[1]杨道茂.假臭草来源植物内生真菌生物转化(+)-柠檬烯产物分析[J].华侨大学学报(自然科学版),2023,44(4):495-501.[doi:10.11830/ISSN.1000-5013.202302003]
　YANG Daomao.Analysis of Biotransformation Products of(+)-Limonene by Plant Endophytic Fungi From Praxelis clematidea[J].Journal of Huaqiao University(Natural Science),2023,44(4):495-501.[doi:10.11830/ISSN.1000-5013.202302003]
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假臭草来源植物内生真菌生物转化(+)-柠檬烯产物分析()
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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4期
页码:
495-501
栏目:
出版日期:
2023-07-17

文章信息/Info

Title:
Analysis of Biotransformation Products of(+)-Limonene by Plant Endophytic Fungi From Praxelis clematidea
文章编号:
1000-5013(2023)04-0495-07
作者:
杨道茂
华侨大学 化工学院, 福建 厦门 361021
Author(s):
YANG Daomao
College of Chemical Engineering, Huaqiao University, Xiamen 361021, China
关键词:
(+)-柠檬烯;  假臭草;  植物内生真菌;  (1S; 2S; 4R)-柠檬烯-1; 2-二醇
Keywords:
(+)-limonene;  Praxelis clematidea;  plant endophytic fungi;  (1S; 2S; 4R)-limonene-1; 2-diol
分类号:
Q53
DOI:
10.11830/ISSN.1000-5013.202302003
文献标志码:
A
摘要:
为了筛选能够生物转化(+)-柠檬烯的微生物,将7株假臭草内生真菌作为生物催化剂,在30 ℃,150 r·min-1下发酵6 d后,添加体积分数为0.5%的(+)-柠檬烯继续转化4 d,并采用薄层层析、气相色谱-质谱联用和核磁共振技术分析产物.结果表明:各真菌生物转化(+)-柠檬烯的主要产物为(1S,2S,4R)-柠檬烯-1,2-二醇、环氧柠檬烯、(1S,2R,4R)-柠檬烯-1,2-二醇等;菌株Alternaria Nees PS08生成唯一产物(1S,2S,4R)-柠檬烯-1,2-二醇,质量浓度达到(2.46±0.16)g·L-1.
Abstract:
In order to screen microorganisms of biotransformation of(+)-limonene, seven endophytic fungi from Praxelis clematidea were used as biocatalysts. After 6 days of fermentation under 30 ℃ and 150 r · min-1, 0.5% volume fraction of(+)-limonene was added for further 4 days, the products were analyzed by Thin Layer Chromatography, Gas Chromatography-Mass Spectrometry and Nuclear Magnetic Resonance technology. The results showed that the main products of biotransformation of(+)-limonene by various fungi were(1S,2S,4R)-limonene-1,2-diol, limonene epoxide,(1S,2R,4R)-limonene-1,2-diol, etc.. The strain Alternaria Nees PS08 produced only product(1S,2S,4R)-limonene-1,2-diol, and its mass concentration reached(2.46±0.16)g·L-1.

参考文献/References:

[1] 台亚楠,董曼,任婧楠,等.柠檬烯微生物转化的研究进展[J].食品科学,2014,35(17):272-277.DOI:10.7506/spkx1002-6630-201417052.
[2] 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.
[3] 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.
[4] 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(1):606-613.DOI:10.1016/j.foodchem.2014.11.059.
[5] 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,2003,80(4):525-534.DOI:10.1016/S0308-8146(02)00322-9.
[6] DEMYTTENAERE J C R,VANOVERSCHELDE J,DE KIMPE N.Biotransformation of(R)-(+)- and(S)-(-)-citronellol by Aspergillus sp. and Penicillium sp., and the use of solid-phase microextraction for screening[J].Journal of Chromatography A,2004,1027(1/2):137-146.DOI:10.1016/j.chroma.2003.08.090.
[7] 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.
[8] FERRARA M A,ALMEIDA D S,SIANI A.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/S1517-838220140 05000008.
[9] 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.
[10] BICAS J L,FONTANILLE P,PASTORE G M,et al.A bioprocess for the production of high concentrations of R-(+)-α-terpineol from R-(+)-limonene[J].Process Biochemistry,2010,45(4):481-486.DOI:10.1016/j.procbio.2009.11.007.
[11] ROTTAVA I,CORTINA P F,GRANDO C E,et al.Isolation and screening of microorganisms for R-(+)-limonene and(-)-β-pinene biotransformation[J].Applied Biochemistry and Biotechnology,2010,162(3):719-732.DOI:10.1007/s12010-009-8872-9.
[12] RODRIGUEZ P,GONZALEZ D,GIORDANO S R.Endophytic microorganisms: A source of potentially useful biocatalysts[J].Journal of Molecular Catalysis B: Enzymatic,2016,133(1):S569-S581.DOI:10.1016/j.molcatb.2017.02.013.
[13] DE JESUS H C R,JELLER A H,DEBONSI H M,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.
[14] BIER M C,MEDEIROS A B,SOCCOL C R.Biotransformation of limonene by an endophytic fungus using synthetic and orange residue-based media[J].Fungal Biology,2017,121(2):137-144.
[15] BORGES K B,BORGES W D E S,PUPO M T,et al.Endophytic fungi as models for the stereoselective biotransformation of thioridazine[J].Applied Microbial and Cell Physiology,2007,77(3):669-674.DOI:10.1007/s00253-007-1171-x.
[16] DEMYTTENAERE J C R,WILLEMEN H M.Biotransformation of linalool to furanoid and pyranoid linalool oxides by Aspergillus niger[J].Phytochemistry,1997,47(6):1029-1036.DOI:10.1016/s0031-9422(98)80066-6.
[17] 王奇志,刘育梅,李书明,等.假臭草花精油的化学组成及对柑橘木虱的驱避和致死活性[J].昆虫知识,2018,55(1):117-125.
[18] 王伟,代光明,李书明,等.假臭草总黄酮超声波辅助提取工艺优化及抑菌活性[J].天然产物研究与开发,2017,29(8):1343-1361.
[19] 杨道茂,陈煌.近海海洋真菌生物转化(+)-柠檬烯[J].华侨大学学报(自然科学版),2020,41(1):67-71.DOI:10.11830/ISSN.1000-5013.201904020.
[20] MAROSTICA M R,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.
[21] 张璐璐,范刚,何进,等.柠檬烯微生物转化及其相关酶的研究进展[J].食品工业科技,2019,40(12):317-326.DOI:10.13386/j.issn1002-0306.2019.12.051.
[22] FONTANILLE P,GROS J B,LARROCHE C.Biotransformations with crude enzymes and whole cells[M]//Pandey A,et al.Enzyme Technology.New York:Asiatech Publishers Inc,2006.
[23] LEIT?O S G,MARTINS G R,MARTíNEZ-FRUCTUOSO L,et al.Absolute stereochemistry of antifungal limonene-1,2-diols from Lippia rubella[J].Revista Brasileira de Farmacognosia,2020,30(4):537-543.DOI:10.1007/s43450-020-00081-x.
[24] 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.
[25] SALES A,MOREIRA R C,PASTORE G M,et al.Establishment of culture conditions for biotransformation of R-(+)-limonene to limonene-1,2-diol by Colletotrichum nymphaeae CBMAI[J].Process Biochemistry,2019,78:8-14.DOI:10.1016/j.procbio.2019.01.022.
[26] áGUILA S,VAZQUEZ-DUHALT R,TINOCO R,et al.Stereoselective oxidation of R-(+)-limonene by chloroperoxidase from Caldariomyces fumago[J].Green Chemistry,2008,10(6):647-653.DOI:10.1039/B719992A.
[27] LEE T K,ROH H S,YU J S,et al.Pinecone of pinus koraiensis inducing apoptosis in human lung cancer cells by activating caspase-3 and its chemical constituents[J].Chemical Biodiversity,2016,14(4):e1600412.DOI:10.1002/cbdv.201600412.
[28] LAPPAS C M,LAPPAS N 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.
[29] 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.
[30] BLAIR M,TUCK K L.A new diastereoselective entry to the(1S,4R)- and(1S,4S)-isomers of 4-isopropyl-1-methyl-2-cyclohexen-1-ol, aggregation pheromones of the ambrosia beetle Platypus quercivorus[J].Tetrahedron: Asymmetry,2009,20(18):2149-2153.DOI:10.1016/j.tetasy.2009.08.009.
[31] LEUNG A E,RUBBIANI R,GASSER G,et al.Enantioselective total syntheses of the proposed structures of prevezol B and evaluation of anti-cancer activity[J].Organic and Biomolecular Chemistry,2014,12(41):8239-8246.DOI:10.1039/C4OB01662A.
[32] 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.
[33] SILVA A C R D,LOPES P M,AZEVEDO M M B D,et al.Biological activities of α-pinene and β-pinene Enantiomers[J].Molecules,2012,17(6):6305-6316.DOI:10.3390/molecules17066305.

相似文献/References:

[1]杨道茂,陈煌.近海海洋真菌生物转化(+)-柠檬烯[J].华侨大学学报(自然科学版),2020,41(1):67.[doi:10.11830/ISSN.1000-5013.201904020]
　YANG Daomao,CHEN Huang.Biotransformation of(+)-Limoneneby Offshore Marine Fungi[J].Journal of Huaqiao University(Natural Science),2020,41(4):67.[doi:10.11830/ISSN.1000-5013.201904020]

备注/Memo

备注/Memo:
收稿日期: 2023-02-03
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); 福建省个人和团队科技员项目(2022年度); 华侨大学高层次人才科研启动资金资助项目(Z15X0004)
更新日期/Last Update: 2023-07-20