New sphingolipids from the root of Isatis indigotica and their cytotoxic activity

Two new sphingolipids were isolated from the 95% EtOH extract of traditional Chinese medicinal plant Isatis indigotica. Their structures were elucidated as (2S,3R)-3-hydroxymethyl-N-(2'-hydroxynonacosanoyl)-trideca-9E-sphingenine(1) and 1-O-beta-D-glucopyranosyl-(2S,3R)-3-hydroxymethyl-N-(2'-hydroxynonacosanoyl)-trideca-9E-sphingenine(2) on the basis of spectroscopic data. Their cytotoxic effects were evaluated by using MTT method.     

Sesquiterpene lactones from Centaurea musimomum. Antiplasmodial and cytotoxic activities

The chloroform extract of the aerial parts of Centaurea musimomum exhibited significant activity against Plasmodium falciparum. The phytochemical study of this extract gave seven native and four acetylated sesquiterpene lactones.     

Preliminary antinociceptive, antioxidant and cytotoxic activities of Leucas aspera root

The ethanolic extract of Leucas aspera root was subjected to acetic acid induced writhing inhibition, 1,1-diphenyl-2-picryl hydrazyl (DPPH) free radical scavenging assay and brine shrimp lethality bioassay for screening of antinociceptive, antioxidant and cytotoxic activity, respectively. The extract produced significant writhing inhibition in acetic acid induced writhing in mice at the doses of 250 and 500 mg/kg. The extract showed a significant free radical scavenging activity with an IC(50) of 8 microg/ml. The extract showed significant lethality to brine shrimp with an LC(50) value.     

New nonadjacent bis-THF ring acetogenins from the seeds of Annona squamosa

Two new annonaceous acetogenins named as squamostanin-C and squamostanin-D were isolated from 95% EtOH extract of the seeds of Annona squamosa. Their structures were determined by spectroscopic method, and their cytotoxicities were evaluated by using MTT method.     

Structural features of a new heteropolysaccharide from the fruit bodies of Melia azedarach and its effect on cytotoxic activity

Water-soluble polysaccharides were extracted from the fruit pulps of Melia azedarach and some columns were undertaken to isolate the major polysaccharide (MPS-III). Its structural features were elucidated by IR analysis, carbohydrate analysis, periodate oxidation, Smith degradation, methylation analysis and NMR spectroscopy. Then it was evaluated for the cytotoxic activity in vitro against four human cell lines, using the sulphorhodamine B assay. The data obtained indicated that MPS-III contains a α(1→4) main chain backbone composed of arabinose, mannose in a molar ratio of 1.31:1.0 and has α(1→6) branch structure. And MPS-III showed a strong cytotoxic activity in the BGC-823 cell line.     

Toxic effects of annonaceous acetogenins from <Emphasis Type="Italic">Annona cherimolia</Emphasis> (Magnoliales: Annonaceae) on <Emphasis Type="Italic">Spodoptera frugiperda</Emphasis> (Lepidoptera: Noctuidae)

Plants belonging to the family Annonaceae have been commonly described in traditional medicine as remedies against head lice, and for their insecticidal properties. Characteristic constituents from a few genera of these plants are the annonaceous acetogenins. Fourteen annonaceous acetogenins have been isolated from our Argentine collection of the seeds of A. cherimolia. We report herein the antifeedant and insecticidal effects of nine of those acetogenins on Spodoptera frugiperda (J. E. Smith). The acetogenin squamocin, one of the major constituents of the extract, displayed toxic effects on early larval instars when incorporated to the larval diet at a dose of 50 μg per g of diet. The remaining annonaceous acetogenins tested, itrabin, asimicin, neoanonin, cherimolin-1, cherimolin-2, almuñequin, motrilin, and tucumanin produced pupal mortality and adult malformations leading to death, when incorporated to the larval diet at the same dose. The evaluation of indices of food consumption, growth, and food utilization indicated that squamocin was the only tested acetogenin to produce significant decrease in the growth rate and to reduce the efficiency with which larvae converted ingested food into biomass. All the acetogenins produced more than 80% pupal mortality with no dependence on the position of the THF rings or the number and location of the OH groups.     

Antibacterial and cytotoxic compounds from the bark of Cananga odorata

O-Methylmoschatoline, liriodenine and 3,4-dihydroxybenzoic acid isolated from the barks of Cananga odorata showed antibacterial activities against a number of Gram (+) and Gram (-) bacteria. The compounds also showed antifungal and cytotoxic activities.     

Leishmanicidal activity of Maytenus illicifolia roots

In vitro evaluation of leishmanicidal activity of aqueous and ethanolic extracts of Maytenus illicifolia against three species of Leishmania. The root extracts showed differential activity against parasites, whereas the aerial part of the extracts was inactive.     

A new antiplasmodial coumarin from Toddalia asiatica roots

A new antiplasmodial coumarin, 5,7-dimethoxy-8-(3'-hydroxy-3'methyl-1'-butene)-coumarin (1), has been isolated from the roots of Toddalia asiatica. This finding supports the traditional use of this plant for the treatment of malaria.     

Anti-inflammatory and antinociceptive activities of Trewia polycarpa roots

The alcoholic extract of Trewia polycarpa roots, when administered orally to rats at doses of 50-400 mg/kg, exhibited a dose-dependent anti-inflammatory activity in both acute and chronic models. It also showed a significant antinociceptive action mice in the dose range of 25-200 mg/kg. The extract did not reveal any toxicity in rats up to a dose of 3.2 g/kg (p.o.). It showed the presence of terpenoids, alkaloids, flavonoids, quinones and glycosides on phytochemical screening.     

New cytotoxic quinolone alkaloids from fruits of Evodia rutaecarpa

Three new quinolone alkaloids, 1-methyl-2-[7-hydroxy-(E)-9-tridecenyl]-4(1H)-quinolone (1), 1-methyl-2-[(Z)-4-nonenyl]-4(1H)-quinolone (2), 1-methyl-2-[(1E,5Z)-1,5-undecadienyl]-4(1H)-quinolone (3) and one new natural product, 1-methyl-2-[(E)-1-undecenyl]-4(1H)-quinolone (4), were isolated from the dried and nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth., along with thirteen known compounds (5-17). In addition, one new artificial product, 1-methyl-2-[7-carbonyl-(E)-9-tridecenyl]-4(1H)-quinolone (1A) was also obtained. The structures of these compounds were determined by spectroscopic analyses. The cytotoxic activities of all of the compounds against the human cancer cell lines HL-60, N-87, H-460, and Hep G(2) cells were evaluated by MTT assay. The results showed that these alkaloids inhibited cell proliferation with IC(50) values between 14μM and 22μM.     

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.     

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.     

A new chiratane type triterpenoid from the rhizomes of Drynaria fortunei

Chiratone (1), a rare new chiratane type triterpenoid, together with five known triterpenoids were isolated from the rhizomes of Drynaria fortunei (Kunze) J. Sm. The structure was characterized as 20β-hydroxychiratan-22-one on the basis of extensive 1D and 2D NMR, and MS spectroscopic analyses, and was further confirmed by X-ray crystal diffraction. Primary bioassays showed that compound 1 had significant cytotoxic activity against Hela, PC3 and HepG2 cells, with IC₅₀ of 2.92 μM, 1.08 μM and 2.45 μM, respectively.     

Chemical components of the roots of Noni (Morinda citrifolia) and their cytotoxic effects

Roots of Morinda citrifolia (Noni or Yor in Thai) have been used traditionally for thousands of years to treat chronic diseases such as cancer and heart disease. In this study, three new anthraquinones together with 15 known compounds were isolated from the roots of M. citrifolia (Rubiaceae). Their structures were established by spectroscopic methods, particularly 1D and 2D NMR techniques. Six known compounds, together with two new compounds (2 and 3) showed significant inhibitory effects on the proliferation of human lung and colon cancer cells.     

Two new cytotoxic isomeric indole alkaloids from the roots of Nauclea orientalis

A pair of new isomeric indole alkaloids, naucleaorals A (1) and B (2) were isolated from the roots of Nauclea orientalis. The structures of compounds 1 and 2 were fully characterized using spectroscopic data, and were tested for their cytotoxicity (HeLa and KB cells) and antimalarial activity. Compound 1 showed significant cytotoxicity to HeLa cells with an IC₅₀ value of 4.0 µg/mL, while compound 2 exhibited very modest cytotoxicity to both cell lines with IC₅₀ values of 7.8 and 9.5 µg/mL, respectively. Both compounds proved to be inactive in antimalarial assays (IC₅₀ > 10.00 µg/mL).     

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.     

A new phytosterone from the roots of Achyranthes bidentata

A new phytosterone, (20R, 22R)-2beta, 3beta, 20, 22, 26-pentahydroxy-cholestan-7,12-dien-6-one (1), was isolated from the roots of Achyranthes bidentata. The structure was elucidated on the basis of spectral data.     

Two new triterpenoids from the roots of Actinidia chinensis

Two new triterpenoids (1, 2), together with one flavonoid glycoside and thirteen known triterpenoids were isolated from the roots of Actinidia chinensis Planch (Actinidiaceae). The structures of the new constituents were elucidated as 12α-chloro-2α, 3β, 13β, 23-tetrahydroxyolean-28-oic acid-13-lactone (1), 2α, 3α, 19α, 23, 24-pentahydroxyurs-12-en-28-oic acid (2). Structure elucidation was accomplished by 1D, 2D NMR spectra (HMQC, HMBC, ¹H-¹H COSY, TOCSY, and NOESY) and mass spectrometry (ESIMS). Moreover, two known triterpenoids showed positive cytotoxic activity against LOVO and HepG2 cell lines.     

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.