CN108911969A - 用于防治柑橘溃疡病的化合物及其应用 - Google Patents

用于防治柑橘溃疡病的化合物及其应用 Download PDF

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CN108911969A
CN108911969A CN201810868704.9A CN201810868704A CN108911969A CN 108911969 A CN108911969 A CN 108911969A CN 201810868704 A CN201810868704 A CN 201810868704A CN 108911969 A CN108911969 A CN 108911969A
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bacterial canker
canker disease
citrus bacterial
preventing
dsf
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CN108911969B (zh
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刘晓玲
谭春斌
阳勇
杜洪飞
郭延垒
常长青
张炼辉
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South China Agricultural University
Chongqing Academy of Chinese Materia Medica
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South China Agricultural University
Chongqing Academy of Chinese Materia Medica
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

本发明提供了一系列用于防治柑橘溃疡病的化合物，其结构式为：其中，R1为H+或CH3 +中的一种，R1为H+或CH3 +中的一种本发明提供的化合物能够有效干扰或拮抗DSF群体效应，降低致病因子的表达，从而达到控制柑橘溃疡病的传播，治疗防治柑橘溃疡病。

Description

用于防治柑橘溃疡病的化合物及其应用
技术领域
本发明涉及一种化合物，更具的说涉及用于防治柑橘溃疡病的化合物及其应用。
背景技术
1991年唐纪良首次发现了DSF信号：野油菜黄单胞菌“8004”基因族与致病性密切相关， 任何一个基因突变都显著的影响胞外酶与多糖的产生。Barber等认为Xcc野生型菌体可能分 泌一种小分子信号，这种小分子物质可以诱导rpfF突变体恢复胞外蛋白酶的产生，并将这种 信号小分子定义为DSF，而且他们认为DSF就是小分子的脂肪酸类化合物。Slater等通过大 量实验，建立了稳定、灵敏和方便的DSF检测方法。2001年，张炼辉研究DSF的化学结构和 生物学功能。2004年，Wang等从rpfC突变体培养物的上清液中分离纯化出了一个DSF，为 (Z)-11-甲基-2-十二碳烯酸。He等从水稻白叶枯菌培养物上清液中分离和纯化得到了两个 新的BDSF、CDSF化合物，惊喜的是BDSF、CDSF具有与DSF相类似的生物活性，由此提出了 “DSF信号家族”的概念。2013年，Beaulieu等人发现了一种新的“DSF信号家族”成员(Z) -甲基-2-十四碳烯酸。
柑橘溃疡病(citrus canker)是影响世界柑橘生产的重要检疫性病害，对柑橘产业造成 了重大的影响。其致病菌为地毯草黄单胞杆菌柑橘致病变种(Xanthomonasaxonopodis pv.citri，Xac)，严重威胁柑橘生产，目前化学防治是治疗柑橘溃疡病的主要措施，主要有 波尔多液硫酸铜、波美度的石硫合剂、72％农用链霉素、3％金核霉素水剂、可杀得等。这些农 药的大量使用已经带来了环境污染、生态平衡破坏和食品安全等一系列问题，严重威胁到人 类健康。
发明内容
筛选DSF信号结构类似物，利用他们干扰或拮抗DSF群体效应，降低致病因子的表达， 从而达到控制柑橘溃疡病的传播，这是治疗防治柑橘溃疡病的一种新思路。本发明涉及从柑 橘溃疡病菌Xac(Xanthomonas axonopodis pv.citri)中发现两个新群体感应DSF信号分 子((Z)-12-甲基-2-十四碳烯酸(FDSF)，(Z)-13-甲基-2-十四碳烯酸(GDSF))，经提取分 离、生物活性测定和化学结构鉴定以及与化学合成结构对比确定，属于生物与化学交叉领域。
本发明提供的用于防治柑橘溃疡病的化合物，其结构式为：
其中，R1为H+或CH3 +中的一种，R1为H+或CH3 +中的一种。
上述的用于防治柑橘溃疡病的化合物，其结构式为：
上述的用于防治柑橘溃疡病的化合物，其结构式为：
上述各项提供的用于防治柑橘溃疡病的化合物在制备预防柑橘溃疡病药物中的应用。
本发明的有益技术效果是：本发明提供的化合物能够有效干扰或拮抗DSF群体效应，降 低致病因子的表达，从而达到控制柑橘溃疡病的传播，治疗防治柑橘溃疡病。
附图说明
图1制备EDSF、FDSF和GDSF的流程示意图；
图2三种活性组分HPLC；其中，E为EDSF，F为化合物FDSF，G为GDSF；
图3 FDSF的HRMS；
图4 FDSF的CNMR；
图5 FDSF的HNMR；
图6 FDSF的HMQC；
图7 FDSF的HMBC；
图8 FDSF的COSY；
图9 GDSF的HRMS；
图10 GDSF的CNMR；
图11 GDSF的HNMR；
图12 GDSF的HMQC；
图13 GDSF的HMBC；
图14 GDSF的COSY；
图15 EDSF、FDSF和GDSF的生物活性的考察。
具体实施方式：
实施例1
(1)DSF提取分离方法路线
乙酸乙酯萃取(3*10mL)RPFC突变的Xac[地毯草黄单胞杆菌柑橘致病变种(Xanthomonas axonopodis pv.citri,Xac)]培养上清液，通过半制备色谱分离，得到三种活性馏分分别给 名为EDSF、FDSF、GDSF。FDSF与GDSF通过G60硅胶薄层色谱进一步纯化(洗脱剂：正己烷/ 乙酸乙酯＝10/1)，收集具有紫外荧光活性的馏分，具体如图1所示。
三种DSF的活性通过洗脱剂后，使用DSF传感器FE58监控。该三活性组分在210nm条件下，通过HPLC测试(附图2)。
FDSF、GDSF的结构通过ESI-MS、1H NMR、13C NMR、HMBC、HMQC、COSY等进行表征，具体如图3-14所示。经过检测确认EDSF的化学结构是：
FDSF的化学结构是：
GDSF的化学结构是：
(2)DSF信号分子活性检测
称40mg X-gluc溶于1mL DMSO中制备成X-gluc溶液，然后将制备的X-gluc溶液(400 μl/100ml)和OD600为2.0的FE58报告菌株(2ml/100ml)加到42℃左右的NYG固体培养基中，倒入培养皿静置15min冷凝至固化，点上样品在倒好的培养皿中，遮光后水平放置在28℃培养箱约36小时，培养观察蓝圈大小；具体如图15所示。生物活性是以下图的蓝光圈大小来表征的。光圈越大表示生物活性越好，FDSF和GDSF的生物活性都比EDSF强，其中FDSF的生物活性最强。验证了本发明提供的两种化合物能够有效干扰或拮抗DSF群体效应，降低致病因子的表达，从而达到控制柑橘溃疡病的传播，治疗防治柑橘溃疡病。

Claims (4)

1.用于防治柑橘溃疡病的化合物，其特征在于：其结构式为：
其中，R1为H+或CH3 +中的一种，R1为H+或CH3 +中的一种。
2.根据权利要求1所述的用于防治柑橘溃疡病的化合物，其特征在于：其结构式为：
。
3.根据权利要求1所述的用于防治柑橘溃疡病的化合物，其特征在于：其结构式为：
。
4.权利要求1-3任一项所述的用于防治柑橘溃疡病的化合物在制备预防柑橘溃疡病药物中的应用。
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115650790A (zh) * 2022-10-14 2023-01-31 上海农乐生物制品股份有限公司 一种氨基酸水溶肥及其制备方法和用途

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