白薇生物碱类成分抑制柑橘采后青霉病菌活性
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摘要
【目的】探究白薇抑制柑橘采后青霉病菌——意大利青霉活性部位的化学成分。【方法】采用抑菌活性靶向分离、溶剂萃取、各种柱层析及制备液相色谱分离单体化合物,核磁共振(NMR)和高分辨离子肼质谱(HR-IT-TOF-MS)鉴定分离的化合物。【结果】白薇乙酸乙酯(CAE)和正丁醇(CAB)萃取物有抑菌活性,正丁醇萃取物抑菌活性最强,大孔树脂进一步分离富集抑菌活性,CAB-C2为白薇抑菌活性部位,质量浓度为0.625 mg·mL-1时其抑菌圈直径达到16.25 mm。采用各种柱层析及制备液相色谱技术从活性部位中分离出5个单体化合物,经NMR和MS鉴定为10β-N-氧化-7-脱甲氧基娃儿滕碱(1)、9-脱氢安托芬(2)、9,14-脱氢安托芬(3)、14羟基-N-氧化-7-脱甲氧基娃儿滕碱(4)、10α-N-氧化-7-脱甲氧基娃儿滕碱(5)。【结论】5种生物碱类活性成分均为首次从白薇中分离鉴定,生物碱类成分为白薇抑制柑橘采后青霉病菌的主要活性成分。
【Objective】Citrus fruits are often subjected to many postharvest diseases caused by various pathogens during picking,storage and transportation.Green and blue molds,caused by Penicillium digitatum and P.italicum,respectively,are two major postharvest citrus diseases and cause significant economic losses in the commercialization phase.Currently,control of postharvest citrus diseases relies mainly on the use of synthetic fungicides,which usually result in fungicide-resistance of the fungi,environment pollution and food safety problem.In recent years,much attention has been given to preventing citrus from the diseases by natural edible plant extracts.Scientists worldwide devote their time and energy to discover the high effect,low toxicity,safe and inexpensive plant-derived fungicides.Our researches also focus on plant-derived fungicides and chemical constituents target to inhibit P.digitatum and P.italicum in vitro and in vivo.Previously we showed the antifungal activities of Cynanchum atratum(CA) against 15 phytopathogenic fungi causing the postharvest diseases in fruits and vegetables.However,antifungal compoments were not clear.The extracts of n-butanol showed the best antifungal activity against P.italicum.In order to illuminate the antifungal constituents of the active fraction from C.atratum(CA) against phytopathogenic fungi P.italicum that cause citrus postharvest blue mould.【Methods】Antifungal bioassay-guided isolation and identification of constituents in the active fractionfollowed by liquid-liquid extraction and various column chromatographies.The preparative HPLC was used finally to get the pure compounds.The isolated compounds were identified by NMR and HR-ITTOF-MS.【Results】Ethyl acetate(CAE) and n-butanol(CAB) liquid-liquid extracts at the concentration of 25 mg· mL-1 showed antifungal activity with the inhibition zone of 14.3 and 20.5 mm,respectively.Moreover,CAB showed a higher antifungal activity than CAE and CA at the same concentrations.The water extracts showed no antifungal activity.CAB was further isolated to get the antifungal components.D101 macroporous resin column was firstly used to further enrich the antifungal constituents,which yielded four fractions(CAB-A to CAB-D),and only CAB-C fraction(the third fraction) showed antifungal activity at the concentration of 1.25 mg· mL-1.CAB-B(the second fraction) and CAB-C fractions showed antifungal activity at the concentration of 2.5 mg· mL-1.CAB-B,CAB-C and CAB-D(the fourth fraction) fractions showed antifungal activity at the concentration of 5.0 mg· mL-1.So the CAB-C fraction was further isolated by silica gel chromatography and yielded four fractions(CAB-C1 to CABC4).Only CAB-C2 fraction(the second fraction) showed antifungal activity at the concentration of 0.625 mg· mL-1,while CAB-C3 fraction showed antifungal activity at the concentration of 1.25 mg· mL-1.However,CAB-C1 and CAB-C4 fractions showed no antifungal activity even at 10 mg · mL-1.The CABC2 was the active fraction with the antifungal inhibition zone 16.25 mm at the concentration of 0.625 mg · mL-1.CAB-C2 fraction was further isolated by ODS and Sephadex LH-20 column chromatographies.Finally,five pure compounds were isolated using various column chromatographies and preparative HPLC.Their structures were elucidated by NMR and MS and identified as 10β-(-)-antofine N-oxide,9-dehydroantofine,9,14-dehydroantofine,14-hydroxyantofine N-oxide,and 10α-(-)-antofine N-oxide.【Conclusion】The five alkaloids were isolated for the first time from C.atratum.Alkaloids were the major antifungal constituents in C.atratum against P.italicum.
【Objective】Citrus fruits are often subjected to many postharvest diseases caused by various pathogens during picking,storage and transportation.Green and blue molds,caused by Penicillium digitatum and P.italicum,respectively,are two major postharvest citrus diseases and cause significant economic losses in the commercialization phase.Currently,control of postharvest citrus diseases relies mainly on the use of synthetic fungicides,which usually result in fungicide-resistance of the fungi,environment pollution and food safety problem.In recent years,much attention has been given to preventing citrus from the diseases by natural edible plant extracts.Scientists worldwide devote their time and energy to discover the high effect,low toxicity,safe and inexpensive plant-derived fungicides.Our researches also focus on plant-derived fungicides and chemical constituents target to inhibit P.digitatum and P.italicum in vitro and in vivo.Previously we showed the antifungal activities of Cynanchum atratum(CA) against 15 phytopathogenic fungi causing the postharvest diseases in fruits and vegetables.However,antifungal compoments were not clear.The extracts of n-butanol showed the best antifungal activity against P.italicum.In order to illuminate the antifungal constituents of the active fraction from C.atratum(CA) against phytopathogenic fungi P.italicum that cause citrus postharvest blue mould.【Methods】Antifungal bioassay-guided isolation and identification of constituents in the active fractionfollowed by liquid-liquid extraction and various column chromatographies.The preparative HPLC was used finally to get the pure compounds.The isolated compounds were identified by NMR and HR-ITTOF-MS.【Results】Ethyl acetate(CAE) and n-butanol(CAB) liquid-liquid extracts at the concentration of 25 mg· mL-1 showed antifungal activity with the inhibition zone of 14.3 and 20.5 mm,respectively.Moreover,CAB showed a higher antifungal activity than CAE and CA at the same concentrations.The water extracts showed no antifungal activity.CAB was further isolated to get the antifungal components.D101 macroporous resin column was firstly used to further enrich the antifungal constituents,which yielded four fractions(CAB-A to CAB-D),and only CAB-C fraction(the third fraction) showed antifungal activity at the concentration of 1.25 mg· mL-1.CAB-B(the second fraction) and CAB-C fractions showed antifungal activity at the concentration of 2.5 mg· mL-1.CAB-B,CAB-C and CAB-D(the fourth fraction) fractions showed antifungal activity at the concentration of 5.0 mg· mL-1.So the CAB-C fraction was further isolated by silica gel chromatography and yielded four fractions(CAB-C1 to CABC4).Only CAB-C2 fraction(the second fraction) showed antifungal activity at the concentration of 0.625 mg· mL-1,while CAB-C3 fraction showed antifungal activity at the concentration of 1.25 mg· mL-1.However,CAB-C1 and CAB-C4 fractions showed no antifungal activity even at 10 mg · mL-1.The CABC2 was the active fraction with the antifungal inhibition zone 16.25 mm at the concentration of 0.625 mg · mL-1.CAB-C2 fraction was further isolated by ODS and Sephadex LH-20 column chromatographies.Finally,five pure compounds were isolated using various column chromatographies and preparative HPLC.Their structures were elucidated by NMR and MS and identified as 10β-(-)-antofine N-oxide,9-dehydroantofine,9,14-dehydroantofine,14-hydroxyantofine N-oxide,and 10α-(-)-antofine N-oxide.【Conclusion】The five alkaloids were isolated for the first time from C.atratum.Alkaloids were the major antifungal constituents in C.atratum against P.italicum.
引文
[1]ZAFAR I,ZORA S,RAVJIT K,SAEED A.Management of citrus blue and green moulds through application of organic elicitors[J].Australasian Plant Pathology,2012,41(1):69-77.
[2]KANETIS L,FORETER H,ADASKAVEG J E.Comparative efficacy of the new postharvest fungicides azoxystrobin,fludioxonil,and pyrimethanil for managing citrus green mold[J].Plant Disease,2007,91(11):1502-1511.
[3]HAO W N,ZHONG G H,HU M Y,LUO J J,WENG Q F,RIZ-WAN-UL-HAQ M.Control of citrus postharvest green and blue mold and sour rot by tea saponin combined with imazalil and prochloraz[J].Postharvest Biology and Technology,2010,56(1):39-43.
[4]HUANG Y,WILD B L,MORRIS S C.Postharvest biological control of Penicillium digitatum decay on citrus fruit by Bacillus pumilus[J].Annals of Applied Biology,1992,120(2):367-372.
[5]DROBY S,COHEN L,DAUS A,WEISS B,HOREV B,CH-ALUTZ E,KATZ H,KEREN-TZUR M,SHACHNAI A.Commercial testing of Aspire:a yeast preparation for the biological control of postharvest decay of citrus[J].Biological Control,1998,12(2):97-101.
[6]PORAT R,DAUS A,WEISS B,COHEN L,FALLIK E,DRO-BY S.Reduction of postharvest decay in organic citrus fruit by a short hot water brushing treatment[J].Postharvest Biology and Technology,2000,18(2):151-157.
[7]HONG S I,LEE H H,KIM D.Effects of hot water treatment on the storage stability of Satsuma mandarin as a postharvest decay control[J].Postharvest Biology and Technology,2007,43(2):271-279.
[8]MONTESINOS-HERRERO C,PALOU L.Combination of physical and low-toxicity chemical postharvest treatments for integrated disease management of citrus fruit:a review[J].Stewart Postharvest Review,2010,6(1):1-11.
[9]SMILANICK J L,MANSOUR M F,GABLER F M,SOREN-SON D.Control of citrus postharvest green mold and sour rot by potassium sorbate combined with heat and fungicides[J].Postharvest Biology and Technology,2008,47(2):226-238.
[10]SINGH H,AL-SAMARAI G,SYARHABIL M.Exploitation of natural products as an alternative strategy to control postharvest fungal rotting of citrus[J].International Journal of Scientific and Research Publications,2012,2(3):1-4.
[11]SANCHEZ-GONZALEZ L,HAFER M C,CHIRALT A,GON-ZALEZ-MARTINEZ C.Physical properties of edible chitosan films containing bergamot essential oil and their inhibitory action on Penicillium italicum[J].Carbohydrate Polymers,2010,82(2):277-283.
[12]DU P W,REGNIEREGNIER T,COMBRINCK S.Essential oil amended coatings as alternatives to synthetic fungicides in citrus postharvest management[J].Postharvest Biology and Technology,2009,53(3):117-122.
[13]TYAGI A K,MALIK A.Antimicrobial potential and chemical composition of Mentha piperita oil in liquid and vapour phase against food spoiling microorganisms[J].Food Control,2011,22(11):1707-1714.
[14]YAHYAZADEH M R,OMIDBAIGI R Z,TAHERI H.Effect of some essential oils on mycelial growth of Penicillium digitatum Sacc.[J].World Journal of Microbiology and Biotechnology,2008,24(8):1445-1450.
[15]WAN C P,HAN J X,CHEN C Y,YAO L L,CHEN J Y,YUANT.Monosubstituted benzene derivatives from fruits of Ficus hirta and their antifungal activity against phytopathogen Penicillium italicum[J].Journal of Agricultural and Food Chemistry,2016,64(28):5621-5624.
[16]CHEN C Y,ZHENG J P,WAN C P,CHEN M,CHEN J Y.Effect of carboxymethyl cellulose coating enriched with clove oil on postharvest quality of‘Xinyu’mandarin oranges[J].Fruits,2016,71(5):319-327.
[17]CHEN C Y,PENG X,ZENG R,CHEN M,WAN C P,CHEN JY.Ficus hirta fruits extract incorporated into an alginate-based edible coating for Nanfeng mandarin preservation[J].Scientia Horticulturae,2016,202:41-48.
[18]CHEN C Y,WAN C P,PENG X,CHEN Y H,CHEN M,CHENJ Y.Optimization of antifungal extracts from Ficus hirta fruits using response surface methodology and antifungal activity tests[J].Molecules,2015,20(11):19647-19659.
[19]CHEN C Y,PENG X,ZENG R,WAN C P,CHEN M,CHEN JY.Physiological and biochemical responses in cold-stored citrus fruits to carboxymethyl cellulose coating containing ethanol extract of Impatiens balsamina L.stems[J].Journal of Food Processing and Preservation,2017,41(4):e12999.
[20]袁鹰,张卫东,柳润辉,扈晓佳,苏娟,郑兆广,张薇.白薇的化学成分和药理研究进展[J].药学实践杂志,2007,25(1):6-9.YUAN Ying,ZHANG Weidong,LIU Runhui,HU Xiaojia,SUJuan,ZHENG Zhaoguang,ZHANG Wei.Advances in studies on chemical constituents and pharmacology of Cynanchum atratum[J].Journal of Pharmaceutical Practice,2007,25(1):6-9.
[21]彭旋,陈楚英,陈金印,万春鹏.白薇提取物的抗氧化和抑菌活性[J].江苏农业科学,2017,45(4):140-144.PENG Xuan,CHEN Chuying,CHEN Jinyin,WAN Chunpeng.Antioxidant and antifungi activities of Cynanchum atratum[J].Jiangsu Agricultural Sciences,2017,45(4):140-144.
[22]郑嘉鹏,甘武,陈玉环,陈楚英,陈金印.白薇提取液对新余蜜橘采后青霉病的防治效果研究[J].江西农业大学学报,2017,39(6):1119-1125.ZHENG Jiapeng,GAN Wu,CHEN Yuhuan,CHEN Chuying,CHEN Jinyin.Control effects of Cynanchum Atratum extracts on postharvest blue mold in Xinyu tangerine[J].Acta Agriculturae Universitatis Jiangxiensis,2017,39(6):1119-1125.
[23]彭旋,陈玉环,陈金印.白薇提取液对意大利青霉抑菌机制及脐橙青霉病防治效果的研究[J].植物病理学报,2017,47(3):398-405.PENG Xuan,CHEN Chuying,CHEN Jinyin.Antifungal mechanism of Cynanchum atratum Bunge extracts on Penicillium italicum and control effect on blue mold of navel orange[J].Acta Phytopathologica Sinica,2017,47(3):398-405.
[24]彭旋,万春鹏,陈玉环,陈楚英,陈金印.响应面法优化白薇抑菌物质超声提取工艺[J].食品工业科技,2017,38(7):176-182.PENG Xuan,WAN Chunpeng,CHEN Yuhuan,CHEN Chuying,CHEN Jinyin.Optimization of ultrasound extraction of antibacterial material from Cynanchum atratum Bunge with response surface methodology[J].Science and Technology of Food Industry,2017,38(7):176-182.
[25]LAVAULY M,RICHOMME P,BRUNETON J.New phenatroindolizidine N-oxides alkaloids isolated from Vincetoxicum hirudinaria Medic[J].Pharmaceutica Acta Helvetiae,1994,68(4):225-227.
[26]FABER L,WIEGREBE W.Stereospecific synthesis of a 9,11,12,13,13a,14-hexahydro-dibenzo(f,h)pyrrolo(1,2-b)isoquinolinealkaloid[J].Helvetica Chimica Acta,1973,56(8):2882-2884.
[27]WU T S,SU C R,LEE K H.Cytotoxic and anti-HIV phenanthroindolizidine alkaloids from Cryptocarya chinensis[J].Natural Product Communications,2012,7(6):725-727.
[28]STAERK D,CHRISTENSEN J,LEMMICH E,DUUS J O,OL-SEN C E,JAROSZEWSKI J W.Cytotoxic activity of some phenanthroindolizidine N-oxide alkaloids from Cynanchum vincetoxicum[J].Journal of Natural Products,2000,63(11):1584-1586.
[29]刘迪,吴卫,李冠.白喉乌头总生物碱抑菌杀虫活性的初步研究[J].新疆农业科学,2009,46(3):620-624.LIU Di,WU Wei,LI Guan.Primary studies on the fungicidal and insecticidal activities of total alkaloids from Aconitum leucostomum Worosch[J].Xinjiang Agricultural Sciences,2009,46(3):620-624.
[30]BAUMGARTNER B,ERDELMEIER C A J,WRIGHT A D,RALI T,STICHER O.Antofine,a strong antifungal alkaloid from Ficus septica leaves[J].Planta Medica,1989,55(7):652-653.
[31]BAUMGARTNER B,ERDELMEIER C A J,WRIGHT A D,RALI T,STICHER O.An antimicrobial alkaloid from Ficus septica[J].Phytochemistry,1990,29(10):3327-3330.
[32]RAO K N,VENKATACHALAM S R.Inhibition of dihydrofolate reductase and cell growth activity by the phenanthroindolizidine alkaloids pergularinine and tylophorinidine:the in vitro cytotoxicity of these plant alkaloids and their potential as antimicrobial and anticancer agents[J].Toxicology in Vitro,2000,14(1):53-59.
[2]KANETIS L,FORETER H,ADASKAVEG J E.Comparative efficacy of the new postharvest fungicides azoxystrobin,fludioxonil,and pyrimethanil for managing citrus green mold[J].Plant Disease,2007,91(11):1502-1511.
[3]HAO W N,ZHONG G H,HU M Y,LUO J J,WENG Q F,RIZ-WAN-UL-HAQ M.Control of citrus postharvest green and blue mold and sour rot by tea saponin combined with imazalil and prochloraz[J].Postharvest Biology and Technology,2010,56(1):39-43.
[4]HUANG Y,WILD B L,MORRIS S C.Postharvest biological control of Penicillium digitatum decay on citrus fruit by Bacillus pumilus[J].Annals of Applied Biology,1992,120(2):367-372.
[5]DROBY S,COHEN L,DAUS A,WEISS B,HOREV B,CH-ALUTZ E,KATZ H,KEREN-TZUR M,SHACHNAI A.Commercial testing of Aspire:a yeast preparation for the biological control of postharvest decay of citrus[J].Biological Control,1998,12(2):97-101.
[6]PORAT R,DAUS A,WEISS B,COHEN L,FALLIK E,DRO-BY S.Reduction of postharvest decay in organic citrus fruit by a short hot water brushing treatment[J].Postharvest Biology and Technology,2000,18(2):151-157.
[7]HONG S I,LEE H H,KIM D.Effects of hot water treatment on the storage stability of Satsuma mandarin as a postharvest decay control[J].Postharvest Biology and Technology,2007,43(2):271-279.
[8]MONTESINOS-HERRERO C,PALOU L.Combination of physical and low-toxicity chemical postharvest treatments for integrated disease management of citrus fruit:a review[J].Stewart Postharvest Review,2010,6(1):1-11.
[9]SMILANICK J L,MANSOUR M F,GABLER F M,SOREN-SON D.Control of citrus postharvest green mold and sour rot by potassium sorbate combined with heat and fungicides[J].Postharvest Biology and Technology,2008,47(2):226-238.
[10]SINGH H,AL-SAMARAI G,SYARHABIL M.Exploitation of natural products as an alternative strategy to control postharvest fungal rotting of citrus[J].International Journal of Scientific and Research Publications,2012,2(3):1-4.
[11]SANCHEZ-GONZALEZ L,HAFER M C,CHIRALT A,GON-ZALEZ-MARTINEZ C.Physical properties of edible chitosan films containing bergamot essential oil and their inhibitory action on Penicillium italicum[J].Carbohydrate Polymers,2010,82(2):277-283.
[12]DU P W,REGNIEREGNIER T,COMBRINCK S.Essential oil amended coatings as alternatives to synthetic fungicides in citrus postharvest management[J].Postharvest Biology and Technology,2009,53(3):117-122.
[13]TYAGI A K,MALIK A.Antimicrobial potential and chemical composition of Mentha piperita oil in liquid and vapour phase against food spoiling microorganisms[J].Food Control,2011,22(11):1707-1714.
[14]YAHYAZADEH M R,OMIDBAIGI R Z,TAHERI H.Effect of some essential oils on mycelial growth of Penicillium digitatum Sacc.[J].World Journal of Microbiology and Biotechnology,2008,24(8):1445-1450.
[15]WAN C P,HAN J X,CHEN C Y,YAO L L,CHEN J Y,YUANT.Monosubstituted benzene derivatives from fruits of Ficus hirta and their antifungal activity against phytopathogen Penicillium italicum[J].Journal of Agricultural and Food Chemistry,2016,64(28):5621-5624.
[16]CHEN C Y,ZHENG J P,WAN C P,CHEN M,CHEN J Y.Effect of carboxymethyl cellulose coating enriched with clove oil on postharvest quality of‘Xinyu’mandarin oranges[J].Fruits,2016,71(5):319-327.
[17]CHEN C Y,PENG X,ZENG R,CHEN M,WAN C P,CHEN JY.Ficus hirta fruits extract incorporated into an alginate-based edible coating for Nanfeng mandarin preservation[J].Scientia Horticulturae,2016,202:41-48.
[18]CHEN C Y,WAN C P,PENG X,CHEN Y H,CHEN M,CHENJ Y.Optimization of antifungal extracts from Ficus hirta fruits using response surface methodology and antifungal activity tests[J].Molecules,2015,20(11):19647-19659.
[19]CHEN C Y,PENG X,ZENG R,WAN C P,CHEN M,CHEN JY.Physiological and biochemical responses in cold-stored citrus fruits to carboxymethyl cellulose coating containing ethanol extract of Impatiens balsamina L.stems[J].Journal of Food Processing and Preservation,2017,41(4):e12999.
[20]袁鹰,张卫东,柳润辉,扈晓佳,苏娟,郑兆广,张薇.白薇的化学成分和药理研究进展[J].药学实践杂志,2007,25(1):6-9.YUAN Ying,ZHANG Weidong,LIU Runhui,HU Xiaojia,SUJuan,ZHENG Zhaoguang,ZHANG Wei.Advances in studies on chemical constituents and pharmacology of Cynanchum atratum[J].Journal of Pharmaceutical Practice,2007,25(1):6-9.
[21]彭旋,陈楚英,陈金印,万春鹏.白薇提取物的抗氧化和抑菌活性[J].江苏农业科学,2017,45(4):140-144.PENG Xuan,CHEN Chuying,CHEN Jinyin,WAN Chunpeng.Antioxidant and antifungi activities of Cynanchum atratum[J].Jiangsu Agricultural Sciences,2017,45(4):140-144.
[22]郑嘉鹏,甘武,陈玉环,陈楚英,陈金印.白薇提取液对新余蜜橘采后青霉病的防治效果研究[J].江西农业大学学报,2017,39(6):1119-1125.ZHENG Jiapeng,GAN Wu,CHEN Yuhuan,CHEN Chuying,CHEN Jinyin.Control effects of Cynanchum Atratum extracts on postharvest blue mold in Xinyu tangerine[J].Acta Agriculturae Universitatis Jiangxiensis,2017,39(6):1119-1125.
[23]彭旋,陈玉环,陈金印.白薇提取液对意大利青霉抑菌机制及脐橙青霉病防治效果的研究[J].植物病理学报,2017,47(3):398-405.PENG Xuan,CHEN Chuying,CHEN Jinyin.Antifungal mechanism of Cynanchum atratum Bunge extracts on Penicillium italicum and control effect on blue mold of navel orange[J].Acta Phytopathologica Sinica,2017,47(3):398-405.
[24]彭旋,万春鹏,陈玉环,陈楚英,陈金印.响应面法优化白薇抑菌物质超声提取工艺[J].食品工业科技,2017,38(7):176-182.PENG Xuan,WAN Chunpeng,CHEN Yuhuan,CHEN Chuying,CHEN Jinyin.Optimization of ultrasound extraction of antibacterial material from Cynanchum atratum Bunge with response surface methodology[J].Science and Technology of Food Industry,2017,38(7):176-182.
[25]LAVAULY M,RICHOMME P,BRUNETON J.New phenatroindolizidine N-oxides alkaloids isolated from Vincetoxicum hirudinaria Medic[J].Pharmaceutica Acta Helvetiae,1994,68(4):225-227.
[26]FABER L,WIEGREBE W.Stereospecific synthesis of a 9,11,12,13,13a,14-hexahydro-dibenzo(f,h)pyrrolo(1,2-b)isoquinolinealkaloid[J].Helvetica Chimica Acta,1973,56(8):2882-2884.
[27]WU T S,SU C R,LEE K H.Cytotoxic and anti-HIV phenanthroindolizidine alkaloids from Cryptocarya chinensis[J].Natural Product Communications,2012,7(6):725-727.
[28]STAERK D,CHRISTENSEN J,LEMMICH E,DUUS J O,OL-SEN C E,JAROSZEWSKI J W.Cytotoxic activity of some phenanthroindolizidine N-oxide alkaloids from Cynanchum vincetoxicum[J].Journal of Natural Products,2000,63(11):1584-1586.
[29]刘迪,吴卫,李冠.白喉乌头总生物碱抑菌杀虫活性的初步研究[J].新疆农业科学,2009,46(3):620-624.LIU Di,WU Wei,LI Guan.Primary studies on the fungicidal and insecticidal activities of total alkaloids from Aconitum leucostomum Worosch[J].Xinjiang Agricultural Sciences,2009,46(3):620-624.
[30]BAUMGARTNER B,ERDELMEIER C A J,WRIGHT A D,RALI T,STICHER O.Antofine,a strong antifungal alkaloid from Ficus septica leaves[J].Planta Medica,1989,55(7):652-653.
[31]BAUMGARTNER B,ERDELMEIER C A J,WRIGHT A D,RALI T,STICHER O.An antimicrobial alkaloid from Ficus septica[J].Phytochemistry,1990,29(10):3327-3330.
[32]RAO K N,VENKATACHALAM S R.Inhibition of dihydrofolate reductase and cell growth activity by the phenanthroindolizidine alkaloids pergularinine and tylophorinidine:the in vitro cytotoxicity of these plant alkaloids and their potential as antimicrobial and anticancer agents[J].Toxicology in Vitro,2000,14(1):53-59.