‘白兰地’海棠不同花期与不同花器官的香气成分分析

周晨晨; 范俊俊; 谭瑞楠; 杨峰; 张往祥

doi:10.19303/j.issn.1008-0384.2022.008.009

‘白兰地’海棠不同花期与不同花器官的香气成分分析

doi: 10.19303/j.issn.1008-0384.2022.008.009

1.
南京林业大学林学院，江苏　南京　210037
2.
金陵科技学院园艺与园林学院，江苏　南京　210038
3.
青岛市政监理咨询有限公司，山东　青岛　266000

基金项目: 扬州现代农业科技项目（YZ2019037）；江西省林业局科技创新专项（202121）

详细信息

作者简介:
周晨晨（1995−），男，硕士，主要从事林木种苗及海棠育种研究（E-mail：nlzhoucc@njfu.edu.cn）

通讯作者:
张往祥（1965-），男，教授，主要从事观赏植物应用研究（E-mail：malus2011@163.com）

中图分类号: S 685.99
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出版历程
- 收稿日期: 2021-12-16
- 修回日期: 2022-03-31
- 网络出版日期: 2022-08-08
- 刊出日期: 2022-08-28

Aromatics in Floral Organs of Malus Brandywine during Different Flowering Stages

1.
College of Forestry，Nanjing Forestry University, Nanjing, Jiangsu　210037, China
2.
College of Horticulture and Landscape Architecture，Jinling Institute of Technology, Nanjing, Jiangsu　210038, China
3.
Qingdao Municipal Supervision and Consulting Co., Ltd., Qingdao, Shandong　266000, China

摘要

摘要: 目的探索‘白兰地’海棠（M. 'Brandywine'）花香成分释放规律，为海棠芳香花育种和花香调控奠定基础。方法以香气浓郁的‘白兰地’海棠花朵鲜样为试材，采用固相微萃取与气质联用技术（SPME-GC-MS）分析不同花期和不同花器官的香气成分差异。结果（1）从大蕾期到盛花期分别检测出23、30、30、32种挥发性成分，其中叶醇、芳樟醇、己酸甲酯、乙酸叶醇酯、甲基庚烯酮和α-法呢烯为‘白兰地’海棠主要挥发性成分。花香总释放量呈现先上升后下降的趋势，在盛花期达到最高。香气成分种类构成主要以萜烯类（14.47 %～37.30 %）和醛酮类（21.64 %～38.78 %）为主，相对含量分别在盛花期和大蕾期达到最高，萜烯类相对含量在花朵开放过程中先上升后下降，而烷烃类和酯类呈现先下降后上升的趋势。对不同时期与挥发性成分之间进行了主成分分析，累计方差贡献率达 87.64 %，芳樟醇和壬醛分别在PC1正、负方向上贡献最大，分别与大蕾期和初花期呈高度正相关。（2）盛花期花朵花瓣、雌蕊（含花萼）和雄蕊中分别检测出28、32、25种挥发性成分。雌蕊总释放量最高，花瓣最低，对不同花器官与挥发性成分之间进行了主成分分析，累计方差贡献率达98.65 %。己酸甲酯、芳樟醇和α-法呢烯在PC1和PC2上的贡献较高，分别是花瓣、雄蕊和雌蕊的主要香气成分。3种花器官均位于不同象限，不同花器官的花香成分存在明显差异。结论叶醇、芳樟醇、己酸甲酯、乙酸叶醇酯、甲基庚烯酮和α-法呢烯为‘白兰地’海棠主要挥发性成分，盛花期香气成分种类构成主要以萜烯类为主，不同花器官的花香成分存在明显差异，挥发性成分释放的主要花器官是雌蕊。
- 海棠 /
- 花期 /
- 花器官 /
- 挥发性成分 /
- 花香释放规律
Abstract: Objective Release of aromatics from floral organs of Malus Brandywine was studied for new variety breeding. Method Freshly picked floral organ samples of the strongly fragrant Malus Brandywine in different flowering stages were analyzed for aromatic components by SPME-GC-MS. Result (1) There were 23, 30, 30, and 32 volatiles detected in the floral organs from budding to full bloom stage. They included predominantly (Z)-3-hexen-1-ol, linalool, hexanoic acid-methyl ester, (Z)-3-hexen-1-ol, and 6-methyl-5-hepten-2-one, and α-farnesene. The total fragrance release was in an increasing trend initially to peak at the full bloom stage before decline toward the end. The released aromatics consisted largely of terpenes (14.47-37.30%) and aldehydes and ketones (21.64-38.78 %) with the highest relative contents of terpenes at full bloom, while aldehydes and ketones when large buds appeared. The terpenoids increased at opening of the flowers followed by a decline, while alkanes and esters decreased at first but rose later. A principal component analysis on the volatiles at different flowering stages showed a cumulative variance contribution of 87.64%. On PC1, linalool contributed the most and significantly correlated positively in the large bud stage, whereas nonanal the most and significantly correlated negatively in the initial flowering stage. (2) At full blooming, 28, 32, and 25 volatiles were detected in the petals, pistil (including calyx), and stamens, respectively. The greatest fragrance release in quantity came from the pistil and the least from the petals. A principal component analysis on the compounds in different organs yielded a cumulative variance contribution of 98.65 %. On PC1 and PC2, hexanoic acid-methyl ester, linalool, and α-farnesene contributed more and were the major aromatics in the petals, stamens, and pistils, respectively. The 3 floral organs were in different quadrants and significantly differed in the composition of the aromatics they released. Conclusion (Z)-3-hexen-1-ol, linalool, hexanoic acid-methyl ester, (Z)-3-hexen-1-ol, 6-methyl-5-hepten-2-one, and α-Farnesene were the major volatiles in floral organs of Malus Brandywine. Terpenes were the dominant aromatics released during the full bloom stage. Significantly differences in the aromatic composition of the fragrance discharged from different floral organs. The releases of these volatiles took place mainly in the pistil.
- Malus /
- flowering period /
- floral organs /
- volatile components /
- floral fragrance release pattern

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图 1 ‘白兰地’不同花期挥发性成分的峰面积图

Figure 1. Peak areas of Malus Brandywine volatiles at different flowering stages

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图 2 不同花期挥发性成分种类的相对含量比较

Figure 2. Relative contents of volatiles in floral organs at different flowering stages

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图 3 ‘白兰地’不同花器官挥发性成分的峰面积图

Figure 3. Peak areas of Malus Brandywine volatiles in floral organs

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图 4 不同花器官挥发性成分种类的相对含量比较

Figure 4. Relative contents of volatiles in floral organs

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图 5 挥发性成分的主成分分析

①A：花期；B：花器官。②图中数字1：己酸甲酯；2：甲基庚烯酮；3：乙酸叶醇酯；4：芳樟醇；5：壬醛；6：(E)-4,8-二甲基-1,3,7-壬三烯；7：正十二烷；8：2-十三烷酮；9：α-法呢烯；10：4-辛烯酸甲酯；11：辛酸甲酯；12：苯乙醇；13：4-亚甲基异佛尔酮。

Figure 5. Principal component analysis based on volatiles

①A: flowering stages; B: floral organs. ②1: Hexanoic acid-methyl ester; 2: 6-methyl-5-hepten-2-one; 3: (Z)-3-hexen-1-ol, acetate,; 4: linalool; 5: nonanal; 6: (E)-4,8-dimethylnona-1,3,7-triene; 7: dodecane; 8: 2-tridecanone; 9: α-farnesene; 10: 4-octenoic acid, methyl ester; 11: octanoic acid, methyl ester; 12: phenylethyl alcohol; 13: 4-methyleneisophorone.

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表 1 ‘白兰地’海棠不同花期的挥发性成分鉴定

Table 1. Identification of volatiles in different flowering stages of Malus Brandywine

化合物 Compound	保留时间 Retention time/s	相对含量 Relative content/%
化合物 Compound	保留时间 Retention time/s	大蕾期 Bud	初花期 Initial flowering	盛花期 Flowering	末花期 End flowering
萜烯类 Terpenes
芳樟醇 Linalool	9.92	—	25.19±5.27 a	14.75±0.63 b	13.05±1.99 b
壬醛 Nonanal	9.96	18.48±0.25	—	—	—
(E)-4,8-二甲基-1,3,7-壬三烯 (E)-4,8-Dimethylnona-1,3,7-triene	10.17	—	—	9.74±2.54 a	5.71±0.59 b
β-紫罗兰酮 3-Buten-2-one,4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-	15.54	—	—	0.71±0.25 b	2.42±0.63 a
香叶基丙酮 5,9-Undecadien-2-one, 6,10-dimethyl-	17.68	—	1.12±0.09 b	4.70±0.33 a	4.83±0.33 a
二氢-Β-紫罗兰酮 2-Butanone,4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-	17.92	—	0.05±0.01 b	0.36±0.16 b	2.46±0.85 a
α-法呢烯 à-Farnesene	19.55	14.47±4.67 a	6.94±2.44 b	7.04±3.26 b	7.28±1.39 b
酯类 Esters
己酸甲酯 Hexanoic acid, methyl ester	6.57	1.26±1.51 c	11.67±1.24 a	7.12±2.85 b	7.31±0.82 b
乙酸叶醇酯 3-Hexen-1-ol, acetate, (Z)-	8.01	9.37±2.77 a	3.93±0.74 b	0.82±0.04 c	0.70±0.61 c
5-庚烯酸甲酯 5-Heptenoic acid, methyl ester	8.29	—	—	—	0.01±0.01
2-乙基己酸甲酯 Hexanoic acid, 2-ethyl-, methyl ester	8.62	—	—	0.42±0.20 a	0.34±0.12 b
丙酸芳樟酯 1,6-Octadien-3-ol, 3,7-dimethyl-, propanoate	8.82	1.30±0.12	—	—	—
4-辛烯酸甲酯 4-Octenoic acid, methyl ester	10.19	—	2.54±0.29	—	—
辛酸甲酯 Octanoic acid, methyl ester	10.37	0.32±0.12 b	2.98±0.46 a	2.00±0.73 a	2.49±0.35 a
异戊酸香叶酯 Geranyl isovalerate	10.85	0.34±0.14 a	0.06±0.01 b	—	—
顺-3-己烯基丁酸酯 Butanoic acid, 3-hexenyl ester, (Z)-	11.72	—	1.17±0.31 a	0.38±0.03 b	0.75±0.24 b
(10E)-10-十七烯-8-炔酸甲酯 10-Heptadecen-8-ynoic acid, methyl ester, (E)-	12.59	—	—	—	0.20±0.15
顺式-3-己烯醇 2-甲基丁酸酯 cis-3-Hexenyl-à-methylbutyrate	12.86	2.36±0.47 a	1.66±0.16 b	—	—
3-甲基-2-丁烯酸-2-苯乙酯 2-Butenoic acid, 3-methyl-, 2-phenylethyl ester	15.04	—	—	—	1.14±0.44
(Z,Z)-3-己烯基2-甲基-2-丁烯酸酯 (Z)-(Z)-Hex-3-en-1-yl 2-methylbut-2-enoate	15.09	—	0.87±0.14	—	—
顺式-3-己烯醇苯甲酸酯 3-Hexen-1-ol, benzoate, (Z)-	21.83	—	—	0.08±0.07	—
肉豆蔻酸甲酯 Methyl tetradecanoate	25.90	—	—	0.11±0.04 a	0.16±0.06 a
醇类 Alcohols
叶醇 3-Hexen-1-ol, (Z)-	5.82	9.00±0.50 a	7.71±1.25 ab	5.57±1.18 ab	4.40±0.45 b
3-甲基-4-戊醇 4-Penten-1-ol, 3-methyl-	6.22	—	0.12±0.04 a	0.04±0.01 ab	0.11±0.05 a
苯乙醇 Phenylethyl Alcohol	10.51	—	—	2.35±0.73 b	4.82±0.61
4-甲氧基苯乙醇 2-(4-Methoxyphenyl)ethanol	17.07	—	—	0.25±0.10 a	0.19±0.06 a
醛酮类 Aldehydes and ketones
4-羟基查耳酮 4-Hydroxychalcone	5.20	1.35±0.23 a	0.44±0.09 ab	0.56±0.19 ab	1.18±1.00 a
甲基庚烯酮 5-Hepten-2-one, 6-methyl-	7.67	14.98±1.29 a	10.39±2.10 b	6.49±0.49 c	7.56±0.12 c
4-氧代异佛尔酮 2,6,6-Trimethyl-2-cyclohexene-1,4-dione	10.95	—	1.76±0.16 a	2.01±1.10 a	—
2,2,6-三甲基-1,4-环己二酮 1,4-Cyclohexanedione,2,2,6-trimethyl-	11.51	—	0.57±0.22 ab	0.90±0.14 a	—
癸醛 Decanal	12.25	2.93±0.58 a	1.83±0.29 b	—	1.06±0.07 c
4-亚甲基异佛尔酮 4-Methyleneisophorone	12.78	1.04±0.18 d	3.28±0.95 c	6.51±0.83 b	8.56±0.30 a
2-十三烷酮 2-Tridecanone	19.24	—	2.15±0.89 bc	11.44±5.66 a	7.00±2.12 ab
2-十五烷酮 2-Pentadecanone	25.34	—	1.22±0.61 bc	5.67±2.24 a	3.17±1.10 a
烷烃类 Alkanes
癸烷 Decane	7.87	0.14±0.01 a	0.11±0.00 a	—	—
正十一烷 Undecane	9.78	2.11±0.41 a	1.25±0.32 b	—	—
3-甲基十一烷 Undecane, 3-methyl-	11.33	1.97±0.24	—	—	—
正十二烷 Dodecane	11.99	10.46±1.50 a	6.60±0.64	2.31±0.39 c	3.76±0.53 c
正十三烷 Tridecane	14.35	1.11±0.30 a	0.87±0.14 a	1.18±0.03 a	1.20±0.12 a
7-甲基十七烷 Heptadecane, 7-methyl-	15.20	0.54±0.03 a	0.40±0.04 a	—	—
9-甲基十九烷 Nonadecane, 9-methyl-	15.30	—	0.15±0.05	—	—
10-甲基二十烷 Eicosane, 10-methyl-	15.49	0.35±0.06	—	—	—
3-甲基十三烷 Tridecane, 3-methyl-	16.05	2.19±0.31 a	1.29±0.24 b	0.52±0.03 c	—
3-亚甲基十三烷 Tridecane, 3-methylene-	16.43	1.15±0.05	—	—	—
正十四烷 Tetradecane	16.76	2.79±0.44 b	1.76±0.20 c	2.51±0.28 b	4.14±0.35 a
正十六烷 Hexadecane	22.40	—	—	—	0.36±0.03
正二十一烷 Heneicosane	28.45	—	—	—	0.82±0.49
酚类 Phenols
对甲苯甲醚 Benzene, 1-methoxy-4-methyl-	8.43	—	—	3.36±1.78 a	1.69±0.68 b
甲基苯乙基醚 Benzene, (2-methoxyethyl)-	9.61	—	—	—	1.12±0.07
2,6-二叔丁基对甲酚 Butylated Hydroxytoluene	19.82	—	—	0.09±0.03	—
“—”表示该数据未被检索到或者未被检测出；同一行中不同的小写字母表示在 0.05 水平上差异显著。表2同。 "—" indicates that the data have not been reported by other studies or the compound has not been detected. Different lowercases in the same line indicate the significant difference at 0.05 level．The same as table 2.

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表 2 ‘白兰地’海棠不同花器官的挥发性成分鉴定

Table 2. Identification of Malus Brandywine volatiles in floral organs

化合物 Compound	保留时间 Retention time/s	相对含量 Relative content/%
化合物 Compound	保留时间 Retention time/s	花瓣 Petals	雌蕊 Pistil	雄蕊 Stamens
萜烯类 Terpenes
芳樟醇 Linalool	9.92	10.01±2.00 b	—	23.59±4.01 a
(E)-4,8-二甲基-1,3,7-壬三烯 (E)-4,8-Dimethylnona-1,3,7-triene	10.15	—	6.03±0.60	—
β-紫罗兰酮 3-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-	15.53	—	1.81±0.34	—
香叶基丙酮 5,9-Undecadien-2-one, 6,10-dimethyl-	17.66	2.29±0.59 b	2.63±0.01 ab	3.85±0.72 a
二氢-Β-紫罗兰酮 2-Butanone, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-	17.90	—	3.05±0.48 a	0.91±0.28 b
α-法呢烯 à-Farnesene	19.55	3.33±1.14 b	34.12±2.90 a	3.74±2.57 b
酯类 Esters
己酸甲酯 Hexanoic acid, methyl ester	6.54	35.41±2.72 a	2.87±0.67 b	—
乙酸叶醇酯 3-Hexen-1-ol, acetate, (Z)-	7.98	0.59±0.18 b	20.47±0.39 a	—
5-庚烯酸甲酯 5-Heptenoic acid, methyl ester	8.25	—	0.03±0.01	—
庚酸甲酯 Heptanoic acid, methyl ester	8.29	1.11±0.38 a	—	0.40±0.37 b
2-乙基己酸甲酯 Hexanoic acid, 2-ethyl-, methyl ester	8.62	0.17±0.01	—	—
4-辛烯酸甲酯 4-Octenoic acid, methyl ester	10.17	5.91±1.06 b	—	12.33±1.70 a
辛酸甲酯 Octanoic acid, methyl ester	10.32	13.60±5.33 a	2.60±0.12 b	4.89±0.06 aab
3-丁酸己烯酯 Butanoic acid, 3-hexenyl ester, (E)-	10.71	—	0.91±0.09	—
顺-3-己烯基丁酸酯 Butanoic acid, 3-hexenyl ester, (Z)-	11.68	—	4.99±0.55	—
2-甲基丁酸己酯 Butanoic acid, 2-methyl-, hexyl ester	12.84	—	3.00±0.49 a	0.53±0.03 b
己酸异戊酯 Isopentyl hexanoate	13.16	—	—	0.20±0.05
3-壬酸甲酯 3-Nonenoic acid, methyl ester	14.60	—	0.26±0.01	—
(Z,Z)-3-己烯基2-甲基-2-丁烯酸酯 (Z)-(Z)-Hex-3-en-1-yl 2-methylbut-2-enoate	15.01	—	2.39±0.00	—
己酸叶醇酯 Hexanoic acid, 3-hexenyl ester, (Z)-	16.35	0.51±0.09 b	2.44±0.05 a	—
己酸己酯 Hexanoic acid, hexyl ester	16.44	0.25±0.02 b	0.85±0.04 a	—
顺式-3-己烯醇苯甲酸酯 3-Hexen-1-ol, benzoate, (Z)-	21.81	—	0.45±0.06 a	0.22±0.02 a
肉豆蔻酸甲酯 Methyl tetradecanoate	25.90	0.31±0.15	—	—
醇类 Alcohols
叶醇 3-Hexen-1-ol, (Z)-	5.78	4.45±0.90 a	5.84±1.31 a	—
3-甲基-1,5-戊二醇 1,5-Pentanediol, 3-methyl-	5.93	—	0.04±0.00	—
6-甲基-5-庚烯-2-醇 5-Hepten-2-ol, 6-methyl-	7.78	—	0.84±0.16 a	1.15±1.62 a
苯乙醇 Phenylethyl Alcohol	10.48	—	—	11.04±1.59
醛酮类 Aldehydes and ketones
4-羟基查耳酮 4-Hydroxychalcone	5.20	0.35±0.02 a	0.07±0.02 a	0.16±0.01 a
苯甲醛 Benzaldehyde	7.43	—	0.11±0.02	—
甲基庚烯酮 5-Hepten-2-one, 6-methyl-	7.66	5.64±0.65 a	0.57±0.17 b	7.75±1.86 a
癸醛 Decanal	12.20	0.55±0.09 b	0.73±0.04 b	2.28±0.29 a
4-亚甲基异佛尔酮 4-Methyleneisophorone	12.76	1.91±0.23 b	—	12.06±1.82 a
3,5-庚二烯醛 3,5-Heptadienal, 2-ethylidene-6-methyl-	13.22	—	0.02±0.00	—
2-十三烷酮 2-Tridecanone	19.24	6.62±3.78 a	—	2.58±0.17 b
2-十五烷酮 2-Pentadecanone	25.34	2.78±1.29 a	0.17±0.00 b	0.85±0.12 ab
烷烃类 Alkanes
正十一烷 Undecane	9.77	1.19±0.10 b	0.59±0.03 c	1.73±0.10 a
3-甲基十一烷 Undecane, 3-methyl-	11.33	0.37±0.08	—	—
正十二烷 Dodecane	11.97	0.75±0.06 b	0.31±0.08 c	1.45±0.01 a
正十三烷 Tridecane	14.35	0.41±0.06 a	0.22±0.04 a	0.49±0.05 a
3-甲基十三烷 Tridecane, 3-methyl-	16.05	0.14±0.01	—	—
正十四烷 Tetradecane	16.75	0.38±0.02 b	0.31±0.06 b	0.91±0.29 a
正十六烷 Hexadecane	22.39	0.17±0.02 b	0.06±0.00 c	0.42±0.05 a
酚类 Phenols
对甲苯甲醚 Benzene, 1-methoxy-4-methyl-	8.43	—	1.21±0.34 b	2.81±0.02 a
甲基苯乙基醚 Benzene, (2-methoxyethyl)-	9.61	0.73±0.16 b	—	3.64±0.14 a
2,6-二叔丁基对甲酚 Butylated Hydroxytoluene	19.80	0.05±0.04	—	—

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