林产化学与工业 ›› 2020, Vol. 40 ›› Issue (5): 10-16.doi: 10.3969/j.issn.0253-2417.2020.05.002
收稿日期:
2020-03-14
出版日期:
2020-10-28
发布日期:
2020-10-31
通讯作者:
姜贵全
E-mail:jiangguiqian11@163.com
作者简介:
李特(1997—),女,吉林四平人,硕士生,主要从事天然产物方面的研究
基金资助:
Te LI1,Jianxi SONG1,Zhuorui ZHANG2,Guiquan JIANG1()
Received:
2020-03-14
Online:
2020-10-28
Published:
2020-10-31
Contact:
Guiquan JIANG
E-mail:jiangguiqian11@163.com
摘要:
将缩合单宁降解为相对分子质量较小的单宁低聚体或单体,对于提高其生物利用度和高附加值利用具有非常深远的意义。在全面地综述了缩合单宁在微生物降解(真菌和细菌)、化学降解(酸降解、碱降解、贵金属催化降解和生物酶解法)、树脂催化降解等领域取得的研究进展之后,对当前缩合单宁降解存在的问题及解决方案进行了总结和归纳,并展望了未来的发展方向。
中图分类号:
李特,宋见喜,张卓睿,姜贵全. 缩合单宁降解方法研究进展[J]. 林产化学与工业, 2020, 40(5): 10-16.
Te LI,Jianxi SONG,Zhuorui ZHANG,Guiquan JIANG. Research Progress of Degradation Methods of Condensed Tannin[J]. Chemistry and Industry of Forest Products, 2020, 40(5): 10-16.
1 | 石碧, 狄莹. 植物多酚[M]. 北京: 科学出版社, 2000, 5 |
SHIB, DIY. Plant Polyphenols[M]. Beijing: Science Press, 2000, 5 | |
2 | XIE D Y , DIXON R A . Proanthocyanidin biosynthesis-still more questions than answers?[J]. Phytochemistry, 2005, 66 (18): 2127- 2144. |
3 | 孙达旺. 植物单宁化学[M]. 北京: 中国林业出版社, 1992: 130- 214. 130-133, 213-214 |
SUND W. Plant Tannin Chemistry[M]. Beijing: China Forestry Press, 1992: 130- 214. 130-133, 213-214 | |
4 | 张慧文, 张玉, 马超美. 原花青素的研究进展[J]. 食品科学, 2015, 36 (5): 296- 304. |
ZHANGH W, ZHANGY, MAC M. Research progress of proanthocyanidins[J]. Food Science, 2015, 36 (5): 296- 304. | |
5 | TROSZYNSKA A , CISKA E . Phenolic compounds of seed coats of white and coloured varieties of pea (Pisum sativum L[J]. Czech Journal of Food Sciences, 2018, 20 (1): 15- 22. |
6 | Grzesik M , Katarzyna N , Bartosz G , et al. Antioxidant properties of catechins:Comparison with other antioxidants[J]. Food Chemistry, 2018, 241 (15): 480- 492. |
7 | 张盼, 胡月, 唐晗, 等. 儿茶素氧化物的结构、形成机理及生物活性研究进展[J]. 现代食品, 2020, (8): 72- 75. |
ZHANGP, HUY, TANGH, 等. Research progress on the structure, formation mechanism and biological activity of catechin oxide[J]. Modern Food, 2020, (8): 72- 75. | |
8 | Anitha S , Krishnan S , Senthilkumar K , et al. Theoretical investigation on the structure and antioxidant activity of (+) catechin and (-)epicatechin-a comparative study[J]. Molecular Physics, 2020, (3): 1- 12. |
9 | LI X C , HE C F , SONG L Y , et al. Antimicrobial activity and mechanism of Larch bark procyanidins against Staphylococcus aureus[J]. Acta Biochimica et Biophysica Sinica, 2017, 49 (12): 1058- 1066. |
10 | SADEGHI M , ZOLFAGHARI B , JAHANIANNAJAFABADI A , et al. Anti-pseudomonas activity of essential oil, total extract, and proanthocyanidins of Pinus eldarica Medw. bark[J]. Research in Pharmaceutical Sciences, 2016, 11 (1): 58- 64. |
11 | AKTER S, NETZE M, TTNGGI U, et al. Antioxidant rich extracts of Terminalia ferdinandiana inhibit the growth of foodborne bacteria[ J / OL]. Foods, 2019, 8(8): 1-18[2020-01-14]. http://doi.org/10.1016/j.indcrop.2020.1-18[2020-01-14]. http://www.mdpi.com/2304-8158/8/8/28/pdf. DOI:10.3390/foods8080281 |
12 | SHI J, WANG Y Z, WEI H R, et al. Structure analysis of condensed tannin from rice straw and its inhibitory effect on Staphylococcus aureus[J / OL]. Industrial Crops and Products, 2020, 145: 1-11[2020-01-14]. http://doi.org/10.1016/j.indcrop.2020.112130 |
13 | 索昊, 田若晨, 张舒婷, 等. 葡萄酒中高分子聚合多酚的研究进展[J]. 中外葡萄与葡萄酒, 2018, (6): 78- 81. |
SUOH, TIANR C, ZHANGS T, 等. Research advance of high-molecular-mass polymeric polyphenols in red wine[J]. Sino-Overseas Grapevine and Wine, 2018, (6): 78- 81. | |
14 |
MARMOL I , QUERO J , JIMENEZMORENO N , et al. A systematic review of the potential uses of pine bark in food industry and health care[J]. Trends in Food Science and Technology, 2019, 88, 558- 566.
doi: 10.1016/j.tifs.2018.07.007 |
15 | SHARMA A, GOYAL R, SHARMA L, et al. Potential biological efficacy of Pinus plant species against oxidative, inflammatory and microbial disorders[J / OL]. BMC Complementary and Alternative Medicine, 2015, 16 (1): 1-11[2020-01-01]. https://linkspringer.com/content/pdf/10.1186/S12906-016-1011-6.pdf. |
16 | MANGELS D R , MOHLER E R . Catechins as potential mediators of cardiovascular health[J]. Arteriosclerosis, Thrombosis, and Vascular Biology, 2017, 37 (5): 757- 763. |
17 | CUI C , SHI A , BAI S , et al. Novel antihypertensive prodrug from grape seed proanthocyanidin extract via acid-mediated depolymerization in the presence of captopril:Synthesis, process optimization, and metabolism in rats[J]. Journal of Agricultural and Food Chemistry, 2018, 66 (14): 3700- 3707. |
18 | SCHOFIELD P , MBUGUA D , PELL A N , et al. Analysis of condensed tannins:A review[J]. Animal Feed Science and Technology, 2001, 91 (1): 21- 40. |
19 | 简晓昀, 滕博, 周南, 等. 曲霉对杨梅栲胶溶液的微生物降解[J]. 皮革科学与工程, 2016, 26 (2): 5- 8. |
JIANX Y, TENGB, ZHOUN, 等. Biodegradation of bayberry extract by Aspergillus[J]. Leather Science and Engineering, 2016, 26 (2): 5- 8. | |
20 | 张金伟, 简晓昀, 滕博, 等. 黄柄曲霉对杨梅栲胶的降解过程研究[J]. 中国科技论文, 2016, 11 (24): 2859- 2864. |
ZHANGJ W, JIANX Y, TENGB, 等. Study on the degradation process of bayberry tannin extract by Aspergillus flavus[J]. Chinese Sciencepaper, 2016, 11 (24): 2859- 2864. | |
21 | KNUDSON L . Tanninc acid fermentation[J]. Journal of Biological Chemistry, 1913, 14, 159- 202. |
22 | 兰平, 马泽宇, 叶柳青, 等. 微生物降解葡萄皮单宁研究[J]. 林业工程学报, 2017, 2 (5): 58- 63. |
LANP, MAZ Y, YEL Q, 等. Microbial degradation of grape pomace tannins[J]. Journal of Forestry Engineering, 2017, 2 (5): 58- 63. | |
23 | FIELD J A , LETTINGA G . The methanogenic toxicity and anaerobic degradability of a hydrolyzable tannin[J]. Water Research, 1987, 21 (3): 367- 374. |
24 | MCSWEENEY C S , PALMER B , BUNCH R J , et al. Isolation and characterization of proteolytic ruminal bacteria from sheep and goats fed the tannin-containing shrub legume Calliandra calothyrsus[J]. Applied and Environmental Microbiology, 1999, 65 (7): 3075- 3083. |
25 | 陈度宇, 王森, 张宇, 等. 一株缩合单宁降解菌的筛选、鉴定及降解效果分析[J]. 生物技术进展, 2018, 8 (4): 345- 350. |
CHEND Y, WANGS, ZHANGY, 等. Screening and identification of a condensed tannin degrading bacteria and its degradation effect[J]. Progress in Biotechnology, 2018, 8 (4): 345- 350. | |
26 | MATTHEWS S , MILA I , SCALBERT A , et al. Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles[J]. Journal of Agricultural and Food Chemistry, 1997, 45 (4): 1195- 1201. |
27 | 魏冠红.高聚原花青素的水解工艺研究[D].杭州:浙江大学, 2006. |
WEI G H. Study on the hydrolysis process of high polymer proanthocyanidins[D]. Hangzhou: Zhejiang University, 2006. | |
28 | 文魁山.葡萄籽原花青素高聚体的解聚方法与条件优化的研究[D].杭州:浙江大学, 2018. |
WEN K S. Study on the depolymerization and optimization of grape seed polymeric proanthocyanidins[ D ]. Hangzhou: Zhejiang University, 2018. | |
29 | QI Y J , ZHANG H , AWIKA J M , et al. Depolymerization of sorghum procyanidin polymers into oligomers using HCl and epicatechin:Reaction kinetics and optimization[J]. Journal of Cereal Science, 2016, 70, 170- 176. |
30 | 齐雅静.不同结构原花青素的制备及对食品中丙烯酰胺生成的影响[D].无锡:江南大学, 2019. |
QI Y J. Preparation of proanthocyanidins with different structures and their effects on the formation of acrylamide in foods[D]. Wuxi: Jiangnan University, 2019. | |
31 | OREJOL J, MATSUO Y, SAITO Y, et al. Characterization of proanthocyanidin oligomers of Ephedra sinica[J / OL]. Molecules, 2017, 22(8): 1-18[2020-01-14]. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152249. DOI:10.3901molecules22081308. |
32 |
ZHANG A B , LI J J , ZHANG S F , et al. Characterization and acid-catalysed depolymerization of condensed tannins derived from larch bark[J]. RSC Advances, 2017, 7 (56): 35135- 35146.
doi: 10.1039/C7RA03410E |
33 |
BILLERACH G , ROUMÉAS L , DUBREUCQ E , et al. Furanolysis with menthofuran:A new depolymerization method for analyzing condensed tannins[J]. Journal of Agricultural and Food Chemistry, 2020, 68 (10): 2917- 2926.
doi: 10.1021/acs.jafc.9b00497 |
34 | 张惠.莲房高聚体原花青素催化降解工艺研究[D].郑州:郑州大学, 2018. ZHANG H. Study on the catalytic degradation process of high polymer procyanidins from lotus seed pot[ D ]. Zhengzhou: Zhengzhou University, 2018. |
35 |
LUO L X , CUI Y , CHENG J H , et al. An approach for degradation of grape seed and skin proanthocyanidin polymers into oligomers by sulphurous acid[J]. Food Chemistry, 2018, 256, 203- 211.
doi: 10.1016/j.foodchem.2018.02.097 |
36 | NI L W , ZHAO F B , LI B L , et al. Antioxidant and fluorescence properties of hydrogenolyzised polymeric proanthocyanidins prepared using SO42-/ZrO2 solid superacids catalyst[J]. Molecules, 2018, 23 (10): 2445. |
37 | WHITE B L , HOWARD L R , PRIOR R L , et al. Release of bound procyanidins from cranberry pomace by alkaline hydrolysis[J]. Journal of Agricultural and Food Chemistry, 2010, 58 (13): 7572- 7579. |
38 | 纪秀凤, 吕长鑫, 芦宇, 等. 响应面优化碱降解红树莓籽高聚原花青素及对降血糖酶活性抑制作用[J]. 食品工业科技, 2019, 40 (4): 159- 165. |
JIX F, LYUC X, LUY, 等. Response surface optimization of alkali degradation process of high polymeric proanthocyanidins from red raspberry seed and inhibitory activities on hypoglycemic enzymes[J]. Food Industry Technology, 2019, 40 (4): 159- 165. | |
39 | LIU J, WANG L L, LI J J, et al. Degradation mechanism of Acacia mangium tannin in NaOH / urea aqueous solution and application of degradation products in phenolic adhesives[J]. International Journal of Adhesion and Adhesives, 2020, 98:1-10[2020-01-02]. https://doi.org/10.1016/j.ijahadh.2020.102556. |
40 | 张杰, 王文雅, 袁其朋. NaOH处理对霞多丽葡萄籽原花青素的影响[J]. 食品科学, 2020, 41 (4): 41- 51. |
ZHANGJ, WANGW Y, YUANQ P. Effect of NaOH pretreatment on depolymerization and in vitro antioxidant activity of chardonnay grape seed procyanidins[J]. Food Science, 2020, 41 (4): 41- 51. | |
41 | FOO L Y . Polymeric proanthocyanidins of photinia glabrescens, modification of molecular weight and nature of products from hydrogenolysis[J]. Phytochemistry, 1982, 21 (7): 1741- 1746. |
42 | 杜晓, 陆忠兵, 陶毅, 等. 落叶松多聚原花青素催化氢解产物抗氧化活性研究[J]. 四川大学学报(工程科学版), 2005, 37 (6): 65- 70. |
DUX, LUZ B, TAOY, 等. Study on the antioxidant activity of catalytic hydrogenolysis products of polymeric proanthocyanidins from Larix gmelini bark[J]. Journal of Sichuan University (Engineering Science Edition), 2005, 37 (6): 65- 70. | |
43 | 姜贵全.落叶松树皮原花青素的分级纯化及催化降解研究[D].哈尔滨:东北林业大学, 2013. |
JIANG G Q. Study on the fractionation, purification and catalysed degradation of proanthocyanidins from larch bark[ D]. Harbin: Northeast Forestry University, 2013. | |
44 | LI Z , ZENG J J , TONG Z H , et al. Hydrogenolytic depolymerization of procyanidin polymers from hi-tannin sorghum bran[J]. Food Chemistry, 2015, 188, 337- 342. |
45 | ZHU H F , LI P Z , REN S X , et al. Low-cost Ru/C-catalyzed depolymerization of the polymeric proanthocyanidin-rich fraction from bark to produce oligomeric proanthocyanidins with antioxidant activity[J]. ACS Omega, 2019, 4 (15): 16471- 16480. |
46 | OSMAN A M , WONG K K Y . Laccase (EC 1. 10. 3. 2) catalyses the conversion of procyanidin B-2 (epicatechin dimer) to type A-2[J]. Tetrahedron Letters, 2006, 48 (7): 1163- 1167. |
47 | 苏惠娟.葡萄籽原花青素的降解工艺研究[D].北京:北京化工大学, 2016. |
SU H J. Study on the degradation process of grape seed proanthocyanidins[D]. Beijing: Beijing University of Chemical Technology, 2016. | |
48 | 姜贵全, 张卓睿, 张诗朦, 等. 落叶松树皮多聚原花青素的树脂催化降解及抗氧化活性[J]. 北京林业大学学报, 2018, 40 (9): 118- 126. |
JIANGG Q, ZHANGZ R, ZHANGS M, 等. Degradation and of polymeric proanthocyanidin from larch bark catalyzed by resin and antioxidant activity[J]. Journal of Beijing Forestry University, 2018, 40 (9): 118- 126. |
[1] | 武海棠, 郑冀鲁, 张军华, 黄晓华. 先驱体转化法制备ZrC木质陶瓷及其性能分析[J]. 林产化学与工业, 2016, 36(5): 23-29. |
[2] | 尹斌, 曾韬, 王雪源. 超临界正己烷中松香酸一元醇酯高压氢解还原反应[J]. 林产化学与工业, 2015, 35(1): 51-56. |
[3] | 张盛明, 刘亮, 马艳丽, 方桂珍. SO42-/ZrO2固体超强酸催化碱木质素氢还原反应[J]. 林产化学与工业, 2014, 34(5): 15-21. |
[4] | 张静;徐鸽;于大钢;吴国平;陈和新. 衍生还原裂解法研究木质素类药物的结构[J]. 林产化学与工业, 2013, 33(2): 71-76. |
[5] | 杨静;蒋剑春;张宁;卫民;赵剑. 造纸蒸煮废液水解制糖的研究[J]. 林产化学与工业, 2013, 33(2): 119-122. |
[6] | 贾羽洁;蒋剑春;孙康. 活性炭载Au-Ru合金作为直接甲酸燃料电池阴极催化剂的研究[J]. 林产化学与工业, 2012, 32(3): 19-22. |
[7] | 徐曼;陈笳鸿;汪咏梅;吴冬梅;吴在嵩. 油茶果壳单宁成分的提取及其分析试验初报[J]. 林产化学与工业, 2009, 29(S1): 187-191. |
[8] | 马李一;王有琼;张重权;甘瑾;郑华;郭元享;赵虹;段琼芬. 虫白蜡还原法制备高级烷醇混合物研究[J]. 林产化学与工业, 2009, 29(5): 6-10. |
[9] | 段文贵;耿哲;张加研;申长茂. 改性松香-缩合单宁酯的制备及性质[J]. 林产化学与工业, 2009, 29(3): 6-12. |
[10] | 张亮亮;林益明;. 木榄花萼缩合单宁制备花青定及抗氧化能力研究[J]. 林产化学与工业, 2008, 28(6): 1-5. |
[11] | 李敏;向平;杨志伟;向成;林鹏;林益明;. 杨梅不同部位单宁含量与结构研究[J]. 林产化学与工业, 2008, 28(3): 55-60. |
[12] | 陈笳鸿. 我国树木提取物开发利用现状与展望[J]. 林产化学与工业, 2008, 28(3): 111-116. |
[13] | 张亮亮;李敏;林鹏;林益明;. 李子果肉单宁结构及其抗氧化能力的研究[J]. 林产化学与工业, 2008, 28(04): 1-6. |
[14] | 孙震;赵振东;李冬梅;刘先章. 金合欢基溴合成角鲨烯反应及异构体形成机理的研究[J]. 林产化学与工业, 2005, 25(2): 1-5. |
[15] | 王应红;陈武勇;黄瓒. 儿茶素与Cr6+氧化还原反应的影响因素及动力学特征[J]. 林产化学与工业, 2005, 25(2): 21-24. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||