大花序桉叶片黄酮类物质提纯及其活性分析

doi:10.11707/j.1001-7488.LYKX20240630

摘要/Abstract

摘要：

目的: 对大花序桉叶片黄酮类化合物进行分离鉴定和活性分析，为大花序桉叶片黄酮类化合物的开发利用提供参考依据。方法: 利用大孔树脂对大花序桉叶片黄酮类化合物进行纯化，比较8种净品级大孔树脂（X-5、ADS-17、D3520、HPD100、HPD722、HC-200、HPD400和AD201）对大花序桉叶片总黄酮的吸附和解吸特性，筛选最佳纯化树脂，并对纯化参数进行优化；应用红外光谱、超高效液相色谱-质谱联用（UHPLC-MS）技术对黄酮类化合物进行结构鉴定和定量分析，对比纯化前后黄酮类化合物的体外抗氧化活性[如1,1-二苯基-2-苦基肼自由基（DPPH）清除率、2,2-连氮基-双-3-乙基苯并噻唑啉-6-磺酸二铵盐（ABTS）清除率、总还原力]、酶抑制活性（乙酰胆碱酯酶、α-葡萄糖苷酶）和抗菌活性（大肠杆菌、金黄色葡萄球菌、枯草芽孢杆菌、欧文氏菌）。结果: ADS-17树脂对大花序桉叶片总黄酮富集效果最佳，最优纯化工艺条件为：pH=3、洗脱剂乙醇体积分数50%、上样液质量浓度0.9 mg·mL^–1、吸附速率2.0 mL·min^?1、洗脱速率1.0 mL·min^?1、洗脱剂用量65 mL，在此条件下，总黄酮提取物纯度由20.03 mg·g^–1提高至36.31 mg·g^–1；经红外光谱扫描发现，其含有黄酮类物质特征吸收峰，进一步利用UHPLC-MS鉴定出13种黄酮类物质；与粗提物相比，纯化物黄酮类化合物的色谱峰变得更为突出，其中杨梅黄酮、杨梅苷和槲皮素纯化后的含量比纯化前分别高1.67、1.64和3.57倍；大花序桉叶片黄酮纯化物的抗氧化能力优于粗提物，其中纯化物DPPH和ABTS的半抑制质量浓度（IC₅₀）分别比粗提物降低0.77和11.31 μg·mL^–1，与抗坏血酸（VC）的IC₅₀差异不显著（P>0.05）；纯化物对乙酰胆碱酯酶和α-葡萄糖苷酶活性的抑制能力明显提高，其IC₅₀分别比粗提物降低45.26和1.60 μg·mL^–1；纯化物的抑菌效果也强于粗提物，粗提物对大肠杆菌、金黄色葡萄球菌、欧文氏杆菌和枯草芽孢杆菌的最小抑菌质量浓度在12.50~25.00 mg·mL^–1范围内，而纯化物对以上菌种的最小抑菌质量浓度均小于6.25 mg·mL^–1。结论: ADS-17大孔树脂可有效富集大花序桉叶片黄酮类化合物，纯化后的总黄酮具有良好的抗氧化、酶抑制和抑菌活性。

关键词: 大花序桉叶片, 黄酮类化合物, 大孔树脂, 成分鉴定, 生物活性

Abstract:

Objective: This study aims to provide a theoretical basis for the exploitation and utilization of Eucalyptus cloeziana leaves by isolating, and identifying the leaf flavonoids and determining their activity. Method: In this study, the eight different macroporous resins were used to purify flavonoids from E. cloeziana leaves, and their adsorption/desorption characteristics of total flavonoids in E. cloeziana leaves were compared to select a macroporous resin suitable for purifying flavonoids from E. cloeziana leaves, and optimize the purification parameters. The structure and content of flavonoids were investigated with infrared spectroscopy and ultra-high performance liquid chromatography-mass spectrometry (UHPLC-MS). In addition, the antimicrobial activity of flavonoids before and after purification against four bacterial strains of Staphylococcus aureus, Staphylococcus aureus, Bacillus subtilis, and Erwinia carotovora was investigated. At the same time, the in vitro antioxidant activity [such as 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging rate, 2,2-diazo-bis (3-ethyl-benzothiazole-6-sulfonic acid) diammonium (ABTS) free radical scavenging rate and total reducting capacity] and enzyme inhibitory activity (acetylcholinesterase, α-glucosidase) were also determined. Result: The ADS-17 resin was identified as the optimum choice for its exceptional adsorption and desorption properties, and the optimal purification process conditions were as follows: pH value of 3, eluent ethanol volume fraction of 50%, concentration of flavonoids in the sample solution of 0.9 mg·mL^–1, adsorption rate of 2.0 mL·min^?1, elution rate of 1.0 mL·min^–1 and eluent dosage of 65 mL. Under these conditions, the purity of the total flavonoid extract was increased from 20.03 mg·g^–1 to 36.31 mg·g^–1. Through infrared spectroscopy scanning, it was shown that the extract contained characteristic absorption peaks of flavonoids. And then, a total of 13 flavonoids were identified by UHPLC-MS. Compared to the crude extract, the flavonoids peaks of the purified extract were more prominent, among which myricetin, myricitrin and quercetin were 1.67, 1.64 and 3.57 times higher than before purification, respectively. The antioxidant capacity of purified flavonoids from E. cloeziana leaves was superior to that of the crude extract. And the half inhibitory concentration (IC₅₀) values of the purified DPPH and ABTS were lower than those of the crude extract by 0.77 and 11.31 μg·mL^–1, respectively, and the difference in IC₅₀value with VC was not significant (P>0.05). In addition, the purified extracts showed significantly higher inhibitory ability on acetylcholinesterase and α-glucosidase activities, and their IC₅₀ values were 45.26 and 1.60 μg·mL^–1 lower than those of crude extracts, respectively. The antibacterial experiment also showed that purified extract was more effective than crude extracts, with the minimum inhibitory concentrations of the crude extracts against Escherichia coli, Staphylococcus aureus, Erwinia carotovora, and Bacillus subtilis ranging from 12.50 to 25.00 mg·mL^–1, while the minimum inhibitory concentrations of the purified extracts against the above species were less than 6.25 mg·mL^–1. Conclusion: ADS-17 macroporous resin can effectively enrich the flavonoids in E. cloeziana leaves, and the purified flavonoids have good antioxidant, enzyme inhibition and bacteriostatic activities.

Key words: Eucalyptus cloeziana leaves, flavonoids, maeroporous resin, component identification, bioactivity

中图分类号:

S792.39

韦柳明,李庆乐,蓝阳,卢梦婷,马若克,韦鹏练,符韵林. 大花序桉叶片黄酮类物质提纯及其活性分析[J]. 林业科学, 2025, 61(8): 80-95.

Liuming Wei,Qingle Li,Yang Lan,Mengting Lu,Ruoke Ma,Penglian Wei,Yunlin Fu. Purification and Activity Analysis of Total Flavonoids from Eucalyptus cloeziana Leaves[J]. Scientia Silvae Sinicae, 2025, 61(8): 80-95.

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大孔树脂 Macroporous resin	极性 Polarity	比表面积 Surface area/(m²·g^–1)	孔径 Pore diameter/nm	吸附量 Adsorption quantity/(mg·g^–1)	吸附率 Adsorption ratio (%)	解吸量 Desorption capacity/(mg·g^–1)	解吸率 Desorption ratio (%)
X-5	非极性Nonpolar	500~600	29~30	12.15 ±0.06	70.09 ±0.32	11.21 ±0.42	92.25 ±3.02
ADS-17	非极性Nonpolar	90~150	25~30	13.99 ±0.04	80.70 ±0.21	12.73 ±0.09	90.95 ±0.68
D3520	非极性Nonpolar	480~520	85~90	13.66 ±0.02	78.79 ±0.09	12.44 ±0.51	91.06 ±3.66
HPD100	非极性Nonpolar	650~700	85~90	13.35 ±0.16	77.01 ±0.91	12.52 ±0.67	93.74 ±4.07
HPD722	弱极性Weak-polar	485~530	130~140	11.75 ±0.15	67.73 ±0.84	11.67 ±0.50	99.38 ±3.04
HC-200	弱极性Weak-polar	≥500	45~55	13.37 ±0.13	77.08 ±0.85	12.68 ±0.32	94.88 ±1.69
AD201	中极性Middle-polar	500~550	75~80	11.76 ±0.01	67.47 ±0.05	11.49 ±0.16	97.71 ±1.34
HPD400	极性 Polar	≥200	100~130	12.96 ±0.09	74.75 ±0.51	11.78 ±0.22	90.87 ±2.31

动力学模型 Kinetic model	方程式 Equation	模型参数 Parameters
准一级动力学模型 Pseudo-first-order	$ {\mathrm{{l}n}}\left({q_{\mathrm{e}}}-{{q{_{{t}}}{ }}}\right)=-0.004\; 5t+2.189\; 9 $	k₁ = ?0.004 5 min^–1 q_e = 8.93 mg·g^–1 R² = 0.958 1
准二级动力学模型 Pseudo-second-order	$ \dfrac{{t}}{{{q}}_{{t}}}{=2.151\; 4+0.053 \;9}{t} $	k₂ = 0.0014 g·mg^–1min^–1 q_e = 18.55 mg·g^–1 R² = 0.998 9
颗粒内扩散模型 Intra-particle diffusion	$ {{q}}_{{t}}{=0.821 \;3}{{t}}^{{1/2}}{+4.647\; 0} $	k₀ = 0.8213 g·mg^–1.min^–1/2 C = 4.647 0 mg·g^–1 R² = 0.996 6
	$ {{q}}_{{t}}{=0.427 \;5}{{t}}^{{1/2}}{+8.951 \;9} $	k₀ = 0.4275 g·mg^–1.min^–1/2 C = 8.951 9 mg·g^–1 R² = 0.989 8
	$ {{q}}_{{t}}{=0.072 \;2}{{t}}^{{1/2}}{+15.539\; 0} $	k₀ = 0.072 2 g·mg^–1.min^–1/2 C = 15.539 0 mg·g^–1 R² = 0.880 2

化合物Compounds	1	2	3	均值Average value
粗提物 Crude extract	20.03	19.93	20.13	20.03±0.08
纯化物 Purified extract	35.62	36.08	37.24	36.31±0.68

序号 No.	保留时间Retention time/min	分子式 Molecule formula	[M+H]⁺		二级质谱碎片离子 Secondary mass spectrometry fragment ion	化合物 Compounds
序号 No.	保留时间Retention time/min	分子式 Molecule formula	理论值 Theoretical	实测值 Measured	二级质谱碎片离子 Secondary mass spectrometry fragment ion	化合物 Compounds
1	6.690	C₁₅H₁₂O₇	305.0655	305.0659	305.0655	花旗松素Taxifolin^*
2	7.158	C₂₁H₂₀O₁₃	481.0976	481.0979	481.0979, 319.1453, 153.0184	杨梅素-3-O-半乳糖苷 Myricetin 3-O-beta-D-galactopyranoside
3	7.823	C₁₅H₁₀O₈	319.0448	319.0453	319.0452, 273.0395, 245.0450, 217.0501, 153.0184, 137.0235	杨梅黄酮 Myricetin^*
4	7.824	C₂₁H₂₀O₁₂	465.1027	465.1033	465.1033, 319.0451, 273.0405, 245.0453, 217.0495, 153.0184	杨梅苷 Myricitrin^*
5	8.553	C₂₁H₂₀O₁₁	449.1078	449.1083	449.1083, 287.0553, 153.0185, 121.0286	山柰酚-7-O-葡萄糖苷 Kaempferol-7-O-glucoside
6	8.806	C₁₅H₁₄O₅	275.0914	275.1618	275.1618, 151.0393, 107.0497	根皮素 Phloretin
7	8.841	C₂₀H₁₈O₁₁	435.0921	435.0926	435.0921, 303.0502, 285.0383, 257.0447, 229.0497, 153.0184	扁蓄苷 Avicularin
8	9.012	C₂₁H₂₀O₁₁	449.1078	449.1082	449.1082, 303.0503, 285.0036, 257.0084, 201.0186, 153.0185	槲皮素-3-鼠李糖苷 Quercitroside
9	9.932	C₂₁H₂₀O₁₀	433.1129	433.1133	433.1133, 287.0553, 213.0545, 153.0184	阿福豆苷 Afzelin
10	9.940	C₁₅H₁₀O₆	287.0550	287.0554	287.0554, 231.0658, 213.0554, 153.0184	山柰酚 Kaempferol
11	9.999	C₂₂H₂₂O₁₀	447.1285	447.1295	447.1295, 285.0761, 257. 080 7	黄豆黄苷 Glycitin
12	10.309	C₁₅H₁₀O₇	303.0499	303.0503	303.0503, 257.0451, 229.0499, 201.0561, 153.0184	槲皮素 Quercetin^*
13	11.580	C₁₆H₁₂O₇	317.0655	317.0658	317.0658	异鼠李素Isorhamnetin^*

试验菌种Microoganisms	粗提物Crude extract		纯化物Purified extract		卡那霉素Kanamycin monosulfate
试验菌种Microoganisms	ZOI/mm	MIC/(mg·mL^–1)	ZOI/mm	MIC/(mg·mL^–1)	ZOI/mm
大肠杆菌Escherichia coli	25.00±1.050	12.50	26.23±0.788	6.25	11.83±1.027
欧文氏杆菌Erwinia carotovora	9.65±0.919	25.00	11.37±0.519	6.25	24.72±0.473
金黄色葡萄球菌Staphylococcus aureus	12.50±1.225	12.50	12.80±0.471	3.13	21.72±0.781
枯草芽孢杆菌Bacillus subtilis	11.17±0.236	12.50	16.00±0.408	6.25	24.33±0.471