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Macrocyclic trichothecenes from myrothecium verrucaria PA 57 and their cytotoxic activity

Chinese Journal of Natural Medicines 2024年第9期22卷 854-863页

作者： MO Jisong TAN Yufen AI Wenjing LI Yunyun YUAN Yiyun JIANG Yueping XU Kangping TAN Guishan WANG Wenxuan LI Jing LIU Shao Department of Pharmacy National Clinical Research Center for Geriatric DisordersXiangya HospitalCentral South UniversityChangsha 410008China Xiangya School of Pharmaceutical Sciences Central South UniversityChangsha 410008China

Four novel macrocyclic trichothecenes,termed mytoxins D-G(1-4),along with four known analogs(5-8),were isolated from the ethyl acetate extract of fermented rice inoculated with the fungus myrothecium verrucaria *** compound features a tricyclic 12,13-epoxytrichothec-9-ene(EPT)***,mytoxin G(4)represents the first instance of a macrocyclic trichothecene incorporating a glucosyl unit within the trichothecene *** structures of the newly identified compounds were elucidated through comprehensive spectroscopic analysis combined with quantum chemical *** isolated compounds demonstrated cytotoxic activity against the CAL27 and HCT116 cell lines,which are models for human oral squamous cell carcinoma and colorectal cancer,***,mytoxin D(1)and mytoxin F(3)exhibited pronounced cytotoxic effects against both cancer cell lines,with IC_(50)values ranging from 3 to 6 nmol·L^(-1).Moreover,compounds 1 and 3 were found to induce apoptosis in HCT116 cells by activating caspase-3.

关键词： Macrocyclic trichothecenes myrothecium verrucaria Cytotoxicity Secondary metabolite Soil fungi

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Bioherbicidal Efficacy of a myrothecium verrucaria-Sector on Several Plant Species

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American Journal of Plant Sciences 2016年第16期7卷 2376-2389页

作者： Robert E. Hoagland Clyde D. Boyette Kenneth C. Stetina Robin H. Jordan United States Department of Agriculture-Agricultural Research Service (USDA-ARS) Crop Production Systems Research Unit Stoneville MS USA United States Department of Agriculture-Agricultural Research Service (USDA-ARS) Biological Control of Pests Research Unit Stoneville MS USA

Comparative studies were conducted on mycelial preparations of the bioherbicide, myrothecium verrucaria (MV) strain IMI 361690 and a recently discovered sector (MV-Sector BSH) of this fungus. The whitish sector was discovered, isolated, grown in pure culture on PDA and found to be a stable, non-spore producing mutant when cultured over several months under conditions that cause circadian sporulation during growth of its MV parent. Application of MV and MV-Sector BSH mycelial preparations to intact plants (hemp sesbania and sicklepod) and leaf discs (kudzu and glyphosate-resistant Palmer amaranth) showed that the sector efficacy was generally equal to, or slightly lower than MV. Bioassays of MV and this sector on seed germination and early growth of sicklepod and hemp sesbania seeds demonstrated that hemp sesbania seeds were slightly more sensitive to the fungus than sicklepod seeds and that the sector bioherbicidal activity was slightly less than that of MV. SDS-PAGE protein profiles of cellular extracts of MV and the sector and their respective culture supernatants showed several differences with respect to quantity and number of certain protein bands. Overall results showed that the isolate was a non-spore producing mutant with phytotoxicity to several weeds (including weeds tolerant or resistant to glyphosate), and that the phytotoxic effects were generally equivalent to those caused by MV treatment. Results of this first report of a non-sporulating MV mutant that suggest additional studies on protein analysis, and an extended weed host range under greenhouse and field conditions are needed in order to further evaluate its possible bioherbicidal potential.

关键词： Bioherbicide Glyphosate-Resistance Palmer Amaranth Kudzu Hemp Sesbania Sicklepod myrothecium verrucaria Fungal Sector

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Determination of Nematicidal Effects of Some Biopesticides against Root-Knot Nematode （Meloidogyne incognita） on Kiwifruit

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Journal of Agricultural Science and Technology(A) 2017年第8期7卷 546-551页

作者： Ilker Kepenekci Onur Dura Sami Dura Department of Plant Protection Faculty of Agriculture Gaziosmanpasa University Tashciftlik Tokat 60250 Turkey Atatiirk Central Horticultural Research Institute Merkez Yalova 77100 Turkey ROTAM Lifesciences Kimyasal Tartm Tic. Ltd. Sti Pasaport lzmir 35210 Turkey

The aim of this study was to determine the nematicidal effects of some biopesticides againist root-knot nematodes （RKNs）（Meloidogyne incognita） on Bruno type kiwifruit seedlings. Research was conducted in the Atattirk Central Horticultural Research Institute （ACHRI, Yalova, Turkey） greenhouse during 2013-2014. Biopesticides observed in this study were： sesame oil （Devalone EC）, castor oil （Ricinus communis）, myrothecium verrucaria （M. verrucaria strain AARC-0255, Inferno DF）, Glomus spp. （Endomycorrhizal fungi, Endo Roots Soluble SP） and Paecilomyces lilacinus （Entomopathogenic fungi, P. lilacinus strain PL1, Bionematon SL）. Nematicide Nemacur EC 400 （fenamiphos） was used as treated control （TC） and trials were set up as randomized parcel design （RPD） with seven characters and 10 replicates. Reproduction ratio was determined according to scale values in trial applications and second stage juvenile （J2） populations of M. incognita in soil. The results showed that the best nematicidal effects against RKNs were determined in castor oil （77.92% in 2013 and 73.61% in 2014） and P. lilacinus （61.03% in 2013 and 55.55% in 2014）.

关键词： Root-knot nematodes Meloidogyne incognita sesame oil castor oil myrothecium verrucaria Glomus Paecilomyceslilacinus kiwifruit.

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两株羌活内生菌的化学成分研究

两株羌活内生菌的化学成分研究

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作者：康敏成都中医药大学

学位级别：硕士

中药内生菌能产生大量的结构新颖,活性优异的次生代谢产物,而且有些中药内生菌能产生与宿主植物相同或相近的代谢产物。由此,中药内生菌已成为中药化学研究的热点。羌活为我国中药常用品种,具有解表散寒,祛风除湿,止痛的功效。为了寻找... 详细信息

中药内生菌能产生大量的结构新颖,活性优异的次生代谢产物,而且有些中药内生菌能产生与宿主植物相同或相近的代谢产物。由此,中药内生菌已成为中药化学研究的热点。羌活为我国中药常用品种,具有解表散寒,祛风除湿,止痛的功效。为了寻找结构新颖、活性优异的次生代谢产物,我们对羌活内生菌的化学成分进行研究。课题研究内容主要分为两部分,第一部分为一株羌活内生菌myrothecium verrucaria的正丁醇部分次生代谢产物化学成分研究,第二部分为一株羌活内生菌Aspergillus fumigatus经表观修饰后次生代谢产物的化学成分研究。从新鲜羌活Notopterygium inchum Ting ex ***的根中分离得到一株内生真菌myrothecium verrucaria。课题组前期从myrothecium verrucaria代谢产物乙酸乙酯提取物分离得到14个化合物。本文进一步对myrothecium verrucaria代谢产物的正丁醇提取物进行化学成分研究,从中分离并鉴定了14个化合物,分别为:1环(脯氨酸-苯丙氨酸)(cyclo-(Pro-Phe))、2环(4-OH-脯氨酸-苯丙氨酸)(cyclo-(4-OH-Pro-Phe))、3环(4-OH-脯氨酸-亮氨酸)(cyclo-(4-OH-Pro-Leu))、4环(脯氨酸-丙氨酸)(cyclo-(Pro-Ala))、5环(脯氨酸-亮氨酸)(cyclo-(Pro-Leu))、6环(脯氨酸-甘氨酸)(cyclo-(Pro-Gly))、7环(苯丙氨酸-甘氨酸)(cyclo-(Phe-Gly))、8环(亮氨酸-亮氨酸)(cyclo-(Leu-Leu))、化合物9 N-乙酰色胺(N-acetyl tryptamine)、10 N-苯乙基乙酰胺(N-phenylethyl-acetamide)、11 N-(2-羟基苯乙基)乙酰胺(N-(2-hydroxyphenethyl)acetamide)、12 N-(4-羟基苯乙基)乙酰胺(N-(4-hydroxyphenethyl)acetamide)、13尿嘧啶(uracil)、14胸腺嘧啶(thymine)。化合物14均为首次从myrothecium verrucaria真菌中分离得到。中药内生菌携带的能产生次生代谢产物的基因非常丰富。而在常规实验室培养条件下,许多基因处于沉默状态,或表达水平很低。为了刺激内生真菌沉默基因的表达,寻找新型的生物活性成分,我们采用在培养基中添加表观遗传修饰剂5-氮杂胞苷(5-AC)和伏立诺他(SAHA)的策略,并对乙酸乙酯提取物进行HPLC化学成分分析。最终选择了一株羌活内生菌Aspergillus fumigatus,并通过在培养基中加入SAHA的培养方式,对其代谢产物的乙酸乙酯提取物进行化学成分研究,最终分离并鉴定了8个化合物,为:1 5a,6-脱氢-3-脱羟甲基二硫代-3,10a-双(甲硫基)胶霉毒素(5a,6-dehydro-3-dehydroxymethylbisdethio-3,10a-bis(methylthio)gliotoxin)、2双硫双-(甲硫基)胶霉毒素(bis(dethio)bis-(methylthio)gliotoxin)、3胶霉毒素(gliotoxin)、4疣孢青霉原(verruculogen)、5 12,13-二羟基烟曲霉毒素C(12,13-dihydroxyfumitremorgin C)、6乙酰苯胺(acetanilide)、7 AM6898A、8 pseurotin A。其中化合物1为首次分离得到的天然产物,化合物6、7为首次从Aspergillus fumigatus中分离得到。

关键词：羌活内生菌 myrothecium verrucaria Aspergillus fumigatus 化学成分结构鉴定

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