| Yanning granula consists of Monochasma savatieri Franch、Commelina communis L.and Hedyotis diffusa Willd.(2:1:1), which has been listed in the Catalogue of National Protected TCM Medicines, clinically used for the treatment of upper respiratory tract infection, tonsillitis, urinary tract infection, acute dysentery, enteritis and other inflammatory diseases.In order to get some information for the further R&D clinical application, the chemical constituents and their antibacterial and anti-inflammatory activities were investigated systematically.Using the filter paper method to study the antibacterial activity in vitro of Yanning granula extracted in different ways, and using croton oil and paraxylene induced mouse ear edema acute inflammation models to study their anti-inflammatory effects, the30%EtOH fraction eluted by Diaion AB-8column of Yanning granula was confirmed as the active site.Guided by active tracking method, forty compounds were isolated by chromatography on silica gel, Sephadex LH-20gel columns, and reverse phase Semi-preparation HPLC repeatedly from the active fraction of Yanning granula, and their structures were identified by spectroscopic analysis (NMR and MS). These isolates were identified to be savatiside A、B、C、D、E、F、G、H (1-8), isoacteoside (9), cistanoside D (10), epimeridinoside A (11), Parvifloroside B (12), Torenoside-B (13), acteoside (14), osmanthuside B (15),(7S,8R)dehydrodiconiferyl alcohol9’-β-glucopyranoside (16),(+)-isolariciresinol (17),5-methoxy-(+)-isolariciresinol (18),(-)-secoisolariciresinol (19),7,7’-dihydrosecoisolariciresinol (20),7-hydroisolariciresinol (21),8-O-Acetylmussaenoside (22),8-O-Acetylmussaenosidic acid (23), Nepetanudoside B (24),7-O-acetylloganic acid (25), Methyl9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoeate (26),9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoic acid (27), Methyl9,12,13-trihydroxyoctadeca-10(E)-enoeate (28),9,12,13-trihydroxyoctadeca-10(E)-enoic acid (29), Methyl8,11,12-trihydroxyoctadeca-9(E)-enoeate (30),p-hydroxy cinnamic acid (31), isoferulic acid (32), Vanillic acid (33), Oleanolic acid (34), Apigenin (35), Luteolin (36), Quercetin (37), Rutin (38), Kaempferol (39),4-hydroxy-l-methoxyanthraquinone (40).Among them, compounds1-8were new compounds, and compounds7and8have a rare skeleton of bis-iridoid glycoside with a carbohydrate chain located at C-3. Moreover, all of the12phenylethanoid glycosides isolated were evaluated for anticomplement activities using an in vitro assay of the complement system of the classical pathway, and all the compounds were proved to be capable of inhibiting complement activity with IC50value of95-135μM. Preliminary analysis of the structure-activity relationship from these natural phenyethanoid glycosides revealed that compounds with a hydroxy group at C-a (1,2,3,4,5and11) had a slightly decreased anticomplement activity. |
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