Artoindonesianin P,a new prenylated flavone with cytotoxic activity from Artocarpus lanceifolius

A new prenylated flavone, named artoindonesianin P (1), was isolated from the tree bark of Artocarpus lanceifolius, together with three known related compounds, artobiloxanthone (2), cycloartobiloxanthone (3) and artonol B (4). The structure of artoindonesianin P 1 was determined on the basis of spectral evidence (MS, 1H and 13C NMR) and by comparison with known related compounds. Compounds 1-4 exhibited significant cytotoxicity against murine P388 leukemia cells.     

Anti-tumor promoters phenolics and triterpenoid from Hippophae rhamnoides

A 70% ethanol extract of the branches of Hippophae rhamnoides exhibited remarkable antitumor activity in an in vivo two-stage carcinogenesis test in mice using 7,12-dimethylbenz[a]anthracene as an initiator and 12-O-tetradecanoylphorbol-13-acetate (TPA) as a promoter. From the active fraction of the 70% ethanol extract, three phenolic compounds, (+)-catechin (1), (+)-gallocatechin (2), and (−)-epigallocatechin (3) and a tritepenoid, ursolic acid (4) were isolated and identified. These compounds were evaluated for their inhibitory effects on TPA-induced inflammation (1 µg/ear) in mice. Within the tested compounds, 3 and 4 showed marked anti-inflammatory effects, with a 50% inhibitory dose of 1.7 and 0.2 μmol/ear.     

Artoindonesianin L, a new prenylated flavone with cytotoxic activity from Artocarpus rotunda.

A new prenylated flavone, named artoindonesianin L (1), was isolated from Artocarpus rotunda (Hout) Panzer (Moraceae). Its structure was elucidated as on the basis of spectroscopic evidence. Along with this new compound, four known phenolic compounds were also isolated from this plant and identified as artonins M (2) and E (3), cycloartobiloxanthone (4) and artonin O (5). All these compounds showed significant cytotoxicity against murine P388 leukemia cells.     

A novel cytotoxic flavonoid glycoside from Physalis angulata.

A new flavonol glycoside, myricetin 3-O-neohesperidoside (1) was isolated from a cytotoxic MeOH extract of the leaves of Physalis angulata. Compound 1 showed remarkable cytotoxicity in vitro against murine leukemia cell line P-388, epidermoid carcinoma of the nasopharynx KB-16 cells, and lung adenocarcinoma A-549 with ED(50) values of 0.048, 0.50 and 0.55 microg ml(-1), respectively.     

A new cytotoxic guaianolide from Chrysanthemum boreale

A new cytotoxic guaianolide was isolated from Chrysanthemum boreale Makino. The structure of guaianolide was elucidated as 8-acetoxy-4,10-dihydroxy-2,11(13)-guaiadiene-12,6-olide (1). Compound 1 exhibited cytotoxic activity (IC(50)< or =4 microg/ml) against all five human cancer cell lines tested.     

Cytotoxic resveratrol oligomers from the tree bark of Dipterocarpus hasseltii

A new resveratrol tetramer, named diptoindonesin E, was isolated from the acetone extract of the tree bark of Dipterocarpus hasseltii, together with five known resveratrol oligomers (-)-epsilon-viniferin, laevifonol, (-)-alpha-viniferin, vaticanol B, (-)-hopeaphenol, and a coumarin, scopoletin. The structures of these compounds were determined from spectroscopic evidence. Cytotoxicity test of the isolated compounds showed that hopeaphenol strongly inhibited murine leukemia P-388 cells.     

Artoindonesianin L, a new prenylated flavone with cytotoxic activity from Artocarpus rotunda

A new prenylated flavone, named artoindonesianin L (1), was isolated from Artocarpus rotunda (Hout) Panzer (Moraceae). Its structure was elucidated as on the basis of spectroscopic evidence. Along with this new compound, four known phenolic compounds were also isolated from this plant and identified as artonins M (2) and E (3), cycloartobiloxanthone (4) and artonin O (5). All these compounds showed significant cytotoxicity against murine P388 leukemia cells.     

Anti-diabetic potential of ursolic acid stearoyl glucoside: a new triterpenic gycosidic ester from Lantana camara

A new stearoyl glucoside of ursolic acid, urs-12-en-3β-ol-28-oic acid 3β-d-glucopyranosyl-4′-octadecanoate and other compounds were isolated from the leaves of Lantana camara L. The structure of this new glycoside was elucidated and established by standard spectroscopic methods. In streptozotocin-induced diabetic rats it showed significant reduction in blood glucose level.     

Bakkenolides from Petasites tatewakianus

A new bakkenolide and a known one were isolated from Petasites tatewakianus. The structure of the new compound was elucidated on the basis of spectroscopic methods including IR, EIMS, HRESIMS, 1D and 2D NMR, and the known compound was established by single crystal X-ray structural analysis. The in vitro cytotoxic activity of these two compounds against cultured human cervical carcinoma (HeLa), human breast cancer (MCF-7) and murine Lewis lung carcinoma (LLC) cell lines was also evaluated.     

Two new cytotoxic triterpenoid saponins from the roots of Clematis argentilucida

Bioassay-guided fractionation of the n-BuOH extract of the roots of Clematis argentilucida led to the isolation of two new triterpenoid saponins along with a known one, cussonside B (3). By extensive spectral analysis and chemical evidences, the structures of the two new saponins were determined to be 3β-O-[β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] hederagenin-11,13-dien-28-oic acid (1) and 3β-O-{β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-xylopyranosyl} oleanolic acid (2), respectively. Saponin 1 is the first example of triterpenoid saponins with two double bonds located at C-11 and C-13 in the aglycone from the genus Clematis. The two new saponins exhibited significant cytotoxicity against human leukemia HL-60 cell lines, human hepatocellular carcinoma Hep-G2 cell lines and human glioblastoma U251MG cell lines with a range of IC(50) values from 2.74 to 25.40μM, while 3 showed inactivity against all of the three cancer cell lines.     

Andirolides Q–V from the flower of andiroba (Carapa guianensis,Meliaceae)

Two new gedunins, an andirobin, two mexicanolides, and a phragmalin-type limonoid, named Andirolides Q (1), R (2), S (3), T (4), U (5), and V (6), were isolated from an oil of the flower of Carapa guianensis AUBLET (Meliaceae). Their structures have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Andirolide S (3) and Andirolide T (4) showed significant cytotoxic activity against the murine P388 leukemia cell line (IC₅₀ of 1.4 μM for 3; 1.8 μM for 4) and the human HL-60 leukemia cell line (IC₅₀ of 1.3 μM for 3 and 4).     

Bioactive phenolics from the fruits of Livistona chinensis

This study investigated the antioxidant and cytotoxic activity of the phenolics isolated from the fruits of Livistona chinensis. Four new compounds, 1-{ω-isoferul[6- (4-hydroxybutyl)pentadecanoic acid]}-glycerol (1), E-[6′-(5″-hydroxypentyl)tricosyl]-4-hydroxy-3-methoxycinnamate (2), 2-(3′-hydroxy-5′-methoxyphenyl)-3-hydroxylmethyl-7-methoxy-2,3-dihydrobenzofuran-5- carboxylic acid (3), 7-hydroxy-5,4′-dimethoxy-2-arylbenzofuran (4), together with eleven known phenolics (5-15), were isolated and identified. Among these compounds, 1-4, 5-O-caffeoylshikimic acid (5), caffeic acid (7), and 3-O-caffeoylshikimic acid (8) showed potent antioxidant activity. 1-5, and 8 showed potent antiproliferative activities with IC₅₀ values among 5-150 μM against HepG2 human liver cancer, HL-60 human myeloid leukemia, K562 human myeloid leukemia, and CNE-1 human nasopharyngeal carcinoma cell lines. On the basis of these findings, it could be proposed that the fruits of L. chinensis may serve as attractive mines of powerful anticancer and antioxidant agents for various purposes.     

Bioactive flavones and biflavones from Selaginella moellendorffii Hieron

Three new flavones named 5-carboxymethyl-4′,7-dihydroxyflavone (1), its ethyl ester (2) and butyl ester (3) were isolated from the herb Selaginella moellendorffii Hieron., together with ten known compounds. Their structures were elucidated on the basis of spectroscopic and chemical analysis. Selected compounds were evaluated for their anti-HBV and cytotoxic activity. Among them, compounds 2 and 3 displayed inhibitory activity in vitro on hepatitis B virus (HBV) surface antigen (HBsAg) secretion of the Hep G2.2.15 cell line with IC₅₀ values of 0.17 mg/ml and 0.46 mg/ml, and on HBV e antigen (HBeAg) secretion with IC₅₀ values of 0.42 mg/ml and 0.42 mg/ml, respectively. Compounds 7, 8, 10 and 12 exhibited selective cytotoxicity against the three human cancer cell lines tested.     

Four new phenanthrenes from Monomeria barbata Lindl

Three biphenanthrene compounds (1–3) and a triphenanthrene compound (4), together with six known biphenanthrene compounds (5–10), were isolated from the tubers of Monomeria barbata Lindl. Their structures were elucidated on the basis of extensive spectroscopic analysis (1D-, 2D-NMR, and HR-ESI-MS). These four new compounds were tested in vitro for the cytotoxic activity against liver carcinoma (HepG-2), promyelocytic leukaemia (HL60), ovarian carcinoma (Skov-3) and epidermoid carcinoma (A431) cancer cell lines and the antioxidant activity in DPPH radical scavenging. Compounds 1–4 exhibited significant cytotoxic activity against HepG-2 and HL60 cell lines, and potent antioxidant activity in DPPH radical scavenging.     

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.     

Antiproliferative activity of Citrus juices and HPLC evaluation of their flavonoid composition

The antiproliferative activity of fresh fruit juices extracted from Citrus sinensis (cv. Washington Navel and cv. Sanguinello), C. deliciosa cv. Avana, C. clementina cv. Nules, C. aurantium subsp. myrtifolia , was evaluated against K562 (human chronic myelogenous leukemia), HL-60 (human leukemia) and MCF-7 (human breast adenocarcinoma) cell lines. All the juices tested showed antiproliferative activity. Moreover, the pattern of the main flavanone compounds in the juices has been determined by HPLC analysis.     

An unusual taxodione derivative from hairy roots of Salvia austriaca

From a root culture of Salvia austriaca, transformed with Agrobacterium rhizogenes, a new diterpenoid was isolated and its chemical structure was determined as 7-(2-oxohexyl)-11-hydroxy-6, 12-dioxo-7,9(11),13- abietatriene [= 7-(2-oxohexyl)-taxodione] on the basis of spectroscopic methods, especially 1D and 2D NMR, and by comparison with structurally related compounds. This compound represents a hitherto unknown 2-oxohexyl diterpenoid derivative. Cytotoxic studies revealed that the new compound exhibited high cytotoxic activity against three cancer cell lines with IC(50) values ranging from 0.63 to 0.72μM. Its cytotoxic effectiveness against the cancer cells was ten fold higher than that of taxodione.     

Protection against neurodegenerative diseases of Iris pseudopumila extracts and their constituents

The present study describes for the first time the in vitro properties of Iris pseudopumila flowers and rhizomes extracts and their constituents. The methanolic extract of rhizomes showed significant anti-inflammatory activity through inhibition of NO production in the murine monocytic macrophage cell line RAW 264.7. Among the isolated compounds, those which most effectively inhibited LPS-induced NO production were irisolidone and 7-methyl-tectorigenin-4′-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside], with IC₅₀ values of 23.6 μM and 29.4 μM respectively. Isoorientin and isovitexin exhibited the most promising activity against AChE with IC₅₀ of 26.8 μM and 36.4 μM, respectively. The same compounds exhibited also the higher activity against BChE.     

Cytotoxicity of cycloartane triterpenoids from aerial part of Cimicifuga foetida

Our previous study had demonstrated cytotoxicity of EtOAc fraction from aerial part of Cimicifuga foetida on various cancer cell lines. In the present study, we investigated the cytotoxicity of five cycloartane triterpenoids isolated from the EtOAc fraction. Compounds (1,2,3) showed moderate cytotoxic activity on R-HepG2 cells and drug resistant sub line R-HepG2 but exhibited less toxicity against primary cultured normal mouse hepatocytes. Compounds (4) and (5) were inactive on all tested cell lines.