Phytochemistry and pharmacological activities of five species of Bauhinia genus: A review.

Genus Bauhinia has been widely used in the treatment of diabetes, malaria, cough, headache, fever, piles, dysentery, flatulence, diarrhoea, ulcer and cardiovascular problems. Among 600 species of this genus, Bauhinia variegata, B. purpurea, B. championii, B. racemosa, and B. forficata are commonly used in the traditional medicine and found to be throughly investigated for their medicinal properties. They possess diverse pharmacological activities such as anti-diabetic, anti-microbial, antioxidant, anti-arthritic, cardioprotective, hepatoprotective, nephroprotective, fibrinolytic, and wound healing properties and most of the biological activities are corelating with traditional knowledge. Phytochemical analysis indicated that steroids, terpenoids, and flavonoids are prominent in the selected species, whereas bauhiniastatins, bauhinoxepins, racemosols, roseosides, and bauhichamines are found unique to the genus. This review aims to decipher active molecules from the aforementioned species of Bauhinia covering comprehensive analysis of phytochemistry, pharmacological activities and traditional uses. The data has been carefully analyzed to find compounds or fractions with a translational value. In most of the cases, the pharmacological activities have been established, however, further studies are needed such as safety evaluations, target identification, bioavailability, metabolite identification, and pharmacokinetic properties. In conclusion, the pharmacological potential of Bauhinia plants show promise with various leads such as insulin-like protein, roseoside, bauhiniastatin, and melibiose binding lectin. However, further investigations are required to address existing gaps and advance them towards product development. This review will lay the groundwork for future research initiatives aimed at fully realizing the therapeutic potential of Bauhinia plants.

The anticancer activity of two glycosides from the leaves of Leea aequata L.

Two compounds (7-O-methylmearnsitrin (7-OM) and roseoside A (RA) were identified and characterized from the leaves of Leea aequata (L. aequata) L. The cytotoxicity of 7-OM and RA on HeLa cells was performed using MTT. The 7-OM and RA showed significant inhibition of HeLa cell proliferation with an IC50 of 22 and 20 µg/mL, respectively when compared with the standard vincristin sulphate (VS) (IC50 of 15 µg/mL). Moreover, the 7-OM and RA significantly inhibit other cancer cells (HEK-293, H228, and H3122) when compared with the VS and the cytotoxic activity of the compounds might show through the induction of apoptosis. Strikingly, annexin-V and PI signals could barely be detected in control cells, while strong fluorescence densities were observed in response to treatment indicating that these compounds have capacity to induce HeLa cell apoptosis. Our results suggest that the anticancer activity of 7-OM and RA was due to the induction of apoptosis.

UPLC-QTof-MSE Metabolomics Reveals Changes in Leaf Primary and Secondary Metabolism of Hop (Humulus lupulus L.) Plants under Drought Stress.

The hop (Humulus lupulus L.) is an important specialty crop used in beer production. Untargeted UPLC-QTof-MSE metabolomics was used to determine metabolite changes in the leaves of hop plants under varying degrees of drought stress. Principal component analysis revealed that drought treatments produced qualitatively distinct changes in the overall chemical composition of three out of four genotypes tested (i.e., Cascade, Sultana, and a wild var. neomexicanus accession but not Aurora), although differences among treatments were smaller than differences among genotypes. A total of 14 compounds consistently increased or decreased in response to drought stress, and this effect was generally progressive as the severity of drought increased. A total of 10 of these marker compounds were tentatively identified as follows: five glycerolipids, glutaric acid, pheophorbide A, abscisic acid, roseoside, and dihydromyricetin. Some of the observed metabolite changes likely occur across all plants under drought conditions, while others may be specific to hops or to the type of drought treatments performed.

Inhibitory Effects of Roseoside and Icariside E4 Isolated from a Natural Product Mixture (No-ap) on the Expression of Angiotensin II Receptor 1 and Oxidative Stress in Angiotensin II-Stimulated H9C2 Cells.

Hypertension is a major risk factor for the development of cardiovascular diseases. This study aimed to elucidate whether the natural product mixture No-ap (NA) containing Pine densiflora, Annona muricate, and Monordica charantia, or its single components have inhibitory effects on hypertension-related molecules in Angiotensin II (Ang II)-stimulated H9C2 cells. Individual functional components were isolated and purified from NA using various columns and solvents, and then their structures were analyzed using ESI⁻MS, ¹H-NMR, and 13H-NMR spectra. H9C2 cells were stimulated with 300 nM Ang II for 7 h. NA, telmisartan, ginsenoside, roseoside (Roseo), icariside E4 (IE4), or a combination of two components (Roseo and IE4) were administered to the cells 1 h before Ang II stimulation. The expression and activity of hypertension-related molecules or oxidative molecules were determined using RT-PCR, western blot, and ELISA. Ang II stimulation increased the expression of Ang II receptor 1 (AT1), tumor necrosis factor-α (TNF-α), monocyte chemoattractant protein-1 (MCP-1), tumor growth factor-ß (TGF-ß) mRNA, and nicotinamide adenine dinucleotide phosphate (NADPH) oxidase activity and the levels of hydrogen peroxide (H2O2) and superoxide anion (•O2-) and reduced anti-oxidant enzyme activity. NA significantly improved the expression or activities of all hypertension-related molecules altered in Ang II-stimulated cells. Roseo or IE4 pretreatment either decreased or increased the expression or activities of all hypertension-related molecules similar to NA, but to a lesser extent. The pretreatment with a combination of Roseo and IE4 (1:1) either decreased or increased the expression of all hypertension-related molecules, compared to each single component, revealing a synergistic action of the two compounds. Thus, the combination of single components could exert promising anti-hypertensive effects similar to NA, which should be examined in future animal and clinical studies.

Chemical constituents from stems of Uncaria lancifolia / 中草药

Objective To study the chemical constituents from the stems of Uncaria lancifolia. Methods The isolation and purification were carried out by silica gel column chromatography, RP18, Sephadex LH-20, and preparative HPLC. The structures of the isolated compounds were elucidated by physical and chemical properties, and spectroscopic methods. Results Eighteen compounds were isolated and identified from 95% ethanol extract from the stems of U. lancifolia and characterized as uncarine A (1), uncarine E (2), isomitraphylline (3), tetrahydroalstonine (4), strictosidine (5), cadambine (6), glabratine (7), strictosamide (8), (13R)-hydroxy- octodeca-(9Z,11E,15Z)-trien-oic acid (9), (6S,9R)-roseoside (10), periplanetin (11), integracin A (12), integracin B (13), 6β,19α- dihydroxyurs-3-oxours-12-en-28-oic aicd (14), ursolic acid (15), oleanic acid (16), β-sitosterol (17), and β-daucosterol (18). Conclusion This is the first report for the chemical constituents from U. lancifolia. All compounds are obtained from this plant for the first time, and compounds 9-13 are isolated from Uncaria genus for the first time. Compounds 1-8 are monoterpene indole alkaloids, which are characteristic constituents in Uncaria genus.

Polyphenolic profile and antioxidant activities of Madeiran elderberry (Sambucus lanceolata) as affected by simulated in vitro digestion.

The aims of this study were twofold: a) to provide a detailed report on the phenolic composition and antioxidant activity of fresh berries and leaves of Sambucus lanceolata (Madeiran elderberry); b) to study the effects caused by a simulated in vitro digestion on the composition and antioxidant activity of the berries and leaves. Seventy-seven phytochemicals, mainly polyphenols, were identified in the methanol extracts of fresh berries and leaves, with the content of polyphenols higher in berries (27.2mg·g-1 dry extract, DE) than in leaves (25.9mg·g-1 DE). Anthocyanins were dominant in berries, while hydroxycinnamic acids (HCAs) and flavonols were abundant in leaves. Higher antioxidant activities were found in leaves than in berries, using several in vitro assays. After the simulated in vitro digestion, the levels of polyphenols were significantly reduced, in particular those of berries (81.8% decrease). Anthocyanins were the most affected compounds during the simulated digestion. However, despite the significant loss of phenolic compounds during digestion, methanol extracts of digested berries and leaves were still able to scavenge free-radicals. Hence, the consumption of leaves and/or berries of S. lanceolata may help prevent oxidative stress.

Chemical constituents from anti-inflammatory and analgesic active fraction of Gaultheria leucocarpa var. yunnanensis / 中草药

Objective To study the chemical constituents from anti-inflammatory and analgesic active fraction (ARF) of Gaultheria leucocarpa var. yunnanensis. Methods The compounds were isolated and purified by various techniques of column chromatography, and their structures were determined according to physicochemical properties and spectral analyses. Results Sixteen compounds were obtained and identified as methyl salicylate 2-O-β-D-glucopyranoside (1), gaultherin (2), MSTG-A (3), MSTG-B (4), ethyl-O-β-D-xylopyranoside (5), ethyl-O-β-D-xylopyranosyl (1→6)-O-β-D-glucopyranoside (6), methyl-O-β-D-xylopyranosyl (1→6)-O-β-D-glucopyranoside (7), roseoside (8), paeoniflorin (9), vanillic acid (10), 2,5-dihydroxybenzoic acid (11), 3,4-dimethoxycinnamic acid (12), ferulic acid (13), chlorogenic acid (14), 4-hydroxy-2,6-dimethoxyphenol-O-β-D-glucopyranoside (15), and 3-methoxyl-1H-pyrrole (16). Conclusion Compounds 5-9, 12, 15, and 16 are obtained from this plant and compound 7 is isolated from the plants of genus Gaultheria Kalm ex L. for the first time. Compounds 8, 9, 12, and 15 are obtained from family Ericaceae for the first time.

Norsesquiterpenoids and triterpenoids from strawberry cv. Falandi.

Falandi is a common strawberry (Fragaria × ananassa Duch.) cultivar in southern China. Further study of the chemical constituents in Falandi fruit led to the isolation of nine norsesquiterpenoids and three triterpenoids. Falandioside D (1) and falandins A (2) and B (3) were new norsesquiterpenoids, and the others excluding tormentic acid (11) were found in strawberry for the first time. Compounds 1 and 11 exhibited potent α-glucosidase inhibitory activity with the half maximal inhibitory concentration (IC50) values of 565.0 and 27.4 µM in comparison to acarbose (619.9 µM). Compounds 3, 7 (blumenol C glucoside), and 11 showed cytotoxicity against human nasopharyngeal carcinoma cell line CNE1 with the IC50 values of 57.6, 56.4, and 36.0 µM, respectively. Among new compounds, 1 showed 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical cation scavenging capacity (IC50=36.2 µM). These results suggested that non-phenolic constituents were also involved in the antidiabetic, antitumour, and antioxidant effects of strawberry fruit.

Studies on chemical constituents from fresh pineneedles of Pinus massoniana / 中草药

Objective: To study the chemical constituents from the fresh pineneedles of Pinus massoniana. Methods: Certain chromatography means were used in the isolation and purification, and the structures of all the compounds were identified by means of spectroscopic analysis and physicochemical properties. Results: Fourteen compounds were elucidated respectively as (+)-catechin (1), (+)-gallcatechin (2), phlorin (3), tachioside (4), 3,4-dimethoxyphenyl-1-O-β-D-glucopyranoside (5), 3,4-dimethoxyphenyl-1- O-(3-O-methyl-α-L-rhamnopyranosyl)-1→2-β-D-glucopyranoside (6), citrusin D (7), (6S,7E,9R)-roseoside (8), raspberry ketone- O-β-D-glucopyranoside (9), (-)-oplopan-4-one-10-α-O-β-D-glucose (10), massonianoside D (11), massonianoside B (12), isolariciresinol-9'-O-α-L-arabinofuranoside (13), and (2R,3R)-taxifolin-3'-O-β-D-glucopyranoside (14). Conclusion: Compounds 2-6, and 10 are isolated from the plants of Pinus L. for the first time, and compounds 7-9 are obtained from P. massoniana for the first time.

Phytochemical analysis and bioactivity of the aerial parts of Abutilon theophrasti (Malvaceae), a medicinal weed.

Phytochemical investigations of aerial parts of Abutilon theophrasti yielded (6S,9R)-roseoside (1) and (6S,9S)-roseoside (2) which are new for the genus. The elucidation of the chemical structures was established by mass spectrometry, 1D and 2D NMR experiments. Although methanol extracts contained 48.5 ± 7.2 mg of caffeic acid equivalents and 15.87 ± 4.6 mg of quercetin equivalents, the antioxidant activity, as revealed by DPPH and ABTS assays, was of medium strength (EC50 of 306.2 ± 16.3 and 394.3 ± 14.8 µg/mL, respectively). A. theophrasti extract inhibits soybean 5-LOX with IC50 value 2.89 ± 0.2 mg/mL. The cytotoxicity of the methanol extract against MCF-7, CCRF-CEM and CEM/ADR5000 cancer cells resulted in IC50 values of 505.8 ± 34.7 µg/mL for MCF-7, 75.6 ± 7.1 µg/mL for CCRF-CEM, and 89.5 ± 13.4 µg/mL for CEM/ADR 5000 cells.

Study on chemical constituents in shells of Juglans sigillata / 中草药

Objective: To investigate the chemical constituents in the shells of Juglans sigillata. Methods: The chemical constituents were isolated by silica gel, RP18, Sephadex LH-20, and MCI column chromatography and semi-preparative HPLC and so on. The structures were identified on the basis of spectroscopic analysis and chemical evidence. Results: Fifteen compounds were isolated and identified in the 70% ethanol extract from the shells of J. sigillata including seven phenolic glycosides: tachioside (1), mudanoside A (2), 4-O-β-D-glucopyranosylvanillc acid (3), breynioside A (4), 1-O-vanilloyl-β-D-glucose (5), 6'-O-vanilloyltachioside (6), and 6'-O-vanilloylisotachioside (7); three phenylpropanoide acid glycosides: 6-O-feruloyl-D-glucopyranose (8), methyl-4-O-coumaroylquinate (9), and 5-p-cis-coumaroylquinic acid (10); two tetralone glycosides: juglanin A (11) and juglanin E (12); one norsesquiterpenes glycoside: roseoside (13); one flavone: toxifolin (14); and one glucosylated abscisic acid derivate: (1'R, 3'R, 5'R, 8'S)-epi-dihydrophaseic acid β-D-glucoside (15). Conclusion: Except compound 14, the other compounds are isolated from the shells of J. sigillata for the first time. And compounds 1-4, 13, and 15 are reported for the first time from the plants in genus of Juglans L.

Chemical constituents of Euphorbia royleana / 中草药

Objective: To study the chemical constituents in the aerial parts of Euphorbia royleana. Methods: The constituents were isolated and purified by chromatographic of silica gel, Sephadex LH-20, RP18, and MCI columns, and their structures were elucidated by spectroscopic analyses. Results: Twelve compounds were isolated from the 70% acetone extracts in the aerial parts of E. royleana and their structures were identified as (6S, 9R)-roseoside (1), 13-carboxyblumenol C 9-O-β-glucoside (2), 3, 3'-dimethylellagic acid-4-O-β-D-glucopyranoside (3), cycloart-23-ene-3β, 25-diol (4), 23(E)-25-methoxycycloart-23-en-3β-ol (5), α-amyrin (6), triptohypol F (7), 9(11), 12-dieneoleana-3β-ol (8), friedelane-3β, 29-diol (9), D:A-friedoolean-29-ol-3-one (10), dischidiol (11), and lupeol (12). Conclusion: Compounds 1, 2, 7-11 are obtained from the plants in Euphorbia L. for the first time and compounds 3-5 and 12 are isolated from this plant for the first time.

Chemical constituents in butanol extraction from stems and leaves of Arachis hypogaea / 中草药

Objective To investigate the chemical constituents in the stems and leaves of Arachis hypogaea.Methods The isolated compounds Ⅰ—Ⅳ were obtained by the combination of silica gel,ODS-18,and Sephadex LH-20 column chromatographies.Structural elucidation was conducted by the moedrn spectral method.Results Seventeen compounds were isolated and identified from the water extraction,and there were four norsesquiterpene compounds from butanol extraction.They are arachiside A(Ⅰ),cucubalactone(Ⅱ),roseoside(Ⅲ),and citroside A(Ⅳ).Conclusion Compound Ⅰ is a new compound named arachiside A and compounds Ⅱ—Ⅳ are isolated from the plants of Arachis Linn.for the first time.