海洋来源单萜及衍生物的设计、合成和生物活性评价及四降二萜全合成的初步研究
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摘要
萜类化合物不仅是天然药物研究的重要领域,也是发现活性成分的重要的源泉。虽然萜类化合物具有相对简单的结构,但是却具有多种多样的生物活性。
     天然产物(+)-penicimonoterpene (PMT)是本课题组2011年分离于海藻来源的内生真菌Penicillium chrysogenum QEN-24S的单萜化合物,活性筛选表明(+)-PMT具有抑制白菜黑斑病菌的活性。本文通过四步反应以甲基庚烯酮为起始原料,通过Reformatsky反应构建基本的碳骨架首次全合成消旋的单萜化合物(±)-PMT。该方法具有合成路线简单、条件温和的特点,可同时获得结构多样的系列衍生物。共设计合成了24个衍生物,其中新化合物15个,并通过波谱手段(1H NMR,13C NMR, ESIMS和HRESIMS)进行了化合物的结构确认。对所有合成的目标化合物和衍生物进行了生物活性评价,包括抗细菌活性测试(大肠杆菌、金黄色葡萄球菌、藤黄微球菌、铜绿假单胞菌、溶藻弧菌、鳗弧菌、迟缓爱德华氏菌、嗜水气单胞菌、副溶血性弧菌和哈氏弧菌),抗真菌活性测试(白菜黑斑病菌、柑橘炭疽病菌、小麦赤霉病菌和小麦全蚀病菌)以及卤虫致死活性测试。部分化合物(T-22-139,T-34-141和T-33-140B)显示出了较好的抗细菌活性,尤其是抗海洋弧菌的活性,其活性优于阳性对照氯霉素,最小抑菌浓度范围为0.25–0.5μg/mL。部分化合物(T-14-108B,T-21-124,T-31-135和T-22-139)也显示出了较好的抗真菌活性。化合物T-14-108B对农业病害真菌小麦赤霉病菌具有较强的抑制活性,优于阳性对照128倍,且毒性较低,为寻找新型的低毒高效的抗农业病害菌的药物提供了依据。卤虫活性测试表明合成化合物毒性较低。对PMT和衍生物进行构效关系分析表明:修饰C-6/7的双键,或烯丙位甲基进行取代,或改变C-1位的羧基能显著提高抑菌活性。
     本文的另一部分工作是罗汉松内酯四降二萜类化合物wentilactones的全合成初步研究。该类化合物分离于海藻内生真菌Aspergillus wentii EN-48。通过烯丙位羟基氯代反应、氰基取代反应、氰基水解反应、羧基的保护、烯丙位氧化反应、氯代反应六步反应完成了烷基化前体的合成。为得到关键的关环前体奠定了基础。
     本论文对海洋来源的单萜PMT进行了全合成并设计合成24个系列衍生物,通过活性测试发现部分化合物活性优于阳性对照,尤其是抗海洋弧菌活性,为获得抗海洋弧菌药物提供了一定的依据。本论文对wentilactones系列化合物的全合成进行了初步研究,通过六步反应完成了烷基化前体的合成为得到关键的关环前体奠定了基础。
Terpenoids comprise an important class of bioactive agents. Despite their relativelysimple structures, some of these compounds exhibit interesting biological activities.
     We have recently reported the isolation and identification of a new monoterpenoid,penicimonoterpene (+)-1, from a marine-derived endophytic isolate of the fungusPenicillium chrysogenum QEN-24S. The first total racemic synthesis ofmarine-derived (±)-PMT has been achieved in four steps from6-methylhept-5-en-2-one using a Reformatsky reaction as the key step to construct thebasic carbon skeleton. This approach has the merits of low cost, mild reactionconditions, and easy access to diversity-oriented derivatives for potentialstructure-activity relationship (SAR) investigation. A total of24new derivatives of(±)-PMT have also been designed and synthesized. Their structures werecharacterized by analysis of their1H NMR,13C NMR and HRESIMS data. Some ofthem showed significant antibacterial activity against seven bacteria (Aeromonashydrophilia, Escherichia coli, Micrococcus luteus, Staphyloccocus aureus, Vibrioanguillarum, V. harveyi, and/or V. parahaemolyticus) and antifungal activity againstthree plant-pathogenic fungi (Alternaria brassicae, Colletotrichum gloeosporioides,and/or Fusarium graminearum). Notably, some of the derivatives (compoundsT-22-139, T-34-141, and T-33-140B) exhibited antimicrobial MIC values rangingfrom0.25to0.5μg/mL, which were stronger than those of the positive control. Somecompounds T-14-108B, T-21-124, T-31-135, and T-22-139also showed strongerantifungal activity. Compound T-14-108B showed extremely high selectively againstF. graminearum,128-fold more potent than amphotericin B, and might have potentialas an antifungal agent. SAR analysis of (±)-PMT and its derivatives indicated thatmodification of the carbon-carbon double bond at C-6/7, of groups on the allylicmethylene unit, and of the carbonyl group at C-1effectively enhanced antimicrobialactivity.
     Wentilactones, a kind of tetranorditerpenoids belonged to podolactones, wereisolated and identificated from the marine alga-derived endophytic fungus Aspergilluswentii EN-48. Six steps reactions (including chlorination at allylic hydroxyl group,cyano-substituted reaction, cyano hydrolysis reaction, carboxyl group protectionreaction, and allylic oxidation reaction) were finished to product alkylated precursor.It established the foundation to obtain cyclization precursor.
     This dissertation focused on synthesis of (±)-PMT and24related derivatives.Bioassay results revealed some compounds exhibited strong antibacterial activityagainst bacteria and plant-pathogenic fungi, which is much better than the positivecontrol, especially for marine Vibrio. The results may be helpful to the exploration ofpotential antibiotic for marine Vibrio. This dissertation also focused on preliminarystudy on total synthesis of tetranorditerpenoid. Alkylated precursor was finished aftersix steps reactions. It established the foundation to obtain cyclization precursor.
引文
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