苍耳子中萜类化学成分的研究
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摘要
目的研究苍耳子Xanthium strumarium L.的萜类成分。方法苍耳子70%乙醇提取物采用硅胶色谱柱、ODS反相柱色谱与半制备液相进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到13个化合物,分别鉴定为atractyligenin (1)、2-O-β-D-glucopyranosyl-atractyligenin (2)、junipeionoloside (3)、(1R,6R,9S)-6,9,11-trihydroxy-4,7-megastigmadien-3-one 11-O-β-D-glucopyranoside (4)、(1R,6R,9S)-6,9,11-trihydroxy-4,7-megastigmadien-3-one (5)、(1S,5R,6R,9R)-megastigman-3-on-5,12-epoxy-9-ol (6)、vervenone-10-O-β-Dapiofuranosyl-(1″-6')-β-D-glucopyranoside (7)、11β,13-dihydro-4H-xanthalongin 4-O-β-D-glucopyranoside (8)、11α,13-dihydro-4H-xanthalongin 4-O-β-D-glucopyranoside (9)、 anhydrodehydroivalbin (10)、 4-O-dihydroinusoniolide (11)、lasidiol p-methoxybenzoate (12)、sibiriolide C (13)。结论所有化合物均为首次从该植物中分离得到。
AIM To study the chemical constituents of terpenoids from Xanthium strumarium L..METHODS The 70% ethanol extract from X. strumarium was isolated and purified by silica,ODS and RPHPLC,then the structures of obtained compounds were identified by physicochemical properties and spectral data.RESULTS Thirteen compounds were isolated and identified as atractyligenin(1),2-O-β-D-glucopyranosyl-atractyligenin(2),junipeionoloside(3),(1 R,6 R,9 S)-6,9,11-trihydroxy-4,7-megastigmadien-3-one 11-O-β-D-glucopyranoside(4),(1 R,6 R,9 S)-6,9,11-trihydroxy-4,7-megastigmadien-3-one(5),(1 S,5 R,6 R, 9 R)-megastigman-3-on-5, 12-epoxy-9-ol(6), vervenone-10-O-β-D-apiofuranosyl-(1″-6')-β-Dglucopyranoside(7),11β,13-dihydro-4 H-xanthalongin 4-O-β-D-glucopyranoside(8),11α,13-dihydro-4 Hxanthalongin 4-O-β-D-glucopyranoside(9),anhydrodehydroivalbin(10),4-O-dihydroinusoniolide(11),lasidiol p-methoxybenzoate(12),sibiriolide C(13). CONCLUSION All compounds are isolated from thisplant for the first time.
AIM To study the chemical constituents of terpenoids from Xanthium strumarium L..METHODS The 70% ethanol extract from X. strumarium was isolated and purified by silica,ODS and RPHPLC,then the structures of obtained compounds were identified by physicochemical properties and spectral data.RESULTS Thirteen compounds were isolated and identified as atractyligenin(1),2-O-β-D-glucopyranosyl-atractyligenin(2),junipeionoloside(3),(1 R,6 R,9 S)-6,9,11-trihydroxy-4,7-megastigmadien-3-one 11-O-β-D-glucopyranoside(4),(1 R,6 R,9 S)-6,9,11-trihydroxy-4,7-megastigmadien-3-one(5),(1 S,5 R,6 R, 9 R)-megastigman-3-on-5, 12-epoxy-9-ol(6), vervenone-10-O-β-D-apiofuranosyl-(1″-6')-β-Dglucopyranoside(7),11β,13-dihydro-4 H-xanthalongin 4-O-β-D-glucopyranoside(8),11α,13-dihydro-4 Hxanthalongin 4-O-β-D-glucopyranoside(9),anhydrodehydroivalbin(10),4-O-dihydroinusoniolide(11),lasidiol p-methoxybenzoate(12),sibiriolide C(13). CONCLUSION All compounds are isolated from thisplant for the first time.
引文
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[21] Cumanda J,Marinoni G,De Bernardi M,et al. New sesquiterpenes from Xanthium catharticum[J]. J Nat Prod,1991,54(2):460-465.
[22] Bui V B,Liu S T,Zhu J J,et al. Sesquiterpene lactones from the aerial parts of Xanthium sibiricum and their cytotoxic effects on human cancer cell lines[J]. Phytochem Lett,2012,5(3):685-689.
[23] Sülsen V P,Lizarraga E,Mamadalieva N Z,et al. Potential of terpenoids and flavonoids from Asteraceae as anti-inflammatory,antitumor,and antiparasitic agents[J]. Evid-Based Compl Alt,2017,2017:6196198.
[24] Villarreal M L,Alvarez L,Alonso D,et al. Cytotoxic and antimicrobial screening of selected terpenoids from Asteraceae species[J]. J Ethnopharmacol,1994,42(1):25-29.
[25] Farzaei M H,Farzaei F,Abdollahi M,et al. A mechanistic review on medicinal plants used for rheumatoid arthritis in traditional persian medicine[J]. J Pharm Pharmacol,2016,68(10):1233-1248.
[26] Naqash S Y,Nazeer R A. Anticoagulant,antiherpetic and antibacterial activities of sulphated polysaccharide from Indian medicinal plant Tridax procumbens L.(Asteraceae)[J]. Appl Biochem Biotech,2011,165(3-4):902-912.
[2] Jiang H,Yang L,Ma G X,et al. New phenylpropanoid derivatives from the fruits of Xanthium sibiricum and their anti-inflammatory activity[J]. Fitoterapia,2017,117:11-15.
[3] Kumar V,Gundampati R K,Singh D K,et al. Photo-induced rapid biosynthesis of silver nanoparticle using aqueous extract of Xanthium strumarium and its antibacterial and antileishmanial activity[J]. J Ind Eng Chem,2016,37:224-236.
[4] Aranjani J M,Manuel A,Mallikarjuna Rao C,et al. Preliminary evaluation of in vitro cytotoxicity and in vivo antitumor activity of Xanthium strumarium in transplantable tumors in mice[J]. Am J Chinese Med,2013,41(1):145-162.
[5]张玉崑,吴寿金,张建国.苍耳草挥发油成分的研究[J].中草药,1995(1):48.
[6] Qin L,Han T,Li H,et al. A new thiazinedione from Xanthium strumarium[J]. Fitoterapia,2006,77(3):245-246.
[7] Jiang H,Ma G X,Yang L,et al. Rearranged ent-kauranoid glycosides from the fruits of Xanthium strumarium,and their antiproliferative activity[J]. Phytochem Lett, 2016, 18:192-196.
[8]姜海,杨柳,邢绪东,等.苍耳子的化学成分研究[J].中草药,2017,48(1):47-51.
[9] Piacente S,Pizza C,De Tommasi N,et al. Sesquiterpene and diterpene glycosides from Xanthium spinosum[J]. Phytochemistry,1996,41(5):1357-1360.
[10]姜海,张妍妍,张颖,等.苍耳子化学成分研究[J].中医药信息,2016,33(3):8-10.
[11] Jiang H,Yang L,Liu C,et al. Four new glycosides from the fruit of Xanthium sibiricum Patr[J]. Molecules,2013,18(10):12464-12473.
[12] Ma Y T,Huang M C,Hsu F L,et al. Thiazinedione from Xanthium strumarium[J]. Phytochemistry, 1998, 48(6):1083-1085.
[13] Lang R,Fromme T,Beusch A,et al. 2-O-β-D-Glucopyranosyl-carboxyatractyligenin from Coffea L. inhibits adenine nucleotide translocase in isolated mitochondria but is quantitatively degraded during coffee roasting[J]. Phytochemistry,2013,93:124-135.
[14] Champavier Y,Comte G,Vercauteren J,et al. Norterpenoid and sesquiterpenoid glucosides from Juniperus phynicea and Galega officinalis[J]. Phytochemistry, 1999, 50(7):1219-1223.
[15] Giang P M,Son P T,Matsunami K,et al. New megastigmane glucosides from Excoecaria cochinchinensis LOUR. var. cochinchinensis[J]. Chem Pharm Bull, 2005, 53(12):1600-1603.
[16] Nakanishi T,Iida N,Inatomi Y,et al. A monoterpene glucoside and three megastigmane glycosides from Juniperus communis var. depressa[J]. Chem Pharm Bull,2005,53(7):783-787.
[17] Matsunami K,Otsuka H,Kondo K,et al. Absolute configuration of(+)-pinoresinol 4-O-[6"-O-galloyl]-beta-D-glucopyranoside,macarangiosides E,and F isolated from the leaves of Macaranga tanarius[J]. Phytochemistry,2009,70(10):1277-1285.
[18] He W J,Fu Z H,Zeng G Z,et al. Terpene and lignan glycosides from the twigs and leaves of an endangered conifer,Cathaya argyrophylla[J]. Phytochemistry,2012,83:63-69.
[19] Passreiter C M,Merfort I,Bestendonk C,et al. 11α,13-and11β, 13-Dihydro-4H-xanthalongin 4-O-β-glucopyranosides:new sesquiterpene lactone glycosides from flowers of Arnica amplexicaulis and A. mollis[J]. Planta Med,1996,62(1):39-41.
[20] Marco J A,Sanz-Cervera J F,Corral J,et al. Xanthanolides from Xanthium:absolute configuration of xanthanol,isoxanthanol and their C-4 epimers[J]. Phytochemistry,1993,34(6):1569-1576.
[21] Cumanda J,Marinoni G,De Bernardi M,et al. New sesquiterpenes from Xanthium catharticum[J]. J Nat Prod,1991,54(2):460-465.
[22] Bui V B,Liu S T,Zhu J J,et al. Sesquiterpene lactones from the aerial parts of Xanthium sibiricum and their cytotoxic effects on human cancer cell lines[J]. Phytochem Lett,2012,5(3):685-689.
[23] Sülsen V P,Lizarraga E,Mamadalieva N Z,et al. Potential of terpenoids and flavonoids from Asteraceae as anti-inflammatory,antitumor,and antiparasitic agents[J]. Evid-Based Compl Alt,2017,2017:6196198.
[24] Villarreal M L,Alvarez L,Alonso D,et al. Cytotoxic and antimicrobial screening of selected terpenoids from Asteraceae species[J]. J Ethnopharmacol,1994,42(1):25-29.
[25] Farzaei M H,Farzaei F,Abdollahi M,et al. A mechanistic review on medicinal plants used for rheumatoid arthritis in traditional persian medicine[J]. J Pharm Pharmacol,2016,68(10):1233-1248.
[26] Naqash S Y,Nazeer R A. Anticoagulant,antiherpetic and antibacterial activities of sulphated polysaccharide from Indian medicinal plant Tridax procumbens L.(Asteraceae)[J]. Appl Biochem Biotech,2011,165(3-4):902-912.