Analysis of Folate Content and Its Derivatives in Grains of Wheat with Different Grain Colors

doi:10.13304/j.nykjdb.2024.0184

Abstract

Abstract:

Folic is essential for sustaining cell activity, promoting cell growth, and participating in cell division and proliferation. The demand for colored wheat is increasing due to its richness in anthocyanin, iron, zinc, selenium and other useful minerals. To research the content of folate in colored wheat grains，this study employed a total of 42 wheat varieties (lines) with varying grain colors as materials to ascertain the contents of 4 folic acid derivatives in 3 grains under 3 growing conditions: tetrahydrofolate (THF), 5-methyltetrahydrofolate (5-CH₃-THF), 5-formyltetrahydrofolate (5-CHO-THF) and 5,?10-methylenetetrahydrofolate (5,?10-CH⁺THF). The results indicated that the 4 folic acid derivatives were distributed across wheat varieties with varying grain colors, with a coefficient of variation ranging from 18.34% to 21.10%, among which Lin 4179 had high folic acid content, and with a total content of 66.99 μg·100 g^-1. The contents of 5-CH₃-THF and 5-CHO-THF accounted for approximately 70% of the total folic acid content. The mean total folate level in purple and blue grains was 62.31 and 62.97 μg·100 g^-1, respectively, which was significantly higher than that in white (41.90 μg·100 g^-1) and red grains (44.36 μg·100 g^-1). Genotype effect was the main factor affecting total folic acid content, environmental factors have less impact. The results of this study provided an important insight for the development and breeding of folate biofortified wheat varieties.

Key words: wheat, grain color, folates, derivatives

摘要：

叶酸在促进细胞生长、维持细胞活性、参与细胞增殖和分裂过程中起关键作用。彩色小麦富含花青素、铁、锌、硒等功能营养物质，人们对彩色小麦需求越来越大，为研究彩色小麦籽粒叶酸及衍生物的含量，以42份不同粒色的小麦品种（系）为材料，利用高效液相色谱法测定了3个生长条件籽粒中四氢叶酸（tetrahydrofolate，THF）、5-甲基四氢叶酸（5-CH₃-THF）、5-甲酰基四氢叶酸（5-CHO-THF）和5，10-亚甲基四氢叶酸（5， 10-CH⁺THF） 4种叶酸衍生物的含量。结果表明，4种叶酸衍生物在不同粒色的小麦中均有分布，总叶酸含量变异范围较广，变异系数为18.34%~21.10%，其中临4179总含量为66.99 μg·100g^-1，为高叶酸含量品种。5-CH₃-THF和5-CHO-THF含量约为总叶酸含量的70%，且与总叶酸含量显著相关；紫粒和蓝粒品种的总叶酸平均含量分别为62.31和62.97 μg·100 g^-1，显著高于白粒（41.90 μg·100 g^-1）和红粒品种（44.36 μg·100 g^-1）；基因型效应是影响总叶酸含量的主要因素，环境因素的影响较小。研究结果为小麦叶酸生物强化品种的选育和栽培提供了有价值的信息。

关键词: 小麦, 粒色, 叶酸, 衍生物

CLC Number:

S512

Peng TIAN, Jie SONG, Xia LI, Yuzhi WANG, Bangbang WU. Analysis of Folate Content and Its Derivatives in Grains of Wheat with Different Grain Colors[J]. Journal of Agricultural Science and Technology, 2024, 26(11): 56-65.

田鹏, 宋洁, 李霞, 王裕智, 武棒棒. 不同粒色小麦籽粒中叶酸及衍生物含量分析[J]. 中国农业科技导报, 2024, 26(11): 56-65.

Figures/Tables 8

References 34

1	EDELMANN M, KARILUOTO S, NYSTRÖM L, et al.. Folate in oats and its milling fractions [J]. Food Chem., 2012, 135(3):1938-1947.
2	张婷,李光辉.妊娠期母体叶酸水平与母儿结局的研究进展[J].中国全科医学, 2019, 22(3): 253-257, 262.
	ZHANG T, LI G H. Research progress on maternal folic acid level and pregnancy outcomes [J]. Chin. Gen. Practice, 2019, 22(3): 253-257, 262.
3	FIELD M S, KAMYNINA E, CHON J, et al.. Nuclear folate metabolism [J]. Annu. Rev. Nutr., 2018, 38: 219-243.
4	CZEIZEL A E, DUDÁS I, VERECZKEY A, et al.. Folate deficiency and folic acid supplementation: the prevention of neural-tube defects and congenital heart defects [J]. Nutrients, 2013, 5(11): 4760-4775.
5	RADER J I, SCHNEEMAN B O. Prevalence of neural tube defects, folate status, and folate fortification of enriched cereal-grain products in the United States [J]. Pediatrics, 2006, 117(4): 1394-1399.
6	BHUTTA Z A, SALAM R A. Global nutrition epidemiology and trends [J]. Ann. Nutr. Metab., 2012, 61(S1): 19-27.
7	JHA A B, ASHOKKUMAR K, DIAPARI M, et al.. Genetic diversity of folate profiles in seeds of common bean, lentil, chickpea and pea [J]. J. Food Compos. Anal., 2015, 42: 134-140.
8	REBEILLE F, RAVANEL S, JABRIN S, et al.. Folates in plants: biosynthesis, distribution, and enhancement [J]. Physiol. Plant, 2006, 126(3): 330-342.
9	BLANCQUAERT D, VAN D J, STROBBE S, et al.. Improving folate (vitamin B9) stability in biofortified rice through metabolic engineering [J]. Nat. Biotechnol., 2015, 33(10): 1076-1078.
10	KHALILI M, RAD A H, KHOSROUSHAHI A Y, et al.. Application of probiotics in folate bio-fortification of yoghurt [J]. Probiotics Antimicrob. Proteins, 2020, 12(2): 756-763.
11	CRIDER K S, YANG T P, BERRY R J, et al.. Folate and DNA methylation: a review of molecular mechanisms and the evidence for folate’s role [J]. Adv. Nutr., 2012, 3(1): 21-38.
12	RAKSZEGI M, BOROS D, KUTI C, et al.. Compositionand end-use quality of 150 wheat lines selected for the HEALTHGRAIN diversityscreen [J]. J. Agric. Food Chem., 2008, 56(21): 9750-9757.
13	CAO X Y, XU J F, LIN Y L, et al.. Excess folic acid intake increases DNA de novo point mutations [J/OL]. Cell Discov., 2023, 9(1): 22 [2024-05-20]. .
14	BOTTO L D, LISI A, ROBERT-GNANSIA E, et al.. International retrospective cohort study of neural tube defects in relation to folic acid recommendations: are the recommendations working? [J/OL] BMJ, 2005, 330(7491): 571 [2024-05-23]. .
15	RIAZ B, LIANG Q J, WAN X, et al.. Folate content analysis of wheat cultivars developed in the North China Plain [J]. Food Chem., 2019, 289:377-383.
16	ZHENG J, WANG X S, WU B B, et al.. Folate (vitamin B9) content analysis in bread wheat (Triticum aestivum L.) [J/OL]. Front. Nutr., 2022, 9:933358 [2024-05-20]. .
17	STROBBE S, VAN D S D. Folate biofortification in food crops [J]. Curr. Opin. Biotechnol., 2017, 44: 202-211.
18	GUO Z F, ZHANG Z B, XU P, et al.. Analysis of nutrient compositions of purple wheats [J]. Cereal Res. Commun., 2013, 41(2): 293-303.
19	张小燕,高遒竹,高向阳.特殊粒色小麦研究进展[J].粮油食品科技, 2016, 24(4): 7-11.
	ZHAO X Y, GAO Q Z, GAO X Y. Research progress on special color wheat [J]. Sci. Technol. Cereals, Oils Foods, 2016, 24(4): 7-11.
20	DAVIS K R, PETERS L J, LETOURNEAU D. Variability of the vitamin content in wheat [J]. Cereal Food World, 1984, 29: 364-370.
21	PIIRONEN V, EDELMANN M, KARILUOTO S, et al.. Folate in wheat genotypes in the HEALTHGRAIN Diversity Screen [J]. J. Agric. Food Chem., 2008, 56(21): 9726-9731.
22	ARCOT J, WOOTTON M, ALURY S, et al.. Folate levels in twelve Australian wheats and changes during processing into bread [J]. Food Aust., 2002, 54(1,2): 18-20.
23	郭健,李敏,孟妍,等.荧光分光光度法测定食品中叶酸的含量[J].中国公共卫生, 2003, 19(10): 111.
24	PANDRANGI S, LABORDE L F. Optimization of microbiological assay of folic acid and determination of folate content in spinach [J]. Int. J. Food Sci. Technol., 2004, 39(5): 525-532.
25	常娜宁,姜凌,蒲训,等.作物叶酸检测方法的研究进展[J].中国农业科技导报, 2010, 12(2): 44-49.
	CHANG N N, JIANG L, PU X, et al.. Research progress on methodology for folate detection in crops [J]. J. Agric. Sci. Technol., 2010, 12(2): 44-49.
26	苏文斌. Fenton试剂氧化-荧光分析法测定果蔬中叶酸的含量[J].食品科学, 2011, 32(4): 212-215.
	SU W B. Fluorimetric determination of folic acid in vegetable samples using Fenton reagent as oxidant [J]. Food Sci., 2011, 32(4): 212-215.
27	吴姝,陈思,胡琪,等.光催化氧化荧光衍生法检测叶酸[J].分析科学学报, 2022, 38(1): 1-5.
	WU S, CHENG S, HU Q, et al.. Determination of folic acid based on Photo-catalytic oxidation fluorescence derivatization [J]. J. Anal. Sci., 2022,38(1): 1-5.
28	ELŻBIETA G, ANDRZEJ K. Determination of folate in some cereals and commercial cereal-grain products consumed in Poland using trienzyme extraction and high-performance liquid chromatography methods [J]. Eur. Food Res. Technol., 2005, 221: 208-213.
29	ZHANG G F, STOROZHENKO S, VAN DER STRAETEN D, et al.. Investigation of the extraction behavior of the main monoglutamate folates from spinach by liquid chromatography-electrospray ionization tandem mass spectrometry [J]. J. Chromatogr. A, 2005, 1078(1,2): 59-66.
30	PÓO-PRIETO R, HAYTOWITZ D B, HOLDEN J M, et al.. Use of the affinity/HPLC method for quantitative estimation of folic acid in enriched cereal-grain products [J]. J. Nutr., 2006, 136(12): 3079-3083.
31	PFEIFFER C M, ROGERS L M, GREGORY J F. Determination of folate in cereal-grain food products using trienzyme extraction and combined affinity and reversedphase liquid chromatography [J]. J. Agric. Food Chem., 1997, 45(2): 407-413.
32	UPADHYAYA P, TYAGI K, SARMA S, et al.. Natural variation in folate levels among tomato (Solanum lycopersicum) accessions [J]. Food Chem., 2017, 217: 610-619.
33	李杏普,兰素缺,刘玉平.蓝、紫粒小麦籽粒色素及其相关生理生化特性的研究[J].作物学报, 2003,29(1):157-158.
	LI X P, LAN S Q, LIU Y P. Studies on pigment and It’s related physio-biochemical properties of blue or purple grain wheat [J]. Acta Agronomica Sinica, 2003, 29(1): 157-158.
34	SHEWRY P R, PIIRONEN V, LAMPI A M, et al.. Effects of genotype and environment on the content and composition of phytochemicals and dietary fiber components in rye in the HEALTHGRAIN diversity screen [J]. J. Agric. Food Chem., 2010, 58(17): 9372-9383.

材料 Material	叶酸衍生物 Derivatives	样品含量 Sample content/（μg·100 g^-1）	加标量 Added/（μg·100 g^-1）	检测含量 Detection/（μg·100 g^-1）	回收率 Recovery rate/%
临6308 Lin 6308	THF	3.84	6	9.41	95.63
	5-CH₃-THF	10.14	20	29.54	98.01
	5-CHO-THF	13.98	20	33.59	98.85
	5， 10-CH⁺THF	4.54	8	12.15	96.89
晋麦47 Jinmai 47	THF	3.95	6	9.48	95.28
	5-CH₃-THF	10.23	20	29.12	97.33
	5-CHO-THF	16.11	20	34.55	95.68
	5， 10-CH⁺THF	5.32	8	12.88	96.70

材料 Material	叶酸衍生物 Derivatives	样品含量 Sample content/（μg·100 g^-1）	加标量 Added/（μg·100 g^-1）	检测含量 Detection/（μg·100 g^-1）	回收率 Recovery rate/%
临6308 Lin 6308	THF	3.84	6	9.41	95.63
	5-CH₃-THF	10.14	20	29.54	98.01
	5-CHO-THF	13.98	20	33.59	98.85
	5， 10-CH⁺THF	4.54	8	12.15	96.89
晋麦47 Jinmai 47	THF	3.95	6	9.48	95.28
	5-CH₃-THF	10.23	20	29.12	97.33
	5-CHO-THF	16.11	20	34.55	95.68
	5， 10-CH⁺THF	5.32	8	12.88	96.70

材料 Material	叶酸衍生物 Derivatives	样品含量 Sample content/ （μg·100 g^-1）					均值 Average/（μg·100 g^-1）	相对标准偏差 RSD/%
材料 Material	叶酸衍生物 Derivatives	1	2	3	4	5	均值 Average/（μg·100 g^-1）	相对标准偏差 RSD/%
临6308 Lin 6308	THF	3.87	3.59	3.78	3.91	3.59	3.75	3.62
	5-CH₃-THF	10.37	10.62	9.97	10.29	10.74	10.40	2.59
	5-CHO-THF	13.87	15.45	14.26	14.47	14.88	14.59	3.71
	5，10-CH⁺THF	4.68	4.46	4.23	4.34	4.22	4.39	3.89

材料 Material	叶酸衍生物 Derivatives	样品含量 Sample content/ （μg·100 g^-1）					均值 Average/（μg·100 g^-1）	相对标准偏差 RSD/%
材料 Material	叶酸衍生物 Derivatives	1	2	3	4	5	均值 Average/（μg·100 g^-1）	相对标准偏差 RSD/%
临6308 Lin 6308	THF	3.87	3.59	3.78	3.91	3.59	3.75	3.62
	5-CH₃-THF	10.37	10.62	9.97	10.29	10.74	10.40	2.59
	5-CHO-THF	13.87	15.45	14.26	14.47	14.88	14.59	3.71
	5，10-CH⁺THF	4.68	4.46	4.23	4.34	4.22	4.39	3.89

序号 Code	材料 Material	粒色 Grain color	THF/ （μg·100 g^-1）	5-CH₃-THF/（μg·100 g^-1）	5-CHO-THF/（μg·100 g^-1）	5， 10-CH⁺THF/（μg·100 g^-1）	总量Total/（μg·100 g^-1）
1	临5269 Lin 5269	白White	4.81±0.22	14.15±0.98	12.87±0.93	4.93±0.38	36.76±2.50
2	太麦227 Taimai 227	白White	4.04±0.31	10.61±0.85	17.05±0.54	3.76±0.15	35.46±1.85
3	临4133 Lin 4133	白White	7.97±0.17	14.07±0.37	18.40±1.19	4.11±0.18	44.55±1.91
4	尧麦33 Yaomai 33	白White	4.40±0.29	15.79±0.34	14.48±1.17	6.76±0.32	41.43±2.12
5	运麦33 Yunmai 33	白White	2.80±0.39	15.52±0.82	21.27±0.74	4.52±0.12	44.11±2.07
6	临优39 Linyou 39	白White	2.71±0.14	14.50±0.35	20.87±0.91	3.91±0.32	41.99±1.72
7	临6080 Lin 6080	白White	3.89±0.11	30.51±0.90	20.05±0.68	4.13±0.11	58.58±1.80
8	运优1号Yunyou 1	白White	6.28±0.25	17.15±0.36	19.87±1.02	3.79±0.25	47.09±1.88
9	运旱161 Yunhan 161	白White	5.03±0.23	15.29±0.73	14.99±1.20	6.19±0.35	41.50±2.51
10	良星99 Liangxin 99	白White	6.45±0.23	17.20±0.62	14.03±0.82	3.77±0.29	41.45±1.95
11	临旱19 Linhan 19	白White	4.47±0.22	12.05±0.47	16.63±1.15	4.68±0.25	37.83±2.08
12	并麦3281 Bingmai 3281	白White	5.15±0.32	15.57±0.46	12.10±0.93	4.81±0.40	37.63±2.11
13	沃麦379 Womai 379	白White	4.90±0.11	12.51±0.94	14.48±0.64	4.42±0.33	36.31±2.02
14	农大164 Nongda 164	红Red	2.88±0.21	19.08±0.66	21.24±1.22	4.86±0.16	48.06±2.25
15	太麦4672 Taimai 4672	红Red	5.24±0.10	19.16±0.82	21.02±1.01	4.23±0.36	49.65±2.29
16	临5133 Lin 5133	红Red	4.90±0.14	17.06±0.89	18.14±0.97	4.39±0.36	44.49±2.36
17	圣麦35 Shengmai 35	红Red	5.14±0.33	14.35±0.81	14.83±0.79	4.85±0.13	39.17±2.06
18	太麦364 Taimai 364	红Red	3.96±0.19	15.49±1.02	14.50±0.64	4.47±0.35	38.42±2.20
19	并麦471 Bingmai 471	红Red	7.60±0.19	17.72±0.61	14.84±0.75	4.47±0.23	44.63±1.78
20	并麦236 Bingmai 236	红Red	6.92±0.17	16.82±0.78	14.51±0.98	4.82±0.29	43.07±2.22
21	云麦7454 Yunmai 7454	红Red	1.48±0.16	17.58±0.64	18.04±0.74	4.41±0.27	41.51±1.81
22	连麦39 Lianmai 39	红Red	4.68±0.20	20.86±0.67	16.55±0.56	4.73±0.20	46.82±1.63
23	晋太181 Jintai 181	红Red	3.45±0.25	21.79±1.07	17.86±0.79	4.72±0.36	47.82±2.47
24	济蓝71 Jilan 71	蓝Blue	4.73±0.32	20.98±0.77	28.94±1.89	6.41±0.30	61.06±3.28
25	宁春23号Ningchun 23	蓝Blue	4.87±0.32	20.55±1.19	31.25±1.74	4.62±0.12	61.29±3.37
26	中蓝48 Zhonglan 48	蓝Blue	2.75±0.35	25.09±0.98	30.37±1.00	4.60±0.15	62.81±2.48
27	蓝麦1427 Lanmai 1427	蓝Blue	5.26±0.18	28.77±0.76	28.31±1.45	4.57±0.24	66.91±2.63
28	曲麦58 Qumai 58	蓝Blue	4.30±0.25	22.43±1.17	31.31±1.11	4.50±0.21	62.54±2.74
29	永蓝584 Yonglai 584	蓝Blue	5.82±0.32	24.39±0.89	28.22±2.09	5.20±0.14	63.63±3.43
30	中鼎17 Zhongding 17	蓝Blue	4.15±0.21	22.24±1.19	31.09±1.90	5.17±0.28	62.65±3.57
31	运紫糯1号Yunzinuo 1	紫Purple	6.06±0.21	23.92±3.20	22.85±1.22	4.24±0.28	57.07±2.11
32	紫优5号Ziyou 5	紫Purple	7.72±0.12	23.12±0.60	24.84±1.45	3.74±0.12	59.42±2.29
33	紫优11 Ziyou 11	紫Purple	5.23±0.15	23.33±0.98	30.87±1.64	4.37±0.18	63.80±2.95
34	运紫827 Yunzi 827	紫Purple	5.46±0.26	25.46±1.09	25.77±1.97	6.34±0.16	63.03±1.95
35	临1546 Lin 1546	紫Purple	5.29±0.22	25.01±0.74	26.59±1.88	4.61±0.16	61.50±2.99
36	临4179 Lin 4179	紫Purple	4.10±0.27	20.40±1.70	36.33±2.32	6.17±1.38	66.99±0.68
37	临1547 Lin 1547	紫Purple	5.39±0.22	27.50±0.72	26.27±1.85	4.56±0.17	63.72±2.95
38	太紫372 Taizi 372	紫Purple	5.39±0.18	21.87±0.70	34.20±4.91	4.29±0.23	65.75±5.49
39	中黑麦31 Zhongheimai 31	紫Purple	4.68±0.37	22.81±2.13	27.70±1.72	4.14±0.27	59.33±1.65
40	运黑66 Yunhei 66	紫Purple	3.98±0.27	23.91±0.66	28.34±1.29	5.25±0.19	61.48±2.40
41	太紫36 Taizi 36	紫Purple	2.00±0.36	27.09±0.62	27.32±1.92	5.60±0.11	62.01±3.01
42	太紫432 Taizi 432	紫Purple	2.36±0.27	24.24±0.68	29.79±1.62	4.05±0.12	60.44±2.68