中国农业科学 ›› 2025, Vol. 58 ›› Issue (22): 4673-4687.doi: 10.3864/j.issn.0578-1752.2025.22.009

• 植物保护 • 上一篇    下一篇

菌核青霉HY5中3,5-二甲基苔色酸类混源萜的结构及其除草活性

蔡海林1(), 黄馨瑢2, 曾维爱1, 彭治鑫2, 赵阿娟1, 薄纯斌1, 向世鹏1, 高鹏程3, 张成省2, 赵栋霖2()   

  1. 1 湖南省烟草公司长沙市公司,长沙 410011
    2 中国农业科学院烟草研究所/国家农业环境微生物种质资源库(山东)/青岛市农业微生物种业技术创新中心,山东青岛 266101
    3 山东临沂烟草有限公司,山东临沂 276001
  • 收稿日期:2025-08-12 接受日期:2025-09-27 出版日期:2025-11-16 发布日期:2025-11-21
  • 通信作者:
    赵栋霖,E-mail:
  • 联系方式: 蔡海林,E-mail:hailincai@126.com。
  • 基金资助:
    国家自然科学基金(32470420); 中国烟草总公司重大科技项目(110202401015(LS-05)); 青岛市自然科学基金原创探索项目(23-2-1-183-zyyd-jch)

Structure and Herbicidal Activity of 3,5-Dimethylorsellinic Acid-Derived Meroterpenoids from Penicillium sclerotiorum HY5

CAI HaiLin1(), HUANG XinRong2, ZENG WeiAi1, PENG ZhiXin2, ZHAO AJuan1, BO ChunBin1, XIANG ShiPeng1, GAO PengCheng3, ZHANG ChengSheng2, ZHAO DongLin2()   

  1. 1 Changsha Tobacco Company of Hunan Province, Changsha 410011
    2 Institute of Tobacco Research, Chinese Academy of Agricultural Sciences/National Agricultural Environmental Microbial Resource Bank (Shandong)/Qingdao Agricultural Microbial Seed Industry Technology Innovation Center, Qingdao 266101, Shandong
    3 Shandong Linyi Tobacco Co., Ltd., Linyi 276001, Shandong
  • Received:2025-08-12 Accepted:2025-09-27 Published:2025-11-16 Online:2025-11-21

摘要:

【背景】3,5-二甲基苔色酸(3,5-dimethylorsellinic acid,DMOA)类混源萜化学结构多样,生物活性广泛,然而对其农用生物活性鲜有报道。化学除草剂易造成杂草抗性增强并引发环境问题,亟需研发新型生物除草剂。【目的】从菌核青霉(Penicillium sclerotiorum)HY5中挖掘DMOA类混源萜,评价其除草活性,初步阐明其作用机制,为开发新型天然产物除草剂提供先导分子。【方法】运用正/反相硅胶柱层析、薄层层析、Sephadex LH-20凝胶柱层析和半制备高效液相色谱(HPLC)等方法分离DMOA类混源萜,采用核磁(NMR)、质谱(MS)等方法对化合物进行结构鉴定;运用种子萌发抑制法测定化合物对牛筋草(Eleusine indica)、狗尾草(Setaria viridis)、反枝苋(Amaranthus retroflexus)和三叶草(Trifolium repens)的除草活性;采用非线性回归分析方法,计算活性化合物的EC50;采用转录组-代谢组联用的方法初步分析活性化合物的除草作用机制。【结果】从HY5发酵提取物中获得了9个DMOA类混源萜,分别为berkeleydione(1)、preaustinoid A3(2)、miniolutelide B(3)、22-epoxyberkeleydione(4)、22-deoxyminiolutelide B(5)、miniolutelide C(6)、berkeleyacteal(7)、preaustinoid A2(8)和berkeleyacetal A(9)。化合物4对双子叶杂草三叶草表现出明显的促生效果,对胚根和胚芽生长的促进率分别达到30.5%和55.1%。化合物3456对单子叶杂草狗尾草和牛筋草种子具有显著的萌发抑制作用,其中化合物6的除草活性最强,抑制牛筋草胚根和胚芽伸长的EC50分别达到19.1和17.9 μg·mL-1,强于对照药剂草甘膦(30.9和66.2 μg·mL-1)。同时发现,化合物对胚根伸长的抑制效果优于对胚芽效果。进一步研究表明,化合物6通过双重调控机制抑制杂草种子萌发:一方面,降解茉莉酸信号通路中的JAZ蛋白,从而促进脱落酸合成;另一方面,干扰色氨酸代谢途径,导致血清素的异常积累,最终抑制杂草的生长。【结论】DMOA类混源萜结构新颖,对单子叶杂草具有明显的除草活性,有望开发成为新型天然产物除草剂。

关键词: 菌核青霉, DMOA类混源萜, 结构鉴定, 除草活性, 作用机制, 茉莉酸信号通路, 色氨酸代谢途径

Abstract:

【Background】3,5-Dimethylorsellinic acid (DMOA)-derived meroterpenoids exhibit diverse chemical structures and broad biological activities. However, their agricultural bioactivities have rarely been reported. Chemical herbicides often lead to increased weed resistance and environmental problem, highlighting the urgent need for the development of novel bioherbicides. 【Objective】The objective of this study is to explore DMOA-derived meroterpenoids from Penicillium sclerotiorum HY5, evaluate their herbicidal activity, and preliminarily elucidate their modes of action, thus to provide lead molecules for the development of novel natural-product herbicides. 【Method】DMOA-derived meroterpenoids were isolated using normal/ reversed-phase silica gel column chromatography (CC), thin-layer chromatography, Sephadex LH-20 gel CC, and semi- preparative high-performance liquid chromatography (HPLC). The structures of the compounds were identified via nuclear magnetic resonance (NMR) and mass spectrometry (MS). The herbicidal activity of the compounds was assessed using a seed germination inhibition assay against Eleusine indica, Setaria viridis, Amaranthus retroflexus, and Trifolium repens. The EC50 values for the bioactive compounds were determined by nonlinear regression analysis of dose-response curves. The herbicidal mechanism of the bioactive compounds was analyzed using a combined transcriptomic-metabolomic approach. 【Result】Nine DMOA-derived meroterpenoids were obtained from the HY5 fermentation extract, namely berkeleydione (1), preaustinoid A3 (2), miniolutelide B (3), 22-epoxyberkeleydione (4), 22-deoxyminiolutelide B (5), miniolutelide C (6), berkeleyacteal (7), preaustinoid A2 (8), and berkeleyacetal A (9). Compound 4 showed a significant promoting effect on the growth of the dicotyledonous weed T. repens, with the promotion rates of radicle and germ growth reaching 30.5% and 55.1%, respectively. Compounds 3, 4, 5, and 6 exhibited significant inhibitory effects on the germination of monocot weed seeds (S. viridis and E. indica). Notably, compound 6 showed the strongest herbicidal activity, with EC50 values of 19.1 and 17.9 μg·mL-1 for radicle and germ elongation of E. indica respectively, even stronger than the positive control glyphosate (30.9 and 66.2 μg·mL-1). Additionally, the compounds demonstrated more potent herbicidal activity against radicle elongation compared to germ. Further studies revealed that compound 6 inhibits weed germination through dual regulatory mechanisms: (1) degrading JAZ proteins in the jasmonic acid signaling pathway, thereby promoting abscisic acid synthesis, and (2) disrupting the tryptophan metabolism pathway, leading to abnormal serotonin accumulation and ultimately suppressing weed growth. 【Conclusion】DMOA-derived meroterpenoids possess novel structures and exhibit significant inhibitory effects on monocot weeds, showing promise for development as new natural-product herbicides.

Key words: Penicillium sclerotiorum, DMOA-derived meroterpenoids, structural identification, herbicidal activity, modes of action, jasmonic acid signaling pathway, tryptophan metabolism pathway