α-Glucosidase inhibitory triterpenoids from the stem barks of Uncaria laevigata

A phytochemical study on the ethanolic extract of the stem barks of Uncaria laevigata leads to the isolation and characterization of 18 triterpenoid compounds. Ten of these are new, including one novel heptanortriterpenoid (1), four ursane triterpenes (2–4, 10), and five oleanane triterpenes (5–9). Their structures were established by spectroscopic methods, especially by 2D-NMR and MS analyses. All these isolates were evaluated for their inhibitory effects on α-glucosidase: ursolic acid and 3 showed potent activities with IC₅₀ values of 16 ± 2.2 and 49 ± 3.7 μM, respectively.     

Modulation of COX,LOX and NFκB activities by Xanthium spinosum L. root extract and ziniolide

Xanthium spinosum L. (Asteraceae) is a medicinal weed distributed worldwide. Many of its diverse ethnopharmacological uses – namely diarrhoea, inflammation, liver disorders, snake bite and fever – are linked – at least in part – to an uncontrolled release of arachidonic acid metabolites. The crude extract of X. spinosum roots from Jordanian origin dose-dependently inhibited the 5-LOX (IC₅₀ ≅ 10 μg/mL), COX-1(IC₅₀ ≅ 50 μg/mL), and 12-LOX (IC₅₀ ≅ 170 μg/mL) enzymatic pathways in intact pro-inflammatory cells. A direct activity at the level of PLA₂ is not probable, but the extract induced the synthesis of the anti-inflammatory eicosanoid 15(S)-HETE, which may in turn inhibit this enzyme. 5-LOX bioguided fractionation of the crude extract led to the isolation of ziniolide, a known 12,8-guaianolide sesquiterpene lactone, from the hydro-alcoholic fraction of the n-hexane extract (IC₅₀ = 69 μM). Both the plant extract and ziniolide are in vitro inhibitors of the phorbol-induced NFκB activation, a key regulator of the arachidonic pathway.     

Genotypic variation in wood density and growth traits of poplar hybrids at four clonal trials

Wood density is considered as one of the most important wood properties which affects the properties and value of both fibrous and solid wood products. The present study was intended for evaluating the possibilities of improving wood quality and growth of poplar hybrids. Wood density components of individual growth rings (minimum and maximum wood density, average ring density) and growth traits (tree height, dbh, stem volume) were measured in four 10- and 12-year-old clonal trials of four poplar hybrids, Populus deltoides × P. nigra, P. trichocarpa × P. deltoides, P. maximowiczii × P. balsamifera, and P. balsamifera × P. nigra, as well as P. deltoides. Wood density components of individual growth rings were obtained from microdensitometeric profiles measured with a direct reading X-ray densitometer. Site had a moderately significant effect on wood density and a highly significant effect on tree growth. The hybrid effect was highly significant (P < 0.001) for most traits. Minimum, maximum and weighted wood densities were found to be under strong genetic control, with clonal repeatabilities varying between 0.45 and 0.81. The coefficient of genotypic variation (CV_G) for wood density at individual sites ranged from 4.0 to 6.8%, whereas CV_G for dry fiber weight (mass) reached 32.8% with repeatabilities of up to 0.67. A small but significant (P = 0.028) hybrid × environment interaction was found for dry fiber weight. The highest ecological sensitivity was found for P. deltoides × P. nigra, with ecovalence reaching 32.3%. Clonal × environment interaction was significant for weighted, average, and minimum wood density. Significant negative genotypic correlations between stem volume and wood density ranged from −0.39 to −0.74. One possible strategy in tree breeding would be to maximize wood fiber production through selection for dry fiber weight.     

Phytic acid enhances the oral absorption of isorhamnetin,quercetin, and kaempferol in total flavones of Hippophae rhamnoides L.

AimTotal flavones of Hippophae rhamnoides L. (TFH) have a clinical use in the treatment of cardiac disease. The pharmacological effects of TFH are attributed to its major flavonoid components, isorhamnetin, kaempferol, and quercetin. However, poor oral bioavailability of these flavonoids limits the clinical applications of TFH. This study explores phytic acid (IP₆) enhancement of the oral absorption in rats of isorhamnetin, kaempferol, and quercetin in TFH.MethodsIn vitro Caco-2 cell experiments and in vivo pharmacokinetic studies were performed to investigate the effects of IP₆. The aqueous solubility and lipophilicity of isorhamnetin, quercetin, and kaempferol were determined with and without IP₆, and mucosal epithelial damage resulting from IP₆ addition was evaluated by MTT assays and morphology observations.ResultsThe P_app of isorhamnetin, kaempferol, and quercetin was improved 2.03-, 1.69-, and 2.11-fold in the presence of 333 μg/mL of IP₆, respectively. Water solubility was increased 22.75-, 15.15-, and 12.86-fold for isorhamnetin, kaempferol, and quercetin, respectively, in the presence of 20 mg/mL IP₆. The lipophilicity of the three flavonoids was slightly decreased, but their hydrophilicity was increased after the addition of IP₆ in the water phase as the logP values of isorhamnetin, kaempferol, and quercetin decreased from 2.38 ± 0.12 to 1.64 ± 0.02, from 2.57 ± 0.20 to 2.01 ± 0.04, and from 2.39 ± 0.12 to 1.15 ± 0.01, respectively. The absorption enhancement ratios were 3.21 for isorhamnetin, 2.98 for kaempferol, and 1.64 for quercetin with co-administration of IP₆ (200 mg/kg) in rats. In addition, IP₆ (200 mg/kg, oral) caused neither significant irritation to the rat intestines nor cytotoxicity (400 μg/mL) in Caco-2 cells.ConclusionsThe oral bioavailability of isorhamnetin, kaempferol, and quercetin in TFH was enhanced by the co-administration of IP₆. The main mechanisms are related to their enhanced aqueous solubility and permeability in the presence of IP₆. In summary, IP₆ is a potential absorption enhancer for pharmaceutical formulations that is both effective and safe.     

Desmodeleganine,a new alkaloid from the leaves of Desmodium elegans as a potential monoamine oxidase inhibitor

Desmodeleganine (1), a new potential monoamine oxidase inhibitor, along with three known alkaloids, bufotenin (2), hydroxy-N, N-dimethyltryptamine N¹²-oxide (3), 2-(5-methoxy-1H-indol-3-yl)-N, and N-dimethylethylamine (4) were isolated from the leaves of Desmodium elegans. Their structures were elucidated by IR, MS, 1D and 2D NMR spectra. 1 showed strong monoamine oxidase inhibitory activity with IC₅₀ value of 13.92 ± 1.5 μM, when the IC₅₀ value of iproniazid as a standard was 6.5 ± 0.5 μM. The molecular modeling was also performed to explore the binding mode of compounds 1, 2 at the active site of MAO-A and MAO-B.     

Estrogenic and anti-estrogenic activities of hispolon from Phellinus lonicerinus (Bond.) Bond. et sing

Hispolon was the main antitumor active ingredient in Phellinus sensu lato species. In order to confirm the dual regulating estrogenic ingredient and obtain more effective natural estrogen replacement drugs, hispolon was separated from Phellinus lonicerinus (Bond.) Bond. et sing. Hispolon exhibited significant anti-proliferative effect against estrogen-sensitive ER (+) MCF-7 cells in the absence of estrogen, and exhibits antagonistic effects on 17β-estradiol (E₂)-induced MCF-7 cell proliferation when E₂ and the different concentrations of hispolon were treated simultaneously. Hispolon also inhibited the proliferation of estrogen-negative ER (−) MDA-MB-231 cells at the concentration of 5.00 × 10^− 5 M. The yeast two-hybrid experiments showed that hispolon had strong and non-selective effects on the estrogen receptor (ER) α and ERβ at a concentration of 1.00 × 10^− 6 M. The ERβ-binding ability of hispolon was larger than ERα in the concentration range of 1.00 × 10^− 9 M and 1.00 × 10^− 7 M. Hispolon could increase the body weight coefficient, serum E₂ and progesterone contents in immature female mice at dose of 9.10 × 10^− 6 mol/kg, and increase coefficient of thymus and spleen in mice. The Gscores of hispolon-ERα and hispolon-ERβ docked complexes were − 7.93 kcal/mol and − 7.79 kcal/mol in docking simulations. Hispolon presented dual regulating estrogenic activities, which showed estrogenic agonist activity at low concentration or lack of endogenous estrogen, and the estrogenic antagonistic effect was stimulated at high concentrations or too much endogenous estrogen. Hispolon could be used for treating the estrogen deficiency-related disease with the benefit of non-toxic to normal cells, good antitumor effects and estrogenic activity.     

A potent acetylcholinesterase inhibitor from Pancratium illyricum L.

Plants belonging to the Amaryllidaceae contain an exclusive group of alkaloids, known as sources of important biological activities. In the present work, Pancratium illyricum L., a species belonging to this family and endemic of Sardinia (Italy), was investigated for its alkaloid content. Fresh bulbs and leaves were processed separately. Standard extraction and purification procedures were applied to obtain fractions and compounds for GC–MS and NMR analysis. In addition to eight already known alkaloids (1–8), 11α-hydroxy-O-methylleucotamine (9) was isolated for the first time and its structure completely determined by one and two-dimensional ¹H and ¹³C NMR spectroscopy. This new galanthamine-type compound exhibited a pronounced in vitro acetylcholinesterase (AChE) inhibitory activity (IC₅₀ = 3.5 ± 1.1 μM) in comparison to the reference standard galanthamine hydrobromide (IC₅₀ = 1.5 ± 0.2 μM).     

Phytochemical investigation of sesquiterpenes from the fruits of Schisandra chinensis and their cytotoxic activity

Phytochemical investigation of ethanolic extract from the fruits of Schisandra chinensis led to the isolation of four new sesquiterpenes (1–4); their structures were determined by a combination of NMR (1D and 2D) and MS spectroscopic techniques. In addition, all these isolates were screened for their cytotoxic activities against MCF-7, Caco-2, Hela, Lncap, Hep G2 and MDA-MB231 cancer cell lines. Results indicated that compounds 2 and 3 displayed potent cytotoxic activity against Caco2 cell lines with IC₅₀ values of 17.10 μg/mM and 16.46 μg/mM, respectively.     

Utilization and traditional strategies of in situ conservation of iroko (Milicia excelsa Welw. C.C. Berg) in Benin

Socio-cultural surveys were carried out on the basis of a questionnaire administered on 346 respondents in order to investigate cultural and ethnobotanic uses of Milicia excelsa in Benin.M. excelsa contributes to cure 45 human diseases. The different parts of the tree used are leaves (30.3%), bark (25.8%), root (23.6%), latex (10.1%), flaking bark (6.7%), wood, calcium concentrated in old trees, and gum (1.1% each). Fruits or seeds are rarely used. Six different forms of utilization were recorded: soaking (46.3%), bark or leaves decoction (32.8%), herb tea (11.9%), powder (6.0%), leaves or bark grounded and rolled up into ball (1.5%), component of offering to fetish (1.5%). Iroko wood is also used in carpentry and joinery for construction purposes; furniture as well as for building boats/canoes.Iroko tree is used as the conservatory of cultural values and incarnates many divinities, which differ significantly from one province to another (χ² = 1830.27; d.f. = 25; P < 0.01%). There is a significant difference between the provinces in respect of the recognition of the species (χ² = 268.71; d.f. = 17; P ≤ 0.01%) and the population awareness about iroko as a sacred tree also varied from one province to another (χ² = 308.66; d.f. = 27; P ≤ 0.01%).Veneration of the tree is the main approach of its conservation by local people. M. excelsa is conserved on farm, in sacred groves, in public places and in cemeteries. The different sacred objects used to symbolize the divinities incarnated by iroko are: pottery (36.36%), iron (11.11%), calabash (4.04%), candle (2.02%), piece of cloth (18.18%), sacrifice (13.13%), piece of money (3.0%), stone (2.05%), glassware (broken bottle, 2.02%), and convent (8.08%). There is a highly significant difference between provinces as far as the sacred objects are concerned (χ² = 183.037; d.f. = 19 and P < 0.001%). The conservation purposes also vary significantly from one region to other (χ² = 894.47; d.f. = 31; P < 0.01%).     

Chemical constituents from Aphanamixis grandifolia

Four new terpenoids, nemoralisins D–G (1–4), were isolated from the leaves and stems of Aphanamixis grandifolia, along with two known diterpenoids, nemoralisin C and nemoralisin. Among them, compound 1 is the first example of norsesquiterpenoid with δ-lactone moiety, and nemoralisins E–G (2–4), are a class of acyclic diterpenoids, which are structurally related nemoralisin C and nemoralisin. These structures were established on the basis of spectroscopic methods and the absolute configuration of 1 was determined by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Nemoralisins D–G (1–4) were tested for their cytotoxicities on HL-60, SMMC-7721, A-549, MCF-7, and SW480 human tumor cell lines (IC₅₀ > 40 μM), as well as the antimicrobial activities on Staphylococcus aureus, Pseudomonas aeruginosa, MRSA92^# and MRSA98^# (MIC > 50 μg/mL).     

Different pharmacokinetics of the two structurally similar dammarane sapogenins,protopanaxatriol and protopanaxadiol,in rats

Dammarane Sapogenins (DS), with main ingredients of protopanaxatriol (PPT, 33%) and protopanaxadiol (PPD, 16%), is an alkaline hydrolyzed product of ginsenosides and had significant activities in improving learning and memory and decreasing chemotherapy-induced myelosuppression. In the present study, the pharmacokinetics and oral bioavailabilities of PPT and PPD were investigated when a single dose of DS was administrated orally (75 mg/kg) and intravenously (i.v., 30 mg/kg) to rats. Their in vitro stabilities in the GI tract were also investigated. PPT and PPD concentrations were measured by LC–MS. The results showed that PPT was eliminated rapidly from the body with an average t_{1/2, λz} value of 0.80 h and CL of 4.27 l/h/kg after i.v. administration, while PPD was eliminated relatively slowly with a t_{1/2, λz} of 6.25 h and CL of 0.98 l/h/kg. After oral administration, both PPD and PPT could be absorbed into the body, but their systemic exposures were quite different. PPT was absorbed into the body quickly, with a T_max of 0.58 h and a C_max of 0.13 μg/ml, while PPD was absorbed relatively slowly with a T_max of 1.82 h and a C_max of 1.04 μg/ml. The absolute bioavailabilities of PPT and PPD were estimated as 3.69% and 48.12%, respectively. The stability test found that PPT was instable in the stomach with 40% degradation after 4 h incubation at 37 °C, both in pH 1.2 buffer and in the stomach content solution. The instability in the stomach might be one of the reasons for PPT's poor bioavailability.     

Japonicasins A and B,two new isoprenylated flavanones from Sophora japonica

Two new flavanones with a C₁₅ isoprenoid group, japonicasins A and B (1 and 2), were isolated from the leaves of Sophora japonica. This is the first report on the presence of the (2E,7E)-6-isopropyl-3,9-dimethyldeca-2,7,9-trien-1-yl group (C₁₅ isoprenoid group) in isoprenylated flavonoids. Their structures were determined by spectroscopic methods, including UV, IR, 1D and 2D NMR, HRESIMS, and CD experiments. In addition, the antioxidant activities of compounds 1 and 2 were determined through DPPH radical scavenging assays. They exhibited potential antioxidant activities, with IC₅₀ values of 35.1 ± 0.8 μM and 88.7 ± 1.1 μM for compounds 1 and 2, respectively.     

Phenylethanoid glycosides from the stems of Callicarpa peii (hemostatic drug)

Two new trisaccharide intermediates of phenylethanoid glycosides, peiioside A₁/A₂ (1a/1b) and peiioside B (2), were isolated from the n-BuOH fraction of MeOH extract of the stems of Callicarpa peii H.T. Chang, together with five biogenetic relevant known compounds 3–7. The structures of compounds 1 and 2 were elucidated by extensive spectroscopic methods (especially 2D-NMR techniques) and acid-catalyzed hydrolysis as O-α-l-rhamnopyranosyl-(1″ → 3′)-O-[β-d-apiofuranosyl-(1‴ → 6′)] -4′-O-[(E)-caffeoyl]-d-glucopyranoside] (1a/1b), 3,4-dihydroxy-β-phenylethoxy-O-[β-d-apiofuranosyl-(1‴ → 6′)-α-l-rhamnopyranosyl-(1″ → 3′)-O-β-d-glucopyranoside] (2), respectively. On the basis of the isolated compounds, a presumable biogenetic pathway of the biologically interesting phenylethanoid glycosides about forsythoside B (3) and acteoside (4) isolated from this species was proposed. Isolation of five related intermediates (1–2, 5–7) provided further support for the biogenetic path. This is the first report about phytochemical research on C. peii and the biogenetic hypothesis of forsythoside B and acteoside.     

In vitro permeability analysis,pharmacokinetic and brain distribution study in mice of imperatorin,isoimperatorin and cnidilin in Radix Angelicae Dahuricae

Coumarins are important constituents of Radix Angelicae Dahuricae, a well-known traditional Chinese medicine possess several known bioactivities with potentials in the treatment of central nervous system diseases. By using an HPLC–MS/MS method, we analyzed the in vivo plasma and brain pharmacokinetics of three ingredients of coumarins, including imperatorin, isoimperatorin and cnidilin in mice after oral administration of Dahuricae extract at doses of 800 mg/kg. The biosamples were prepared using acetonitrile precipitation and the separation was achieved on an XDB-C18 column by gradient elution. The BBB permeability and P-gp-mediated efflux were further examined in Madin Canine kidney cells transfected with full length cDNA for human multidrug resistance gene1 (MDCKII-MDR1). Our results demonstrate that the method has excellent and satisfactory selectivity, sensitivity, linearity, precision, and accuracy for simultaneous determination of imperatorin, isoimperatorin and cnidilin. The pharmacokinetics parameters were determined by using noncompartmental analyses, including the AUC_(0 − t) in plasma (1695.22, 1326.45 and 636.98 mg*h/L), the AUC_(0 − t) in brain (1812.35, 2125.17 and 1145.83 ng*h/g) as well as the T_1/2 in plasma (0.66, 0.82, 0.97 h) and brain (0.96, 1.1, 0.99 h) for imperatorin, isoimperatorin and cnidilin, respectively, suggesting that the three coumarins could easily pass through the BBB in vivo. In the in vitro model we observed high permeability of imperatorin and isoimperatorin with the P-gp-mediated efflux ratios of 0.53 and 0.06, as well as medium permeability of cnidilin with 0.82. All data suggest that these three coumarins have high BBB permeability and have pharmacokinetic potentials for the treatment of central nervous system diseases.     

Inactivation of jack bean urease by scutellarin: Elucidation of inhibitory efficacy,kinetics and mechanism

In the present study, the inactivation effect of scutellarin (SL) on jack bean urease was investigated to elucidate the inhibitory potency, kinetics and mechanism of inhibition. It was revealed that SL acted as a concentration- and time-dependent inactivator of urease characteristic of slow-binding inhibition with an IC₅₀ of 1.35 ± 0.15 mM. The rapid formation of the initial SL–urease complex with an inhibition constant of K_i = 5.37 × 10^− 2 mM was followed by a slow isomerization into the final complex with the overall inhibition constant of K_i* = 3.49 × 10^− 3 mM. High effectiveness of thiol protectors, such as L-cysteine (L-cys), 2-mercaptoethanol (2-ME) and dithiothreitol (DTT) significantly slowed down the rate of inactivation, indicating the strategic role of the active site sulfhydryl group in the blocking process. While the insignificant protection by boric acid and fluoride from the inactivation further confirmed that the active site cysteine should be obligatory for urease inhibition, which was also rationalized by the molecular docking study. The inhibition of SL on urease proved to be reversible since SL-blocked urease could be reactivated by DTT application and multidilution. The results obtained indicated that urease inactivation resulted from the reaction between SL and the sulfhydryl group.     

Demography and life history of Geonoma orbignyana: An understory palm used as foliage in Colombia

Geonoma orbignyana is a common understory palm, whose leaves are used as foliage in Colombia. This palm has been used for more than 30 years; but there is no information about its life history or conservation status. Our objective was to characterize the life history of this palm and population dynamics of a natural population as a first step to assess the effect of leaf harvesting. More than 1600 palms were monitored from June 1999 to March 2000; we measured growth, mortality, and reproductive success. Population dynamics were evaluated using a Lefkovitch matrix model, and elasticity analysis. Results indicate that G. orbignyana grows at a rate of 1.98 ± 0.047 leaves/year, the palm has a long lifespan, and growth and reproduction are related to light conditions in the forest. The density of this palm is high (108–311 palms/100 m²), which is explained in part by its capacity to continue growing after damage, and to respond to the frequent gap formation in the forest. The population is growing (λ = 1.074, CI = [1.046–1.099]). Survival transitions account for 77% of population growth, a value that is higher compared to other understory plants. Because of the high density, the recovery capacity of these palms, and the correlations found between individual and population performances with forest dynamics, we hypothesize that G. orbignyana behaves as an opportunistic species taking advantage of forest gaps. This palm is a promising non-timber forest product (NTFP) with a high profile for further exploitation, although we recommend that harvesting regimens should consider time of recovery and forest dynamics. Without these considerations mortality could increase in all classes, which will compromise population persistence. Further studies should accurately estimate the recovery time after defoliation as well as to characterize forest dynamics identifying its most important features for population growth.     

Structural characterization and antioxidant activity of a low-molecular polysaccharide from Dendrobium huoshanense

The present study aimed at investigating the structural features and antioxidant activities of a polysaccharide fraction (DHP1A) obtained from Dendrobium huoshanense, a precious herb medicine in China. DHP1A mainly consisted of mannose (Man), glucose (Glc) and a trace of galactose (Gal), with a molecular weight of 6700 Da. Its backbone contained (1 → 4)-linked α-D-Glcp, (1 → 6)-linked α-D-Glcp and (1 → 4)-linked β-D-Manp, with a branch of terminal β-D-Galp. The in vitro antioxidant evaluation revealed that DHP1A had a remarkable inhibition effect on the FeCl₂-induced lipid peroxidation. Furthermore, DHP1A pretreatment decreased the production of malondialdehyde (MDA), and restored the activities of superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPx), as well as the level of glutathione (GSH) in the livers of CCl₄-treated mice. These results suggested that DHP1A was a potential antioxidant component in D. huoshanense.     

Pharmacokinetic study of eight coumarins of Radix Angelicae Dahuricae in rats by gas chromatography–mass spectrometry

A sensitive, specific gas chromatography–mass spectrometry (GC–MS) method was established for the quantitative determination of eight coumarins of Radix Angelicae Dahuricae including coumarin, isopsoralen, psoralen, xanthotoxin, bergapten, osthole, imperatorin and oxypeucedanin in rat plasma. Nitrendipine was used as the internal standard (IS). The plasma samples were extracted by acetonitrile. GC separation was accomplished on a DB-5MS column with temperature programmed from 160 °C (17 min) to 190 °C (10 min) at the rate of 20 °C/min, then to 240 °C (5 min) at 20 °C/min, and finally to 280 °C (14 min) at 20 °C/min. The detection was performed on a quadrupole mass spectrometer detector operated by full-scan mode (m/z 50–500). The lower limit of quantitation was 5–10 ng/mL for eight coumarins, and the linear range was 5–1000 ng/mL for the coumarins (R² > 0.9990). All the validation data were within the required limits. After oral administration, the plasma concentration–time curves showed that the time for maximum concentration (T_max) was 1.29 for coumarin, 1.83 for isopsoralen, 1.93 for psoralen, 1.30 for xanthotoxin, 2.04 for bergapten, 0.64 for osthole, 1.41 for imperatorin and 0.51 h for oxypeucedanin. The plasma concentration of the eight coumarins was low, with a mean maximum plasma concentration (C_max) < 6.41 μg/mL. Pharmacokinetic data analysis showed that the eight coumarins had different pharmacokinetic characteristics after oral administration. The method was successfully applied to pharmacokinetic studies of eight coumarins after oral administration in rats.     

Chemical constituents of Swertia yunnanensis and their anti-hepatitis B virus activity

Four new triterpenoids, sweriyunnangenin A (1), sweriyunnanosides A (2), B (3) and C (4), along with nineteen known compounds (5–23) were isolated from Swertia yunnanensis. Based on extensive spectroscopic analyses (1D- and 2D-NMR, HRESIMS, UV, IR, [α]_D), the structures of sweriyunnangenin A (1), sweriyunnanosides A (2), B (3) and C (4) were elucidated as taraxer-14-ene-3α,6β-diol, oleanolic acid 28-O-β-d-glucopyranosyl-(1 → 2)-O-β-d-glucopyranoside, 2α,3β-di-hydroxyolean-12-en-28-oic acid 28-O-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl (1 → 6)-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranoside and hederagenin 28-O-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl(1 → 6)-β-d-glucopyranosyl(1 → 2)-β-d-glucopyranoside, respectively. Twenty-two compounds were evaluated for their anti-HBV activities on the HepG 2.2.15 cell line in vitro, of which nine compounds showed potent anti-HBV activities. Compounds 1, 5–6, 14–16 and 19 showed activities against the secretion of HBsAg (IC₅₀ values from 0.10 to 1.76 mM) and HBeAg (IC₅₀ values from 0.04 to 1.41 mM), and compounds 11 and 13–16 exhibited significant inhibition on HBV DNA replication (IC₅₀ values from 0.01 to 0.09 mM).     

New cytotoxic triterpenoid saponins from the whole plant of Clematis lasiandra Maxim

Four new oleanane type triterpenoid saponins (1–4) and three known saponins (5–7) were isolated from the whole plant of Clematis lasiandra Maxim. The structures of the four new compounds were elucidated as 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl hederagenin (1), 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl oleanolic acid 28-O-β-d-glucopyranosyl ester (2), 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyl hederagenin (3) and 3-O-β-d-ribopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-α-l-arabinopyranosyl hederagenin (4) on the basis of extensive spectroscopic analysis and chemical evidence. Compounds 1–7 were evaluated for their cytotoxicity against human tumor cell lines HL-60, Hep-G2 and SGC-7901, and all of the evaluated saponins showed significant cytotoxicity to those three tumor cell lines with IC₅₀ in the range from 1.40 to 19.50 μmol/L except for compounds 2 and 6.