Cytotoxicity of withanolides isolated from Acnistus arborescens

A new withanolide identified by spectroscopic analysis as 12β-acetoxy-4-deoxy-5,6-deoxy-Δ⁵–withanolide D and Withanolide D, were isolated from the leaves of Acnistus arborescens. Cytotoxic activity of these two compounds against human tumor cell lines HT-29, MCF-7, MKN-45, HEp-2, HeLa, U-937 and two human normal fibroblast cultures, Fib04 and Fib05, were assessed. Withanolide D presented in vitro cytotoxic activity against tumor cell lines at the low micromolar range (LC₅₀:1.0 to 1.69 µM) and showed a slightly lower activity against Fib04, suggesting moderated selectivity among tumoral and normal cells. No cytotoxic effect was observed for 12β-acetoxy-4-deoxy-5,6-deoxy-Δ⁵–withanolide D.     

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.     

Cyclisation of farnesyl pyrophosphate into sesquiterpenoids in ginger rhizomes (Zingiber officinale)

The atomic ratios (¹⁴C/³H) obtained in ar-curcumene, α-zingiberene, β-bisabolene obtained from the essential oil of rhizomes of Zingiber officinale which were fed with [2-¹⁴C, 2-³H₂], [2-¹⁴C, 4R-³H₁] and [2-¹⁴C, 5-³H₂]mevalonic acid and [1-³H₂]farnesylpyrophosphate (FPP) revealed that (a) (2E,6E)-isomer of FPP is isomerised to (2Z,6E)-isomer without loss of epimeric hydrogen that means without a redox process; (b) (2Z,6E)-FPP is cyclised to bisabolyl cation which is the penultimate precursor of α-zingiberene, ar-curcumene and β-bisabolene; and (c) two 1,2-hydrogen shifts take place during the formation of α-zingiberene whereas one 1,2 shift has been observed during the formation of ar-curcumene.     

An anti-inflammatory and immunomodulatory polysaccharide from Orbignya phalerata

A polysaccharide, a glucan with mean M_r of 1.0×10⁶ (MP1), was isolated from the mesocarp of fruits of Orbignya phalerata. Chemical and spectroscopic studies indicated that MP1 has a highly branched glucan type structure composed of α-(1→4) linked -glucopyranose residues with (3→4), (4→6), and with (3→6) branching points. MP1 enhanced phagocytosis in vivo and exhibited anti-inflammatory activity.     

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.     

Essential oil from the leaves of Cryptomeria japonica acts as a silverfish (Lepisma saccharina) repellent and insecticide

This is the first article to report the evaluation of a natural product used as an antisilverfish agent. Silverfish (Lepisma saccharina), primitive wingless insects, feed on a variety of materials, including paper, cotton, starch, and cereals. They can be a problem in libraries and other places where books, documents, and papers are stored. In this pilot study, the essential oil from leaves of Cryptomeria japonica was investigated to test its properties as a silverfish repellent and insecticide. The results from a repellency bioassay show that the essential oil significantly repelled silverfish. The repellent activity was 80% at a dosage of 0.01 mg/cm³. When silverfish were exposed to a concentration of 0.16 mg/cm³ of essential oil, they were killed within 10h. The chemical composition of essential oil, the emissions from a test chamber, and the residue left on filter papers previously soaked with the essential oil in a chamber were analyzed by gas chromatography-mass spectrometry. The components of the essential oil were found to be: elemol (18.22%), 16-kaurene (11.63%), 3-carene (9.66%), sabinene (9.37%), 4-terpineol (9.06%), β-eudesmol (5.70%), α-pinene (5.62%), and limonene (5.26%). Only some constituents of the essential oil compounds collected by solid-phase microextraction were found to be emitted in the test chamber. The main constituents were: 3-carene (21.03%), p-cymene (10.95%), limonene (9.49%), β-myrcene (9.39%), γ-terpinene (9.10%), α-terpinene (8.57%), and 4-terpineol (7.97%).     

A new flavonoid from the aerial part of Thalictrum atriplex

A new flavone glycoside, identified as kaempferol 3-O-[3′″-acetyl-α- -arabinopyranosyl-(1′″–6″)]-β- -glucopyranoside (1), has been isolated from the aerial part of Thalictrum atriplex.     

Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L.

From the ethyl acetate soluble fraction of an acetone–water extract of the aerial parts of Rumex acetosa L. (Polygonaceae), a variety of monomeric flavan-3-ols (catechin, epicatechin, epicatechin-3-O-gallate), A- and B-type procyanidins and propelargonidins (15 dimers, 7 trimers, 2 tetramers) were isolated with 5 so far unknown natural products. Dimers: procyanidin B1, B2, B3, B4, B5, B7, A2, epiafzelechin-(4β→8)-epicatechin, epiafzelechin-(4β→8)-epicatechin-3-O-gallate (new natural product), epiafzelechin-(4β→6)-epicatechin-3-O-gallate (new natural product), epiafzelechin-3-O-gallate-(4β→8)-epicatechin-3-O-gallate, B2-3′-O-gallate, B2-3,3′-di-O-gallate, B5-3′-O-gallate, and B5-3,3′-di-O-gallate. Trimers: procyanidin C1, epiafzelechin-(4β→8)-epicatechin-(4β→8)-epicatechin (new natural product), epicatechin-(4β→8)-epicatechin-(4β→8)-catechin, cinnamtannin B1, cinnamtannin B1-3-O-gallate (new natural product), tentatively epicatechin-(2β→7, 4β→8)-epiafzelechin-(4α→8)-epicatechin (new natural product), and epicatechin-3-O-gallate-(4β→8)-epicatechin-3-O-gallate-(4β→8)-epicatechin-3-O-gallate.Tetramers: procyanidin D1 and parameritannin A1. All compounds were elucidated by ESI-MS, CD spectra, 1D- and 2D-NMR experiments as free phenols or peracetylated derivatives and, in part, after partial acid-catalysed degradation with phloroglucinol.A more abundant proanthocyanidin polymer was also isolated, purified and its chemical composition studied by ¹³C NMR.In addition a so far unknown phloroglucinolglycoside (1-O-β-d-(2,4-dihydroxy-6-methoxyphenyl)-6-O-(4-hydroxy-3,5-dimethoxybenzoyl)-glucopyranoside) was isolated.     

Cycloartane saponins from Astragalus peregrinus as modulators of lymphocyte proliferation

From Astragalus peregrinus, four cycloartane-type saponins have been isolated and their structures elucidated by spectral means as 20(R),24(S)-epoxy-9β,19-cyclolanostane-3β,6α,16β,25-tetrol 3-O-β- -glucopyranoside (1), 20(R),24(S)-epoxy-9β,19-cyclolanostane-3β,6α,16β,25-tetrol 3-O-α- -rhamnopyranosyl-(1→4)-β- -glucopyranoside (2), 20(R),24(S)-epoxy-9β,19-cyclolanostane-3β,6α,16β,25-tetrol 3-O-α- -rhamnopyranosyl-(1→2)-β- -glucopyranoside (3) and 20(R),25-epoxy-9β,19-cyclolanostane-3β,6α,16β,24(S)-tetrol (24-O-acetyl)- 3-O-α- -rhamnopyranosyl-(1→2)-(6′-O-acetyl)-β- -glucopyranoside (4). Compounds 2 and 3 showed to stimulate the proliferation of mouse splenocytes and were not significantly cytotoxic.     

Antimicrobial ent-pimarane diterpenes from Viguiera arenaria against Gram-positive bacteria

The dichloromethane crude extract from the roots of Viguiera arenaria (VaDRE) has been employed in an antimicrobial screening against several bacteria responsible for human pathologies. The main diterpenes isolated from this extract, as well as two semi-synthetic pimarane derivatives, were also investigated for the pathogens that were significantly inhibited by the extract (MIC values lower than 100 μg mL^− 1). The VaDRE extract was significantly active only against Gram-positive microorganisms. The compounds ent-pimara-8(14),15-dien-19-oic acid (PA); PA sodium salt; ent-8(14),15-pimaradien-3β-ol; ent-15-pimarene-8β,19-diol; and ent-8(14),15-pimaradien-3β-acetoxy displayed the highest antibacterial activities (MIC values lower than 10 μg mL^− 1 for most pathogens). In conclusion, our results suggest that pimaranes are an important class of natural products for further investigations in the search of new antibacterial agents.     

Two new furostanol saponins from Tribulus terrestris L.

Two new furostanol glycosides, named tribufurosides I (1) J (2), were isolated from the fruits of Tribulus terrestris L. by a combination of chemical and spectroscopic methods. Its structures were established as 26-O-β-d-glucopyranosyl-(25S)-5α-furost-12-one-2α,3β,22α,26-tetraol-3-O-β-d-glucopyranosyl (1 → 2)-β-d-glucopyranosyl (1 → 4)-β-d-galactopyranoside (1) and 26-O-β-d-glucopyranosyl-(25R)-5α-furost-20(22)-en-12-one-2α,3β,26-triol-3-O-β-d-glucopyranosyl (1 → 4)-β-d-galactopyranoside (2).     

Antifeedant activity of vicolides from Pentanema indicum

Vicolides A–D (0.2–2000 ppm) from Pentanema indicum showed antifeedant activity against Euproctes fraterna and Pericallia ricini V stage larvae.     

Insecticidal effects of the powdery formulation based on clay and essential oil from the leaves of <Emphasis Type="Italic">Clausena anisata</Emphasis> (Willd.) J. D. Hook ex. Benth. (Rutaceae) against <Emphasis Type="Italic">Acanthoscelides obtectus</Emphasis> (Say) (Coleoptera: Bruchidae)

The bioefficacies of essential oil and aromatized clay powder based on the mixture of clay and essential oil extracted from Clausena anisata were evaluated for their insecticidal activities and their effects on progeny production of Acanthoscelides obtectus. Contact toxicity assayed by coating on bean grains showed that these chemicals caused significant mortality of the test insect. Beetle mortality was dose dependant and after 2-day exposure the aromatized clay powder was more toxic (LD₅₀ = 0.069 μl/g grain) than the pure essential oil (LD₅₀ = 0.081 μl/g grain). There was, however, a highly significant loss of toxicity after 24 and 36 h following treatment with essential oil and aromatized powder, respectively. Both aromatized clay powder and pure essential oil considerably reduced the F₁ progeny insect production. The essential oil evoked moderated repellent action and high fumigant toxicity (LC₅₀ = 0.093 μl/cm³) against adults of A. obtectus. These results suggest that the clay powder could be used to stabilize the essential oil to increase its efficacy for use as an alternative to synthetic insecticides.     

Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma

Phytochemical investigation of the stem bark of Terminalia mollis afforded friedelin (1), catechin with epicatechin (2), gallocatechin with epigallocatechin (3) and 3-O-methylellagic acid 4'-O-α-rhamnopyranoside (4). Arjunolic acid with 2α, 3β, 23-trihydroxy-urs-12-en-28-oic acid (5), 2α-hydroxyursolic acid (6), gallic acid (7), chebulanin (8) and 2'-O-galloylvitexin (9) were isolated from the leaf. Chebulanin (8), betulinic acid (10), ursolic acid (11), catechin (12), isoorientin (13), orientin (14), isovitexin (15) and punicalagin (16) were isolated from Terminalia brachystemma leaf. The first full unambiguous NMR assignments for (4) and (8), and revised assignments for (9), are reported. Compound (16) showed good activity against three Candida species.     

The optimum temperature–humidity combination for the feeding activities of Japanese subterranean termites

Two species of Japanese subterranean termite, Coptotermes formosanus Shiraki and Reticulitermes speratus (Kolbe), were used in an investigation of the optimum temperature–relative humidity (RH) combination for their feeding activities. Daily wood consumption per worker and survivals were measured, and the protozoan fauna in the hindgut were observed under 15 temperature–RH combinations for 1 week. Five temperatures (20°, 25°, 30°, 35°, and 40°C) and three RH conditions (50%, 70%, and 90% RH) were examined. The activities of the workers were highest at around 30°C for both species, and workers died at 40°C within 5 days and 2 days for C. formosanus and R. speratus, respectively. The optimum RH condition for feeding activity was 90% RH for C. formosanus and 70%–90% RH for R. speratus. The optimum temperature–RH combinations for feeding activities were 30°C at 90% RH for C. formosanus and 30°C at 70%–90% RH for R. speratus.     

Fine root dynamics of shaded cacao plantations in Costa Rica

Root turnover may contribute a significant proportion of recycled nutrients in agroforestry systems and competition between trees and crops for nutrients and water may depend on temporal fine root regrowth patterns. Fine root biomass ( 2 mm) and fine root productivity were measured during one year in plantations of cacao (Theobroma cacao) shaded by Erythrina poeppigiana or Cordia alliodora planted on a deep alluvial soil in Turrialba, Costa Rica. Fine root biomass of approximately 1.0 Mg ha^–1 varied little during the year with maximum values at the beginning of the rainy season of 1.85 Mg ha^–1 in the cacao-C. alliodora system compared to 1.20 Mg ha^–1 for cacao-E. poeppigiana. Fine root productivity of C. alliodora and E. poeppigiana (maximum of 205 and 120 kg ha^–1 4 week^–1, respectively) was greatest at the end of the rainy season, while for cacao it was greatest at the beginning of the rainy season (34–68 kg ha^–1 4 week^–1), which suggests that if nutrient competition occurs between the shade trees and the cacao, it could be minimized by early fertilization during the beginning of the rains immediately after pruning the shade trees. Annual fine root turnover was close to 1.0 in both systems. Assuming that fine root biomass in these mature plantations was constant on an annual basis, nutrient inputs from fine root turnover were estimated as 23–24 (N), 2 (P), 14–16 (K), 7–11 (Ca) and 3–10 (Mg) kg ha^–1 year^–1, representing 6–13% and 3–6% of total nutrient input in organic matter in the C. alliodora and E. poeppigiana systems, respectively.     

Fumigant toxicity of Carum copticum and Vitex pseudo-negundo essential oils against eggs, larvae and adults of Callosobruchus maculatus

Fumigant activity of essential oil vapors distilled from Carum copticum C. B. Clarke and Vitex pseudo-negundo Hand I. MZT. was tested against eggs, larvae and adults of Callosobruchus maculatus (F.). Fumigant toxicity was assessed at 27 ± 1°C and 60 ± 5% RH, in dark condition. The influence of different concentrations of the essential oil vapors on egg hatchability, larval and adult mortality was significant. Data probit analysis showed that lethal concentration of the essential oil to kill 50% of the population (LC₅₀) for egg, larvae and adult were found to be 1.01, 2.50 and 0.90 μl/l air of C. copticum oil, followed by 2.20, 8.42 and 9.39 μl/l air essential oil of V. pseudo-negundo, respectively. Between these essential oils, C. copticum was almost more toxic than V. pseudo-negundo on all growth stages of C. maculatus. The present study suggests that essential oils from these medicinal plants may be potential grain protectants as botanical alternative fumigants and could be used in the management of various life stages of C. maculatus.     

Crop yields of rice and wheat grown in rotation as intercrops with three tree species in the outer hills of Western Himalaya

Studies on tree crop interaction under rainfed condition in Dehradun valley were conducted for 13 years during 1977 to 1990. Grewia optiva (Bhimal), Morus alba (Mulbery) and Eucalyptus hybrid were tried along with rice (CV: Akashi) — wheat (CV: RR-21) rotation. One-year-old tree seedlings of the above tree species were planted in line, 5 m apart in N-S direction, in July 1977, in the middle of the plot (size 20 m × 20 m). Eucalyptus was first harvested in 1987. Grewia optiva, Morus alba and coppice of Eucalyptus were harvested in 1990. All tree species had depressing effect on crop yields. Eucalyptus had maximum effect in depressing crop yield till the first harvest and had least effect thereafter. From 1987 onwards, Morus alba affected rice most, while wheat was mostly affected by Grewia optiva. The depressing effect on an average varied from 28 to 34% depending upon the species.Distance of tree line from the crop significantly affected the crop yield upto a distance of 5 m and there was 39% decrease in crop yield upto 1 m, 33% from 1–2 m, 25% from 2–3 m and 12% from 3–5 m distance. Annual removal of lops and tops from trees partly compensated the deficit. Grewia optiva could produce 1.08 t ha^–1 yr^–1 of branches and 0.26 t ha^–1 yr^–1 of leaves (air dry) and 1.28 t ha^–1 yr^–1 of branches and 0.28 t ha^–1 yr^–1 of leaves were obtained from Morus alba. Wood (ADT) produced by the trees was 33.6 t ha^–1 from Eucalyptus, 9.5 t ha^–1 from Grewia optiva and 11.6 t ha^–1 from Morus alba.     

A new cytotoxic casbane diterpene from Euphorbia pekinensis

A new cytotoxic casbane diterpene, named pekinenal, was isolated from the roots of Euphorbia pekinensis. Its structure was elucidated as 5α-hydroxy-1βH,2αH-casba-3Z,7E,11E-triene-18-al by a combination of 1D- and 2D-NMR techniques and confirmed by X-ray crystallography. Pekinenal showed cytotoxic activity against all four human cancer cell lines tested.     

Antihyperlipidemic effect of Casearia sylvestris methanolic extract

Casearia sylvestris methanolic extract (MCE) was screened at doses of 125–500 mg/kg for its antihyperlipidemic activity. The antihyperlipidemic effect was evaluated in olive oil-loaded mice. Acute treatment caused inhibition in the triglyceride (TG) and serum lipase elevation-induced by 5 ml/kg of olive oil.