Effect of Temperatures on Biosynthesis and Accumulation of Volatiles in Hypericum perforatum

doi:10.11924/j.issn.1000-6850.casb2020-0143

Abstract

Abstract:

The paper aims to unveil the effect of temperatures on biosynthesis and accumulation of VOCs and effectively regulate the biosynthesis of bio-actives constituents in Hypericum perforatum. The ethanol extracts from aerial parts of H. perforatum seedlings at 15, 22 and 30℃ treatments were respectively separated and identified by GS-MS. Total 81 volatiles were identified at the three temperatures, and 37, 39 and 43 compounds were identified at 15, 22 and 30℃, respectively. Comparison of the total peak area showed that the relative content (RC) of total volatiles significantly decreased with the temperatures increase, with a 7% and 21% decrease at 22 and 30℃ compared with that at 15℃, respectively. Comparison of the individual RC found that 23 compounds presented a decrease with the temperatures increase or only existed at 15℃. The constituents and accumulation of VOCs in H. perforatum are significantly affected by temperature, and relative low temperature can enhance the biosynthesis and accumulation of VOCs.

Key words: Hypericum perforatum, temperature, GC-MS, volatile organic compounds, biosynthesis regulation

CLC Number:

Q946.8

Sun Ping, Chen Sijin, Xing Hua, Zhang Zhen, Yao Yuanyuan, Yang Xuezhen, Zhang Xiaona, Li Mengfei. Effect of Temperatures on Biosynthesis and Accumulation of Volatiles in Hypericum perforatum[J]. Chinese Agricultural Science Bulletin, 2021, 37(10): 65-71.

Figures/Tables 4

References 39

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序号	保留时间/ min	挥发性化合物名称	分子式	分子量	15℃		22℃		30℃
序号	保留时间/ min	挥发性化合物名称	分子式	分子量	面积 (×10⁷)	相对含量/%	面积 (×10⁷)	相对含量/%	面积 (×10⁷)	相对含量/%
1	4.26	乙酸	C₂H₄O₂	60	9.01	1.79	/	/	/	/
2	4.46	1,2-Benzenediol, o-(4-ethylbenzoyl)-	C₁₅H₁₄O₃	242	23.01	4.56	48.90	10.41	/	/
3	4.96	2-Propanone, 1,1-diethoxy-	C₇H₁₄O₃	146	3.05	0.60	2.82	0.60	/	/
4	5.07	Ethanone, 2-(formyloxy)-1-phenyl	C₉H₈O₃	164	/	/	/	/	6.83	1.72
5	5.17	Cyclopropanetetradecanoic acid, 2-octyl-, methyl ester	C₂₆H₅₀O₂	394	/	/	/	/	0.85	0.21
6	5.26	Tetraacetyl-d-xylonic nitrile	C₁₄H₁₇NO₉	343	/	/	/	/	0.82	0.21
7	5.47	Propanoic acid, 2-oxo-, methyl ester	C₄H₆O₃	102	/	/	/	/	1.44	0.36
8	5.64	乙醇醛缩二乙醇	C₄H₁₀O₃	106	/	/	/	/	14.28	3.60
9	5.88	3-甲基-3-己醇	C₇H₁₆O	116	/	/	/	/	3.01	0.76
10	5.92	2,3-二羟基丙酸	C₃H₆O₄	106	/	/	/	/	2.70	0.68
11	6.49	Benzoic acid, 4-[1-(3,4-dichlorophenyl)ethylidenaminoxymethyl]-, ethyl ester	C₁₈H₁₇Cl₂NO₃	365	/	/	/	/	0.85	0.21
12	6.59	Acetic acid, 2,2'-[oxybis(2,1-ethanediyloxy)]bis	C₈H₁₄O₇	222	/	/	/	/	1.30	0.33
13	6.71	Ethanol, 2,2-diethoxy-	C₆H₁₄O₃	134	2.02	0.40	1.28	0.27	/	/
14	7.42	N-[3,5-Dinitropyridin-2-yl]proline	C₁₀H₁₀N₄O₆	282	/	/	1.35	0.29	/	/
15	7.44	Benzoic acid, 4-(1,3-dioxolan-2-yl)-, methyl ester	C₁₁H₁₂O₄	208	2.45	0.49	/	/	1.61	0.41
16	8.08	2,4-Dihydroxy-2,5-dimethyl-3(2H)-furan-3-one	C₆H₈O₄	144	/	/	/	/	0.98	0.25
17	8.39	Butanoic acid, 4,4'-dithiobis[2-amino-, [S-(R^,R^)]-	C₈H₁₆N₂O₄S₂	268	/	/	1.65	0.35	/	/
18	10.26	2-仲丁基-4,6-二硝基苯基-3-甲基丁烯酸酯	C₁₅H₁₈N₂O₆	322	3.14	0.62	3.49	0.74	/	/
19	11.23	磷酸三乙酯	C₆H₁₅O₄P	182	18.74	3.71	12.45	2.65	/	/
20	11.36	磷酸二乙酯	C₁₂H₂₇O₄P	266	/	/	/	/	16.81	4.24
21	11.69	4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl-	C₆H₈O₄	144	/	/	2.83	0.60	2.02	0.51
22	12.25	10,13-Octadecadiynoic acid, methyl ester	C₁₉H₃₀O₂	290	/	/	/	/	2.29	0.58
23	13.46	9-Octadecenoic acid, (2-phenyl-1,3-dioxolan-4-yl)methyl ester, cis	C₂₈H₄₄O₄	444	/	/	/	/	2.66	0.67
24	13.63	3,4-二甲基苯甲醛	C₉H₁₀O	134	3.59	0.71	/	/	2.91	0.73
25	13.91	5-羟甲基糠醛	C₆H₆O₃	126	14.58	2.89	6.67	1.42	/	/
26	14.05	2-氨基-4-甲氧基苯酚	C₇H₉NO₂	139	/	/	2.99	0.64	/	/
27	14.07	2-Oxa-6-azatricyclo[3.3.1.1(3,7)]decane	C₈H₁₃NO	139	/	/	/	/	5.33	1.34
28	14.34	2-Cyclohexylpiperidine	C₁₁H₂₁N	167	7.76	1.54	/	/	/	/
29	14.38	谷氨酰胺	C₅H₁₀N₂O₃	146	/	/	9.53	2.03	19.58	4.94
30	14.72	1H-Pyrrole-2,5-dione, 3-ethenyl-4-methyl-	C₇H₇NO₂	137	/	/	5.06	1.08	/	/
31	14.76	Ingol 12-acetate	C₂₂H₃₂O₇	408	/	/	/	/	2.91	0.73
32	15.76	异胆酸乙酯	C₂₆H₄₄O₅	436	7.21	1.43	0.89	0.19	/	/
33	20.33	2-十六醇	C₁₆H₃₄O	242	/	/	1.16	0.25	/	/
34	20.92	Octadecane, 1,1'-[1,3-propanediylbis(oxy)]bis	C₃₉H₈₀O₂	580	/	/	/	/	7.23	1.82
35	21.22	2,4-二叔丁基苯酚	C₁₄H₂₂O	206	/	/	/	/	28.58	7.20
36	21.28	Phenol, 2,6-bis(1,1-dimethylethyl)-	C₁₄H₂₂O	206	60.85	12.06	46.70	9.94	7.84	1.98
37	24.83	6-马来酰亚胺基己酸	C₁₀H₁₃NO₄	211	8.05	1.60	/	/	/	/
38	26.07	1,7-二异丙基萘	C₁₆H₂₀	212	/	/	8.62	1.84	/	/
39	26.11	1,4-二异丙基萘	C₁₆H₂₀	212	7.70	1.53	/	/	/	/
40	27.10	6-Hydroxy-4,4,7a-trimethyl- 5,6,7,7a-tetrahydrobenzofuran-2(4H)-one	C₁₁H₁₆O₃	196	2.28	0.45	1.03	0.22	/	/
41	27.35	Phenol, 2-(1,1-dimethylethyl)-4-(1-methyl-1-phenylethyl)-	C₁₉H₂₄O	268	/	/	9.67	2.06	/	/
42	28.53	新植二烯	C₂₀H₃₈	278	23.24	4.61	17.93	3.82	11.25	2.84
43	29.04	Ethanol, 2-(9-octadecenyloxy)-, (Z)-	C₂₀H₄₀O₂	312	/	/	2.14	0.46	/	/
44	29.04	Cyclopropanenonanoic acid, 2-[(2-butylcyclopropyl)methyl]-, methyl ester	C₂₁H₃₈O₂	322	4.40	0.87	/	/	/	/
45	29.05	Z,Z-3,15-Octadecadien-1-ol acetate	C₂₀H₃₆O₂	308	/	/	/	/	1.62	0.41
46	29.34	Hexadecane, 1,1-bis(dodecyloxy)-	C₄₀H₈₂O₂	594	8.83	1.75	/	/	/	/
47	29.34	5-十八烯醛	C₁₈H₃₄O	266	/	/	2.60	0.55	/	/
48	29.41	9-Hexadecenoic acid, 9-octadecenyl ester, (Z,Z)	C₃₄H₆₄O₂	504	/	/	/	/	5.49	1.38
49	30.92	十六烷酸	C₁₆H₃₂O₂	256	/	/	/	/	3.69	0.93
50	31.45	十六酸乙酯	C₁₈H₃₆O₂	284	10.37	2.05	7.58	1.61	3.29	0.83
51	33.64	叶绿醇	C₂₀H₄₀O	296	8.61	1.71	7.05	1.50	11.04	2.78
52	33.77	9,12-Octadecadienoic acid (Z,Z)-, 2,3-dihydroxypropyl ester	C₂₁H₃₈O₄	354	/	/	4.91	1.05	/	/
53	34.18	Octadecane, 3-ethyl-5-(2-ethylbutyl)	C₂₆H₅₄	366	15.92	3.16	3.39	0.72	/	/
54	34.30	Octadecanal, 2-bromo-	C₁₈H₃₅BrO	346	/	/	2.81	0.60	/	/
55	34.44	亚油酸乙酯	C₂₀H₃₆O₂	308	4.14	0.82	/	/	2.42	0.61
56	34.55	9,12,15-Octadecatrienoic acid, 2,3-dihydroxypropyl ester, (Z,Z,Z)-	C₂₁H₃₆O₄	352	6.25	1.24	7.11	1.51	6.37	1.61
57	34.81	17.alfa.,21β-28,30-Bisnorhopane	C₂₈H₄₈	384	/	/	2.97	0.63	/	/
58	35.26	1-Heptatriacotanol	C₃₇H₇₆O	536	1.76	0.35	1.80	0.38	/	/
59	35.89	Oxiraneoctanoic acid, 3-octyl-, cis-	C₁₈H₃₄O₃	298	2.88	0.57	/	/	/	/
60	35.91	Tricyclo[20.8.0.0(7,16)]triacontane, 1(22),7(16)-diepoxy	C₃₀H₅₂O₂	444	/	/	/	/	1.36	0.34
61	36.54	Docosanoic acid, 1,2,3-propanetriyl ester	C₆₉H₁₃₄O₆	1058	2.43	0.48	/	/	/	/
62	37.99	2-Nonadecanone 2,4-dinitrophenylhydrazine	C₂₅H₄₂N₄O₄	462	/	/	2.68	0.57	1.38	0.35
63	39.48	Hexadecanoic acid, 1-(hydroxymethyl)-1,2-ethanediyl ester	C₃₅H₆₈O₅	568	12.27	2.43	/	/	/	/
64	40.13	紫松果黄素	C₄₀H₅₀O₂	562	/	/	1.43	0.30	3.45	0.87
65	40.57	Phenol, 4,4'-methylenebis[2,6-bis(1,1-dimethylethyl)	C₂₉H₄₄O₂	424	/	/	20.82	4.43	20.46	5.16
66	40.86	Propanoic acid, 2-(3-acetoxy-4,4,14-trimethylandrost-8-en-17-yl)-	C₂₇H₄₂O₄	430	58.87	11.67	53.77	11.45	74.29	18.73
67	42.71	岩藻黄素	C₄₂H₅₈O₆	658	/	/	3.85	0.82	/	/
68	43.13	7,8-Epoxylanostan-11-ol, 3-acetoxy-	C₃₂H₅₄O₄	502	4.30	0.85	4.03	0.86	/	/
69	44.42	Olean-12-ene-3,15,16,21,22,28-hexol, (3β,15α,16α,21β,22α)-	C₃₀H₅₀O₆	506	/	/	23.86	5.08	/	/
70	44.90	Stigmasta-5,24(28)-dien-3-ol, (3β)	C₂₉H₄₈O	412	/	/	4.62	0.98	/	/
71	45.98	3Beta,17beta-diacetoxy-5-chloro-6beta-nitro- 5alpha-androstane	C₂₃H₃₄ClNO₆	455	7.17	1.42	/	/	/	/
72	45.99	3,19:7,8-Diepoxyandrostane, 17-acetoxy-3-methoxy-4,4,7-trimethyl	C₂₅H₃₈O₅	418	/	/	/	/	6.03	1.52
73	47.13	视紫红质	C₄₀H₅₈O	554	10.54	2.09	/	/	/	/
74	47.20	白桦脂醇	C₃₀H₅₀O₂	442	/	/	/	/	11.54	2.91
75	48.52	豆甾醇	C₂₉H₄₈O	412	18.20	3.61	38.95	8.29	13.29	3.35
76	48.90	油酸二十烷基酯	C₃₈H₇₄O₂	562	9.83	1.95	/	/	16.60	4.19
77	49.17	9-Desoxo-9-x-acetoxy-3,8,12-tri-O-acetylingol	C₂₈H₄₀O₁₀	536	41.64	8.25	/	/	6.93	1.75
78	49.31	γ-谷甾醇	C₂₉H₅₀O	414	67.34	13.35	88.24	18.79	43.23	10.90
79	49.55	Stigmasta-5,24(28)-dien-3-ol, (3β)-	C₂₉H₄₈O	412	4.64	0.92	/	/	5.95	1.50
80	50.28	9-Desoxy-9x-chloroingol 3,7,8,12-tetraacetate	C₂₈H₃₉ClO₉	554	/	/	/	/	14.16	3.57
81	50.30	(5,6,7-Triacetoxy-4b,8-dimethyl- 2-oxo-tetradecahydro-phenanthren-1-yl)-acetic acid, methyl ester	C₂₅H₃₆O₉	480	7.37	1.46	/	/	/	/

序号	保留时间/ min	挥发性化合物名称	分子式	分子量	15℃		22℃		30℃
序号	保留时间/ min	挥发性化合物名称	分子式	分子量	面积 (×10⁷)	相对含量/%	面积 (×10⁷)	相对含量/%	面积 (×10⁷)	相对含量/%
1	4.26	乙酸	C₂H₄O₂	60	9.01	1.79	/	/	/	/
2	4.46	1,2-Benzenediol, o-(4-ethylbenzoyl)-	C₁₅H₁₄O₃	242	23.01	4.56	48.90	10.41	/	/
3	4.96	2-Propanone, 1,1-diethoxy-	C₇H₁₄O₃	146	3.05	0.60	2.82	0.60	/	/
4	5.07	Ethanone, 2-(formyloxy)-1-phenyl	C₉H₈O₃	164	/	/	/	/	6.83	1.72
5	5.17	Cyclopropanetetradecanoic acid, 2-octyl-, methyl ester	C₂₆H₅₀O₂	394	/	/	/	/	0.85	0.21
6	5.26	Tetraacetyl-d-xylonic nitrile	C₁₄H₁₇NO₉	343	/	/	/	/	0.82	0.21
7	5.47	Propanoic acid, 2-oxo-, methyl ester	C₄H₆O₃	102	/	/	/	/	1.44	0.36
8	5.64	乙醇醛缩二乙醇	C₄H₁₀O₃	106	/	/	/	/	14.28	3.60
9	5.88	3-甲基-3-己醇	C₇H₁₆O	116	/	/	/	/	3.01	0.76
10	5.92	2,3-二羟基丙酸	C₃H₆O₄	106	/	/	/	/	2.70	0.68
11	6.49	Benzoic acid, 4-[1-(3,4-dichlorophenyl)ethylidenaminoxymethyl]-, ethyl ester	C₁₈H₁₇Cl₂NO₃	365	/	/	/	/	0.85	0.21
12	6.59	Acetic acid, 2,2'-[oxybis(2,1-ethanediyloxy)]bis	C₈H₁₄O₇	222	/	/	/	/	1.30	0.33
13	6.71	Ethanol, 2,2-diethoxy-	C₆H₁₄O₃	134	2.02	0.40	1.28	0.27	/	/
14	7.42	N-[3,5-Dinitropyridin-2-yl]proline	C₁₀H₁₀N₄O₆	282	/	/	1.35	0.29	/	/
15	7.44	Benzoic acid, 4-(1,3-dioxolan-2-yl)-, methyl ester	C₁₁H₁₂O₄	208	2.45	0.49	/	/	1.61	0.41
16	8.08	2,4-Dihydroxy-2,5-dimethyl-3(2H)-furan-3-one	C₆H₈O₄	144	/	/	/	/	0.98	0.25
17	8.39	Butanoic acid, 4,4'-dithiobis[2-amino-, [S-(R^,R^)]-	C₈H₁₆N₂O₄S₂	268	/	/	1.65	0.35	/	/
18	10.26	2-仲丁基-4,6-二硝基苯基-3-甲基丁烯酸酯	C₁₅H₁₈N₂O₆	322	3.14	0.62	3.49	0.74	/	/
19	11.23	磷酸三乙酯	C₆H₁₅O₄P	182	18.74	3.71	12.45	2.65	/	/
20	11.36	磷酸二乙酯	C₁₂H₂₇O₄P	266	/	/	/	/	16.81	4.24
21	11.69	4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl-	C₆H₈O₄	144	/	/	2.83	0.60	2.02	0.51
22	12.25	10,13-Octadecadiynoic acid, methyl ester	C₁₉H₃₀O₂	290	/	/	/	/	2.29	0.58
23	13.46	9-Octadecenoic acid, (2-phenyl-1,3-dioxolan-4-yl)methyl ester, cis	C₂₈H₄₄O₄	444	/	/	/	/	2.66	0.67
24	13.63	3,4-二甲基苯甲醛	C₉H₁₀O	134	3.59	0.71	/	/	2.91	0.73
25	13.91	5-羟甲基糠醛	C₆H₆O₃	126	14.58	2.89	6.67	1.42	/	/
26	14.05	2-氨基-4-甲氧基苯酚	C₇H₉NO₂	139	/	/	2.99	0.64	/	/
27	14.07	2-Oxa-6-azatricyclo[3.3.1.1(3,7)]decane	C₈H₁₃NO	139	/	/	/	/	5.33	1.34
28	14.34	2-Cyclohexylpiperidine	C₁₁H₂₁N	167	7.76	1.54	/	/	/	/
29	14.38	谷氨酰胺	C₅H₁₀N₂O₃	146	/	/	9.53	2.03	19.58	4.94
30	14.72	1H-Pyrrole-2,5-dione, 3-ethenyl-4-methyl-	C₇H₇NO₂	137	/	/	5.06	1.08	/	/
31	14.76	Ingol 12-acetate	C₂₂H₃₂O₇	408	/	/	/	/	2.91	0.73
32	15.76	异胆酸乙酯	C₂₆H₄₄O₅	436	7.21	1.43	0.89	0.19	/	/
33	20.33	2-十六醇	C₁₆H₃₄O	242	/	/	1.16	0.25	/	/
34	20.92	Octadecane, 1,1'-[1,3-propanediylbis(oxy)]bis	C₃₉H₈₀O₂	580	/	/	/	/	7.23	1.82
35	21.22	2,4-二叔丁基苯酚	C₁₄H₂₂O	206	/	/	/	/	28.58	7.20
36	21.28	Phenol, 2,6-bis(1,1-dimethylethyl)-	C₁₄H₂₂O	206	60.85	12.06	46.70	9.94	7.84	1.98
37	24.83	6-马来酰亚胺基己酸	C₁₀H₁₃NO₄	211	8.05	1.60	/	/	/	/
38	26.07	1,7-二异丙基萘	C₁₆H₂₀	212	/	/	8.62	1.84	/	/
39	26.11	1,4-二异丙基萘	C₁₆H₂₀	212	7.70	1.53	/	/	/	/
40	27.10	6-Hydroxy-4,4,7a-trimethyl- 5,6,7,7a-tetrahydrobenzofuran-2(4H)-one	C₁₁H₁₆O₃	196	2.28	0.45	1.03	0.22	/	/
41	27.35	Phenol, 2-(1,1-dimethylethyl)-4-(1-methyl-1-phenylethyl)-	C₁₉H₂₄O	268	/	/	9.67	2.06	/	/
42	28.53	新植二烯	C₂₀H₃₈	278	23.24	4.61	17.93	3.82	11.25	2.84
43	29.04	Ethanol, 2-(9-octadecenyloxy)-, (Z)-	C₂₀H₄₀O₂	312	/	/	2.14	0.46	/	/
44	29.04	Cyclopropanenonanoic acid, 2-[(2-butylcyclopropyl)methyl]-, methyl ester	C₂₁H₃₈O₂	322	4.40	0.87	/	/	/	/
45	29.05	Z,Z-3,15-Octadecadien-1-ol acetate	C₂₀H₃₆O₂	308	/	/	/	/	1.62	0.41
46	29.34	Hexadecane, 1,1-bis(dodecyloxy)-	C₄₀H₈₂O₂	594	8.83	1.75	/	/	/	/
47	29.34	5-十八烯醛	C₁₈H₃₄O	266	/	/	2.60	0.55	/	/
48	29.41	9-Hexadecenoic acid, 9-octadecenyl ester, (Z,Z)	C₃₄H₆₄O₂	504	/	/	/	/	5.49	1.38
49	30.92	十六烷酸	C₁₆H₃₂O₂	256	/	/	/	/	3.69	0.93
50	31.45	十六酸乙酯	C₁₈H₃₆O₂	284	10.37	2.05	7.58	1.61	3.29	0.83
51	33.64	叶绿醇	C₂₀H₄₀O	296	8.61	1.71	7.05	1.50	11.04	2.78
52	33.77	9,12-Octadecadienoic acid (Z,Z)-, 2,3-dihydroxypropyl ester	C₂₁H₃₈O₄	354	/	/	4.91	1.05	/	/
53	34.18	Octadecane, 3-ethyl-5-(2-ethylbutyl)	C₂₆H₅₄	366	15.92	3.16	3.39	0.72	/	/
54	34.30	Octadecanal, 2-bromo-	C₁₈H₃₅BrO	346	/	/	2.81	0.60	/	/
55	34.44	亚油酸乙酯	C₂₀H₃₆O₂	308	4.14	0.82	/	/	2.42	0.61
56	34.55	9,12,15-Octadecatrienoic acid, 2,3-dihydroxypropyl ester, (Z,Z,Z)-	C₂₁H₃₆O₄	352	6.25	1.24	7.11	1.51	6.37	1.61
57	34.81	17.alfa.,21β-28,30-Bisnorhopane	C₂₈H₄₈	384	/	/	2.97	0.63	/	/
58	35.26	1-Heptatriacotanol	C₃₇H₇₆O	536	1.76	0.35	1.80	0.38	/	/
59	35.89	Oxiraneoctanoic acid, 3-octyl-, cis-	C₁₈H₃₄O₃	298	2.88	0.57	/	/	/	/
60	35.91	Tricyclo[20.8.0.0(7,16)]triacontane, 1(22),7(16)-diepoxy	C₃₀H₅₂O₂	444	/	/	/	/	1.36	0.34
61	36.54	Docosanoic acid, 1,2,3-propanetriyl ester	C₆₉H₁₃₄O₆	1058	2.43	0.48	/	/	/	/
62	37.99	2-Nonadecanone 2,4-dinitrophenylhydrazine	C₂₅H₄₂N₄O₄	462	/	/	2.68	0.57	1.38	0.35
63	39.48	Hexadecanoic acid, 1-(hydroxymethyl)-1,2-ethanediyl ester	C₃₅H₆₈O₅	568	12.27	2.43	/	/	/	/
64	40.13	紫松果黄素	C₄₀H₅₀O₂	562	/	/	1.43	0.30	3.45	0.87
65	40.57	Phenol, 4,4'-methylenebis[2,6-bis(1,1-dimethylethyl)	C₂₉H₄₄O₂	424	/	/	20.82	4.43	20.46	5.16
66	40.86	Propanoic acid, 2-(3-acetoxy-4,4,14-trimethylandrost-8-en-17-yl)-	C₂₇H₄₂O₄	430	58.87	11.67	53.77	11.45	74.29	18.73
67	42.71	岩藻黄素	C₄₂H₅₈O₆	658	/	/	3.85	0.82	/	/
68	43.13	7,8-Epoxylanostan-11-ol, 3-acetoxy-	C₃₂H₅₄O₄	502	4.30	0.85	4.03	0.86	/	/
69	44.42	Olean-12-ene-3,15,16,21,22,28-hexol, (3β,15α,16α,21β,22α)-	C₃₀H₅₀O₆	506	/	/	23.86	5.08	/	/
70	44.90	Stigmasta-5,24(28)-dien-3-ol, (3β)	C₂₉H₄₈O	412	/	/	4.62	0.98	/	/
71	45.98	3Beta,17beta-diacetoxy-5-chloro-6beta-nitro- 5alpha-androstane	C₂₃H₃₄ClNO₆	455	7.17	1.42	/	/	/	/
72	45.99	3,19:7,8-Diepoxyandrostane, 17-acetoxy-3-methoxy-4,4,7-trimethyl	C₂₅H₃₈O₅	418	/	/	/	/	6.03	1.52
73	47.13	视紫红质	C₄₀H₅₈O	554	10.54	2.09	/	/	/	/
74	47.20	白桦脂醇	C₃₀H₅₀O₂	442	/	/	/	/	11.54	2.91
75	48.52	豆甾醇	C₂₉H₄₈O	412	18.20	3.61	38.95	8.29	13.29	3.35
76	48.90	油酸二十烷基酯	C₃₈H₇₄O₂	562	9.83	1.95	/	/	16.60	4.19
77	49.17	9-Desoxo-9-x-acetoxy-3,8,12-tri-O-acetylingol	C₂₈H₄₀O₁₀	536	41.64	8.25	/	/	6.93	1.75
78	49.31	γ-谷甾醇	C₂₉H₅₀O	414	67.34	13.35	88.24	18.79	43.23	10.90
79	49.55	Stigmasta-5,24(28)-dien-3-ol, (3β)-	C₂₉H₄₈O	412	4.64	0.92	/	/	5.95	1.50
80	50.28	9-Desoxy-9x-chloroingol 3,7,8,12-tetraacetate	C₂₈H₃₉ClO₉	554	/	/	/	/	14.16	3.57
81	50.30	(5,6,7-Triacetoxy-4b,8-dimethyl- 2-oxo-tetradecahydro-phenanthren-1-yl)-acetic acid, methyl ester	C₂₅H₃₆O₉	480	7.37	1.46	/	/	/	/