stilbenes and gigantol

In general, anti-inflammatory treatment is considered for multiple liver diseases despite the etiology. But current drugs for alleviating liver inflammation have defects, making it necessary to develop more potent and safer drugs for liver injury. In this study, we screened a series of (dihydro-)stilbene or (dihydro-)phenanthrene derivatives extracted from Pholidota chinensis for their potential biological activities. Among 31 compounds, the dihydro-stilbene gigantol exerted most potent protective effects on human hepatocytes against lithocholic acid toxicity, and exhibited solid antioxidative and anti-inflammatory effect in vitro. In mice with CCl

Topics: Administration, Oral; Animals; Anti-Inflammatory Agents; Antioxidants; Bibenzyls; Carbon Tetrachloride; Chemical and Drug Induced Liver Injury; Complement Membrane Attack Complex; Guaiacol; Hepatocytes; Humans; Inflammation; Lipid Peroxidation; Lithocholic Acid; Liver; Male; Mice, Inbred ICR; Oxidative Stress; Phenanthrenes; Proteome; Rats, Sprague-Dawley; Stilbenes

A new (propylphenyl)bibenzyl, bambusifolol (1), along with six known compounds, batatasin III (2), tristin (3), 3-hydroxy-5-methoxy bibenzyl (4), gigantol (5), 3',5-dimethoxy-9,9'-diacetyl-4,7'-epoxy-3,8'-bilign-7-ene-4'-methol (6) and balanophonin (7) were isolated from the whole plants of Eria bambusifolia. Their structures were elucidated by the means of extensive spectroscopic analysis. 3-7 were isolated from the genus Eria for the first time and 2 obtained originally from E. bambusifolia. All the compounds isolated were evaluated for their cytotoxicity against human tumour HL-60, SMMC-7721, A-549, MCF-7 and SW-480 cell lines, but none showed significant activity.

Topics: Antineoplastic Agents, Phytogenic; Bibenzyls; Cell Line, Tumor; Dendrobium; Guaiacol; Humans; Lignans; Stilbenes

Gigantol (1) and 3,7-dihydroxy-2,4-dimethoxyphenanthrene (2) from the orchid Scaphyglottis livida induced a significant concentration-dependent relaxation of the contractions evoked by noradrenaline (NA) in endothelium-intact and denuded rat aorta rings. Incubation with N(G)-nitro-L-arginine methyl ester (L-NAME, 1x10(-5) M) or methylene blue (MB, 1x10(-7) M) significantly reduced the relaxation induced by the stilbenoids 1 and 2. The results suggested that two or more mechanisms are involved in the vasorelaxant effects of both compounds.

Topics: Animals; Aorta; Bibenzyls; Guaiacol; Male; Medicine, Traditional; Orchidaceae; Phenanthrenes; Rats; Rats, Wistar; Sodium; Stilbenes; Vasodilation; Vasodilator Agents

A whole plant chloroform-methanol extract of the orchid Epidendrum rigidum inhibited radicle growth of Amaranthus hypochondriacus seedlings (IC50 = 300 microg/mL). Bioassay-guided fractionation furnished four phytotoxins, namely, gigantol (1), batatasin III (2), 2,3-dimethoxy-9,10-dihydrophenathrene-4,7-diol (9), and 3,4,9-trimethoxyphenanthrene-2,5-diol (11), along with the known flavonoids apigenin, vitexin, and isovetin and the triterterpenoids 24,24-dimethyl-9,19-cyclolanostane-25-en-3beta-ol (14) and 24-methyl-9,19-cyclolanostane-25-en-3beta-ol (15). Stilbenoids 1, 2, 9, and 11 inhibited radicle growth of A. hypochondriacus with IC50 values of 0.65, 0.1, 0.12, and 5.9 microM, respectively. Foliar application of gigantol (1) at 1 microM to 4 week old seedlings of A. hypochondriacus reduced shoot elongation by 69% and fresh weight accumulation by 54%. Bibenzyls 1 and 2, as well as synthetic analogues 4'-hydroxy-3,3',5-trimethoxybibenzyl (3), 3,3',4',5-tetramethoxybibenzyl (4), 3,4'-dihydroxy-5-methoxybibenzyl (5), 3'-O-methylbatatasin III (6), 3,3',5-trihydroxybibenzyl (7), and 3,4',5-trihydroxybibenzyl (8), were tested for phytotoxicity in axenic cultures of the small aquatic plant Lemna pausicostata. All bibenzyls derivatives except 7 and 8 inhibited growth and increased cellular leakage with IC50 values of 89.9-180 and 89.9-166 microM, respectively. The natural and synthetic bibenzyls showed marginal cytotoxicity on animal cells. The results suggest that orchid bibenzyls may be good lead compounds for the development of novel herbicidal agents.

Topics: Amaranthus; Araceae; Bibenzyls; Chemical Fractionation; Guaiacol; Herbicides; Orchidaceae; Plant Extracts; Seedlings; Stilbenes

A CH(2)Cl(2)-MeOH (1:1) extract prepared from the whole plant of Nidema boothii inhibited spontaneous contractions (IC(50) = 6.26 +/- 2.5 microg/mL) of the guinea-pig ileum. Bioassay-guided fractionation of the active extract led to the isolation of the novel spiro compound 1, which was given the trivial name nidemone, and the new dihydrophenanthrene 3, characterized as 1,5,7-trimethoxy-9,10-dihydrophenanthrene-2,6-diol. In addition, the known stilbenoids aloifol II (2), 1,5,7-trimethoxyphenanthrene-2,6-diol (4), ephemeranthoquinone (5), gigantol (6), ephemeranthol B (7), 2,4-dimethoxyphenanthrene-3,7-diol (8), lusianthridin (9), and batatasin III (10) were obtained. The isolates were characterized structurally by spectroscopic data interpretation. Compounds 2-6, 9, and 10 induced notable concentration-dependent inhibition of the spontaneous contractions of the guinea-pig ileum with IC(50) values that ranged between 0.14 and 2.36 microM. Bibenzyl analogues 23-35 were synthesized and tested pharmacologically. The results indicated that for maximum spasmolytic activity the bibenzyls should have oxygenated substituents on both aromatic rings; on the other hand, methylation of free hydroxyl groups as well as the increment of oxygenated groups in relation to compounds 6 and 10 decreased the smooth muscle relaxant activity. It was also demonstrated that bibenzyls 6 and 10 might exert their spasmolytic action not only by a nitrergic mechanism but also by inhibiting CaM-mediated processes.

Topics: Animals; Bibenzyls; Brain; Cattle; Dose-Response Relationship, Drug; Flavonoids; Guaiacol; Guinea Pigs; Ileum; Inhibitory Concentration 50; Mexico; Models, Biological; Molecular Conformation; Molecular Structure; Muscle Contraction; Orchidaceae; Parasympatholytics; Phosphoric Diester Hydrolases; Plants, Medicinal; Spiro Compounds; Stilbenes; Structure-Activity Relationship