[1]杨道茂,王奇志,裴真巧.5株植物内生真菌生物转化柠檬烯和月桂烯产物分析[J].华侨大学学报(自然科学版),2023,44(3):374-380.[doi:10.11830/ISSN.1000-5013.202212034]
 YANG Daomao,WANG Qizhi,PEI Zhenqiao.Analysis of Biotransformation Products of Limonene and Myrcene by Five Plant Endophytic Fungi[J].Journal of Huaqiao University(Natural Science),2023,44(3):374-380.[doi:10.11830/ISSN.1000-5013.202212034]
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5株植物内生真菌生物转化柠檬烯和月桂烯产物分析()
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《华侨大学学报(自然科学版)》[ISSN:1000-5013/CN:35-1079/N]

卷:
第44卷
期数:
2023年第3期
页码:
374-380
栏目:
出版日期:
2023-05-12

文章信息/Info

Title:
Analysis of Biotransformation Products of Limonene and Myrcene by Five Plant Endophytic Fungi
文章编号:
1000-5013(2023)03-0374-07
作者:
杨道茂 王奇志 裴真巧
华侨大学 化工学院, 福建 厦门 361021
Author(s):
YANG Daomao WANG Qizhi PEI Zhenqiao
College of Chemical Engineering, Huaqiao University, Xiamen 361021, China
关键词:
生物转化 内生真菌 柠檬烯 月桂烯 柠檬烯-12-二醇
Keywords:
biotransformation endophytic fungi limonene myrcene limonene-12-diol
分类号:
Q53
DOI:
10.11830/ISSN.1000-5013.202212034
文献标志码:
A
摘要:
为了筛选具有转化利用单萜类化合物能力的微生物菌株,以5株植物内生真菌为生物催化剂,(+)-柠檬烯、(-)-柠檬烯、月桂烯为生物转化底物,结合气相色谱-质谱联用技术考察生物转化产物.结果表明:5株植物内生真菌具有生物转化(+)-柠檬烯、(-)-柠檬烯、月桂烯的能力;当底物为(+)-柠檬烯时,主要产物均为柠檬烯-1,2-二醇,其中,菌株Diaporthe Nitschke PS10的产量最高,达到4.57 g·L-1;当底物为(-)-柠檬烯时,主要产物为柠檬烯-1,2-二醇,产量为0.81~2.04 g·L-1;当底物为月桂烯时,转化产物有环氧罗勒烯、氧化芳樟醇、柠檬烯-1,2-二醇等化合物;植物内生真菌是一种很有发展潜力的生物催化剂.
Abstract:
In order to screen microbial strains with the ability to transform and utilize monoterpene compounds, five plant endophytic fungi were used as biocatalysts,(+)-limonene,(-)-limonene and myrcene were used as biotransformation substrates, and the biotransformation products were investigated by Gas Chromatography-Mass Spectrometry. The results show that five plant endophytic fungi possess the ability to biotransform(+)-limonene,(-)-limonene and myrcene. When the substrate is(+)-limonene, the main product is limonene-1,2-diol, and the highest yield is 4.57 g·L-1 when the strain is Diaporthe Nitschke PS10. When the substrate is(-)-limonene, the main product is also limonene-1,2-diol, and the yield is 0.81 to 2.04 g·L-1. When the substrate is myrcene, the conversion products include myroxyde, linalool oxide, limonene-1,2-diol and other compounds. It is indicated that plant endophytic fungi are potential biocatalysts.

参考文献/References:

[1] 徐任生,叶阳,赵维民.天然产物化学[M].2版.北京:科学出版社,2004.
[2] DUETZ W A,BOUWMEESTER H,VAN BEILEN J B,et al.Biotransformation of limonene by bacteria, fungi, yeasts, and plants[J].Applied Microbiology and Biotechnology,2003,61:269-277.DOI:10.1007/s00253-003-1221-y.
[3] VESPERMANN K A C,PAULINO B N,BARCELOS M C S,et al.Biotransformation of α-and β-pinene into flavor compounds[J].Applied Microbiology and Biotechnology,2017,101(5):1805-1817.DOI:10.1007/s00253-016-8066-7.
[4] DE CARVALHO C C,DA FONSECA M M.Biotransformation of terpenes[J].Biotechnology Advance,2006,24(2):134-142.DOI:10.1016/j.biotechadv.2005.08.004.
[5] MIRATA M A,HEERD D,SCHRADER J.Integrated bioprocess for the oxidation of limonene to perillic acid with Pseudomonas putida DSM 12264[J].Process Biochemistry,2009,44(7):764-771.DOI:10.1016/j.procbio.2009.03.013.
[6] SPEELMANS G,BIJLSMA A,EGGINK G.Limonene bioconversion to high concentrations of a single and stable product, perillic acid, by a solvent-resistant Pseudomonas putida strain[J].Applied Microbiology and Biotechnology,1998,50(5):538-544.DOI:10.1007/s002530051331.
[7] ALLOUCHE N,DAMAK A,ELLOUZ R,et al.Use of whole cells of Pseudomonas aeruginosa for synthesis of the antioxidant hydroxytyrosol via conversion of tyrosol[J].Applied and Environmental Microbiology,2004,70(4):2105-2109.DOI:10.1128/AEM.70.4.2105-2109.2004.
[8] BOUALLAGUI Z,SAYADI S.Production of high hydroxytyrosol yields via tyrosol conversion by Pseudomonas aeruginosa immobilized resting cells[J].Journal of Agricultural and Food Chemistry,2006,54(26):9906-9911.DOI:10.1021/jf062145g.
[9] ESMAEILI A,HASHEMI E.Biotransformation of myrcene by Pseudomonas aeruginosa[J].Chemistry Central Journal,2011,5:26-32.DOI:10.1186/1752-153X-5-26.
[10] FONTANILLE P,LE FLECHE A,LARROCHE C.Pseudomonas rhodesiae PF1: A new and efficient biocatalyst for production of isonovalal from α-pinene oxide[J].Biocatalysis and Biotransformation,2002,20(6):413-421.DOI:10.1080/1024242021000058702.
[11] MOLINA G,PIMENTEL M R,PASTORE G M.Pseudomonas: A promising biocatalyst for the bioconversion of terpenes[J].Applied Microbiology and Biotechnology,2013,97(5):1851-1864.DOI:10.1007/s00253-013-4701-8.
[12] PARSHIKOV I A,SUTHERLAND J B.The use of Aspergillus niger cultures for biotransformation of terpenoids[J].Process Biochemistry,2014,49(12):2086-2100.DOI:10.1016/j.procbio.2014.09.005.
[13] ROTTAVA I,TONIAZZO G,CORTINA P F,et al.Screening of microorganisms for bioconversion of(-)β-pinene and R-(+)-limonene to α-terpineol[J].Lwt-Food Science and Technology,2010,43(7):1128-1131.DOI:10.1016/j.lwt.2010.03.001.
[14] BICAS J L,DE QUADROS C P,NERI-NUMA I A,et al.Integrated process for co-production of alkaline lipase and R-(+)-α-terpineol by Fusarium oxysporum[J].Food Chemistry,2010,120(2):452-456.DOI:10.1016/j.foodchem.2009.10.037.
[15] MOLINA G,BUTION M L,BICAS J L,et al.Comparative study of the bioconversion process using R-(+)- and S-(-)-limonene as substrates for Fusarium oxysporum 152B[J].Food Chemistry,2015,174:606-613.DOI:10.1016/j.foodchem.2014.11.059.
[16] ADAMS A,DEMYTTENAERE J C R,DE KIMPE N.Biotransformation of(R)-(+)- and(S)-(-)-limonene to α-terpineol by Penicillium digitatum-investigation of the culture conditions[J].Food Chemistry,2002,80(4):525-534.DOI:10.1016/S0308-8146(02)00322-9.
[17] BADEE A Z M,HELMY S A,MORSY N F S.Utilisation of orange peel in the production of α-terpineol by Penicillium digitatum(NRRL 1202)[J].Food Chemistry,2011,126(3):849-854.DOI:10.1016/j.foodchem.2010.11.046.
[18] PESCHECK M,MIRATA M A,BRAUER B,et al.Improved monoterpene biotransformation with Penicillium sp. by use of a closed gas loop bioreactor[J].Journal of Industrial Microbiology and Biotechnology,2009,36(6):827-836.DOI:10.1007/s10295-009-0558-3.
[19] VAN RENSBURG E,MOLELEKI N,VAN DER WALT J P,et al.Biotransformation of(+)limonene and(-)piperitone by yeasts and yeast-like fungi[J].Biotechnology Letters,1997,19(8):779-782.DOI:10.1023/A:10183 44411069.
[20] FERRARA M A,ALMEIDA D S,SIANI A C,et al.Bioconversion of R-(+)-limonene to perillic acid by the yeast Yarrowia lipolytica[J].Brazilian Journal of Microbiology,2013,44(4):1075-1080.DOI:10.1590/S1517-838220 14005000008.
[21] RODRIGUEZ P,GONZALEZ D,GIORDANO S R.Endophytic microorganisms: A source of potentially useful biocatalysts[J].Journal of Molecular Catalysis B: Enzymatic,2016,133:S569-S581.DOI:10.1016/j.molcatb.2017.02.013.
[22] DE JESUS H C R,JELLER A H,DEBONSI H,et al.Multiple monohydroxylation products from rac-camphor by marine fungus Botryosphaeria sp. isolated from marine alga Bostrychia radicans[J].Journal of the Brazilian Chemical Society,2017,28(3):498-504.DOI:10.21577/0103-5053.20160262.
[23] BORGES K B,BORGES W,PUPO M,et al.Endophytic fungi as models for the stereoselective biotransformation of thioridazine[J].Applied Microbiology and Biotechnology,2007,77(3):669-674.DOI:10.1007/s00253-007-1171-x.
[24] BIER M C J,MEDEIROS A B P,SOCCOL C.Biotransformation of limonene by an endophytic fungus using synthetic and orange residue-based media[J].Fungal Biology,2017,121(2):137-144.DOI:10.1016/j.funbio.2016.11.003.
[25] DEMYTTENAERE J C R,WILLEMEN H M.Biotransformation of linalool to furanoid and pyranoid linalool oxides by Aspergillus niger[J].Phytochemistry,1998,47(6):1029-1036.DOI:10.1016/s0031-9422(98)80066-6.
[26] JùNIOR M R M,PASTORE G M.Biotransformation of limonene: A review of the main metabolic pathways[J].Quimica Nova,2007,30(2):382-387.DOI:10.1590/S0100-40422007000200027.
[27] CHIDAMBARA MURTHY K N,JAYAPRAKASHA G K,MANTUR S M,et al.Citrus monoterpenes: Potential source of phytochemicals for cancer prevention[J].ACS Symposium Series,2012,1039:545-558.DOI:10.1021/bk-2012-1093.ch031.
[28] ALEXANDRINO T D,DE MEDEIROS T D M,RUIZ A L T G,et al.Structural properties and evaluation of the antiproliferative activity of limonene-1,2-diol obtained by the fungal biotransformation of R-(+)- and S-(-)-limonene[J].Chirality,2022,34(6):887-893.DOI:10.1002/chir.23439.
[29] LAPPAS C M,LAPPASN T.D-Limonene modulates T lymphocyte activity and viability[J].Cellular Immunology,2012,279(1):30-41.DOI:10.1016/j.cellimm.2012.09.002.
[30] LEUNG A E,BLAIR M,FORSYTH C M,et al.Synthesis of the proposed structures of Prevezol C[J].Organic Letters,2013,15(9):2198-2201.DOI:10.1021/ol400754e.
[31] MORIKAWA H,YAMAGUCHI J I,SUGIMURA S I,et al.Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates[J].Beilstein Journal of Organic Chemistry,2019,15:130-136.DOI:10.3762/bjoc.15.13.

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备注/Memo

备注/Memo:
收稿日期: 2022-12-28
通信作者: 杨道茂(1975-),男,讲师,博士,主要从事微生物生物转化的研究.E-mail:ydmao@hqu.edu.cn.
基金项目: 国家级大学生科创项目(202110385039); 福建省农业重点自然科学基金资助项目(2014N0026); 福建省泉州市校(院)地协同创新专项(重点)项目(2014Z101); 福建省个人和团队科技员项目(2022年度); 中医药公共卫生服务补助专项(财社[2018]43
更新日期/Last Update: 2023-05-20