WO2019237645A1 - 一种高活性的独脚金内酯衍生物及其制备与应用 - Google Patents

一种高活性的独脚金内酯衍生物及其制备与应用 Download PDF

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WO2019237645A1
WO2019237645A1 PCT/CN2018/114557 CN2018114557W WO2019237645A1 WO 2019237645 A1 WO2019237645 A1 WO 2019237645A1 CN 2018114557 W CN2018114557 W CN 2018114557W WO 2019237645 A1 WO2019237645 A1 WO 2019237645A1
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formula
compound represented
strigolactone
plant
promote
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闫建斌
李玉文
李素华
陈林海
南发俊
谢道昕
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清华大学
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/60—Two oxygen atoms, e.g. succinic anhydride
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom

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  • the invention relates to the fields of plant hormones and chemical synthesis, and in particular to a highly active strigolactone structural analog, and preparation and application thereof.
  • Strigolactones are a small class of terpenoid lactones and a new plant hormone. More than forty years ago, strigol was extracted from cotton root exudates for the first time, and it could induce the germination of striga and letang seeds. With the development of extraction and determination technology, nearly 20 kinds of SLs have been detected in plants. In addition to strigol, there are also Orbanchol, Sorgolactone, and so on. 5-Deoxystrigol was isolated from the root spines of Lotus japonicus as the first fungal branching factor and has been found in many monocotyledonous and dicotyledonous plants. Found in the plant.
  • SLs can be used as a new type of plant endogenous hormones, which play important roles in many aspects, including regulating plant morphogenesis and growth and development; controlling seed germination of parasitic weeds and regulating roots of bushes Germ germination and hypha elongation.
  • the SL signaling pathway is relatively clear.
  • the receptor protein D14 binds and hydrolyzes SLs, then forms a complex with MAX2 and SMXL6 / SMXL7 / SMXL8, and degrades the inhibitor SMXL6 / SMXL7 / through the ubiquitination degradation pathway.
  • SMXL8 thus activating the SL signaling pathway (Figure 1), inhibits plant branching after BRC1 is released.
  • SLs analogs The content of natural SLs in plants is extremely low and the structure is complex, which is difficult to obtain in large quantities by extraction or chemical synthesis. Therefore, the design and chemical synthesis of SLs analogs has become particularly important.
  • the most widely used and effective analog of SLs is GR24.
  • the existing GR24 synthesis route is mainly synthesized from 1-indanone.
  • the high production cost has limited its use in Scientific research and large-scale promotion and use in agricultural production.
  • the object of the present invention is to provide a strigolactone structural analog, a preparation method and an application field thereof.
  • the strigolactone structural analog SL1 provided by the present invention has the structural formula shown in Formula I:
  • strigolactone structural analog SL1 shown in the above formula I is prepared according to a method including the following steps:
  • the conditions of the bromination reaction are: using dibenzoyl peroxide (BPO) as an initiator, tetrachloromethane as a solvent, and N-bromosuccinimide (NBS) as bromine A chemical agent, under reflux conditions, causes the hydrogen at the 5-position of the compound represented by the formula A to undergo a bromination reaction to obtain the compound represented by the formula B.
  • BPO dibenzoyl peroxide
  • NBS N-bromosuccinimide
  • the molar ratio of the compound represented by Formula A to NBS may be 1: 0.8-1.2.
  • the time of the bromination reaction may be 1.5-3.5 h, and specifically may be 2 h.
  • step 2) of the above method the molar ratio of the compound represented by Formula B to the 2-nitrophenol represented by Formula C may be: 1: 1-1.5.
  • the condensation reaction is performed in the presence of an inorganic base and a phase transfer catalyst.
  • the inorganic base may be potassium carbonate, and the phase transfer catalyst may be tetrabutylammonium bromide.
  • the condensation reaction is performed at room temperature, and the time of the condensation reaction may be 1-24h.
  • the plant may specifically be Arabidopsis thaliana.
  • the parasitic weeds can be specifically listed.
  • the present invention also provides a plant growth regulator, which contains the strigolactone structural analog SL1 of the above formula I.
  • the present invention provides a strychium analogue with simple structure, convenient synthesis and high biological activity.
  • the analogue can be applied to the following aspects: 1) Regulating the growth and development of Arabidopsis thaliana: inhibiting branching and inhibiting embryos Axial elongation, inhibition of lateral root formation, promotion of root hair growth, promotion of leaf senescence, etc .; 2) promotion of germination of parasitic weed (Letang) seeds; 3) promotion of elongation of arbuscular mycelium.
  • FIG. 1 is a synthetic scheme of preparing a strigolactone structural analog SL1 shown in Formula I in the present invention.
  • Figure 2 is a schematic diagram of the SL signaling pathway in Arabidopsis, cited from Wang, L. et al. (2015) Strigolactone Signaling in Arabidopsis Regulates Shooting Development Targeting D53-Like SMXL Repressor Proteins for Ubiquitination and Degradation. 27 (11) 3128-3142.
  • Figure 3 shows the structural formula of naturally occurring SLs and their synthetic analog GR24.
  • FIG. 4 shows that SL1 promotes the interaction between Arabidopsis SMXL7 and AtD14 in the present invention.
  • Figure 5 shows that SL1 inhibits hypocotyl length in Arabidopsis thaliana in the present invention.
  • strigolactone structural analog SL1 of formula I was prepared according to the synthetic scheme shown in FIG. 1.
  • the raw material lactone 1 (0.79 g, 8.05 mmol) was dissolved in CCl 4 (39 mL), and NBS (1.58 g, 8.8 mmol) and BPO (20 mg, 0.083 mmol) were sequentially added under stirring at room temperature, followed by heating under reflux for 2 hours.
  • the reaction solution was filtered, the filter cake was washed with CCl 4 , and the filtrate was concentrated to give a pale yellow oily substance 2.
  • Bromide 2 was dissolved in DCM (32 mL), and 2-nitrophenol (1.12 g, 8.05 mmol), tetrabutylammonium bromide (2.59 g, 8.05 mmol), and potassium carbonate (1.33 g, 9.62 mmol) were sequentially added under stirring at room temperature. ) Aqueous solution (24 mL) and reacted at room temperature overnight. The reaction solution was diluted with EtOAc, and the organic phase was washed with water, saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product.
  • the pull down concentration gradient experiment shows that as the concentration increases, the promoting effect of SL1 on the interaction between AtD14 and SMXL7 protein is gradually enhanced, that is, concentration-dependent.
  • 1 ⁇ M SL1 is similar to 5 ⁇ M GR24; 5 ⁇ M SL1 is similar to 10 ⁇ M GR24; 10 ⁇ M SL1 is similar to 20 ⁇ M GR24. Therefore, in promoting the interaction between AtD14 and SMXL7 proteins, the intensity of SL1 is about 2-5 times that of GR24.
  • Example 3 SL1 inhibits elongation of hypocotyls in Arabidopsis
  • MS medium (0.6% agar) (1L formula): 4.43 g of MS powder (Phytotechlab), 20 g of sucrose, 6 g of agar, pH 5.9-6.0. High-pressure steam sterilization at 121 ° C for 15min.
  • Col-0 and max2-3 (SALK_092836) were spread in MS medium supplemented with GR24 or SL1 at 0, 1, 3, 5, 10 ⁇ M, and protected from light for 3 days at 4 ° C.
  • SL1 inhibits the hypocotyl elongation of Arabidopsis wild-type Col-0, but cannot inhibit the hypocotyl elongation of the SL-insensitive mutant max2-3; with the increase of SL1 concentration, the inhibitory effect stronger.
  • the inhibitory effect of SL1 on hypocotyls is concentration-dependent and depends on MAX2.
  • the inhibitory effect of SL1 was significantly stronger than that of GR24 at the same concentration (p ⁇ 0.01); the inhibitory intensity of 1 ⁇ M SL1 on hypocotyl was similar to that of 5 ⁇ M GR24; the inhibitory intensity of SL1 on hypocotyl 10 ⁇ M and GR24 was similar. Therefore, in terms of inhibiting hypocotyl elongation in Arabidopsis thaliana, the inhibitory intensity of SL is about 3-5 times that of GR24.
  • SL1 can be used to regulate plant growth and plant type, and grow and develop in the best state.

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Abstract

本发明提供一种独脚金内酯结构类似物及其制备方法与应用。结构式如式I所示。本发明所提供的独脚金内酯结构类似物在调控植物生长发育、促进寄生杂草种子萌发和促进丛枝根菌菌丝伸长等方面具有重要作用。天然独脚金内酯的分子结构复杂，人工合成成本高昂。因此，设计和合成独脚金内酯的结构类似物具有重要的科学和应用价值。本发明报道了一种结构简单且生物活性高的独脚金内酯结构类似物的制备及应用。

Description

一种高活性的独脚金内酯衍生物及其制备与应用 技术领域
本发明涉及植物激素和化学合成领域，具体涉及一种高活性的独脚金内酯结构类似物及其制备与应用。
背景技术
独脚金内酯(Strigolactones，SLs)是一类萜类内酯小分子，是一种新型植物激素。在四十多年前，人们第一次从棉花根系分泌物中提取到了独脚金醇(Strigol)，可以诱导独脚金、列当种子萌发。随后随着提取及测定技术的发展，目前植物体内已经检测出近20种SLs，除独脚金醇(Strigol)以外，还有列当醇(Orbanchol)、高粱内酯(Sorgolactone)等。5-脱氧独脚金醇(5-Deoxystrigol)是作为第一个真菌分枝因子从百脉根(Lotus japonicus)根刺分泌物中分离得到的，并已经在单子叶植物和双子叶植物的多种植物中发现。
经过不断地科学研究，证明了SLs能够作为一种新型的植物内源激素，在多个方面发挥重要作用，包括调控植物的形态建成及生长发育；控制寄生杂草的种子萌发和调控丛枝根菌的萌发和菌丝伸长等。
目前SL信号通路已经较为清晰，以调控分枝为例：受体蛋白D14结合并水解SLs，随后与MAX2和SMXL6/SMXL7/SMXL8形成复合体，通过泛素化降解途径降解抑制子SMXL6/SMXL7/SMXL8，从而激活SL信号通路(图1)，如BRC1被释放后抑制植物分枝。
天然SLs在植物体内含量极低，结构复杂，难以通过提取或化学合成的方式大量获得。因此，SLs类似物的设计与化学合成变得尤为重要。目前，应用最广泛和有效的SLs类似物是GR24，现有的GR24合成路线主要以1-茚酮为原料合成，但由于合成中间步骤多和产率低，导致生产成本高，限制了其在科学研究以及农业生产中的大规模推广和使用。
因此，迫切需要找到一种结构简单、合成便捷、生物活性高的新的独脚金内酯结构类似物。
发明公开
本发明的目的是提供一种独脚金内酯结构类似物、制备方法和应用领域。
本发明所提供的独脚金内酯结构类似物SL1，其结构式如式I所示：
Figure PCTCN2018114557-appb-000001
上述式I所示独脚金内酯结构类似物SL1按照包括下述步骤的方法制备得到：
1)使得式A所示化合物5-位上的氢发生溴代反应，得到式B所示化合物；
Figure PCTCN2018114557-appb-000002
2)使得式B所示化合物与式C所示2-硝基苯酚发生缩合反应，得到式I所示化合物，
Figure PCTCN2018114557-appb-000003
上述方法步骤1)中，所述溴代反应的条件为：以过氧化二苯甲酰(BPO)为引发剂，四氯甲烷为溶剂，N-溴代丁二酰亚胺(NBS)为溴化剂，回流条件下，使得式A所示化合物5-位上的氢发生溴代反应得到式B所示化合物。
式A所示化合物与NBS摩尔比可为：1：0.8-1.2。
所述溴代反应的时间可为1.5-3.5h，具体可为2h。
上述方法步骤2)中，式B所示化合物与式C所示2-硝基苯酚的摩尔比可为：1：1-1.5。
所述缩合反应在无机碱、相转移催化剂存在下进行。
所述无机碱具体可为碳酸钾，所述相转移催化剂具体可为四丁基溴化铵。
所述缩合反应在室温下进行，所述缩合反应的时间可为1-24h。
上述式I所示独脚金内酯结构类似物SL1在下述方面的应用也属于本发明的保护范围：
1)促进AtD14与SMXL7或者MAX2之间的互作；
2)抑制植物幼苗下胚轴的伸长；
3)促进植物的根毛生长；
4)抑制植物的侧根生成；
5)抑制植物的分枝发育；
6)促进植物叶片的衰老；
7)促进寄生杂草种子萌发；
8)促进从枝菌根真菌菌丝的生长。
所述植物具体可为拟南芥。
所述寄生杂草具体可为列当。
本发明还提供一种植物生长调节剂，含有上述式I所示独脚金内酯结构类似物SL1。
本发明提供了一种结构简单、合成便捷、生物活性高的独脚金类似物，同时，该类似物能够应用于以下方面：1)调控拟南芥的生长发育：抑制分枝、抑制下胚轴伸长、抑制侧根生成、促进根毛生长、促进叶片衰老等方面；2)促进寄生杂草(列当)种子萌发；3)促进丛枝根菌菌丝的伸长。
附图说明
图1为本发明中制备式I所示独脚金内酯结构类似物SL1的合成路线图。
图2为拟南芥中SL信号传导通路示意图，引用自Wang,L.et al.(2015)Strigolactone Signaling in Arabidopsis Regulates Shoot Development by Targeting D53-Like SMXL Repressor Proteins for Ubiquitination and Degradation.The Plant Cell Nov 2015,27(11) 3128-3142。
图3为天然存在的SLs及其合成类似物GR24的结构式。
图4表示本发明中SL1促进拟南芥SMXL7与AtD14之间的互作。
图5表示本发明中SL1抑制拟南芥下胚轴长度。
实施发明的最佳方式
下述实施例中的实验方法，如无特别说明，均为常规方法
实施例1、式I所示独脚金内酯结构类似物SL1的制备
按照图1所示的合成路线图制备式I所示独脚金内酯结构类似物SL1。
原料内酯1(0.79g，8.05mmol)溶于CCl 4(39mL)，室温搅拌下依次加入NBS(1.58g，8.8mmol)、BPO(20mg，0.083mmol)，加热回流2小时。反应液过滤，滤饼用CCl 4洗涤，滤液浓缩得浅黄色油状物2。
溴代物2溶于DCM(32mL)，室温搅拌下依次加入2-硝基苯酚(1.12g，8.05mmol)、四丁基溴化铵(2.59g，8.05mmol)和碳酸钾(1.33g，9.62mmol)的水溶液(24mL)，室温反应过夜。反应液用EtOAc稀释，有机相依次用水洗、饱和食盐水洗涤、无水硫酸钠干燥、过滤、浓缩得粗品。粗品经硅胶柱层析(PE/DCM＝1/1～DCM洗脱)得乳白色固体SL1(1.253g，66.2％)。 1H NMR(300MHz,CDCl 3):δ7.88(d,J＝8.1Hz,1H),7.61(t,J＝7.2Hz,1H),7.51(d,J＝8.4Hz,1H),7.27(t,J＝7.2Hz,1H),7.08(s,1H),6.30(s,1H),2.03(s,3H)； 13C NMR(75MHz,CDCl 3):δ173.1,147.8,142.2,140.4,137.6,135.7,126.3 124.4,121 3,102.7,12.5；ESI-MS(m/z):258.1[M+Na] +。
实施例2、SL1促进拟南芥SMXL7与AtD14之间的互作
1)取20ml 6×His-Flag-SMXL7的昆虫细胞培养液，离心后弃上清，用1mL buffer(50mM Tris-HCl pH7.0，150mM NaCl，0.5％Tween 20)重悬细胞沉淀。
2)破碎细胞：液氮-常温水反复冻融三次。冻融结束后离心(4℃， 最大转速离心10分钟)。
3)离心结束后，取上清和Flag胶(Sigma)孵育结合，条件为：4℃，1h。
4)反应结束后，用buffer洗涤未结合的蛋白，然后加入10μg GST-D14和0、1、3、5、10μM的GR24和SL1进行孵育，条件为：25℃，1h。
5)反应结束后，弃去上清，并用buffer洗涤未结合的蛋白。取120uL 0.2mg/ml flag peptide竞争洗脱，条件为：4℃，30min。
6)反应结束后，短暂离心。取上清100uL加入25ul 5×loading buffer，混匀后，煮样：100℃，5min。
7)Western blot检测：anti-GST抗体(Abmart)用来检测AtD14蛋白，SMXL7蛋白作为loading control(结果见图4)。
由图4可知:pull down浓度梯度实验表明，随着浓度的提高，SL1对AtD14与SMXL7蛋白互作的促进作用逐渐增强，即浓度依赖性。1μM SL1作用强度与5μM GR24类似；5μM SL1作用强度与10μM GR24类似；10μM SL1作用强度与20μM GR24类似。因此，在促进AtD14与SMXL7蛋白互作方面，SL1的作用强度约为GR24的2-5倍。
实施例3、SL1抑制拟南芥下胚轴的伸长
1)MS培养基(0.6％agar)的制备(1L配方)：4.43gMS粉(Phytotechlab)，20g蔗糖，6g琼脂，pH 5.9-6.0。高压蒸汽灭菌121℃，15min。
2)将Col-0和max2-3(SALK_092836)的种子铺在添加了0、1、3、5、10μM的GR24或SL1的MS培养基中，4℃避光三天。
3)取出平板，放于植物房中生长7天，条件为：弱光全光照，18-22℃。
4)将幼苗拔出，摆在1％琼脂板上，扫描成图片格式，用Digimizer软件测量不同处理下幼苗的下胚轴长度，并用SPSS软件的ANOVA法进行显著性分析(结果见图5)。
由图5可知：SL1抑制拟南芥野生型Col-0的下胚轴的伸长，但不能抑制SL不敏感突变体max2-3的下胚轴伸长；随着SL1浓度的增加，抑制 作用越来越强。说明SL1对下胚轴的抑制作用具有浓度依赖性并且依赖于MAX2。另外，SL1的抑制作用显著强于同等浓度的GR24(p<0.01)；1μM SL1对下胚轴的抑制强度与5μM GR24类似；3μM SL1对下胚轴的抑制强度10μM GR24类似。因此，在抑制拟南芥下胚轴伸长方面，SL的抑制强度约为GR24的3-5倍。
工业应用
1、诱导寄生杂草“自杀性”萌发：在没有寄主的情况下，喷施独脚金内酯类似物SL1，诱导寄生杂草种子的萌发，但由于附近没有寄主，杂草种子萌发后只能存活很短时间，即“自杀性”萌发，从而达到除寄生性杂草的目的。
2、调控植物生长发育：独脚金内酯调控植物分枝进而调控株型；促进植物与丛枝菌根真菌的共生，增强植物对矿质营养元素的吸收(尤其在土壤贫瘠时，如低磷条件，植物产生更多SL)。因此可以应用SL1来调节植物的生长和株型，以最好的状态生长发育。

Claims (9)

  1. 式I所示化合物：
    Figure PCTCN2018114557-appb-100001
  2. 制备权利要求1中式I所示化合物的方法，包括：
    1)使得式A所示化合物5-位上的氢发生溴代反应，得到式B所示化合物；
    Figure PCTCN2018114557-appb-100002
    2)使得式B所示化合物与式C所示2-硝基苯酚发生缩合反应，得到式I所示化合物，
    Figure PCTCN2018114557-appb-100003
  3. 根据权利要求2所述的方法，其特征在于：步骤1)中，所述溴代反应的条件为：以BPO为引发剂，四氯甲烷为溶剂，NBS为溴化剂，回流条件下，使得式A所示化合物5-位上的氢发生溴代反应得到式B所示化合物；
    式A所示化合物与NBS摩尔比为：1：0.8-1.2；
    所述溴代反应的时间为1.5-3.5h。
  4. 根据权利要求2或3所述的方法，其特征在于：步骤2)中，式B所示化合物与式C所示2-硝基苯酚的摩尔比为：1：1-1.5；
    所述缩合反应在无机碱、相转移催化剂存在下进行；
    所述无机碱具体可为碳酸钾，所述相转移催化剂具体可为四丁基溴化铵；
    所述缩合反应在室温下进行，所述缩合反应的时间为1-24h。
  5. 权利要求1所述的式I所示化合物作为植物激素的应用。
  6. 根据权利要求5所述的应用，其特征在于：所述植物激素是指与天然独脚金内酯类似物的功能相同或近似的植物激素。
  7. 根据权利要求5或6所述的应用，其特征在于：所述应用为下述方面的应用：
    1)促进AtD14与SMXL7或者MAX2之间的互作；
    2)抑制植物幼苗下胚轴的伸长；
    3)促进植物的根毛生长；
    4)抑制植物的侧根生成；
    5)抑制植物的分枝发育；
    6)促进植物叶片的衰老；
    7)促进寄生杂草种子萌发；
    8)促进从枝菌根真菌菌丝的生长。
  8. 根据权利要求7所述的应用，其特征在于：所述植物为拟南芥；所述寄生杂草为列当。
  9. 一种植物生长调节剂，含有权利要求1所述的式I所示化合物。
PCT/CN2018/114557 2018-06-15 2018-11-08 一种高活性的独脚金内酯衍生物及其制备与应用 WO2019237645A1 (zh)

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