Cycloartane saponins from Astragalus peregrinus as modulators of lymphocyte proliferation.

From Astragalus peregrinus, four cycloartane-type saponins have been isolated and their structures elucidated by spectral means as 20(R),24(S)-epoxy-9 beta,19-cyclolanostane-3 beta,6 alpha,16 beta,25-tetrol 3-O-beta-D-glucopyranoside (1), 20(R),24(S)-epoxy-9 beta,19-cyclolanostane-3 beta,6 alpha,16 beta,25-tetrol 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranoside (2), 20(R),24(S)-epoxy-9 beta,19-cyclolanostane-3 beta,6 alpha,16 beta,25-tetrol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (3) and 20(R),25-epoxy-9 beta,19-cyclolanostane-3 beta,6 alpha,16 beta,24(S)-tetrol (24-O-acetyl)- 3-O-alpha-L-rhamnopyranosyl-(1-->2)-(6'-O-acetyl)-beta-D-glucopyranoside (4). Compounds 2 and 3 showed to stimulate the proliferation of mouse splenocytes and were not significantly cytotoxic.     

New antifungal constituents from Terminalia alata

The roots of Terminalia alata yielded three new glycosides: 3,3'-di-O-methylellagic acid 4-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranoside (1), 5,7,2'-tri-O-methylflavanone 4'-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranoside (2), and 2alpha,3beta, 19beta,23-tetrahydroxyolean-12-en-28-oic acid 3-O-beta-D-galactopyranosyl-(1-->3)-beta-D-glucopyranoside-28-O-beta-D-glucopyranoside (3). Compounds 2 and 3 displayed antifungal activity.     

A new lupene triterpenetriol and anticholinesterase activity of Salvia sclareoides

A new lupene triterpenetriol was isolated from the acetone extract of the aerial parts of Salvia sclareoides and characterised as (1beta,3beta)-lup-20(29)-ene-1,3,30-triol (1). In addition, nepetidin (2), nepeticin (3), lupendiol (4), (1beta,11alpha)-dihydroxy-lup-20(29)-en-3-one (5), ursolic acid (6), sumaresinolic acid (7) and hederagenin (8), were identified in this Salvia sp. To the best of our knowledge, the compounds 2 and 7 are new constituents in Salvia spp. The acetone, ethanol, butanol and water extracts of the plant were screened for the in vitro inhibitory activity of acetylcholinesterase (AChE) and butyrilcholinesterase (BChE), enzymes which play a role in the Alzheimer disease. All extracts inhibited acetylcholinesterase activity at 10 microg/ml, a remarkable activity since the standard drug rivastigmine does not inhibit acetylcholinesterase at the same concentration. Regarding the butyrilcholinesterase, the acetone extract at 1000 microg/ml was able to inhibit completely the enzyme activity and the butanol and ethanol extracts, at this concentration, produced a potent inhibition of BchE.     

New triterpenoids from the stems and leaves of Panax ginseng

Three new dammarane-type triterpene saponins ginsenosides Rh(18) (1), Rh(19) (3) and Rh(20) (4), along with two new triterpene sapogenins 12β,23(R)-epoxydammara-24-ene-3β,6α,20(S)-triol (2) and dammara-(20E)22,25-diene-3β,6α,12β,24S-tetrol (5) were isolated from the stems and leaves of Panax ginseng C. A. Mey. Their structures were elucidated on the basis of spectral evidence and comparisons with literature data.     

A novel furostanol saponin from Tribulus terrestris of Bulgarian origin

The phytochemical investigation of the aerial parts of Tribulus terrestris of Bulgarian origin has resulted in the isolation of the novel furostanol saponin 1, named tribol, together with the known spirostanol saponins 2 and 3 and sitosterol glucoside. The structure of tribol was determined as (25R)-furost-5(6)-ene-3beta,16,26-triol-3-O-alpha-rhamnopyranosyl-(1-->2)-[alpha-rhamnopyranosyl-(1-->4)]-beta-glucopyranoside (1) by spectral analysis, including extensive 1D and 2D-NMR experiments.     

Two new steroidal saponins from Selaginella uncinata (Desv.) Spring and their protective effect against anoxia

Four steroidal saponins were isolated from the anti-anoxic fraction of the 60% EtOH extract of Selaginella uncinata, including two new compounds, (3β, 7β, 12β, 25R)-spirost-5-ene-3, 7, 12-triol-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 4)]-O-β-d-glucopyranoside (1), (2α, 3β, 12β, 25R)-spirost-5-ene-2, 3, 12-triol-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 4)]-O-β-d-glucopyranoside (2) and two known compounds, (3β, 12β, 25R)-spirost-5-ene-3,12-diol-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-rhamnopyranosyl-(1 → 4)]-O-β-d-glucopyranoside, (3), (1α, 3β, 25R)-spirost-5-ene-2-diol-3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[α-L-rhamnopyranosyl(1 → 4)]-O-β-d-glucopyranoside (4). The four compounds showed potent protective effect against anoxia in the anoxic PC12 cells assay, among which compounds 1 and 2 were the most active. To our knowledge, this is the first study to report the steroidal saponins in the plant S. uncinata and demonstrate their protective effect against anoxia in PC12 cell assay.     

A new kaurane diterpene dimer from Parinari campestris

A new kaurane diterpene dimer, 15-oxozoapatlin-13alpha-yl-10'alpha,16'alpha-dihydroxy-9'alpha-methyl-20'-nor-kauran-19'-oic acid gamma-lactone-17'-oate (1), together with the known 13-hydroxy-15-oxozoapatlin (2), 10alpha,13alpha,16alpha,17-tetrahydroxy-9alpha-methyl-15-oxo-20-nor-kauran-19-oic acid gamma-lactone (3), 2alpha,10alpha,13alpha,16alpha,17-pentahydroxy-9alpha-methyl-15-oxo-20-nor-kauran-19-oic acid (19,10)-lactone (4), 3alpha,10alpha,13alpha,16alpha,17-pentahydroxy-9alpha-methyl-15-oxo-20-nor-kauran-19-oic acid gamma-lactone (5), and 1beta,16alpha,17-trihydroxy-ent-kaurane (6) were isolated from the leaves of Parinari campestris and identified on the basis of detailed spectral analysis, including 2D NMR spectrometry and ESI-MS.     

A new ent-kaurane diterpenoid from Rabdosia pseudo-irrorata.

A new kaurenoid, ent-3 beta,7 alpha,14 beta-trihydroxykaur-16-ene-12,15-dione (1), named pseurata G, was isolated from the ethanol extract of the whole plant of Rabdosia pseudo-irrorata.     

A new cardenolide from the roots of Streptocaulon tomentosum

A new cardenolide, (17 alpha)-H-periplogenin-3-O-beta-D-glucopyranosyl-(1-4)-2-O-acetyl-3-O-methyl-beta-fucopyranoside (1), was isolated from the roots of Streptocaulon tomentosum.     

Study on the structure–function relationship of 20(S)-panaxadiol and its epimeric derivatives in myocardial injury induced by isoproterenol

This study was aimed to investigate structure–function relationship of 20(S)-panaxadiol (PD) and its epimeric derivatives ((20S, 24S)-epoxy-dammarane-3β, 12β, 25-triol, PDD1 and (20S, 24R)-epoxy-dammarane-3β, 12β, 25-triol, PDD2) in myocardial ischemia injury in rats. It was shown that PD and PDD2 resulted in a reduction in creatine kinase activity. PD and PDD2 inhibited the elevation of malondialdehyde content, the reduction of superoxide dismutase and glutathione peroxidase activities. The pathohistological changes were ameliorated by PD and PDD2. The configuration of C-24 of funan ring was linked to the pharmacological action of 20(S)-panaxadiol and its epimeric derivatives.     

Cerebroside and ceramide from the pollen of Brassica napus L.

The new cerebroside 1-O-(β-d-glucopyranosyl)-(2 S, 3 S, 4R, 8E)-2-[(2′R)-2′-hydroxytetracosenoilamino]-8-octadecene-1,3,4-triol (1) and ceramide (2 S, 3 S, 4R, 8E)-2-[(2′R)-2′-hydroxytetracosenoilamino]-8-octadecene-1,3,4-triol (2) were isolated from the ethyl acetate extract of the pollen of Brassica napus L. The structures of 1 and 2 were elucidated on the basis of chemical and spectroscopic method. Two new compounds were evaluated for activity in vitro assays for the cytotoxic activities against human tongue squamous carcinoma cell line (Tca8113).     

ent-Isopimarane diterpenoids of the leaves from Rabdosia forrestii

Two new diterpenes, forrestin H, ent-isopimaran-8 beta, 15R, 16-triol (1), forrestin I, ent-isopimaran-16-acetoxy-8 beta, 15R-diol (2) and the acetonide derivative of forrestin H were isolated from the leaves of Rabdosia forrestii. The structures were established on the basis of NMR spectroscopic analysis and of the modified Mosher's (1H) method.     

A new triterpenoid from Azadirachta indica

A new triterpenoid, 1 alpha,7 alpha-diacetoxyapotirucall-14-en e-3 alpha, 21,22,24,25-pentaol (1), and the two known compounds odoratone (2) and 2 beta,3 beta,4 beta-trihydroxypregnan-16-o ne (3) were isolated from a methanolic extract of the seed kernels of Azadirachta indica. Their structures were elucidated on the basis of spectral methods.     

Antifungal activity of Agapanthus africanus extractives

The ethanolic extract of the rhizomes of Agapanthus africanus showed antifungal activity. In bioassay guided fractionation, n-butanol fraction exhibited significant activity against human pathogens. A saponin, (25R)-spirost-7-en-2alpha,3beta,5alpha-triol-3-O-[alpha-L-rhamnopyranosyl(1-->2)-[beta-D-galactopyranosyl (1-->3)] beta-D-glucopyranoside (1), responsible for the antifungal activity and having MIC value of 15.6 microg/ml against Trychophyton mentagrophytes and Sporothrix schenekii, was isolated and identified as active constituent of the plant.     

A new cardenolide from the roots of Terminalia arjuna

A new cardenolide, 16,17-dihydroneridienone 3-O-beta-D-glucopyranosyl-(1-->6)-O-beta-D-galactopyranoside (1), was isolated from the roots of Terminalia arjuna.     

Two new diterpenes from Euphorbia kansuensis

Two new lathyrane diterpenes, 3beta,5alpha-dihydroxy-15beta-cinnamoyloxy-14-oxolathyra-6Z,12E -diene (1) and 3beta,5alpha,20-trihydroxy-15beta-cinnamoyloxy-14-oxolathyra-6Z,12E-diene (2), were isolated from the roots of Euphorbia kansuensis. Their structures were determined by spectroscopic methods.     

A new cerebroside from Polygala japonica

The isolation of a new cerebroside, 1-O-beta-d-glucopyranosyl-(2S,3S,4R,11E)-2-[(2'R)-2'-hydroxypalmitoylamino]-11-octadecene-1,3,4-triol (polygalacerebroside) (1), from the aerial part of Polygala japonica is reported.     

Steroidal saponins from Smilacina japonica

Three new steroidal saponins, japonicoside A (1), japonicoside B (2) and japonicoside C (3) were isolated from the dried rhizomes and roots of Smilacina japonica A. Gray. Their structures were elucidated as (25S)-5α-spirostan-9(11)-en-3β-ol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (1), (25S)-5α-spirostan-9(11)-en-3β,17α-diol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (2) and (25S)-5α-spirostan-9(11)-en-3β,17α,24α-triol 3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside (3) on the basis of chemical methods and detailed spectroscopic analysis, including 1D, 2D NMR and HR-ESI-MS. The cytotoxicity of isolated compounds was evaluated in vitro for cytotoxic properties against human hepatocellular carcinoma cells (SMMC-7221) and human colorectal adenocarcinoma cells (DLD-1), respectively.     

A non-ionic water-soluble seed gum from Ipomoea campanulata

A non-ionic water-soluble galactomannan, having galactose and mannose in 2:3 molar ratio was isolated from endosperm of the seeds of Ipomoea campanulata. The seed gum was found to have linear chain of beta (1-->4) linked mannopyranosyl units with D-galactose side chains attached through alpha (1-->6) linkage to the main chain. This structure is similar to many commercial gums like Guar, Carob and Locust bean gum. Various physical properties of the gum were studied in order to explore the possibility of commercial exploitation of the seed gum.     

A new steroidal saponin from the dried stems of Asparagus officinalis L

Yamogenin II (1), a new steroidal saponin with a unique aglycone moiety, and (25S)-spirostan-5-ene-3β-ol-3-O-α-l-rhamnopyranosyl-(1,2)-[α-l-rhamnopyranosyl-(1,4)]-β-d-glucopyranoside (2), were isolated from the dried stems of Asparagus officinalis L. The structure of 1 was assessed by spectroscopial analysis as (25S)-spirostan-5-ene-3β,21-diol-3-O-α-l-rhamnopyranosyl-(1,2)-[α-l-rhamnopyranosyl-(1,4)]-β-d-glucopyranoside.