Phenolic constituents of Cassia seeds and antibacterial effect of some naphthalenes and anthraquinones on methicillin-resistant Staphylococcus aureus.
Thirteen phenolic glycosides including six new compounds were isolated from seeds of Cassia tora (Leguminosae). The structures of the new compounds, rubrofusarin triglucoside (7), nor-rubrofusarin gentiobioside (9), demethylflavasperone gentiobioside (10), torachrysone gentiobioside (11), torachrysone tetraglucoside (12) and torachrysone apioglucoside (13), were elucidated on the basis of spectroscopic and chemical evidence. The effects of the phenolic glycosides, their aglycones and several other compounds structurally related to them on Escherichia coli K12, Pseudomonas aeruginosa PAO1 and some strains of Staphylococcus aureus were then examined. Among them, torachrysone (15), toralactone (16), aloe-emodin (18), rhein (19) and emodin (20) showed noticeable antibacterial effects on four strains of methicillin-resistant Staphylococcus aureus with a minimum inhibitory concentration of 2-64 micrograms/ml. On the other hand, the phenolic compounds tested did not show strong antibacterial effects on E. coli and P. aeruginosa.
Hatano
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T
Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Okayama University, Japan.
Uebayashi
H
H
Ito
H
H
Shiota
S
S
Tsuchiya
T
T
Yoshida
T
T
D000880:Anthraquinones / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification; D002240:Carbohydrate Sequence; D002366:Cassia / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D016106:Methicillin Resistance; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D009281:Naphthalenes / Q000737:chemistry / Q000494:pharmacology*; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D010946:Plants, Medicinal; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification; D012639:Seeds / Q000737:chemistry; D013211:Staphylococcus aureus / Q000187:drug effects*
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D000972:Antineoplastic Agents, Phytogenic; D009281:Naphthalenes; D010636:Phenols; D011753:Pyrones; C015497:rubrofusarin