野艾蒿中双四氢呋喃类木脂素的提取分离及其抑菌活性
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摘要
为筛选新型植物源杀菌剂,对野艾蒿Artemisia lavandulaefolia DC.地上组织中的化学成分进行了研究。采用甲醇提取、液-液萃取、柱层析及半制备高效液相色谱等技术从乙酸乙酯浸膏中分离得到6个化合物;利用质谱及核磁共振等波谱技术确定这6个化合物分别是epiashchantin (1)、ashantin (2)、sesartemin (3)、epimagnolin A (4)、epiyangambin (5)和diayangambin (6),均属于双四氢呋喃类木脂素。采用菌丝生长速率法测定了其抑菌活性,结果表明:化合物1和3对番茄早疫病菌Alternaria solani的菌丝生长表现出明显抑制作用,EC_(50)值分别为14.3和11.0μg/mL;化合物3、5和6对玉米纹枯病菌Rhizoctonia solani的菌丝生长也表现出抑制作用,EC_(50)值分别为17.4、42.6和54.3μg/mL。
In order to discover novel botanical fungicides, the chemical constituents of the aerial parts of Artemisia lavandulaefolia DC. were investigated. The aerial parts were extracted with methanol. By using liquid-liquid extraction, column chromatography, high performance preparative liquid chromatography and other techniques, 6 pure compounds were finally isolated from the ethyl acetate phase. The compounds were identified as bistetrahydrofuran lignans, including epiashchantin(1),ashantin(2), sesartemin(3), epimagnolin A(4), epiyangambin(5) and diayangambin(6), according to NMR and MS data. The mycelium growth rate method was used to determine the antifungal activities.The results showed that compound 1 and 3 significantly inhibited the growth of Alternaria solani with the EC_(50) value of 14.3 μg/mL and 11.0 μg/mL, respectively. Compound 3, 5 and 6 also showed inhibitory effect against the mycelia growth of Rhizoctonia solani with the EC_(50) value of 17.4, 42.6 and54.3 μg/mL, respectively.
In order to discover novel botanical fungicides, the chemical constituents of the aerial parts of Artemisia lavandulaefolia DC. were investigated. The aerial parts were extracted with methanol. By using liquid-liquid extraction, column chromatography, high performance preparative liquid chromatography and other techniques, 6 pure compounds were finally isolated from the ethyl acetate phase. The compounds were identified as bistetrahydrofuran lignans, including epiashchantin(1),ashantin(2), sesartemin(3), epimagnolin A(4), epiyangambin(5) and diayangambin(6), according to NMR and MS data. The mycelium growth rate method was used to determine the antifungal activities.The results showed that compound 1 and 3 significantly inhibited the growth of Alternaria solani with the EC_(50) value of 14.3 μg/mL and 11.0 μg/mL, respectively. Compound 3, 5 and 6 also showed inhibitory effect against the mycelia growth of Rhizoctonia solani with the EC_(50) value of 17.4, 42.6 and54.3 μg/mL, respectively.
引文
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[14]AHMED A A, MAHMOUD A A, ALI E T, et al. Two highly oxygenated eudesmanes and 10 lignans from Achillea holosericea[J].Phytochemistry, 2002, 59(8):851-856.
[15]GREGER H, HOFER O. New unsymmetrically substituted tetrahydrofurofuran lignans from Artemisia absinthium[J].Tetrahedron, 1980, 36(24):3551-3558.
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[17]CASTRO-FARIA-NETO H C, MARTINS M A, SILVA P M, et al.Pharmacological profile of epiyangambin:a furofuran lignan with PAF antagonist activity[J]. J Lipid Mediat, 1993, 7(1):1-9.
[18]SOLíS P N, OLMEDO D, NAKAMURA N, et al. A new larvicidal lignan from Piper fimbriulatum[J]. Pharm Biol, 2005, 43(4):378-381.
[19]AKIYAMA K, YAMAUCHI S, NAKATO T, et al. Antifungal activity of tetra-substituted tetrahydrofuran lignan,(-)-virgatusin, and its structure-activity relationship[J]. Biosci Biotechnol Biochem,2007, 71(4):1028-1035.
[20]郭宗儒.天然产物的结构改造[J].药学学报, 2012, 47(2):144-157.GUO Z R. Modification of natural products for drug discovery[J].Acta Pharmaceutica Sinica, 2012, 47(2):144-157.
[21]郭琪,冯俊涛,方香玲,等.双四氢呋喃木脂素Prinsepiol酰化衍生物的合成及其抑菌活性研究[J].西北农林科技大学学报(自然科学版), 2008, 36(12):223-228.GUO Q, FENG J T, FANG X L, et al. Synthesis and antifungal activity of acyl derivatives of Prinsepiol[J]. J Northwest A&F Univ(Nat Sci Ed), 2008, 36(12):223-228.
[2]胡林峰,崔乘幸,吴玉博,等.艾蒿化学成分及其生物活性研究进展[J].河南科技学院学报(自然科学版), 2010, 38(4):75-78.HU L F, CUI C X, WU Y B, et al. Research advances on chemical constituents and bioactivities of Artemisia argyi[J]. J Henan Inst Sci Technol(Nat Sci Ed), 2010, 38(4):75-78.
[3]马麟,周海玲,龚又明,等.野艾蒿中黄酮类成分的研究[J].中药新药与临床药理, 2012, 23(5):555-557.MA L, ZHOU H L, GONG Y M, et al. Analysis of flavonoids from aerial parts of Artemisia lavandulaefolia[J]. Tradit Chin Drug Res Clin Pharmacol, 2012, 23(5):555-557.
[4]HUANG X, GE S Y, LIU J H, et al. Chemical composition and bioactivity of the essential oil from Artemisia lavandulaefolia(Asteraceae)on Plutella xylostella(Lepidoptera:Plutellidae)[J]. Flo Entomol, 2018, 101(1):44-48.
[5]ZHOU J, ZOU K X, ZHANG W J, et al. Efficacy of compounds isolated from the essential oil of Artemisia lavandulaefolia in control of the cigarette beetle, Lasioderma serricorne[J]. Molecules, 2018,23(2):343.
[6]江贵波,曾任森,陈少雄,等.中药野艾挥发性物质的抗菌活性与成分鉴定[J].沈阳农业大学学报, 2008, 39(4):495-498.JIANG G B, ZENG R S, CHEN S X, et al. Identification and antimicrobial effects of volatiles in traditional Chinese medicine herb Artemisia lavandulaefolia DC.Prodr[J]. J Shenyang Agric Univ, 2008,39(4):495-498.
[7]莫茂军,吴洪基,韩诗畴,等. 16种植物乙醇提取物对桔全爪螨的生物活性测定[J].环境昆虫学报, 2008, 30(1):44-49.MO M J, WU H J, HAN S C, et al. Bio-activity of the alcohol extracts from 16 plant species against citrus red mite Panonychus citri McGregor[J]. J Environ Entomol, 2008, 30(1):44-49.
[8]袁海滨,刘莹,丁玉骁,等.野艾蒿精油对双斑萤叶甲成虫的熏蒸活性及体内酶活力的影响[J].吉林农业大学学报, 2014, 36(1):30-35.YUAN H B, LIU Y, DING Y X, et al. Effects of essential oil from Artemisia lavandulaefolia DC.on fumigation activity and several enzymes activities of Monolepta hieroglyphica(Motschulsky)Adults[J]. J Jilin Agric Univ, 2014, 36(1):30-35.
[9]王丹,尉捷,许欣然,等.天然双四氢呋喃类木脂素化合物的化学研究进展[J].中国实验方剂学杂志, 2017, 23(8):226-234.WANG D, YU J, XU X R, et al. Research progress of chemical compounds in tetrahydrofuran lignans[J]. Chin J Exp Tradit Med Formulae, 2017, 23(8):226-234.
[10]KAMAL-ELDIN A, YOUSIF G. A furofuran lignan from Sesamum alatum[J]. Phytochemistry, 1992, 31(8):2911-2912.
[11]CRAWFORD J M, PORTMANN C, ZHANG X, et al. Small molecule perimeter defense in entomopathogenic bacteria[J]. Proc Natl Acad Sci USA, 2012, 109(27):10821-10826.
[12]冯志东.植物病理与研究方法[M].北京:中国农业出版社, 1998.FANG Z D. Method of plant pathology research[M]. Beijing:China Agriculture Press, 1998.
[13]TULAKEA, TU P F. Nine lignans from Artemisia absinthium L.[J]. J Chin Pharm Sci, 2012, 21(4):360-364.
[14]AHMED A A, MAHMOUD A A, ALI E T, et al. Two highly oxygenated eudesmanes and 10 lignans from Achillea holosericea[J].Phytochemistry, 2002, 59(8):851-856.
[15]GREGER H, HOFER O. New unsymmetrically substituted tetrahydrofurofuran lignans from Artemisia absinthium[J].Tetrahedron, 1980, 36(24):3551-3558.
[16]BROWN R C D, BATAILLE C J R, BRUTON G, et al. C-H insertion approach to the synthesis of endo, exo-furofuranones:synthesis of(±)-asarinin,(±)-epimagnolin a, and(±)-fargesin[J]. J Org Chem,2001, 66(20):6719-6728.
[17]CASTRO-FARIA-NETO H C, MARTINS M A, SILVA P M, et al.Pharmacological profile of epiyangambin:a furofuran lignan with PAF antagonist activity[J]. J Lipid Mediat, 1993, 7(1):1-9.
[18]SOLíS P N, OLMEDO D, NAKAMURA N, et al. A new larvicidal lignan from Piper fimbriulatum[J]. Pharm Biol, 2005, 43(4):378-381.
[19]AKIYAMA K, YAMAUCHI S, NAKATO T, et al. Antifungal activity of tetra-substituted tetrahydrofuran lignan,(-)-virgatusin, and its structure-activity relationship[J]. Biosci Biotechnol Biochem,2007, 71(4):1028-1035.
[20]郭宗儒.天然产物的结构改造[J].药学学报, 2012, 47(2):144-157.GUO Z R. Modification of natural products for drug discovery[J].Acta Pharmaceutica Sinica, 2012, 47(2):144-157.
[21]郭琪,冯俊涛,方香玲,等.双四氢呋喃木脂素Prinsepiol酰化衍生物的合成及其抑菌活性研究[J].西北农林科技大学学报(自然科学版), 2008, 36(12):223-228.GUO Q, FENG J T, FANG X L, et al. Synthesis and antifungal activity of acyl derivatives of Prinsepiol[J]. J Northwest A&F Univ(Nat Sci Ed), 2008, 36(12):223-228.