Antiproliferative steroidal glycosides from Digitalis ciliata

Two new compounds, a furostanol glycoside (1) and a pregnane glycoside (4), along with eight known compounds, belonging to the classes of spirostane (2,3), pregnane (5–7) and cardenolide (8–10) glycosides, were isolated from the seeds of Digitalis ciliata. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. For the first time pregnane glycosides of the diginigenin series have been isolated from D. ciliata. The cytotoxic effects of compounds 1–10 on cell viability of several cancer cell lines, namely human breast cancer (MCF-7), human glioblastoma (T98G), human lung adenocarcinoma (A549), human colon carcinoma (HT-29), and human prostate cancer (PC-3) cell lines were evaluated. Compounds 1, 4, 7 and 8 showed antiproliferative effects against MCF-7, HT-29 and A549 cancer cells with IC₅₀ values ranging from 8.3 to 20 μM. The effects of compounds 1–10 on cell proliferation were evaluated on these three cancer cell lines by cell cycle analysis of DNA content using flow cytometry. Compounds 7, 8 and 10 induced significant changes in G₂/M cell cycle phase of all analyzed cells. The obtained results indicate that compounds 7, 8 and 10 are cytostatic compounds effective in reducing cell proliferation by inducing accumulation of the cells in the G₂/M phase of the cell cycle.     

Nepetalactone content in shoot cultures of three endemic Nepeta species and the evaluation of their antimicrobial activity

Rapid micropropagation of Nepeta rtanjensis, N. sibirica and N. nervosa was performed. Qualitative and quantitative nepetalactone content in methanol extracts of in vitro grown plants was analysed by reverse-phase HPLC coupled with UV and MS detection. Only trans,cis-nepetalactone was detected in shoots of N. rtanjensis, while cis,trans-nepetalactone stereoisomer was present in N. sibirica. No nepetalactone was observed in shoots of N. nervosa. The antimicrobial activity of methanol extracts, against eight bacterial and eight fungal species, was evaluated. All the tested extracts showed significant antibacterial and strong antifungal activity. However, N. rtanjensis extract exhibited the best antimicrobial potential.     

Chemical composition and antimicrobial activity of Momordica charantia seed essential oil

The essential oil obtained from the seeds of Momordica charantia was analyzed by GC/MS. Twenty-five components, representing 90.9% of the oil, were identified. The main constituents were trans-nerolidol, apiole, cis-dihydrocarveol and germacrene D. Furthermore, the oil was tested for its antibacterial and antifungal activities. Staphylococcus aureus was found to be the most sensitive microorganism with MIC values <500 microg/ml.     

Chemical composition and antimicrobial activity of Chamaecyparis obtusa leaf essential oil

The essential oil obtained from the leaves of Chamaecyparis obtusa was analyzed by GC and GC-MS. alpha-Terpinyl acetate, sabinene, isobornyl acetate and limonene were found to be the major components. The oil showed relatively strong antibacterial activities against Gram (+) bacteria and some fungi.     

Diarylheptanoids from the rhizomes of Alpinia officinarum and their anticancer activity

Two new diarylheptanoids (1, 2), together with two known analogs (3, 4), were isolated from the rhizomes of Alpinia officinarum. The new compounds were elucidated to be (5S)-5-hydroxy-7-(3, 4-dihydroxyphenyl)-1-phenyl-3-heptanone (1) and (5R)-5-hydroxy-7-(3-methoxy-4, 5-dihydroxyphenyl)-1-phenyl-3-heptanone (2) based on their spectral analysis. Compound 4 showed moderate cytotoxicity against human tumor cell lines, HepG2, MCF-7 and SF-268, while no significant effect were found for compounds 1-3.     

Novel indole C-glycosides from Isatis indigotica and their potential cytotoxic activity

Two novel indole C-glycosides, which were the first reported alkaloids C-glycosides from Isatis indigotica, together with five known alkaloids were isolated. The novel alkaloids were elucidated to be indole-3-acetonitrile-4-methoxy-2-C-β-D-glucopyranoside (1) and N-methoxy-indole-3-acetonitrile-2-C-β-D-glucopyranoside (2) on the basis of spectroscopic analysis. 1 exhibited significant cytotoxic activities against human myeloid leukemia HL-60 and human liver cancer HepG2 cells with the IC₅₀ of 1.3 ± 0.1 and 2.1 ± 0.3 μM, respectively. 2 showed potential cytotoxic activities against HL-60 and human myeloid leukemia Mata cells with the IC₅₀ of 5.1 ± 0.4 and 12.1 ± 0.8 μM, respectively.     

Essential oil composition and antioxidant activity of aerial parts of Grindelia robusta from Central Italy

The chemical composition of the essential oil obtained from Grindelia robusta aerial parts from central Italy was analyzed by GC and GC/MS and 45 components were identified. Borneol (15.2%), alpha pinene (10.3%), trans-pinocarveol (7.0%), bornyl acetate (4.5%), limonene (4.3%) were the main components. The antioxidant activity of the essential oil was evaluated using the DPPH and 5-lipoxygenase tests.     

Molluscicidal activity of Solanum species of the Northeast of Brazil on Biomphalaria glabrata

Seven species of Solanum were screened for their molluscicidal properties against Biomphalaria glabrata, the intermediated host of Schistosoma mansoni, Solanum agrarium, S. jabrense, S. melissarum, S. megalonyx, S. paludosum, S. paraibanum and S. stipulaceum. Four extracts showed molluscicidal activity with LC(50) from 22 to 56 microg/ml.     

Chemical composition and antimicrobial activity of essential oil from the rhizomes of Amomum cannicarpum

The essential oil obtained by hydrodistillation of the rhizomes of Amomum cannicarpum was analyzed by GC and GC/MS. Thirty-four compounds were identified, of which the major components were beta-terpineol (13.4%), beta-pinene (9.4%) and alpha-pinene (6.9%). The essential oil showed significant antimicrobial activity.     

Antioxidant flavanes from Livistona chinensis

Three new flavanes and eight known flavonoids were isolated from the fruits of Livistona chinensis. The structure of the new flavanes were established as 2S,3S-3,5,7,3′,5′-pentahydroxyflavane (1), 2R,3R-3,5,6,7,8,4′-hexahydroxyflavane (2) and 2R,3R-3,5,6,7,8,3′,5′-heptahydroxyflavane (3), respectively, on the basis of chemical and spectroscopic data. The antiproliferative activity against four human tumor cell lines (HL-60, Mata, HepG2 and CNE-1) was evaluated. 1 had significantly antiproliferative effects against HL-60 and CNE-1 with the IC₅₀ of 0.2 ± 0.01 and 1.0 ± 0.1 μM, respectively, overpowering the reference compound in the assay (cisplatin). Most compounds also exhibited potent antioxidant activity.     

Iridoid, phenylethanoid and flavonoid glycosides from Sideritis trojana

From the MeOH extract of Sideritis trojana, a new iridoid glycoside, 10-O-(E)-feruloylmelittoside (1) was obtained in addition to four known iridoid glycosides [melittoside (2), 10-O-(E)-p-coumaroylmelittoside (3), stachysosides E (4) and G (5)]. Moreover, five phenylethanoid glycosides [verbascoside (6), isoacteoside (7), lamalboside (8), leonoside A (9), isolavandulifolioside (10), three flavone glycosides (isoscutellarein 7-O-[6'-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (11), 4'-O-methyisoscutellarein 7-O-[6'-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (12), 3'-hydroxy-4'-O-methyisoscutellarein 7-O-[6'-O-acetyl-β-allopyranosyl-(1→2)]-β-glucopyranoside (13) and a benzylalcohol derivative (di-O-methylcrenatin) were obtained and identified. The structures were elucidated on the basis of NMR and HRMS data. All compounds were tested for their antioxidant activity by in vitro TEAC assay and some of them exhibited moderate activity (0.97-1.44 mM) when compared with the reference compound (quercetin 1.86 mM). Glycosides 6-13, the most active compounds in the TEAC assay, were also tested by flow cytometry to evaluate their ability to affect the levels of reactive oxygen species (ROS) in human prostate cancer cells (PC3).     

Two new nortriterpenoid saponins from Salicornia bigelovii Torr. and their cytotoxic activity

Investigation of characteristic constituents of Salicornia bigelovii Torr. led to isolation of two new 30-nortriterpenoid glycosides, Bigelovii A (1), Bigelovii B (2), together with two known 30-nortriterpenoid glycosides 3-4 and three known oleanane-type triterpenoid glycosides 5-7. The structures of new compounds were elucidated by extensive 1D and 2D NMR, and MS spectroscopic analysis, and chemical evidences. All compounds were isolated for the first time from Chenopodiaceae. Thus compounds 1-4 were evaluated for their cytotoxicity and compouds 1, 3 showed moderate activity against four cell lines, HL-60 (promyelocytic leukemia), MCF-7 (breast carcinoma), HepG2 (liver carcinoma) and A549 (lung carcinoma), with IC(50) values of 6.18, 78.08, 13.64 and >100μM for 1; 31.87, >100, ~100, >100μM for 3, respectively.     

New flavane gallates isolated from the leaves of Plicosepalus curviflorus and their hypoglycemic activity

Two new flavane gallates were isolated from the leaves of Plicosepalus curviflorus. The structure of the new compounds was established as 2S,3R-3,3′,4′,5,7-pentahydroxyflavane-5-O-gallate (1) and 2S,3R-3,3′,4′,5,5′,7-hexahydroxyflavane-4′,5-di-O-gallate (2), respectively. In addition, seven known compounds (−)-catechin (3), quercetin (4), lupeol (5), β-sitosterol (6), pomolic acid (7), β-sitosterol 3-O-β-d-glucopyranoside (8) and 4-methoxycinnamic acid (9) were reported for the first time from the genus Plicosepalus. Compounds 1, 2 and 3 were investigated for their hypoglycemic activity and showed significant hypoglycemic activity in Swiss Albino mice.     

Cytotoxic ceramides and glycerides from the roots of Livistona chinensis

A 70% ethanol extract of the roots of Livistona chinensis has been investigated, led to the isolation of 13 compounds, including a new ceramide, (2S,3S,4R,9Z)-2-[(2R)-2-hydroxytricosanoylamino]-9-octadecene-1,3,4-triol (2), a new glycosyl ceramide, 1-O-β-d-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2-hydroxydocosanoylamino]-9-octadecene-1,3,4-triol (3), three new monoacylglycerols, 1-(34-hydroxytetratriacontanoyl)-sn-glycerol (9), 1-[nonadeca-(9Z,12Z)-dienoyl]-sn-glycerol (10), and 1-[12-hydroxypentatriaconta-(13E,15Z)-dienoyl]-sn-glycerol (11), a new diacylglycerol, 1-(heptadeca-6Z,9Z-dienoyl)-3-(octadeca-6Z,9Z,12Z-trienoyl)-sn-glycerol (12), as well as a new diacylglycerol aminoglycoside, 1-octadecanoyl-2-nonadecanoyl-3-O-(6-amino-6-deoxy)-β-d-glucopyranosyl-sn-glycerol (13). The structures of new compounds were elucidated, based on spectroscopic, zymologic and chemical methods. Among the compounds tested, compounds 3, 4 and 13 showed significantly antiproliferative effects against the human tumor cell lines (K562, HL-60, HepG2, and CNE-1) with the IC₅₀ of 10–65 μM. To our knowledge, this is first report of the occurrence of ceramides and acylglycerols in the genus Livistona.     

Polyprenylated isoflavanone and isoflavonoids from Ormosia henryi and their cytotoxicity and anti-oxidation activity

A rare naturally-occurring polyprenylated isoflavanone, designated ormosinol (1), and a new isoflavonoid glycoside, named ormosinoside (2), along with 21 known compounds were isolated from the root bark of Ormosia henryi Prain. The structures of compounds 1 and 2 were determined as 5,7,2′,4′-tetrahydroxyl-6,8,5′-tri-(γ,γ-dimethylallyl)isoflavanone and isoprunetin-7-O-β-d-xylopyranosyl-(1 → 6)-β-d-glucopyranoside on the basis of a combination of 1D-, 2D-NMR and mass spectroscopic measurements. Compound 1 showed significant anti-oxidation activity against DPPH radicals (IC₅₀ 28.5 μM) and cancer cell line (A549, LAC, and HepG2) growth inhibitory activity with IC₅₀ ranging from 4.25 to 7.09 μM, while compound 2 found to be inactive to both testing systems.     

Antimicrobial activity of Diospyros anisandra

Leaves, root and stem bark of Diospyros anisandra were screened against two strains of Mycobacterium tuberculosis, one resistant and one susceptible to antibiotics, using the microplate Alamar blue assay test. The lypophylic fractions of the root and bark showed significant inhibitory activity against both strains, with the hexane fraction of the bark showing the strongest activity (MIC 6.25 microg/ml) against the resistant strain and a significant antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Candida albicans, Aspergillus niger, and Colletotrichum gloeosporioides. The bioassay-guided purification of the bioactive hexane fraction resulted in the isolation and identification of the naphthoquinone plumbagin as one of the metabolites responsible for the biological activity.     

Evaluation of antimicrobial activity of Cleome viscosa and Gmelina asiatica

The ethanolic extracts of the leaves and flowers of Cleome viscosa and roots of Gmelina asiatica were tested for antimicrobial activity. The two plants exhibited a broad spectrum of antimicrobial activity, particularly significative against Escherichia coli , Proteus vulgaris and Pseudomonas aeruginosa. The leaf extract of C. viscosa showed moderate activity against pathogenic fungi.     

Biological activity of Schinus molle on Triatoma infestans

Hexanic extracts from leaves and fruits of Schinus molle were tested for repellent and insecticidal properties against first instar nymphs and eggs of Triatoma infestans, the vector of Chagas' disease. Leaf and fruit extracts were highly repellent for first nymphs. Fruit extracts had also ovicidal activity.     

Antibacterial activity of Abies webbiana

The methanol extract of the dried leaves of Abies webbiana was evaluated for antimicrobial activity. The methanol extract showed a broad spectrum of antibacterial activity.     

Preliminary evaluation of anti-pyretic and anti-ulcerogenic activities of Sida cordifolia methanolic extract

The anti-pyretic and anti-ulcerogenic properties of methanolic extract of Sida cordifolia aerial parts (MESC) were investigated in rats. Oral dose of 500 mg/kg MESC significantly reduced pyrexia induced by TAB vaccine. MESC exhibited significant anti-ulcerogenic effect against aspirin and ethanol induced damage. Both these properties were comparable to the reference drugs.