Studies On The Chemical Constituents Of Polytrichum Commune, Conoscyphus Trapezioides And Dracocephalum Peregrinum

Two bryophytes, Polytrichum commune and Conoscyphus trapezioides and the medicinal plant Dracocephalum peregrinum were phytochemically investigated in this paper. A total of 60 compounds were obtained and their structures were determined on the basis of extensive chemical and spectroscopic means. Two novel flavonones coupled with styryls, FP-DJFX-1~2, together with 8 new compounds were identified. FP-DJFX-1~2 could hypothetically be derived from the coupling of stilbenes with Z- and E-cinnamic acids, respectively.1. Studies on the Chemical Constituents of Polytrichum commune and Conoscypphus trapezioidesThe bryophyta, which comprise more than 24,000 species worldwide, are taxonomically placed between algae and pteridophytes. Collectively, they represent several quite separate evolutionary lines and are classified into three coordinate phyla: liverworts, mosses and hornworts. Bryophytes have been widely used as medicinal plants for the treatment of external injury, adustum, empyrosis, infection, pulmonary tuberculosis, neurastheria convulsion. And they are composed of various types of secondary metabolite which show significant biological activities.In this paper, Polytrichum commune L.ex Hedw. and Conoscypphus trapezioides (Sande Lac.) Schiffn. were phytochemically investigated. A total of 30 compounds were obtained and 22 of them were determined on the basis of spectral analysis: FP-DJFX-1: Communin A, FP-DJFX-2: Communin B, FP-DJFX-3: Ohioensin H, FP-DJFX-4: ?-sitosterol, FP-DJFX-5: 7αhydroxylsitosterol,FP-DJFX-6: ergosterol, FP-DJFX-7: methylindoline -6-carboxylate, FP-DJFX-8: 4-hydroxybenzoic acid, FP-DJFX-9: 4- hydroxy-2-methoxybenzoic acid, FP-DJFX-10:5-hydroxy-7-methoxy-4H- chromen-4-one, FP-DJFX-11 : 5-hydroxy-6-methoxy-7-O-β-D-glucosyl coumarin, FP-DJFX-12:sucrose, FP-DJFX-13:?-D-furanallulose,FP- DJFX-14 :β-D-uranallulose, FP-DJFX-15 : 3,6,9,12,15,18,21,24,27,30- decaoxadotriacontane-1,32-diol. FP-HET-1: Trapezioidesin A, FP-HET-2: Trapezioidesin B, FP-HET-3: (E)-2-(3,7-dimethylocta-2,6-dienyl)-4- methoxyphenol, FP-HET-4: (E)-3-(3,7-dimethylocta-2,6-dienyl)-4- methoxyphenol, FP-HET-5: betulinic acid, FP-HET-6: oleanolic acid, FP-HET-7: 1,8,15,22,29,36-hexaazacyclodotetracontane-2,9,16,23,30,37- hexaone.Among them, FP-DJFX-1~3 and FP-HET-1, 2 are five new compounds, FP-HET-7 is a new natural products and FP-DJFX-5~15 and FP-HET-1~7 were isolated from these plants for the first time. FP-DJFX-1~3 might be derived from cinnamic acid and 3,5-dioxohexanoice acid via different pathways. FP-DJFX-1 and FP-DJFX-2 apparently arised from the coupling of stilbenes with Z- or E-cinnamic acids, respectively. FP-DJFX-2 and FP-DJFX-3 exhibited cytotoxicity against A-549 lung carcinoma, LOVO bowel carcinoma, MDA-MB-435 breast adenocarcinoma, HepG2 hepatoma carcinoma and 6T-CEM T cell leukemia cell lines. However, FP-DJFX-1, the isomer to FP-DJFX-2, showed no cytotoxicity in the cytotoxic assay. This implied that the Z-geometry double bond in FP-DJFX-2 played an important role in the cytotoxicity against these human tumor cell lines.2. Studies on the Chemical Constituents of Dracocephalum peregrinum Dracocephalum peregrinum, Labiatae, likes growing in the crack of stones on alpine steppe. which usually grows 15~25 cm high and flowers from June to August, distributes in northwest of the Xin Jiang Province in China.Genus Dracocephalum was an important member of the Labiatae family. Several species of Dracocephalum were used in Traditional Chinese Medicine. Chemical investigation on these species resulted in the isolation of flavanoids, terpenoids, cinnamic acid derivatives and volatile oils, but very few chemical and pharmacological study was reported on Dacocephalum peregrinum until now.In our further phytochemical investigation on Dracocephalum peregrinum, 40 compounds were isolated and 38 of them were identified by spectral analysis: FP-CCZZH-1: Peregrinumin A, FP-CCZZH-2: Peregrinumin B, FP-CCZZH-3: Peregrinumin C, FP-CCZZH-4: Peregrinumcin A, FP-CCZZH-5: Peregrinumin D, FP-CCZZH-6: luteolin, FP-CCZZH-7: 5,7,3'-trihydroxyl-4'-methoxylflavone, FP-CCZZH-8: kaempferol, FP-CCZ ZH-9: acacetin, FP-CCZZH-10: 5,3',4'-trihydroxyl-3, 7-dimethoxylflavone, FP-CCZZH-11: 5-hydroxyl-3',4',6,7-tetramethoxyl flavone, FP-CCZZH -12: kaempferol-7-O-β-D-glucoside, FP-CCZZH-13: acacetin-7-O-β-D-glucoside, FP-CCZZH-14: 5,6,7,4'-tetrahydroxylflavone -7-O-β-D-glucoside, FP-CCZZH-15: isoquercitrin, FP-CCZZH-16: quercitrin, FP-CCZZH-17: 3,5,7-trihydroxyl-4'-methoxylflavone-3-O-?-L- rhamnoside, FP-CCZZH-18: 5,7-dihydroxyl-4'-methoxyl flavone-7-O-?-L- rhamnosyl(1?6)-?-D-glucoside, FP-CCZZH-19: caffeic acid, FP-CCZZH- 20: methyl caffeate, FP-CCZZH-21: ferulic acid, FP-CCZZH-22: trans-P- hydroxycinnamic acid, FP-CCZZH-23: caffeotannic acid, FP-CCZZH-24: 3-hydroxybenzoic Acid , FP-CCZZH-25: 3,4-dihydroxybenzoic Acid, FP- CCZZH-26: 4-hydroxy-3-methoxy benzaldehyde, FP-CCZZH-27: P- hydroxybenzcic acid glucoside, FP-CCZZH-28: benzene-β-D-glucoside, FP- CCZZH-29: 2R-prunasin, FP-CCZZH-30: 3-carbonylursolic acid, FP- CCZZH-31: ursolic acid, FP-CCZZH-32: oleanolic acid, FP-CCZZH-33: lupeol, FP-CCZZH-34: betulinic acid, FP-CCZZH-35: betulin, FP- CCZZH-36: carotene, FP-CCZZH-37: daucosterol, FP-CCZZH-38: stigmasterol.Among them, FP-CCZZH-1~5 are five new compounds and FP-CCZZH-12, 13, 19, 20, 22, 25, 29, 30, 31, 32 were isolated from this plants for the first time.FP-CCZZH-1~4 were tested for effects on NO and NF-?B activity. Among the compounds tested, FP-CCZZH-1~4 showed good inhibitory activities on NO production induced by LPS at dose of 100 ?g/ml. But only FP-CCZZH-2 and 3 showed weak effects on NF-?B activity at dose of 100 ?g/ml.