林业科学 ›› 2022, Vol. 58 ›› Issue (11): 127-136.doi: 10.11707/j.1001-7488.20221112
郑刘辉,侯宇,张新凤,喻卫武,曾燕如,戴文圣*
收稿日期:
2021-03-21
出版日期:
2022-11-25
发布日期:
2023-03-08
通讯作者:
戴文圣
Liuhui Zheng,Yu Hou,Xinfeng Zhang,Weiwu Yu,Yanru Zeng,Wensheng Dai*
Received:
2021-03-21
Online:
2022-11-25
Published:
2023-03-08
Contact:
Wensheng Dai
摘要:
目的: 探究香榧假种皮不同制备方式与分析方法对挥发油成分含量测定的影响,揭示香榧种子生长发育过程中假种皮挥发油成分的动态变化规律,为香榧假种皮的利用提供参考。方法: 结合气相色谱-质谱联用(GC-MS)技术,优化水蒸气蒸馏法(SD)和顶空固相微萃取法(HS-SPME)样品制备条件,选择适合的方法测定香榧种子生长发育过程中假种皮挥发性油成分与含量。结果: 1)基于GC-MS的分析结果,从成分种类及含量上来看,SD更适合香榧假种皮挥发油分析样品的制备。2)用SD-GC-MS分析,检测出假种皮挥发油成分有47种,包含萜烯类21种(柠檬烯、α-蒎烯、δ-杜松烯等)、萜醇类15种(芳樟醇、冰片、榄香醇等)、萜烯酯类3种(乙酸冰片酯、乙酸松油酯、乙酸香叶酯)、其他化合物8种(胡椒酮、抗氧剂264、棕榈酸等)。3)种子生长发育过程中,假种皮中的挥发性成分呈一定的变化规律,其中莰烯、β-蒎烯、萜品油烯等含量5—9月均呈上升趋势;部分成分5—8月上升到最大值后开始下降,如α-蒎烯、桧烯、月桂烯等;5—6月和8—9月单萜类和倍半萜类成分呈明显的负相关趋势,而6—7月由于假种皮处于生长时期,单萜类和倍半萜类组分均呈增加趋势。主成分分析发现,假种皮挥发油成分在5月和6月、7月和8月比较相似。结论: 香榧假种皮挥发油SD提取条件为料液比为1∶10、浸泡时间为1 h、提取时间为4 h;通过SD-GC-MS检测出47种化合物,共13 483.14 μg·g-1,主要成分为柠檬烯、α-蒎烯等萜烯类化合物;不同种实生长发育期的香榧假种皮中挥发性组分差异较大,化合物种类从5月份的35种增加到了9月份的47种,倍半萜类和含氧衍生物积累增多,挥发油成分的总含量从5—9月份先升后降;5—6月、7—8月的假种皮挥发油成分组成及含量比较接近,而9月份与其他4个月份差异较大。
中图分类号:
郑刘辉,侯宇,张新凤,喻卫武,曾燕如,戴文圣. 香榧种子生长发育过程中假种皮挥发油的变化[J]. 林业科学, 2022, 58(11): 127-136.
Liuhui Zheng,Yu Hou,Xinfeng Zhang,Weiwu Yu,Yanru Zeng,Wensheng Dai. Changes of Volatile Oil Composition in Aril during the Growth and Development of Torreya grandis 'Merrillii' Seeds[J]. Scientia Silvae Sinicae, 2022, 58(11): 127-136.
表1
2种方法检测到的香榧假种皮挥发性组分①"
组分编码 No. | 保留时间 Retention time/min | 保留指数 Reteneion index | 化合物 Compounds | 分子式 Molecular formula | 化合物含量 Compound content/(μg·g-1) | |
水蒸气蒸馏法 SD | 顶空固相微萃取 HS-SPME | |||||
萜烯类Terpenes | ||||||
A1 | 7.04 | 940 | α-蒎烯α-pinene | C10H16 | 1 711.06±82.19 | 284.23±11.99 |
A2 | 7.45 | 954 | 莰烯Camphene | C10H16 | 458.39±20.24 | 101.58±10.07 |
A3 | 8.17 | 978 | 桧烯Sabinene | C10H16 | 15.04±0.98 | — |
A4 | 8.23 | 980 | β-蒎烯β-pinene | C10H16 | 440.10±25.43 | 23.27±1.30 |
A5 | 8.64 | 994 | 月桂烯Myrcene | C10H16 | 250.91±9.53 | 55.03±2.85 |
A6 | 9.84 | 1 033 | 柠檬烯Limonene | C10H16 | 4 681.36±131.08 | 592.42±30.05 |
A7 | 10.67 | 1 061 | 罗勒烯Ocimene | C10H16 | 21.61±0.44 | — |
A8 | 11.5 | 1 090 | 萜品油烯Terpinolene | C10H16 | 245.03±14.52 | 44.37±2.29 |
A9 | 12.7 | 1 129 | 别罗勒烯Alloocimene | C10H16 | 16.94±1.80 | — |
A10 | 18.47 | 1 337 | δ-榄香烯δ-elemene | C15H24 | 80.41±4.82 | 18.32±1.89 |
A11 | 18.77 | 1 349 | α-荜澄茄油烯α-cubebene | C15H24 | 214.38±9.95 | 60.81±2.77 |
A12 | 19.86 | 1 392 | 古巴烯Copaene | C15H24 | 380.39±18.41 | — |
A13 | 20.67 | 1 424 | 反式石竹烯trans-caryophyllene | C15H24 | 163.13±7.72 | 30.03±1.24 |
A14 | 21.55 | 1 459 | (E)-β-金合欢烯 (E)-β-farnesene | C15H24 | 390.67±16.51 | 77.70±3.19 |
A15 | 22.05 | 1 480 | δ-杜松烯δ-cadinene | C15H24 | 814.25±34.24 | 155.33±2.27 |
A16 | 22.14 | 1 483 | (+)-γ-杜松烯 (+)-γ-Cadinene | C15H24 | 75.76±6.41 | 13.74±0.60 |
A17 | 22.25 | 1 492 | 荜澄茄油烯Cubebene | C15H24 | 717.41±29.19 | 90.77±1.19 |
A18 | 22.42 | 1 494 | (-)-β-花柏烯(-)-β-chamigrene | C15H24 | 33.37±1.4 | 27.10±1.36 |
A19 | 22.75 | 1 503 | α-衣兰油烯α-muurolene | C15H24 | 252.45±10.03 | 27.10±0.69 |
A20 | 23.31 | 1 512 | β-愈创木烯β-guaiene | C15H24 | 41.85±2.07 | — |
A21 | 31.36 | 1 998 | 异扁枝烯Isophyllocladene | C20H32 | — | 4.73±0.23 |
A22 | 32.85 | 2 105 | 松香-7, 13-二烯Abieta-7, 13-diene | C20H32 | 76.68±6.86 | 21.25±0.69 |
总和Total | 11 081.18±398.14 | 1607.43±34.14 | ||||
醇类Terpene alcohols | ||||||
B1 | 11.84 | 1 098 | 芳樟醇Linalol | C10H18O | 29.58±2.46 | — |
B2 | 13.84 | 1 170 | 冰片Borneol | C10H18O | 72.44±5.42 | — |
B3 | 14.14 | 1 181 | (-)-4-萜品醇 (-)-4-Terpineol | C10H18O | 182.94±11.92 | — |
B4 | 14.55 | 1 196 | (+)-α-松油醇 (+)-α-terpineol | C10H18O | 289.09±10.20 | — |
B5 | 15.55 | 1 228 | R-(+)-β-香茅醇 (R)-(+)-β-citronellol | C10H20O | 287.18±8.79 | — |
B6 | 24.05 | 1 551 | 橙花叔醇Nerolidol | C15H26O | 41.91±5.38 | — |
B7 | 24.66 | 1 593 | 桉油烯醇Spathulenol | C15H24O | 227.57±11.2 | — |
B8 | 24.96 | 1 595 | 榄香醇Elemol | C15H26O | 20.23±1.44 | 11.64±1.04 |
B9 | 25.64 | 1 617 | 荜澄茄油烯醇Cubenol | C15H26O | 169.20±5.01 | — |
B10 | 25.89 | 1 632 | T-衣兰油醇T-muurolol | C15H26O | 104.85±5.16 | 11.04±0.39 |
B11 | 26 | 1 639 | 香榧醇Torreyol | C15H26O | 310.20±9.14 | — |
B12 | 26.15 | 1 648 | α-毕橙茄醇α-cadinol | C15H26O | 102.08±7.54 | 6.01±0.34 |
B13 | 30.72 | 1 937 | 维西醇Victiol | C20H34O | 25.43±3.23 | 13.36±0.47 |
B14 | 32.04 | 2 032 | 13-表迈诺醇13-epimanool | C20H34O | 86.52±4.23 | — |
B15 | 36.13 | 2 406 | 脱氢枞醇Dehydroabietinol | C20H30O | 16.00±1.31 | 6.83±0.47 |
总和Total | 1 965.21±86.14 | 48.87±0.39 | ||||
萜烯酯类Terpene esters | ||||||
C1 | 17.16 | 1 289 | 乙酸冰片酯Bornyl acetate | C12H20O2 | 24.91±1.19 | — |
C2 | 18.85 | 1 352 | 乙酸松油酯Terpinyl acetate | C12H20O2 | 24.02±3.19 | — |
C3 | 19.2 | 1 366 | 乙酸香叶酯Geranyl acetate | C12H20O2 | 20.71±2.27 | — |
总和Total | 69.65±6.57 | — | ||||
其他Others | ||||||
D1 | 16.4 | 1 261 | 胡椒酮Piperitone | C10H16O | 29.63±2.12 | — |
D2 | 16.7 | 1 272 | 二氯乙酸癸酯 Decyl dichloroacetate | C12H22Cl2O2 | 61.56±3.00 | — |
D3 | 23.14 | 1 503 | 抗氧剂264 Butylated Hydroxytoluene | C15H24O | 128.78±3.51 | 6.76±0.60 |
D4 | 26.44 | 1 665 | 2, 6, 10-三甲基十四烷 2, 6, 10-Trimethyltetradecane | C17H36 | 15.03±0.45 | — |
D5 | 30.58 | 1 925 | 棕榈酸Palmitic acid | C16H32O2 | 45.63±3.39 | — |
D6 | 34.13 | 2 218 | 9-顺式-视黄醛 9-cis-Retinal | C20H28O | 19.71±2.56 | 12.16±0.39 |
D7 | 35.52 | 2 348 | (4R)-松香-7, 13-二烯-18-醛 (4R)-Abieta-7, 13-dien-18-al | C20H30O | 25.37±1.26 | 10.51±0.65 |
D8 | 36.25 | 2 419 | 新松香醛Neoabietal | C20H30O | 41.41±3.50 | — |
总和Total | 367.11±12.82 | 39.43±0.34 |
表2
不同月份香榧假种皮挥发性组分"
组分编码 No. | 化合物 Compounds | 化合物含量Compound content/(μg·g-1) | ||||
5月May | 6月June | 7月July | 8月August | 9月September | ||
萜烯类Terpenes | ||||||
A1 | α-蒎烯α-pinene | 1 347.72±134.63c | 1 367.83±46.37c | 1 508.40±61c | 2 013.85±101.72a | 1 711.06±82.19 b |
A2 | 莰烯Camphene | 130.46±8.29d | 152.19±14.32d | 205.97±6.73c | 252.81±24.23b | 458.39±20.24a |
A3 | 桧烯Sabinene | 93.09±4.72c | 92.55±6.54c | 126.68±2.16b | 149.90±12.54a | 15.04±0.98 d |
A4 | β-蒎烯β-pinene | 208.43±13.93c | 218.09±12.48c | 233.48±4.21c | 279.85±6.47b | 440.10±25.43a |
A5 | 月桂烯Myrcene | 183.37±10.31d | 201.31±12.52c | 253.93±9.39b | 310.40±3.00a | 250.91±9.53b |
A6 | 柠檬烯Limonene | 4 477.46±200.62ab | 4 075.81±210.07c | 4 304.16±159.14bc | 4 398.74±181.71abc | 4 681.36±131.08a |
A7 | 罗勒烯Ocimene | 30.46±4.24cd | 38.82±3.15bc | 41.31±6.89b | 56.26±6.61a | 21.61±0.44d |
A8 | 萜品油烯Terpinolene | 192.64±6.84b | 209.87±13.90b | 207.98±23.08b | 237.21±10.25a | 245.03±14.52a |
A9 | 别罗勒烯Alloocimene | — | — | — | — | 16.94±1.80 |
A10 | δ-榄香烯δ-elemene | 79.58±2.03b | 83.61±10.52b | 98.41±5.03a | 97.53±7.81a | 80.41±4.82b |
A11 | α-荜澄茄油烯 α-cubebene | 130.25±3.45 d | 149.48±8.58c | 175.44±11.54b | 184.45±10.61b | 214.38±9.95a |
A12 | 古巴烯Copaene | 203.59±4.39 d | 217.24±11.85 d | 252.89±5.83c | 303.44±13.75b | 380.39±18.41a |
A13 | 反式石竹烯 trans-caryophyllene | 168.02±3.41bc | 167.96±14.62bc | 185.38±9.40 ab | 190.76±14.40a | 163.13±7.72c |
A14 | (E)-β-金合欢烯 (E)-β-farnesene | 360.23±11.75c | 408.62±19.08b | 452.63±37.15a | 466.24±17.98a | 390.67±16.51bc |
A15 | δ-杜松烯δ-cadinene | 957.23±50.24b | 1034.45±46.55b | 1182.84±46.35a | 1257.25±63.22a | 814.25±34.24c |
A16 | (+)-γ-杜松烯 (+)-γ-cadinene | 63.09±2.45c | 63.76±5.17c | 96.84±0.24a | 97.13±10.18a | 75.76±6.41b |
A17 | 荜澄茄油烯Cubebene | 679.57±23.30c | 781.92±38.60b | 843.83±29.77a | 871.46±31.27a | 717.41±29.19b |
A18 | (-)-β-花柏烯 (-)-β-chamigrene | — | — | — | — | 33.37±1.40 |
A19 | α-衣兰油烯 α-muurolene | 155.45±8.11c | 152.81±9.34c | 179.50±16.11b | 183.05±12.82b | 252.45±10.03a |
A20 | β-愈创木烯 β-guaiene | — | — | 67.02±1.06a | 47.05±1.53b | 41.85±2.07c |
A21 | 松香-7, 13-二烯 Abieta-7, 13-diene | 155.67±21.53a | 162.53±5.16a | 114.84±6.28b | 131.99±2.56b | 76.68±6.86c |
总和Total | 9 616.33±461.57c | 9 578.86±413.79c | 10 531.53±402.29b | 11 529.37±456.19a | 11 081.18±398.14 ab | |
醇类Terpene alcohols | ||||||
B1 | 芳樟醇Linalol | — | 14.02±3.08c | 23.87±1.92b | 25.93±0.80 ab | 29.58±2.46a |
B2 | 冰片Borneol | — | — | 31.36±4.61c | 50.38±0.37b | 72.44±5.42a |
B3 | (-)-4-萜品醇 (-)-4-terpineol | 43.98±2.29 d | 50.95±6.24 d | 76.00±0.70c | 95.04±2.26b | 182.94±11.92a |
B4 | (+)-α-松油醇 (+)-α-terpineol | 74.09±2.46 d | 83.98±7.31 d | 137.19±8.93c | 180.94±3.88b | 289.09±10.20a |
B5 | R-(+)-β-香茅醇 (R)-(+)-β-citronellol | 33.43±1.63 e | 68.20±4.30 d | 162.56±9.23c | 229.52±10.23b | 287.18±8.79a |
B6 | 橙花叔醇Nerolidol | 33.47±1.87c | 34.48±4.42bc | 38.22±2.35bc | 46.12±5.02a | 41.91±5.38 ab |
B7 | 桉油烯醇Spathulenol | 174.36±4.92c | 176.62±10.96c | 193.38±10.89c | 261.73±12.24a | 227.57±11.20b |
B8 | 榄香醇Elemol | 23.28±0.94 ab | 22.33±4.32 ab | 25.82±0.39a | 23.04±0.71a | 20.23±1.44b |
B9 | 荜澄茄油烯醇 Cubenol | 186.14±2.30b | 167.80±8.99c | 170.08±12.34bc | 224.78±11.82a | 169.20±5.01bc |
B10 | T-衣兰油醇 T-muurolol | 111.36±4.06b | 110.95±4.69b | 110.78±2.35b | 130.14±7.65a | 104.85±5.16b |
B11 | 香榧醇Torreyol | 356.46±10.57b | 354.74±11.01b | 392.33±26.89a | 395.18±15.57a | 310.20±9.14c |
B12 | α-毕橙茄醇α-cadinol | 95.27±3.27 ab | 103.10±8.89a | 99.36±2.17 ab | 89.32±5.87b | 102.08±7.54a |
B13 | 维西醇Victiol | 87.68±5.40a | 71.25±4.77b | 67.05±5.10b | 64.83±3.13b | 25.43±3.23c |
B14 | 13-表迈诺醇 13-epimanool | 19.51±2.55b | 18.37±1.70b | 21.89±4.08b | 16.31±0.37b | 86.52±4.23a |
B15 | 脱氢枞醇 Dehydroabietinol | 16.55±3.00b | 16.58±1.83b | 14.91±0.43b | 53.26±0.41a | 16.00±1.31b |
总和Total | 1 255.58±32.74d | 1 293.38±51.50d | 1 564.79±75.51c | 1 886.53±74.14b | 1 965.21±86.14a | |
萜烯酯类Terpene esters | ||||||
C1 | 乙酸冰片酯 Bornyl acetate | — | 13.56±1.14c | 14.91±0.43c | 17.28±0.53b | 24.91±1.19a |
C2 | 乙酸松油酯 Terpinyl acetate | — | 14.88±2.34b | 22.90±2.93a | 20.16±0.62a | 24.02±3.19a |
C3 | 乙酸香叶酯 Geranyl acetate | — | 14.01±1.91b | 20.87±2.64a | 15.85±1.68b | 20.71±2.27a |
总和Total | — | 42.44±5.32c | 58.67±4.97b | 53.30±2.52b | 69.65±6.57a | |
其他Others | ||||||
D1 | 胡椒酮Piperitone | — | 12.25±1.10 d | 37.30±5.74a | 20.59±3.12c | 29.63±2.12b |
D2 | 二氯乙酸癸酯 Decyl dichloroacetate | — | 20.54±1.70c | 36.13±6.57b | 24.48±0.76c | 61.56±3.00a |
D3 | 抗氧剂264 Butylated hydroxytoluene | 132.52±4.42c | 153.51±14.69b | 307.01±5.34a | 128.70±5.56c | 128.78±3.51c |
D4 | 2, 6, 10-三甲基十四烷 2, 6, 10-trimethyltetradecane | — | — | — | 26.42±1.54a | 15.03±0.45b |
D5 | 棕榈酸Palmitic acid | — | — | — | 14.90±1.22b | 45.63±3.39a |
D6 | 9-顺式-视黄醛 9-cis-retinal | 39.85±4.80b | 58.52±1.81a | 28.72±4.39c | 22.12±2.29 d | 19.71±2.56 d |
D7 | (4R)-松香-7, 13-二烯-18-醛 (4R)-abieta-7, 13- dien-18-al | 56.06±11.30a | 54.70±9.03a | 37.74±1.01b | 24.55±4.50c | 25.37±1.26bc |
D8 | 新松香醛Neoabietal | 109.68±5.86a | 110.13±6.31a | 62.24±8.49b | 61.33±5.13b | 41.41±3.50c |
总和Total | 338.11±25.21 cd | 409.65±25.49b | 509.13±7.93a | 323.08±12.09d | 367.11±12.82c |
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