白薇生物碱类成分抑制柑橘采后青霉病菌活性Antifungal activity of Cynanchum atratum alkaloids against citrus postharvest blue mould
陈楚英;彭旋;陈金印;万春鹏;
摘要(Abstract):
【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。
关键词(KeyWords): 柑橘;青霉病;意大利青霉;白薇;生物碱;活性成分
基金项目(Foundation): 国家自然科学基金(31760598)
作者(Author): 陈楚英;彭旋;陈金印;万春鹏;
Email:
DOI: 10.13925/j.cnki.gsxb.20180152
参考文献(References):
- [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.