A new triterpenoid from <Emphasis Type="Italic">Brucea javanica</Emphasis>

A new triterpenoid, bruceajavanin C (1), together with bruceosides A and B (2 and 3), bruceines D and E (4 and 5), yadanziosides A and G (6 and 7), (20R)-O-(3)-α-L-arabinopyranosylpregn-5-ene-3β,20-diol (8), and α-D-glucopyranoside, (3β, 20R)-3-hydroxypregn-5-en-20-yl (9) were isolated from the aerial parts of Brucea javanica. The structure of 1 was elucidated on the basis of 2D-NMR spectroscopic analysis. In addition, compounds 1, 3, 4, 5, and 6 exhibited mild inhibitory effect on NO production in LPS-stimulated RAW264.7 cells.     

One new pregnane glycoside from the seeds of cultivated <Emphasis Type="Italic">Brucea javanica</Emphasis>

A new pregnane glycoside, named (20R)-O-(3)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-pregn-5-en-3β,20-diol (1), and seven known compounds, brusatol (2), bruceine B (3), bruceine D (4), yadanziolide A (5), bruceine E (6), yadanzioside G (7), and yadanzioside B (8), were isolated from the cultivated dry seeds of Brucea javanica. The structure of 1 was elucidated on the basis of 1D- and 2D-NMR spectroscopic analyses. Their inhibitory effects on tumor cells were also tested. Compound 1 was slightly active against HL-60, SMMC-7721, A-549, and MCF-7 tumor cells. Compounds 2 and 3 demonstrated significant inhibitory activities against all tested cells. These results indicate that cultivated B. javanica could replace the wild plant as an antitumor plant resource.     

Two new antibacterial norabietane diterpenoids from cyanobacteria, <Emphasis Type="Italic">Microcoleous </Emphasis><Emphasis Type="Italic">lacustris</Emphasis>

Two abietane diterpenes were isolated from cyanobacteria Microcoleous lacustris, 20-nor-3α-acetoxyabieta-5,7,9,11,13-pentaene and 20-nor-3α-acetoxy-12-hydroxy-abieta-5,7,9,11,13-pentaene. These compounds were assayed against Staphylococcus aureus, Staphylococcus epidermidis, Salmonella typhi, Vibrio cholerae, Bacillus subtilis, Bacillus cereus, Escherichia coli, and Klebsiella pneumoniae. Both compounds showed activity against S. aureus, S. epidermidis, S. typhi, and V. cholerae, but not against the other bacteria.     

A new <Emphasis Type="Italic">Erythrina</Emphasis> alkaloid from <Emphasis Type="Italic">Erythrina herbacea</Emphasis>

A new Erythrina alkaloid, 10-hydroxy-11-oxoerysotrine (1), has been isolated from the flowers of Erythrina herbacea together with five known compounds: erytharbine (2), 10,11-dioxoerysotrine (3), erythrartine (4), erysotramidine (5) and erysotrine-N-oxide (6). The structure of the new compound was elucidated on the basis of its spectral data, including 2-D NMR and mass (MS) spectra. The new compound is a rare C-10 oxygenated Erythrina alkaloid. The antioxidant activities of the isolated compounds 1–6 were evaluated by scavenging with peroxynitrite.     

Two new monoterpene alkaloid derivatives from the roots of <Emphasis Type="Italic">Incarvillea arguta</Emphasis>

Two new monoterpene alkaloid derivatives, incargutosines C (1) and D (2), together with a known compound, argutine A (3) have been isolated from the roots of Incarvillea arguta Royle. The structures of 1 and 2 were established on the basis of 1D and 2D NMR spectroscopic analysis, while the absolute configurations of 1 and 2 were determined by a synthetic method. In addition, the cytotoxicity of 3 was evaluated using four tumor cell lines, A549, LOVO, 6TCEM, and MDA-MB-435 (MDA) by the MTT assay.     

A new lignan glucoside from the stems of <Emphasis Type="Italic">Callicarpa japonica</Emphasis> Thunb. var. <Emphasis Type="Italic">luxurians</Emphasis> Rehd.

A new lignan glucoside (1) was isolated from the stems of Callicarpa japonica Thunb. var. luxurians Rehd. (Verbenaceae), along with six known lignan glucosides and three known triterpenoids. The chemical structure of 1 was characterized as (+)-lyoniresinol 3α-O-(6″-3,5-dimethoxy-4-hydroxybenzoyl)-β-d-glucopyranoside on the basis of spectroscopic data. In addition, the radical-scavenging effect of four lignans on the stable free radical 1,1-diphenyl-2-picrylhydrazyl was examined. Among the tested compounds, three compounds, including 1, showed almost the same scavenging activity as that of α-tocopherol.     

Rearranged <Emphasis Type="Italic">ent</Emphasis>-kauranes from the stems of <Emphasis Type="Italic">Tricalysia dubia</Emphasis> and their biological activities

From the EtOAc-soluble fraction of an MeOH extract of the stems of Tricalysia dubia, two new rearranged ent-kaurane derivatives, named tricalysiolides H and I, were isolated, together with five known rearranged ent-kauranes, i.e. tricalysiolides A–E, stigmast-4-en-6β-ol-3-one, (+)-pinoresinol, scopoletin and syringaldehyde. Their structures were elucidated from spectroscopic evidence, and their cytotoxicity toward KB cells and P-gp inhibitory activity were assayed.     

A new triterpene glycoside from the stems of <Emphasis Type="Italic">Lagerstroemia indica</Emphasis>

A bioassay-guided fractionation and chemical investigation of the stems of Lagerstroemia indica resulted in the isolation and identification of a new triterpene glycoside, lagerindiside (1), along with nine known triterpenes (2–10). The structure of this new compound was elucidated on the basis of 1D and 2D nuclear magnetic resonance spectroscopic data analysis as well as chemical method. The cytotoxic activities of the isolates (1–10) were evaluated by determining their inhibitory effects on four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15) using a sulforhodamine B bioassay. Compounds 3 and 4 showed potent cytotoxicity on the tumor cell lines with IC₅₀ values ranging from 3.38 to 6.29 μM.     

Two new triterpenoid acids from <Emphasis Type="Italic">Kadsura coccinea</Emphasis>

An investigation of EtOAc extracts of Kadsura coccinea (Lem.) A. C. Smith, has led to the isolation of two new compounds characterized as 3-hydroxy-12-hydroxyl coccinic acid (1) and 3-hydroxy-neokadsuranic acid A (2). Their structures were established by 1D and 2D NMR techniques and mass spectroscopy. Antiproliferative effects of the isolated compounds were evaluated against four human tumor cell lines (A549, HCT116, HL-60 and HepG2), and it was found that compound 1 exhibited antiproliferative effects with IC₅₀ values ranging from 3.01 to 18.08 μg/mL.     

Two new acorane sesquiterpenes from <Emphasis Type="Italic">Illicium henryi</Emphasis>

Two new acorane sesquiterpenes, 10-hydroxyacoronene (1) and 1β-isopropyl-4β-methyl-9β-hydroxy spiro[4.5]dec-6-en-8-one (2), one new natural product, 4-hydroxy-4, 6-dimethyl-1-tetralone (3), and one known acorane sesquiterpene, acoradiepoxide (4) were isolated from the twigs and leaves of Illicium henryi. The structures of the new compounds were elucidated primarily on the basis of analysis of spectroscopic data. In addition, the inhibitory effect on NO production of these compounds were tested. Compounds 1 and 4 exhibited slight inhibitory effects on NO production with IC₅₀ values of 82.4 μg/mL and 76.5 μg/mL, respectively.     

Two new phenolic glycosides from <Emphasis Type="Italic">Syringa reticulata</Emphasis>

Two new phenolic glycosides—3′-O-β-d-glucopyranosysalidroside (1) and cis-echinacoside (2)—together with four known ones—forsythoside B (3), decaffeoylacteoside (4), osmanthuside F (5) and (−)-olivil-4′-O-β-d-glucopyranoside (6)—were isolated from the leaves of Syringa reticulata. Their structures were established on the basis of spectral and chemical data.     

<Emphasis Type="Italic">ent</Emphasis>-Abietane diterpenoids from <Emphasis Type="Italic">Isodon xerophilus</Emphasis>

Three new ent-abietanoids, named xerophilusins XIV–XVI, and four known analogues, as well as four known chemical constituents were isolated from the leaves of Isodon xerophilus. Their structures were elucidated by extensive spectroscopic studies, and comparison with literature data. In addition, the cytotoxic activity of the ent-abietanoids against chronic myelogenous leukemia (K562), stomach adenocarcinoma (MKN45), and hepatocellular carcinoma (HepG2) human cell lines was investigated and no activities were observed.     

<Emphasis Type="Italic">In Vitro</Emphasis> hepatoprotective compounds from <Emphasis Type="Italic">Suaeda glauca</Emphasis>

Bioassay-guided fractionation of the MeOH extract of Suaeda glauca yielded four phenolic compounds, methyl 3,5-di-O-caffeoyl quinate (1) and 3,5-di-O-caffeoyl quinic acid (2), isorhamnetin 3-O-beta-D-galactoside (3), and quercetin 3-O-beta-D-galactoside (4). Compounds 1 and 2 were hepatoprotective against tacrine-induced cytotoxicity in human liver-derived Hep G2 cells with the EC(50) values of 72.7+/-6.2 and 117.2+/-10.5 microM, respectively. Silybin as a positive control showed an EC(50) value of 82.4+/-4.1 microM.     

Three new <Emphasis Type="Italic">C</Emphasis>-glycosyflavones with acetyl substitutions from <Emphasis Type="Italic">Swertia mileensis</Emphasis>

Three new acetylated C-glycosylflavones, 3″,6″-di-O-acetylswertiajaponin (1), 4″,6″-di-O-acetylswertiajaponin (2), and 6″-O-acetylswertiajaponin (3), together with six known compounds were isolated from the whole herb of Swertia mileensis. Their structures were elucidated on extensive NMR experiments and mass spectrometry studies. ¹H and ¹³C NMR data exhibited doublet signals at room temperature. Variable temperature ¹H NMR experiments were carried out to investigate the presence of rotational isomerism of C-glycosylflavones. All compounds showed potential antioxidant activities against apoptosis of H₂O₂-induced human embryo liver L02 cells.     

Two new phenylpropane glycosides from <Emphasis Type="Italic">Allium tuberosum</Emphasis> Rottler

A phytochemical investigation of Allium tuberosum Rottler afforded two new phenylpropane glycosides, named tuberonoid A (1) and B (2), along with four known flavonoids, kaempferol 3-O-β-sophoroside (3), 3-O-β-d-(2-O-feruloyl)-glucosyl-7,4′-di-O-β-d-glucosylkaempferol (4), 3-O-β-sophorosyl-7-O-β-d-(2-O-feruloyl)glucosyl kaempferol (5), kaempferol 3,4′-di-O-β-d-glucoside (6). The identification and structural elucidation of the new compounds were carried out based on spectral data analyses (¹H and ¹³C NMR, ¹H–¹H COSY, HMQC) and HR-MS.     

Two new ursane-type triterpenoid saponins from <Emphasis Type="Italic">Elsholtzia bodinieri</Emphasis>

Two new ursane-type triterpenoid saponins, bodiniosides M (1) and N (2), along with three known saponins, oblonganosides I (3), pseudobuxussaponin B (4) and bodinioside A (5), were isolated from the aerial parts of Elsholtzia bodinieri. The structures of compounds 1 and 2 were characterized by spectroscopic data as well as acid hydrolysis and GC analysis as 3-O-β-d-xylopyranosyl-19α-hydroxy-23-acetoxy-urs-12(13)-en-28-oic acid 28-O-α-l-rhamnopyranosyl-(1-2)-β-d-glucopyranoside and 3-O-β-d-glucopyranosyl-2α,19α-dihydroxy-urs-12(13)-en-28,20β-lactone. Compounds 1 and 5 exhibited potent anti-HCV activities in vitro with a selective index of 6.53 and 4.41, respectively.     

Two new quinones from the roots of <Emphasis Type="Italic">Juglans mandshurica</Emphasis>

Two new quinones, 1-hydroxy-5-pentyl-anthraquinone (1) and 4-(5-hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-ylamino)-butyric acid methyl ester (2), together with two known quinones, 5-hydroxy-2-(2-hydroxy-ethylamino)-(1,4) naphthoquinone (3) and juglone (4) were isolated from the roots of Juglans mandshurica (Juglandaceae). Their structures were elucidated on the basis of spectral data. Compound 3 was isolated from the Juglans genus for the first time. Compounds 1–4 exhibited significant cytotoxicity towards cultured MDA-MB231, HepG2 and SNU638 cells with IC₅₀ values ranging from 4.46 to 88.47 μM.     

Novel cycloartane-type triterpenoid from the fruits of <Emphasis Type="Italic">Nandina</Emphasis><Emphasis Type="Italic">domestica</Emphasis>

A novel cycloartane-type triterpenoid was isolated from the fruits of Nandina domestica (Berberidaceae). The structure was characterized as 24-methylene-3-oxocycloartane 13-carboxylic acid on the basis of NMR spectroscopic data.     

Constituents of the stems and fruits of<Emphasis Type="Italic">Opuntia ficus-indica</Emphasis> var.<Emphasis Type="Italic">saboten</Emphasis>

From the stems and fruits of Opuntia ficus-indica var. saboten, eight flavonoids, kaempferol (1), quercetin (2), kaempferol 3-methyl ether (3), quercetin 3-methyl ether (4), narcissin (5), (+)-dihydrokaempferol (aromadendrin, 6), (+)-dihydroquercetin (taxifolin, 7), eriodictyol (8), and two terpenoids, (6S,9S)-3-oxo-alpha-ionol-beta-D-glucopyranoside (9) and corchoionoside C (10) were isolated and identified by means of chemical and spectroscopic. Among these isolates, compounds 3-5 and 8-10 were reported for the first time from the stems and fruits of O. ficus-indica var. saboten.     

Biologically active <Emphasis Type="Italic">C</Emphasis>-alkylated flavonoids from <Emphasis Type="Italic">Dodonaea viscosa</Emphasis>

A new C-alkylated flavonoid (5,7-dihydroxy-3′-(4″-acetoxy-3″-methylbutyl)-3,6,4′-trimethoxyflavone (1), along with two known C-alkylated flavonoids (5,7-dihydroxy-3′-(3-hydroxymethylbutyl)-3,6,4′-trimethoxyflavone (2), 5,7,4′-trihydroxy-3′-(3-hyroxymethylbutyl)-3,6-dimethoxyflavone (3) and two new source C-alkylated flavonoids (5,7-dihydroxy-3′-(2-hydroxy-3-methyl-3-butenyl)-3,6,4′-trimethoxyflavone (4), 5,7,4′-trihydroxy-3,6-dimethoxy-3′-isoprenyl-flavone (5) were isolated from the aerial parts of Dodonaea viscosa. The structures of all compounds were established on the basis of 1D and 2D NMR spectroscopy and mass spectrometry. The isolated compounds were evaluated for their inhibitory effect on urease and α-chymotrypsin enzyme. All the compounds (1–5) exhibited mild inhibition against urease but remained recessive in case of α-chymotrypsin.