Datura metel: in vitro production of tropane alkaloids

Hairy root lines of Datura metel were established following infection of aseptic stem segments with Agrobacterium rhizogenes strain A4 and cultured in hormone-free B5 solid medium. The growth and production of hyoscyamine and scopolamine (mg/g dry wt.) of these root cultures was encouraged by using B5 liquid medium with half-strength salts. In these culture conditions, the capacity of the highest productive root line 25 to excrete scopolamine into the culture medium rose from 8.7% to 70% when the permeabilizing agent Tween 20 was added for 24 h to the medium, after 2 and 4 weeks of culture. Using an airlift bioreactor (41) with modifications in order to increase root anchorage, the Tween 20 treatment encouraged both growth and alkaloid productivity of cultured root line 25. After 4 weeks their biomass yield was 2.3 mg/l/day and 0.84 mg/l/day of scopolamine was produced (70% extracellular). The scopolamine released into the culture medium was separated with an Amberlite XAD-2 column located in the media exit.     

A novel analgesic pyrazine derivative from the leaves of Croton tiglium L

A novel analgesic pyrazine derivative, named crotonine, was isolated from the leaves of Croton tiglium L. The structure was elucidated as 2-(furan-2-yl)-5-(2,3,4-trihydroxy-butyl)-1,4-diazine by spectroscopic analysis. Crotonine inhibited remarkably the acetic acid-induced writhing in mice.     

A novel analgesic pyrazine derivative from the leaves of Croton tiglium L.

A novel analgesic pyrazine derivative, named crotonine, was isolated from the leaves of Croton tiglium L. The structure was elucidated as 2-(furan-2-yl)-5-(2,3,4-trihydroxy-butyl)-1,4-diazine by spectroscopic analysis. Crotonine inhibited remarkably the acetic acid-induced writhing in mice.     

A novel analgesic pyrazine derivative from the leaves of Croton tiglium L.

A novel analgesic pyrazine derivative, named crotonine, was isolated from the leaves of Croton tiglium L. The structure was elucidated as 2-(furan-2-yl)-5-(2,3,4-trihydroxy-butyl)-1,4-diazine by spectroscopic analysis. Crotonine inhibited remarkably the acetic acid-induced writhing in mice.     

Pharmacognostic Studies on Datura metel Linnaeus the Anatomy of the Leaf

Abstract

Histologically Datura metel L. is readily distinguished from other cogeneric drug species by its smooth cuticle, basal width of covering trichome (measuring up to 34 μ), presence of stomata on both upper and lower leaf epidermides, non-warty stalk of glandular trichomes, collapsed stomata on leaf epidermis. Figures of quantitative microscopy are reported. Histological characters used to complement morphological ones enable one to identify drug in entire or powdered form.     

Toxicity studies on Datura metel L. with reference to official stramonium

Suspensions of the powdered leaf of Datura metel L. and Datura stramonium L. (Solanaceae) were administered by intubation at different doses: 0.125 mg/kg, 0.250 mg/kg, 0.500 mg/kg, 1.000 mg/kg, 1.224 mg/kg and 1.400 mg/kg to virgin female albino mice and were observed daily. After two weeks, the mice were sacrificed and the liver, kidney and intestine were removed, preserved in 10% formalin solution and embedded in paraffin wax. Tissues from these organs were stained for assessment of tissue morphology. Pathological changes observed at 1.224 mg/kg and 1.400 mg/kg (LD100) were irreversible. At all other dose levels, there were reversible changes in the liver, kidney and intestine. Generally, D. metel-treated mice showed less anatomical abnormalities than D. stramonium-treated mice. Hence, D. metel could serve as a substitute for D. stramonium in drug development.     

A new flavone derivative from Ehretia ovalifolia leaves

From the methylene chloride extract of Ehretia ovalifolia leaves, a new flavone derivative named ovalifolin [3-(3-methyl-1-butenyl)-6-methoxy-5,7,4'-trihydroxy flavone] has been isolated and identified together with the known flavone aglycones apigenin, luteolin and the highly methoxylated flavanol araneosol. The structures of these metabolites have been established on the basis of chemical, chromatographic and spectral methods.     

Variation of scopolamine and atropine in different parts of Datura metel during development

Scopolamine and atropine contents in the whole plant of Datura metel L. increased gradually with the progress of developmental growth, and were most pronounced when the plant was at the end of its reproductive stage. The highest percentage of scopolamine accumulation in the root was after 16 weeks. The root was the organ which often accumulated higher amounts of atropine. The aerial parts, if compared with the root of the plant, usually accumulated relatively higher amounts of scopolamine and relatively lower amounts of atropine.     

Piperazine propanol derivative as a novel antifungal targeting 1,3-beta-D-glucan synthase

1,3-beta-D-Glucan synthase, which synthesizes a main component of fungal cell wall, is one of the promising targets for antifungal agents. In order to identify novel chemical classes of 1,3-beta-D-glucan synthase inhibitors, we screened a chemical library monitoring inhibition of the Candida albicans 1,3-beta-D-glucan synthase activity. The piperazine propanol derivative GSI578 [(2,6-difluoro-phenyl)-carbamic acid 3-(4-benzothiazol-2-yl-piperazine-1-yl)-propyl ester] was identified as a potent inhibitor against 1,3-beta-D-glucan synthase with an IC50 value of 0.16 microM. GSI578 exhibited in vitro antifungal activity against pathogenic fungi including C. albicans and Aspergillus fumigatus. Temperature-sensitive mutations of the FKS1 gene in the Deltafks2 background of Saccharomyces cerevisiae, where FKS1 and FKS2 encode putative catalytic subunits of 1,3-beta-D-glucan synthase, altered sensitivity to GSI578. This suggests that the antifungal activity of the piperazine propanol derivative has an effect on 1,3-beta-D-glucan synthase inhibition. Results of our initial evaluation suggest that the piperazine propanol derivative is a novel chemical structure of the class of antifungals which inhibit fungal cell growth by inhibiting fungal 1,3-beta-D-glucan synthase.     

A new benzoquinone derivative from the leaves of Garcinia parvifolia

Parvifoliquinone (1) was isolated from the leaves of Garcinia parvifolia together with six known compounds: parvifoliols B (2), C (3), E (4), garcidepsidone B (5), nigrolineaisoflavone A (6), and mangostinone (7). The structures were elucidated by spectral analyses. Their antibacterial activity against methicillin-resistant Staphylococcus aureus was evaluated.     

A new ionone derivative from the leaves of Picrasma quassioides

Nigakialcohol A (1), as unusual cyclization ionone derivative, together with eight known ones (2–9), were isolated from the leaves of Picrasma quassioides (D. Don) Benn (Simaroubaceae). Their structures were elucidated by extensive spectroscopic analyses and comparison with literature data. Compound 2 showed a weak inhibitory effect on NO production at non-cytotoxic concentration (100 μM) with inhibitory rate of 59%, and thus it should be regarded as potential anti-inflammatory agents.     

A novel spinosin derivative from Semen Ziziphi Spinosae

A novel spinosin derivative, 6?-(4?′-O-β-d-glucopyranosyl)-vanilloyl spinosin (1) was isolated from the methanol extract of Semen Ziziphi Spinosae, together with five known flavonoids, swertish (2), spinosin (3), 6?-feruloylspinosin (4), isospinosin (5) and kaempferol 3-O-α-l-rhamnopyranosyl-(1 → 2)-O-[O-α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside (6), and two alkanoids, zizyphusine (7) and 6-(2′,3′-dihydroxyl-4′-hydroxymethyl-tetrahydro-furan-1′-yl)-cyclopentene[c]pyrrole-1,3-diol (8). The structure of compound 1 was elucidated by spectroscopic methods including UV, IR, ESI-TOF-MS, 1D, and 2D NMR techniques.     

A novel polyisoprenyl benzophenone derivative from Garcinia eugeniaefolia

A novel polyisoprenyl benzophenone derivative named eugeniaphenone (1) was isolated from the stem bark of Garcinia eugeniaefolia Wall. Its structure was elucidated by spectroscopic methods, including 1D and 2D NMR techniques, and confirmed by single-crystal X-ray diffraction analysis. It is the first example in which an isoprenyl unit formed a cyclobutane-containing side chain in the polyisoprenyl benzophenone derivatives.     

A novel polyisoprenyl benzophenone derivative from Garcinia eugeniaefolia

A novel polyisoprenyl benzophenone derivative named eugeniaphenone (1) was isolated from the stem bark of Garcinia eugeniaefolia Wall. Its structure was elucidated by spectroscopic methods, including 1D and 2D NMR techniques, and confirmed by single-crystal X-ray diffraction analysis. It is the first example in which an isoprenyl unit formed a cyclobutane-containing side chain in the polyisoprenyl benzophenone derivatives.     

A novel spinosin derivative from Semen Ziziphi Spinosae

A novel spinosin derivative, 6?-(4?'-O-β-D-glucopyranosyl)-vanilloyl spinosin (1) was isolated from the methanol extract of Semen Ziziphi Spinosae, together with five known flavonoids, swertish, spinosin, 6?-feruloylspinosin, isospinosin and kaempferol 3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranoside, and two alkanoids, zizyphusine and 6-(2',3'-dihydroxyl-4'-hydroxymethyl-tetrahydro-furan-1'-yl)-cyclopentene[c]pyrrole-1,3-diol. The structure of compound 1 was elucidated by spectroscopic methods including UV, IR, ESI-TOF-MS, 1D, and 2D NMR techniques.