Coelonin

Phenolic compounds from the stems of Flickingeria fimbriata.[Pubmed:28278646]

Nat Prod Res. 2017 Jul;31(13):1518-1522.

Chemical investigation of Flickingeria fimbriata (Bl.) Hawkes (Orchidaceae) resulted in the isolation and identification of one new dihydrophenanthrene, 1,2,5,6,7-pentamethoxy-9,10-dihydrophenanthrene (1), together with seven known dihydrophenanthrenes, erianthridin (2), Coelonin (3), 4-methoxy-9,10-dihydrophenanthrene-1,2,7-triol (4), lusianthridin (5), ephemeranthol A (6), flavanthridin (7) and hircinol (8), four known phenanthrenes, epheranthol B (9), nudol (10), denthyrsinin (11) and confusarin (12), and one known bibenzyl, batatasin III (13). The structure of the new compound was elucidated by spectroscopic analysis (HRMS, 1D and 2D NMR). All the compounds were isolated from F. fimbriata for the first time except for compounds 5 and 12, and compounds 1, 3, 4, 8, 10, 11 and 13 were obtained from this genus for the first time. Compounds 1-4 showed moderate cytotoxic activity against HepG2 cells.

Phenanthrenes from Arundina graminifolia and in vitro evaluation of their antibacterial and anti-haemolytic properties.[Pubmed:28553728]

Nat Prod Res. 2018 Mar;32(6):707-710.

Chemical investigation and activity test of Arundina graminifolia led to the isolation of six phenanthrenes: blestriarene A (1), shancidin (2), densiflorol B (3), ephemeranthoquinone (4), Coelonin (5) and lusianthridin (6). The isolated compounds demonstrated antibacterial and anti-haemolytic activities. It was found that compounds 1 and 2 had medium antibacterial activity against Staphylococcus aureus, Bacillus subtilis and Escherichia coli, with MICs of 20-40 mug/mL and MBCs of 40-320 mug/mL. Bactericidal mechanisms were explored. Rupture of cell wall and membrane and leakage of nuclear mass were observed by transmission electron microscopy (TEM). Moreover, compounds 1-3 attenuated the erythrocyte damage. Compounds 1 and 2 showed significant anti-haemolytic activity with inhibition rate about 50% at 16 mug/mL.

[Chemical constituents of Osmanthus fragrans].[Pubmed:26137690]

Zhongguo Zhong Yao Za Zhi. 2015 Feb;40(4):679-85.

By Silica gel, Sephadex LH-20 and other materials for isolation and purification and by physicochemical methods and spectral analysis for structural identification, 32 compounds were isolated and identified from ethyl acetate portion of alcohol extract of the Osmanthus fragrans. Their structures were identified as boschniakinic acid (1), ursolaldehyde (2), augustic acid (3), arjunolic acid (4), 5-hydroxymethyl-2-furancarboxaldehyde (5), isoscutellarein (6), 6, 7-dihydroxycoumarin (7), 2alpha-hydroxy-oleanolic acid (8), quercetin-3-0-beta-D-glu-copyranoside (9), D-allito (10), 5, 4'-dihydroxy-7- methoxyflavone-3-0-beta-D-glucopyranoside (11), 5,7-dihydroxychromone (12), lupeol (13), naringenin (14), acetyloleanolic acid (15), chlorogenic acid (16), kaempferol-3-0-beta- D-glucopyranoside (17), oleanolic acid (18), kaempferol-3-0-beta-D-galactopyanoside (19), 3', 7-dihydroxy-4'-methoxyisoflavon (20), ergosta-4,6,8 (14), 22-tetraen-3-one (21), p-hydroxycinnamic acid (22), syringaresinol (23), 3,4-dihydroxyacetophenonel (24), beta-sitosterol (25), ethyl p-hydroxyphenylacetate (26), benzoic acid (27), caffeic acid (28), Coelonin (29), p-hydorxy-phenylacetic acid (30), p-hydroxyacetophenone (31), and methyl-p-hydroxphenylacetate (32). Except for compounds 2, 4, 5, 8-11, 13, 15, 18, 20, 25, and 27, the rest were isolated from the Osmanthus fragrans for the first time.

Separation and purification of 9,10-dihydrophenanthrenes and bibenzyls from Pholidota chinensis by high-speed countercurrent chromatography.[Pubmed:25421716]

J Sep Sci. 2015 Feb;38(3):453-9.

Stilbenoids are the main components of leaves and stems of Pholidota chinensis. In the present investigation, high-speed counter-current chromatography was used for the separation and purification of two classes of stilbenoids, namely, bibenzyls and 9,10-dihydrophenanthrenes, on a preparative scale from whole plants of P. chinensis with different solvent systems after silica gel column chromatography fractionation. n-Hexane/ethyl acetate/methanol/water (1.2:1:1:0.8, v/v/v/v) was selected as the optimum solvent system to purify 1-(3,4,5-trimethoxyphenyl)-1',2'-ethanediol (1), Coelonin (2), 3,4'-dihydroxy-5,5'-dimethoxybibenzyl (3), and 2,7-dihydroxy-3,4,6-trimethoxy-9,10-dihydrophenanthrene (4). While 2,7-dihydroxy-3,4,6-trimethoxy-9,10-dihydrophenanthrene (5), batatasin III (6), orchinol (7), and 3'-O-methylbatatasin III (8) were purified by n-hexane/ethyl acetate/methanol/water (1.6:0.8:1.2:0.4, v/v/v/v). After the high-speed counter-current chromatography isolation procedure, the purity of all compounds was over 94% assayed by ultra high performance liquid chromatography. The chemical structure identification of all compounds was carried out by mass spectrometry and (1)H and (13)C NMR spectroscopy. To the best of our knowledge, the current investigation is the first study for the separation and purification of bibenzyls and 9,10-dihydrophenanthrenes by high-speed counter-current chromatography from natural resources.