肉桂内生真菌Xylaria sp.DYR-1-4次级代谢产物及其抗肉桂枝枯病菌活性研究  

Study on the secondary metabolites of endophytic fungi Xylaria sp.DYR-1-4 and anti-Lasiodiplodia pseudotheobromae activity against Cinnamomum cassia

作　　者：庞亚琪 吕佳 黄宏杨 廖沛然 罗碧 潘利明 PANG Yaqi;LYU Jia;HUANG Hongyang;LIAO Peiran;LUO Bi;PAN Liming(School of Chinese Materia Medica,Guangdong Pharmaceutical University,Guangzhou 510006,China;Key Laboratory of State Administration of Traditional Chinese Medicine for Production&Development of Cantonese Medicinal Materials,Guangzhou Comprehensive Experimental Station of National Industrial Technology System for Chinese Materia Medica,Guangdong Engineering Research Center of Good Agricultural Practice&Comprehensive Development for Cantonese Medicinal Materials,Guangzhou 510006,China;International Institute for Translational Chinese Medicine,Guangzhou University of Chinese Medicine,Guangzhou 510006,China)

机构地区：[1]广东药科大学中药学院,广东广州510006 [2]国家中医药管理局岭南药材生产与开发重点研究室,国家中药材产业技术体系广州综合试验站,广东省南药规范化种植与综合开发工程技术研究中心,广东广州510006 [3]广州中医药大学国际中医药转化医学研究所,广东广州510006

出　　处：《广东药科大学学报》2025年第1期54-60,共7页Journal of Guangdong Pharmaceutical University

基　　金：广东省农村科技特派员项目(KTP20210408);广州市基础研究计划基础与应用基础研究项目(202201010293)。

摘　　要：目的研究肉桂内生真菌Xylaria sp.DYR-1-4的次级代谢产物及其抗肉桂枝枯病菌的活性。方法采用现代色谱分离手段,包括反相中压层析柱色谱和半制备高效液相方法分离纯化Xylaria sp.DYR-1-4菌株的次级代谢产物;采用现代波谱技术包括紫外光谱(UV)、核磁共振光谱(NMR)、质谱(MS)等技术鉴定其结构;采用微量肉汤稀释法体外测定抗肉桂枝枯病菌的活性。结果从肉桂内生真菌Xylaria sp.DYR-1-4中分离鉴定得11个化合物,分别为Xylariaopyrone I(1)、3-(4-methoxy-2-oxo-2H-pyran-6-yl)propanoic acid(2)、nodulisporipyrones B(3)、nodulisporipyrones C(4)、nodulisporipyrones A(5)、4R,6S,9S-环(D-4-OH-L-Pro-L-Leu)(6)、环(4-OH-Pro-Phe)(7)、5-carboxymellein(8)、(2S)-butylitaconic acid(9)、邻苯二甲酸二丁酯(10)和亚油酸(11)。其中化合物4对肉桂枝枯病菌具有较强抑制作用,IC50值为(3.29±0.11)μg/mL,其他化合物表现出中等强度抑制活性(IC50<60μg/mL)。构效关系分析表明,化合物3、4和5的差别主要集中于侧链上C-8位-OH的存在与否及其相对构型,其抗枝枯病菌活性表现为化合物4>3>5,说明当侧链上C-8位存在-OH时,其抗枝枯病活性更强,且R-OH比S-OH活性更强。结论α-吡喃酮衍生物类化合物可能是炭角菌Xylaria sp.DYR-1-4的抗肉桂枝枯病菌主要特征性成分,这为进一步寻找新型环保的生物农药提供新思路。Objective To study compounds from the endophytic fungus Xylaria sp.DYR-1-4 of Cinnamomum cassia for their anti-Lasiodiplodia pseudotheobromae activity.Methods The secondary metabolites produced by Xylaria sp.DYR-1-4 were isolated and purified by modern chromatography technology,including reversed-phase medium-pressure chromatography and semi-preparative high performance liquid chromatography.The structure of the compounds was elucidated by spectrometric methods,including ultraviolet spectroscopy(UV),nuclear magnetic resonance spectroscopy(NMR),and mass spectrometry(MS).The anti-Lasiodiplodia pseudotheobromae activity was assessed by in vitro micro broth dilution assays.Results Eleven compounds were isolated from Xylaria sp.DYR-1-4,which were identified as Xylariaopyrone I(1),3-(4-methoxy-2-oxo-2H-pyran-6-yl)propanoic acid(2),nodulisporipyrones B(3),nodulisporipyrones C(4),nodulisporipyrones A(5),4R,6S,9S-cyclo(D-4-OH-L-Pro-L-Leu)(6),cyclo(4-OH-Pro-Phe)(7),5-carboxymellein(8),(2S)-butylitaconic acid(9),Dibutyl phthalate(10)and linoleic acid(11).Compound 4 exhibited strong inhibitory effects on the growth of L.pseudotheobromae with IC50 values of(3.29±0.11)μg/mL,while the other compounds demonstrated moderate inhibitory effects(IC50<60μg/mL).Structure-activity relationship analysis indicated that the distinctions among compounds 3,4,and 5 were primarily attributed to the presence or absence of an-OH group at the C-8 position of the side chain,along with their relative configurations.The observed anti-Lasiodiplodia pseudotheobromae activity followed the order 4>3>5,which suggested that the presence of an-OH group at the C-8 position enhanced activity against Lasiodiplodia pseudotheobromae with the R-configuration demonstrating superior activity compared to the S-configuration.Conclusion The findings indicate thatα-pyranone derivatives could represent the key bioactive components of Xylaria sp.DYR-1-4,contributing to its efficacy against Lasiodiplodia pseudotheobromae,which provides new ideas for further investig

关 键 词：肉桂 内生真菌 Xylaria sp. 次级代谢产物 抗肉桂枝枯病菌活性 

分 类 号：R914.4[医药卫生—药物化学]