Comprehensive chemical profiling of volatile constituents of Angong Niuhuang Pill in vitro and in vivo based on gas chromatography coupled with mass spectrometry

Jiang, Yue; Li, Jie; Ding, Meng; Guo, Zi-Fan; Yang, Hua; Li, Hui-Jun; Gao, Wen; Li, Ping

doi:10.1186/s13020-022-00659-8

Table 1 Identification of the chemical constituents in the essential oil of ANP by GC–MS

From: Comprehensive chemical profiling of volatile constituents of Angong Niuhuang Pill in vitro and in vivo based on gas chromatography coupled with mass spectrometry

No.	t_R (min)	Compound	Formula	CAS	RI (measured)	RI (NIST)	Match	Structure type	Source
1	10.53	Tricyclene	C₁₀H₁₆	508-32-7	930.02	925	853	Monoterpeneoids	B
2	10.79	α-Pinene^a	C₁₀H₁₆	80-56-8	939.35	937	872	Monoterpeneoids	GF, CR
3	11.32	Camphene^a	C₁₀H₁₆	79-92-5	958.17	952	954	Monoterpeneoids	B, CR
4	11.59	Benzaldehyde^a	C₇H₆O	100-52-7	967.74	962	951	Aldehydes	GF
5	12.13	β-Pinene^a	C₁₀H₁₆	127-91-3	987.29	979	847	Monoterpeneoids	CR
6	12.25	2-Pentylfuran	C₉H₁₄O	3777-69-3	991.45	993	839	Furans	GF
7	12.32	2,2,4,6,6-Pentamethylheptane	C₁₂H₂₆	13475-82-6	993.74	991	897	Alkanes	B
8	12.95	α-Phellandrene	C₁₀H₁₆	99-83-2	1012.46	1005	906	Monoterpeneoids	CR
9	13.05	(+)-3-Carene^a	C₁₀H₁₆	498-15-7	1015.16	1010	740	Monoterpeneoids	CR
10	13.29	α-Terpinene^a	C₁₀H₁₆	99-86-5	1021.92	1017	825	Monoterpeneoids	CR
11	13.54	p-Cymene	C₁₀H₁₄	99-87-6	1028.7	1025	900	Monoterpeneoids	GF, CR
12	13.72	Limonene^a	C₁₀H₁₆	138-86-3	1033.6	1030	836	Monoterpeneoids	GF, CR
13	13.9	Eucalyptol^a	C₁₀H₁₈O	470-82-6	1038.53	1032	934	Monoterpeneoids	GF, CR
14	14.09	β-Isophorone	C₉H₁₄O	471-01-2	1043.5	1044	843	Ketones	GF
15	14.22	Benzeneacetaldehyde^a	C₈H₈O	122-78-1	1047.2	1045	935	Aldehydes	GF
16	14.73	r-Terpinene	C₁₀H₁₆	99-85-4	1061.04	1060	733	Monoterpeneoids	CR
17	15.07	Acetophenone^a	C₈H₈O	98-86-2	1070.44	1065	965	Ketones	GF
18	15.83	Terpinolene^a	C₁₀H₁₆	586-62-9	1090.9	1088	935	Monoterpeneoids	CR
19	16.01	p-Cymenene	C₁₀H₁₂	1195-32-0	1095.82	1090	843	Monoterpeneoids	CR
20	16.1	Fenchone	C₁₀H₁₆O	1195-79-5	1098.36	1096	810	Monoterpeneoids	B
21	16.39	Nonanal	C₉H₁₈O	124-19-6	1105.11	1104	872	Aldehydes	GF
22	17.15	Isofenchol	C₁₀H₁₈O	6168-62-3	1121.75	–	918	Monoterpeneoids	B
23	17.37	Fenchol^a	C₁₀H₁₈O	1632-73-1	1126.45	1113	904	Monoterpeneoids	B
24	17.61	β-Fenchol	C₁₀H₁₈O	22627-95-8	1131.74	1116	848	Monoterpeneoids	B
25	17.98	α-Campholenal	C₁₀H₁₆O	4501-58-0	1140.03	1125	828	Monoterpeneoids	B
26	18.74	Camphor^a	C₁₀H₁₆O	76-22-2	1156.5	1145	930	Monoterpeneoids	B
27	19.12	Camphene hydrate	C₁₀H₁₈O	465-31-6	1164.88	1148	925	Monoterpeneoids	B
28	19.67	Isoborneol^a	C₁₀H₁₈O	124-76-5	1177.11	1157	976	Monoterpeneoids	B
29	20.17	d-Borneol^a	C₁₀H₁₈O	464-43-7	1188.07	1167	963	Monoterpeneoids	B
30	20.39	α,α,3-Trimethylbenzenemethanol	C₁₀H₁₄O	5208-37-7	1192.7	1180	845	Alcohols	CR
31	20.83	l-α-Terpineol	C₁₀H₁₈O	10482-56-1	1202.58	1190	819	Monoterpeneoids	GF, CR
32	21.11	2-Bornanol	C₁₀H₁₈O	10,385-78-1	1207.45	–	811	Monoterpeneoids	B
33	21.3	Neoisopulegol	C₁₀H₁₈O	29141-10-4	1211.19	–	813	Monoterpeneoids	B
34	22.22	4-Methyleneisophorone	C₁₀H₁₄O	20548-00-9	1229.01	1242	952	Ketones	GF
35	22.64	Bornyl formate	C₁₁H₁₈O₂	7492-41-3	1236.94	1226	908	Monoterpeneoids	B
36	23.08	Isobornyl formate	C₁₁H₁₈O₂	1200-67-5	1245.47	1232	818	Monoterpeneoids	B
37	25.41	l-Bornyl acetate	C₁₂H₂₀O₂	5655-61-8	1290.31	1284	640	Monoterpeneoids	B
38	26.55	4-Vinylguaiacol	C₉H₁₀O₂	7786-61-0	1314.47	1317	932	Phenols	CR
39	28.45	Eugenol	C₁₀H₁₂O₂	97-53-0	1357.5	1357	819	Phenols	GF
40	28.76	Benzalacetone	C₁₀H₁₀O	122-57-6	1364.59	–	865	Ketones	GF
41	29.56	4-Methyl-4-phenyl-2-pentanone^a	C₁₂H₁₆O	7403-42-1	1382.7	–	769	Ketones	CR
42	31.52	β-Caryophyllene^a	C₁₅H₂₄	87-44-5	1429.53	1419	932	Sesquiterpenoids	CR
43	32.13	Paeonol	C₉H₁₀O₃	552-41-0	1444.74	1438	914	Phenols	GF
44	32.44	trans-β-Farnesene	C₁₅H₂₄	18794-84-8	1452.39	1457	796	Sesquiterpenoids	CR
45	32.61	Sesquisabinene	C₁₅H₂₄	58319-04-3	1456.51	1464	811	Sesquiterpenoids	CR
46	32.98	Humulene^a	C₁₅H₂₄	6753-98-6	1465.58	1454	804	Sesquiterpenoids	CR
47	33.65	1,3-Cyclohexadiene, 1-(1,5-dimethyl-4-hexenyl)-4-methyl-	C₁₅H₂₄	451-55-8	1482.09	1480	876	Sesquiterpenoids	CR
48	33.77	α-Curcumene^a	C₁₅H₂₂	644-30-4	1485.18	1483	957	Sesquiterpenoids	CR
49	34.32	α-Zingiberene	C₁₅H₂₄	495-60-3	1498.67	1495	891	Sesquiterpenoids	CR
50	34.57	α-Farnesene	C₁₅H₂₄	502-61-4	1505.36	1508	672	Sesquiterpenoids	CR
51	34.84	β-Bisabolene	C₁₅H₂₄	495-61-4	1513.02	1509	919	Sesquiterpenoids	CR
52	35.15	Ethylparaben	C₉H₁₀O₃	120–47-8	1521.51	–	910	Benzoate esters	M
53	35.49	β-Sesquiphellandrene	C₁₅H₂₄	20307-83-9	1530.9	1524	929	Sesquiterpenoids	CR
54	35.61	trans-γ-Bisabolene	C₁₅H₂₄	53585-13-0	1534.09	1533	833	Sesquiterpenoids	CR
55	36.59	cis-Sesquisabinene hydrate	C₁₅H₂₆O	58319-05-4	1561.06	1543	857	Sesquiterpenoids	CR
56	36.72	trans-Nerolidol	C₁₅H₂₆O	40716-66-3	1564.79	1564	750	Sesquiterpenoids	CR
57	37.39	ar-Tumerol	C₁₅H₂₂O	38142-57-3	1583.26	1583	792	Sesquiterpenoids	CR
58	37.86	trans-Sesquisabinene hydrate	C₁₅H₂₆O	145,512–84-1	1596.08	1581	900	Sesquiterpenoids	CR
59	38.64	Zingiberenol	C₁₅H₂₆O	58334-55-7	1620.64	1616	923	Sesquiterpenoids	CR
60	38.85	trans-Nuciferol	C₁₅H₂₂O	39599-18-3	1627.39	–	712	Sesquiterpenoids	CR
61	39.18	β-Acorenol	C₁₅H₂₆O	28400-11-5	1637.839241	1649	808	Sesquiterpenoids	CR
62	40.16	ar-Tumerone^a	C₁₅H₂₀O	532-65-0	1669.3	1664	949	Sesquiterpenoids	CR
63	40.33	Tumerone	C₁₅H₂₂O	180315-67-7	1674.84	1632	935	Sesquiterpenoids	CR
64	40.44	(Z)-γ-Atlantone	C₁₅H₂₂O	108549-48-0	1678.45	1699	836	Sesquiterpenoids	CR
65	41	4-(1,5-Dimethylhex-4-enyl)cyclohex-2-enone	C₁₄H₂₂O	1723-80-4	1696.24	1698	848	Sesquiterpenoids	CR
66	41.24	Bisacurol	C₁₅H₂₄O	120681-80-3	1704.32	–	910	Sesquiterpenoids	CR
67	41.4	Curlone	C₁₅H₂₂O	82508-14-3	1709.55	–	948	Sesquiterpenoids	CR
68	41.61	Curcuphenol	C₁₅H₂₂O	69301-27-5	1716.86	1717	814	Sesquiterpenoids	CR
69	41.7	(Z)-α-Atlantone	C₁₅H₂₂O	56192-70-2	1719.91	1717	915	Sesquiterpenoids	CR
70	42.71	(6R,7R)-Bisabolone	C₁₅H₂₄O	72441-71-5	1754.45	1747	936	Sesquiterpenoids	CR
71	42.82	Tetradecanoic acid	C₁₄H₂₈O₂	544-63-8	1758.18	1768	780	Fatty acids and their esters	GF
72	43.55	(−)-(E)-α-Atlantone	C₁₅H₂₂O	108645-54-1	1783.13	1773	927	Sesquiterpenoids	CR
73	43.85	Ethyl myristate	C₁₆H₃₂O₂	124-06-1	1793.15	1794	665	Fatty acids and their esters	GF
74	44.39	Turmeronol B	C₁₅H₂₀O₂	131651-38-2	1815.66	–	763	Sesquiterpenoids	CR
75	45.5	Muscone^a	C₁₆H₃₀O	541-91-3	1867.53	–	929	Ketones	M
76	46.64	Methyl palmitate	C₁₇H₃₄O₂	112-39-0	1925.78	1926	868	Fatty acids and their esters	M, GF
77	47.23	Palmitic acid	C₁₆H₃₂O₂	10/3/1957	1960.36	1968	957	Fatty acids and their esters	M, GF
78	47.78	Ethyl palmitate	C₁₈H₃₆O₂	628-97-7	1992.48	1993	915	Fatty acids and their esters	B, M, GF, CR
79	49.25	Methyl linoleate	C₁₉H₃₄O₂	112-63-0	2094.97	2092	904	Fatty acids and their esters	GF
80	49.33	Methyl oleate	C₁₉H₃₆O₂	112-62-9	2100.76	2091	846	Fatty acids and their esters	M, GF
81	49.72	Linoleic acid	C₁₈H₃₂O₂	60-33-3	2132.12	2133	900	Fatty acids and their esters	M, GF
82	49.79	Oleic acid	C₁₈H₃₄O₂	112–80-1	2138.03	2141	887	Fatty acids and their esters	M, GF
83	50.05	Stearic acid	C₁₈H₃₆O₂	11/4/1957	2159.94	2172	842	Fatty acids and their esters	M, GF
84	50.09	Ethyl linoleate	C₂₀H₃₆O₂	544-35-4	2163.23	2162	937	Fatty acids and their esters	M
85	50.17	Ethyl oleate	C₂₀H₃₈O₂	111-62-6	2169.06	2173	905	Fatty acids and their esters	M
86	50.45	Ethyl stearate	C₂₀H₄₀O₂	111-61-5	2192.34	2195	811	Fatty acids and their esters	B
87	50.54	Docosane	C₂₂H₄₆	629-97-0	2199.89	2200	855	Alkanes	GF
88	51.62	Tricosane	C₂₃H₄₈	638-67-5	2299.86	2300	880	Alkanes	GF
89	52.65	Tetracosane	C₂₄H₅₀	646-31-1	2399.86	2400	886	Alkanes	GF
90	53.72	Pentacosane	C₂₅H₅₂	629-99-2	2499.78	2500	878	Alkanes	GF
91	54.17	Di(2-propylpentyl) phthalate	C₂₄H₃₈O₄	70910-37-1	2538.21	2527	911	Benzoate esters	GF
92	54.89	Hexacocane	C₂₆H₅₄	630-01-3	2599.7	2600	873	Alkanes	GF
93	56.2	Heptacosane	C₂₇H₅₆	593-49-7	2699.46	2700	851	Alkanes	GF

The batch of ANP used for qualification was S7
Sources: B Borneolum, M Moschus, CR Curcumae Radix, GF Gardeniae Fructus
–: The RI was not found in NIST library
^aThe identification was confirmed with reference standards

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ISSN: 1749-8546

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