不同产地沉香的高效液相色谱指纹特征

doi:10.11707/j.1001-7488.20210215

Abstract

Abstract:

Objective: In view of the differences in the quality of agarwood from different origins and the identification of traditional agarwood origin relying on experience judgment, high performance liquid chromatography(HPLC) fingerprint characteristics of agarwood from different origins were studied, and the feasibility of chromatographic fingerprint analysis technology for traceability of agarwood origin was also discussed. Method: 36 batches of agarwood from three origins were analyzed by optimized HPLC. The retention time and area of chromatographic peaks was obtained by the similarity evaluation system of chromatographic fingerprints of traditional Chinese medicines. HPLC fingerprints of agarwood from three different production regions were established. Principal component analysis(PCA) and orthogonal partial least squares discriminant analysis(OPLS-DA) was used to establish the discriminant methods of agarwood from different origins. Result: By analyzing the 85 characteristic peak variables of the HPLC fingerprint of agarwood from three different origins, it was found that the species and relative content of 2-(2-phenylethyl) chromone composition were the most abundant in Guan-Xiang Zone. In Sin-Chew Zone, the peaks of agarotetrol were extremely high and the relative content of the other chromones was relatively low. There were more species of 2-(2-phenylethyl) chromone in the samples of Hoi-An Zone, whose relative content was slightly lower than that in Guan-Xiang Zone and slightly higher than that in the Sin-Chew Zone. According to the geographical distribution of the origins, the samples of Hoi-An Zone showed certain transition characteristics in the three production origins. PCA analysis showed that the samples could basically be aggregated into three categories according to the origin. The accuracy of OPLS-DA analysis method in identifying the sample origin of training set and test set was 100%. Conclusion: The composition and relative content of 2-(2-phenylethyl) chromophenone in agarwood from different origins might be quite different, showing a certain extent of regional characteristics. The origin of agarwood could be identified by HPLC combined with OPLS-DA.

Key words: agarwood, HPLC(high performance liquid chromatography) fingerprint characteristics, origin, OPLS-DA(orthogonal partial least squares discriminant analysis)

CLC Number:

Qian Wang,Lili Shang,Tingting Yan,Yuan Chen,Yuejin Fu,Gaiyun Li. HPLC Fingerprint Characteristics of Agarwood from Different Origins[J]. Scientia Silvae Sinicae, 2021, 57(2): 150-159.

Figures/Tables 9

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Table 1

Chromatographic peaks of 34 compounds with significant differences between different regions in OPLS-DA model"

序号 No.	色谱峰编号 ID of chromatogram peaks	保留时间 Retention time/min	前体离子 [M+H]⁺/(m/z)Protonated precursorion/(m/z)	二级质谱碎片离子 MS/MS framents ions	推荐色酮化合物 Proposed compound	重要性值 VIP value
1	43	66.777	281.194 9	121	2-[2-(4-甲氧基)苯乙基]色酮2-[2-(4-Methoxy)phenylethyl]chromone	1.896 1
2	1	6.913	365.114 1	347, 329	沉香色酮A Aquilarone A	1.788 0
3	29	42.990	297.112 0	137	2-[2-(3-甲氧基-4-羟基苯基)乙基]色酮2-[2-(3-Methoxy-4-hydroxyphenyl)ethyl]chromone	1.436 7
4	10	19.770	331.117 7	313, 285	四氢色酮L Tetrahydrochromone L	1.379 4
5	20	26.740	283.096 6	255	Oxidoagarochromone A	1.286 0
6	46	71.887	281.116 3	190, 91	6-甲氧基-2-(2-苯乙基)色酮6-Methoxy-2-(2-phenylethyl)chromone	1.276 4
7	16	23.488	329.100 3	301, 137	(5α, 6α, 7α, 8β)-5, 6, 7, 8-二环氧-2-[2-(3-羟基-4-甲氧基苯基)乙基]-5, 6, 7, 8-四氢色酮(5α, 6α, 7α, 8β)-5, 6, 7, 8-Diepoxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5, 6, 7, 8-tetrahydrochromone	1.246 5
8	M	15.986	319.119 4	301, 283	沉香色酮B Aquilarone B	1.246 5
9	4	13.468	349.217 9	331, 313	(5S, 6R, 7S)-5, 6, 7-三羟基-2-(3-羟基-4-甲氧基苯乙基)-5, 6, 7, 8-四氢色酮(5S, 6R, 7S)-5, 6, 7-Trihydroxy-2-(3-hydroxy-4-methoxyphenylethyl)-5, 6, 7, 8-tetrahydrochromone	1.211 6
10	e	30.159	313.106 5	137	6-羟基-2-[2-(3-羟基-4-甲氧基)苯乙基]-色酮6-Hydroxy-2-[2-(3-hydroxy-4-methoxyl)phenylethyl]-chromone	1.198 1
11	42	64.586	281.116 9	91	6-羟基-2-(2-苯乙基)色酮6-Hydroxy-2-(2-phenylethyl)chromone	1.194 9
12	C	9.348	319.105 2	301, 283	5β, 6β, 7α, 8β-四羟基-2-(2-苯乙基)-5, 6, 7, 8-四氢色酮5β, 6β, 7α, 8β-Tetrahydroxy-2-(2-phenylethyl)-5, 6, 7, 8-tetarahydrochromone	1.186 4
13	H	13.072	319.118 3	301, 283	(5S, 6S, 7R)-5, 6, 7-三羟基-2-[2-(羟基苯基)乙基]-5, 6, 7, 8-四氢色酮(5S, 6S, 7R)-5, 6, 7-Trihydroxy-2-[2-(hydroxyphenyl)ethyl]-5, 6, 7, 8-tetrahydrochromone	1.169 8
14	O	22.794	383.089 5	365, 347	(5α, 6β, 7β, 8α)-8-氯-5, 6, 7-三羟基-2-[2-(3-羟基-4-甲氧基苯基)乙基]-5, 6, 7, 8-四氢色酮(5α, 6β, 7β, 8α)-8-Chloro-5, 6, 7-trihydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5, 6, 7, 8-tetrahydro-chromone	1.168 8
15	d	12.172	349.128 1	331, 313	(5S, 6R, 7R)-5, 6, 7-三羟基-2-[2-(3-羟基-4-甲氧基苯基)乙基]-5, 6, 7, 8-四氢色酮(5S, 6R, 7R)-5, 6, 7-Trihydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5, 6, 7, 8-tetrahydrochromone	1.157 6
16	13	22.033	329.102 1	301	Oxidoagarochromone C	1.118 7
17	J	14.376	349.128 4	331, 313	(5S, 6R, 7R, 8S)-2-[2-(4-甲氧基)苯乙基]-5, 6, 7, 8-四氢色酮(5S, 6R, 7R, 8S)-2-[2-(4-methoxy)phenylethyl]-5, 6, 7, 8-tetrahydrochromone	1.102 1
18	p	76.687	297.082 3	121	6-甲氧基-2-[2-(4-羟基苯基)乙基]色酮6-Methoxy-2-[2-(4-hydroxyphenyl)ethyl]chromone	1.101 1
19	6	17.324	347.111 4	329, 301	5, 6-环氧-7, 8-二羟基-2-[2-(3-羟基-4-甲氧基)苯乙基]-5, 6, 7, 8-四氢色酮5, 6-Edroxy-7, 8-dihydroxy-2-[2-(3-hydroxy-4-methoxy)phenylethyl]-5, 6, 7, 8-tetrahydrochromone	1.100 4
20	37	53.731	313.105 8	121	5, 8-二环氧-2-[2-(4-甲氧基)苯乙基]色酮5, 8-Dihydroxy-2-[2-(4-methoxy)phenylethyl]chromone	1.099 5
21	N	16.288	349.127 3	331, 313	沉香色酮C Aquilarone C	1.086 1
22	f	30.615	313.106 2	285, 121	Oxidoagarochromone B	1.074 3
23	D	9.780	365.123 2	347, 330	5, 6, 7, 8-四羟基-2-(3-羟基-4-甲氧基苯乙基)-5, 6, 7, 8-四氢-4H-色烯-4-酮5, 6, 7, 8-Tetrahydroxy-2-(3-hydroxy-4-methoxyphenylethyl)-5, 6, 7, 8-tetarahydro-4H-chromen-4-one	1.069 0
24	F	11.109	365.218 2	347, 329	5α, 6α, 7α, 8β-四羟基-2-[2-(3-羟基-4-甲氧基苯基)乙基]-5, 6, 7, 8-四氢色酮5α, 6α, 7α, 8β-Tetrahydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5, 6, 7, 8-tetarahydrochromone	1.067 4
25	i	35.051	313.107 5	285	6, 8-二环氧-2-[2-(4-甲氧基)苯乙基]色酮6, 8-Dihydroxy-2-[2-(4-methoxy)phenylethyl]chromone	1.061 9
26	3	11.704	349.128 9	331, 313	5α, 6β, 7β, 8α-四羟基-2-[2-(4-甲氧基苯基)乙基]-5, 6, 7, 8-四氢色酮5α, 6β, 7β, 8α-Tetrahydroxy-2-[2-(4-methoxyphenyl)ethyl]-5, 6, 7, 8-tetrahydrochromone	1.050 0
27	c	11.338	365.296 8	347, 329	5α, 6β, 7β, 8α-四羟基-2-[2-(3-羟基-4-甲氧基苯基)乙基]-5, 6, 7, 8-四氢色酮5α, 6β, 7β, 8α-Tetrahydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5, 6, 7, 8-tetarahydrochromone	1.049 8
28	7	17.728	347.113 0	329, 301	5α, 6α-环氧-7β, 8α, 3′-三羟基-4′-甲氧基- 2-(2-苯乙基)色酮5α, 6α-Epoxy-7β, 8α, 3′-trihydroxy-4′-methoxy- 2-(2-phenylethyl)chromone	1.046 5
29	27	41.099	283.085 4	177, 107	6-羟基-2-[2-(2-羟基苯基)乙基]色酮6-Hydroxy-2-[2-(2-hydroxyphenyl)ethyl]chromone	1.042 1
30	41	61.576	311.127 5	220, 91	6, 7-二甲氧基-2-(2-苯乙基)色酮6, 7-Dimethoxy-2-(2-phenylethyl)chromone	1.040 2
31	24	33.069	329.102 5	137	6, 8-二环氧-2-[2-(3-羟基-4-甲氧基)苯乙基]-色酮6, 8-Dihydroxy-2-[2-(3-hydroxy-4-methoxyl)phenylethyl]-chromone	1.019 0
32	B	8.249	365.795 7	347, 329	沉香色酮D Aquilarone D	1.016 4
33	a	8.681	365.123 2	347, 329	沉香色酮E Aquilarone E	1.014 3
34	34	48.754	327.121 8	137	6-甲氧基-2-[2-(3-羟基-4-甲氧基)苯乙基]色酮6-Methoxy-2-[2-(3-hydroxy-4-methoxy)phenylethyl]-chromone	1.009 6

Table 1

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HPLC Fingerprint Characteristics of Agarwood from Different Origins

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