3个产区沉香燃烧烟气特征化学成分分析

doi:10.11707/j.1001-7488.LYKX20230341

Abstract

Abstract:

Objective: In this study, the releasing or pyrolysis of main components in agarwood were analyzed, volatiles and semi-volatiles released by incense of agarwood from Guan-Xiang Zone, Hoi-An Zone and Sin-Chew Zone were analyzed and compared to identify the odorants and their origins, which explained for the mechanism behind odor formation of agarwood incense and provided references for production zone identification and odor qualification of agarwood. Method: Sesquiterpenoids and 2-(2-phenylethyl) chromones (PECs) were isolated and purified from agarwood resin respectively by hydro distillation or ethanol extraction and precipitation. Thermo-gravity (TG) loss patterns of sesquiterpenoids, PECs and wood were analyzed by TG. Agarwood from 3 production zones were collected and the burning smoke were collected. The volatiles released by burning agarwood were analyzed and the odorants were identified by static headspace-gas-chromatograph-mass spectrum (HS-GC-MS). The PECs in the dust from the smoke were analyzed and preliminarily identified by liquid chromatograph-mass spectrum. The products from different PECs under heating were analyzed and identified by HS-GC-MS. Result: 1) Sesquiterpenoids mostly diffused into air under 200 ℃, PECs pyrolyzed gradually between 150?350 ℃ and wood burned quickly over 250 ℃. 2) Volatiles released by burning agarwood were mainly aromatic compounds and sesquiterpenoids. Types and quantity of aromatic compounds increased, which enriched the agarwood incense with spicy, sweet, almond and floral odors. The release of 7 chemicals including 2-methoxy-4-vinylphenol 3,4-dimethoxyphenol and aceteugenol decreased along with the increase of ethanol extracts of Guan-Xiang zone agarwood. Those chemicals donated smoke, dusty and wood odors. 3) The relative contents of key odor-active compounds such as (-)-spathulenol, cis-eudesm-6-en-11-ol, guaiol were highest in Guan-Xiang Zone agarwood and lowest in Sin-Chew Zone agarwood with Hoi-An Zone agarwood between them. 4) PECs in the dust of agarwood smoke were mainly comprised with Flidersia type 2-(2-phenylethyl) (FPECs) chromones and no tetrahydro-2-(2-phenylethyl) chromones (THPECs) were detected. Agarotetrol pyrolyzed into benzylacetone and benzaldehyde, 2-(2-Phenylethyl) chromone not only pyrolyzed into 6 aromatic compounds including benzaldehyde and benzyl alcohol, but became volatile under heating. Conclusion: Sesquiterpenoids, PECs and wood in agarwood maintained different thermo-mass loss patterns. Sesquiterpenoids acted as volatiles while PECs and wood pyrolyzed into aromatic compounds. Both maintain various odor attributes which impacted on the odor of agarwood incense. Incenses of burning agarwood from 3 production zones differed in the volatile compositions. Agarwood from Sin-Chew Zone diverged with those from Guan-Xiang Zone and Hoi-An Zone. The types and quantity of aromatic compounds released by different PECs when heated differed. FTPECs partly became volatile under heating.

Key words: wild agarwood, production zone, incense, sesquiterpenoids, 2-(2-phenylethyl) chromones

CLC Number:

S781.4

Tingting Yan,Gaiyun Li,Yuan Chen. Analysis for Characteristic Chemicals of Incense of Burning Agarwood from Three Production Zones[J]. Scientia Silvae Sinicae, 2024, 60(10): 122-132.

Figures/Tables 9

Table 1

Fig.1

Fig.2

Table 2

The odorants released by burning agarwood"

序号No.	保留时间 Retention time/min	保留指数 Retention index(DB-5MS)	化合物名称 Compound name	气味描述 Odor attribute	平均相对峰面积Relative area(%)
序号No.	保留时间 Retention time/min	保留指数 Retention index(DB-5MS)	化合物名称 Compound name	气味描述 Odor attribute	国产沉香Guan-Xiang Zone	惠安系 Hoi-An Zone	星洲系 Sin-Chew Zone
1	1.559	610	乙酸Acetic acid*	刺激、酸、醋味 Sharp, pungent, sour vinegar	1.73	0.93	1.41
2	1.925	757	甲苯Toluene	甜香 Sweet	1.66	0.48	0.87
3	2.251	833	呋喃Furfural	甜、木质、杏仁、烘焙谷物 Sweet, woody, almond fragrant, baked bread	1.06	2.48	0.85
4	2.440	855	乙苯Ethylbenzene	苦 Bitter	0.38	0.25	0.27
5	2.657	893	苯乙烯Styrene	甜、香脂、花、塑料 Sweet, balsam, floral, plastic	0.21	0.13	0.26
6	3.327	962	苯甲醛Benzaldehyde*	强烈、刺激、甜、苦、杏仁、樱桃 Strong, sharp, sweet, bitter, almond, cherry	2.94	1.88	3.34
7	4.111	1 021	对甲苯甲醚 p-Methoxytoluene	萘、甲酚、依兰、粉尘、坚果 Naphthyl , cresol, ylang, powdery, nutty	2.49	0.90	0.10
8	4.242	1 036	苯乙醇 Benzyl alcohol*	花、玫瑰、苯酚、香脂 Floral, rose, phenolic, balsamic	0.15	0.17	0.63
9	4.517	1 077	对甲酚p-Cresol	苯酚、水仙、动物、含羞草 Phenolic, narcissus, animal, mimosa	0.43	0.26	0.30
10	4.940	1 169	对乙酰基苯甲醛 p-Acetoxytoluene	水仙、苯酚、动物 Narcissus, phenolic, animal	2.11	0.39	0.82
11	5.415	1 090	2-甲氧基-苯酚 2-Methoxy-phenol	苯酚、烟熏、辛辣、香草、木材 Phenolic, smoke, spice, vanilla, woody	1.03	0.61	0.78
12	5.976	1 110	对乙基苯甲醚p-Ethylanisole	茴芹 Anise	0.45	0.28	0.17
13	7.017	1 156	乙烯基苯甲醚 p-Vinylanisole	甜 Sweet	0.54	0.34	0.40
14	7.309	1 169	对乙基苯酚 p-Ethylphenol	霉 Musty	0.60	0.14	0.39
15	8.027	1 193	2-羟基-4-甲基苯甲醚 Isocreosol	辛辣、丁香、香草、苯酚、药品、皮革、木质、烟熏、燃烧 Spicy, clove, vanilla, phenolic, medicinal, leathery, woody, smoky, burnt	1.90	1.16	1.19
16	8.248	1 193	甲酚Creosol	苯酚 Phenolic	1.48	0.81	1.20
17	9.329	1 235	愈创木酚Guaiacol	苯酚 Phenolic	1.31	0.28	0.21
18	9.861	1 229	1-甲基-1,2,3,4-四氢化萘 1-Methyltetralin	/	0.20	—	0.13
19	10.090	1 232	苄基丙酮Benzylacetone*	花、香脂 Floral, balsam	4.00	2.11	5.74
20	10.468	1 251	对甲氧基苯甲醛 p-Anisaldehyde*	甜、粉尘、含羞草、花、山楂、香脂Sweet, powdery, mimosa, floral, hawthorn, balsam	1.22	1.32	0.77
21	11.051	1 282	2-甲氧基-4-乙基苯酚 2-Methoxy-4-ethylphenol	辛辣、烟熏、火腿、苯酚、丁香 Spicy, smoky, bacon, phenolic, clove	0.17	0.20	—
22	11.452	1 311	4-[(2E)-2-丁烯基]-1,2-二甲苯 4-[(2E)-2-Butenyl]-1,2-dimethylbenzene	/	0.22	0.27	0.47
23	11.555	1 282	对乙基愈创木酚p-Ethylguaiacol	辛辣、烟熏、火腿、苯酚、丁香 Spicy, smoky, bacon, phenolic, clove	0.15	0.27	0.15
24	11.784	1 286	茴香脑Anethole	甜、茴芹、甘草、药品 Sweet, anise, licorice, medicinal	0.20	0.29	0.10
25	12.293	1 306	4-甲氧基甲苯 4-Methoxymethylphenol	/	0.56	0.18	0.12
26	12.934	1 317	2-甲氧基-4-乙烯基苯酚 2-Methoxy-4-vinylphenol	甜、辛辣、丁香、康乃馨、苯酚、辛香料、烟熏、木质、粉尘 Sweet, spicy, clove, carnation, phenolic, peppery, smoky, woody, powdery	0.51	0.34	0.20
27	14.130	1 359	氢化肉桂酸 Hydrocinnamic acid	甜、脂肪、玫瑰、麝香、肉桂 Sweet, fat, rose, musk, cinnamon	0.76	0.56	—
28	14.639	1 365	3,4-二甲氧基苯酚 3,4-Dimethoxyphenol	烟熏、苯酚、火腿、灰尘、木材 Smoke, phenolic, bacon, dusty, woody	1.54	0.61	1.27
29	14.931	1 375	3-烯丙基-6-甲氧基苯酚 3-Allyl-6-methoxyphenol	辛辣、康乃馨 Spicy, carnation	0.33	0.17	0.52
30	16.093	1 387	二氢香豆素Hydrocoumarin	甜、香豆素、椰子、草药、康乃馨、香脂Sweet, coumarinic, coconut, herbal, cinnamon, balsamic	0.22	0.25	0.41
31	16.842	1 404	香草醛Vanillin*	甜、香草、乳脂、巧克力 Sweet, vanilla, creamy, chocolate	0.36	0.39	0.45
32	17.403	1 413	α-cis-香柑油烯α-cis-Bergamotene	辛辣、薄荷Woody， mint	0.15	0.17	0.13
33	17.929	1 432	trans-α-香柑油烯 trans-α-Bergamotene	木材、温暖、茶 Woody, warm, tea	0.15	0.22	0.09
34	18.238	1 388	β- 榄香烯β-Elemene	甜 Sweet	0.12	0.47	0.58
35	18.891	1 439	α- 愈创木烯α-Guaiene	甜、木材、香脂、辛香 Sweet, woody, balsam, spicy	0.10	—	2.14
36	19.377	1 505	α-布藜烯 α-Bulnesene	木材Woody	0.47	1.22	4.38
37	19.451	1 460	香树烯Aromandendrene	木材、薄荷 Woody, mint	0.38	0.25	0.46
38	19.572	1 451	蛇麻烯Humulene	木材 Woody	0.08	0.25	0.71
39	19.775	1 471	乙酰丁香酚Aceteugenol	清新、甜、木材、丁香、康乃馨、麦芽、辛香料 Fresh, sweet, woody clove floral carnation malt spice	0.56	0.47	0.58
40	19.891	1 489	α- 雪松醇α-Cedrol	雪松、木材、干燥、甜、软 Cdarwood, woody, dry, sweet, soft	0.68	0.72	1.28
41	20.630	1 487	γ-芹子烯γ-Selinene	木材 Woody	3.72	0.75	0.13
42	21.231	—	(4R,4aS,6S)-4,4a-二甲氧基-6-(丙-1-烯-2-基)1,2,3,4,4a,5,6,7-八氢萘(4R,4aS,6S)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-1,2,3,4, 4a ,5,6, 7-octahydronaphthalene	谷物、米饭 Grain， rice	1.58	0.93	0.59
43	21.557	—	4a,8-二甲氧基-2-(丙-1-烯-2-基)-1,2,3,4, 4a, 5,6,7-八氢萘 4a,8-Dimethyl-2-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene	脂肪、辛香料、芝麻 Fatty, spicy, seasame	0.39	0.12	0.05
44	21.723	1 482	β-芹子烯β-Selinene	干草Dry grass	1.63	0.72	0.12
45	22.061	1 494	α-芹子烯α-Selinene	琥珀 Amber	3.22	10.83	1.23
46	22.410	1 486	艾里莫芬烯Eremophilene	草药Herbal	0.51	0.71	0.09
47	22.970	-	4-Epi-cis二羟基沉香呋喃 4-Epi-cis-Dihydroagarofuran	药品 Medicine	0.71	0.57	0.1
48	23.440	-	4a,5-二甲氧基-3-(丙-1-烯-2-基)-1,2,3,4,4a,5, 6,7 -八氢萘-1-醇 4a,5-Dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-ol	玫瑰花、烟熏 Rose, floral,smoke	0.76	0.6	—
49	23.543	1 228	香树烯氧化物(1) Aromadendrene oxide-(1)	花香 Sweet	0.39	0.21	0.81
50	23.834	-	β-香橙烯 β-Vatirenene	清新、甜 Fresh, sweet	0.39	—	—
51	24.023	1 547	桉油烯醇(-)-Spathulenol	蜜香 Honey	0.69	0.16	—
52	24.166	1 577	葎草烷-1,6-双烯-3-醇 Humulane-1,6-dien-3-ol	温和、甜、花香Mild, sweet, floral	0.43	0.24	0.14
53	24.344	1 619	2-(4a,8-二甲氧基-1,2,3,4,4a,5,6,7-八氢萘-2-基-丙-2-烯-1-醇 2-(4a,8-Dimethyl-1,2,3,4,4a, 5,6, 7 -octahydro-naphthalen-2-yl)-prop-2-en-1-ol	木材 Woody	0.9	—	0.24
54	24.681	-	刺参萜酮β-Oplopenone	木材、烟熏 Woody, smoke	0.18	0.36	—
55	25.128	1 592	cis-桉叶油6-烯-11-醇 cis-Eudesm-6-en-11-ol	花香 Floral	4.41	2.04	0.1
56	25.460	1 566	蛇麻烯 II环氧化物 Humulene II epoxide	花香、甜、灰尘 Floral, sweet, dusty	0.89	0.33	0.66
57	25.631	1 599	异香树烯氧化物Isoaromadendrene epoxide	烟熏、灰尘Smoke, dusty	0.21	—	0.17
58	25.797	1 612	榄香醇Elemol	辛香、柠檬、树脂 Spicy, citrus, woody resinous	0.57	0.73	0.23
59	26.226	1 590	异缬草萜烯醛 (E)-Isovalencenal	薄荷、草药 Mint, herbal	0.32	—	0.22
60	26.472	-	愈创木醇Guaiol*	玫瑰、灰尘 Rosy, powdery	1.17	0.71	0.29
61	26.615	1 592	绿化白千层醇Viridiflorol	甜、草药、热带水果、薄荷 Sweet, green herbal, fruity tropical, minty	0.36	0.52	0.31
62	27.079	1 592	epi-γ-桉叶油醇γ-Eudesmol	甜、木材 Sweet, woody	0.7	0.47	0.9
63	27.588	-	γ- 桉叶油醇γ-Eudesmol	蜡、甜 Waxy, sweet	0.67	0.62	0.92
64	27.954	1 618	蓝桉醇Globulol*	木材 Woody	0.31	0.13	0.31
65	28.240	1 594	α-檀香醇Santalol, cis,α-	檀香木 Sandalwood woody	3.74	2.9	0.38
66	28.870	-	松柏醇Cedrane-8,13-diol	粉尘 Dusty	0.45	0.35	0.29
67	29.091	-	β-桉叶醇β-Eudesmol*	木材 Woody	0.66	5.31	0.38
68	29.539	1 636	沉香螺醇Agarospirol	辛辣、辛香料、木材 Spicy, peppery, woody	2.77	3.51	1.55
69	29.814	1 642	布藜醇Bulnesol	强烈玫瑰香味 Intensely rosy	1.01	0.64	—
70	29.991	1 655	茅苍术醇Hinesol	辛辣 Spicy	2.66	3.96	3.40
71	30.112	1 636	反式-愈创木-11-烯-10-醇 trans-Guai-11-en-10-ol	粉尘、木材Dusty, woody	0.49	4.03	0.26
72	30.203	-	α-桉叶油醇α-Eudesmol	木材、绿叶 Woody, green	0.72	0.47	0.26
73	31.021	1 643	缬草萜烯醛Valerenal	木材、草药 Woody, herbal	4.08	1.94	7.01
74	31.256	1 642	马鞭草酮Longiverbenone	木材 Woody	1.19	3.46	1.13
75	33.339	1 645	缬草萜烯醇Valerianol	臭味、木材Stinky, woody	1.28	0.57	1.75
76	34.867	-	6-芹子烯-4醇Selin-6-en-4α-ol	木材、草药Woody, herbal	2.86	0.86	1.85
77	35.376	1 680	桉叶油醇-7-烯-4-醇 Eudesm-7(11)-en-4-ol	木材Woody	2.2	1.04	0.20
78	37.070	1 680	圆柚酮Nootkatone	葡萄皮、柠檬、栀子、木材 Grapefruit peel, citrus, gardenia, woody	1.41	0.28	5.02
79	37.390	1 780	异瑟模环烯醇Thunbergol	新鲜叶 Fresh leaf	0.72	0.14	1.56
80	39.032	2 032	木香醇Costol	新鲜叶、花香 Fresh leaf ,floral	3.63	0.59	0.52
81	40.056	1 785	异木香酸甲酯Methyl isocostate	木材、草药 Woody, herbal	0.92	0.50	0.87
82	40.589	-	2,3,4,4a,5,6,7-八氢-1,4a-二甲氧基-7-(2-羟基-1-甲基乙基)2-萘 2-Naphthalenol, 2,3,4,4a, 5,6,7-octahydro-1,4a-dimethyl-7-(2-hydroxy-1-methylethyl)	木材、草药 Woody, herbal	1.28	1.61	0.96
83	41.001	-	穿心莲内酯Andrographolide	木材 Woody	1.67	0.27	0.76

Table 2

Fig.3

Fig.4

Fig.5

Table 3

Fig.6

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编号 No.	产地 Origin	乙醇提取物含量 Ethanol extract content(%)	编号 No.	产地 Origin	乙醇提取物含量 Ethanol extract content(%)	编号 No.	产地 Origin	乙醇提取物含量 Ethanol extract content(%)
G1	海南Hainan	18.87	H1	越南 Vietnam	19.43	S1	马来西亚Malaysia	19.96
G2	海南Hainan	22.41	H2	柬埔寨 Cambodia	21.28	S2	印尼 Indonesia	19.56
G3	海南Hainan	23.23	H3	越南 Vietnam	24.95	S3	西马来西亚 Peninsular Malaysia	24.08
G4	海南Hainan	23.01	H4	缅甸 Myanmar	28.13	S4	加里曼丹Kalimantan	26.20
G5	海南Hainan	25.92	H5	越南 Vietnam	33.94	S5	加里曼丹Kalimantan	31.15
G6	海南Hainan	29.97	H6	越南 Vietnam	38.58	S6	加里曼丹Kalimantan	34.75
G7	海南Hainan	30.30	H7	越南 Vietnam	48.21	S7	西马来西亚 Peninsular Malaysia	34.99
G8	海南Hainan	37.64	H8	越南 Vietnam	48.24	S8	加里曼丹Kalimantan	36.33
G9	海南Hainan	38.27				S9	加里曼丹Kalimantan	43.00
G10	海南Hainan	43.03
G11	广西 Guangxi	2.61

序号 No.	保留时间 Retention time/min	前体离子 [M+H]	分子式 Molecule formula	可能结构 Proposed structure		平均相对峰面积 Average relative area(%)
序号 No.	保留时间 Retention time/min	前体离子 [M+H]	分子式 Molecule formula	A环A ring	B环B ring	国产沉香 Guan-Xiang Zone	惠安系 Hoi-An Zone	星洲系 Sin-Chew Zone
1	11.321	329	C₁₈H₁₆O₆	2 OH	1 OCH₃ 1 OH	0.27	1.03	3.01
2	11.568	329	C₁₈H₁₆O₆	2 OH	1 OCH₃ 1 OH	0.11	0.51	0.02
3	11.783	329	C₁₈H₁₆O₆	2 OH	1 OCH₃ 1 OH	0.16	0.34	0.77
4	12.808	329	C₁₈H₁₆O₆	2 OH	1 OCH₃ 1 OH	0.38	0.80	0.97
5	14.108	343	C₁₉H₁₈O₆	1 OCH₃ 1 OH	1 OCH₃ 1 OH	0.30	0.42	1.00
6	14.418	343	C₁₉H₁₈O₆	1 OCH₃ 1 OH	1 OCH₃ 1 OH	0.69	0.47	2.83
7	14.679	343	C₁₉H₁₈O₆	1 OCH₃ 1 OH	1 OCH₃ 1 OH	1.69	1.12	4.54
8	14.927	313	C₁₈H₁₆O₅	2 OH	1 OCH₃	3.61	6.59	0.12
9	14.983	283	C₁₇H₁₄O₄	2 OH		3.77	0.12	8.87
10	15.169	313	C₁₈H₁₆O₅	1 OH	1 OCH₃ 1 OH	3.30	2.87	5.80
11	15.696	313	C₁₈H₁₆O₅	2 OH	1 OCH₃	2.19	0.09	0.81
12	16.112	329	C₁₈H₁₆O₆	2 OH	1 OCH₃ 1 OH	0.84	2.01	5.00
13	16.881	313	C₁₈H₁₆O₅	2 OH	1 OCH₃	2.98	4.13	1.01
14	17.126	313	C₁₈H₁₆O₅	2 OH	1 OCH₃	5.78	1.86	6.04
15	18.026	297	C₁₈H₁₆O₄	1 OH	1 OCH₃	4.33	1.28	0.02
16	18.304	267	C₁₇H₁₄O₃	1 OH	—	0.11	0.81	0.69
17	19.108	327	C₁₉H₁₈O₅	1 OH 1 OCH₃	1 OCH₃	5.08	5.17	3.95
18	19.356	297	C₁₈H16O₄	1 OH 1 OCH₃	—	6.85	5.88	4.26
19	19.598	297	C₁₈H₁₆O₄	—	1 OH 1 OCH₃	5.47	10.04	1.83
20	20.084	297	C₁₈H₁₆O₄	1 OH	1 OCH₃	6.76	9.53	3.63
21	20.392	267	C₁₇H₁₄O₃ *	6-羟基-2-（2-苯乙基）色酮 6-Hydro-2-(2-phenylethyl) chromone		9.04	5.40	11.78
22	20.822	313	C₁₈H₁₆O₅	2 OH	1 OCH3	3.54	5.64	0.78
23	21.049	283	C₁₇H₁₄O₄	2 OH	—	7.42	3.91	9.25
24	21.697	341	C₂₀H₂₀O₅	2 OCH₃	1 OCH₃	0.93	0.55	0.15
25	22.010	311	C₁₉H₁₈O₄	1 OCH₃	1 OCH₃	3.57	1.27	3.02
26	22.319	283	C₁₇H₁₄O₄	2 OH	—	0.18	0.04	0.02
27	23.221	280	C₁₈H₁₆O₃*	2-[2-（4-甲氧基苯基）乙基]色酮 2-[2-(4-Methoxyphenyl)ethenyl] chromone		1.08	1.07	0.03
28	23.497	250	C₁₇H₁₄O₂*	2-（2-苯乙基）色酮 2-(2-Phenylethyl) chromone		1.84	0.97	1.77
29	24.275	280	C₁₈H₁₆O₃	1 OCH₃	—	0.21	1.34	0.17

Analysis for Characteristic Chemicals of Incense of Burning Agarwood from Three Production Zones

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