不同桂花品种游离态香气物质分析

doi:10.16420/j.issn.0513-353x.2021-0773

摘要/Abstract

摘要：

采用甲基叔丁基醚（MTBE）溶剂萃取结合气相色谱—质谱联用法（GC-MS）对20个常见的桂花栽培品种的花瓣进行了游离态香气物质的检测和比较。共鉴定出125种游离态物质，包括萜类、芳香族化合物、烷烃类、醛类、醇类和酯类等，其中萜类物质种类丰富、含量最高，是最主要的香气活性物质。‘玉帘银丝’与‘日香桂’的游离态香气物质总含量较高，‘橘叶四季桂’与‘日香桂’的萜类物质含量较高，是香气浓郁的优良品种。‘小叶朱砂桂’‘满条红’在丹桂品种群中游离态萜类物质含量最高，香气浓郁且不易褐化，是值得推广的特色丹桂品种。‘日香桂’的β-紫罗酮、γ-癸内酯和芳樟醇含量较高，‘橘叶四季桂’的芳樟醇氧化物含量较高，这些物质具有抗菌、镇静、提神等重要保健功能，可作为特色功能品种推广。

关键词: 桂花, 游离态香气物质, 萜类物质, 品种, 溶剂萃取, GC-MS

Abstract:

In this study，methyl tert-butyl ether（MTBE）solvent extraction combined with gas chromatography-mass spectrometry（GC-MS）was applied to detect the free aroma components in petals of 20 common cultivars of Osmanthus fragrans. The results showed that 125 kinds of free components were identified in 20 cultivars，which were significantly more than the corresponding volatile aroma components. The aroma components mainly included terpenoids，benzenoids，alkanes，aldehydes，alcohols and esters. Terpenoids were the dominant aroma active components. Among the 20 cultivars，‘Yulian Yinsi’and‘Rixianggui’contained the maximum contents of free aroma components.‘Juye Sijigui’and‘Rixianggui’contained the high contents of terpenoids and were rich in aroma. Luteus Group generally had low aroma components and hardly tended to browning‘Xiaoye Zhushagui’and‘Mantiaohong’had the highest contents of terpenoids in Luteus Group，thus they were recommended as characteristic cultivars for industrial application.‘Rixianggui’was a potential cultivar because it had considerably high contents of β-ionone，γ-decalactone and linalool.‘Juye Sijigui’was also an ideal cultivar with high contents of linalool oxide.

Key words: Osmanthus fragrans, free aroma components, terpenoids, cultivar, solvent extraction, GC-MS

中图分类号:

S685.13

朱琳琳, 周婉飞, 宁璇, 朱君, 席婉, 曾旭梅, 熊康舜, 王彩云, 罗靖, 郑日如. 不同桂花品种游离态香气物质分析[J]. 园艺学报, 2022, 49(11): 2395-2406.

ZHU Linlin, ZHOU Wanfei, NING Xuan, ZHU Jun, XI Wan, ZENG Xumei, XIONG Kangshun, WANG Caiyun, LUO Jing, ZHENG Riru. Analysis of Free Aromatic Components of Different Osmanthus fragrans Cultivars[J]. Acta Horticulturae Sinica, 2022, 49(11): 2395-2406.

图/表 6

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种类 Type	化合物名称 Name	分子式 Molecular	CAS	保留指数 RI	含量/（μg · g^-1 FW） Content
单萜烯 Monoterpenes	(Z)-3,7-二甲基-1,3,6-辛三烯 1,3,6-Octatriene, 3,7-dimethyl-, (Z)-	C₈H₁₆	3338-55-4	1 038	0.19（0 ~ 2.93）
单萜醇	芳樟醇 Linalool	C₁₀H₁₈O	78-70-6	1 099	7.14（0 ~ 29.61）
Monoterpene alcohols	香叶醇 Geraniol	C₁₀H₁₈O	106-24-1	1 255	1.8（0 ~ 8.25）
	二氢-3-氧代-β-紫罗兰醇 Dihydro-3-oxo-β-ionol	C₁₃H₂₂O₂	27185-79-1	1 726	0.19（0 ~.23）
	去氢吐叶醇(S,E)-4-Hydroxy-3,5,5-trimethyl-4- (3-oxobut-1-en-1-yl)cyclohex-2-enone	C₁₃H₁₈O₃	39763-33-2	1 800	0.16（0 ~ 0.79）
	3,7-二甲基-八-1,5-二烯-3,7-二醇 3,7-Octadiene-2,6-diol, 2,6-dimethyl-	C₁₀H₁₈O₂	13741-21-4	1 190	0.14（0 ~ 2.33）
种类 Type	化合物名称 Name	分子式 Molecular	CAS	保留指数 RI	含量/（μg · g^-1 FW） Content
	8-羟基芳樟醇 8-Hydroxylinalool	C₁₀H₁₈O₂	64142-78-5	1 361	0.04（0 ~ 0.21）
单萜醛	β-环柠檬醛 β-Cyclocitral	C₁₀H₁₆O	432-25-7	1 220	0.03（0 ~ 0.24）
Monoterpene aldehydes	羟基香茅醛 Octanal, 7-hydroxy-3,7-dimethyl-	C₁₀H₂₀O₂	107-75-5	1 300	0.02（0 ~ 0.3）
	橙花醛2,6-Octadienal, 3,7-dimethyl-	C₁₀H₁₆O	141-27-5	1 270	0.01（0 ~ 0.18）
单萜酮	β-紫罗酮 β-Ionone	C₁₃H₂₀O	79-77-6	1 486	15.56（0.25 ~ 29.33）
Monoterpene ketones	α-紫罗酮 α-Ionone	C₁₃H₂₀O	127-41-3	1 426	1.16（0.1 ~ 4.43）
	3-氧-α-紫罗兰酮 3-Oxo-α-ionone	C₁₃H₁₈O₂	79734-43-3	1 670	0.75（0.06 ~ 3）
	二氢-β-紫罗兰酮 Dihydro-β-ionone	C₁₃H₂₂O	17283-81-7	1 433	0.68（0.02 ~ 1.42）
	氧代-7,8-二氢-β-紫罗兰醇 3-Oxo-7,8-dihydro-β-ionol	C₁₃H₂₀O₂	72008-46-9	1 695	0.28（0 ~ 1.34）
	3-氧代-β-紫罗酮 3-Keto-β-ionone	C₁₃H₁₈O₂	27185-77-9	1 661	0.24（0.15 ~ 0.82）
	6-戊基-2H-吡喃-2-酮 6-Amyl-α-pyrone	C₁₀H₁₄O₂	27593-23-3	1 453	0.17（0 ~ 1.27）
	4-羟基-β-紫罗兰酮 4-Hydroxy-β-ionone	C₁₃H₂₀O₂	116296-75-4	—	0.05（0 ~ 1.1）
	(Z)-ψ-紫罗兰酮cis-.psi.-Ionone	C₁₃H₂₀O	13927-47-4	1 535	0.01（0 ~ 0.28）
	茉莉酮trans-Z-à-Bisabolene epoxide	C₁₁H₁₆O	488-10-8	1 394	0.01（0 ~ 0.12）
单萜氧化物 Monoterpene oxides	反式芳樟醇氧化物（呋喃型） trans-Linalool oxide（furanoid）	C₁₀H₁₈O₂	34995-77-2	1 086	7.09（0.11 ~ 21.5）
	顺式芳樟醇氧化物（呋喃型）cis-Furan linalool oxide	C₁₀H₁₈O₂	5989-33-3	1 074	4.39（0.06 ~ 13.91）
	顺式芳樟醇氧化物（吡喃型）cis-Linalool 3,7-oxide	C₁₀H₁₈O₂	14009-71-3	1 174	2.74（0 ~ 7.02）
	芳樟醇氧化物（呋喃型）Linalool oxide（pyranoid）	C₁₀H₁₈O₂	14049-11-7	1 178	1.45（0 ~ 10.02）
	反式芳樟醇氧化物（吡喃型） trans-Linalool 3,7-oxide	C₁₀H₁₈O₂	39028-58-5	1 173	1.05（0 ~ 5.83）
单萜酯 Monoterpene esters	(E)-己-3-烯基丁酸酯 (E)-Butanoic acid, 3-hexenyl ester	C₁₀H₁₈O₂	53398-84-8	1 185	0.04（0 ~ 0.72）
	（Z）-4-己烯基丁酸酯 Butyric acid (Z)-4-hexenyl ester	C₁₀H₁₈O₂	69727-41-9	1 203	0.01（0 ~ 0.15）
倍半萜	α-长叶蒎烯 α-Longipinene	C₁₅H₂₄	5989-08-2	1 353	0.05（0 ~ 0.15）
Sesquiterpenes	异戊酸香叶酯 Geranyl isovalerate	C₁₅H₂₆O₂	109-20-6	1 606	0.05（0 ~ 0.24）
	(-)-异长叶醇 Isolongifolol	C₁₃H₂₂O₂	1139-17-9	1 738	0.03（0 ~ 0.6）
双萜	香叶基芳樟醇 Linalool，geranyl-	C₂₀H₃₄O	1113-21-9	2 034	1.51（0 ~ 14.93）
Diterpenes	异植醇 Isophytol	C₂₀H₄₀O	505-32-8	1 948	0.13（0 ~ 0.95）
芳香族 Benzenoid and derivatives	4A-甲基-4,4a,5,6,7,8-六氢-3H-萘-2-酮 4A-Methyl-3,4,5,6,7,8-hexahydronaphthalen-2-one	C₁₁H₁₆O	826-56-2	—	4.77（0.89 ~ 10.02）
	4-羟基苯乙酸乙酯 Tyrosol, acetate	C₁₀H₁₂O₃	58556-55-1	1 568	3.71（0.61 ~ 12.42）
	2,4-二叔丁基酚 2,4-Di-tert-butylphenol	C₁₄H₂₂O	96-76-4	1 519	2（1.02 ~ 4.1）
	4-羟基-苯乙醇 Benzeneethanol, 4-hydroxy-	C₈H₁₀O₂	501-94-0	1 444	1.24（0.02 ~ 4.76）
	4-甲氧基苯乙醇 2-（4-Methoxyphenyl）ethanol	C₉H₁₂O₂	702-23-8	1 374	0.84（0 ~ 8.66）
	2,2'-亚甲基双-（4-甲基-6-叔丁基苯酚）Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl-	C₂₃H₃₂O₂	119-47-1	2 414	0.49（0.1 ~ 1.25）
	2-羟基-2-甲基-1-苯基-1-丙酮 2-Hydroxy-iso-butyrophenone	C₁₀H₁₂O₂	7473-98-5	1 278	0.32（0.17 ~ 0.65）
	苯甲酸 Benzoic acid	C₇H₆O₂	65-85-0	—	0.28（0 ~ 2.37）
	依杜兰 Edulan	C₁₃H₂₀O	41678-29-9	1 314	0.08（0 ~ 0.45）
	4-羟基苯丙酮 p-Hydroxyphenylacetone	C₉H₁₀O₂	770-39-8	1 483	0.08（0 ~ 0.3）
	2,5-二甲基苯甲醛Benzaldehyde, 2,5-dimethyl-	C₉H₁₀O	5779-94-2	1 208	0.07（0 ~ 0.33）
	苯甲酸异丙酯Benzoic acid, 1-methylethyl ester	C₁₀H₁₂O₂	939-48-0	1 217	0.04（0 ~ 0.75）
	3,3,5,6-四甲基-1,2-二氢茚 Indan, 1,1,4,6-tetramethyl-	C₁₃H₁₈	941-60-6	1 350	0.01（0 ~ 0.16）
	α-甲基-1,4-苯二甲醇 α-methyl-1,4-Benzenedimethanol	C₉H₁₂O₂	80463-22-5	1 417	0.01（0 ~ 0.24）
	丁酸苯乙酯 β-Phenylethyl butyrate	C₁₂H₁₆O₂	103-52-6	1 447	0.01（0 ~ 0.19）
	苯乙醛 α-Tolualdehyde	C₈H₈O	122-78-1	1 045	0（0 ~ 0.06）
	4-羟基苯丙醛 3-（4-Hydroxyphenyl）propanal	C₉H₁₀O₂	20238-83-9	1 490	0（0 ~ 0.07）

种类 Type	化合物名称 Name	分子式 Molecular	CAS	保留指数 RI	含量/（μg · g^-1 FW） Content
单萜烯 Monoterpenes	(Z)-3,7-二甲基-1,3,6-辛三烯 1,3,6-Octatriene, 3,7-dimethyl-, (Z)-	C₈H₁₆	3338-55-4	1 038	0.19（0 ~ 2.93）
单萜醇	芳樟醇 Linalool	C₁₀H₁₈O	78-70-6	1 099	7.14（0 ~ 29.61）
Monoterpene alcohols	香叶醇 Geraniol	C₁₀H₁₈O	106-24-1	1 255	1.8（0 ~ 8.25）
	二氢-3-氧代-β-紫罗兰醇 Dihydro-3-oxo-β-ionol	C₁₃H₂₂O₂	27185-79-1	1 726	0.19（0 ~.23）
	去氢吐叶醇(S,E)-4-Hydroxy-3,5,5-trimethyl-4- (3-oxobut-1-en-1-yl)cyclohex-2-enone	C₁₃H₁₈O₃	39763-33-2	1 800	0.16（0 ~ 0.79）
	3,7-二甲基-八-1,5-二烯-3,7-二醇 3,7-Octadiene-2,6-diol, 2,6-dimethyl-	C₁₀H₁₈O₂	13741-21-4	1 190	0.14（0 ~ 2.33）
种类 Type	化合物名称 Name	分子式 Molecular	CAS	保留指数 RI	含量/（μg · g^-1 FW） Content
	8-羟基芳樟醇 8-Hydroxylinalool	C₁₀H₁₈O₂	64142-78-5	1 361	0.04（0 ~ 0.21）
单萜醛	β-环柠檬醛 β-Cyclocitral	C₁₀H₁₆O	432-25-7	1 220	0.03（0 ~ 0.24）
Monoterpene aldehydes	羟基香茅醛 Octanal, 7-hydroxy-3,7-dimethyl-	C₁₀H₂₀O₂	107-75-5	1 300	0.02（0 ~ 0.3）
	橙花醛2,6-Octadienal, 3,7-dimethyl-	C₁₀H₁₆O	141-27-5	1 270	0.01（0 ~ 0.18）
单萜酮	β-紫罗酮 β-Ionone	C₁₃H₂₀O	79-77-6	1 486	15.56（0.25 ~ 29.33）
Monoterpene ketones	α-紫罗酮 α-Ionone	C₁₃H₂₀O	127-41-3	1 426	1.16（0.1 ~ 4.43）
	3-氧-α-紫罗兰酮 3-Oxo-α-ionone	C₁₃H₁₈O₂	79734-43-3	1 670	0.75（0.06 ~ 3）
	二氢-β-紫罗兰酮 Dihydro-β-ionone	C₁₃H₂₂O	17283-81-7	1 433	0.68（0.02 ~ 1.42）
	氧代-7,8-二氢-β-紫罗兰醇 3-Oxo-7,8-dihydro-β-ionol	C₁₃H₂₀O₂	72008-46-9	1 695	0.28（0 ~ 1.34）
	3-氧代-β-紫罗酮 3-Keto-β-ionone	C₁₃H₁₈O₂	27185-77-9	1 661	0.24（0.15 ~ 0.82）
	6-戊基-2H-吡喃-2-酮 6-Amyl-α-pyrone	C₁₀H₁₄O₂	27593-23-3	1 453	0.17（0 ~ 1.27）
	4-羟基-β-紫罗兰酮 4-Hydroxy-β-ionone	C₁₃H₂₀O₂	116296-75-4	—	0.05（0 ~ 1.1）
	(Z)-ψ-紫罗兰酮cis-.psi.-Ionone	C₁₃H₂₀O	13927-47-4	1 535	0.01（0 ~ 0.28）
	茉莉酮trans-Z-à-Bisabolene epoxide	C₁₁H₁₆O	488-10-8	1 394	0.01（0 ~ 0.12）
单萜氧化物 Monoterpene oxides	反式芳樟醇氧化物（呋喃型） trans-Linalool oxide（furanoid）	C₁₀H₁₈O₂	34995-77-2	1 086	7.09（0.11 ~ 21.5）
	顺式芳樟醇氧化物（呋喃型）cis-Furan linalool oxide	C₁₀H₁₈O₂	5989-33-3	1 074	4.39（0.06 ~ 13.91）
	顺式芳樟醇氧化物（吡喃型）cis-Linalool 3,7-oxide	C₁₀H₁₈O₂	14009-71-3	1 174	2.74（0 ~ 7.02）
	芳樟醇氧化物（呋喃型）Linalool oxide（pyranoid）	C₁₀H₁₈O₂	14049-11-7	1 178	1.45（0 ~ 10.02）
	反式芳樟醇氧化物（吡喃型） trans-Linalool 3,7-oxide	C₁₀H₁₈O₂	39028-58-5	1 173	1.05（0 ~ 5.83）
单萜酯 Monoterpene esters	(E)-己-3-烯基丁酸酯 (E)-Butanoic acid, 3-hexenyl ester	C₁₀H₁₈O₂	53398-84-8	1 185	0.04（0 ~ 0.72）
	（Z）-4-己烯基丁酸酯 Butyric acid (Z)-4-hexenyl ester	C₁₀H₁₈O₂	69727-41-9	1 203	0.01（0 ~ 0.15）
倍半萜	α-长叶蒎烯 α-Longipinene	C₁₅H₂₄	5989-08-2	1 353	0.05（0 ~ 0.15）
Sesquiterpenes	异戊酸香叶酯 Geranyl isovalerate	C₁₅H₂₆O₂	109-20-6	1 606	0.05（0 ~ 0.24）
	(-)-异长叶醇 Isolongifolol	C₁₃H₂₂O₂	1139-17-9	1 738	0.03（0 ~ 0.6）
双萜	香叶基芳樟醇 Linalool，geranyl-	C₂₀H₃₄O	1113-21-9	2 034	1.51（0 ~ 14.93）
Diterpenes	异植醇 Isophytol	C₂₀H₄₀O	505-32-8	1 948	0.13（0 ~ 0.95）
芳香族 Benzenoid and derivatives	4A-甲基-4,4a,5,6,7,8-六氢-3H-萘-2-酮 4A-Methyl-3,4,5,6,7,8-hexahydronaphthalen-2-one	C₁₁H₁₆O	826-56-2	—	4.77（0.89 ~ 10.02）
	4-羟基苯乙酸乙酯 Tyrosol, acetate	C₁₀H₁₂O₃	58556-55-1	1 568	3.71（0.61 ~ 12.42）
	2,4-二叔丁基酚 2,4-Di-tert-butylphenol	C₁₄H₂₂O	96-76-4	1 519	2（1.02 ~ 4.1）
	4-羟基-苯乙醇 Benzeneethanol, 4-hydroxy-	C₈H₁₀O₂	501-94-0	1 444	1.24（0.02 ~ 4.76）
	4-甲氧基苯乙醇 2-（4-Methoxyphenyl）ethanol	C₉H₁₂O₂	702-23-8	1 374	0.84（0 ~ 8.66）
	2,2'-亚甲基双-（4-甲基-6-叔丁基苯酚）Phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-methyl-	C₂₃H₃₂O₂	119-47-1	2 414	0.49（0.1 ~ 1.25）
	2-羟基-2-甲基-1-苯基-1-丙酮 2-Hydroxy-iso-butyrophenone	C₁₀H₁₂O₂	7473-98-5	1 278	0.32（0.17 ~ 0.65）
	苯甲酸 Benzoic acid	C₇H₆O₂	65-85-0	—	0.28（0 ~ 2.37）
	依杜兰 Edulan	C₁₃H₂₀O	41678-29-9	1 314	0.08（0 ~ 0.45）
	4-羟基苯丙酮 p-Hydroxyphenylacetone	C₉H₁₀O₂	770-39-8	1 483	0.08（0 ~ 0.3）
	2,5-二甲基苯甲醛Benzaldehyde, 2,5-dimethyl-	C₉H₁₀O	5779-94-2	1 208	0.07（0 ~ 0.33）
	苯甲酸异丙酯Benzoic acid, 1-methylethyl ester	C₁₀H₁₂O₂	939-48-0	1 217	0.04（0 ~ 0.75）
	3,3,5,6-四甲基-1,2-二氢茚 Indan, 1,1,4,6-tetramethyl-	C₁₃H₁₈	941-60-6	1 350	0.01（0 ~ 0.16）
	α-甲基-1,4-苯二甲醇 α-methyl-1,4-Benzenedimethanol	C₉H₁₂O₂	80463-22-5	1 417	0.01（0 ~ 0.24）
	丁酸苯乙酯 β-Phenylethyl butyrate	C₁₂H₁₆O₂	103-52-6	1 447	0.01（0 ~ 0.19）
	苯乙醛 α-Tolualdehyde	C₈H₈O	122-78-1	1 045	0（0 ~ 0.06）
	4-羟基苯丙醛 3-（4-Hydroxyphenyl）propanal	C₉H₁₀O₂	20238-83-9	1 490	0（0 ~ 0.07）

品种群 Group	品种名 Cultivar	含量/（μg · g^-1FW） Content	品种群 Group	品种名 Cultivar	含量/（μg · g^-1FW） Content
四季桂	日香桂 Rixianggui	147.92 ± 9.72 a	金桂	速生金桂 Susheng Jingui	115.52 ± 3.14 ab
Asiaticus	小蓉黄 Xiaoronghuang	135.85 ± 2.81 ab	Luteus	大花金桂 Dahua Jingui	85.33 ± 6.91 b
	橘叶四季桂 Juye Sijigui	124.19 ± 7.87 ab		金秋早 Jinqiuzao	84.86 ± 9.01 b
	月月红 Yueyuehong	112.73 ± 16.03 ab		球桂 Qiugui	79.79 ± 3.39 b
	大叶四季桂 Daye Sijigui	91.62 ± 5.14 b		橙黄金桂 Chenghuang Jingui	67.86 ± 4.02 bc
银桂	玉帘银丝 Yulian Yinsi	148.14 ± 5.06 a	丹桂	满条红 Mantiaohong	79.22 ± 14.58 b
Albus	卷叶银桂 Juanye Yingui	129.89 ± 3.55 ab	Aurantiacus	状元红 Zhuangyuanhong	61.63 ± 0.82bc
	柳叶银桂 Liuye Yingui	122.00 ± 5.48 ab		雄黄桂 Xionghuanggui	48.26 ± 0.54 c
	晚银桂 Wanyingui	78.31± 5.97 bc		象山丹桂Xiangshan Dangui	47.51 ± 0.78 c
	中华红龙桂 Zhonghua Honglonggui	98.55 ± 1.75 b		小叶朱砂桂Xiaoye Zhushagui	108.51 ± 6.32 ab

品种群 Group	品种名 Cultivar	含量/（μg · g^-1FW） Content	品种群 Group	品种名 Cultivar	含量/（μg · g^-1FW） Content
四季桂	日香桂 Rixianggui	147.92 ± 9.72 a	金桂	速生金桂 Susheng Jingui	115.52 ± 3.14 ab
Asiaticus	小蓉黄 Xiaoronghuang	135.85 ± 2.81 ab	Luteus	大花金桂 Dahua Jingui	85.33 ± 6.91 b
	橘叶四季桂 Juye Sijigui	124.19 ± 7.87 ab		金秋早 Jinqiuzao	84.86 ± 9.01 b
	月月红 Yueyuehong	112.73 ± 16.03 ab		球桂 Qiugui	79.79 ± 3.39 b
	大叶四季桂 Daye Sijigui	91.62 ± 5.14 b		橙黄金桂 Chenghuang Jingui	67.86 ± 4.02 bc
银桂	玉帘银丝 Yulian Yinsi	148.14 ± 5.06 a	丹桂	满条红 Mantiaohong	79.22 ± 14.58 b
Albus	卷叶银桂 Juanye Yingui	129.89 ± 3.55 ab	Aurantiacus	状元红 Zhuangyuanhong	61.63 ± 0.82bc
	柳叶银桂 Liuye Yingui	122.00 ± 5.48 ab		雄黄桂 Xionghuanggui	48.26 ± 0.54 c
	晚银桂 Wanyingui	78.31± 5.97 bc		象山丹桂Xiangshan Dangui	47.51 ± 0.78 c
	中华红龙桂 Zhonghua Honglonggui	98.55 ± 1.75 b		小叶朱砂桂Xiaoye Zhushagui	108.51 ± 6.32 ab