铁皮石斛的黄酮类成分测定及其生物可及性研究

doi:10.3969/j.issn.1004-1524.20221517

浙江农业学报 ›› 2023, Vol. 35 ›› Issue (11): 2710-2719.DOI: 10.3969/j.issn.1004-1524.20221517

铁皮石斛的黄酮类成分测定及其生物可及性研究

孙凤婷¹^,²(), 许振岚², 朱作艺², 张春荣², 汤涛², 赵学平², 盛清¹^,^*(), 王强²^,^*()

1.浙江理工大学生命科学与医药学院,浙江杭州 310018
2.农业农村部农药残留检测重点实验室,浙江省农业科学院农产品质量安全与营养研究所,浙江杭州 310021

收稿日期:2022-10-26 出版日期:2023-11-25 发布日期:2023-12-04
作者简介:孙凤婷(1998—),女,山东临沂人,硕士研究生,研究方向为农产品质量安全与营养。E-mail: 17805452209@163.com
通讯作者: * 盛清,E-mail: csheng866@126.com;王强,E-mail: wq13575733860@126.com
基金资助:
国家自然科学基金(21806143)

Determination of flavonoids in Dendrobium officinale Kimura et Migo and study on its bioavailability

SUN Fengting¹^,²(), XU Zhenlan², ZHU Zuoyi², ZHANG Chunrong², TANG Tao², ZHAO Xueping², SHENG Qing¹^,^*(), WANG Qiang²^,^*()

1. College of Life Sciences and Medicine, Zhejiang Sci-Tech University, Hangzhou 310018, China
2. Key Laboratory for Pesticide Residue Detection, Ministry of Agriculture and Rural Affairs, Institute of Agro-Product Safety and Nutrition, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, China

Received:2022-10-26 Online:2023-11-25 Published:2023-12-04

摘要/Abstract

摘要：

为探究铁皮石斛中黄酮类化合物的含量及其生物可及性,建立固相萃取-超高效液相色谱串联质谱法测定17个黄酮单体的含量,并采用体外模拟消化法分析铁皮石斛在消化过程中黄酮类化合物的生物可及性。结果表明,铁皮石斛中总黄酮含量为1.52~4.36 mg·g^-1,柚皮素、芦丁和夏佛塔苷是其中含量较高的3种黄酮单体。模拟胃-小肠消化后,总黄酮的生物可及性为13.75%~21.45%,柚皮素、芦丁和夏佛塔苷的生物可及性分别为8.23%~18.37%、1.85%~22.87%和24.26%~42.65%;进一步结肠消化后,总黄酮的生物可及性为6.38%~14.13%,柚皮素、芦丁和夏佛塔苷的生物可及性分别为2.12%~5.67%、1.42%~5.70%和5.34%~13.33%,黄酮类化合物在胃-小肠中的生物可及性大于结肠。铁皮石斛75%乙腈提取液的抗氧化能力>胃-小肠消化液的抗氧化能力>结肠消化液的抗氧化能力,且抗氧化能力与黄酮类化合物的含量呈显著正相关。

关键词: 铁皮石斛, 黄酮, 生物可及性, 抗氧化活性

Abstract:

A solid phase extraction-ultra performance liquid chromatography tandem mass spectrometry method was established to determine 17 flavonoid components in D. officinale. And meanwhile the in vitro method was used to simulate the digestive process and to analyze the bioavailability of flavonoids in D. officinale. The results showed that the total content of flavonoids in D. officinale was 1.52-4.36 mg·g^-1. Naringenin, rutin and schaftoside were the three main flavonoid compounds in D. officinale. After gastrointestinal digestion, the bioavailability of total flavonoids was 13.75%-21.45%, and the bioavailability of naringin, rutin and schaftoside were 8.23%-18.37%, 1.85%-22.87% and 24.26%-42.65%, respectively. After further colonic digestion, the bioavailability of total flavonoids was 6.38%-14.13%, and the bioavailability of naringin, rutin and schaftoside were 2.12%-5.67%, 1.42%-5.70% and 5.34%-13.33%, respectively. The bioavailability of flavonoids in the gastrointestinal tract was greater than that in the colon phase. The antioxidant capacity followed D. officinale extract>gastrointestinal digestive juice>colon digestive juice, and the antioxidant capacity was positively correlated with the content of flavonoids.

Key words: Dendrobium officinale Kimura et Migo, flavonoids, bioavailability, antioxidant activity

中图分类号:

S567.239

孙凤婷, 许振岚, 朱作艺, 张春荣, 汤涛, 赵学平, 盛清, 王强. 铁皮石斛的黄酮类成分测定及其生物可及性研究[J]. 浙江农业学报, 2023, 35(11): 2710-2719.

SUN Fengting, XU Zhenlan, ZHU Zuoyi, ZHANG Chunrong, TANG Tao, ZHAO Xueping, SHENG Qing, WANG Qiang. Determination of flavonoids in Dendrobium officinale Kimura et Migo and study on its bioavailability[J]. Acta Agriculturae Zhejiangensis, 2023, 35(11): 2710-2719.

图/表 9

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编号 Number	产地 Origin	样品类型 Sample type
TP1	安徽霍山 Anhui Huoshan	鲜茎 Fresh stem
TP2	云南德宏 Yunnan Dehong	鲜茎 Fresh stem
TP3	广西巴马 Guangxi Bama	鲜茎 Fresh stem
TP4	福建漳州 Fujian Zhangzhou	鲜茎 Fresh stem
TP5	贵州赤水 Guizhou Chishui	鲜茎 Fresh stem
TP6	云南玉溪 Yunnan Yuxi	干茎 Dry stem
TP7	云南文山 Yunnan Wenshan	干茎 Dry stem
TP8	云南德宏 Yunnan Dehong	干茎 Dry stem
TP9	云南德宏 Yunnan Dehong	枫斗 Fengdou
TP10	浙江乐清 Zhejiang Yueqing	干茎 Dry stem

编号 Number	产地 Origin	样品类型 Sample type
TP1	安徽霍山 Anhui Huoshan	鲜茎 Fresh stem
TP2	云南德宏 Yunnan Dehong	鲜茎 Fresh stem
TP3	广西巴马 Guangxi Bama	鲜茎 Fresh stem
TP4	福建漳州 Fujian Zhangzhou	鲜茎 Fresh stem
TP5	贵州赤水 Guizhou Chishui	鲜茎 Fresh stem
TP6	云南玉溪 Yunnan Yuxi	干茎 Dry stem
TP7	云南文山 Yunnan Wenshan	干茎 Dry stem
TP8	云南德宏 Yunnan Dehong	干茎 Dry stem
TP9	云南德宏 Yunnan Dehong	枫斗 Fengdou
TP10	浙江乐清 Zhejiang Yueqing	干茎 Dry stem

消化道模型 Alimentary canal model	组成成分 Components	含量 Content
胃(pH 2.5)	苹果酸钠 Sodium malate	0.5 g·L^-1
Stomach (pH 2.5)	柠檬酸钠 Tri-sodium citrate	0.5 g·L^-1
	乳酸 Lactic acid	420 μL·L^-1
	冰醋酸 Glacial acetic acid	500 μL·L^-1
	胃蛋白酶 Pepsin	1.25 g·L^-1
小肠(添加到胃液中, pH 7.0)	胆盐 Bile salts	1.78 g·L^-1
Small intestine (add to stomach medium, pH 7.0)	胰蛋白酶 Pancreatin	0.5 g·L^-1
结肠(pH 6.5)	Ⅱ型黏蛋白 Type Ⅱ mucin (from porcine stomach)	4 g·L^-1
Colon (pH 6.5)	氯化钠 Sodium chloride	4.5 g·L^-1
	氯化钾 Potassium chloride	4.5 g·L^-1
	碳酸氢钠 Sodium bicarbonate	1.5 g·L^-1
	六水合硫酸镁 Magnesium sulphate hexahydrate	1.25 g·L^-1
	盐酸半胱氨酸 Cysteine hydrochloride	800 mg·L^-1
	磷酸钾 Potassium phosphate	500 mg·L^-1
	磷酸氢二钾 Di-potassium phosphate	500 mg·L^-1
	胆盐 Bile salts	400 mg·L^-1
	氯化钙 Calcium chloride	189 mg·L^-1
	血红素 Hemin	50 mg·L^-1
	七水合硫酸亚铁 Iron (Ⅱ) sulphate heptahydrate	5 mg·L^-1

消化道模型 Alimentary canal model	组成成分 Components	含量 Content
胃(pH 2.5)	苹果酸钠 Sodium malate	0.5 g·L^-1
Stomach (pH 2.5)	柠檬酸钠 Tri-sodium citrate	0.5 g·L^-1
	乳酸 Lactic acid	420 μL·L^-1
	冰醋酸 Glacial acetic acid	500 μL·L^-1
	胃蛋白酶 Pepsin	1.25 g·L^-1
小肠(添加到胃液中, pH 7.0)	胆盐 Bile salts	1.78 g·L^-1
Small intestine (add to stomach medium, pH 7.0)	胰蛋白酶 Pancreatin	0.5 g·L^-1
结肠(pH 6.5)	Ⅱ型黏蛋白 Type Ⅱ mucin (from porcine stomach)	4 g·L^-1
Colon (pH 6.5)	氯化钠 Sodium chloride	4.5 g·L^-1
	氯化钾 Potassium chloride	4.5 g·L^-1
	碳酸氢钠 Sodium bicarbonate	1.5 g·L^-1
	六水合硫酸镁 Magnesium sulphate hexahydrate	1.25 g·L^-1
	盐酸半胱氨酸 Cysteine hydrochloride	800 mg·L^-1
	磷酸钾 Potassium phosphate	500 mg·L^-1
	磷酸氢二钾 Di-potassium phosphate	500 mg·L^-1
	胆盐 Bile salts	400 mg·L^-1
	氯化钙 Calcium chloride	189 mg·L^-1
	血红素 Hemin	50 mg·L^-1
	七水合硫酸亚铁 Iron (Ⅱ) sulphate heptahydrate	5 mg·L^-1

黄酮Flavonoids	TP1	TP2	TP3	TP4	TP5	TP6	TP7	TP8	TP9	TP10
柚皮素 Naringenin	16.09 ±0.86	14.42 ±0.45	15.23 ±0.71	14.53 ±0.33	11.97 ±0.43	27.31 ±1.69	37.89 ±2.61	33.72 ±1.32	25.82 ±2.02	23.58 ±1.63
槲皮素 Quercetin	0.71 ±0.03	0.97 ±0.01	1.50 ±0.11	0.81 ±0.04	0.77 ±0.01	0.75 ±0.03	0.70 ±0.01	0.66 ±0.03	0.77 ±0.02	0.59 ±0.02
芦丁 Rutin	75.16 ±0.99	195.54 ±4.45	110.61 ±5.74	115.84 ±8.45	201.08 ±2.84	62.57 ±3.41	9.87 ±1.83	44.93 ±3.81	25.57 ±4.2	41.62 ±3.71
异鼠李素 Isorhamnetin	0.11 ±0.03	0.14 ±0.03	0.24 ±0.03	0.12 ±0.02	0.13 ±0.02	0.09 ±0.02	0.07 ±0.01	0.08 ±0.01	0.08 ±0.01	0.07 ±0.01
芹菜素 Apigenin	0.15 ±0.03	0.17 ±0.01	0.35 ±0.03	0.16 ±0.01	0.13 ±0.02	0.09 ±0.03	0.10 ±0.03	0.10 ±0.03	0.31 ±0.01	0.07 ±0.01
圣草酚 Eriodictyol	0.48 ±0.04	0.83 ±0.12	2.65 ±0.22	0.83 ±0.13	0.75 ±0.04	0.49 ±0.06	0.43 ±0.09	0.20 ±0.08	0.10 ±0.01	0.13 ±0.06
金圣草黄素 Chrysoeriol	0.24 ±0.01	0.21 ±0.01	0.18 ±0.03	0.17 ±0.03	0.25 ±0.02	0.08 ±0.01	0.10 ±0.03	0.06 ±0.01	0.36 ±0.02	0.07 ±0.01
橙皮素 Hesperetin	0.23 ±0.01	0.25 ±0.03	0.32 ±0.01	0.17 ±0.01	0.18 ±0.02	0.17 ±0.03	0.16 ±0.03	0.13 ±0.02	0.19 ±0.03	0.09 ±0.01
异槲皮苷 Isoquercitrin	0.37 ±0.01	0.43 ±0.01	0.25 ±0.02	0.35 ±0.02	0.51 ±0.02	0.31 ±0.06	0.10 ±0.01	0.47 ±0.05	0.28 ±0.04	0.21 ±0.04
槲皮苷 Quercitrin	0.14 ±0.02	0.25 ±0.02	0.11 ±0.01	0.28 ±0.03	0.23 ±0.02	0.05 ±0.01	0.05 ±0.01	0.08 ±0.01	0.05 ±0.01	0.07 ±0.01
木犀草苷 Luteoloside	0.22 ±0.01	0.20 ±0.02	0.33 ±0.03	0.12 ±0.04	0.17 ±0.01	0.09 ±0.02	0.05 ±0.01	0.04 ±0.01	0.25 ±0.09	0.05 ±0.01
山柰酚 Kaempferol	0.14 ±0.04	0.20 ±0.01	0.29 ±0.07	0.15 ±0.03	0.22 ±0.04	0.07 ±0.01	0.07 ±0.02	0.08 ±0.02	0.29 ±0.10	0.06 ±0.02
夏佛塔苷 Schaftoside	56.70 ±3.01	40.02 ±6.84	58.20 ±3.29	278.23 ±25.54	79.55 ±2.20	11.49 ±1.46	11.94 ±1.68	21.82 ±1.23	33.88 ±0.91	7.06 ±0.30
芹菜苷 Apiin	0.84 ±0.03	0.56 ±0.02	0.62 ±0.11	0.30 ±0.02	0.53 ±0.01	0.26 ±0.07	0.36 ±0.02	0.27 ±0.08	0.25 ±0.07	0.50 ±0.13
金丝桃苷 Hyperoside	0.40 ±0.02	0.44 ±0.02	0.26 ±0.01	0.35 ±0.01	0.55 ±0.01	0.28 ±0.08	0.10 ±0.01	0.47 ±0.06	0.28 ±0.04	0.20 ±0.05
柚皮苷 Naringin	1.86 ±0.11	1.06 ±0.08	1.21 ±0.11	2.48 ±0.14	1.49 ±0.19	0.68 ±0.05	0.63 ±0.04	0.60 ±0.10	11.12 ±0.83	0.28 ±0.17
紫杉叶素 Taxifolin	0.69 ±0.06	1.17 ±0.07	1.85 ±0.23	0.99 ±0.01	0.81 ±0.10	0.38 ±0.09	0.16 ±0.02	0.21 ±0.05	0.06 ±0.03	0.17 ±0.02

铁皮石斛的黄酮类成分测定及其生物可及性研究

Determination of flavonoids in Dendrobium officinale Kimura et Migo and study on its bioavailability

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黄酮 Flavonoids	保留时间 Retention time/min	母离子 Parent ion/ (m/z)	子离子 Product ion/ (m/z)	Q1偏转电压 Q1 deflection voltage/eV	碰撞能 Collision energy/eV	Q2偏转电压 Q2 deflection voltage/eV
柚皮素Naringenin	4.36	271.1	151.20^*	14	18	10
			119.20	18	25	24
槲皮素Quercetin	4.35	301.1	151.10^*	23	23	29
			179.10	22	17	19
芦丁Rutin	3.95	609.0	300.05^*	22	40	23
			271.00	22	54	12
异鼠李素Isorhamnetin	4.52	315.1	300.10^*	12	23	14
			151.00	23	28	16
芹菜素Apigenin	4.54	269.1	117.10^*	10	34	23
			151.05	20	24	15
圣草酚Eriodictyol	4.19	287.1	150.90^*	11	17	25
			134.95	15	14	21
金圣草黄素Chrysoeriol	4.56	299.1	284.05^*	11	21	13
			256.05	23	28	26
橙皮素Hesperetin	4.39	301.1	164.05^*	11	24	17
			286.00	22	18	22
异槲皮苷Isoquercitrin	3.97	463.1	300.05^*	24	30	10
			271.05	11	45	19
槲皮苷Quercitrin	4.10	447.1	300.05^*	16	29	10
			301.10	17	22	21
木犀草苷Luteoloside	3.92	447.1	285.00^*	13	29	13
			283.85	17	38	27
山柰酚Kaempferol	4.52	285.1	187.00^*	11	26	10
			117.00	19	38	24
夏佛塔苷Schaftoside	3.79	563.1	353.05^*	20	37	12
			383.10	20	36	18
芹菜苷Apiin	3.99	563.1	269.05^*	22	32	13
			431.10	20	28	21
金丝桃苷Hyperoside	3.97	463.2	300.10^*	17	29	10
			270.90	17	46	18
柚皮苷Naringin	3.92	579.2	271.10^*	22	34	19
			151.00	22	45	29
紫杉叶素Taxifolin	3.87	303.1	285.05^*	11	12	13
			125.10	22	20	22

样品 Sample	黄酮单体 Flavonoid component	生物可及性Bioavailability/%
样品 Sample	黄酮单体 Flavonoid component	胃-小肠 Gastrointestinal	结肠 Colonic
TP1	柚皮素 Naringenin	9.52±0.22	3.52±0.19
	芦丁 Rutin	8.09±0.13	2.63±0.06
	夏佛塔苷 Schaftoside	40.63±3.41	11.44±0.53
TP2	柚皮素 Naringenin	11.34±0.27	5.03±0.18
	芦丁 Rutin	6.21±0.18	3.49±0.18
	夏佛塔苷 Schaftoside	32.39±5.70	10.18±0.91
TP3	柚皮素 Naringenin	8.23±0.20	4.62±0.36
	芦丁 Rutin	3.84±0.18	2.61±0.32
	夏佛塔苷 Schaftoside	29.09±3.65	11.72±0.28
TP4	柚皮素 Naringenin	9.17±0.35	4.44±0.20
	芦丁 Rutin	5.32±0.31	1.78±0.02
	夏佛塔苷 Schaftoside	25.2±5.01	7.73±0.23
TP5	柚皮素 Naringenin	9.57±0.47	4.94±0.11
	芦丁 Rutin	4.12±0.12	1.85±0.10
	夏佛塔苷 Schaftoside	24.26±3.09	8.21±0.43
TP6	柚皮素 Naringenin	15.88±2.50	3.43±0.83
	芦丁 Rutin	22.87±2.12	1.87±0.30
	夏佛塔苷 Schaftoside	42.65±2.47	13.33±1.40
TP7	柚皮素 Naringenin	13.29±1.77	2.90±0.41
	芦丁 Rutin	21.49±1.75	5.70±0.34
	夏佛塔苷 Schaftoside	30.62±4.84	5.34±1.04
TP8	柚皮素 Naringenin	14.45±2.23	2.12±0.30
	芦丁 Rutin	12.55±1.48	2.04±0.20
	夏佛塔苷 Schaftoside	41.71±3.62	11.53±0.61
TP9	柚皮素 Naringenin	18.37±2.93	5.67±0.58
	芦丁 Rutin	10.22±1.18	3.92±0.84
	夏佛塔苷 Schaftoside	39.84±3.06	9.99±0.58
TP10	柚皮素 Naringenin	16.96±1.74	2.73±0.38
	芦丁 Rutin	1.85±0.20	1.42±0.04
	夏佛塔苷 Schaftoside	40.57±4.11	6.77±0.91

指标 Index	DPPH自由基清除能力 DPPH free radical scavenging ability	FRAP总抗氧化能力 FRAP total antioxidant capacity
总黄酮	0.920^**	0.929^**
Total flavonoids
柚皮素Naringenin	0.806^**	0.737^**
芦丁Rutin	0.852^**	0.815^**
夏佛塔苷	0.764^**	0.846^**
Schaftoside

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