Chemical composition and free radicals restraining activity of extracts from three Manglietia species leaves

The extracts from leaves of Manglietia insignis （Wall） Blume, Manglietia chingii Dandy and Manglietia yuyuanensis Law were prepared by organic solvent extraction and their components were analyzed by GC/MS and quantified. Meanwhile, the free radicals restraining activities were detected. The 21 compounds in M. insignis, 36 compounds in M. chigii and 20 compounds in M. yuyuanensis were identified. There were 11 common components in the extracts from three Manglietia species, and 12 components in two Manglietia species. The results of relative contents of every component in three extracts showed that the main constituents of M. insignis were terpenoids and alkene, amounting to 38.93%, followed by alkane （28.18%）, the nitrogen containing compounds （15.73%） and aromatic compounds （7.23 %）. The main constituents of leaf extract from M. chingii were the terpenoids and alkene, carboxylic acid, alkane and aromatic compounds, amounting to 30.22%, 14.17%, 13.87% and 13.29%, respectively, The main constituents of M. yuyuanensis were alcohol compounds, the terpenoids and alkene, and aromatic compounds, amounting to 28.00%, 25.38% and 18.00% respectively. The results showed that the three extracts had strong function of restraining oxygen free radicals. The ultra oxygen anions activity was restrained at the highest level, when the three extracts were diluted by hundred-fold, whereas the restraining capacity of hydroxyl free radicals reached maximum, when the three extracts were diluted by twenty-fold. The above results provide scientific evidences for further approaching the ecological healthy function of three MangUetia species     

Steroid 5α-reductase inhibitory activity of condensed tannins from woody plants

In humans, steroid 5α-reductase is involved in the development of benign prostatic hyperplasia (BPH). We tested the steroid 5α-reductase inhibitory activity of the 70% acetone extract of woody plants. The tannin polymer prepared from the 70% acetone extract showed the highest steroid 5α-reductase inhibitory activity. Furthermore, the steroid 5α-reductase inhibitory activity of tannins was not affected by the addition of superoxide dismutase or catalase. It was concluded that the steroid 5α-reductase inhibitory activity of condensed tannin was caused by binding to the steroid 5α-reductase, rather than from the peroxide/superoxide produced by tannins. The tannins, prepared from tree barks, with potential for steroid 5α-reductase inhibitory activity might be advantageous in therapy for steroid 5α-reductase diseases such as BPH or prostate cancer. Part of this report was presented at the 54th Annual Meeting of the Japan Wood Research Society, Sapporo, August 2004     

Caffeoylquinic acid derivatives isolated from the aerial parts of Gynura divaricata and their yeast α-glucosidase and PTP1B inhibitory activity

The phytochemical investigation of natural products of Gynura divaricata led to the isolation of eleven caffeoylquinic acid derivatives. They were characterized by spectrometric methods as 5-O-caffeoylquinic acid (1), 5-O-p-coumaroylquinic acid (2), 5-O-feruloylquinic acid (3), methyl 5-O-caffeoylquinate (4), 3,4-dicaffeoylquinic acid (5), 3,5-dicaffeoylquinic acid (6), 4,5-dicaffeoylquinic acid (7), methyl 3,4-dicaffeoylquinate (8), methyl 3,5-dicaffeoylquinate (9), methyl 4,5-dicaffeoylquinate (10) and ethyl 4,5-dicaffeoylquinate (11). The individual compounds were screened for the inhibition of yeast α-glucosidase and Protein Tyrosine Phosphatase 1B (PTP1B) using in vitro assays. Among the isolated compounds, 3,4-dicaffeoylquinic acid (5), 4,5-dicaffeoylquinic acid (7), methyl 3,4-dicaffeoylquinate (8) and methyl 4,5-dicaffeoylquinate (10) exhibited significant inhibitory activities against α-glucosidase. In addition, 5-O-p-coumaroylquinic acid (2), 3,5-dicaffeoylquinic acid (6) and 4,5-dicaffeoylquinic acid (7) had considerable inhibitory effect against PTP1B. Based on these findings, the caffeoylquinic acid derivatives were deduced to be potentially responsible for the anti-diabetic activity of G. divaricata. The preliminary structure–activity relationship study suggests that the number and positioning of caffeoyl groups in the quinic acid derivatives are important for both α-glucosidase and PTP1B inhibitory potency. Moreover, the corresponding methyl esters of some dicaffeoylquinic acids have enhanced inhibitory activity against yeast α-glucosidase.     

New icetexane diterpenes with intestinal α-glucosidase inhibitory and free-radical scavenging activity isolated from Premna tomentosa roots

New icetexane diterpenes (1-2); 8, 11, 13-icetexatriene-10-hydroxy, 11, 12, 16-tri acetoxyl (1) and 8, 11, 13-icetexatriene-7, 10, 11-dihydroxy-12, 13-dihydrofuran (2) along with six known compounds namely acetoxy syranzaldehyde (3), syranzaldehyde (4), coniferaldehyde (5), lupeol (6), betulin (7), and 4-(4-methoxy phenyl)-2-butanone (8) were isolated from the roots of Premna tomentosa. The structures of compounds 1 and 2 were established by detailed spectral analysis using UV, IR, ¹H NMR, ¹³C NMR, 1D, 2D and Mass. The newly isolated compounds were screened for rat intestinal α-glucosidase inhibitory and free radical (DPPH) scavenging potentiality. The new icetexane diterpenes (1, 2) and compound 3 were found to have significant α-glucosidase inhibitory and also free radical scavenging (DPPH) activities.     

Comparison of in vitro antiviral activity of tea polyphenols against influenza A and B viruses and structure–activity relationship analysis

Influenza poses a particular risk of severe outcomes in the elderly, the very young and those with underlying diseases. Tea polyphenols are the natural phenolic compounds in teas, and principally consist of catechins, proanthocyanidins, flavonols, and theaflavins, which antiviral activities have been reported recently. This study is to gain a further insight into potential of various tea polyphenols for inhibiting influenza virus infection. Five tea polyphenols exhibited inhibitory activity against influenza A virus in the trend of theaflavin > procyanidin B-2 > procyanidin B-2 digallate > (−)-epigallocatechin(EGC) > (−)-epigallocatechingallate(EGCG) with IC₅₀ values in the range of 16.2–56.5 μg/ml. Six of the tested compounds showed anti-influenza B virus activity in the order of kaempferol > EGCG > procyanidin B-2 > (−)-EGC ~ methylated EGC > theaflavin with IC₅₀ values in the range of 9.0–49.7 μg/ml. Based on these results, the structure–activity relationship (SAR) was explained as follows. First, the dimeric molecules, such as theaflavin and procyanidin B-2, generally displayed more potent antiviral activity against both influenza A and B viruses than the catechin monomers. Second, the kaempferol for inhibition of influenza B virus indicated that the more planar flavonol structure with only one C-4′ phenolic hydroxyl group in the B ring is necessary for the anti-influenza B virus activity. A similar SAR can be drawn from the assays of another enveloped RNA virus, such as respiratory syncytial virus. These results are expected to provide guides for rational design of antiviral drugs based on polyphenols.     

Pharmacokinetic study of eight coumarins of Radix Angelicae Dahuricae in rats by gas chromatography–mass spectrometry

A sensitive, specific gas chromatography–mass spectrometry (GC–MS) method was established for the quantitative determination of eight coumarins of Radix Angelicae Dahuricae including coumarin, isopsoralen, psoralen, xanthotoxin, bergapten, osthole, imperatorin and oxypeucedanin in rat plasma. Nitrendipine was used as the internal standard (IS). The plasma samples were extracted by acetonitrile. GC separation was accomplished on a DB-5MS column with temperature programmed from 160 °C (17 min) to 190 °C (10 min) at the rate of 20 °C/min, then to 240 °C (5 min) at 20 °C/min, and finally to 280 °C (14 min) at 20 °C/min. The detection was performed on a quadrupole mass spectrometer detector operated by full-scan mode (m/z 50–500). The lower limit of quantitation was 5–10 ng/mL for eight coumarins, and the linear range was 5–1000 ng/mL for the coumarins (R² > 0.9990). All the validation data were within the required limits. After oral administration, the plasma concentration–time curves showed that the time for maximum concentration (T_max) was 1.29 for coumarin, 1.83 for isopsoralen, 1.93 for psoralen, 1.30 for xanthotoxin, 2.04 for bergapten, 0.64 for osthole, 1.41 for imperatorin and 0.51 h for oxypeucedanin. The plasma concentration of the eight coumarins was low, with a mean maximum plasma concentration (C_max) < 6.41 μg/mL. Pharmacokinetic data analysis showed that the eight coumarins had different pharmacokinetic characteristics after oral administration. The method was successfully applied to pharmacokinetic studies of eight coumarins after oral administration in rats.     

Bioassay-guided isolation of urease and α-chymotrypsin inhibitory constituents from the stems of Lawsonia alba Lam. (Henna)

Seven constituents were isolated from the stems of Lawsonia alba Lam., following an activity-guided isolation, which include two new constituents, namely lawsorosemarinol (1) and lawsofructose (2), one known compound 2-(β-d-glucopyranosyloxy)-1, 4-naphthoquinone (3) and four compounds, 4-hydroxy coumarine (4), 3-(4-hyroxyphenyl)-triacontyl-(Z)-propenoate (5), 3-(4-hydroxy-3-methoxyphenyl)-triacontyl-(Z)-propenoate (6) and 7-hydroxy-4-methyl coumarin (7) first time isolated from Lawsonia alba. Their structure elucidation was based on spectroscopic data analyses. Compounds 3 and 7 showed a moderate inhibition of urease activity, while rest of them showed less than 50% inhibition. These compounds did not show any significant inhibition against α-chymotrypsin.     

Do tannins in leaves of trees and shrubs from African and Himalayan regions differ in level and activity?

Mature leaves of trees and shrubs from sub-humid tropical regions of Benin (Acioa barteri, Cassia sieberiana, Dialium guineense, Dichrostachys cinerea, Guiera senegalensis, Milletia thonningii, Piliostigma reticulatum) and arid and semiarid regions of Zimbabwe and Niger (Acacia holosericea, A. nilotica, Dichrostachys cinerea, Securidaca longepedunculata, Parinari cuvetelio, Ziziphus mucronata) in Africa, and from sub-tropical region in foot-hills of North-West Humid Himalayan range (Albizia stipulata, Bauhenia variegata, Cedrela toona, Celtis australis, Dendrocalamus hamiltonii, Grewia optiva, Leucocephala leucocephala, Morus alba, Papulus ciliata, Quercus incana, Q. semecarpifolia, Q. glauca, Q. serrata, Q. ilex, Robinia pseudoacacia, Salix tetrasperma) were analysed for crude protein, total phenols (TP), protein precipitation capacity (PPC) and operational activity of tannins (values are as mean ± SE). There was no significant difference in the crude protein values of forages obtained from the Himalayan and African region (15.2 ± 1.16 and 14.1 ± 1.19%, respectively), however the levels of TP and biological value of tannins as PPC were significantly higher for the African forages (TP 15.7 ± 4.27 vs 6.0 ± 1.0%; PPC 327.2 ± 113.6 vs 56 ± 15.9 mg bovine serum albumin precipitated/g). The operational activity of tannins expressed as mg protein precipitated per unit of phenols was also significantly higher in forages from the African regions (1.97 ± 0.47 vs 0.66 ± 0.17). For a small set of leaves from arid and semiarid zones of Middle East (Syria, A. cyanophylla; Israel, A. saligna) and India (Eugenia jambolana, Eucalyptus punctata, Prosopis cineraria and Shorea robusta) TP, PPC and tannin activity were closer to those for the African forages.This revised version was published online in November 2005 with corrections to the Cover Date.     

Characterization of tyrosinase inhibitors in the twigs of Cudrania tricuspidata and their structure–activity relationship study

The twigs of Cudrania tricuspidata were found to show strong tyrosinase inhibitory activity, and further detailed component analysis resulted in the isolation of a new flavanol glucoside, (2S,3S)-2,3-trans-dihydromorin-7-O-β-d-glucoside (1), plus twenty-seven known compounds (2–28). Their structures were elucidated on the basis of ESI-MS and NMR spectral data. Among the isolated compounds, trans-dihydromorin (8), oxyresveratrol (9), and steppogenin (12) were found to exhibit significant tyrosinase inhibition activities. Moreover, the structure–activity relationship of these isolated compounds was also discussed.     

Iridoid and phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl. and their α-Glucosidase inhibitory activities

A new phenylpropanoid glycoside, designated Scrophuside (1) and two new iridoid glycosides, respectively named Ningposide I (2) and Ningposide II (3), along with twelve known (4–15) iridoid and phenylpropanoid glycosides were obtained from the roots of Scrophularia ningpoensis Hemsl. by various chromatographic techniques and their structures were established through chemical methods and spectroscopic analyses. Most of the obtained compounds have been screened for α-Glucosidase inhibitory activity, in which compounds 4, 5, 7, 11, 12, 13, and 14 show significant activity.     

α-Glucosidase inhibitory triterpenoids from the stem barks of Uncaria laevigata

A phytochemical study on the ethanolic extract of the stem barks of Uncaria laevigata leads to the isolation and characterization of 18 triterpenoid compounds. Ten of these are new, including one novel heptanortriterpenoid (1), four ursane triterpenes (2–4, 10), and five oleanane triterpenes (5–9). Their structures were established by spectroscopic methods, especially by 2D-NMR and MS analyses. All these isolates were evaluated for their inhibitory effects on α-glucosidase: ursolic acid and 3 showed potent activities with IC₅₀ values of 16 ± 2.2 and 49 ± 3.7 μM, respectively.     

The cytotoxic activities of cardiac glycosides from Streptocaulon juventas and the structure–activity relationships

A series of cardiac glycosides were isolated and identified from the anti-tumor fraction of the root of Streptocaulon juventas in previous studies. In the present research, the cytotoxic activities of the 43 cardiac glycosides on three cell lines, human lung A549 adenocarcinoma cell, large cell lung cancer NCI-H460 cell and normal human fetal lung fibroblast MRC-5 cell, were evaluated in vitro. Most of the tested compounds showed potent inhibitory activities toward the three cell lines. Then, the structure–activity relationships were discussed in detail. It was indicated that hydroxyl and acetyl groups at C-16 increased the activity, whereas hydroxyl group at C-1 and C-5 can both increase and decrease the activity. Two glucosyl groups which were connected by C1′ → C6′ showed better inhibitory activity against cancer cell lines, while the C1′ → C4′ connection showed stronger inhibitory activity against the normal cell line. Also, this is the first report that the activities of these compounds exhibited different variation trends between A549 and NCI-H460 cell lines, which indicated that these compounds could selectively inhibit the cell growth. The results would lay a foundation for further research on new anti-tumor drug development.     

Microbial transformation of ginsenoside-Rg₁ by Absidia coerulea and the reversal activity of the metabolites towards multi-drug resistant tumor cells

Biotransformation of ginsenoside-Rg₁ (1) by the fungus Absidia coerulea AS 3.2462 yielded five metabolites (2? 6). On the basis of spectroscopic data analyses, the metabolites were identified as ginsenoside-F₁ (2), 6α,12β-dihydroxydammar-3-one-20(S)-O-β-D-glucopyranoside (3), 3-oxo-20(S)-protopanaxatriol (4), 3-oxo-7β-hydroxy-20(S)-protopanaxatriol (5), and 3-oxo-7β,15α-dihydroxy-20(S)-protopanaxatriol (6), respectively. Among them, 5 and 6 are new compounds. These results indicated that Absidia coerulea AS 3.2462 could catalyze the specific C-3 dehydrogenation of derivatives of ginsenoside-Rg₁, as well as hydroxylation at the 7β and 15α positions. Metabolites 2, 4 and 5 exhibited moderate reversal activity towards A549/taxol MDR tumor cells in vitro.     

Changes in the biochemical composition and enzyme activity during dormancy release of Cyclocarya paliurus seeds

Cyclocarya paliurus is only propagated from seeds which have pronounced dormancy. Overcoming seed dormancy is an important component of efficient and cost-effective seedling production of Cyclocarya paliurus. Changes in biochemical composi-tion and enzyme activity were investigated during dormancy release. The activities of all the studied enzymes in the stratified seeds increased significantly, compared to those in the control samples. Of the enzymes examined, the activities of protease increased the most (413.8%), followed by peroxidase (278.7%), lipase (161.0%), glucose-6-phosphate dehydrognase (149.1%) and amylase (60.6%) after 8 months of stratification. Crude fat and protein constituted the bulk of the storage reserves in mature seeds of C. pali-urus. Compared with the seeds before stratification, about 45% of the starch, 46% of the protein and 11% of the crude fat were de-pleted during dormancy release of C. paliurus seeds, while the soluble sugar content was enhanced by 101.5% in the germinating seeds. Correlation analysis showed, during dormancy release of C. paliurus seeds, a close positive relationship between POD and G6PDH activity as well as soluble sugar content and amylase activity, while there was a significant negative relationship between storage substances and their related enzyme activities.     

Dynamic adsorption of α-pinene and linalool on silica nanoparticles for enhanced antifeedant activity against agricultural pests

The terpene compounds, α-pinene and linalool were formulated with silica nanoparticles (SNPs) by a simple immersion method and the antifeedant activity of these formulations was evaluated against two major agricultural pests, the tobacco cutworm (Spodoptera litura F.) and the castor semilooper (Achaea janata L.) in laboratory bioassays. The interaction between terpenes and SNPs, shelf-life, suspension stability as well as the bioactivity of the nanoformulations were also studied. Both these terpenes in their pure form are known to deter feeding in several lepidopterous insects. However, formulating these pure terpene compounds with nano silica enhanced their biological activity up to 25 times to S. litura. Fourier transform infrared spectroscopy analysis of these nano botanical formulations indicated the presence of hydrogen bonding between terpenes and the surface of SNPs. Transmission electron microscopy images confirmed the higher aggregation property of the SNPs. Suspension studies validated the improved shelf-life of the nano-biocomposites, while X-ray diffraction (XRD) revealed the amorphous nature of formulations and no crystalline impurities. Adsorption of α-pinene and linalool onto SNPs resulted in an effective formulation that enhanced the antifeedant potential of the individual terpenes against insects while producing longer shelf-life for the terpenes.     

Protective enzyme activity and physiological properties of four mulberry varieties affected by drought stress in the Panxi Region of Sichuan Province, China

In order to identify the effects of drought stress on protective enzyme activity and physiological properties, four mulberry varieties, i.e.,‘Nanye-1’, ‘Yunsang-1’, ‘Xinyizhilai’ and ‘Husang-32’ in the Panxi Region of Sichuan Province, China, were selected. The activity of superoxide dismutase (SOD), peroxidase (POD) and catalase (CAT) in four mulberry varieties was determined. Soluble protein, soluble sugar, proline, net photosynthetic rate and transpiration rate of mulberry leaves were analyzed. The resul...     

In vitro antioxidant activity of species collected in Paraná

Hydroalcoholic extracts of 10 medicinally used species collected from the area covered by a reservoir due to a dam built for the Salto Caxias Hydro-electric power plant in the State of Paraná, Southern Brazil, and Casearia sylvestris, were investigated for their potential antioxidant activity against DPPH (1,1-diphenyl-2-picrylhydrazyl) free radicals and by the phosphomolybdenum method. The extract of Bauhinia microstachya was found to be the most potent in both models.