Aromatics in Floral Organs of Michelia platypetala Hongyun
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摘要:
目的 探究红蕴含笑花香成分组成和含量变化规律，为阔瓣含笑的芳香育种与花香物质开发利用提供理论依据。 方法 采用顶空固相微萃取(HS-SPME)与气相色谱-质谱(GC-MS)联用法测定了红蕴含笑3个开花时期（花蕾期、初开期、盛开期）3个花器官（花被片、雄蕊、雌蕊）的花香成分，并进行主成分（PCA）和偏最小二乘法（PLS-DA）分析。 结果 从红蕴含笑3个开花时期3个花器官中共鉴定出100种花香成分，共11类化合物，其中萜类物质和烷烃类物质是红蕴含笑主要香气成分，两者之和占比在不同开花时期各花器官中相对含量均达到80%以上，酮类、醛类、醇类、杂环类和烯烃类等物质含量较低。鉴定出100种花香成分根据主要香气成分（相对含量＞1%）及各花器官不同时期特有香气成分筛选并列出49种物质，并以此为基础进行PCA和PLS-DA分析，可将3个开花时期红蕴含笑花器官进行分类，并筛选了13种差异性成分（VIP＞1），表明3个花器官的香气成分具有差异性显著。红蕴含笑花被片主要香气成分γ-杜松烯和1,2-二甲氧基苯分别带有香草味和甜奶油味，呈木香型和草香型。花蕾期花被片特有成分酯类物质己酸苯乙酯和醚类物质2-异丙基-5-甲基茴香醚，为花被片增添了甜香味和焦木味，呈花香型和草香型。初开期花被片特有成分酮类物质D-香芹酮为花被片增添了刺激香味，呈薄荷型。雄蕊主要香气成分γ-杜松烯和δ-榄香烯分别带有香草味和甜香味，呈木香型和草香型。雄蕊各开花时期特有成分醛类物质苯甲醛和酮类物质3-侧柏酮为雄蕊分别增添了杏仁味和刺激香味，呈果香型和木香型。雌蕊主要香气成分γ-杜松烯、(+)-香橙烯和δ-榄香烯分别带有香草味、木香味和甜香味，呈木香型和草香型。花蕾期雌蕊特有成分醇类物质γ-松油醇为雌蕊增添了松香味和丁香味，呈木香型。 结论 红蕴含笑花器官香气成分组成丰富，主要香气成分是萜类物质和烷烃类物质，主要释香部位是雄蕊，在开花进程中其香气特征因多种香气成分的相对含量和种类不断变化，使各花器官在3个开花时期呈现独特多样的花香。 Abstract:Objective Aromatics in various floral organs of Michelia platypetala Hongyun were analyzed for selective breeding and extended utilization of the fragrant components. Method Headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS) were employed to determine the aromatic components in the tepals, stamens, and pistils of Michelia platypetala Hongyun at flower budding, early blooming, and full blooming stages. And conduct Principal Component Analysis (PCA) and Partial Least Square Discriminant Analysis (PLS-DA). Result One hundred volatiles of 11 types were identified. Terpenoids and alkanes were the major ones that constituted over 80% of all. The contents of ketones, aldehydes, alcohols, heterocyclic compounds, and olefins were relatively low. Identify 100 types of floral aroma components, screen and list 49 substances based on the main aroma components (relative content>1%) and unique aroma components of each floral organ at different stages. The subsequently conducted PCA and PLS-DA analyses placed the aromatics in 13 distinct components at VIP＞1, indicating significant differences in the aromatic components of the three flower organs. The main aroma components of Michelia platypetala Hongyun perianth slices γ-cadinene and 1,2-Dimethoxybenzene have vanilla and sweet cream flavors, respectively, presenting a woody and herbaceous aroma. During the bud stage, the unique components of the petals, such as esters such as 2-Phenethyl hexanoate ester and ethers such as 2-Isopropyl-5-methylanisole, add a sweet and burnt wood flavor to the petals, presenting a floral and herbaceous aroma. The ketone substance D-carvone, a unique component of the early blooming petals, adds a stimulating flavor to the perianth slices, presenting a mint aroma. The main aroma components of stamens γ-Junipene and δ-Elemene has a vanilla and sweet flavor, respectively, presenting a woody and herbaceous aroma. The unique components of aldehydes and ketones at each flowering stage of stamens, such as Benzaldehyde and 3-Thujanone, add almond flavor and stimulating flavor to the stamens, presenting a fruity and woody aroma. Main aroma components of pistil γ-Junipene, (+)-Aromandendrene, and δ- Elemene has a vanilla, woody, and sweet flavor, respectively, presenting a woody and herbaceous aroma. Bud stage pistils specific components of alcohols γ-Terpineol alcohol for pistils added pine flavor and clove flavor, presenting a woody aroma. Conclusion The aroma components of the organs of Michelia platypetala Hongyun are rich. The main aroma components are terpenoids and alkanes, and the main aroma releasing site is the stamen during the bud stage. During the flowering process, the aroma characteristics are constantly changing due to the relative content and types of various aroma components, making each flower organ present unique and diverse floral fragrance in three flowering periods. -
Key words:
- HS-SPME-GC-MS /
- Michelia platypetala Hongyun /
- floral organs /
- aromatics /
- PCA /
- PLS-DA
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图 1 红蕴含笑3个不同开花时期的花被片、雄蕊和雌蕊
Figure 1. Tepals, stamens, and pistils of M. platypetala Hongyun in florescence stages
图 2 红蕴花被片各开花时期香气成分种类和相对含量
A:花被片各开花时期香气成分种类。B:花被片各开花时期香气成分相对含量。
Figure 2. Types and relative contents of aroma components at each flowering period in the tepals of Hongyun
A: The type of aroma components in each flowering period of tepals. B: The relative content of aroma components in each flowering period of tepals.
图 3 红蕴雄蕊各开花时期香气成分种类和相对含量
A:雄蕊各开花时期香气成分种类。B:雄蕊各开花时期香气成分相对含量。
Figure 3. Types and relative contents of aroma components at each flowering period in the stamens of Hongyun
A: The type of aroma components in each flowering period of stamens. B: The relative content of aroma components in each flowering period of stamens.
图 4 红蕴雌蕊各开花时期香气成分种类和相对含量
A:雌蕊各开花时期香气成分种类。B:雌蕊各开花时期香气成分相对含量。
Figure 4. Types and relative contents of aroma components at each flowering period in the pistils of Hongyun
A: The type of aroma components in each flowering period of pistils. B: The relative content of aroma components in each flowering period of pistils.
图 5 红蕴花香成分的PCA（A）和PLS-DA分析（B）
A：PCA得分/载荷图，图例X为香气成分具体序号，见表1。B：PLS-DA模型VIP得分图
Figure 5. PCA (A) and PLS-DA (B) on floral aromatics of Hongyun
A: Principal component analysis biplot (scores and loadings ) , Legend X shows the specific serial numbers of aroma components, as shown in Table 1. B: PLS-DA Model VIP Score Chart
表 1 红蕴不同开花时期不同花器官香气成分
Table 1. Aromatics in floral organs at different florescence stages of Hongyun
编号
No.化合物名称
Compound name相对含量 Relative content/% 花蕾期
花被片
AⅠ初开期
花被片
AⅡ盛开期
花被片
AⅢ花蕾期
雄蕊
BⅠ初开期
雄蕊
BⅡ盛开期
雄蕊
BⅢ花蕾期
雌蕊
CⅠ初开期
雌蕊
CⅡ盛开期
雌蕊
CⅢ单萜类 Monoterpenes 1 β-蒎烯
β-Pinene2.59±0.16 3.06±0.10 2.86±0.40 5.20±0.61 3.99±0.67 4.55±0.58 2.46±0.28 1.34±0.24 0.78±0.11 2 月桂烯
β-Myrcene0.58±0.06 0.64±0.10 0.84±0.09 0.98±0.10 0.85±0.14 0.89±0.11 0.71±0.07 0.25±0.03 0.15±0.02 3 α-水芹烯
α-Phellandrene1.61±0.09 2.88±0.06 1.91±0.20 2.32±0.08 2.52±0.17 2.22±0.08 2.77±0.08 1.61±0.09 1.05±0.03 4 对异丙基甲苯
p-Cymene0.80±0.07 0.68±0.06 1.20±0.11 1.01±0.06 0.73±0.07 0.87±0.07 0.82±0.12 0.50±0.07 0.26±0.04 5 D-柠檬烯
D-Limonene0.73±0.07 0.65±0.06 1.16±0.11 1.49±0.07 1.35±0.13 1.17±0.13 1.91±0.08 0.72±0.05 0.60±0.06 6 桉油精
Eucalyptol0.39±0.02 0.41±0.05 0.52±0.05 0.82±0.12 0.54±0.05 0.64±0.08 1.34±0.09 0.54±0.05 0.35±0.04 7 γ-松油烯
γ-Terpinene0.10±0.00 0.10±0.01 0.12±0.01 0.13±0.01 0.17±0.01 0.12±0.00 0.06±0.01 0.03±0.00 0.02±0.00 8 反-桧烯水合物
trans-Sabinene hydrate— — 0.01±0.00 0.01±0.00 0.01±0.00 0.01±0.00 0.01±0.00 — — 9 芳樟醇
Linalool1.57±0.13 1.47±0.10 1.93±0.08 2.39±0.10 2.51±0.18 2.43±0.07 1.41±0.09 0.66±0.09 0.32±0.04 10 别罗勒烯
(4E,6Z)-2,6-dimethylocta-2,4,6-triene— 0.01±0.00 0.01±0.00 — 0.01±0.00 — 0.01±0.00 — — 11 橙花醇
Neral0.06±0.01 0.06±0.01 0.06±0.00 0.02±0.00 0.05±0.01 0.02±0.00 0.10±0.02 — — 12 α-雪松烯
(+)-α-himachalene3.25±0.14 3.55±0.08 2.97±0.20 7.38±0.72 4.96±0.44 7.12±0.54 5.36±0.23 6.46±0.52 5.73±0.36 倍半萜类 Sesquiterpenes 13 δ-榄香烯
δ-Elemene3.43±0.08 3.22±0.22 2.85±0.32 5.41±0.49 7.83±0.60 5.04±0.45 7.68±1.06 5.73±0.63 6.24±0.36 14 α-荜澄茄油烯
α-Cubebene0.13±0.01 0.12±0.01 0.11±0.01 0.06±0.01 0.08±0.00 0.05±0.00 0.20±0.02 0.18±0.01 0.19±0.00 15 β-荜澄茄油烯
β-Cubebene1.73±0.14 2.26±0.07 2.12±0.15 0.81±0.06 1.69±0.13 0.83±0.07 1.64±0.13 1.29±0.10 1.95±0.04 16 β-异可烯
β-Isocomene4.82±0.67 5.17±0.48 4.50±0.15 13.24±0.94 12.78±0.54 11.80±0.36 3.85±0.12 4.34±0.35 4.15±0.43 17 (+)-香橙烯
(+)-Aromandendrene1.91±0.20 2.06±0.09 1.58±0.16 4.35±0.62 2.50±0.08 3.33±0.05 10.99±1.06 6.59±0.70 6.42±0.40 18 缬草-4,7(11)-二烯
Valerena-4,7(11)-diene2.77±0.12 2.65±0.10 2.35±0.15 7.15±0.55 5.22±0.42 6.09±0.14 4.08±0.20 3.23±0.15 3.54±0.28 19 (+)-表双环倍半水芹烯
(+)-epi-Bicyclosesquiphellandrene0.72±0.06 1.08±0.09 0.55±0.04 0.66±0.06 0.56±0.04 0.41±0.05 0.91±0.11 0.47±0.04 0.81±0.10 20 γ-杜松烯
γ-Cadinene4.50±0.53 4.29±0.48 4.25±0.47 8.82±0.87 6.36±0.54 8.66±0.60 6.67±0.37 7.78±0.47 7.00±0.36 21 3,9-愈创木二烯
Guaia-3,9-diene3.46±0.30 4.47±0.57 3.06±0.31 6.81±0.88 5.39±0.58 7.28±0.71 6.28±0.43 7.46±1.75 8.00±0.60 醇类 alcohols 22 2-甲基-2-庚醇
2-Methyl-2-heptanol— — — 0.01±0.00 — — 0.01±0.00 — — 23 反式-2-蒎烷醇
trans-2-Pinanol— — — — — — 0.01±0.00 — — 24 (−)-4-松油醇
(−)-4-Terpineol— — — — — — 0.01±0.00 — — 25 γ-松油醇
γ-Terpineol— — — — — — 0.01±0.00 — — 26 木薄荷衍生物
Prostantherol, derivative of— — — — — 0.01±0.00 0.01±0.00 — 0.01±0.00 27 (7β,9α)-柏木烯醇
(7β,9α)-Cedr-8(15)-en-9-ol— — — — — — 0.03±0.00 — — 28 顺-11-十四碳烯-1-醇
cis-11-Tetradecen-1-ol0.01±0.00 0.02±0.00 0.02±0.00 — — 0.01±0.00 0.02±0.00 — 0.01±0.00 29 6-异丙烯基-4,8a-二甲基-
1,2,3,5,6,7,8,8a-八氢萘-2-醇
6-Isopropenyl-4,8a-dimethyl-1,2,3,5,6,7,
8,8a-octahydro-naphthalen-2-ol— — — — — 0.01±0.00 — — — 30 十六醇
Cetyl Alcohol— — — 0.02±0.00 0.01±0.00 0.01±0.00 — — 0.01±0.00 烷烃类 Alkanes 31 十二烷
Dodecane0.01±0.00 — 0.01±0.00 — — — — — — 32 十三烷
Tridecane1.68±0.08 1.23±0.05 1.51±0.07 0.13±0.01 0.50±0.04 0.12±0.01 0.34±0.01 0.32±0.01 0.13±0.01 33 2,6,10-三甲基十四烷
2,6,10-trimethyltetradecane23.79±1.52 23.08±0.63 23.04±0.45 10.56±0.64 13.92±0.49 13.16±0.45 11.61±1.02 19.53±0.46 22.13±0.40 34 异十六(碳)烷
Isohecadecane23.67±0.71 22.98±0.59 22.91±0.87 10.43±0.48 13.92±0.59 13.14±0.57 11.47±0.85 19.44±0.67 22.01±0.43 35 十七烷
Heptadecane1.04±0.09 1.04±0.05 0.95±0.07 0.20±0.02 0.30±0.01 0.42±0.05 0.66±0.02 0.43±0.01 0.79±0.03 36 二十烷
Eicosane— — 0.01±0.00 0.02±0.00 0.02±0.00 0.03±0.00 0.03±0.00 — 0.02±0.00 酯类 Esters 37 水杨酸甲酯
Methyl salicylate2.96±0.16 3.11±0.05 3.13±0.27 0.06±0.01 0.22±0.01 0.04±0.00 0.25±0.02 0.09±0.01 0.09±0.01 38 龙脑乙酸酯
(+)-Borneol acetate0.28±0.01 0.23±0.02 0.26±0.02 0.24±0.01 0.21±0.00 0.16±0.01 2.46±0.11 0.79±0.05 0.67±0.03 39 己酸苯乙酯
2-Phenethyl hexanoate0.01±0.00 — — — — — — — — 醛类 Aldehydes 40 苯甲醛
Benzaldehyde— — — 0.02±0.00 0.02±0.00 0.04±0.00 — — — 酮类 Ketones 41 2-庚酮
2-Heptanone0.04±0.00 0.04±0.01 0.04±0.00 0.09±0.01 0.07±0.00 0.07±0.01 0.02±0.00 — — 42 3-侧柏酮
3-Thujanone— — — 0.01±0.00 0.01±0.00 0.01±0.00 — — — 43 D-香芹酮
D-Carvone— 0.01±0.00 — — — — — — — 44 顺十二烷-6-烯-2-酮
(Z)-Undec-6-en-2-one0.05±0.01 0.04±0.00 0.05±0.00 0.06±0.01 0.08±0.01 0.07±0.00 0.02±0.00 — — 烯烃类 Olefins 45 1-甲基-1,4-环己二烯
1-Methyl-1,4-cyclohexadiene— — 0.01±0.00 — — — 0.02±0.00 — — 醚类 Ethers 46 2-异丙基-5-甲基茴香醚
2-Isopropyl-5-methylanisole0.01±0.00 — — — — — — — — 芳香族类 Aromatics 47 1,2-二甲氧基苯
1,2-Dimethoxybenzene3.89±0.14 2.53±0.12 3.05±0.21 2.89±0.16 3.04±0.14 2.51±0.09 4.27±0.13 5.17±0.47 1.97±0.14 酚类 Phenols 48 2-甲氧基苯酚
2-methoxy-Phenol0.95±0.18 1.06±0.06 2.49±0.21 0.24±0.02 0.31±0.01 0.29±0.01 0.36±0.02 0.44±0.04 0.40±0.03 杂环类 Heterocycles 49 3,4-二氢-2H-吡喃
3,4-Dihydro-2H-pyran— — 0.02±0.00 0.01±0.00 0.01±0.00 0.01±0.00 0.03±0.00 0.02±0.00 0.01±0.00 —：代表未检测到。
—：indicates no detection.
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