Chemical constituents from Morinda citrifolia and their inhibitory activities on proliferation of synoviocytes in vitro / 中国中药杂志

The chemical constituents from the stems and leaves of Morinda citrifolia were isolated and purified by column chromatography methods with silica gel, ODS, Sephadex LH-20 and preparative high performance liquid chromatography(HPLC). The structures of the isolated compounds were identified by physicochemical properties and spectroscopic analysis, as well as comparisons with the data reported in literature. 17 compounds were isolated from the 90% ethanol extract of the stems and leaves of M. citrifolia, and were identified as 9,10-dihydroxy-4, 7-megastigmadien-3-one(1), 5,12-epoxy-6,9-hydroxy-7-megastigmen-3-one(2), fukinone(3), β-eudesmol(4), sarmentol F(5), 4, 5-dihydroblumenol A(6), 3-hydroxy-β-ionone(7), aristol-8-en-1-one(8), ergosta-7-en-3β-ol(9), ergosta-7-ene-3β,5α,6β-triol(10),(22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol(11), olivil(12), 4-epi-larreatricin(13), chushizisin Ⅰ(14), rabdosia acid A(15), glycerol monolinoleate(16) and(9Z,12Z,15Z)-2,3-dihydroxypropyl octadeca-trienoate(17). All compounds were isolated from M. citrifolia for the first time. All isolated compounds were evaluated for their anti-rheumatoid arthritis activities via examining their inhibitory activities on the proliferation of synoviocytes in vitro using MTS met-hod. Compounds 1-11 showed significant anti-rheumatoid arthritis activities, displaying the inhibitory effects on the proliferation of MH7 A synovial fibroblast cell with the IC_(50) values ranging from(38.69±0.86) to(203.45±1.03) μmol·L~(-1).

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.

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.

Syntheses of alkyl-de-sanguinarine-N5-methyl derivatives and evaluation of in vitro growth inhibitory activities against cancer cell lines / 药学学报

2,3:7,8-Bis(methylenedioxy)benzo[c]phenanthridine was synthesized in a strategy of converging synthesis with 6-bromo-2,3-dihydroxybenzaldehyde, 5-nitronaphthalene-2,3-diol, and dibromomethane, respectively, as starting materials. The reaction process included dioxy-de-dibromo nucleophilic substitution under alkaline condition, reduction reaction, Schiff base-forming reaction, and an arene radical cyclization step under the presence of Bu3SnH and AIBN as radical initiator, among others. The 2,3:7,8-bis(methylenedioxy)benzo[c] phenanthridine as intermediate was reacted with NaBH4 and different aliphatic acids as alkylation agent to afford 2,3:7,8-bis(methylenedioxy)-5,6-dihydro-N5-alkylbenzo[c]phenanthridines. These dihydro-type products were aromatized using DDQ as oxidant under alkaline condition, and then, salinized using HCl as source of equilibrium anion to yield the series of target alkyl-de-sanguinarine-N5-methyl derivatives. All the synthesized alkyl-de-sanguinarine-N5-methyl derivatives exhibited significantly improved in vitro growth inhibitory activities against cancer cell lines as compared with sanguinarine and the positive control. In pharmacological experiments targeting five cancer cell lines, the target compounds showed activities five-fold active than that of sanguinarine. The findings of this study indicated that the structure modification strategy of substituting n-alkyls for the N5-methyl of natural sanguinarine can be used to improve the growth inhibitory activities against cancer cell lines through increasing liposolubility and steric hindrance to protect the active 5,6-imine structure.

Chemical constituents from fruiting bodies of Ganoderma daiqingshanense / 中草药

Objective: To study the chemical constituents of the fruiting bodies of Ganoderma daiqingshanense. Methods: The constituents were separated by Silica gel and Sephadex LH-20 column chromatography, their structures were elucidated by spectral data analyses, and the acetylcholinesterase inhibitory activity was detected. Results: Twelve compounds were isolated from the fruiting bodies of G. daiqingshanense and identified as 3β,21β-serratenediol-3-acetate (1), 3β,21α-serratenediol-3-acetate (2), 3-O-acetyltohogenol (3), 20 (29)-lupen-3β-ol (4), lucialdehyde A (5), ganoderic acid Y (6), ergosta-7,22E-diene-3-one (7), ergosta-4,6,8 (14),22-tetraene-3-one (8), ergosta-7,22E-diene-3β-ol (9), 5α,8α-epidioxyergosta-6,22E-diene-3β-ol (10), ankylosaurus acid (11), and euphorbia factor L3 (12). Compounds 5, 11, and 12 showed moderate activities against acetylcholinesterase with inhibitory rates of 17.70%, 22.89%, and 21.22%, respectively. Conclusion: All the compounds are obtained from G. daiqingshanense for the first time and serratene triterpenes (compounds 1-3) are found from family Ganodermataceae for the first time. Compounds 5, 11, and 12 have certain inhibitory activities on acetylcholinesterase.

Bioassay-guided isolation of novel and selective urease inhibitors from Diospyros lotus / 中国天然药物

Two new dimeric naphthoquinones, 5',8'-dihydroxy-6,6'-dimethyl-7,3'-binaphthyl-1,4,1',4'-tetraone (1; Di-naphthodiospyrol D) and 5',8'-dihydroxy-5,8-dimethoxy-6,6'-dimethyl-7,3'-binaphthyl-1,4,1',4'-tetraone (2; Di-naphthodiospyrol E), along with known naphthoquinones diospyrin (3) and 8-hydroxy diospyrin (4) were isolated from the chloroform fraction of extract of Diospyros lotus roots. Their structures were elucidated by advanced spectroscopic analyses, including HSQC, HMBC, NOESY, and J-resolved NMR experiments. The fractions and compounds 1-4 were evaluated for urease activity and phosphodiesterase-I, carbonic anhydrase-II and α-chymotrypsin enzyme inhibitory activities. Compounds 1 and 2 and their corresponding fractions showed significant and selective inhibitory effects on urease activities. The IC values of 1 and 2 were 260.4 ± 6.37 and 381.4 ± 4.80 µmol·L, respectively, using thiourea (IC = 21 ± 0.11 µmol·L) as the standard inhibitor. This was the first report demonstrating that the naphthoquinones class showed urease inhibition.

Design,synthesis and anti-tumor activities in vitro of novel 3-substituted indolin-2-one compounds / 药学实践杂志

Objective To compose and evaluate anti‐tumor activities of 3‐substituted indole‐2‐one compounds which may have dual inhibitory activities against both tubulin protein and VEGFR‐2 tyrosine kinase .Methods Target compounds were prepared starting from substituted aniline viacondensation ,cyclization and reduction .Results 11 target compounds were syn‐thesized and all the compounds displayed moderate anti‐proliferative activities against three tumor cell lines .Compound j9 showed a certain inhibitory activity against both VEGFR‐2 kinase and tubulin protein in vitro .Conclusion This series of indo‐lin‐2‐one derivatives were found to be a novel kind of multi‐target inhibitor .

Synthesis and xanthine oxidase inhibitory activities of 2-phenyl-tetrahydrothiopyrano［4, 3-d］ pyrimidine derivatives / 中国药科大学学报

@#Twelve novel 2-phenyl -tetrahydrothiopyrano［4, 3-d］pyrimidine derivatives were synthesized from 4-hydroxy-benzonitrile by etherification, hydrolysis, acylation and addition reactions, etc. The inhibitory activities against xanthine oxidase were evaluated in vitro. Results showed that compounds 8a-8h exhibited varying inhibitory potencies on xanthine oxidase at 100 μmol/L, significantly better than those of compounds 6a-6d, indicating that carboxy-substituted pyrimidine is beneficial to the inhibitory activity. Among compounds 8a-8h, 8f with isopropionic acid-substituted pyrimidine and ethyl-substituted phenol showed the best inhibition with IC50 of 76. 0 μmol/L.

A novel diterpene from Caesalpinia minax / 中草药

Objective To study the chemical constituents of Caesalpinia minax.Methods The chemical constituents were isolated and purified by various chromatographic methods and their structures were elucidated by the analysis of spectral data and physicochemical properties.Results One diterpene compound was isolated from the 95% alcohol extract of C.minax,which was named minaxin A,and the inhibitoryactivitiesofthecompoundonHepG2cellwerestudiedbyuseofMTTmethod.ConclusionMinaxin A is a new compound and shows the significant inhibitory activities on HepG2 cell.