Chemical constituents from Salacia polysperma / 中国中药杂志

Nine compounds were isolated from the 90% ethanol extract of Salacia polysperma by silica gel, Sephadex LH-20 column chromatography, together with preparative HPLC methods. Based on HR-ESI-MS, MS, 1D and 2D NMR spectral analyses, the structures of the nine compounds were identified as 28-hydroxy wilforlide B(1), wilforlide A(2), 1β,3β-dihydroxyurs-9(11),12-diene(3),(-)-epicatechin(4),(+)-catechin(5),(-)-4'-O-methyl-ent-galloepicatechin(6), 3-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)propan-1-one(7),(-)-(7S,8R)-4-hydroxy-3,3',5'-trimethoxy-8',9'-dinor-8,4'-oxyneoligna-7,9-diol-7'-aldehyde(8), and vanillic acid(9). Compound 1 is a new oleanane-type triterpene lactone. Compounds 1, 3, 4, 7-9 were isolated from the Salacia genus for the first time. All compounds were assayed for their α-glucosidase inhibitory activity. The results suggested that compound 8 exhibited moderate α-glucosidase inhibitory activity, with an IC_(50) value of 37.2 μmol·L~(-1), and the other compounds showed no α-glucosidase inhibitory activity.

Chemical constituents and their α-glucosidase inhibitory activities of seeds of Moringa oleifera / 中国中药杂志

The chemical constituents of the seeds of Moringa oleifera were isolated and purified by using Sephadex LH-20, Toyo-pearl HW-40F, silica gel, ODS, and MCI column chromatography. The structures of compounds were identified by high-resolution mass spectrometry, ~1H-NMR, ~(13)C-NMR, HMQC, HMBC, and ~1H-~1H COSY, as well as physicochemical properties of compounds and literature data. Twelve compounds were isolated from 30% ethanol fraction of the seeds of M. oleifera and identified as ethyl-4-O-α-L-rhamnosyl-α-L-rhamnoside(1), ethyl-3-O-α-L-rhamnosyl-α-L-rhamnoside(2),(4-hydroxybenzyl)ethyl carbamate(3),(4-aminophenyl)acetic acid(4), ethyl-α-L-rhamnoside(5), methyl-α-L-rhamnoside(6), moringapyranosyl(7), 2-[4-(α-L-rhamnosyl)phenyl]methyl acetate(8), niaziridin(9), 5-hydroxymethyl furfural(10), 4-hydroxybenzeneacetamide(11), and 4-hydroxybenzoic acid(12). Among them, compounds 1 and 2 are two new compounds, compound 3 is a new natural product, and compounds 4-5 were yielded from Moringa plant for the first time. All compounds were evaluated for α-glucosidase inhibitory activity in vitro. Compound 10 showed excellent inhibitory activity with IC_(50) of 210 μg·mL~(-1).

Study on chemical constituents of sponge-associated Aspergillus terreus / 药学实践杂志

Objective To study the chemical constituents of Aspergillus terreus from sponge epiphytic fungal. Methods Sephadex LH-20 column chromatography, silica gel column chromatography and high performance liquid chroma-tography were used to separate and purify the compounds. The structures of compounds were identified by spectroscopic data. The α-glucosidase inhibitory activity and antioxidant activity of the compounds were tested by PNPG and DPPH methods, respectively. Results Eight compounds were isolated from Aspergillus terreus and identified as methyl-3,4,5-trimethoxy-2-(2-(nicotinamido) benzamido) benzoate (1), terrelumamide A (2), emeheterone (3), (8R,9S)-dihydroisoflavipucine (4), (8S,9S)-dihydroisoflavipucine (5), cyclo(S-Pro-S-Phe) (6), brevianamide F (7), terrein (8). Compound 3 showed strong inhibitory activity against α-glucosidase and the IC50 value was 14.28 μmol/L. Conclusion Compounds 3, 4, 5, and 7 were obtained from Aspergillus terreus for the first time.

In vitro antimicrobial and α-glucosidase inhibitory potential of enantiopure cycloalkylglycine derivatives: Insights into their in silico pharmacokinetic, druglikeness, and medicinal chemistry properties

The present investigation deals with the evaluation for the first time of the in vitro antimicrobial and α-glucosidaseinhibitory potential of a series of 15 enantiopure cycloalkylglycines using agar well diffusion and spectrophotometricmethods, respectively. The obtained results were compared to the positive controls. The antimicrobial results revealedthat all compounds exerted strongly inhibitory activity, especially against Gram-positive bacterial strains with the mostpotent activity was ascribed to α-γ-hydroxy-α-amino acids 11–14 [minimum inhibitory concentration (MIC) = 1.58–12.50 mg/ml, minimum bactericidal concentration (MBC) = 3.17–100 mg/ml, and minimum fungicidal concentration(MFC) = 6.25–50 mg/ml], followed by both isoxazolidine 5–9 (MIC = 1.58–12.50 mg/ml, MBC = 6.25–100 mg/ml,and MFC = 25–100 mg/ml) and isoxazine 10 (MIC = 3.17–12.50 mg/ml, MBC = 3.17–50 mg/ml, and MFC = 25–50mg/ml) compounds, and slightly inhibitory effect with α-amino-γ-lactones series 1–4 (MIC = 3.17–25 mg/ml, MBC =6.25–100 mg/ml, and MFC = 25–100 mg/ml). All the derivatives exhibited a potent α-glucosidase inhibitory activitywith compound 10 (IC50 = 30.1 ± 0.6 μM) was found to be the most active. The druglikeness and pharmacokineticprofiles have been also predicted. The in silico results indicate that all derivatives showed a resemblance with severalparameters of the antimicrobial standards, especially in terms of molecular property, bioavailability, lipophilicity,medicinal chemistry, and enzymatic inhibitory effects as well as they agree with the different drug discovery rules suchas Lipinski (Pfizer), Ghose (Amgen), Veber (GlaxoSmithKline), Egan (Pharmacia), and Muegge (Bayer) displaying ahigher druglikeness behavior.

A new phenylpropanoid glycoside from leaves of Platycladus orientalis / 中草药

Objective: To study the chemical constituents from the leaves of Platycladus orientalis, as well as their antioxidant and α-glucosidase inhibitory activities. Methods: The compounds were isolated and purified by silica gel, MCI, polyamide, and prep-HPLC chromatography, their structures were elucidated by spectral analysis. DPPH and ABTS methods were used to study the antioxidant activity, and pNPG method was used to study the α-glucosidase inhibitory activity. Results: Eleven compounds (1-11) were isolated from the 80% ethanol extract of the leaves of P. orientalis, and identified as 4-O-(1’,3’-dihydroxypropan-2’-yl)- dihydroconiferyl alcohol 9-O-β-D-glucopyranoside (1), myricetrin (2), 5,8,3’,4’-tetrahydroxy-flavone-7-O-β-D-xylopyranoside (3), isomassonianoside B (4), (-)-isopramine 9’-O-β-D-glucopyranoside (5), (7R,8S,7’S,8’R)-4,9,4’,7’-tetrahydroxy-3,3’-dimethoxy- 7,9’-epoxylignan 4-O-β-D-glucopyranoside (6), sugiol (7), totarol (8), 5,6-dehydrosugiol methyl ether (9), isopimara-8,15-dien-7-one (10) and ethanol α-L-rhamnopyranoside (11). Conclusion: Compound 1 is a new compound, named as platycloside A; In the known compounds, seven compounds (4-7, 9-11) are isolated from this plant for the first time, six compounds (4-6, 9-11) are isolated from the family Thujoideae for the first time, and four compounds (5, 6, 10, 11) are isolated from the family Cupresaceae for the first time. The compounds 2-6 showed a degree of antioxidant activities. The compounds 2 and 3 showed the α-glucosidase inhibitory activities.

New furo3,2-hisochroman from the mangrove endophytic fungus Aspergillus sp. 085242 / 中国天然药物

Four new compounds, asperisocoumarin G (1), asperisocoumarin H (2), (±)-asperisocoumarin I [(±)-3], along with the known pergillin (4) and penicisochroman L (5) were isolated from a mangrove endophytic fungus Aspergillus sp. 085242 by further chemical investigation. The structures of the new compounds, including their absolute configurations, were established by analysis of HR-ESI-MS and NMR spectroscopic data, and ECD calculation. Asperisocoumarins G-I (1-3) were new isocoumarins belonging to the class of furo[3, 2-h]isocoumarins which are rarely found in natural sources. All of the isolated compounds were evaluated for their α-glucosidase inhibitory effects, and compounds 1 and 4 showed moderate α-glucosidase inhibitory activity, respectively. In an antimicrobial test, the racemate of 3 showed antibacterial activity against Salmonella.

Isolation of flavonol rhamnosides from Pometia pinnata leaves and investigation of α-glucosidase inhibitory activity of flavonol derivatives

Pometia pinnata belonging to the Sapindaceae family has been traditionally used as the therapeutic agent for burns andwounds in Indonesia. Based on the result of the experiment conducted, the ethyl acetate fraction of P. pinnata leavesshowed strong α-glucosidase inhibitory activity. After two flavonol rhamnoside compounds were isolated from ethylacetate fraction of P. pinnata leaves methanol extract using chromatography method, their structures were identifiedas kaempferol-3-O-rhamnoside (1) and quercetin-3-O-rhamnoside (2). The ultra-performance liquid chromatographyelectrospray ionization time-of-flight mass spectrometry (UPLC-ESI-TOFMS) chromatogram showed compounds1 and 2 were the major compounds of the ethyl acetate fraction. In this study, the structure–activity relationshipamong the kaempferol, quercetin, and their derivatives bearing sugar moiety were also evaluated. Among tested eightcompounds, kaempferol 7 (percent inhibition = 80.10% ± 0.8) and quercetin 8 (percent inhibition = 82.93% ± 0.4) hadstronger α-glucosidase inhibitory activity than that of other derivatives. Among kaempferol derivatives bearing sugarmoiety, compound 1 showed the strongest activity. Moreover, compound 2 showed strong α-glucosidase inhibitoryactivity among quercetin derivatives. Therefore, it can be confirmed that the hydroxyl group at C-3 position is veryimportant for α-glucosidase inhibitory activity of flavonol compounds.

A new eudesmane type sesquiterpene from cultivated Clerodendranthus spicatus in Hainan / 中国中药杂志

Six compounds were isolated from the aerial part of cultivated Clerodendranthus spicatus in Hainan with various chromatographic techniques,and their structures were determined as:1-dehydroxy-1-oxo-rupestrinol(1),N-trans-feruloyltyramine(2),methyl 3,4-dihydroxyphenyllactate(3),caffein acid(4),methyl caffeate(5) and ethyl caffeate(6),via analysis of physicochemical properties and spectroscopic evidence.Compound 1 was a new compound,while compounds 2 and 3 were isolated from C.spicatus for the first time.Biological activity results showed that compounds 2-4 exhibited α-glucosidase inhibitory activity with different inhibition ratio.

Chemical constituents and their bioactivities from seeds of Clausena lansium / 中草药

Objective To study the chemical constituents and their biological activities of the seeds of Clausena lansium. Methods The compounds were isolated by various column chromatographic techniques including silica gel, Sephadex LH-20, semi-preparative HPLC, et al., and their structures were identified through a combined analysis of physicochemical properties, as well as NMR and MS data. The in vitro α-glucosidase inhibitory activity and nematicidal activity against Panagrellus redivivusl were screened by PNPG and Berman funnel methods, respectively. Results Eleven compounds were isolated and identified as (4R*,6R*)-6-hydroxypiperitone (1), (4S*,6R*)-6-hydroxypiperitone (2), (1S*,2S*,4R*)-1-methyl-4-(prop-l-en-2-yl) cyclohexane-1,2-diol (3), subamone (4), methyl (1R*,2R*,2’Z)-2-(5’-hydroxy-pent-2’-enyl)-3-oxo-cyclopentane acetate (5), 5-hydroxy-4-phenyl-5H-furan-2-one (6), loliolide (7), xylogranatinin (8), 2,6-dihydroxyhumula-3(12),7(13),9(E)-triene (9), xanthoxol (10), and ligballinol (11). Conclusion Compounds 1-8 are isolated from the genus for the first time, and compound 9 is first isolated from this species. Compound 8 showed strong α-glucosidase inhibitory activity, and compound 5 exhibited potent nematicidal activity.

Acylated kaempferol glycosides from flower buds of Panax ginseng and their α-glucosidase inhibitory activity / 中草药

Objective: To study the chemical constituents of flavonoids and its α-glucosidase inhibitory activity from the flower buds of Panax ginseng. Methods The compounds were isolated and purified by MCI gel, silica gel and semi-preparative HPLC chromatography, and the structures were elucidated based on the NMR and MS data. The α-glucosidase inhibitory activities of the isolated compounds in vitro were determined by 96-well microtiter plate. Results: From ethyl acetate fraction of alcohol extract of P. ginseng flower buds, five flavonoids were isolated and identified as kaempferol-3-O-(2″,3″-di-E-p-coumaroyl)-α-L-rhamnoside (1), kaempferol-3-O-(3″,4″-di-E-p-coumaroyl)-α-L-rhamnoside (2), kaempferol-3-O-(3″-Z-p-coumaroyl,4″-E-p-coumaroyl)-α-L-rhamnoside (3), kaempferol-3-O-(2″,4″-di-E-p-coumaroyl)-α-L-rhamnoside (4), and kaempferol-3-O-(2″,4″-di-Z-p-coumaroyl)-α-L-rhamnoside (5). The inhibitory activity of α-glucosidase in vitro showed that compound 3 had stronger inhibitory effect on α-glucosidase. Conclusion: Compounds 1-5 are isolated from this genus for the first time, and the phenylpropionyl acylated flavonol glycosides in P. ginseng flower buds have some inhibitory effect on α-glucosidase in vitro.

Studies on chemical constituents and activities of lignans and terpenes from stem of Moringa oleifera / 中草药

Objective: To study lignans and terpenes of Moringa oleifera Lam. Methods: The compounds were isolated and purified by various column chromatographic techniques and High Performance Liquid Chromatography (HPLC). The structures of the compounds were identified through the combined analysis of physicochemical properties and spectroscopic evidence. The antineoplastic activity, α-glucosidase and acetylcholinesterase inhibitory activity of compounds were evaluated by MTT method, PNPG method and Ellman colorimetric method, respectively. Results: Twelve compounds were isolated from M. oleifera by various chromatographic methods and were identified as lariciresinol (1), 3-(α,4-dihydroxy-3-methoxybenzyl)-4-(4-hydroxy-3- methoxybenzyl) tetrahydrofuran (2), (7S,8R)-dihydrodehydrodiconiferyl alcohol (3), macadiol (4), diethyl pinoresinol (5), pinoresinol (6), evofolin B (7), erythro-guaiacylglycerol-β-O-4’-dihydroconiferyl alcohol (8), tricyclohumuladiol (9), 9α-hydroxy-2β-methoxyclovane (10), 3β-hydroxy-oleana-11,13 (18)-dien-28-oic acid (11), oleanolic acid (12). Compounds 12 showed antineoplastic activity. Compound 1 and 2 exhibited α-glucosidase inhibitory activity. Conclusion: Compounds 1-11 are separated from Moringa Adans for the first time. This plant has the potential of developing functional product for their antineoplastic and α-glucosidase inhibitory activity.

Screening potential α-glucosidase inhibitors from Anemarrhena asphodeloides using response surface methodology coupled with grey relational analysis / 中草药·英文版

Objective: To screen potential α-glucosidase inhibitors from Anemarrhena asphodeloides. Methods: Response surface methodology employing Box-Behnken design was used to optimize conditions for the extraction of α-glucosidase inhibitory active compounds from A. asphodeloides. The powders (20.0 g) of A. asphodeloides were extracted under the optimized conditions. The extract was applied to a D-101 macroporous resin column. It was eluted with ethanol and water to give six fractions. Compounds from the active fraction were identified by UPLC-Q-TOF-MS. The structure-activity relationship was discussed based on grey relational analysis. Results: The optimum extraction conditions were as follows: ethanol concentration, 100%; extraction temperature, 51 °C; and solvent to solid ratio, 23 mL/g. It indicated that the active compounds were concentrated into 80% ethanol fraction. Twenty five steroid saponins from 80% ethanol fraction were identified by UPLC-Q-TOF-MS. Peaks 19 and 23 were tentatively identified as new structures. The predicted α-glucosidase inhibitory activities of the compounds were 7 > 2 > 1 > 22 > 23 > 3 > 9 > 21 > 24 > 4 > 13 > 8 > 14 > 16 > 17 > 25 > 6 > 19. Conclusion: The fraction eluted by 80% ethanol showed the best inhibitory activity. After analyzing the data of UPLC-Q-TOF-MS, 25 steroid saponins were tentatively identified in this fraction.

Vitellaria paradoxa nutshells from seven sub-Saharan countries as potential herbal medicines for treating diabetes based on chemical compositions, HPLC fingerprints and bioactivity evaluation / 中国天然药物

The aim of the study was to determine the feasibility of the Vitellaria paradoxa nutshell as a new medicinal resource for treating diabetes. A total of forty-one compounds were identified by HPLC-DAD-Q-TOF-MS and phytochemical methods in V. paradoxa nutshell methanol extract. Based on HPLC fingerprints, four characteristic constituents were quantified and the origin of twenty-eight V. paradoxa nutshells from seven sub-Saharan countries was compared, which were classified into three groups with chemometric method. Twenty-eight samples contained high total phenolic content, and exhibited moderate-higher antioxidant activity and strong α-glucosidase inhibitory activity. Furthermore, all fractions and isolated compounds were evaluated for their antioxidant and α-glucosidase inhibitory activities, and α-glucosidase inhibitory action mechanism of four characteristic constituents including protocatechuic acid, 3, 5, 7-trihydroxycoumarin, (2R, 3R)-(+)-taxifolin and quercetin was investigated via molecular docking method, which were all stabilized by hydrogen bonds with α-glucosidase. The study provided an effective approach to waste utilization of V. paradoxa nutshell, which would help to resolve waste environmental pollution and provide a basis for developing potential herbal resource for treating diabetes.

Quality Characteristics of Care Food (Jelly) Prepared with Wild Carrot (Daucus carota L.) Juice

This study evaluated the quality characteristics of jelly prepared with different levels (0%, 5%, 10%, 15%, 20%, and 25%) of wild carrot (WC, Daucus carota L.) juice as a care food for the elderly. The lightness, redness, yellowness, and delta (Δ) values of the jelly (Control, WCJ5, WCJ10, WCJ15, WCJ20, and WCJ25) decreased with increasing amounts of wild carrot juice added. The mechanical properties, such as hardness, springiness, chewiness, and gumminess, of the jelly were decreased with increasing amounts of wild carrot juice added. The total polyphenol and total flavonoid contents of the jelly increased with increasing amounts of wild carrot juice added. The DPPH radical scavenging activity (IC50) also increased with increasing amounts of wild carrot juice added. The α-glucosidase inhibitory effects of wild carrot (WC) and WCJ25 were 71% and 54.4%, respectively, compared to the positive control (acarbose). The lipase inhibitory effects of WC and WCJ25 were 44.2% and 14.4%, respectively, compared to the positive control group (orlistat). On the other hand, the sensory evaluation score was the best at WCJ20, which contained 20% wild carrot juice. In conclusion, WCJ20 or WCJ25 is expected to be a care food for the elderly with respect to texture as well as the antioxidant and enzymatic activity (α-glucosidase inhibitory and lipase inhibitory activities).

Phytochemical analysis and biological activities of Hertia cheirifolia L. roots extracts

OBJECTIVE@#To test the antioxidant, antimicrobial and α-glucosidase inhibitory activities of the roots extracts from Hertia cheirifolia (H. cheirifolia) L.@*METHODS@#Total phenolics and total flavonoids content of the different extracts were determined by colorimetric methods and reverse phase high-performance liquid chromatography (RP-HPLC) was performed to identify various chemical components. The different extracts were evaluated for antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2-azino-bis-3-ethylenebenzothiozoline-6-sulfonic acid (ABTS) and β-carotene bleaching tests and α-glucosidase inhibitory properties. The antimicrobial activity was carried out in vitro by the broth dilution method.@*RESULTS@#Trans-cinnamic acid, rutin hydrate, naringin and quercetin were the main compounds of the ethyl acetate extract from H. cheirifolia L. This extract has significant scavenging activity to decrease free radicals especially for DPPH and ABTS radicals. As well as, the ethyl acetate extract exhibited an antimicrobial property against bacterial strains. Bacillus licheniformis and Salmonella enterica were the most sensitive strains with minimum inhibitory concentration values of 0.156 mg/mL.@*CONCLUSION@#The ethyl acetate extract was found to be selectively antioxidant and antimicrobial.

Phytochemical analysis and biological activities of Hertia cheirifolia L. roots extracts

Objective To test the antioxidant, antimicrobial and α-glucosidase inhibitory activities of the roots extracts from Hertia cheirifolia (H. cheirifolia) L. Methods Total phenolics and total flavonoids content of the different extracts were determined by colorimetric methods and reverse phase high-performance liquid chromatography (RP-HPLC) was performed to identify various chemical components. The different extracts were evaluated for antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2-azino-bis-3-ethylenebenzothiozoline-6-sulfonic acid (ABTS[rad]

Structural characterization of polysaccharide from Cyclocarya paliurus leaves and its α-glucosidase inhibitory effect / 中草药

Objective: To extract and isolate polysaccharide from Cyclocarya paliurus leaves, characterize its structural features and study its α-glucosidase inhibitory effect. Methods: C. paliurus polysaccharide (CP50) was isolated and purified by water extraction and ethanol precipitation, deproteinization with 732 cation exchange resin and 50% ethanol precipitation. Molecular weight of CP50 was determined by high performance gel permeation chromatography-multiple angle laser light scattering (HPGPC-MALLS), and monosaccharide composition was analyzed by HPLC with PMP (1-phenyl-3-methyl-5-pyrazolone) pre-column derivatization. The structure of CP50 was characterized by methylation, Fourier transform infrared spectroscopy (FT-IR), and proton nuclear magnetic resonance spectrum (1H-NMR), respectively. The α-glucosidase inhibitory effect of CP50 was investigated by PNPG method. Results: The molecular weight of CP50 was 59 000. It contained eight kinds of monosaccharides including galacturonic acid, glucose, galactose, arabinose, mannose, xylose, rhamnose, and glucuronic acid with molar ratio of 29.1:25.6:16.5:9.3:6.7:6.1:4.1:2.6. CP50 was mainly composed of →4) GalA (1→, →4) Glc (1→ and →4) Gal (1→ with branches at C-6 position of galactose. Furthermore, our results showed that CP50 exhibited a potent inhibitory effect on α-glucosidase, and the value of IC50 was determined to be 3.3 μg/mL which was much lower than the anti-type 2 diabetes drug acarbose (193.6 μg/mL). The inhibitory mode belongs to the mixed noncompetitive inhibition. Conclusion: CP50 is a pectin-like acidic polysaccharide with complex structure. Moreover, CP50 possesses better α-glucosidase inhibitory effect and potential value for the drug development and utilization.