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‘白兰地’海棠不同花期与不同花器官的香气成分分析

花匠小妙招
2024-12-16 22:08

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。

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.

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

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

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

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

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.

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/%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.

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/% 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 — — [1] 陈秀中, 王琪. 中华民族传统赏花理论探微 [J]. 北京林业大学学报, 2001, 23(S1):16−21. DOI: 10.13332/j.1000-1522.2001.s1.006

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