广豆根内生真菌Xylaria sp. GDGJ-368代谢产物研究

doi:10.16088/j.issn.1001-6600.2020.05.009

Abstract

Abstract: In order to provide experimental basis for further research on endophytic fungi from Sophora tonkinensis, the chemical compounds of the metabolites of GDGJ-368 had been studied. Seven compounds had been isolated from the metabolites through column chromatography, and their structures were elucidated by NMR spectroscopy. The results showed that the structures of the compounds were 5-carboxylmellein (1), diaporthein B (2), piliformic (3), cytochalasin C (4), cytochalasin D (5), (22E)-ergosta-6, 22-diene-3β, 5β, 8α-triol (6) and (22E, 24R) -5α, 8α-epidioxy-24-methyl-cholesta-6, 22-diene-3β-ol (7). Compound 2 was isolated from Xylaria sp. for the first time, and compounds 4 and 5 were isolated from the fungi which were isolated from the plants of the genus Sophora firstly.

Key words: Sophora tonkinensis, endophytic fungi, Xylaria sp., GDGJ-368, metabolite

CLC Number:

O629.9

QIN Yuyue, LIU Xiaobo, XU Zhaolong, MO Tuxiang, LI Jun, YANG Ruiyun. Secondary Metabolites of Endophytic Fungus Xylaria sp. GDGJ-368 from Sophora tonkinensis[J].Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(5): 71-77.

References

[1] KONIG G M, WRIGHT A D, AUST H J, et al. Geniculol, a new biologically active diterpene from the endophytic fungus Geniculosporium sp.1[J] Journal of Natural Products, 1999, 62(1): 155-157. DOI:10.1021/np9802670.
[2] STROBEL G, DAISY B. Bioprospecting for microbial endophytes and their natural products[J] Microbiology and Molecular Biology Reviews, 2003, 67(4): 491-502. DOI:10.1128/MMBR.67.4.491-502.2003.
[3] OUYANG J K, MAO Z L, GUO H, et al. Mollicellins O-R, four new depsidones isolated from the endophytic fungus Chaetomium sp. Eef-10[J]. Molecules, 2018, 23(12): 3218. DOI:10.3390/molecules23123218.
[4] SHAO C L, WU H X, WANG C Y, et al. Potent antifouling resorcylic acid lactones from the gorgonian-derived fungus Cochliobolus lunatus[J]. Journal of Natural Products, 2011, 74(4): 629-633. DOI:10.1021/np100641b.
[5] HOU X M, LIANG T M, GUO Z Y, et al. Discovery, absolute assignments, and total synthesis of asperversiamides A-C and their potent activity against Mycobacterium marinum[J]. Chemical Communications, 2019, 55: 1104-1107. DOI:10.1039/C8CC09347D.
[6] HOU X M, LI Y Y, SHI Y W, et al. Integrating molecular networking and ¹H NMR to target the isolation of chrysogeamides from a library of marine-derived Penicillium fungi[J]. Journal of Organic Chemistry, 2019, 84(3): 1228-1237.
[7] 高聪, 罗俊, 刘霞, 等. 炭角菌属真菌化学成分与生物活性研究进展[J]. 菌物学报, 2016, 35(7): 767-781.DOI:10.13346/j.mycosystema.150061.
[8] ZHENG N, YAO F H, LIANG X F, et al. A new phthalide from the endophytic fungus Xylaria sp. GDG-102[J]. Natural Product Research, 2017, 32(7): 755-760.
[9] 毛俐, 刘丽敏, 刘延成, 等. 苦参碱 Fe(Ⅲ)化合物的合成和抗肿瘤活性[J] 广西师范大学学报(自然科学版), 2008, 26(2): 60-63. DOI:10.16088/j.issn.1001-6600.2008.02.019.
[10] AHN J M, KIM Y M, CHAE H S, et al. Prenylated flavonoids from the roots and rhizomes of Sophora tonkinensis and their effects on the expression of inflammatory mediators and proprotein convertase subtilisin/kexin type 9[J]. Journal of Natural Products, 2019, 82(2): 309-317. DOI:10.1021/acs.jnatprod.8b00748.
[11] PAN Q M, LI Y H, HUA J, et al. Antiviral matrine-type alkaloids from the rhizomes of Sophora tonkinensis[J].Journal of Natural Products, 2015, 78(7): 1683-1688. DOI:10.1021/acs.jnatprod.5600325.
[12] XU W F, HOU X M, YAO F H, et al. Xylapeptide A, an antibacterial cyclopentapeptide with an uncommon L-pipecolinic acid moiety from the associated fungus Xylaria sp. (GDG-102)[J]. Scientific Reports, 2017, 7(1): 6937. DOI:10.1038/s41598-017-07331-4.
[13] QIN Y Y, LIU X B, LIN J, et al. Two new phthalide derivatives from the endophytic fungus Penicillium vulpinum isolated from Sophora tonkinensis[J]. Natural Product Research, 2019, DOI:10.1080/14786419.2019.1636237.
[14] LIANG Y, XU W F, LIU C M, et al. Eremophilane sesquiterpenes from the endophytic fungus Xylaria sp. GDG-102[J]. Natural Product Research, 2019, 33(9): 1304-1309. DOI:10.1080/14786419.2018.1472597.
[15] 徐伟锋, 姚飞华, 梁学锋, 等. 广豆根内生真菌GDG-180代谢产物研究[J]. 广西师范大学学报(自然科学版), 2017, 35(1): 58-61. DOI:10.16088/j.issn.1001-6600.2017.01.010.
[16] CHEN G Y, LIN Y C, VRIJMOED L L P, et al. A new isochroman from the marine endophytic fungus 1893#[J]. Chemistry of Natural Compounds, 2006, 42(2): 138-141. DOI:10.1007/s10600-006-0062-1.
[17] PONGCHAROEN W, RUKACHAISIRIKUL V, PHONGPAICHIT S, et al. Pimarane diterpene and cytochalasin derivatives from the endophytic fungus Eutypella scoparia PSU-D44[J]. Journal of Natural Products, 2006, 69(5): 856-858. DOI:10.1012/np0600649.
[18] 杨建香,邱声祥,佘志刚,等. 南海红树林内生真菌 Gx-5 代谢产物研究[J]. 化工技术与开发, 2013, 42(3): 1-3.
[19] OKOYE F, NWORU C, DEBBAB A, et al. Two new cytochalasins from an endophytic fungus, KL-1.1 isolated from Psidium guajava leaves[J]. Phytochemistry Letters, 2015, 14: 51-55. DOI:10.1016/j.phytol.2015.09.004.
[20] EDWARDS R L, MAITLAND D, WHALLEY A. Metabolites of the higher fungi. Part 24. Cytochalasin N, O, P, Q, and R. New cytochalasins from the fungus Hypoxylon terricola Mill[J]. Journal of the Chemical Society, Perkin Transactions 1, 1989, 1: 57-65. DOI:10.1039/p19890000057.
[21] XU H, FANG W S, CHEN X G, et al. Cytochalasin D from Hypocrella Bambusae[J]. Journal of Asian Natural Products Research, 2001, 3(2): 151-155. DOI:10.1088/10286020108041383.
[22] SONG L, WANG X F, WU Y, et al. Chemical constituents from the linseed meal[J]. Fitoterapia, 2014, 97: 15-22. DOI:10.1016/j.fitote.2014.05.008.
[23] 刘桃芳,汤华,李玲,等. 中国南海紫柳珊瑚中过氧化甾醇类化学成分的研究[J]. 第二军医大学学报, 2011, 32(5): 469-472.
[24] ALBRATTY M, EL-SHARKAWY K, ALAM S. Synthesis and antitumor activity of some novel thiophene,pyrimidine,coumarin,pyrazole and pyridine derivatives[J]. Acta Pharmacologica, 2017, 67(1): 15-33.
[25] VESELINOVIĆ J B, MATEJIĆ J S, VESELINOVIĆ A M, et al. Coumarin structure as a lead scaffold for antibacterial agents-molecular docking study[J]. Biologica Nyssana, 2016, 7(2): 167-170.
[26] KAMAUCHI H, NOJI M, KINOSHITA K, et al. Coumarins with an unprecedented tetracyclic skeleton and coumarin dimers from chemically engineered extracts of a marine-derived fungus[J]. Tetrahedron, 2018, 74(23): 2846-2856.
[27] JORGE E G, RAYAR A R, BARIGYE S B, et al. Development of an in silico model of DPPH·free radical scavenging capacity: prediction of antioxidant activity of coumarin type compounds[J]. International Journal of Molecular Sciences, 2016, 17(6): 881.
[28] YAN B C, WANG W G, HU D B, et al. Phomopchalasins A and B, two cytochalasans with polycyclic-fused skeletons from the endophytic fungus Phomopsis sp. shj2[J]. Organic Letters, 2016, 18(5): 1108-1111.
[29] PANG X, ZHAO J Y, FANG X M, et al. Metabolites from the plant endophytic fungus Aspergillus sp. CPCC 400735 and their anti-HIV activities[J]. Journal of Natural Products, 2017, 80(10): 2595-2601.
[30] KIMA E L, LI J L, DANG H T, et al. Cytotoxic cytochalasins from the endozoic fungus Phoma sp. of the giant jellyfish Nemopilema nomurai[J]. Bioorganic and Medicinal Chemistry Letters, 2012, 22(9): 3126-3129.

Metrics

Viewed

Full text

Abstract

Cited

Shared

Discussed

Comments

Recommended 10

[1]	PANG Lin-na, QIU Yan-yan, LU Jia-kuan. On Some Sufficent Conditions of p-Nilpotency of Finite Groups[J]. Journal of Guangxi Normal University(Natural Science Edition), 2014, 32(2): 64 -66 .
[2]	XU Lunhui, CHEN Kaixun. Prediction of Road Network Speed Distribution Based on BP Neural Network Optimization by Improved Firefly Algorithm[J]. Journal of Guangxi Normal University(Natural Science Edition), 2019, 37(2): 1 -8 .
[3]	LI Zhaomei, LI Wenlin, MENG Anxin, ZHAO Zhenchi, QIN Yongfu, LAN Haihui, LU Huijin, CHEN Lisha, LIANG Weigang, SHEN Hongtao. Study of ¹⁴C-AMS in Dating of the Ancient Painting[J]. Journal of Guangxi Normal University(Natural Science Edition), 2019, 37(2): 38 -43 .
[4]	XU Tingting, YU Qiuping, QI Peiyi, LIU Kehui, LI Yi, JIANG Yongrong, YU Fangming. Effects of Different Washing Solutions on the Desorption of Heavy Metals from a Lead-zinc Mine Soil[J]. Journal of Guangxi Normal University(Natural Science Edition), 2019, 37(2): 188 -193 .
[5]	HAN Bowen. Demand Responsive Transit Scheduling Method Considering Real-time Demand[J]. Journal of Guangxi Normal University(Natural Science Edition), 2019, 37(3): 9 -20 .
[6]	WU Juan, ZHU Hongyang, MEI Ping, CHEN Wu, LI Zhongbao. Polymethyl Methacrylate Modified Nano-Silica and Its Stabilizing Effect on Pickering Emulsion[J]. Journal of Guangxi Normal University(Natural Science Edition), 2019, 37(3): 120 -131 .
[7]	DU Xuesong,LIN Yong,LIANG Guokun,HUANG Yin,BIN Shiyu, CHEN Zhong,QIN Junqi,ZHAO Yi. Comparison of Low Temperature Resistant Performance between Two Tilapia[J]. Journal of Guangxi Normal University(Natural Science Edition), 2019, 37(3): 174 -179 .
[8]	LI Feiyu, WENG Xiaoxiong, YAO Shushen. Research on the Scaling Law Based on the Travel Time Interval of Passengers’ Group[J]. Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(1): 1 -9 .
[9]	XIANG Qinqin, LIAO Zhixian, LI Tinghui, JIANG Pinqun, HUANG Guoxian. Research on Modeling and Control of Photovoltaic Microgrid Inverter under Random Disturbance of Power Grid[J]. Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(1): 19 -25 .
[10]	ZHAO Xin , SONG Yingqiang, HU Yueming, LIU Yilun, ZHU Axing. Optimizing Spatial Distribution of Residential Areas by Using Multi-Source Open Data[J]. Journal of Guangxi Normal University(Natural Science Edition), 2020, 38(1): 26 -40 .

Secondary Metabolites of Endophytic Fungus Xylaria sp. GDGJ-368 from Sophora tonkinensis

PDF (PC)

Abstract

Cite this article

share this article

References

Related Articles 2

Metrics

Comments

Recommended 10

[1]	XU Weifeng,YAO Feihua, LIANG Xuefeng, ZHENG Na, YANG Ruiyun,LI Jun. Secondary Metabolites of Endophytic Fungus GDG-180 from Sophora tonkinensis [J]. Journal of Guangxi Normal University(Natural Science Edition), 2017, 35(1): 58-61.
[2]	ZHOU De-xiong, WANG Xin-zhu, XU Wei-feng, YANG Rui-yun, SHAO Chang-lun, LI Jun. Metabolites of Endophytic Fungus Ta31-2 from Soft Coral Sinularia sp. (Ⅱ) [J]. Journal of Guangxi Normal University(Natural Science Edition), 2014, 32(4): 91-95.