Ellagic acid glycosides from Turpinia ternata

Bioassay-guided fractionation of the methanolic extract of Turpinia ternata stems, has led to the isolation of the new ellagic acid derivative 3,4'-di-O-methylellagic acid-4-O-alpha-L-arabinofuranoside (1), and the known compounds ellagic acid (2), 3-O-methyl ellagic acid (3), 3-O-methylellagic acid-3'-O-alpha-L-rhamnopyranoside (4), and 3,3'-di-O-methylellagic acid-4'-O-alpha-D-glucopyranoside (5). Their structures were elucidated by extensive spectroscopic methods. Compounds 1, 3, and 4 showed moderate antioxidant activity against DPPH free radical, whereas compound 1 was found to be moderately cytotoxic against Artemia salina larvae.     

New benzoyl glucosides and cytotoxic pterosin sesquiterpenes from Pteris ensiformis Burm

Three new compounds: 2R,3R-pterosin L 3-O-beta-D-glucopyranoside (1), beta-D-xylopyranosyl(1-->2)-7-O-benzoyl-beta-D-glucopyranoside (2) and 4-O-benzoyl-beta-D-xylo-pyranosyl(1-->2)-7-O-benzoyl-beta-D-glucopyranoside (3), together with nine known compounds, were isolated from the ethyl acetate extract of Pteris ensiformis. 5-[2-Hydroxyethylidene]-2(5H)-furanone (4), which had been synthesized, was isolated from natural sources for the first time. The structures of all isolated compounds were determined on the basis of mass and spectroscopic evidence. Compound 1 and pterosin B (5) show cytotoxicity against HL 60 cells (human leukemia) with the IC(50) values of 3.7 and 8.7 microg/mL, respectively.     

Biological evaluations of fatty acid esters originated during storage of Prasaplai, a Thai traditional medicine

Three fatty acid esters, (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl linoleate (1), (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl oleate (2), and (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (3), originated during storage by the interaction of components in Prasaplai, were synthesized. These three artificial esters were subjected to four biological evaluations. All three compounds were active against Mycobacterium tuberculosis H(37)Ra for which compounds 1 and 3 had inhibitory concentration at 200 microg mL(-1) while compound 2 inhibited at 100 microg mL(-1). When all these compounds were subjected to anti-HSV-1 test, compound 2 showed positive activity at 42.6 microg mL(-1) without any cytotoxic activity against human vero cell line while compound 3 had the cytotoxicity to vero cell at IC(50) 38 microg mL(-1). Compound 1 was inactive for this test.     

A novel bis-furan derivative, two new natural furan derivatives from Rehmannia glutinosa and their bioactivity

A novel bis-furan derivative and two new natural furan derivatives were isolated from the CHCl3 extracts of the dried roots of Rehmannia glutinosa (Gaerth) Lilosch. Their structures were identified as 1,5-bis(5-methoxymethyl)furan-2-yl-penta-1,4-dien-3-one 1, (E)-4-(5-(methoxymethyl)furan-2-yl)but-3-en-2-one 2 and (E)-4-(5-(hydroxymethyl)furan-2-yl)but-3-en-2-one 3 on the basis of spectral data. Moreover, biological assay showed that 1 (10 microg/mL) and 3 (10 microg/mL) can promote immune activity, 2 (100 microg/mL) and 3 (100 microg/mL) inhibit immune activity and 1 can inhibit blood platelet aggregation.     

New triterpenoid saponins from Stelmatocrypton khasianum

Four new triterpenoid saponins, designated as stelmatotriterpenosides E-H (1-4), together with three known compounds, asterbatanoside B (5), 2alpha,3beta,19alpha,23-tetrahydroxy-olean-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl ester (6) and 2alpha,3beta,19alpha,23-tetrahydroxy-urs-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl ester (7), were isolated from the stems of Stelmatocrypton khasianum. On the basis of chemical and spectral evidence, the structures of 1-4 were established as 2alpha,3beta,23-trihydroxy-olean-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (1), 2alpha,3beta,23-trihydroxy-urs-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (2), 2alpha,3beta,19alpha-trihydroxy-urs-12-en-28-oic acid-3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl ester (3), and 2beta,3beta,19alpha-trihydroxy-urs-12-en-24,28-dioic acid-24-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl diester (4).     

Constituents of Salvia microphylla

A new phenolic ester 2-( p-hydroxyphenyl)ethyl eicosaheptanoic acid ester (1) and a known one hexacosylferulate (2) were isolated from the acetone extract of Salvia microphylla. In addition, two sesquiterpenes beta-eudesmol (3) and 8alpha-hydroxy-beta-eudesmol (4), a diterpene carnosic acid 12-methyl ether (12-methoxycarnosic acid) (5), three triterpenes erithrodiol 3-acetate, oleanolic acid, lupeol and beta-sitosterol were obtained as known compounds from this plant extract. The structures of the isolated compounds were elucidated by spectroscopic methods, including one- and two- dimensional 1H- and 13C-NMR and MS spectroscopies. The selected compounds were tested for antimicrobial activity against standard bacterial strains, and only carnosic acid 12-methyl ether showed antimicrobial activity against S. aureus at 78 microg mL(-1).     

Phenylpropanoids from the stem bark of Jacaranda mimosaefolia

Two new compounds: 2-(3',4'-dihydroxyphenyl) ethyl-3-O-α-L-rhamnopyranosyl-4-O-p-hydroxyphenylacetyl-6-O-caffeoyl-β-D-glucopyranoside and 2-(3',4'-dihydroxyphenyl) ethyl-3-O-α-L-rhamnopyranosyl-4-O-piperidine-3-carboxylic acid-6-O-caffeoyl-β-D-glucopyranoside were isolated from the stem bark of Jacaranda mimosaefolia. In addition, the known compounds lupeol, betulinaldehyde, terminic acid, betulinic acid, maslinic acid, β-sitosterol glucoside and isoacteoside were isolated and identified.     

Five new bidesmoside triterpenoid saponins from Stauntonia chinensis

Eleven triterpenoid saponins (1-11) were isolated from Stauntonia chinensis DC. (Lardizabalaceae), including five new compounds, yemuoside YM(21-25) (1-3, 6, 7) structures of which were elucidated by chemical methods and a combination of MS, 1D- and 2D- NMR experiments including DEPT, (1)H--(1)H COSY, HSQC, HMBC, TOCSY, and NOESY as 3-O-alpha-L-arabinopyranosyl-(1 --> 3)-[alpha-L-rhamnopyranosyl-(1 --> 2)-]alpha-L-arabinopyranosyl-akebonicacid-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (1), 3-O-beta-D-xylopyranosyl-(1 --> 3)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-akebonic acid-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (2), 3-O-beta-D-glucopyranosyl-(1 --> 3)-alpha-L-arabinopyranosyl-akebonic acid-28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (3), 3-O-alpha-L-arabinopyranosyl-(1 --> 3)-[alpha-L-rhamnopyranosyl-(1 --> 2)-]alpha-L-arabinopyranosyl-akebonic acid-28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (6), 3-O-alpha-L-arabinopyranosyl-(1 --> 3)-[alpha-L-arabinopyranosyl-(1 --> 2)-]alpha-L-arabinopyranosyl-akebonic acid-28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester (7).     

A new pentacyclic triterpenoid glucoside from Prunus serrulata var. spontanea

A new triterpenoid, 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (4) along with four known triterpenoids, ursolic acid (1), 2alpha-hydroxyursolic acid (2), 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid (3), and 2alpha,3alpha,19alpha,24-tetrahydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (5), were isolated from the leaves of Prunus serrulata var. spontanea (Rosaceae). Compounds 3-5 showed ONOO(-) scavenging activity, whereas compounds 1 and 2 were virtually inactive.     

Terpenoid metabolites from Spongia spp. and their effects on nucleic acid biosynthesis in sea urchin eggs

19-Norspongia-13(16),14-diene-3-one (1) was isolated for the first time from a natural source, along with a series of known spongiane diterpenoids (2-11) and sesquiterpene (12) from two unidentified species belonging to the genus Spongia. The effects of 1, 4, 5, 8-12 on biosynthesis of nucleic acids and embryonic development of the sea urchin Strongylocentrotus intermedius have been studied. All the compounds inhibit sea urchin embryo development at concentration of 20 microg/mL and above and DNA biosynthesis at the dose of 10 microg/mL. The inhibitory effect of diterpenoids at least partly may be explained by the inhibition of thymidine kinase activity.     

Bioactive isocoumarins from a terrestrial Streptomyces sp. ANK302

Four isocoumarins have been isolated from the terrestrial Streptomyces sp. ANK302, namely 6,8-dimethoxy-3-methylisocoumarin (1), 6,8-dihydroxy-3-methylisocoumarin (2), 6,8-dihydroxy-7-methoxy-3-methylisocoumarin (3), and 6,7,8-trimethoxy-3-methylisocoumarin (4). Compound 1 is a new naturally-occurring isocoumarin, and 2 was isolated as a new bacterial product. The structures 1-4 were deduced from high resolution mass, 1D and 2D NMR spectra and by comparison with related compounds from the literature. Compound 2 showed a strong zoosporicidal activity at a concentration of 5 microg/mL against a phytopathogenic oomycete, Plasmopara viticola, and 1 was active against     

Chemical composition of Argentinean propolis collected in extreme regions and its relation with antimicrobial and antioxidant activities

This paper reveals, for the first time, the functional properties of propolis from an extreme region of Argentine (El Rincón, Province of Catamarca, Argentina), as well as the isolation and identification of bioactive compounds. The antioxidant activity was determined by the ABTS method and beta-carotene bleaching. The antibacterial activity was determined on methicillin resistant Staphylococcus aureus (MRSA) by the microdilution method and bioautographic assays. Twelve compounds were isolated and identified by NMR spectroscopy. The main bioactive compounds were 2',4'-dihydroxy-3'-methoxychalcone (3), 2',4'-dihydroxychalcone (9), 2',4',4-trihydroxy-6'- methoxychalcone (8), 5-hydroxy-4',7-dimethoxyflavone (4), 4',5-dihydroxy-3,7,8-trimethoxyflavone (10) and 7-hydroxy- 5,8-dimethoxyflavone (11). All compounds were active against clinical isolates (MIC50 10 microg/mL) and displayed antioxidant activity (SC50 values of 20 microg/mL). The MIC and SC50 values of the isolated compounds were lower than those obtained with crude propolis extracts, chloroform sub-extracts and isolated fractions.     

Four novel insecticidal sesquiterpene esters from Celastrus angulatus

Four new insecticidal sesquiterpene polyol esters with a beta-dihydroagarofuran sesquiterpene skeleton, celangulatin C (1), celangulatin D (2), celangulatin E (3), and celangulatin F (4), and five known compounds 5-9 were isolated from the low-polar toluene extracts of the root bark of Celastrus angulatus by bioassay-guided fractionation. Their chemical structures were elucidated mainly by analyses of MS and NMR spectral data. Celangulatin C, E and F showed LD(50) against Mythimna separata were 280.4, 1656.4 and 210.5 microg mL(-1), respectively.     

Activity against Streptococcus pneumoniae of the essential oil and 5-(3-buten-1-ynyl)-2, 2'-bithienyl isolated from Chrysactinia mexicana roots

The essential oil of Chrysactinia mexicana retrieved from the root bark was characterized by gas chromatography coupled to a mass detector. The compounds silphiperfol-5-ene, 7-epi- silphiperfol-5-ene, modheph-2-ene, alpha-isocomene, beta-isocomene and methyl-linoleate were identified. The principal compound (76.42%) could not be identified by the library and was further isolated through a reverse phase C-18 chromatography followed by silica gel chromatography and identified as 5-(3-buten-1-ynyl)-2,2'-bithienyl. Both the oil and the isolated compound were tested for their antimicrobial activity against two strains of Streptococcus pneumoniae resistant to beta-lactam antibiotics. MICs were 250 microg/mL and 125 microg/mL respectively. This is the first report about extraction of oil and compound 5-(3-buten-1-ynyl)-2, 2'-bithienyl from roots of Chrysactinia mexicana as well as the determination of antimicrobial activity against S. pneumoniae.     

Phosphodiesterase-I inhibitor quinovic acid glycosides from Bridelia ndellensis

Quinovic acid-3-O-alpha-L-rhamnopyranoside (1), quinovic acid-3-O-beta-D-fucopyranoside (2), quinovic acid-3-O-beta-D-glucopyranosyl (1 --> 4)-beta-D-fucopyranoside (3), methyl gallate (4) and ethyl gallate (5) were isolated from the ethyl acetate extract of Bridelia ndellensis barks by fractionation. Compounds 1-3 showed significant inhibitory activity against snake venom phosphodiesterase-I.     

Anti-babesial compounds from Curcuma xanthorrhiza

Anti-babesial ingredients, (12R)- and (12S)-12,13-dihydro-12,13-dihydroxyxanthorrhizols, were isolated from Curcuma xanthorrhiza. The structures were established by the extensive NMR techniques. The assignments of (1)H NMR data of (12R)-12,13-dihydro-12,13-dihydroxyxanthorrhizol was revised, and (12S)-12,13-dihydro-12,13-dihydroxyxanthorrhizol was isolated as a pure form for the first time. The IC(50) of the active compounds were compared with that of commercial drug, diminazene aceturate (Ganaseg). IC(50) values of Ganaseg, (12R)-, and (12S)-12,13-dihydro-12,13-dihydroxyxanthorrhizols were 0.6 microg mL(-1), 8.3 microg mL(-1) and 11.6 microg mL(-1), respectively.     

In vitro antitumor activity of triterpenes from Ceriops tagal

The embryo of Ceriops tagal was extracted with 95% ethanol at room temperature, and four triterpenes (1-4) were separated from this extract. For the first time these triterpenes were the separated from this plant. Compounds (1-4) were tested in vitro for antitumor activity against three cell lines (human liver cancer cell (H-7402), human B-lymphoblastoid cell (Raji), and human cervical carcinoma cell (Hela)). Compounds 1 and 3 were effective to inhibit cell proliferation and growth of H-7402 and Hela, the IC(50) of them on H-7402 were 14.42 microg mL(-1) and 9.97 microg mL(-1), and the IC(50) of them on Hela were 11.84 microg mL(-1) and 11.32 microg mL(-1). All compounds 1-4 were not effective to inhibit cell proliferation and growth of Raji. The effects of compound 4 on inhibiting proliferation and growth of these three cancer cells was also not obvious.     

Glycosides from the leaves of Ilex hylonoma

Two new triterpenoid saponins, hylonosides I-II (1,2) have been isolated along with one known flavonoid glycoside (3) from the methanol extract of leaves of Ilex hylonoma. The structures were elucidated by ID and 2D NMR experiments, including 1H-1H COSY, TOCSY, NOESY, HMQC, and HMBC methods. Two new compounds were characterized as 3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucuronopyranosyl pomolic acid-28-O-beta-D-glucopyranoside (1), 3-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl pomolic acid-28-O-beta-D-glucopyranoside (2).     

Chemical composition and antimicrobial activity of the volatile oil from Fusarium tricinctum, the endophytic fungus in Paris polyphylla var. yunnanensis

The volatile oil, obtained by hydro-distillation from Fusarium tricinctum, the endophytic fungus isolated from Paris polyphylla var. yunnanensis, was analyzed by gas chromatography-mass spectrometry (GC-MS). trans-1,2,3,3a,4,7a-Hexahydro-7a-methyl-5H-inden-5-one (73.1%), 2-methylene-4,8,8-trimethyl-4-vinyl bicyclo [5.2.0] nonane (12.0%), and 2,6-dimethyl-6-(4-methyl-3-pentenyl) bicyclo [3.1.1] hept-2-ene (4.5%) were the major compounds of the 15 identified components accounting for 95.4% of the volatile oil. The antimicrobial activity of the volatile oil was assayed against eight bacteria and two fungi. The minimum inhibitory concentration (MIC) values of the volatile oil against the test bacteria ranged from 25 to 45 microg/mL. The MIC values against the fungi Candida albicans and Magnaporthe oryzae were 100 and 225 microg/mL, respectively. The mean inhibitory concentration (IC50) values of the volatile oil against the test bacteria ranged from 17.8 to 31.6 microg/mL, and those of the volatile oil against C. albicans and M. oryzae were 84.3 and 204.3 microg/mL, respectively.