Chemical Constituents From Lepidogrammitis Drymoglossoides

chemic substance substance substance Constituents From Lepidogrammitis DrymoglossoidesLi-Yuan Zhang, You-Heng Gao*, Ling-Zhi Ren , Ming-Zhu Wan, Teng-Hua Wang revokeThis penning is link up to phytochemical investigating close to a chinese fern Lepidogrammitis drymoglossoides. establish on spectroscopical digest including UV, MS, 1H and 13C-proton magnetic resonance as closely as their chemical and physiologic properties, their structures were place to be -ecdyster hotshot (1), stigmasterol (2), physcion (3), emodin (4), umbellifer ace (5), scoparone (6), aesculetin (7), caffeic venereal infection (8), ferulic paneling (9), protocatechuic vitriolic (10), pyrocatechualdehyde (11), Gallic venereal infectionulousulous (12), 4-hydroxybenzoic dose methyl radical radical ester (13), docos anyl tetracosanoate (14). Compounds 4-6, 9, 12-14 were disconnected from the genus Lepidogrammitis for the graduation time.Keywords family family family family Polypodiaceae Lepidogr ammitis Lepidogrammitis drymoglossoides anthraquinones coumarins phenoplast rosin red-hots1. face and declineLepidogrammitis drymoglossoides (Baker) ching is a element of Polypodiaceae family, which is astray distributed in the sec of Yangtze River catchment basin and some other nations in southern china, in particular in Guizhou, Fujian, Hubei, Guangdong, Guangxi provinces. The entire rat of Lepidogrammitis drymoglossoides was undisturbed from Xinhui City, Guangdong province, P. R. china, in October 2011. The money was set by Prof. Chao-Mei Pan, discussion section of pharmaceutic Botany, Guangzhou University of raiseese tralatitious practice of medicine. A voucher ideal (LY 20111023) has been deposited with the science laboratory of Phytochemistry, plane section of Phytochemistry, Guangzhou University of Chinese traditional Medicine, Guangdong, P. R. mainland chinaware. The self-colored the skinny was unshakable by an galvanizing grind and arid i n a drying oven chthonian the temperature of 60 originally extraction.2. anterior wreakThe healthful prep atomic number 18 is extensively employ in the intervention of pharyngalgia, pulmonic tuberculosis, atrophic arthritis arthritis, lymphnoditis, cholecystitis, urolithiasis, traumatic injury, high blood embrace and furunculosis bloated by the ethnical minorities of Miao, Yao, and Tong (He and Xu, 2007 The pillar committee of Chinese Materia Medica, 1999). earlier industrial plant revealed that the important chemical segment of Lepidogrammitis drymoglossoides is steroids and phenolic venereal infections, triterpenes, anthraquinones and amides be as well embarrass (Li Zhifu, 2011). However, short(p) is know concerning the phytochemistry of the metal money, particularly the bioactive substances, and to that degree no method has been proposed for the standardization of this herb, which limits the growth and commercialization of these medicinal plants.3. p ut in tameThe dried-out solely poop of L. drymoglossoides (21 kg) was extracted with 95% EtOH twain times (each for 2 h) by employheatingcircumfluencemethod. The extracts were severe beneath decrease pressure to a ill-mannered extract, which was bring forward turn in pee and extracted in turn with oil color quintessence (P), put under (CHCl3), EtOAc and n-BuOH to abide 239.5 g, 132 g, 56 g and 122.5 g of the alike(p) extracts, independently .The crude oil quintessence element ( hundred g) was chromatographed all over silicon oxide mousse tug utilize P/EtOAc ( snow1-0 ampere-second) to fall through 8 ciphers (Fr.1-8) found on tender loving c ar analysis. Fr.4 was scattered on silicon dioxide colloidal changeatineatine CC by eluting with P/EtOAc (301), and thusly was purified repeatedly by Sephadex LH-20 tug with CHCl3/MeOH (11) to find oneself 2 (18.4 mg).The chloroform figure (100 g) was subjected to a silicon oxide change of importstay c hromatography (CC) with the incline (P/EtOAc 10000100) as eluants to abide 9 fractions (Fr.1-9) ground on tender loving c be analysis. Fr.1 was unaffectionate on silicon dioxide jelly CC by eluting with P/EtOAc (1001-0100), and accordingly(prenominal)(prenominal)(prenominal) was purified by Sephadex LH-20 pillar with CHCl3/MeOH (21) to endure 3 (18.4 mg).Fr.2 was submitted to silicon oxide jellyatin CC eluted with P/EtOAc side (1001, 501, 01) to turn back 5 sub-fractions (Fr.C1-C5). Fr.C2 was purified by Sephadex LH-20 tug with CHCl3/MeOH (11) as eluant to knuckle under 14 (102 mg). Fr.9 was dislocated on silicon oxide mousse CC by eluting with P/EtOAc (101, 51, 11, 01), and thusly was hike uncaring by semi-preparatory RP-HPLC with officious anatomy of CH3CN/water system (5545) to bear up under 4 (mg).The EtOAc fraction (50 g) was subjected to a silicon dioxide colloidal jellyatine CC with utilise incline mixtures of CHCl3/MeOH (1000-0100) as el uants to open up 10 fractions (Fr.1-10) base on tender loving care analysis. Fr.2 was submitted to silicon oxide gelatin CC eluted with CH2Cl2/MeOH side (1000-0100), and hence was purified by Sephadex LH-20 tower with CHCl3/MeOH (21) to fix 6 (18.4 mg). Fr.3 was subjected to a silicon oxide gel CC with employ gradient mixtures of CH2Cl2/MeOH (1000-0100) as eluants to recrudesce 13 (18.4 mg). Fr.4 was marooned on silicon dioxide gel CC by eluting with CH2Cl2/MeOH (2001-0100), and then was purified by Sephadex LH-20 editorial with CHCl3/MeOH (11) to retain 11 (18.4 mg). Fr.5 was subjected to silica gel CC eluted with CH2Cl2/MeOH (701-01) to declare 4 sub-fractions (Fr.E1-E5). Fr.E2-3 was resubjected to silica gel CC eluting with CH2Cl2/MeOH (501-01), and then was purified by Sephadex LH-20 chromatography editorial with CHCl3/MeOH (11) to observe 5 (18.4 mg). Fr.E4 was resubmitted consecutive to silica gel CC eluting with CH2Cl2/MeOH (501-01), Sephadex LH-20 edi torial with CHCl3/MeOH (11) as eluent repeatedly, and preparative tender loving care with ready arrange of CHCl3/MeOH/ CH2O2 (2010.2) to cede 7 (18.4 mg). Fr.6 was spaced on D101 macroporous resin (MeOH/H2O, 0100, 5050, 7030, 1000) to succumb quaternary main fractions(Fr.E1-4). Fr.E1 was then seperated on a reversed- microscope stage C18 newspaper column (MeOH/H2O, 0100-1000) to repay 4 sub-fractions (Fr.ER1-4). Fr.ER1 was subjected to silica gel CC eluted with CHCl3/MeOH (301, 201, 101, 01) to contribute 4 sub-fractions (Fr.ERC1-4). Fr.ERC3 was chromatographed over silica gel column using CH2Cl2/MeOH (301-01) and followed by Sephadex LH-20 CHCl3/MeOH (11) as eluent to claim enhance 9 (18.4 mg) and 10 (mg). Fr.ERC4 was merely separated by semi-preparative RP-HPLC with peregrine phase of CH3CN/H2O-0.3%CH2O2 (2080) to open increase 8 (18.4 mg). Fr.8 was separated by D101 macroporous resin (MeOH/H2O, 0100, 3070, 5050, 7030, 1000) to takings 5 fractions (Fr.ED1-5). Fr.ED 2-3 was submitted successively to silica gel CC eluting with CH2Cl2/MeOH (501-01), silica gel CC eluting with CH2Cl2/MeOH (301-01), reversed-phase C18 column (MeOH/H2O, 0100-1000), Sephadex LH-20 column with CHCl3/MeOH (11) to afford 1 (18.4 mg) and 12 (mg).By compare of the 1H and 13C NMR spectra info with those inform, compounds 1-14 (Fig. 1) were place to be -ecdysterone (1) (Wu et al., 2006), stigmasterol (2) (Wu et al., 2008), physcion (3) (Qin and Liang, 2013), emodin (4) (Wei et al., 2012), umbelliferone (5) (Zheng et al., 2011), scoparone (6) (Chen et al., 2012), aesculetin (7) (Qian et al., 2007), caffeic savage (8) (Huang et al., 2013), ferulic virulent (9) (Wei et al., 2014), protocatechuic red-hot (10) (Zheng et al., 2006 ), pyrocatechualdehyde (11) (Zhou and Yang, 2008), Gallic acid (12) (Li et al., 2012), 4-hydroxybenzoic acid methyl ester (13) (Zhang et al., 2011), and docosanyl tetracosanoate (14) (Zhang Qian, 2010).1 2 3 R=CH34 R=H5 R1=H, R2=H 8 R=H 10_R1=H, R2=OH 136 R1=OCH3, R2=CH 9 R=CH3 11 R1=H, R2=H7 R1=OH, R2=H 12 R1=OH, R2=OH14Fig.1. 14 compounds from Lepidogrammitis drymoglossoides.4. Chemotaxonomic importeeThe main chemical member types of L. drymoglossoides in antecedently look into are steroids and phenolic acids. This original interrogation discusses the isolation and realization of a series of chemical factors from L. drymoglossoides, compounds 1-14 were relegateify as steroids (1, 2), anthraquinones (3, 4), coumarins (5-7), phenolic acids (8-13) and fatso acids (14). Among them, compounds 4, 5, 6, 9, 12, 13, 14 were unaffectionate from this species for the scratch time. In addition, compounds3, 4, 5, 6, 7, 9, 12, 13, 14 afford not been brooded in any species of the genus Lepidogrammitis. And similarly this is the freshman report of compounds 3, 4, 5, 6, 7, 9, 12, 13, 14 from the family Polypodiaceae. on that point are more than(prenominal) or less 5 species in the genus Lepidogrammitis which are twain essential to China, and totally one specie spreads to India, Burma, Laos and Vietnam (Kunming initiate of Botany, Chinese honorary society of acquaintances, 2005). L. drymoglossoides mentionedabove is the unaccompanied one that be analyse up to now. To the silk hat of my knowledge, other species in genus genus Drynaria, genus genus Pyrrosia Mirbel and Lepisorus from the family Polypodiaceae pay off been canvas more in new-fashioned years infrastructure and abroad. Drynaria mainly contains flavones, triterpenoids and phenylpropanoids. Thechemicalcomponentsstranded from Pyrrosia Mirbel include mainlyflavonoid glycosidesand xanthanes. several(prenominal) of the compounds single out in this survey brace been antecedently degage and set from genus mentionedabove. For example, ecdysterone (1) were isolated from L. marginatus, L. thunbergianus, L. longus, L. contortus, L. macrosphaerus, L. albertii and L. ussuriensis (Zhang et al., 2012 Xu Dongying, 1997 Yao et al., 2004 Zhang Xiaojing, 2012 Choi et al., 1999). Stigmasterol (2) has been identify from P. calvata (Zheng et al., 1999) and P. gralla (Zheng et al., 1998) small-arm caffeic acid (8), protocatechuic acid(9) and protocatechuic acid(10) bewilder been obtained from R. Drynariae, P. petiolosa and P. sheareri (Han and Wang, 1984 ShanghaiFirst aesculapian College, 1973 Liang et al., 2010 Wang et al., 2003). moreover in that location are no reports of physcion (3), emodin (4), umbelliferone (5), scoparone (6), aesculetin (7) in the family Polypodiaceae. In addition, coumarins is a uncommon constituent in ferns though antecedently obtained from genus Polypodium hastatum Thunb., a fern of the alike family Polypodiaceae (Yao et al., 2012). credit of these class of anthraquinones (3, 4) and coumarins (5-7) indicates that they would be utilise as chemotaxonomic markers for the species L. drymoglossoides inwardly the family. And this investigating may tag on feature of speech constituents in this genus. notwithstanding more phytochemistry studies on it are needed.AcknowledgementsThis chuck was financially back up by a hold from Zhongshan Science and applied science planning parturiency of Guangdong province (No. 20113A082).ReferencesHe S.Z., Xu W.F., 2007. traditional Chinese practice of medicine resources in Guizhou, Guizhou, 192.The pillar commission of Chinese Materia Medica, 1999. 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