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[1]曹钰镁,金梦莹,谭璐,等.川芎内生菌Fusarium tricinctum的化学成分[J].应用与环境生物学报,2020,26(02):294-298.[doi:10.19675/j.cnki.1006-687x.2019.06005]
 CAO Yumei,JIN Mengying,TAN Lu,et al.Chemical constituents of the endophytic fungus Fusarium tricinctum from Ligusticum chuanxiong Hort.[J].Chinese Journal of Applied & Environmental Biology,2020,26(02):294-298.[doi:10.19675/j.cnki.1006-687x.2019.06005]
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川芎内生菌Fusarium tricinctum的化学成分()
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《应用与环境生物学报》[ISSN:1006-687X/CN:51-1482/Q]

卷:
26卷
期数:
2020年02期
页码:
294-298
栏目:
研究论文
出版日期:
2020-04-25

文章信息/Info

Title:
Chemical constituents of the endophytic fungus Fusarium tricinctum from Ligusticum chuanxiong Hort.
作者:
曹钰镁金梦莹谭璐罗禹胡靖文赵佳佳郭大乐邓赟
1成都中医药大学药学院中药材标准化教育部重点实验室,四川省中药资源系统研究与开发利用重点实验-省部共建国家重点实验室培育基地 成都 611137 2西南医科大学药学院 泸州 646000
Author(s):
CAO Yumei1 JIN Mengying1 TAN Lu1 LUO Yu2 HU Jingwen1 ZHAO Jiajia1 GUO Dale1? & DENG Yun1?
1 Key Laboratory of Standardization of Chinese Herbal Medicine, Ministry of Education, Sichuan Provincial Key Laboratory of Systematic Research, Development and Utilization of Chinese Medical Resources: Ministry of State Key Laboratory Breeding Base, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China 2 School of Pharmacy, Southwest Medical University, Luzhou 646000, China
关键词:
川芎内生菌Fusarium tricinctum结构鉴定细胞毒活性
Keywords:
Ligusticum chuanxiong Hort. endophytic fungus Fusarium tricinctum structure identification cytotoxicity
DOI:
10.19675/j.cnki.1006-687x.2019.06005
摘要:
采用糙米培养基对川芎内生菌Fusarium tricinctum菌种进行扩大培养,利用萃取、柱色谱、制备色谱等手段对其化学成分进行分离纯化,并通过NMR、ESI-MS等波谱手段对所得化合物进行结构鉴定;采用MTT法对部分化合物进行细胞毒活性测定. 共分离得到13个化合物,分别鉴定为苯乙酸(1),3,6-二异丙基-1-甲基哌嗪-2,5-二酮(2),fusarpyrone A(3),fusagerin B(4),N-苯乙基乙酰胺(5),fungerin(6),callyspongidipeptide A(7),环-(S-脯氨酸-R-亮氨酸)(8),vomifolilol(9),环-(4-S-羟基-R-脯氨酸-R-异亮氨酸)(10),N-acetyl-β-oxotryptamine(11),烟酸(12),邻羟基苯乙酸(13). 化合物6对OCI-LY10、HT29、MV4-11、Hela、SKOV3具有一定的抑制作用,IC50值分别为23.98 ± 2.37、93.63 ± 1.42、90.64 ± 1.65、77.65 ± 1.35、52.52 ± 2.04 μmol/L. 上述结果可为该菌种的肿瘤细胞毒活性开发提供一定的研究依据. (表1 参28)
Abstract:
To investigate the compounds produced by the endophytic fungus Fusarium tricinctum from Ligusticum chuanxiong Hort. and their cytotoxicity against three tumor cell lines, F. tricinctum was cultured with brown rice and its secondary metabolites were purified by chromatographic procedures and identified based on NMR, ESI-MS, and other spectral evidence. The MTT method was applied to test the cytotoxicity of the isolated compounds. A total of 13 compounds were isolated and identified as phenylacetic acid (1), 3,6-diisopropyl-1-methylpiperazine-2,5-dione (2), fusarpyrone A (3), fusagerin B (4), N-phenethylacetamide (5), fungerin (6), callyspongidipeptide A (7), cyclo-((S)-Pro-(R)-Leu) (8), vomifolilol (9), cyclo-(4-S-hydroxy-R-proline-R-isoleucine) (10), N-acetyl-β-oxotryptamine (11), nicotinic acid (12), and 2-hydroxybenzeneacetic acid (13). Fungerin showed weak inhibitory activity against OCI-LY10, HT29, MV4-11, Hela, and SKOV3 cells, with IC50 values of 23.98 ± 2.37, 93.63 ± 1.42, 90.64 ± 1.65, 77.65 ± 1.35, and 52.52 ± 2.04 μmol/L, respectively.

参考文献/References:

1 国家药典委员会, 中华人民共和国药典: 1部[M]. 北京: 中国医药科技出版社, 2015: 40 [Chinese pharmacopoeia commission, pharmacopoeia of People’s Republic of China: Part 1 [M]. Beijing: China Medical Science and Technology Press, 2015: 40]
2 王海. 川芎内生菌对品质影响的初步研究[D]. 成都: 成都中医药大学, 2012 [Wang H. The study on the effect of the endophytes to the quality of Ligusticum chuanxiong Hort. (Umbellales) [D]. Chengdu: Chengdu University of Traditional Chinese Medicine, 2012]
3 马川, 蒙春旺, 彭成, 熊亮, 周勤梅. 川芎内生菌Cladosporium sp.次级代谢产物及抗菌活性研究[J]. 天然产物研究与开发, 2019, 31 (1): 69-74+29 [Ma C, Meng CW, Peng C, Xiong L, Zhou QM. Isolation and identification of secondary metabolites of endophytic fungus Cladosporium sp. and study of antimicrobial activity [J]. Nat Prod Res Dev, 2019, 31 (1): 69-74+29]
4 李涛, 张智慧, 邓倩, 马洪鑫, 丁海娥. 两面针、川芎、生首乌内生真菌的分离纯化及抑菌性研究[J]. 食品安全导刊, 2015 (36): 100-102 [Li T, Zhang ZH, Deng Q, Ma HX, Ding HE. Isolation, purification and antimicrobial activity of endoohytic fungi from Zanthoμlumnitidum nitidum (Roxb.) DC, Ligusticum chuanxiong Hort., Fallopia multiflora [J]. Chin Food Saf Mag, 2015 (36): 100-102]
5 魏景超. 真菌鉴定手册[M]. 上海: 上海科学技术出版社, 1979: 609 [Wei JC. Handbook of fungal identification [M]. Shanghai: Shanghai Scientific & Technical Publishers, 1979: 609]
6 郭成, 李金花, 柴兆祥. 天祝高寒草地三线镰孢的分离鉴定及β-tubulin基因序列分析[J]. 应用与环境生物学报, 2011, 17 (1): 51-56 [Guo C, Li JH, Chai ZX. Isolation, identification and analysis of β-tubulin gene sequence of Fusarium tricinctum at different altitudes in Tianzhu alpine grassland [J]. Chin J Appl Environ Biol, 2011, 17 (1): 51-56]
7 Visconti A, Solfrizzo M. Visoltricin, a novel biologically active compound produced by Fusarium tricinctum [J]. Food Addit Contam, 1995, 12 (3): 515-519
8 Zhang Y, Zhao JL, Wang JH, Shan TJ, Mou Y, Zhou LG, Wang, JG. Chemical composition and antimicrobial activity of the volatile oil from Fusarium tricinctum, the endophytic fungus in Paris polyphylla var. yunnanensis [J]. Nat Prod Commun, 2011, 6 (11): 1759-1762
9 Cuomo V, Randazzo A, Meca G, Moretti A, Cascone A, Eriksson O, Novellino E, Ritieni A. Production of enniatins A, A(1), B, B-1, B-4, J(1) by Fusarium tricinctum in solid corn culture: structural analysis and effects on mitochondrial respiration [J]. Food Chem, 2013, 140 (4): 784-793
10 Bashyal BP, Gunatilaka AAL. Tricinonoic acid and tricindiol, two new irregular sesquiterpenes from an endophytic strain of Fusarium tricinctum [J]. Nat Prod Res, 2010, 24 (4): 349-356
11 Norppa H, Penttila M, Sorsa M, Hintikka El, Ilus T. Mycotoxin-t-2 of Fusarium tricinctum and chromosome changes in Chinese-hamster bone-marrow [J]. Hereditas, 1980, 93(2): 328-332
12 Hemphill CFP, Sureechatchaiyan P, Kassack MU, Orfali RS, Lin WH, Daletos G , Proksch P. OSMAC approach leads to new fusarielin metabolites from Fusarium tricinctum [J]. J Antibiot, 2017, 70 (6): 726-732
13 Nenkep V, Yun K, Zhang D, Choi HD, Kang JS, Son BW. Induced production of bromomethylchlamydosporols A and B from the marine-derived fungus Fusarium tricinctum [J]. J Nat Prod, 2010, 73 (12): 2061-2063
14 Sun WJ, Zhu HT, Zhang TY, Zhang MY, Wang D, Yang CR, Zhang CR, Zhang YX, Zhang YJ. Two new alkaloids from Fusarium tricinctum SYPF 7082, an endophyte from the root of Panax notoginseng [J]. Nat Prod Bioprosp, 2018, 8 (5): 391-396
15 Zhang JN, Liu D, Wang H, Liu TX, Xin ZH. Fusartricin, a sesquiterpenoid ether produced by an endophytic fungus Fusarium tricinctum Salicorn 19 [J]. Eur Food Res Technol, 2015, 240 (4): 805-814
16 Ola ARB, Thomy D, Lai D, Brotz-Oesterhelt H, Prolcsch P. Inducing secondary metabolite production by the endophytic fungus Fusarium tricinctum through coculture with Bacillus subtilis [J]. J Nat Prod, 2013, 76 (11): 2094-2099
17 Li XH, Han XH, Qin LL, He JL, Cao ZX, Gu YC, Guo DL, Deng Y. Isochromanes from Aspergillus fumigatus, an endophytic fungus from Cordyceps sinensis [J]. Nat Prod Res, 2019, 33 (13): 1870-1875
18 Gutierrez-Lugo MT, Woldemichael GM, Singh MP, Suarez PA, Maiese WM, Montenegro G, Timmermann BN. Isolation of three new naturally occurring compounds from the culture of Micromonospora sp. P1068 [J]. Nat Prod Res, 2005, 19 (7): 645-652
19 Guo ZY, Li XS, Zhang L, Feng ZW, Deng ZS, He HB, Zou K. Cytotoxic tremulanes and 5,6-secotremulanes, four new sesquiterpenoids from a plant-associated fungus X1-2 [J]. Nat Prod Res, 2016, 30 (22): 2582-2589
20 Trisuwan K, Rukachaisirikul V, Borwornwiriyapan K, Phongpaichit S, Sakayaroj J. Pyrone derivatives from the soil fungus Fusarium solani PSU-RSPG37 [J]. Phytochem Lett, 2013, 6 (3): 495-497
21 Wen H, Li Y, Liu XZ, Ye WC, Yao XS, Che YS. Fusagerins A–F, new alkaloids from the fungus Fusarium sp. [J]. Nat Prod Bioprosp, 2015, 5 (4): 195-203
22 王航航, 李刚, 彭晓娉, 娄红祥. 狭叶十大功劳内生真菌Colletotrichum fioriniae F18的次级代谢产物研究[J]. 药学学报, 2018, 53 (11): 1862-1867 [Wang HH, Li G, Peng XP, Lou HX. Secondary metabolites from Colletotrichum fioriniae F18, an endophytic fungus isolated from the medicinal plant Mahonia fortunei [J]. Acta Pharm, 2018, 53 (11): 1862-1867]
23 Uchida R, Imasato R, Yamaguchi Y, Masuma R, Shiomi K, Tomada H, Omura S. New insecticidal antibiotics, hydroxyfungerins A and B, produced by Metarhizium sp. FKI-1079 [J]. J Antibiot, 2010, 37 (23): 804-809
24 Yang B, Dong JD, Zhou XF, Yang XW, Lee KJ, Wang LS, Zhang S, Liu YH. Proline-containing dipeptides from a marine sponge of a Callyspongia species [J]. Helv Chin Acta, 2009, 92 (6): 1112-1117
25 Jong TT, Jean MY. Constituents of Houttuyniae cordata and the crystal structure of vomifoliol [J]. J Chin Chem Soc-Taip, 1993, 40 (4): 399-402
26 Ovenden SPB, Nielson JL, Liptrot CH, Willis RH, Tapiolas DM, Wright AD, Motti CA. A new diketopiperazine, cyclo-(4-S-hydroxy-R-proline-R-isoleucine), from an australian specimen of the sponge Stelletta sp. [J]. Mar Drugs, 2011, 9 (11): 2469-2478
27 Martinez-Luis S, Gomez JF, Spadafora C, Guzman HM, Gutierrez M. Antitrypanosomal alkaloids from the marine bacterium Bacillus pumilus [J]. Molecules, 2012, 17 (9): 11146-11155
28 马宏宇, 孙奕, 吕阿丽, 陈刚, 吴红华, 裴月湖. 茵陈蒿化学成分的分离与鉴定[J]. 中国药物化学杂志, 2010, 20 (1): 61-63+69 [Ma HY, Sun Y, Lü AL, Chen G, Wu HH, Pei YH. Isolation and identification of chemical constituents from Artemisia capillaries Thunb. [J]. J Med Chem, 2010, 20 (1): 61-63+69]

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更新日期/Last Update: 2020-04-25