Quinone reductase (QR) inducers from Andrographis paniculata and identification of molecular target of andrographolide

In the present study, it was demonstrated that the petroleum extract of Andrographis paniculata (AP) had quinone reductase (QR) inducing activity, which might be attributed to the modification of key cysteine residues in Keap1 by Michael addition acceptors (MAAs) in it. To screen MAAs in AP, glutathione (GSH) was employed, and a LC/MS/MS method was implied. Three compounds, andrographoside, andrographolide, 14-deoxy-14,15-dehydroandrographolide were revealed could well conjugated with GSH. Then, andrographolide along with 4 new and 14 known compounds were isolated to conduct QR induction evaluation, and the CD (the concentration required to double the activity of QR) value of andrographolide is 1.43 μM. The QR induce activity of andrographolide might be attributed to its targeting multiple cysteine residues in Keap1, therefore, the alkylation of Keap1 by andrographolide was further studied and the result showed that four cysteine residues: Cys77, Cys151, Cys273 and Cys368 were alkylated, which indicated that Keap1 is a potential target for the QR induce activity of andrographolide.     

Novel prenylated bichalcone and chalcone from Humulus lupulus and their quinone reductase induction activities

A new prenylated chalcone xanthohumol M (1), a novel prenylated bichalcone humulusol (2) and six known chalcones (3–8) were found from Humulus lupulus. Their structures were determined by spectroscopic methods. All the chalcones' electrophilic abilities were assessed by GSH (glutathione) rapid screening, and their QR (quinone reductase) induction activities were evaluated using hepa 1c1c7 cells. The results of electrophilic assay and QR induction activity assay were quite well. New compounds 1 and 2, along with some known prenylated chalcones, displayed certain QR induction activity.     

A new chlorosesquiterpene lactone from Ambrosia maritima

A new chloro-pseudoguaianolide-type sesquiterpene lactone, 11β-hydroxy-13-chloro-11,13-dihydrohymenin (1), was isolated from the Egyptian medicinal plant Ambrosia maritima. The structure was determined by spectroscopic methods, particularly high-resolution ¹H, ¹³C-NMR and 2D ¹H–¹H and ¹H–¹³C COSY NMR analysis.     

New isoflavonolignan with quinone reductase inducing activity from Alhagi pseudalhagi (M.B.)

Bioassay-directed separation of the chloroform extracts from the air-dried aerial part of Alhagi pseudalhagi (M.B.) led to the isolation of a new isoflavonolignan (1), together with five known isoflavones (2–6) (Fig. 1). Their structures were identified on the basis of spectral analysis of NMR, MS, IR, UV and CD spectral evidences. The quinone reductase (QR) inducing activities of the extracts and compound 1 were evaluated and the new isoflavonolignan (1) exhibited moderate quinone reductase (QR) inducing activity for hepa lclc7 cells.     

Phenolic constituents ofTaxus cuspidata I: lignans from the roots

The phenolic constituents of the roots ofTaxus cuspidata (Japanese yew) were investigated. Four lignans, [(+)-taxiresinol (1), (+)-lariciresinol (2), (–)-secoisolariciresinol (3), and (+)-pinoresinol (4)] were isolated and identified. The assignment of proton and carbon atoms for the lignans were finally solved by one- and twodimensional-nuclear magnetic resonance spectra. The enantiomeric excess of these lignans were determined by chiral high-performance liquid Chromatographic analyses. (+)-Lariciresinol and (–)-secoisolariciresinol were optically pure; (+)-taxiresinol was also suggested to be optically pure, although (+)-pinoresinol was not (77% enantiomeric excess).     

Effects of Pithecellobium clypearia Benth extract and its main components on inflammation and allergy

The ethanol extract of Pithecellobium clypearia Benth (PCE) was characterized to be rich in polyphenols by HPLC analysis, and investigated for its anti-inflammatory and anti-allergic activities. In our assay, PCE showed anti-inflammatory activity in both acute and auto-immune inflammation animal models. Administration of PCE can effectively inhibit the croton oil-induced ear edema and capillary permeability, the carrageenin-induced paw edema, and the liver injury caused by propionibacterium acnes plus lipopolysaccharide. PCE was also found to possess anti-allergic activity in inhibiting the DNFB-induced delayed hypersensitivity reaction. Meanwhile, seven main components (1–7) from PCE were studied for their effect on histamine release stimulated by compound 48/80 from rat peritoneal mast cells in vitro. Compound 2 ((−)-epigallocatechin-7-gallate), 3 ((−)-5, 7, 3′, 4′, 5′-pentahydroxyflavan), and 5 ((−)-tetra hydroxyflavan-7-gallate) showed significant inhibition effect on histamine release.     

In vivo hypoglycemic effects of phenolics from the root bark of Morus alba

Moracin M (1), Steppogenin-4′-O-β-D-glucosiade (2), Mullberroside A (3) were isolated from the root bark of Morus alba L. and identified by spectral evidence. Compounds 1, 2 and 3 were studied in hypoglycemic effects on alloxan-diabetic mice. The results showed that compounds 1, 2 and 3 all produced hypoglycemic effects. The compound 2 in a dose of 50 mg/kg exerted significant effect (p < 0.05), 2 and 3 in a dose of 100 mg/kg exerted obviously effect (p < 0.01). Meantime, the compound 1 in a dose of 100 mg/kg can make the fasting blood glucose level have decreasing tendency.     

Enantiomeric compositions and biosynthesis ofWikstroemia sikokiana lignans

Thymelaeaceae plants produce dextrorotatory dibenzylbutyrolactone lignans, which are opposite enantiomers to the lignans isolated from other plants (e.g.,Forsythia spp.). In our previous paper, (–)-pinoresinol (74% enantiomer excess), (+)-matairesinol (optically pure), and (+)-wikstromol (optically pure) were isolated fromWikstroemia sikokiana (Thymelaeaceae). In the present investigation, a survey of lignans and the determination of their enantiomeric compositions were continued. Four lignans, (–)-lariciresinol, (–)-secoisolariciresinol, (+)-kusunokinin, and (+)-methyltrachelogenin, were isolated from MeOH extracts ofW. sikokiana stem. To our knowledge, we have isolated (+)-methyltrachelogenin from plants for the first time. Chiral high-performance liquid chromatographic analysis showed that (+)-kusunokinin and (+)-methyltrachelogenin were optically pure, whereas (–)-lariciresinol and (–)-secoisolariciresinol were not (39% and 45% enantiomer excess, respectively). Feeding experiments with deuterium-labeled substrates demonstrated conversion of coniferyl alcohol to the lignans and interconversion of lignans. These reaction sequences are similar to the sequence catalyzed byForsythia enzymes. However, predominant enantiomers of the lignans, except for secoisolariciresinol isolated fromW. sikokiana, have absolute configurations opposite to those of the corresponding lignans isolated fromForsythia spp. Based on the results of the isolation and the feeding experiments, several differences betweenW. sikokiana andForsythia spp. are pointed out regarding stereochemical mechanisms for lignan biosynthesis.Parts of this report were presented at the 46th annual meeting of the Japan Wood Research Society, Kumamoto, April 1996; and the 47th annual meeting of the Japan Wood Research Society, Kochi, April 1997     

Modelling agroforestry systems of cacao (Theobroma cacao) with laurel (Cordia alliodora) and poro (Erythrina poeppigiana) in Costa Rica II. Cacao and wood production,litter production and decomposition

During 7 years (1979–1985) cacao harvests (beans and husks) have been recorded for the agroforestry systems ofTheobroma cacao underCordia alliodora andErythrina poeppigiana shade trees. The mean oven dry cacao yields were 626 and 712 kg.ha^–1.a^–1 cocoa beans underC. alliodora andE. poeppigiana respectively. Harvests have gradually increased over the years and the plantation has now reached maturity.Annual extraction of N, P, K, Ca and Mg in fruits, which is relatively small, was calculated on the basis of chemical analyses. The following average values were found (kg.ha^–1.a^–1): At the age of 8 years, theC. alliodora trees have reached 26.7 cm diameter (DBH) and 14.0 m in height. Mean annual growth (from age 5 to 7) is 14.6 m³.ha^–1.a^–1.Natural plant residue production has been measured for 4 years (Nov. 1981–Oct. 1985). UnderE. poeppigiana it has reached a value of 8.91 t.ha^–1.a^–1 and underC. alliodora 7.07 t.ha^–1.a^–1. The shade trees have contributed 57 and 47% respectively. Transference and decomposition rates are high and important in the nutrient cycles.The nutrient content of the litter was analysed and corresponding average yearly transfers were (kg.ha^–1.a^–1): For part I see Vol. 4, No. 3, 1986.Agroforestry Project, CATIE/GTZ (Tropical Agricultural Research and Training Center/Gesselschaft für Technische Zusammenarbeit), Turrialba, Costa Rica     

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.     

Modelling agroforestry systems of cacao (Theobroma cacao) with laurel (Cordia alliodora) or poro (Erythrina poeppigiana) in Costa Rica

Predictive models were developed for Cordia alliodora branch and Theobroma cacao branch or leaf biomass,based on branch basal areas (r² 0.79) but the model of C. alliodora leaf biomass, although significant, was of very low accuracy (r² = 0.09) due to annual leaf fall. At age 10 years, shade tree stem biomass accounted for 80% of the total above-ground biomass of either tree. However, between the ages of 6 and 10 years, the biomass increment of T. cacao branches (3–4t.ha^–1.a^–1) was similar to that of the shade tree stems. During the same period, the net primary productivity was 35 and 28 t.ha^–1.a^–1, for the Erythrina poepigiana and and C. alliodora systems, respectively.Cocoa production under either of the shade trees C. alliodora or E. poeppigiana was 1000 kg.ha^–1.a^–1 (oven-dry; ages 6–10 yr). During the same period, C. alliodora timber production was 9 m³.ha^–1.a^–1 whilst the leguminous shade tree E. poeppigiana does not produce timber. Litterfall over the same 5 years, including crop and/or shade tree pruning residues, averages 11 and 23 t.ha^–1.a^–1, respectively. The main difference was due to E. poeppigiana pruning residues (10t.ha^–1.a^–1).Soil organic material reserves (0–45 cm) increased over 10 years from 198 to 240 t.ha^–1 in the E. poeppigiana plots and from 168–184 t.ha^–1 in the C. alliodora plots. These values, together with the productivity indices presented, provide evidence that the systems are sustainable.For economic reasons, the use of C. alliodora is recommended under the experimental conditions. however, on less fertile soils without fertilization, the greater biomass and hence nutrient return to the soil surface under E. poeppigiana, might make this the preferable shade tree.     

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.     

New steroids from Clerodendrum colebrookianum

Five new steroids, colebrin A–E (1–5) were isolated from the aerial parts of Clerodendrum colebrookianum. The structures of the new compounds were elucidated on the basis of spectral evidence.     

Anti-inflammatory and anti-osteoporotic lignans from Vitex negundo seeds

Chemical investigation of Vitex negundo seeds afforded four new lignans, including a phenylindene-type lignan, vitexdoin F (1), and three phenylnaphthalene-type lignans, vitexdoins G, H and I (2–4). Their structures were elucidated by detailed spectroscopic analyses on the basis of NMR, IR, and MS data. All compounds were evaluated for their anti-inflammatory and anti-osteoporotic activities, employing RAW264.7 macrophages, osteoblast-like UMR106 and osteoclastic cells, respectively. Compound 1 showed significant inhibition on the nitric oxide (NO) production (IC₅₀ 4.17 μg/mL) due to its down-regulation of the inducible nitric oxide synthase (iNOS) protein expression in LPS-stimulated RAW264.7 cells, which also exhibited potent stimulatory effects on the proliferation and ALP (alkaline phosphatase) activity of UMR106 cells, and significantly up-regulated the OPG/RANKL protein ratio.     

Five new alkaloids from Coptidis Rhizoma–Euodiae Fructus couple and their cytotoxic activities against gastrointestinal cancer cells

A new indoloquinazoline alkaloid, 10-methoxywuchuyuamide I (1), three new benzylisoquinoline alkaloids, named as coptichic aldehyde (2), coptichine (3) and 13-carboxaldehyde-8-oxocoptisine (4), and a new isoindoline alkaloid, named as coptichinamide (5), together with two known alkaloids, wuchuyuamide I (6) and 8-oxocoptisine (7) were isolated from the Coptidis Rhizoma–Euodiae Fructus couple. Their chemical structures were determined by extensive spectroscopic analyses, including IR, UV, EI–MS, HRESI–MS, 1D and 2D NMR data (¹H NMR, ¹³C NMR, ¹H–¹H COSY, HSQC and HMBC). Cytotoxicities of the isolated alkaloids against NCI-N87 and Caco-2 cell lines were evaluated. Four benzylisoquinoline alkaloids 2–4 and 7 showed inhibitory activities against NCI-N87 cell with IC₅₀ values range from 8.92 to 35.98 μM. The alkaloid 3 was a new antiproliferation compound against NCI-N87 cells. The results provided valuable information for further investigation of alkaloid 3 as a chemopreventive agent.     

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.     

New lignans from the bioactive fraction of Sambucus williamsii Hance and proliferation activities on osteoblastic-like UMR106 cells

Four new lignans (1, 7–9), together with nine known ones, were isolated from the anti-osteoporosis fraction of the extract of Sambucus williamsii Hance which was eluted by 50% and 95% aqueous ethanol over D101 macroporous resin column. Their structures were elucidated by NMR spectroscopic analyses, and the absolute configurations of all compounds were determined by application of circular dichroism method. All the compounds were reported for the first time from the Sambucus genus and firstly studied for their proliferation effects on osteoblastic-like UMR 106 cell. The data showed that compounds 2–9 significantly promoted cell proliferation in some dose, especially compounds 2, 3, 4, 5, and 7 increased osteoblastic cell numbers by 31.3%, 28.3%, 25.6%, 25.1% and 26.0% at 10^− 10 M, 10^− 10 M, 10^− 7 M, 10^− 10 M and 10^− 10 M, respectively, which suggested that lignans were the components accounting for the bone protective effects of SWH.     

Fodder production responses to pruning height and fodder quality of some trees and shrubs in a forest-savanna transition zone in southwestern Nigeria

Seasonal fodder production responses of five shrubs (Centrosema arenarium, Desmodium strigillosum, Desmodium velutinum, Phyllodium pulchellum, and Tadehagi triquetrum)and five trees (Albizia gummifera, Berlinia grandiflora, Albizia niopoides, Bauhinia monandra, and Inga edulis) to pruning heights ranging from 15 to 75 cm were evaluated during the main-wet, minor-wet, and dry seasons of 1993 and 1994 in the forest-savanna transition zone of West Africa. Fodder from the main-wet season was analysed for nitrogen (N) and phosphorus (P), and dry matter degradation characteristics after 6, 12, 24, 48, 72 and 96 h of incubation in rumen-fistulated N'Dama steers. In the minor-wet season, fodder production of all species increased in response to increasing pruning height with the exception of P. pulchellum and A. gummifera. Highest fodder production was attained at a pruning height of 45 cm for the Desmodium species, 50 cm for P. pulchellum, and 75 cm for the rest of the species. Concentrations of N and P varied significantly among the species; for N the ranges were 28.7–38.8 g kg^–1 (shrubs) and 25.3–44.5 g kg^–1 (trees), while for P the ranges were 3.26–7.04 g mg^–1 (shrubs) and 3.58–6.76 g mg^–1 (trees). Dry matter degradation characteristics differed significantly among shrubs and trees; ranges for shrubs were: soluble fraction (a), 128–185; degradable fraction (b), 664–703; potential degradability (PD), 793–857, as g kg^–1; rate of degradation (c), 0.0241–0.0308 as % h^–1 while for trees ranges were: (a), 139–160; (b), 651–826; (PD), 824–970, as g kg^–1; (c), 0.0143–0.0227 as % h^–1. Based on fodder production and quality, C. arenarium, D. strigillosum, D. velutinum, B. monandra, I. edulis, and A. niopoides were the most promising species for the development of animal agroforestry technologies in the west African forest-savanna transition zone and similar environments in the tropics.This revised version was published online in November 2005 with corrections to the Cover Date.     

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).     

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.