 adipocyte model, not increase adipogenesis; AEA inhibited alpha-glucosidase activity; alisol A-24-aceate (8) was absorbed by 3T3-L1 adipocytes; and two compounds were detected in blood and three were detected in urine in SD rats. So AEA had protostane-type triterpenes, these type compounds in AEA may have hypoglycemic activity via inhibition of alpha-glucosidase activity and promotion of glucose uptake. In contrast to the anti-diabetic drug thiazolidinediones, they did not induce adipogenesis, avoiding the displeased effects of rosiglitazone.     

Levels of lantadenes, bioactive pentacyclic triterpenoids, in young and mature leaves of Lantana camara var. aculeata.

Levels of the lantadene pentacyclic triterpenes were quantified in young and mature leaf samples of Lantana camara var. aculeata, by HPLC. The amount of different lantadenes (mg/100 g dry wt.) in young and mature leaf samples, respectively, was: lantadene A, 491.5 +/- 6.3, 805.9 +/- 52.8; lantadene B, 347.0 +/- 3.0, 522.3 +/- 37.1; lantadene C, 191.3 +/- 10.3, 424.8 +/- 39.1; lantadene D, 49.7 +/- 5.3, 177.4 +/- 19.0; reduced lantadene A, 19.1 +/- 2.3, 28.7 +/- 4.5; reduced lantadene B, 13.0 +/- 1.3, 18.6 +/- 1.2; and 22 beta-hydroxyoleanonic acid, 82.5 +/- 11.4, 167.7 +/- 30.1.     

Antiviral lanostanoid triterpenes from the fungus Ganoderma pfeifferi

Ganodermadiol, lucidadiol and applanoxidic acid G were isolated as first triterpenes from the European Basidiomycete Ganoderma pfeifferi. The compounds show antiviral activity against influenza virus type A and HSV type 1.     

Control of urinary risk factors of stones by betulin and lupeol in experimental hyperoxaluria.

Urolithiasis, the process of formation of stones in the kidney and the urinary tract, is the major clinical manifestation of hyperoxaluria. Crystal deposition, as indicated by increased stone-forming constituents in urine, such as calcium, oxalate and uric acid, and decreased concentration of inhibitors, such as magnesium and glycosaminoglycans, was observed in pyridoxine-deficient hyperoxaluric rats. Renal tubular damage was indicated by increased excretion of enzymes such as alkaline phosphatase, lactate dehydrogenase, gamma-glutamyl transferase, beta-glucuronidase and N-acetyl glucosaminidase. Fibrinolytic activity was found to be reduced. Administration of pentacyclic triterpenes such as lupeol and its structural analogue betulin to hyperoxaluric rats minimised the tubular damage and reduced the markers of crystal deposition in the kidneys. In this connection, lupeol was found to be more effective than betulin.     

Cytotoxic pentacyclic triterpenes from Combretum nigricans

A new pentacyclic triterpene, 11alpha-acetoxy-20,24-epoxy-25-hydroxy-dammar-3-one (1), has been isolated from the African tree Combretum nigricans, together with the known corresponding diol, 20,24-epoxy-11alpha, 25-dihydroxy-dammar-3-one (2). They are responsible, at least in part, for the cytotoxic activity of the methanolic extract of the plant.     

Antibacterial triterpenes from the threatened wood-decay fungus Fomitopsis rosea

From a biologically active extract from the fungus Fomitopsis rosea, two new lanostane triterpenes were isolated, 3α-(3′-butylcarboxyacetoxy)oxepanoquercinic acid C 1 and 3α-hydroxy-24-methylene-23-oxolanost-8-en-26-carboxylic acid 2, along with three known triterpenes, 3–5, and the epidioxy sterol derivative 6. The structures of the compounds were elucidated based on their spectral properties. All triterpenes demonstrated antibacterial activity against S. aureus but possessed no antiradical activity against DPPH radicals.     

Larvicidal and growth inhibition of the malaria vector Anopheles stephensi by triterpenes from Dysoxylum malabaricum and Dysoxylum beddomei

Secondary metabolites from Dysoxylum malabaricum and Dysoxylum beddomei were tested against mature and immature stage of the mosquito vector Anopheles stephensi under laboratory conditions. The triterpenes 3beta,24,25-trihydroxycycloartane and beddomeilactone from D. malabaricum and D. beddomei showed strong larvicidal, pupicidal and adulticidal activity. They also affected the reproductive potential of adults by acting as oviposition deterrents. The highest concentration tested (10 ppm) of both compounds evoked more than 90% mortality and oviposition deterrence.     

Two new diterpene derivatives from Euphorbia lunulata Bge and their anti-proliferative activities

A new ent-abietane-type diterpene lactone (1) and a new jatrophane-type diterpenoid (2), together with twelve known compounds including three diterpenes (3–5), five triterpenes (6–10) and four sterides (11–14) were isolated from the ethanol extract of the whole plant of Euphorbia lunulata Bge. The structure of compounds 1 and 2 was elucidated on the basis of 1D and 2D NMR spectra and the HR-ESI-MS data. The structure of compound 2 was further analyzed by an X-ray crystallographic study. The in vitro anti-proliferative activities against MCF-7 and NCI-H460 cell lines for compounds 1–5 (diterpene) were evaluated. The results showed marked activity for compound 1 against the two cell lines with the IC₅₀ values 19.5 (NCI-H460) and 18.6 (MCF-7) μM, while for cis-platinum (a positive cytotoxic control agent) 29.7 (NCI-H460) and 27.7 (MCF-7) μM. Compounds 2–5 exhibited moderate cytotoxic activities for the two cell lines with the IC₅₀ values ranging from 32.1 to 58.2 μM.     

Oleanene triterpenes from Sedum lineare Thunb

One new olean-13(18)-ene-3,12,19-trione (1), and two known oleanene triterpenes δ-amyrone (2), and δ-amyrine acetate (3) were isolated from the petroleum ether fraction from an alcoholic extract of the whole plant of Sedum linear Thunb. The new compound was characterized by means of spectroscopic methods including 1D, 2D NMR and HR-ESI–MS, and was further confirmed by X-ray diffraction analysis. The known ones were established on the basis of comparing their NMR data with those of the corresponding compounds in the literature. In addition, the inhibitory effects of the compounds isolated on the TNF-α and NO production were examined in vitro.     

Stereochemical determination of new cytochalasans from the plant endophytic fungus Trichoderma gamsii

Three new cytochalasans, trichalasins E (1), F (2) and H (7), together with four known analogues, trichalasin C (3), aspochalasin K (4), trichalasin G (5) and aspergillin PZ (8), were isolated from one endophytic fungus Trichoderma gamsii inhabiting in the traditional medicinal plant Panax notoginseng (BurK.) F.H. Chen. Trichalasins E (1) contains a unique hydroperoxyl group, which is the first report in all known analogues, whereas trichalasin H (7) possesses the rare 6/5/6/6/5 pentacyclic skeleton with 12-oxatricyclo [6.3.1.0^2,7] moiety as that of aspergillin PZ (8). The relative configurations of the new compounds were characterized by analysis of coupling constants and ROESY correlations, and the absolute configurations of trichalasins E (1), H (7) and aspergillin PZ (8) were determined by modified Mosher’s reaction. In addition, compounds 1–5, 7 and 8 were tested cytotoxic activities against several cancer cell lines.     

Two new isopimarane diterpenes from the feces of Trogopterus xanthipes

Chemical investigation of Trogopterus Feces has led to the isolation of two new isopimarane diterpenes, wulingzhic acid A (1) and wulingzhic acid B (2). Their structures were elucidated by chemical and extensive spectral analysis. Compounds 1 and 2 exhibited weak activity of antithrombin and moderate activity of antiplatelet aggregation in vitro.     

Norditerpenoids from Salvia castanea Diels f. pubescens

Three new norditerpenoids, castanol A-C (1-3), along with eighteen known diterpenoids, were isolated from Salvia castanea Diels f. pubescens. Their structures were elucidated by extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities against five human cancer cell lines. The known compounds neo-tanshinlactone (12) and methyltanshinoate (17) exhibited significant cytotoxic activities against some cells.     

Unusual ingenoids from Euphorbia erythradenia Bioss. with pro-apoptotic effects

Dichloromethane-acetone extract of Euphorbia erythradenia Bioss., a spurge endemic to the Iran, afforded four novel tetrahydroingenol diterpenes, one new myrsinane type diterpene, and two known triterpenes. Tetrahydroingenoids are novel compounds not only for the double bond reduction but also for their unique hydroxylation pattern at C-11 and C-13. The structures of these compounds were elucidated by spectroscopic methods, and especially 2D NMR measurements. The biological effects of the compounds were done by the MTT and Annexin V-FITC & PI staining assays on different cancer cell lines. The results obtained on EJ-138, CAOV-4, and OVCAR-3 cell lines suggested that tetrahydroingenanes inhibit cell proliferation through apoptosis in cancer cell lines. In conclusion, the new pattern of hydrogenation and hydroxylation of these compounds compared to other ingenoids, along with their apoptosis inducing properties on cancer cells, makes them of great interest for more investigation.     

Two new α-pinene derivatives from Angelica sinensis and their anticoagulative activities

Two new α-pinene derivatives (1-2) were isolated from the aerial parts of Angelica sinensis. Their structures were determined by spectroscopic and chemical methods to be 6β,9-dihydroxy-(+)-α-pinene (1) and 9-hydroxy-(+)-α-pinene-6β-O-D-glucoside (2). In the anticoagulative assay, compounds 1 and 2 exhibited weak antithrombin activity and strong antiplatelet aggregation activity in vitro.