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

Abstract

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

CLC Number:

TQ35

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.

Figures/Tables 7

Table 1

Fig.1

Table 2

Table 3

Fig.2

Table 4

Table 5

References 25

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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

Difference of Characteristic Components and Bioactivities for Qinan and Traditional Agarwood

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