Research progress in biotransformation of plant lignans

  • FENG Chengcheng ,
  • ZHANG Wen ,
  • CAI Zizhe ,
  • LI Ying ,
  • WANG Yong ,
  • ZHANG Ning
Expand
  • 1(Department of Food Science and Engineering,Jinan University,Guangzhou 510632,China)
    2(Jinan University-Saskatchewan Oilseed Joint Laboratory,Guangzhou 510632,China)
    3(School of Nursing,Yichun Vocational and Technical College,Yichun 336000,China)

Received date: 2020-09-09

  Revised date: 2020-10-27

  Online published: 2021-07-16

Abstract

Phytoestrogens are weak oestrogens found in plants or derived from plant precursors.They are structurally similar to endogenous oestrogens which can have both oestrogenic and anti-oestrogenic effects.Lignans are phytoestrogens found in seeds such as flaxseeds,vegetables,fruits,beverages,and other daily foods.Dietary lignans and their derived metabolites have antioxidant,anti-malignant cell proliferation,estrogen-like properties and other functions,and can prevent breast and prostate cancer,cardiovascular diseases and diabetes.Due to their low bioavailability,dietary lignans must be converted into enterolignans such as enterodiol (END) and enterolactone (ENL) to exert their beneficial effects.The conversion of dietary lignans results from the activities of both dominant and subdominant anaerobic bacterial communities in the human intestinal tract.Therefore,the bioavailability of dietary lignans can be improved by transforming them in vitro.Biotransformation is a much more economical,efficient and environmentally friendly method of mass production of enterolignans from dietary lignans than chemical synthesis.The structure,species and distribution of lignans were briefly described,and the intestinal microbial metabolism mechanism of lignans were discussed,as well as the research progress of microbial and enzymatic transformation of lignans in vitro were reviewed.

Cite this article

FENG Chengcheng , ZHANG Wen , CAI Zizhe , LI Ying , WANG Yong , ZHANG Ning . Research progress in biotransformation of plant lignans[J]. Food and Fermentation Industries, 2021 , 47(11) : 295 -302 . DOI: 10.13995/j.cnki.11-1802/ts.025579

References

[1] LANDETE J M.Plant and mammalian lignans:A review of source,intake,metabolism,intestinal bacteria and health[J].Food Research International,2012,46(1):410-424.
[2] HAMEED A S S,RAWAT P S,MENG X F,et al.Biotransformation of dietary phytoestrogens by gut microbes:A review on bidirectional interaction between phytoestrogen metabolism and gut microbiota[J].Biotechnology Advances,2020,43:107 576.
[3] DURAZZO A,LUCARINI M,CAMILLI E,et al.Dietary lignans:Definition,description and research trends in databases development[J].Molecules,2018,23(12):3 251.
[4] 赵德宝,戴志刚,杨学,等.亚麻木酚素合成及相关基因的研究进展[J].农业科技通讯,2015(7):242-245.
ZHAO D B,DAI Z G,YANG X,et al.Research progress in the synthesis of flax lignans and related genes[J].Bulletin of Agricultural Science and Technology,2015(7):242-245.
[5] LANDETE J M,ARQUES J L,MEDINA M,et al.Bioactivation of phytoestrogens:Intestinal bacteria and health[J].Critical Reviews in Food Science and Nutrition,2016,56(11):1 826-1 843.
[6] QUARTIERI A,GARCIA-VILLALBA R,AMARETTI A,et al.Detection of novel metabolites of flaxseed lignans in vitro and in vivo[J].Molecular Nutrition & Food Research,2016,60(7):1 590-1 601.
[7] PAN J Y,CHEN S Z,YANG M H,et al.An update on lignans:Natural products and synthesis[J].Natural Product Reports,2009,26(10):1 251-1 292.
[8] PEIROTEN Á,BRAVO D,LANDETE J M.Bacterial metabolism as responsible of beneficial effects of phytoestrogens on human health[J].Critical Reviews in Food Science and Nutrition,2020,60(11):1 922-1 937.
[9] 滕晖,向大位.肠内脂与肠二醇的生理活性研究进展[J].中南药学,2012(3):219-223.
TENG H,XIANG D W.Research progress on the physiological activities of enterodiol and enterolactone[J].Central South Pharmacy,2012(3):219-223.
[10] ELKON I M.Taxonomic and functional characterization of human gut microbes involved in dietary plant lignan metabolism[D].Seattle:University of Washington,2015.
[11] GUTTE K B,SAHOO A K,RANVEER R C.Bioactive components of flaxseed and its health benefits[J].International Journal of Pharmaceutical ences Review and Research,2015,31(1):42-51.
[12] PENALVO J L,HAAJANEN K M,BOTTING N P,et al.Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry[J].Journal of Agricultural and Food Chemistry,2005,53(24):9 342-9 347.
[13] THOMPSON L U,BOUCHER B A,LIU Z,et al.Phytoestrogen content of foods consumed in Canada,including isoflavones,lignans,and coumestan[J].Nutrition & Cancer,2006,54(2):184-201.
[14] MILDER I E J,ARTS I C W,VAN DE PUTTE B,et al.Lignan contents of dutch plant foods:A database including lariciresinol,pinoresinol,secoisolariciresinol and matairesinol[J].The British Journal of Nutrition,2005,93(3):393-402.
[15] SMEDS A I,EKLUND P C,SJOHOLM R E,et al.Quantification of a broad spectrum of lignans in cereals,oilseeds,and nuts[J].Journal of Agricultural & Food Chemistry,2007,55(4):1 337-1 346.
[16] PENALVO J L,ADLERCREUTZ H,UEHARA M,et al.Lignan content of selected foods from Japan[J].Journal of Agricultural and Food Chemistry,2008,56(2):401-409.
[17] SETCHELL K D R,LAWSON A M,MITCHELL F L,et al.Lignans in man and animal species[J].Nature,1980,287(5 784),740-742.
[18] LANDETE J M,GAYA P,RODRIGUEZ E,et al.Probiotic bacteria for healthier aging:Immunomodulation and metabolism of phytoestrogens[J].BioMed Research International,2017,2017:1-10.
[19] CLAVEL T,BORRMANN D,BRAUNE A,et al.Occurrence and activity of human intestinal bacteria involved in the conversion of dietary lignans[J].Anaerobe,2006,12(3):140-147.
[20] CLAVEL T,HENDERSON G,ENGST W,et al.Phylogeny of human intestinal bacteria that activate the dietary lignan secoisolariciresinol diglucoside[J].FEMS Microbiology Ecology,2006,55(3):471-478.
[21] CLAVEL T,LIPPMAN R,GAVINI F,et al.Clostridium saccharogumia sp.nov.and Lactonifactor longoviformis gen.nov.,sp.nov.,two novel human faecal bacteria involved in the conversion of the dietary phytoestrogen secoisolariciresinol diglucoside[J].Systematic and Applied Microbiology,2007,30(1):16-26.
[22] RONCAGLIA L,AMARETTI A,RAIMONDI S,et al.Role of bifidobacteria in the activation of the lignan secoisolariciresinol diglucoside[J].Applied Microbiology & Biotechnology,2011,92(1):159-168.
[23] JIN J S,ZHAO Y F,NAKAMURA N,et al.Isolation and characterization of a human intestinal bacterium,Eubacterium sp.ARC-2,capable of demethylating arctigenin,in the essential metabolic process to enterolactone[J].Biological & Pharmaceutical Bulletin,2007,30(5):904-911.
[24] JIN J S,KAKIUCHI N,HATTORI M.Enantioselective oxidation of enterodiol to enterolactone by human intestinal bacteria[J].Biological & Pharmaceutical Bulletin,2007,30(11):2 204-2 206.
[25] JIN J S,HATTORI M.Further studies on a human intestinal bacterium Ruminococcus sp.END-1 for transformation of plant lignans to mammalian lignans[J].Journal of Agricultural and Food Chemistry,2009,57(16):7 537-7 542.
[26] YODER S C,LANCASTER S M,HULLAR M A J,et al.Diet-Microbe Interactions in the Gut[M].Amsterdam:Elsevier Inc,2015.
[27] CLAVEL T,DORE J,BLAUT M.Bioavailability of lignans in human subjects[J].Nutrition Research Reviews,2006,19(2):187-196.
[28] WOTING A N,CLAVEL T,LOH G,et al.Bacterial transformation of dietary lignans in gnotobiotic rats[J].FEMS Microbiology Ecology,2010,72(3):507-514.
[29] BESS E N,BISANZ J E,YARZA F,et al.Genetic basis for the cooperative bioactivation of plant lignans by Eggerthella lenta and other human gut bacteria[J].Nature microbiology,2020,5(1):56-66.
[30] JAN K C,HWANG L S,HO C T.Biotransformation of sesaminol triglucoside to mammalian lignans by intestinal microbiota[J].Journal of Agricultural and Food Chemistry,2009,57(14):6 101-6 106.
[31] GAYA P,MEDINA M,SANCHEZ-JIMENEZ A,et al.Phytoestrogen metabolism by adult human gut microbiota[J].Molecules,2016,21(8):1 034-1 051.
[32] JIN J,ZHAO Y,NAKAMURA N,et al.Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria[J].Biological & Pharmaceutical Bulletin,2007,30(11):2 113-2 119.
[33] JIN J S,HATTORI M.Human intestinal bacterium,strain END-2 is responsible for demethylation as well as lactonization during plant lignan metabolism[J].Biological & Pharmaceutical Bulletin,2010,33(8):1 443-1 447.
[34] WANG C,MA X,YANG D,et al.Production of enterodiol from defatted flaxseeds through biotransformation by human intestinal bacteria[J].BMC Microbiology,2010,10(1):115.
[35] CORTES C,GAGNON N,BENCHAAR C,et al.In vitro metabolism of flax lignans by ruminal and faecal microbiota of dairy cows[J].Journal of Applied Microbiology,2008,105(5):1 585-1 594.
[36] LIU Z,SAARINEN N M,THOMPSON L U.Sesamin is one of the major precursors of mammalian lignans in sesame seed (Sesamum indicum) as observed in vitro and in rats[J].Journal of Nutrition,2006,136(4):906-912.
[37] 杜木香.亚麻木酚素的纯化、结构修饰及其衍生物的生物活性研究[D].广州:暨南大学,2019.
DU M X.Purification,structural modification of flaxseed lignan and biological activity of its derivatives[D].Guangzhou:Jinan University,2019.
[38] HWANG C F,WANG H E,KER Y B,et al.The limited deglucosylation process of β-glucosidase in Bacillus cereus H62L for biotransforming secoisolariciresinol diglucoside into mammalian lignans[J].Process Biochemistry,2011,46(8):1 632-1 640.
[39] HWANG C F,YIN T C,CHANG N Y,et al.Efficiency of a SDG-β-glucosidase from Bacillus altitudinis HK02 for the deglycation of glycosides from flaxseeds[J].Process Biochemistry,2015,50(12):2 188-2 193.
[40] ZHOU Y,ZHU S,YANG D,et al.Characterization of Klebsiella sp.strain S1:A bacterial producer of secoisolariciresinol through biotransformation[J].Canadian Journal of Microbiology,2017,63(1):1-10.
[41] GAYA P,PEIROTEN A,MEDINA M,et al.Bifidobacterium adolescentis INIA P784:The first probiotic bacterium capable of producing enterodiol from lignan extracts[J].Journal of Functional Foods,2017,29:269-274.
[42] BRAVO D,PEIROTEN A,ALVAREZ I,et al.Phytoestrogen metabolism by lactic acid bacteria:Enterolignan production by Lactobacillus salivarius and Lactobacillus gasseri strains[J].Journal of Functional Foods,2017,37:373-378.
[43] PEIROTEN A,GAYA P,ALVAREZ I,et al.Influence of different lignan compounds on enterolignan production by Bifidobacterium and Lactobacillus strains[J].International Journal of Food Microbiology,2019,289:17-23.
[44] ZHU H Y,LI M X,YANG D H,et al.Biotransformation of the SDG in defatted flaxseed into END co-cultured by three single bacterial colonies[J].Process Biochemistry,2014,49(1):19-24.
[45] 陈家兴,李淼鑫,朱红云,等.人体肠道菌生物转化亚麻木酚素产生4,4′-二羟基肠二醇的条件研究[J].中国科技论文,2014,9(12):1 389-1 392.
CHEN J X,LI M X,ZHU H Y,et al.Biotransformation of defatted flaxseed into 4,4′-dihydroxyenterodiol cultured by human intestinal bacteria[J].China Science Paper,2014,9(12):1 389-1 392.
[46] LI M X,ZHU H Y,YANG D H,et al.Production of secoisolariciresinol from defatted flaxseed by bacterial biotransformation[J].Journal of Applied Microbiology,2012,113(6):1 352-1 361.
[47] MUNOZ O,FUENTEALBA C,AMPUERO D,et al.The effect of Lactobacillus acidophilus and Lactobacillus casei on the in vitro bioaccessibility of flaxseed lignans (Linum usitatissimum L.)[J].Food & Function,2018,9(4):2 426-2 432.
[48] 刘树林.一种肠二醇和/或肠内酯的生物转化方法:中国,CN109588368A[P].2019-04-09.
LIU S L.A bioconversion method for enterodiol and/or enterolactone:China,CN109588368A[P].2019-04-09.
[49] 刘树林. 脱脂亚麻籽生物体内转化高效生成动物木酚素方法:中国,CN108450879A[P].2018-08-28.
LIU S L.Method for high-efficient generation of animal lignanoid through organism internal conversion of degreased linseeds:China,CN108450879A[P].2018-08-28.
[50] FUKUMITSU S,HAZAMA K,TAMURA M.Combination of intestinal bacteria having plant lignan assimilation activity,and use of the same:Japan,JP2015204784A[P].2015-11-19.
Outlines

/