CN108409533A - 一种灰毡毛忍冬二萜类化合物及其制备方法和抗农业真菌用途 - Google Patents

一种灰毡毛忍冬二萜类化合物及其制备方法和抗农业真菌用途 Download PDF

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CN108409533A
CN108409533A CN201810320150.9A CN201810320150A CN108409533A CN 108409533 A CN108409533 A CN 108409533A CN 201810320150 A CN201810320150 A CN 201810320150A CN 108409533 A CN108409533 A CN 108409533A
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陈雨
冯煦
吕慧
徐曙
单宇
赵友谊
王鸣
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Abstract

本发明涉及天然产物领域。具体涉及以灰毡毛忍冬的根为原料，通过天然产物化学方法提取分离，得到的一种新化合物灰毡毛忍冬甲素（lonimacranthoidin A），其骨架属于syn‑海松烷型（syn‑pimarane）二萜，该化合物对农业病原真菌具有较强抑制作用，可用于制备抗农业病原真菌药物。

Description

一种灰毡毛忍冬二萜类化合物及其制备方法和抗农业真菌 用途
技术领域
本发明涉及天然产物领域。其特征是以灰毡毛忍冬(Lonicera macranthoidesHand.-Mazz.)的根为原料，通过天然产物化学方法提取分离，得到的一种新化合物，其骨架属于syn-海松烷型(syn-pimarane)二萜，该化合物对农业病原真菌具有较强抑制作用，可用于制备抗农业病原真菌药物。
背景技术
我国是农业大国，农药是防治农业病害的主要工具。传统化学农药通常选择性差、毒性大、残留时间长，在使用过程中存在农药残留严重、危害人畜健康、污染环境等问题。生物农药是指那些由植物提取物、微生物活体或微生物产生的代谢产物制成的具有农药属性的产品，由于源自生物，不论其组成和结构如何复杂，归根结底是由碳水化合物等经不同途径代谢而来，因而其组成通常是碳、氢、氧、氮四种元素，偶见其它元素。生物农药通常容易降解，进入自然界的碳、氮循环，对环境没有太多污染。开发高效低毒生物农药新品种对我国农业生产具有十分重要的意义。
海松烷型二萜为三环二萜，具有抗氧化、抗肿瘤、抗炎、抗菌等多种生物活性。尤其是，近年来研究表明syn-海松烷型二萜是水稻抗稻瘟病植保素，对稻瘟病菌有很好的抗菌活性，是一类很重要的抗菌素(Lee,C.W.,Yoneyama,K.,Takeuchi,Y.,Konnai,M.,Tamogami,S.,Kodama,O.,1999.Momilactones A and B in rice straw harvested atdifferent growth stages.Biosci.Biotech.Bioch.,63,1318–1320；Nozaki,H.,Hayashi,K.I.,Nishimura,N.,Kawaide,H.,Matsuo,A.,Takaoka,D.,2007.Momilactone A and B asallelochemicals from moss Hypnum plumaeforme:first occurrence inbryophytes.Biosci.Biotechnol.Biochem.,71,3127-3130.)，引起了广泛关注。
发明内容
本发明目的是提供一种新的海松烷型二萜类化合物，以及其制备方法和在抗农业病原真菌药物中的用途。
本发明采用的技术方案是：一种下列结构式的新海松烷型二萜类化合物，命名为灰毡毛忍冬甲素(lonimacranthoidin A)，其特征在于化学名为9,10-syn-2β,3β,15R,16-四羟基海松-7-烯，化学结构式为：
灰毡毛忍冬甲素(lonimacranthoidin A)。
进一步，所述的二萜类化合物灰毡毛忍冬甲素(lonimacranthoidin A)，按如下方法制备：以灰毡毛忍冬(Lonicera macranthoides Hand.-Mazz.)的根为原料，经用5～6倍原料体积的醇、水或其混合物回流提取2-3次，每次1-2小时，合并提取液，合并提取液，减压浓缩至0.5-1.5倍原料量体积，按1：1～3体积加入石油醚和乙酸乙酯依次分别萃取；乙酸乙酯萃取物经柱层析分离而得。柱层析用担体选自硅胶、凝胶、反相硅胶中的一种或几种；有机溶剂包括甲醇、乙醇、石油醚、乙酸乙酯；提取温度低于100℃。
进一步，灰毡毛忍冬甲素对水稻纹枯病菌(Rhizoctonia solani)和小麦赤霉病菌(Fusarium graminearum)有效中浓度(EC50)分别为：20.07±4.90μg mL-1，62.86±23.51μgmL-1。本发明为抗农业病原真菌药物筛选提供了新的先导化合物。
附图说明
图1为化合物灰毡毛忍冬甲素(lonimacranthoidin A)的关键1H-1H COSY相关情况和HMBC相关情况。
图2为化合物灰毡毛忍冬甲素(lonimacranthoidin A)的X-射线单晶衍射图。
具体实施方式
实施例1：将晾干的灰毡毛忍冬根5kg切成0.2～0.3cm每段，加入6倍生药体积的95％乙醇，回流提取2次，每次2h，合并粗提液，70℃减压浓缩至0.5倍药材量体积，再按1：2体积依次加入石油醚和乙酸乙酯分别萃取3次，合并石油醚和乙酸乙酯萃取液，减压浓缩，得到石油醚萃取物14g和乙酸乙酯萃取物200g。取乙酸乙酯萃取物，用硅胶柱层析分段，以石油醚-乙酸乙酯(20:1)、石油醚-乙酸乙酯(10:1)、石油醚-乙酸乙酯(4:1)、石油醚-乙酸乙酯(1:1)溶液洗脱，合并组分相似的洗脱液，浓缩后得F2-1～F2-4共4个部分。再综合运用硅胶柱层析、凝胶LH-20柱层析、重结晶等方法，从F2-2部分分离得到化合物灰毡毛忍冬甲素(150mg)，得率为0.003％。再综合运用各种波谱技术(MS,NMR,UV,IR)和X-射线单晶衍射技术，鉴定化合物灰毡毛忍冬甲素的结构。
化合物灰毡毛忍冬甲素的理化性质及波谱数据：化合物灰毡毛忍冬甲素为无色透明针状晶体(乙醇)，TLC紫外无暗斑且斑点无荧光，香草醛-浓硫酸试液加热显紫色，放置后颜色变浅消失。Liebermann-Burchard反应阳性。溶于甲醇、丙酮，提示为萜类化合物。HR-ESI-MS(m/z)：[M+H]+at m/z 361.2514(calculated:361.2510for[C20H34O4+H]+)，结合13C-NMR和DEPT谱推断分子式为C20H34O4，分子量338，不饱和度为4。
化合物灰毡毛忍冬甲素的1H NMR显示其有一个双键氢信号δH 5.32(1H,m,H-7)，4个甲基氢信号δH 0.78(3H,s,H3-17)，δH 1.00(3H,s,H3-18)，δH 1.08(3H,s,H3-19)，δH 1.17(3H,s,H3-20),两个氧化亚甲基信号δH 3.70(1H,dd,J＝2.7,11.1Hz,H-16a)，δH 3.43(1H,dd,J＝8.8,11.1Hz,H-16b)，三个氧化次甲基信号δH 4.08(1H,q,J＝3.4Hz,H-2)，δH 3.11(1H,d,J＝3.4Hz,H-3)，δH 3.24(1H,dd,J＝8.8,2.7Hz,H-15)，以及其他重叠的亚甲基，次甲基信号(δH 1.30-2.10)。其13C-NMR和DEPT谱显示其有两个双键碳信号δC 121.0(C-7)，δC137.8(C-8)，四个甲基碳信号δC 18.6(C-17)，δC 30.5(C-18)，δC 18.0(C-19)，δC 24.5(C-20)，五个亚甲基碳信号δC 40.8(C-1)，δC 24.4(C-6)，δC 26.0(C-11)，δC 35.3(C-12)，δC46.5(C-14)，一个氧化的亚甲基信号δC 63.8(C-16)，两个次甲基信号δC 44.8(C-5)，δC55.0(C-9)，三个氧化的次甲基信号δC 72.9(C-2)，δC 79.7(C-3)，δC 82.1(C-15)，以及三个季碳信号δC 39.1(C-4)，δC 35.6(C-10)，δC 40.4(C-13)。以上这些信息可以推测化合物I-1是拥有一个三取代的双键(△7)和四个羟基(OH-2，OH-3，OH-15，OH-16)的三环二萜。在1H-1HCOSY谱(图1)中，我们可以得到5个自旋体系：H-1/H-2/H-3；H-5/H-6/H-7；H-9/H-11/H-12；H-14；H-15/H-16。结合HMBC谱(图1)信号H3-17与C-12，C-13，C-14，C-15；H3-18与C-19，C-3，C-4，C-5；H3-19与C-18，C-3，C-4，C-5；H3-20与C-10，C-1，C-9，C-5；H-14与C-7，C-8，C-9，C-13，将5个自旋体系相连。通过2D-NMR进一步归属化合物灰毡毛忍冬甲素二萜片段的1H、13C-NMR数据(表1)，发现该片段结构与已知化合物16-O-acetyldarutigenol(Wang,F.,Cheng,X.L.,Li,Y.J.,Shi,S.,Liu,J.K.,2009.ent-Pimarane diterpenoids from Siegesbeckiaorientalis and structure revision of a related compound.J.Nat.Prod.,72,2005-2008.)相似，其母核为海松烷型二萜。
表1.化合物灰毡毛忍冬甲素的核磁共振波谱数据
a.Data were measured at 300MHz for 1H and 75MHz for 13C in methanol-d4,δinppm,J in Hz
b.Overlapped signal,assignments were done by HSQC,HMBC,and COSYexperiments。
化合物灰毡毛忍冬甲素相对构型的确定，ROESY上显示H-2，H-3，H3-18，H-5相关，为了进一步确证灰毡毛忍冬甲素的结构，对其进行单晶X-射线衍射。其晶体结构如图2，与核磁波谱解析的结构一致。至此，化合物灰毡毛忍冬甲素的绝对构型已确定，命名为9,10-syn-2β,3β,15R,16-四羟基海松-7-烯(9,10-syn-2β,3β,15R,16-tetrahydroxypimar-7-ene)。
UPLC-HRESI-MS法测定化合物灰毡毛忍冬甲素的纯度，色谱条件为：色谱柱C18(Zorbax SB C18，4.6×100mm，1.8μm)，柱温：25℃，流动相：乙腈-水(含0.1％甲酸)梯度洗脱(0～10min乙腈浓度由5％变化至10％，10～20min乙腈浓度为10％，20～40min乙腈浓度10％变化至23％，40～70min乙腈浓度由23％变化至38％，70～90min乙腈浓度由38％变化至50％，90～100min乙腈浓度为100％)，流速：0.3mL min-1，进样量：5μl；质谱检测器为6530ESI Q-TOF MS(Agilent,USA)，检测检测模式为阴离子，检测范围为m/z 100–1700。化合物灰毡毛忍冬甲素的保留时间为61.5min，按面积归一化法计算化合物灰毡毛忍冬甲素的纯度为98.9％。
实施例2：将晾干的灰毡毛忍冬根5kg切成0.2～0.3cm每段，加入5倍生药体积的甲醇，回流提取3次，每次1.5h，合并粗提液，50℃减压浓缩至0.5倍药材量体积，再按1：1体积依次加入石油醚和乙酸乙酯分别萃取3次，合并石油醚和乙酸乙酯萃取液，减压浓缩，得到石油醚萃取物16g和乙酸乙酯萃取物220g。再综合运用硅胶柱层析、凝胶LH-20柱层析、重结晶等方法，从乙酸乙酯萃取物中分离得到化合物灰毡毛忍冬甲素(160mg)，得率为0.0032％，UPLC-HRESI-MS检测产物的纯度为98.8％。
实施例3：将晾干的灰毡毛忍冬根10kg切成0.2～0.3cm每段，加入6倍生药体积的80％甲醇/水，回流提取2次，每次2h，合并粗提液，50℃减压浓缩至1.5倍药材量体积，再按1：2体积依次加入石油醚和乙酸乙酯分别萃取5次，合并石油醚和乙酸乙酯萃取液，减压浓缩，得到石油醚萃取物和乙酸乙酯萃取物。再综合运用硅胶柱层析、凝胶LH-20柱层析、重结晶等方法，从乙酸乙酯萃取物中分离得到化合物灰毡毛忍冬甲素(315mg)，得率为0.00315％，UPLC-HRESI-MS检测产物的纯度为98.4％。
实施例4：将晾干的灰毡毛忍冬根10kg切成0.2～0.3cm每段，加入5倍生药体积的水，回流提取3次，每次2h，合并粗提液，减压浓缩至1.5倍药材量体积，再按1：2体积依次加入石油醚和乙酸乙酯分别萃取3次，合并石油醚和乙酸乙酯萃取液，减压浓缩，得到石油醚萃取物和乙酸乙酯萃取物。再综合运用硅胶柱层析、凝胶LH-20柱层析、重结晶等方法，从乙酸乙酯萃取物中分离得到化合物灰毡毛忍冬甲素(304mg)，得率为0.00304％，UPLC-HRESI-MS检测产物的纯度为98.1％。
实施例5：化合物灰毡毛忍冬甲素抗水稻纹枯病菌和小麦赤霉病菌活性测定。供试水稻纹枯病菌(Rhizoctonia solani)和小麦赤霉病菌(Fusarium graminearum)均为田间采集分离菌株。将化合物灰毡毛忍冬甲素和对照药剂甲基硫菌灵(mildothane)溶于DMSO，配制成浓度为10000μg/mL的母液，并用DMSO倍半稀释成7个系列浓度梯度待用。将母液或等体积DMSO加入加热融化并冷却至55℃的PSA培养基(马铃薯浸出液200g、琼脂16g、蔗糖20g、蒸馏水1000ml)中，混匀后倒入培养皿中制成含药平板，冷凝静置。用直径5mm的打孔器在预培养的菌落边缘打取菌碟，并接种至含药平板中间，重复3次。25℃恒温倒置培养至对照接近长满平板，十字交叉法测定菌落直径并计算抑制率。抑制率(％)＝(对照菌落直径﹣加药处理菌落直径)/对照菌落直径×100。菌落直径＝十字交叉法测定直径平均值-5mm。根据各浓度抑制率使用DPS v7.05计算毒力回归方程，得出化合物灰毡毛忍冬甲素的抑制有效中浓度(ED50)。测定结果如下表2。
表2.化合物灰毡毛忍冬甲素抗水稻纹枯病菌和小麦赤霉病菌活性(EC50，μg mL-1)
a.该值为平均标准偏差(±SD)。

Claims (4)

1.一种海松烷型二萜类化合物，命名为灰毡毛忍冬甲素(lonimacranthoidin A)，其特征在于化学名为9,10-syn-2β,3β,15R,16-四羟基海松-7-烯，化学结构式为：
灰毡毛忍冬甲素(lonimacranthoidin A)。
2.权利要求1所述的二萜类化合物的制备方法，其特征在于，包括以下步骤：以灰毡毛忍冬(Lonicera macranthoides Hand.-Mazz.)的根为原料，经用5～6倍原料体积的醇、水或其混合物回流提取2-3次，每次1-2小时，合并提取液，减压浓缩至0.5-1.5倍原料量体积，按1：1～3体积加入石油醚和乙酸乙酯依次分别萃取；乙酸乙酯萃取物经柱层析分离而得。
3.根据权利要求2所述的制备方法，其特征在于柱层析用担体选自硅胶、凝胶、反相硅胶中的一种或几种；有机溶剂包括甲醇、乙醇、石油醚、乙酸乙酯；提取温度低于100℃。
4.权利要求1所述的化合物在制备防治水稻纹枯病和小麦赤霉病药物中的用途。
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