A novel diphenylbutenoid-type compound from the rhizomes of Zingiber montanum (J.Koenig) Link ex A.Dietr. (Zingiberaceae).

From the EtOAc-soluble extract of the rhizomes of Zingiber montanum (J.Koenig) Link ex A.Dietr., a novel diphenylbutenoid, montadinin A (1) and a previously unreported phenylbutenoid compound, 1-(3,4-dimethoxyphenyl)but-3-en-2-ol (7), in natural source were isolated. Additionally, seven known phenylbutenoids were also identified. The structures of all compounds were elucidated through NMR spectroscopic interpretation. Compounds cis-3-(3,4-dimethoxyphenyl)-4-[(E)-3,4-dimethoxystyryl]cyclohex-1-ene (2), cis-4-[(E)-3,4-dimethoxystyryl]-3-(2,4,5-trimethoxyphenyl)cyclohex-1-ene (3), trans-3-(3,4,-dimethoxyphenyl)-4-[(E)-2,4,5-trimethoxystyryl]cyclohex-1-ene (5), and cis-3-(3,4-dimethoxyphenyl)-4-[(Z)-2,4,5-trimethoxylstyryl]cyclohex-1-ene (6) showed weak cytotoxicity against HepG2 cells with IC50 values of 122.9, 127.3, 257.5, and 168.5 µM, respectively.

Taxotrophises A and B, two new polyphenols from the stems of Taxotrophis ilicifolius.

From the EtOAc extract of the wood of the stems of Taxotrophis ilicifolius (Moraceae), two new secondary metabolites, named taxotrophises A (1) and B (2), were isolated, together with five known compounds (3-7). Their chemical structures have been elucidated by extensive NMR spectroscopic analysis. All isolated compounds have been evaluated for α-glucosidase inhibitory activity. In the present work, compounds 1 and 4 showed the strongest α-glucosidase inhibitory activity with IC50 values of 6.5 and 1.5 µM, respectively, and stronger than that of a positive control, acarbose (IC50; 214.5 µM).

A new 8,3'-neolignan from Solanum procumbens Lour.

The phytochemical investigation of the EtOAc-soluble fraction of the aerial parts of Solanum procumbens Lour. has been carried out to obtain seven compounds, including a new 8,3'-neolignan named solacanin A (1). Their chemical structures were elucidated based on the spectroscopic data interpretation. All isolated compounds were tested for their α-glucosidase inhibitory activity. Compounds 1 and 3-6 showed inhibitory activity with IC50 values of 221.5, 18.9, 6.0, 104.1, and 219.7 µM, respectively.[Formula: see text].

Two new derivatives of 8-prenyl-5,7-dihydroxycoumarin from the stems of Streblus ilicifolius (S.Vidal) Corn.

From the EtOAc-soluble extract of the stems of Streblus ilicifolius (Moraceae), two new secondary metabolites named strebluses A (1) and B (2) were isolated. Their chemical structures have been concluded based on the chemical derivatisation and the spectroscopic interpretation. All compounds have been tested for their tyrosinase inhibitory activity. They showed weaker inhibitory activity than that of kojic acid (IC50, 44.6 µM).[Formula: see text].

Strebluses E-H, four new stilbene-like derivatives from the stems of Streblus ilicifolius.

Following bioactivity-guided isolation, four new stilbene-like derivatives, named Strebluses E-H, were isolated from the EtOAc-soluble fraction of the stems of Streblus ilicifolius (Moraceae). Their chemical structures were elucidated based on NMR spectroscopic data interpretation and optical rotation calculation. Streblus E possesses potent tyrosinase inhibitory activity with an IC50 value of 0.1 µM. Oxy-tyrosinase has two bound Cu2+ ions and a peroxide group in the binding site, which has a role in the catalytic oxidation. Thus, a docking study of Streblus E with oxy-tyrosinase was performed to analyze the ligand-protein interactions. With in silico modelling, the S value and the ligand-protein interactions suggested that Streblus E showed lower binding affinity for oxy-tyrosinase than that of Streblus C.

A new lignan from the stems of Buchanania lucida Blume (Anacardiaceae).

From the EtOAc-soluble extract of the stems of Buchanania lucida, one new lignan, (+)-(8S,8'S)-5'-methoxy-4,4'-di-O-methylsecoisolariciresinol (1), together with five known compounds (2-6) were isolated. Their structures were elucidated on the basis of NMR spectroscopic interpretation. The absolute configuration of 1 was determined based on the Cotton effects in the ECD spectrum. In the tyrosinase inhibitory activity test, p-hydroxybenzoic acid (6) showed the strong effect, with an IC50 value of 9.35 µM.

A new flavanone derivative from the rhizomes of Boesenbergia pandurata.

From the methanolic extract of the rhizomes of Boesenbergia pandurata, a new flavanone derivative named (2R,7″S)-8-(1-phenyl-2-carboxyethyl)pinocembrin (1) and four known flavonoids (2-5) were isolated. Its absolute configuration was concluded by NMR and MS spectroscopic analysis, together with comparison between experimental and calculated ECD data. In turn, compound 1 exhibited strong cytotoxicity against the PANC-1 human pancreatic cancer cell line with a PC50 value of 6.4 µM under nutrient-deprived conditions, comparable with that of arctigenin (PC50, 0.83 µM).

Chemical Constituents of Mangifera indica and Their Antiausterity Activity against the PANC-1 Human Pancreatic Cancer Cell Line.

Human pancreatic cancer cell lines such as PANC-1 have an altered metabolism, enabiling them to tolerate and survive under extreme conditions of nutrient starvation. The search for candidates that inhibit their viability during nutrition starvation represents a novel antiausterity strategy in anticancer drug discovery. A methanol extract of the bark of Mangifera indica was found to inhibit the survival of PANC-1 human pancreatic cancer cells preferentially under nutrient-deprived conditions with a PC50 value of 15.5 µg/mL, without apparent toxicity, in normal nutrient-rich conditions. Chemical investigation on this bioactive extract led to the isolation of 19 compounds (1-19), including two new cycloartane-type triterpenes, mangiferolate A (1) and mangiferolate B (2). The structures of 1 and 2 were determined by NMR spectroscopic analysis. Among the isolated compounds, mangiferolate B (2) and isoambolic acid (12) exhibited potent preferential cytotoxicity against PANC-1 human pancreatic cancer cells under the nutrition-deprived condition with PC50 values of 11.0 and 4.8 µM, respectively.

α-Glucosidase inhibitors from the bark of Mangifera mekongensis.

BACKGROUND: Mangifera mekongensis (Anacardiaceae) is cultivated for its edible fruit and has been used in traditional Vietnamese medicine for its anti-aging properties and for treating diabetes, vermifuge, and dysentery. As part of a search for biologically active compounds with reduction of the rate of glucose absorption, a screening has been initiated to evaluate natural product extracts for the inhibition of enzyme α-glucosidase. A n-hexane extract of the bark of M. mekongensis showed strong α-glucosidase inhibitory activity with IC50 value of 1.71 µg/mL. Thus, the constituents of this plant were examined. RESULTS: Two new steroids named mekongsterol A (1) and mekongsterol B (2), were isolated from the n-hexane extract of the bark of M. mekongensis (Anacardiaceae), together with seven known compounds (3-9). Their chemical structures were elucidated on the basis of spectroscopic data. All compounds possessed significant α-glucosidase inhibitory activity in a concentration-dependent manner, except for 3 and 4. Compounds 1, 2, 5-9 showed more potent inhibitory activity, with IC50 values ranging from 1.2 to 112.0 µM, than that of a positive control acarbose (IC50, 214.5 µM). CONCLUSIONS: These results suggested that the traditional use of the bark of M. mekongensis for the treatment of diabetes diseases in Vietnam may be attributable to the α-glucosidase inhibitory activity of its steroid and cycloartane constituents.

α-Glucosidase inhibitors from the leaves of Embelia ribes.

A novel and rare 1,4-dehydrated ceramide, embelamide (1), and a new C-glycoalkaloid which is based on a ß-carboline ring system, 1-(2'-deoxy-α-d-ribopyranosyl)-ß-carboline (4), were isolated from the CHCl3 soluble fraction of the leaves of Embelia ribes (Myrsinaceae), together with thirteen known compounds (2-3, 5-15). Their structures were elucidated on the basis of spectroscopic data. Compounds 1, and 5-12 possessed significant α-glucosidase inhibitory activity in a concentration-dependent manner, and showed more potent inhibitory activity, with IC50 values ranging from 1.3 to 155.0 µM, than that of a positive control acarbose (IC50, 214.5 µM).