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Triterpenes and phytosterols as human leucocyte elastase inhibitors.

Ten triterpenes and phytosterols beta-amyrin, lupeol, lupeol acetate, ursolic acid, friedelin, canophyllol, 29-hydroxy-friedelan-3-one, beta-sitosterol, 3- O-beta- D-glucopyranosyl-beta-sitosterol, 3-O-(6'- O-palmitoyl)-beta-D-glucopyranosyl-beta-sitosterol, were evaluated as potential inhibitors of human leucocyte elastase (HLE). In this series, lupeol, ursolic acid and canophyllol showed marked HLE inhibitory activity with IC(50) values at 1.9 microM, 4.4 microM, and 2.5 microM, respectively. It appeared that HLE inhibition depended on the presence and the orientation of two reactive groups in the tested molecules, distant from 10-12 A, reacting with Arg-217 in S(4) -S(5) subsites of the extended substrate-binding domain of HLE, and S(3), respectively.

Bignoniaceae↗

Micropropagation of Anemopaegma arvense: conservation of an endangered medicinal plant.

Anemopaegma arvense (Vell.) Stellfeld ex de Souza is a medicinal species also known as Catuaba. All commercially available formulations of Catuaba have been produced from wild crafting, the gathering of plant biomass from its native habitat. Nodal segments were used as explants and 4.8 new buds per explant were induced on MS media supplemented with 4.4 microM of kinetin in 30 days. The percentage of in vitro rooting was low, although acclimatization of unrooted plants into soil was successfully achieved. For germplasm maintenance, cultures of A. arvense were stored on 4 % (w/v) sorbitol and maintained viable at low growth rate without subcultures for six months.

Bignoniaceae↗

Two new non-glycosidic iridoids from the leaves of Campsis grandiflora.

Two new non-glycosidic iridoids, which were named cachinol (1) and 1-O-methyl cachinol (2), were isolated from the methanol extract of the leaves of Campsis grandiflora together with a known iridoid cachineside I (3). The structures of compounds 1 and 2 were determined on the basis of spectroscopic methods including two dimensional NMR and high resolution mass spectrometry. All of the isolated compounds showed mild inhibitory activities on rat platelet aggregation. Compounds 1 and 3 (IC50 : 246 and 219 microM, respectively) showed about 2-fold higher inhibitory effects than acetylsalicylic acid (ASA, IC50: 412 microM) on collagen-induced aggregation. Compounds 1 and 2 (IC50: 43.2 and 38.4 microM, respectively) were about 2-fold more inhibitory than ASA (IC50: 75.2 microM), and about 4-fold more effective than their glycoside 3 (IC50: 189 microM) on AA-induced aggregation.

Animals↗

Microwave-assisted rapid cyclization of lapachol, a main constituent of Heterophragma adenophyllum.

Cyclization reactions of lapachol (1) isolated from Heterophragma adenophyllum have been studied under microwave irradiation under different conditions using alumina (acidic, basic and neutral)/silica gel/montmorillonite (KSF and K-10) as solid support along with neat reaction using 2-3 drops of DMF giving naturally occurring dehydro-alpha-lapachone (2), alpha-lapachone (3), beta-lapachone (4) depending upon the nature of support and irradiation time. A novel naphthoquinone derivative adenophyllone (5) can be synthesized from lapachol using DMF under microwaves.

Bignoniaceae↗

Phenylpropanoid and phenylethanoid derivatives from Kigelia pinnata DC. fruits.

Further phytochemical investigation of the fruits of Kigelia pinnata DC. has yielded a new phenylpropanoid derivative identified as 6-p-coumaroyl-sucrose (1) together with ten known phenylpropanoid and phenylethanoid derivatives (2-11) and a flavonoid glycoside (12). The structures of the isolated compounds were elucidated using various techniques of NMR and MS spectral analysis.

Bignoniaceae↗

Morphological and secretory characterization of extrafloral nectaries in plants of coastal Veracruz, Mexico.

BACKGROUND AND AIMS: Morphological descriptions of the extrafloral nectaries (EFNs) of certain plant species are common in the literature, but they rarely relate morphology with histology, gland distribution and secretory attributes. In this study a morphological/secretory characterization of EFNs occurring on several plant species in a tropical coastal community is made and the implications of gland attributes discussed from a functional perspective. METHODS: The morphology and nectar secretion of the EFNs of 20 plant species are characterized through scanning electron microscopy, histochemical detection of reducing sugars (Fehling's reagent) and nectar volume/concentration estimates. KEY RESULTS: Sixty-five per cent of plant species in coastal communities had EFNs on vegetative structures and 35 % of species had glands on reproductive and vegetative organs. The Fabaceae is the plant family with the most species with EFNs and most diversity of gland morphologies. Four types of vascularized nectaries and four of glandular trichomes are described; sugar-secreting trichomes are characterized using Fehling's technique, and the first descriptions of unicellular and peltate trichomes functioning as EFNs are provided. Glands of ten plant species and six genera are described for the first time. Four plant species possess more than one morphological type of EFN. Eleven species have EFNs in more than one location or organ. More complex glands secrete more nectar, but are functionally homologous to the aggregations of numerous secretory trichomes on specific and valuable plant organs. CONCLUSION: Important diversity of EFN morphology was foundin the coastal plant community studied. Both vascularized and non-vascularized EFNs are observed in plants and, for the latter, previously non-existent morpho-secretory characterizations are provided with a methodological approach to study them. It is recommended that studies relating EFN attributes (i.e. morphology, distribution) with their differential visitation by insects (i.e. ants) and the cost of maintenance to the plants are carried out to understand the evolution of these glands.

Acacia↗

Interspecific variation in vessel size, growth and drought tolerance of broad-leaved trees in semi-arid regions of Kenya.

In semi-arid regions, trees often wither during the dry season. Withering is sometimes manifest as die-back, whereby whithering results in shoot death, which progresses downward from the uppermost part of the crown. In this study, we measured the relationships between height growth and diameter at breast height, die-back frequency and severity, vessel size and specific hydraulic conductivity of four evergreen (Senna siamea (Lamk) H.S. Irwin & Barneby, Jacaranda mimosifolia D. Don, Azadirachta indica A.H.L. Juss and Acacia gerrardii Benth.) and one deciduous (Melia volkensii Gürke) plantation tree species in Kenya, which has a conspicuous dry season. Die-back occurred readily in some species, but not in others. Senna siamea showed the highest specific hydraulic conductivity and the highest growth rate among the five species and was quite susceptible to die-back. Among species, height growth and specific hydraulic conductivity were positively correlated with vessel size and negatively correlated with die-back frequency, suggesting a trade-off between growth rate and drought tolerance. This implies that an adaptation to rapid growth under humid conditions leads to low drought tolerance. However, the deciduous tree Melia volkensii showed high specific hydraulic conductivity and growth, with no symptoms of die-back, implying that a mechanism associated with the deciduous habit results in drought avoidance by reducing the requirement for water during the dry season.

Acacia↗

Phloem loading. A reevaluation of the relationship between plasmodesmatal frequencies and loading strategies.

The incidence of plasmodesmata in the minor vein phloem of leaves varies widely between species. On this basis, two pathways of phloem loading have been proposed: symplastic where frequencies are high, and apoplastic where they are low. However, putative symplastic-loading species fall into at least two categories. In one, the plants translocate raffinose-family oligosaccharides (RFOs). In the other, the primary sugar in the phloem sap is sucrose (Suc). While a thermodynamically feasible mechanism of symplastic loading has been postulated for species that transport RFOs, no such mechanism is known for Suc transporters. We used p-chloromercuribenzenesulfonic acid inhibition of apoplastic loading to distinguish between the two pathways in three species that have abundant minor vein plasmodesmata and are therefore putative symplastic loaders. Clethra barbinervis and Liquidambar styraciflua transport Suc, while Catalpa speciosa transports RFOs. The results indicate that, contrary to the hypothesis that all species with abundant minor vein plasmodesmata load symplastically, C. barbinervis and L. styraciflua load from the apoplast. C. speciosa, being an RFO transporter, loads from the symplast, as expected. Data from these three species, and from the literature, also indicate that plants with abundant plasmodesmata in the minor vein phloem have abundant plasmodesmata between mesophyll cells. Thus, plasmodesmatal frequencies in the minor veins may be a reflection of overall frequencies in the lamina and may have limited relevance to phloem loading. We suggest that symplastic loading is restricted to plants that translocate oligosaccharides larger than Suc, such as RFOs, and that other plants, no matter how many plasmodesmata they have in the minor vein phloem, load via the apoplast.

Bignoniaceae↗

Demographic spatial genetic structure of the Neotropical tree, Jacaranda copaia.

We used genotypes from six microsatellite loci and demographic data from a large mapped forest plot to study changes in spatial genetic structure across demographic stages, from seed rain to seedlings, juveniles, and adult diameter classes in the Neotropical tree, Jacaranda copaia. In pairwise comparisons of genetic differentiation among demographic classes, only seedlings were significantly differentiated from the other diameter classes; F(ST) values ranged from 0.006 to 0.009. Furthermore, only seedlings showed homozygote excess suggesting biparental inbreeding in the large diameter reproductive adults. We found very low levels of relatedness in the first distance class of trees, 1-26 cm diameter (F(ij) = 0.011). However, there was a 5- to 10-fold rise in relatedness in the smallest distance class, from the smallest to the largest tree diameter classes (F(ij) = 0.110 for individuals > 56 cm diameter). A variety of non-mutually exclusive mechanisms have been invoked perviously to explain such a pattern, including natural selection, history, or nonequilibrium population dynamics. The long-term demographic data available for this species allow us to evaluate these mechanisms. Jacaranda is a fast-growing, light-demanding species with low recruitment rates and high mortality rates in the smaller diameter classes. It successfully regenerates only in large light gaps, which occur infrequently and stochastically in space and time. These factors contribute to the nonequilibrium population dynamics and observed low genetic structure in the small size classes. We conclude that the pattern of spatial genetic transitions in Jacaranda is consistent with overlapping related generations and strong but infrequent periods of high recruitment, followed by long periods of population decline.

Bignoniaceae↗

Pharmacological study on the novel antinociceptive agent, a novel monoterpene alkaloid from Incarvillea sinensis.

To determine the antinociceptive mechanism of incarvillateine (INCA), the opiate antagonists nor-binaltorphimine (nor-BNI), beta-funaltrexamine (beta-FNA) and naltrindole (NTI) were pretreated prior to its injection in a formalin test. The antinociceptive effect of INCA was antagonized by nor-BNI (kappa-receptor antagonist) and beta-FNA (mu-receptor antagonist), while NTI (delta-receptor antagonist) did not influence its effect. Furthermore, the antinociceptive effect of INCA was blocked by theophylline (THEO), an adenosine-receptor antagonist. These results suggested that the antinociceptive effect arose from the activation of mu-, kappa-receptors and adenosine-receptor.

Alkaloids↗

Trypanocidal activity of triterpenes from Arrabidaea triplinervia and derivatives.

Ethanol extract from Arrabidaea triplinervia leaves showed in vitro activity (ED100 5.0 mg/ml) against trypomastigotes of Trypanosoma cruzi, the etiologic agent of Chagas; disease. Bioactivity-directed fractionation of this extract led to the isolation of ursolic and oleanolic acids as trypanocidal compounds besides pomolic acid (not tested) and alpinetine (inactive). A series of natural and synthetic derivatives of ursolic and oleanolic acids was simultaneously assayed for structure activity relationships (SAR) studies. Ursolic acid (ED100 0.4 mg/ml) was four times more active than oleanolic acid (ED100 1.6 mg/ml). The presence of free hydroxy and/or carboxy groups is necessary for the trypanocidal activity as could be deduced from the effect of the acetates, methyl ester, and aldehyde derivatives.

Animals↗

Studies on the constituents of Catalpa species. IX. Iridoids from the fallen leaves of Catalpa ovata G. Don.

Two new iridoids, 6-O-trans-p-coumaroyl-7-deoxyrehmaglutin A (1) and 6-O-cis-p-coumaroyl-7-deoxyrehmaglutin A (2), were isolated from the fallen leaves of Catalpa ovata G. DON. together with six artifact iridoids (3-8). Their structures were established by spectral analysis. In addition, the scavenging effects of the principal compounds isolated from this plant on 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity were examined.

Bignoniaceae↗

Quantitative determination of incarvillateine in Incarvillea sinensis by solid phase extraction and high performance liquid chromatography.

Method for rapid quantitative analysis of incarvillateine in Incarvillea sinensis by high-performance liquid chromatography (HPLC) has been developed. The sample preparation involves solid phase extraction (SPE) with a mixed-mode reversed-phase and cation-exchange cartridge. The linear calibration range for incarvillateine was 0.002-0.5 mg/ml. The limit of detection was 0.35 microg/ml (S/N=3). Intra- and interday precisions were less than 0.36% (n=6) and 1.61% (n=18), respectively. The recovery of incarvillateine was 97.61-102.44% with the relative standard deviation (RSD) ranging from 0.63 to 1.93% (n=3). This method was proposed as a simple, rapid and accurate method for quantitative determination of incarvillateine content in various samples of Incarvillea sinensis collected from different areas of China.

Alkaloids↗

Newbouldiaquinone and newbouldiamide: a new naphthoquinone-anthraquinone coupled pigment and a new ceramide from Newbouldia laevis.

Newbouldiaquinone (1), a new naphthoquinone-anthraquinone coupled pigment and a new ceramide named newbouldiamide (2), have been isolated from Newbouldia laevis, besides the known compounds lapachol (3), canthic acid, oleanolic acid, 2-methyl-9,10-anthracenedione, 2-acetylfuro-1,4-naphthoquinone, 2,3-dimethoxy-1,4-benzoquinone, 2-(4-hydroxyphenyl)ethyl triacontanoate, beta-sitosterol and beta-sitosterol glucopyranoside. The structure elucidations of the isolated new compounds were performed on the basis of spectroscopic and chemical evidence. Preliminary studies showed that 1 is moderately antibacterial against Gram-positive Bacillus megaterium and that 3 has moderate herbicidal and antibacterial activities.

Anthraquinones↗