奇楠与传统沉香特征成分的差异性分析及其生物活性研究

doi:10.3969/j.issn.0253-2417.2023.05.009

摘要/Abstract

摘要：

分别采用冷提法(CE)和热提法(HE), 以水和乙醇为溶剂制备奇楠(QN)、传统沉香(TA)提取物, 通过GC-MS和HPLC法对提取物的化学成分进行分析, 并探讨了其抗氧化活性和抑菌活性。研究结果表明：QN中倍半萜类化合物的种类少于TA, 但是两者共有的倍半萜类化合物含量QN高于TA。QN中基本不含四氢-2-(2-苯乙基)色酮(THPECs), 主要含有Flidersia型2-(2-苯乙基)色酮(FTPECs), 其中2-(2-苯乙基)色酮质量分数可达10.87%, 2-[2-(4-甲氧基苯)乙基] 色酮质量分数为4.80%。TA中THPECs种类和含量丰富, 沉香四醇质量分数可达1.50%。QN与TA提取物对ABTS自由基清除能力和铁离子还原能力均随乙醇体积分数(0~55%)提高而增加, QN水提取物的抗氧化活性低于TA, 但乙醇提取物抗氧化活性优于TA。QN和TA提取物对大肠杆菌无显著的抑菌活性, 两者水提取物对白色念珠菌均具有抑菌活性。

关键词: 奇楠沉香, 传统沉香, 化学成分, 抗氧化活性, 抑菌活性

Abstract:

The extracts of Qinan(QN) and traditional agarwood(TA) were prepared by cold extraction(CE) and hot extraction(HE) with water and ethanol as solvent, respectively. The chemical constituents of the extracts were analyzed by GC-MS and HPLC, and their antioxidant and antibacterial activities were studied. The results showed that the species of sesquiterpenoids in QN were less than those of TA, while the contents of sesquiterpenoids in both were higher than that of TA. There was almost no tetrahydro-2-(2-phenylethyl) chromones(THPECs) in QN, and Flidersia type 2-(2-phenylethyl) chromones(FTPECs) was contained, where the mass fraction of 2-(2-phenethyl) chromone could reach 10.87%, and the mass fraction of 2-[2-(4-methoxy)phenethyl]chromone was 4.80%. The species and contents of THPECs in TA were rich, and the mass fraction of agartetrol could reach 1.50%. With the increasing ethanol volume fraction(0-55%), the ABTS free radical scavenging ability and iron ion reduction ability of QN and TA extracts increased. Although the antioxidant activity of QN water extracts was lower than that of TA, while its ethanol extracts were higher than that of TA. QN and TA had no significant antibacterial activity against Escherichia coli, but their water extracts had antibacterial activity against Candida albicans.

Key words: Qinan agarwood, traditional agarwood, chemical constituents, antioxidant activities, antibacterial activities

中图分类号:

TQ35

胡泽坤, 晏婷婷, 李改云, 秦嘉惠, 吴新文, 陈媛. 奇楠与传统沉香特征成分的差异性分析及其生物活性研究[J]. 林产化学与工业, 2023, 43(5): 63-72.

Zekun HU, Tingting YAN, Gaiyun LI, Jiahui QIN, Xinwen WU, Yuan CHEN. Difference of Characteristic Components and Bioactivities for Qinan and Traditional Agarwood[J]. Chemistry and Industry of Forest Products, 2023, 43(5): 63-72.

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化合物 compound	回归方程 regression equation	线性范围/(mg·L^-1) linear range	R²
沉香四醇agarotetrol	y=22 801x+57 056	20-320	0.999 9
4'-甲氧基沉香四醇4'-methoxyagarotetrol	y=24 505x-16 597	12.5-200	0.999 7
异沉香四醇isogarotetrol	y=36 905x-5 677	12.5-200	0.999 9
6-羟基-2-(2-苯乙基)色酮 6-hydroxy-2-(2-phenylethyl) chromone	y=29 754x+37 466	10-160	0.998 3
6, 7-二甲氧基-2-(2-苯乙基)色酮 6, 7-dimethoxy-2-(phenylethyl) chromone	y=18 502x+56 007	10-160	0.999 4
2-(2-苯乙基)色酮 2-(2-phenylethyl) chromone	y=18 127x+219 614	42.5-680	0.991 3

序号 No.	t_R/min	化合物 compound	分子式 molecular formula	相对峰面积relative peak area/%
				冷提法cold extraction method			热提法hot extraction method
				H₂O	35%ET	55%ET	H₂O	35%ET	55%ET
1	19.00	α-檀香醛α-santalal	C₁₅H₂₄O	—	0.02	0.07	—	0.05	0.13
2	24.68	蛇麻烯humulene^△	C₁₅H₂₄	—	0.02	0.11	—	0.07	0.18
3	25.76	石竹烯氧化物caryophyllene oxide	C₁₅H₂₄O	—	0.02	0.08	0	0.06	0.13
4	27.11	绿花白千层醇viridiflorol	C₁₅H₂₆O	—	0.03	0.06	0.02	0.06	0.10
5	30.92	依兰醇ylanganol	C₁₅H₂₄O	—	0.12	0.17	0.01	0.20	0.27
6	32.19	epi-荜澄茄醇epi-cadinol	C₁₅H₂₆O	—	—	—	—	—	—
7	33.12	异榄香烯isoelemene^△	C₁₅H₂₄	0.02	0.03	0.26	—	0.21	0.49
8	33.54	epi-γ-桉油烯醇epi-γ-spathulenol	C₁₅H₂₆O	0.02	0.08	0.40	0.11	0.29	0.52
9	36.98	布黎醇bulnesol	C₁₅H₂₆O	—	—	—	—	—	—
10	37.28	β-桉油烯醇β-spathulenol	C₁₅H₂₆O	—	0.02	0.04	0.02	0.04	0.50
11	37.50	长松叶烯longifolene^△	C₁₅H₂₄	—	—	—	—	—	—
12	37.71	α-木香醛α-costal	C₁₅H₂₂O	—	0.13	0.28	0.02	0.24	0.48
13	39.05	香橙烯aromadendrene^△	C₁₅H₂₄	0.02	0.12	0.22	0.04	0.21	0.30
14	44.01	桉叶油醇eudesmol	C₁₅H₂₄O	—	—	—	—	—	—

序号 No.	t_R/min	化合物 compound	分子式 molecular formula	相对峰面积relative peak area/%
				冷提法cold extraction method			热提法hot extraction method
				H₂O	35%ET	55%ET	H₂O	35%ET	55%ET
1	19.00	α-檀香醛α-santalal	C₁₅H₂₄O	—	0.02	0.03	—	0.02	0.03
2	24.68	蛇麻烯humulene^△	C₁₅H₂₄	—	0.01	0.01	0.04	0.02	0.02
3	25.76	石竹烯氧化物caryophyllene oxide	C₁₅H₂₄O	—	0.02	0.03	0.02	0.02	0.02
4	27.11	绿花白千层醇viridiflorol	C₁₅H₂₆O	—	0.02	0.04	0.03	0.03	0.04
5	30.92	依兰醇ylanganol	C₁₅H₂₄O	—	0.06	0.21	0.11	0.18	0.21
6	32.19	epi-荜澄茄醇epi-cadinol	C₁₅H₂₆O	—	0.02	0.05	0.04	0.04	0.05
7	33.12	异榄香烯isoelemene^△	C₁₅H₂₄	—	0.02	0.02	—	0.02	0.03
8	33.54	epi-γ-桉油烯醇epi-γ-spathulenol	C₁₅H₂₆O	0.02	0.06	0.16	0.13	0.17	0.15
9	36.98	布黎醇bulnesol	C₁₅H₂₆O	—	0.03	0.07	0.04	0.06	0.06
10	37.28	β-桉油烯醇β-spathulenol	C₁₅H₂₆O	0.02	0.03	0.06	0.07	0.06	0.06
11	37.50	长松叶烯longifolene^△	C₁₅H₂₄	—	0.04	0.14	—	0.05	0.14
12	37.71	α-木香醛α-costal	C₁₅H₂₂O	—	0.02	0.15	0.05	0.10	0.15
13	39.05	香橙烯aromadendrene^△	C₁₅H₂₄	—	0.04	0.13	0.03	0.05	0.13
14	44.01	桉叶油醇eudesmol	C₁₅H₂₄O	0.02	0.02	0.03	0.02	0.03	0.03

序号 No.	t_R/min	[M+H]⁺	化合物 compound	质量分数 mass fraction/%
				冷提法cold extraction method			热提法hot extraction method
				H₂O	35%ET	55%ET	H₂O	35%ET	55%ET
1	14.28	319	沉香四醇agarotetrol^*	—	0.01	0.02	0.09	0.06	0.04
2	14.63	349	4’-甲氧基沉香四醇 4’-methoxyagarotetrol^*	—	—	—	—	—	—
3	15.66	319	异沉香四醇isogarotetrol^*	—	—	—	—	—	—
4	33.53	313	6-羟基-2-[2-(4-羟基-3-甲氧基苯)乙基]色酮 6-hydroxy-2-[2-(4-hydroxy-3-methoxy phenyl)ethyl]chromone	—	0.09	0.20	—	0.11	0.27
5	42.48	267	2-[2-(3-羟基苯)乙基]色酮 2-[2-(3-hydroxyphenyphenyl) ethyl) chromone	—	0.09	0.23	—	0.12	0.43
6	43.41	297	2-[2-(3-羟基-4-甲氧基苯)乙基]色酮 2-[2-(3-hydroxy-4-methoxyphenyl) ethyl]chromone	—	0.09	0.17	—	0.11	0.27
7	45.74	297	2-[2-(3-甲氧基-4羟基苯)乙基]色酮 2-[2-(3-methoxy 4-hydroxyphenyl)ethyl]chromone	—	0.39	0.86	—	0.50	0.99
8	50.92	267	2-[2-(4’-羟基苯)乙基]色酮 2-[2-(4’-hydroxyphenyl) ethyl]chromone	—	0.06	0.23	—	0.09	0.42
9	53.31	297	6-羟基-2-[2-(4’-甲氧基苯)乙基]色酮 6-hydroxy-2-[2-(4’-methoxyphenyl)ethyl]chromone	—	0.08	0.45	—	0.15	0.75
10	54.83	267	6-羟基-2-(2-苯乙基)色酮 6-hydroxy-2-(2-phenylethyl) chromone^*	—	0.04	0.21	—	0.07	0.47
11	62.51	311	6, 7-二甲氧基-2-(2-苯乙基)色酮 6, 7-dimethoxy-2-(2-phenylethyl)chromone^*	—	0.07	0.11	—	0.09	0.28
12	68.45	281	2-[2-(4-甲氧基苯)乙基]色酮 2-[2-(4-methoxyphenyl) ethyl]chromone	—	0.52	3.43	—	1.01	4.80
13	69.91	251	2-(2-苯乙基)色酮 2-(2-phenylethyl)chromone^*	—	0.87	5.41	—	1.70	10.87

序号 No.	t_R/min	[M+H]⁺	化合物 compound	质量分数mass fraction/%
				冷提法cold extraction method			热提法hot extraction method
				H₂O	35%ET	55%ET	H₂O	35%ET	55%ET
1	14.28	319	沉香四醇agarotetrol^*	0.73	0.70	0.73	1.50	1.19	1.23
2	14.63	349	4’-甲氧基沉香四醇 4’-methoxyagarotetrol^*	0.09	0.10	0.12	0.26	0.19	0.20
3	15.66	319	异沉香四醇isogarotetrol^*	0.10	0.09	0.10	0.17	0.15	0.16
4	33.53	313	6-羟基-2-[2-(4-羟基-3-甲氧基苯)乙基]色酮 6-hydroxy-2-[2-(4-hydroxy-3-methoxy phenyl)ethyl]chromone	—	0.03	0.07	0.02	0.07	0.12
5	42.48	267	2-[2-(3-羟基苯)乙基]色酮 2-[2-(3-hydroxyphenyl) ethyl) chromone	—	0.04	0.10	—	0.07	0.18
6	43.41	297	2-[2-(3-羟基-4-甲氧基苯)乙基]色酮 2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone	—	0.02	0.06	—	0.04	0.10
7	45.74	297	2-[2-(3-甲氧基-4羟基苯)乙基]色酮 2-[2-(3-methoxy 4-hydroxyphenyl) ethyl]chromone	—	—	—	—	—	—
8	50.92	267	2-[2-(4’-羟基苯)乙基]色酮 2-[2-(4’-hydroxyphenyl) ethyl]chromone	—	0.05	0.14	—	0.07	0.22
9	53.31	297	6-羟基-2-[2-(4’-甲氧基苯)乙基]色酮 6-hydroxy-2-[2-(4’-methoxyphenyl)ethyl]chromone	—	0.10	0.26	—	0.13	0.40
10	54.83	267	6-羟基-2-(2-苯乙基)色酮 6-hydroxy-2-(2-phenylethyl) chromone^*	—	0.16	0.35	—	0.20	0.54
11	62.51	311	6, 7-二甲氧基-2-(2-苯乙基)色酮 6, 7-dimethoxy-2-(2-phenylethyl)chromone^*	—	0.01	0.21	—	0.14	0.40
12	68.45	281	2-[2-(4-甲氧基苯)乙基]色酮 2-[2-(4-methoxyphenyl) ethyl]chromone	—	0.15	0.28	—	0.04	0.44
13	69.91	251	2-(2-苯乙基)色酮 2-(2-phenylethyl)chromone^*	—	0.12	0.45	—	0.16	0.70