Natural product-based semisynthesis and biological evaluation of thiol/ amino-Michael adducts of xanthatin derived from Xanthium strumarium as potential pesticidal agents
Natural product-based semisynthesis and biological evaluation of thiol/ amino-Michael adducts of xanthatin derived from Xanthium strumarium as potential pesticidal agents
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基于天然产物的苍耳黄素硫醇/氨基-迈克尔加合物作为潜在杀虫剂的半合成和生物学评价
DOI：
10.1016/j.bioorg.2020.103696
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发表时间：
2020
影响因子：
5.1
通讯作者：
Chun Yang
中科院分区：
文献类型：
--
作者：
Xiao-yan Zhi;Ling-yun Jiang;Ting Li;Li-li Song;Li-juan Wu;Hui Cao;Chun Yang
黄苷是一种天然的倍半萜内酯类化合物，是菊科植物黄菊的主要成分之一，具有许多重要的生物学性质。为了发现天然产物为基础的农药，合成了49个Michael型黄嘌呤巯基/氨基加合物，并对其结构进行了表征，同时对其杀虫活性进行了研究。其中化合物2c、2 h、2 i和2对番茄灰霉病菌（Botrytis cinerea）具有较强的抑制活性（IC 50分别为0.96、0.38、6.33和7.21 μg/mL），优于黄嘌呤和两种商品杀菌剂。化合物2 tan和2u对所有供试植物病原真菌均表现出广谱和优异的抗真菌作用，其IC 50值范围为7.21 - 75.88 μg/mL。化合物2a、2f、2l、2 m、2 v、7 c、7 e、7 h、7i和7 j对小菜蛾Plutella xylostellaLinnaeus有一定的杀虫活性。化合物2b、7 g和7 h对P.对小菜蛾的LC_（50）分别为14.04、10.00和11.95 mg/L。这些结果表明，巯基/氨基附加在C-13位的黄嘌呤可能会提高抗真菌和杀卵活性的衍生物。黄嘌呤的环外双键是其杀幼虫活性的关键。本工作为进一步设计、合成和结构修饰黄原胶内酯类倍半萜内酯类化合物，开发新型环保农药提供了重要的参考。
Xanthatin, a natural sesquiterpene lactone, occurs as one of the major constituents ofXanthiumplants (Compositae) and exhibits many important biological properties. To discover natural products-based pesticides, forty-nine Michael-type thiol/amino adducts of xanthatin were synthesized and characterized, while their pesticidal activities were investigated. Among them, compounds2c,2h,2i, and2texhibited more potent antifungal activity againstBotrytis cinerea(IC50= 0.96, 0.38, 6.33, and 7.21 µg/mL, respectively) than xanthatin and the two commercial fungicides. Compounds2tand2udisplayed broad-spectrum and excellent antifungal effects against all tested phytopathogenic fungi, while their IC50values ranged from 7.21 to 75.88 µg/mL. Compounds2a,2f,2l,2m,2v,7c,7e,7h,7i, and7jshowed moderate larvicidal activity againstPlutella xylostellaLinnaeus. Furthermore, compounds2b,7g, and7hdemonstrated significant ovicidal activity againstP. xylostellawith the LC50values of 14.04, 10.00, and 11.95 mg/L, respectively. These findings suggest that thiol/amino appended in the C-13 position of xanthatin may improve antifungal and ovicidal activities for the derivatives. It was also noticed that the exocyclic double bond of xanthatin is crucial for its larvicidal activity. This work also provides some important hints for further design, synthesis, and structural modification of the xanthanolides sesquiterpene lactones toward development of the new environmentally friendly pesticides for sustainable agricultural production.