Anti-Inflammatory Spirostanol and Furostanol Saponins from Solanum macaonense.

Eight new spirostanol saponins, macaosides A-H (1-8), and 10 new furostanol saponins, macaosides I-R (9-18), together with six known spirostanol compounds (19-24) were isolated from Solanum macaonense. The structures of the new compounds were determined from their spectroscopic data, and the compounds were tested for in vitro antineutrophilic inflammatory activity. It was found that both immediate inflammation responses including superoxide anion generation and elastase release were significantly inhibited by treatment with compounds 20, 21, and 24 (superoxide anion generation: IC50 7.

Anti-neutrophilic inflammatory steroidal glycosides from Solanum torvum.

Torvpregnanosides A and B, two pregnane glycosides, and torvoside Q, a 23-keto-spirostanol glycoside, along with twelve known steroidal saponins were isolated from aerial parts of Solanum torvum. Of the latter, four of the 23-hydroxy-spirostanol glycosides, and, a yamogenin glycoside, were in this plant discovered. All structures were identified from spectroscopic data, and all the compounds were tested for in vitro anti-neutrophilic inflammatory activity.

Spirostanoids with 1,4-dien-3-one or 3β,7α-diol-5,6-ene moieties from Solanum violaceum.

Bioassay-guided fractionation of the CHCl3 layer of Solanum violaceum areal parts methanolic extract led to the isolation of four new steroidal sapogenins, indiosides L-O (1-4), along with eight known steroids, one lignin, and a coumarin. Indioside L is a rare spirostanoid possessing a 1,4-dien-3-one moiety in ring A. Moreover, compounds 3 and 4 represent rare examples of spirostene with the 3β,7α-diol-5,6-ene moiety compared to the normal 3β,7β-diol-5,6-ene derivatives.

Anti-human coronavirus (anti-HCoV) triterpenoids from the leaves of Euphorbia neriifolia.

Euphorbia neriifolia L. is a spiny herb native to Southeast Asia and currently cultivated in southern Taiwan. From the ethanolic extract of E.

Synthesis of chalcone derivatives as potential anti-diabetic agents.

Chalcones bearing electron donating or electron withdrawing substitutions were prepared and their glucose uptake activity was evaluated. Chalcone derivatives were synthesized in one step protocol with high purity and yield. Chalcones with chloro, bromo, iodo and hydroxy substitutions at position 2 on A-ring exhibited the highest activity with glucose medium concentration (210 to 236 mg/dl) compared to pioglitazone and rosiglitazone (230 and 263 mg/dl, respectively).

Design and synthesis of gambogic acid analogs as potent cytotoxic and anti-inflammatory agents.

Prenyl- and pyrano-xanthones derived from 1,3,6-trihydroxy-9H-xanthen-9-one, a basic backbone of gambogic acid (GA), were synthesized and evaluated for in vitro cytotoxic effects against four human cancer cell lines (KB, KBvin, A549, and DU-145) and anti-inflammatory activity toward superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, prenylxanthones 7-13 were generally less active than pyranoxanthones 14-21 in both anticancer and anti-inflammatory assays. Furthermore, two angular 3,3-dimethypyranoxanthones (16 and 20) showed the greatest and selective activity against the KBvin multidrug resistant (MDR) cell line with IC(50) values of 0.

Indiosides G-K: steroidal glycosides with cytotoxic and anti-inflammatory activities from Solanum violaceum.

Five new steroidal glycosides (1-5) and nine known compounds were isolated from Solanum violaceum. Indiosides G (1) and H (2) are spirostene saponins with an iso-type F ring, indioside I (3) is a spirostane saponin, and indiosides J (4) and K (5) are unusual furostanol saponins with a deformed F ring. These structures represent rare naturally occurring steroidal skeletons.

Cytotoxic N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides: structure-activity relationships and synergistic studies.

The synthesis and cytotoxic evaluation of a series of Fmoc-based dipeptides are described. Among the thirty compounds, 4a, 8a, 12a, 2b, 4b, 10b, 3c, 4c and 6c showed potent activity against HepG2, Hep3B, MCF-7, MDA-MB-231, A549 and Ca9-22 human cancer cell lines. The most active compounds (10a and 10c) showed relatively good sensitivity toward HepG2 and Ca9-22 cell lines with IC50 values of 1.

Antitumor agents. 271: total synthesis and evaluation of brazilein and analogs as anti-inflammatory and cytotoxic agents.

The first total synthesis of the naturally occurring tetracyclic homoisoflavonoid brazilein (1) and 14 new analogs (1a-n) is reported. Target compounds and intermediates were assayed for anti-inflammatory effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB, and for cytotoxic activity against nasopharyngeal (KB), vincristine-resistant nasopharyngeal (KBvin), lung (A549) and prostate (DU-145) human cancer cell lines. The most active compound 1b showed potent effects on superoxide anion generation and elastase release with IC(50) values of 1.

Flavonol glycosides from Muehlenbeckia platyclada and their anti-inflammatory activity.

A new flavonol, morin-3-O-alpha-rhamnopyranoside (1), along with four known flavonols, kaempferol 3-O-alpha-rhamnopyranoside (2), kaempferol 3-O-beta-glucopyranoside (3), quercetin 3-O-alpha-rhamnopyranoside (4) and (+)-catechin (5), were isolated from the methanolic extract of Muehlenbeckia platyclada. The structures of these compounds were determined on the basis of chemical and spectroscopic evidence, as well as acid hydrolysis of the original glycoside. Isolates were evaluated for inhibition of generation of superoxide anion, and inhibition of release of neutrophil elastase.

Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents.

Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9, 12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC(50) values of 0.

Bioactive cembrane diterpenoids of Anisomeles indica.

Five new cembrane-type diterpenoids with a trans-fused alpha-methylene-gamma-lactone (1-5), a new flavonoid glucoside (6), and 17 known compounds were isolated from a methanol extract of Anisomeles indica. The structures of 1-6 were elucidated by spectroscopic analysis, and the absolute configuration of compound 1 was determined using the modified Mosher's method. Compound 8 (4,5-epoxovatodiolide) exhibited cytotoxicity against a small panel of human cancer cell lines.