一株植物内生真菌漆斑菌次级代谢产物的研究
Secondary metabolites of the endophytic fungus Myrothecium sp. from Pinellia ternata
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摘要: 从一株植物内生漆斑菌属Myrothecium sp.真菌固体发酵物的乙酸乙酯提取物中分离得到12个化合物。采用硅胶、Sephadex LH-20和制备高效液相等柱色谱技术进行分离纯化,通过理化性质研究及波谱学手段对单体化合物进行结构鉴定,分别鉴定为3''-羟基疣孢菌素A(1)、疣孢菌素A(2)、乙酰基疣孢菌素L(3)、疣孢菌素J(4)、疣孢菌素K(5)、漆斑菌素A(6)、漆斑菌素D(7)、漆斑菌素H(8)、漆斑菌素J(9)、verrol 4-acetate (10)、(3S, 3aS, 6α, 6aR)-dihydrosporothrioride (11)和4,6-二羟基-1(3H)-异苯并呋喃(12)。其中,化合物1、5、9 ~ 12为首次从漆斑菌属真菌中分离得到,化合物2、3、4、7和8对白色念珠菌有较强的抑制作用,其最低抑菌浓度MIC50分别是0.318、0.218、0.047、0.569和0.558 μg/mL。Abstract: Using a series of purification methods including silica gel, Sephadex LH-20 and preparative high performance liquid chromatography, secondary metabolites of Myrothecium sp. were purified from the ethyl acetate extract of the solid fermentation product. Based on structure characterization and investigation on the physical and chemical properties a, twelve monomeric compounds were identified as 3''-hydroxyverrucarin A (1), verrucarin A (2), verrucarin L acetate (3), verrucarin J (4), verrucarin K (5), roridin A (6), roridin D (7), roridin H (8), roridin J (9), verrol 4-acetate (10), (3S, 3aS, 6α, 6aR)-dihydrosporothrioride (11) and 4,6-dihydroxy-1(3H)-isobenzofuranone (12). Compounds 1, 5 and 9 -12 were isolated from Myrothecium sp. for the first time.Compounds 2, 3, 4, 7 and 8 exhibited strong inhibitory effects on Candida albicans, with a minimal inhibitory concentration (MIC50) of 0.318, 0.218, 0.047, 0.569 and 0.558 μg/mL, respectively.
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Keywords:
- Pinellia ternata /
- endophytic fungi /
- Myrothecium sp. /
- verrucarin /
- roridin
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[1] . Phytochemistry,2020,174:112338. [2] Wang XY,Zhang LH,Fan N,et al. Research progress on application of endophytic fungi in Chinese medicinal materials[J]. Shandong Chem Ind(山东化工),2020,49(22):62-64,67. [3] Chen YJ,Zhu LJ,Yu HM,et al. A new alkaloid from endophytic fungus Aspergillus fumigatus of Euphorbia royleana[J]. Chin Trad Herb Drugs(中草药),2019,50(22):5400-5403. [4] Rashid TS. Bioactive metabolites from tomato endophytic fungi with antibacterial activity against tomato bacterial spot disease[J]. Rhizosphere,2021,17:100292. [5] You X,Feng S,Luo SL,et al. Studies on a rhein-producing endophytic fungus isolated from Rheum palmatum L.[J]. Fitoterapia,2013,85:161-168. [6] Ren N,Liu JJ,Yang DL,et al. Indentification of vincamine indole alkaloids producing endophytic fungi isolated from Nerium indicum ,Apocynaceae[J]. Microbiol Res,2016,192:114-121. [7] Pavanasasivam G,Jarvis BB. Microbial transformation of macrocyclic trichothecenes[J]. Appl Environ Microbiol,1983,46(2):480-483. [8] Jarvis BB,Midiwo JO,Desilva T,et al. Verrucarin-L,a new macrocyclic trichothecene[J]. Antibiot,1981,34(1):120-121. [9] Iida A,Konishi K,Kubo H,et al. Trichothecinols A,B and C,potent anti-tumor promoting sesquiterpenoids from the fungus Trichothecium[J]. Tetrahedron Lett,1996,37(51):9219-9220. [10] Saikawa Y,Okamoto H,Inui T,et al. Toxic principles of a poisonous mushroom Podostroma cornu-damae[J]. Tetrahedron,2001,57(39):8277-8281. [11] Breitenstein W,Tamm C. Verrucarin K,the first natural trichothecene derivative lacking the 12,13-epoxy group[1][J]. Helv Chim Acta,1977,60(5):1522-1527. [12] Eppley RM,Mazzola EP,Highet RJ,et al. Structure of satratoxin H,a metabolite of Stachybotrys atra. Application of proton and carbon-13 nuclear magnetic resonance.[J]. J Org Chem,1977,42(2):240-243. [13] Zhang LP,Gong BY,Peng J,et al. Immunosuppressants isolated from a Phoma sp. 299Ⅱ. Studies on SIPI-299-I,299-Y,299-AD[J]. Chin J Antibiot(中国抗生素杂志),2000,25(5):18-20,43. [14] Breitenstein W,Tamm C. 13C-NMR.-spectroscopy of the trichothecane derivatives verrucarol,verrucarins A and B and roridins A,D and H[J]. Helv Chim Acta,1975,58(4):1172-1180. [15] Yu NJ,Guo SH,Lu HY. Cytotoxic macrocyclic trichothecenes from the mycelia of calcarisporium arbuscula preuss[J]. J Asian Nat Prod Res,2002,4(3):179-183. [16] Laurent D,Guella G,Roquebert M,et al. Cytotoxins,mycotoxins and drugs from a new deuteromycete,Acremonium neo-caledoniae,from the southwestern lagoon of New Caledonia[J]. Planta Med,2000,66(1):63-66. [17] Isaka M,Chinthanom P,Boonruangprapa T,et al. Eremophilane-Type Sesquiterpenes from the Fungus Xylaria sp. BCC 21097[J]. J Nat Prod,2010,73(4):683-687. [18] Xian JY,Lin XP,Wang JF,et al. Secondary metabolites from mangroves endophytic fungus Pestalotiopsis versicolor under high salinity environment[J]. Nat Prod Res Dev(天然产物研究与开发),2014,26(9):1412-1415. [19] Liu MJ,Seidel V,Katerere DR,et al. Colorimetric broth microdilution method for the antifungal screening of plant extracts against yeasts[J]. Methods,2007,42:325-329.
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