Chuangxinmycin (CM) from Actinoplanes tsinanensis was an antibiotic discovered by Chinese scientists about 40 years ago. It contains a new heterocyclic system of indole fused with dihydrothiopyran, whose biosynthetic mechanism remains unclear. CM is used as an oral medicine in the treatment of bacterial infections in China. The simple structure makes CM as an attractive candidate of structure modification for improvement of antibacterial activity. Recently, we analyzed the secondary metabolites of Actinoplanes tsinanensis CPCC 200056, a CM producing strain, as a natural CM analogue. We discovered the first natural CM analogue 3-demethylchuangxinmycin (DCM) as a new natural product. Compared to CM, DCM exhibited a much weaker activity in the inhibition of the bacterial strains tested. The finding provides valuable information for the structure-activity relationship in the biosynthesis of CM.

Fifteen compounds were isolated from the stem (with skin removed) of Sinocalamus affinis by a combination of various chromatographic techniques including silica gel, macroporous adsorbent resin, Sephadex LH-20, and preparative HPLC. Their structures were elucidated by spectroscopic data as ( + )-(1S, 2R)-1, 2-bis (4-hydroxy- 3-methoxyphenyl)-1, 3-propanediol (1), threo-guaiacylglycerol-beta-O-4'-coniferyl ether(2), erythro-guaiacylglycerol-beta-O-4'-coniferyl ether(3), ( + )-(7S, 8R, 8'R)-5'-methoxylariciresinol(4), ( + )-(7S, 8R, 8'R)-5, 5'-dimethoxylariciresinol (5), ( +/- )-glaberide I (6), ( - )-syringaresinol (7), ( - )-medioresinol(8), ( - )-(8R, 8R')-4, 4'-dihydroxy-3, 3', 5, 5'-tetramethoxyligna-9, 9'-diol(9), ( - )-secoisolariciresinol-9, 9'-acetonide (10), and ( + )-lyoniresinol (11); a new natural product 2, 6-dimethoxypyran4-one (12), and beta-sitosterol, 4-hydroxycinnamic acid, and 2, 6-dimethoxy-p-benzoquinone. These compounds were isolated from the genus Sinocalamus for the first time, compound 10 should be an artifact.
Chromatography ; methods ; Drugs, Chinese Herbal ; chemistry ; Lignans ; chemistry ; isolation & purification ; Medicine, Chinese Traditional ; Plant Stems ; chemistry ; Poaceae ; chemistry

Two new compounds (1 and 2), together with twenty-one known compounds (3-23), were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, MCI gel, silica gel, and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified by spectroscopic data analysis as 4-hydroxy-3-(4-hydroxybenzyl) benzyl methyl ether (1), 4-( methoxymethyl) phenyl-1-O-beta-D-glucopyranoside (2), hibicutaiwanin (3), 4-(4-hydroxybenzyl)-2-methoxyphenol (4), 4,4'-methylenebis(2-methoxyphenol) (5), L-phenyllactic acid (6) ,4-hydroxy-3-methoxybenzyl ethol ether (7), p-hydroxylbenzyl alcohol (8), p-hydroxylbenzyl methyl ether (9), p-hydroxylbenzyl ethyl ether (10), p-hydroxybenzaldehyde (11), p-hydroxybenzoic acid (12), p-hydroxybenzoic acid (13), gastrodin (14), 4-(ethoxymethyl) phenyl-1-O-beta-D-glucopyranoside (15), 4-(beta-D-glucopyranosyloxy) benzaldehyde (16), p-methylphenyl-1-O-beta-D-glucopyranoside (17 ), methyl-O-beta-D-glucopyranoside (18), 5-hydroxymethl-furan aldehyde (19), parishin (20), parishin B (21), parishin C (22), and diosgenin (23). The 13C-NMR data of compound 4 was first reported.
Drugs, Chinese Herbal ; chemistry ; Gastrodia ; chemistry ; Organic Chemicals ; analysis ; isolation & purification ; Water ; chemistry