梅花不同花色品种及开花阶段类黄酮代谢物测定与分析

doi:10.3864/j.issn.0578-1752.2023.09.012

Abstract

Abstract:

【Objective】Flower color is an extremely important ornamental trait of Prunus mume (P. mume), and flavonoids are the main pigments in the petals of P. mume. However, there are few systematic studies on the composition of flavonoids and the relationship between flower color and flavonoids in P. mume. The study on flavonoids can provide a reference for the mechanism of flower color formation and the development of flavonoids resources in P. mume.【Method】In this study, the petals of four P. mume cultivars with representative flower color in the blooming stage and the key period of flower color change of two cultivars were selected as materials. The flower color phenotype of petals was measured with the Royal Horticultural Society Color Card (RHSCC) and colorimeter. Flavonoids in those petals of flowers were determined by high-performance liquid chromatography and mass spectrometric (HPLC-MS) detectors. Then, Duncan test and OPLS-DA were used to analyze the difference of metabolites among these four cultivars and the major blooming stages. 【Result】In total, 25 flavonoids were determined in P. mume. The main components of red Baixu Zhusha and purple-red Huqiu Wanfen were anthocyanins. But the contents of cyanidin and its derivatives between Baixu Zhusha and Huqiu Wanfen were different. In addition, from the big budding stage to the blooming stage, the red color of Baixu Zhusha gradually became lighter, and the contents of cyanidin-3-O-glucoside and peonidin-3-O-glucoside also gradually decreased. Yellow-green Bian Lv’e and pure white Sanlun Yudie were most enriched with quercetin and its derivatives. The contents of quercetin derivatives between Bian Lv’e and Sanlun Yudie were different. 【Conclusion】The flavonoid metabolic profiles differed among the different colored petal of P. mume, and flavonoids with medicinal value were distributed in all varieties. The difference in the contents of cyanidin and peonidin might be related to petal color differences of red P. mume. Quercetin derivatives might affect the color of yellow-green P. mume. In this study, the flavonoids metabolites of different color P. mume were identified and analyzed for the first time, and the differences in flower color P. mume varieties and the blooming process were preliminarily understood from the metabolic level. The results provided a reference for understanding the difference of flower color formation and development of flavonoid resources of P. mume.

Key words: Prunus mume, flower color, flavonoids, HPLC-Q-TOF-MS

WU SiHui, ZHU HuanHuan, ZHANG JunWei, BAO ManZhu, ZHANG Jie. Determination and Analysis of Flavonoids Metabolites in Different Colors Cultivars and Blooming Stages of Prunus mume[J].Scientia Agricultura Sinica, 2023, 56(9): 1760-1774.

Figures/Tables 6

Fig. 1

Fig. 2

Table 1

Table 2

HPLC-ESI-MS analysis of main flavonoids in petals of four P. mume cultivars"

化合物名称 Compound name	正模式质荷比 [M+H]+(m/z)	正模式离子碎片质荷比 MS/MS (m/z)	保留时间 Rt (min)
矢车菊素3-O-葡萄糖苷 Cyanidin 3-O-glucoside	449.1071	10 ev: 287.0536	6.0
		20 ev: 287.0537
		30 ev: 287.0538
矢车菊素3-芸香糖苷 Cyanidin-3-rutinoside	595.1629	10 ev: 287.0551	6.2
		20 ev: 287.0549
		30 ev: 287.0550
矢车菊素3-芸香糖苷5-葡萄糖苷 Cyanidin 3-rutinoside 5-glucoside	757.2196	10 ev: 303.0409,755.2402	7.8
		20 ev: 303.0416,755.2425
		30 ev: 303.0430,755.2341
山奈素 Kaempferide; Kaempferol 4'-methyl ether	301.0524	30 ev: 72.0798,202.0611,286.0480	7.6
山奈酚-3-O葡萄糖苷 Kaempferol-3-O-glucoside	449.1071	10 ev: 287.0559	8.3
		20 ev: 287.0559
		30 ev: 287.0557
山奈酚 Kaempferol	287.0545	10 ev: 149.0202, 287.0547	5.3
		20 ev: 137.0215, 231.0650, 287.0544
		30 ev: 69.0002, 213.0538, 287.0542
山奈酚-3-O-芸香糖苷 Kaempferol-3-O-rutinoside	593.1539	30 ev: 285.0431	8.9
芍药花素-3-O-葡萄糖苷 Peonidin-3-O- glucoside	463.1195	10 ev: 301.0711	6.6
槲皮素 Quercetin	303.0499	10 ev: 153.01	8.5
槲皮素 Quercetin	303.0499	20 ev: 229.05, 153.01	8.5
槲皮素异构体 Quercetin isomer	303.0486	10 ev: 303.0434	7.8
		20 ev: 303.043, 301.0641, 286.0394
		30 ev: 303.0454, 258.0450
槲皮素-3,7-双葡萄糖苷 Quercetin-3,7-diglucoside	627.1858	10 ev: 151.0314, 319.0741, 481.1279, 625.3231	7.5
		20 ev: 151.0334, 319.0736, 463.1130, 625.3202
		30 ev: 71.0443, 151.0331, 303.0426, 437.1963, 648.3270
槲皮素-3-O-芸香糖苷 Quercetin-3-O-rutinoside	611.1534	10 ev: 94.1824, 301.0704, 463.1231, 609.1819	6.3
		20 ev: 205.3925, 301.0708, 463.1223, 609.1810
		30 ev: 141.9134, 301.0709, 463.1199, 609.1809
异鼠李素 Isorhamnetin; Quercetin 3'-methyl ether	317.0656	10 ev: 301.03, 285.03, 153.01	8.9
异鼠李素 Isorhamnetin; Quercetin 3'-methyl ether	317.0656	20 ev: 301.03, 153.01	8.9
槲皮素-3-芸香糖苷-5-葡萄糖苷 Quercetin-3-rutinoside 5-glucoside	757.2196	10 ev: 85.0219, 303.0416, 465.1002, 611.1565	7.8
		20 ev: 129.0483, 303.0445, 465.0944
		30 ev: 85.0244, 303.0469
槲皮素3-O-葡萄糖苷-7-O鼠李糖苷 Quercetin 3-O-glucoside-7-O-rhamnoside	611.1606	10 ev: 303.0483, 465.1007	8.3
槲皮素3-O-葡萄糖苷-7-O鼠李糖苷 Quercetin 3-O-glucoside-7-O-rhamnoside	611.1606	30 ev: 85.0625, 303.0484	8.3
槲皮素3-O-葡萄糖-2′-O-鼠李糖苷 Quercetin 3-O-glucosyl-2′-O-rhamnoside	611.1546	10 ev: 609.1796, 303.0475, 465.1001	7.8
		20eV: 463.1212, 303.0477
		30ev: 303.0678, 301.0678
槲皮素7-O-葡萄糖苷 Quercetin 7-O-glucoside	465.1087	10ev: 465.1363, 303.0662	14.5
		20ev: 303.0560
		30ev: 303.0497, 169.0475
槲皮素-3-O-半乳糖苷 Quercetin-3-O-galactoside	465.1025	10ev: 303.05, 85.02;	8.5
槲皮素-3-O-半乳糖苷 Quercetin-3-O-galactoside	465.1025	20ev: 303.05, 85.02	8.5
L-苯丙氨酸 L-Phenylalanine	166.0869	10ev: 120.0806	1.6
		20ev: 120.0806
		30ev: 103.0541
柚皮苷查尔酮 Naringenin chalcone	273.0756	10ev: 147.04;	11.0
柚皮苷查尔酮 Naringenin chalcone	273.0756	20ev: 147.04, 119.04	11.0
柚皮素 Naringenin	273.0759	10ev: 273.0750, 147.0436	13.2
		20ev: 147.0434, 67.0178
		30ev: 147.0427
表儿茶素 (-)-Epicatechin	291.0853	10ev: 139.0390, 207.0639	5.5
		20ev: 139.0386, 207.0621
		30ev: 139.0389, 207.0641
反式肉桂酸 Trans-Cinnamic acid	149.0247	10ev: 121.02;	18.3
反式肉桂酸 Trans-Cinnamic acid	149.0247	20ev: 65.03, 93.03	18.3
芹菜素 7-O-葡萄糖苷 Apigenin 7-O-glucoside	433.1135	10ev: 72.0768, 271.0599, 433.1102	6.1
		20ev: 82.6298, 202.0812, 271.0597，334.1545, 433.1174
		30ev: 70.0605, 213.1108, 271.0592, 381.7757
山奈酚-3-O-鼠李糖苷 Kaempferol-3-O-rhamnoside	609.1741	10ev: 145.4769, 301.0702, 463.1191, 609.1807	7.7
		20ev: 92.4395, 203.3603, 301.0692, 463.1283, 609.1791
		30ev: 186.6128, 301.0693, 411.0933, 514.2045, 609.1769

Table 2

Table 3

Contents of flavonoids in the four P. mume cultivars (μg·g-1 DW)"

化合物 Compound	变绿萼 BLE			白须朱砂 BXZS			虎丘晚粉 HQWF	三轮玉蝶 SLYD
化合物 Compound	S1	S2	S3	S1	S2	S3	S3	S3
矢车菊素及其衍生物 Cyanidin & der	23.19433±6.9111d	25.09807±6.8230d	24.49049±7.3049d	321.5764±29.0342a	269.4438±18.2802b	253.556±30.1520b	160.8748±31.0443c	13.17457±0.1746d
矢车菊素3-O-葡萄糖苷 Cyanidin 3-O-glucoside	0.249347±0.0548d	0.139457±0.0678d	0.274866±0.1378d	93.93701±12.6386a	74.49009±4.3347b	60.89043±6.2950b	46.79961±23.4663bc	0.521509±0.1627d
矢车菊素3-芸香糖苷 Cyanidin-3-rutinoside	0.642434±0.2695d	0.558807±0.1495d	0.910013±0.3881d	211.0013±15.3996a	179.0807±13.4858b	178.6813±22.4044b	96.79291±13.8961c	0.62395±0.1091d
矢车菊素3-芸香糖苷 5-葡萄糖苷 Cyanidin 3-rutinoside 5-glucoside	22.30255±6.5177ab	24.3998±6.6175a	23.30561±6.8268ab	16.63812±0.9968abc	15.87305±0.7590bc	13.98424±1.9486c	17.28227±3.0547abc	12.02911±0.6131c
山奈酚及其衍生物 Kaempferol & der	12.039843±3.536734c	16.111499±5.237862abc	21.224891±6.160233ab	22.048986±1.369479a	15.385608±0.495482bc	17.051458±2.376146abc	10.810202±3.056987c	1.908766±0.399028d
山奈素 Kaempferide; Kaempferol 4'-methyl ether	0.016243±0.0048d	0.009454±0.0056d	0.02076±0.0055d	1.855746±0.0448a	1.146767±0.0355b	1.052439±0.2283b	0.693246±0.3230c	0.173516±0.1425d
山奈酚-3-O-葡萄糖苷 Kaempferol-3-O-glucoside	0.015771±0.0070d	0.01793±0.0065d	0.012593±0.0076d	1.253472±0.2721a	0.708758±0.0147b	0.573263±0.0665b	0.315604±0.0796c	0.018661±0.0050d
山奈酚-3-O-鼠李糖苷 Kaempferol-3-O- rhamnoside	0.009559±0.004562d	0.019423±0.020323d	0.038939±0.030278d	0.987042±0.022245a	0.702135±0.118513b	0.487248±0.036127c	0.427012±0.077698c	0.036522±0.010289d
山奈酚-3-O-芸香苷 Kaempferol-3-O- rutinoside	11.89954±3.481270	15.97536±5.185996	21.04374±6.104958	11.07224±0.700547	7.56201±0.302161	10.45844±1.243375	6.361733±2.840426	1.613098±0.428618
山奈酚 Kaempferol	0.098726±0.0431e	0.089327±0.0345e	0.108864±0.0826e	6.88048±0.6611a	5.265938±0.1937b	4.480064±0.8063c	3.012608±0.4844d	0.066971±0.0427e
芍药花素-3-O-葡萄糖苷 Peonidin-3-O- glucoside	0.420124±0.2741d	0.366318±0.1059d	0.517428±0.1684d	63.40979±1.9240a	44.75599±2.0250c	41.2506±5.9861c	49.74721±1.4274b	2.352412±0.2994d
槲皮素及其衍生物 Quercetin & der	200.374354± 57.008561ab	242.845297± 74.146893a	222.257814± 65.306397ab	228.546233± 7.007537a	200.196038± 10.677757ab	170.253340± 13.654091ab	193.904286± 11.710335ab	141.676222± 25.143431b
槲皮素 Quercetin	42.20025±12.2538ab	58.65711±17.8150a	47.3339±13.6162ab	42.06114±2.0141ab	31.96046±7.9260b	30.28114±4.9902b	35.11689±6.5489b	30.17527±9.7758b
槲皮素异构体 Quercetin isomer	6.555547±1.8943b	7.493562±2.2430b	7.033184±2.0142b	7.453166±0.3934b	7.634126±0.2950b	7.077829±0.7544b	15.66637±0.9024a	6.985342±0.8417b
槲皮素-3,7-双葡萄糖苷 Quercetin-3,7- diglucoside	0.060759±0.041564c	0.251933±0.186512b	0.146210±0.067174bc	0.651130±0.016990a	0.629594±0.161718a	0.482118±0.144907a	0.053750±0.002803c	0.003918±0.002702c
槲皮素-3-O-芸香糖苷 Quercetin-3-O-rutinoside	0.212903±0.022909d	0.222162±0.097577d	0.356247±0.112679d	33.537172±1.631710a	23.542008±0.842671b	15.288866±3.932766c	16.317309±1.942946c	0.245465±0.009894d
异鼠李素 Isorhamnetin;Quercetin 3′-methyl ether	7.371176±2.2000b	8.068227±2.6434b	8.024497±2.2624b	15.14279±0.9453a	13.55353±0.3221a	10.07927±1.0379b	8.748217±1.1888b	15.68826±1.5345a
槲皮素-3-芸香糖苷-5- 葡萄糖苷 Quercetin-3-rutinoside 5- glucoside	22.30255a±6.5177b	24.3998±6.6175a	23.30561±6.8268ab	16.63812±0.9968abc	15.87305±0.7590bc	13.98424±1.9486c	17.28227±3.0547abc	12.02911±0.6131c
槲皮素3-O-葡萄糖苷- 7-O-鼠李糖苷 Quercetin 3-O-glucoside- 7-O-rhamnoside	64.97899±17.4415ab	72.9125±23.7989ab	73.97492±21.8967a	57.18113±5.5179abc	57.79963±2.5607abc	46.23906±12.2725bcd	36.60222±7.8126cd	26.77078±6.4454d
槲皮素3-O-葡萄糖- 2′-O-鼠李糖苷 Quercetin 3-O-glucosyl- 2′-O-rhamnoside	14.02704±4.0676abc	15.54876±4.6518ab	14.55381±4.3332abc	10.90494±0.3330bcd	9.897494±0.5319cd	9.431123±1.2302cd	16.62659±1.1178a	7.637097±2.2670d
槲皮素7-O-葡萄糖苷 Quercetin 7-O-glucoside	0.042835±0.0132ab ab	0.111345±0.1015a	0.042843±0.0156ab	0.054035±0.0176ab	0.033442±0.0079b	0.027085±0.0049b	0.021169±0.0035b	0.029225±0.0052b
槲皮素-3-O-半乳糖苷 Quercetin-3-O-galactoside	42.62231±12.8750	55.17989±16.5587	47.48659±14.2470	44.92262±2.1676	39.27272±1.6622	37.3626±4.6147	47.4695±9.0405	42.11175±4.0862
L-苯丙氨酸 L-Phenylalanine	24.77084±7.4279a	16.19404±5.3306b	17.89174±6.1028ab	9.427442±0.5934b	11.22424±0.7072b	11.53852±1.9330b	17.87086±2.0441ab	11.51065±4.6518b
柚皮苷查尔酮 Naringenin chalcone	11.21684±3.4274a	6.953229±2.4991bc	7.454445±2.1761b	7.338072±0.2187bc	4.580403±1.1159bc	5.911066±1.9611bc	0.279398±0.0346d	3.375202±2.6888cd
柚皮素 Naringenin	12.65308±4.7083ab	14.15428±5.8258a	9.227665±2.7799abc	7.578553±0.4136bc	6.651657±0.2251c	5.794245±0.9580c	0.549027±0.1002d	0.236822±0.0358d
表儿茶素 (-)-Epicatechin	2.025451±0.9418bc	1.727742±0.6128ab	2.010675±0.5011a	2.570646±0.2547bc	1.810294±0.1534bc	0.971233±0.3021bc	4.634156±1.3968bc	1.918482±0.3843bc
反式肉桂酸 Trans-Cinnamic acid	3.480043±1.2166bc	4.841706±1.8355bc	6.098765±1.6982bc	3.544063±0.3825b	2.527856±0.1313bc	2.87155±1.2722c	3.778505±0.5008a	2.775261±0.1719bc
芹菜素 7-O-葡萄糖苷 Apigenin 7-O-glucoside	0.062301±0.010509d	0.118913±0.050070d	0.171347±0.097035d	0.964745±0.102368a	0.635227±0.035925b	0.500521±0.051291bc	0.356049±0.250628c	0.044238±0.018730d

Table 3

Fig. 3

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品种 Cultivar	时期 Period	RHSCC	L*	a*	b*
变绿萼 Bian Lv’e	S1	Yellow group 4B	62.37±2.20c	-4.40±0.47f	16.59±0.79a
	S2	Yellow group 4D	67.35±3.14b	-2.33±0.65e	11.71±2.96b
	S3	Yellow group 4D	67.63±3.06b	-2.89±0.23ef	7.40±0.67c
白须朱砂 Baixu Zhusha	S1	Red group 53A	13.77±2.39g	36.64±1.83a	3.89±0.71d
	S2	Red group 53C	37.38±4.88e	33.62±1.79b	-3.71±0.66e
	S3	Red group 54A	26.67±4.30f	31.61±2.76c	-3.92±0.93e
虎丘晚粉 Huqiu Wanfen	S3	Red-purple group 62B	51.70±1.09d	20.48±0.60d	-5.96±0.10f
三轮玉蝶 Sanlun Yudie	S3	White group nn155C	74.86±1.51a	-3.04±0.31ef	7.25±0.54c

Determination and Analysis of Flavonoids Metabolites in Different Colors Cultivars and Blooming Stages of Prunus mume

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