Research Progress on Composition, Extraction and Physiological Activity of Pea Polyphenols
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摘要: 豌豆多酚是广泛存在于豌豆中的次级代谢产物，主要包括黄酮（白杨素、山奈酚、槲皮素）、酚酸（对香豆酸、芥子酸、阿魏酸）和单宁（儿茶素）3类组分。豌豆多酚的含量、种类及分布取决于豌豆品种，但在其生长过程中又受到环境和诱导因素的影响。豌豆多酚的提取方法由低效的溶剂萃取法，逐步向高效率、高提取率的微波萃取技术转变，其生理活性研究也逐步向分子和细胞水平发展，应用范围逐渐扩展至肉制品、水产品及面制品等产业中。为进一步了解豌豆多酚的化学性质及潜在利用价值，本文对豌豆中多酚的分布，影响豌豆多酚种类和含量的因素，豌豆多酚的分离提取、生理活性及其在食品工业中的应用进行了详细阐述，以期为豌豆多酚的开发与研究提供理论依据。Abstract: Pea polyphenols are secondary metabolites widely existing in peas, mainly including flavonoids (populin, kaempferol, quercetin), phenolic acids (p-coumaric acid, erucic acid, ferulic acid) and tannins (catechins). The content, species and distribution of pea polyphenols depend on pea varieties, but they are affected by environment and inducing factors in the process of their growth. The extraction method of pea polyphenols has gradually changed from inefficient solvent extraction to microwave extraction technology with high efficiency and high extraction rate. The research on its physiological activity has gradually developed to the molecular and cellular level, and its application scope has gradually expanded to meat products, aquatic products, flour products and other industries. In order to further understand the chemical properties and potential utilization value of pea polyphenols, this paper expounds in detail the distribution of pea polyphenols, the factors affecting the types and content of pea polyphenols, the separation and extraction, physiological activity and its application in food industry, in order to provide a theoretical basis for the development and research of pea polyphenols.
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Key words:
- pea /
- polyphenols /
- extraction /
- type /
- identification /
- physiological activity /
- bacteriostasis /
- antioxidant
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图 1 植物多酚合成代谢途径
Figure 1. Synthetic and metabolic pathways of plant polyphenols
注：PAL：苯丙氨酸解氨酶（phenylalanine ammonia-lyase）；C4H：肉桂酸羟化酶（cinnamic acid-4-hydroxylase）；4CL：香豆酰-CoA连接酶（4-coumarate-CoA ligase）；CHS：查尔酮合酶（chalcone synthase）；SbCLL-7：肉桂酰CoA连接酶（cinnamoyl-CoA ligase-7）；SbCHS-2：松属素查尔酮合成酶（chalcone synthase-2）；SbCHI：查尔酮异构酶（chalcone isomerase）；SbFNSⅡ-2：Ⅱ型黄酮合成酶（flavone synthase II gene-2）；C3H：对香豆酸-3-羟化酶（coumarate 3-hydroxylase）；COMT：咖啡酸氧甲基转移酶（caffeic acid O-methyltransferase）；F5H：阿魏酸-5-羟化酶（ferulic acid 5-hydroxylase）；CCR：肉桂酰CoA还原酶（cinnamoyl-CoA reductas）；CAD：肉桂醇脱氢酶（cinnamoyl alcohol dehydrogenas）；CHI: 查尔酮异构酶（chalcone isomerase）F3H：黄烷酮-3-羟基化酶（flavanone-3-hydroxylase）；F3ʹH：黄烷酮-3’-羟基化酶（flavanone-3'-hydroxylase）；FLS：黄酮醇合成酶（flavonol synthase）；DFR：黄酮醇-4-还原酶（dihydroflavonol 4-reductase）；LAR：无色花青素还原酶（leucoanthocyanidin reductase）；ANS：花青素合成酶（anthocyanidin synthase）；ANR：花青素还原酶（anthocyanidin reductase）。
表 1 豌豆中常见酚类物质的化学结构
Table 1. Chemical structures of common phenols in peas
类别 名称 含量 化学结构 黄酮类化合物 白杨素[19]
chrysin57.60~65.90 
山奈酚[17]
kaempferol
40.00~80.00
槲皮素[17]
quercetin
440.00~690.00
酚酸类化合物 对香豆酸[6]
p-Hydroxycinnamic acid870.02±12.51 
芥子酸[6]
sinapic acid762.09±10.14 
阿魏酸[6]
ferulic acid3141.61±253.26 
单宁类化合物 儿茶素[20]
catechin102.30±5.46 
注：白杨素含量以鲜重（µg/100 g）计；原花青素以鲜重（mg/100 g）计；对香豆酸、芥子酸和阿魏酸以（mg/100 g）多酚提取物计；其它物质含量均以干质量（mg/100 g）计。 
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表 2 不同产地豌豆多酚的鉴定
Table 2. Identification of pea polyphenols from different producing areas
产地及品种 原料 鉴定方法 多酚组成和含量 主要结论 福建省漳州市 20种豌豆尖 HPLC 生长中期：槲皮素7.55~12.73（mg/g）、山奈酚0.53~4.35（mg/g）
生长后期：槲皮素3.70~10.92（mg/g）、山奈酚0.80~2.65（mg/g）构建了豌豆尖中槲皮素和山奈酚定性定量的HPLC双波长法；豌豆尖槲皮素和山奈酚含量受品种和生长时期的影响[4] 福建省龙岩市 豌豆籽粒 HPLC 共10种；单体酚含量（µg/100 mg）：4-羟基苯甲酸（130.84）、3-（3，4-二羟基苯基）丙酸（487.39）、香草酸（281.14）、绿原酸（290.52）、咖啡酸（397.44）、丁香酸（59.58）、2-羟基苯乙酸（621.93）、对香豆酸（870.02）、阿魏酸（3141.61）、芥子酸（762.09） 构建了豌豆籽粒中10种多酚的HPLC方法[6] 克罗地亚（MBK88、MBK90、MBK168和MBK173） 4种豌豆种皮 UHPLC-LTQ OrbiTrap MS 共41种；总酚含量（不同品种mg/g）：MBK88（14.35±0.66）、MBK90（2.57±0.12）、MBK168（30.56±1.30）、MBK173（21.56±0.96）
；单体酚含量（mg/kg）：原儿茶酸（26.30~127.20）、表没食子儿茶素（239.30~325.30）、没食子儿茶素（62.30~99.10）构建了豌豆籽粒中41种多酚的UHPLC-LTQ OrbiTrap MS方法；豌豆种皮多酚含量受品种影响[10] 挪威（Aslag）、法国（Assas）、捷克共和国（Dora）、德国（Golf、Poneka）、匈牙利（T Euro Orsz）、克罗地亚（MBK88、MBK90、MBK168和MBK173） 10种不同颜色的豌豆种皮 UHPLC-LTQ OrbiTrap MS 总酚含量（不同品种mg/g）：Aslaug（46.56±1.05）、Assas（41.80±0.20）、Dora（34.15±0.78）、Golf（23.13±0.97）、Poneka（39.02±0.72）、Törsz（18.84±0.31）、MBK88（15.94±0.78）、MBK90（2.78±0.53）、MBK168（45.75±2.09）、MBK173（36.64±1.11） 构建了豌豆籽粒中多酚的LTQ OrbiTrap MS定性定量方法；豌豆种皮多酚含量受品种和产区影响[11] 加拿大萨斯喀彻温大学作物发展中心鹰嘴豆、蚕豆、扁豆、豌豆和菜豆 5种豆科植物种皮 LC-MS 共98种；单体酚含量（µg/g）：山奈酚：基因型鹰嘴豆（30.33~89.21）、蚕豆（2.41~3.96）、扁豆（198.99~414.43）、豌豆（0.94~3.85）、菜豆（0.73~4071.40）、槲皮素：基因型鹰嘴豆（3.34~179.29）、蚕豆（3.43~5.36）、扁豆（0.17~7.23）、豌豆（0.29~9.87）、菜豆（4.01~225.71）、3，4-二羟基苯甲酸：基因型鹰嘴豆（0.32~0.59）、蚕豆（0.92~4.44）、扁豆（0.70~2.48）、豌豆（2.76~81.70）、菜豆（0.11~1.02）、香草酸-4-β-D-葡萄糖苷：基因型鹰嘴豆（1.58~4.44）、蚕豆（1.61~8.00）、扁豆（20.9~194.00）、豌豆（2.97~43.80）、菜豆（1.22~63.20） 构建了豆科植物种皮中98种多酚的LC-MS定性定量方法；豆科植物种皮多酚含量受基因型和产区影响[13] 德国霍尔茨豌豆冬季品种（James）豌豆夏季品种（Gregor、Navarro、Salamanca、Starter） 5种豌豆叶 HPLC-DAD-ESI-MS 单体酚含量（mg/g）：槲皮素：James（4.09）、Gregor（7.06）、Navarro（6.02）、Salamanca（6.16）、Starter（5.44）；山奈酚：James（0.93）、Gregor（1.11）、Navarro（1.88）、Salamanca（0.55）、Starter（1.28） 构建了豌豆叶片中多酚的HPLC-DAD-ESI-MS
定性定量方法；豌豆叶多酚含量受品种影响[17]注：鹰嘴豆（Cicer arietinum L.）；蚕豆（Vicia faba L.）；扁豆（Lens culinaris Medik.）；豌豆（Pisum sativum L.）；菜豆（Phaseolus vulgaris L.）；高效液相色谱（high performance liquid chromatography，HPLC）；超高效液相色谱-线性离子阱-静电场轨道阱组合式高分辨质谱（ultra performance liquid chromatography linear trap quadrupole orbitrap mass spectrometry，UHPLC-LTQ OrbiTrap MS）；半定量液相色谱质谱法（liquid chromatograph mass spectrometry，LC-MS）；高效液相色谱-二极管阵列检测器-电喷雾质谱（high performance liquid chromatography diode array detector electron spray ionization mass spectrometry，HPLC-DAD-ESI-MS）。
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表 3 豌豆中不同部位的提取溶剂、酚类物质含量以及抗氧化能力
Table 3. Extraction solvent, phenolic content and antioxidant capacity of different parts of pea
提取部位 最佳溶剂 酚类物质 含量（mg/g） 抗氧化方法 抗氧化能力（µmol/g） 黄豌豆籽粒[8] 丙酮/水（50:50，v/v） 总酚
总黄酮
缩合单宁0.94
0.13
0.39DPPH
FRAP
ORAC1.95
7.10
8.35绿豌豆籽粒[8] 丙酮/水（50:50，v/v） 总酚
总黄酮
缩合单宁0.81
0.12
0.42DPPH
FRAP
ORAC1.53
6.40
5.90豌豆籽粒[9] 丙酮/水/乙酸（70:29.5:0.5，v/v/v） 总酚
总黄酮0.27~1.95
0.53~5.08ABTS
FRAP3.04~22.27
1.24~18.87×103豌豆种皮[10] 甲醇/水/乙酸（80:19:1，v/v/v） 总酚 2.57~30.56 DPPH 0.72~2.55×103 豌豆种皮[11] 甲醇/水/乙酸（80:19:1，v/v/v） 总酚 2.78~46.56 DPPH 0.54~8.04×103 豌豆壳[15] 乙醇/水（80:20，v/v） 总酚 2.60 ORAC 23.06 黄豌豆籽粒[37] 丙酮/水（80:20，v/v） 总酚
总黄酮
缩合单宁1.34±0.02
0.32±0.02
1.52±0.04DPPH
FRAP
ORAC1.80±0.05
14.70±0.80
15.07±0.21绿豌豆籽粒[37] 丙酮/水（80:20，v/v） 总酚
总黄酮
缩合单宁1.07±0.01
0.39±0.02
1.71±0.04DPPH
FRAP
ORAC1.28±0.05
10.80±0.30
13.85±0.81豌豆籽粒[38] 甲醇/水（80:20，v/v） 总酚
单宁19.42
10.85ABTS 2547.90 黄豌豆籽粒[42] 乙醇/水（80:20，v/v） 总酚 2.50 ABTS 3.40 绿豌豆籽粒[42] 乙醇/水（80:20，v/v） 总酚 1.20 ABTS 1.80 豌豆籽粒[43] 甲醇/水（80:20，v/v） 总黄酮 1.35 TEAC
DPPH156.20
108.90注：物质含量均以干质量（mg/g）计；物质抗氧化能力以（µmol/g）计；1,1-二苯基-2-三硝基苯肼（2,2-diphenyl-1-picrylhydrazyl，DPPH）；2,2’-联氮-双-3-乙基苯并噻唑啉-6-磺酸（2,2’-azino-bis（3-ethylbenzothiazoline-6-sulfonic acid），ABTS）；氧自由基吸收能力（oxygen radical absorbance capacity，ORAC）；铁离子还原能力（ferricion reducing antioxidant power，FRAP）；奎诺二甲基丙烯酸酯等效抗氧化力（trolox equivalent antioxidant capacity，TEAC）。
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