綦江皱皮木瓜果实有机酸特征性成分鉴定与 不同发育期变化规律

doi:10.3864/j.issn.0578-1752.2019.01.011

Abstract

Abstract:

【Objective】 The study was carried out to identify characteristic organic acids and disclosing their dynamic changing law of Chaenomeles speciosa fruit from Qijiang, Chongqing during its fruit developing period, so as to provide the basic data for the C. speciosa fruit organic acids metabolic research. 【Method】 By methanol extracting, methyl derivating and GC-MS detecting, the organic acids composition and their content of 8 developing period C. speciosa cv. Daluo fruit samples of Qijiang was measured. The 2012 chromatographic similarity analysis software of Chinese Pharmacopoeia Commission was used to match their common constituent peaks. The dynamic law of the total organic acids, strong-sour and weak-sour organic acids were showed in SigmaPlots10.0 software and the PCA and HCA of all the samples was processed separately by Simca-P 11.5 and SPSS 20.0 softwares. 【Result】 The total 41 common characteristic constituents, including 10 short-chain carboxylic acids, 21 long-chain fatty acids, 5 aromatic-organic acids, 3 monobasic-phenol acids and 2 amino-acids, were successfully matched among 8 TICs of different period fruit samples C. speciosa cv. Daluo from Qijiang. The baseline of all the TICs were smooth and stable, the organic acid derivatives peaks' distribution were well-distributed, and the separating-degree of samples’ peaks was high. All target components were well separated. The total organic acids content of Qijiang C. speciosa cv. Daluo fruit from 90 ^th day after its full-bloom stage to 160 ^th days showed the changing on reversed ‘Z’ that including the sharply decreasing, slowly increasing and then decreasing again. The total organic acids content was significant positive correlated with the strong sour (r=0.970) and the weak sour taste organic acids (r=0.998). At the same time, the strong sour taste organic acids were significant positive correlated with short-chain carboxylic acids (r=0.999) and positive correlated with monobasic phenol acids (r=0.747). The weak sour taste organic acids were significant positive correlated with long chain fatty acids (r=0.999). The malic acid, laevulic acid and citric acid, whose relative content sum was more than 90%, were the key ingredients of strong sour organic acids. The malic acid content had experienced a reverse ‘Z’ trend that decreased firstly (90 ^thd-120 ^thd), increased slightly (120 ^thd-130 ^thd) and decreased finally (130 ^thd-160 ^thd). The citric acid had a similar process, but the levulic acid had an obviously reverse process of changing with malic acid. Actually the levulic acid showed the increasing progress gradually. The correlation analysis showed that the strong sour taste organic acids had significant positive correlation with malate and citrate, but weakly negative correlation with levulic acid, isocitric acid, and salicylic acid. The analyzing result showed that most of the weak sour organic acids including 9-octadecenoic acid, 9,12-octadecadienoic acid, hexadecanoic acid and 10-hydroxy-hexadecanoic acid experienced the similar accumulating progress which was rapidly decreasing firstly, then slowly increased and decreased in the final stage. However, nonadecanoic acid showed an opposite process that was gradually increasing. Correlation analysis showed that the total weak sour organic acids were positively related to most of them such as 9-Octadecenoic acid and 9, 12-Octadecadienoic acid but negative to nonadecanoic acid. The PCA result by Simca-p 11.5 disclosed that PC1 and PC2 separately distributed 40.00% and 23.20% of the total variance contribution rate. The main component score of each sample showed that: S1 and S2 clustered together which decided by α-Ketoglutaric acid, malic acid, quinic acid, shikimic acid, hexadecanoic acid and linoleic acid. The S3, S4 and S5 got into one branch that mainly because of oleinic acid and 10-hydroxy-Hexadecanoic acid. The S6 was closer to S7 largely because of malonic acid, levulic acid, isocitric acid, salicyluric acid. The S8 formed a unit alone that mostly decided by succinic acid, nonadecanoic acid, tetracosanoic acid. This result was very similar to the other one that clustered by Ward's method with Squared Euclidean Distance in SPSS. 【Conclusion】 C. speciosa cv. Daluo in Qijiang,Chongqing is a typical malate-accumulating fruit. During its developing period of C. speciosa fruit, the accumulating pattern of organic acids changed from Malate-Citrate accumulating type on 90 ^th days to Levulinic acid-Malic acid - Citric acid accumulating type on 160 ^th days after its flower-blooming. The change of acid accumulation pattern played a key role in the determination of acidity and flavor quality of C. speciosa fruit in Chongqing.

Key words: Chaenomeles speciosa cv. Daluo, organic acids, GC-MS, fruit developing period, changing law

LIU ShiYao,RAN Hui,MAO YunZhi,CHEN XinYu. Identification of the Fruit Characteristic Organic Acids of Chaenomeles speciosa from Qijiang, Chongqing by GC-MS and Their Dynamic Change Researching During Its Fruit Developing Period[J].Scientia Agricultura Sinica, 2019, 52(1): 111-128.

Figures/Tables 10

Fig. 1

Table 1

MS analyzing result of organic acids methylized derivatives of 8 C. speciosa fruit samples from Qijiang, Chongqing"

成分名称 Component name		分子式 Formula	分子量 Molecular weight	平均保留时间 Mean reservation time (min)	相对标准差RSD (%)	平均相对含量 Mean relative content (%)	相对标准差 RSD (%)	酸度系数 pKa1
一	总低碳羧酸 Short-chain carboxylic acid					33.125	6.55
1	草酸 Oxalic acid	C₂H₂O₄	90.04	2.906	0.07	0.723	0.25	1.23
2	丙二酸 Malonic acid	C₃H₄O₄	104.06	4.048	0.09	0.214	0.11	2.86
3	乙酰丙酸 4-oxo-pentanoic acid	C₅H₈O₃	106.12	4.920	0.12	6.558	5.55	4.05
4	富马酸 Fumaric acid	C₄H₄O₄	116.07	5.444	0.01	0.232	0.10	3.02
5	α-酮戊二酸 2-oxo-Pentanedioic acid	C₅H₆O₅	146.1	5.582	0.07	0.188	0.09	2.47
6	苹果酸 Malic acid	C₄H₆O₅	134.09	7.064	0.21	21.473	5.56	3.46
7	琥珀酸 Succinic acid	C₄H₆O₄	118.09	7.367	0.24	0.859	0.36	4.21
8	反式乌头酸 1-Propene-1,2,3-tricarboxylic acid	C₆H₆O₆	174.11	11.618	0.30	0.067	0.04	1.95
9	柠檬酸 Citric acid	C₆H₈O₇	192.12	12.050	0.04	2.776	0.78	3.13
10	异柠檬酸 1-hydroxy-1,2,3-Propanetricarboxylic acid	C₆H₈O₇	192.14	12.614	0.08	0.036	0.02	3.13
二	总长链脂肪酸long-chain fatty acid					61.727	6.91
11	月桂酸 Dodecanoic acid（12C:0）	C₁₂H₂₄O₂	200.32	12.788	0.61	0.246	0.16	5.11
12	杜鹃花酸 Azelaic acid （9C:0）	C₉H₁₆O₄	188.22	13.089	0.82	0.153	0.06	5.07
成分名称 Component name		分子式 Formula	分子量 Molecular weight	平均保留时间 Mean reservation time (min)	相对标准差RSD (%)	平均相对含量 Mean relative content (%)	相对标准差 RSD (%)	酸度系数 pKa1
13	肉豆蔻酸 Tetradecanoic acid（14C:0）	C₁₄H₂₈O₂	228.83	15.267	0.30	0.215	0.09	5.14
14	十五烷酸 Pentadecanoic acid（15C:0）	C₁₅H₃₀O₂	242.4	16.416	0.65	0.105	0.06	5.15
15	棕榈油酸 9-Hexadecenoic acid（16C:1）	C₁₆H₃₀O₂	254.41	17.315	0.75	0.447	0.45	5.17
16	棕榈酸 Hexadecanoic acid（16C:0）	C₁₆H₃₂O₂	256.42	17.512	0.80	6.785	0.94	5.18
17	亚油酸 9,12-Octadecadienoic acid（18C:2）	C₁₈H₃₂O₂	280.45	19.287	0.55	12.079	1.98	5.20
18	油酸 9-Octadecenoic acid（18C:1）	C₁₈H₃₄O₂	282.46	19.334	0.32	25.136	7.60	5.16
19	硬脂酸 Stearic acid（18C:0）	C₁₈H₃₆O₂	284.48	19.553	0.81	0.042	0.05	5.17
20	山嵛酸 Docosanedioic acid（22C:0）	C₂₂H₄₄O₂	340.58	20.383	0.31	0.224	0.07	5.25
21	顺-11-二十碳烯酸 cis-11-Eicosenoic acid（20C:1）	C₂₀H₃₀O₂	302.45	21.219	0.24	0.532	0.24	5.21
22	花生酸 Eicosanoic acid（20C:0）	C₂₀H₄₀O₂	312.53	21.419	0.18	0.872	0.28	5.22
23	顺式-5,8,11-二十碳三烯酸（20C:3） cis-5,8,11-Eicosatrienoic acid	C₂₀H₃₄O₂	306.43	21.893	0.15	0.143	0.15	5.20
24	7,10,13-二十碳三烯酸（20C:3） 7,10,13-Eicosatrienoic acid	C₂₀H₃₄O₂	306.43	21.931	0.15	0.235	0.11	5.20
25	10,13-二十碳二烯酸（20C:2） 10,13-Eicosadienoic acid	C₂₀H₃₆O₂	308.43	22.016	0.23	1.269	0.53	5.21
26	羟基-十六烷酸（16C:0） 10-hydroxy-Hexadecanoic acid	C₁₆H₃₂O₃	262.42	22.235	0.18	5.420	2.76	5.17
27	7-羟基-十八烷酸（18C:0） 7-hydroxy-Octadecanoic acid	C₁₈H₃₄O₃	298.46	22.543	0.16	1.102	0.25	5.19
28	十九烷酸 Nonadecanoic acid（19C:0）	C₁₉H₃₈O₂	298.5	23.141	0.11	1.666	1.45	5.22
29	二十四烷酸 Tetracosanoic acid（24C:0）	C₂₄H₄₈O₂	368.64	24.998	0.20	2.411	1.02	5.27
30	9,10-二羟基-十八烷酸（18C:0） 9,10-dihydroxy-Octadecanoic acid	C₁₈H₃₄O₄	314.46	25.791	0.21	2.646	1.42	5.19
31	二十一烷酸 Heneicosanoic acid （21C:0）	C₂₁H₄₂O₂	326.56	26.110	0.30	1.663	0.41	5.23
三	芳香族有机酸Aromatic dicarboxylic acid					2.846	1.64
32	糠酸 2-Furancarboxylic acid	C₅H₄O₃	112.08	4.789	0.27	0.127	0.04	3.16
33	苯甲酸/安息香酸 Benzoic acid	C₇H₆O₂	122.12	6.656	0.12	2.079	1.31	4.21
34	DL-扁桃酸 alpha.-hydroxy-benzeneacetic acid	C₈H₈O₃	152.15	9.645	0.32	0.122	0.03	3.37
35	肉桂酸 Cinnamic acid	C₉H₈O₂	148.16	11.011	0.12	0.478	0.41	4.44
36	香草酸 vanillic acid	C₈H₈O₄	168.15	12.827	0.27	0.040	0.01	4.45
四	总一元酚酸Monobasic phenol acid					0.639	0.24
37	水杨酸 p-Hydroxybenzoic acid	C₇H₆O₃	138.12	11.874	0.32	0.228	0.17	2.98
38	奎尼酸 Quinic acid	C₇H₁₂O₆	192.17	14.010	0.68	0.333	0.17	3.70
39	莽草酸 Shikimic acid	C₇H₁₀O₅	174.15	14.808	0.79	0.079	0.05	3.87
五	总氨基酸Amino acid					0.153	0.06
40	L-天冬氨酸 L-Aspartic acid	C₄H₇NO₄	133.1	7.628	0.96	0.118	0.06	2.77
41	L-苯丙氨酸 L-Phenylalanine	C₁₀H₁₃NO₂	179.22	11.504	0.71	0.036	0.03	5.48
六	总有机酸Total organic acid					100.000

Table 1

Fig. 2

Table 2

Fig. 3

Table 3

The Pearson’s correlation analysis table of strong-sour organic acids during the fruit developing period of C. speciosa (n=8)"

	草酸	丙二酸	乙酰丙酸	富马酸	a-酮戊二酸	苹果酸	琥珀酸	反式乌头酸	柠檬酸	异柠檬酸	水杨酸	奎尼酸	莽草酸	强酸味成分
	Oxalic	Malonic acid	Pentanoic acid	Fumaric acid	2-oxo-	Malic acid	Succinic acid	Trans-aconitic acid	Citric acid	Isocitric acid	p-Hydroxybenzoic acid	Quinic acid	Shikimic acid	Strong-sour components
	acid				pentanedioic acid
草酸	1.000**	0.013	-0.22	0.683	0.647	0.537	0.354	0.245	0.185	-0.008	-0.317	0.257	0.192	0.516
Oxalic acid	1.000**	0.013	-0.22	0.683	0.647	0.537	0.354	0.245	0.185	-0.008	-0.317	0.257	0.192	0.516
丙二酸	0.013	1.000**	-0.385	-0.001	0.446	0.62	0.2	0.799*	0.935**	-0.539	-0.017	0.938**	0.94**	0.686
Malonic acid	0.013	1.000**	-0.385	-0.001	0.446	0.62	0.2	0.799*	0.935**	-0.539	-0.017	0.938**	0.94**	0.686
乙酰丙酸	-0.22	-0.385	1.000**	-0.619	-0.47	-0.606	0.148	-0.048	-0.617	0.838*	0.757*	-0.52	-0.63	-0.381
Pentanoic acid	-0.22	-0.385	1.000**	-0.619	-0.47	-0.606	0.148	-0.048	-0.617	0.838*	0.757*	-0.52	-0.63	-0.381
富马酸/延胡索酸	0.683	-0.001	-0.619	1.000**	0.684	0.662	0.372	-0.068	0.268	-0.368	-0.727*	0.179	0.228	0.504
Fumaric acid	0.683	-0.001	-0.619	1.000**	0.684	0.662	0.372	-0.068	0.268	-0.368	-0.727*	0.179	0.228	0.504
α-酮戊二酸	0.647	0.446	-0.47	0.684	1.000**	0.796*	0.213	0.434	0.575	-0.538	-0.598	0.573	0.596	0.757*
2-oxo-pentanedioic acid	0.647	0.446	-0.47	0.684	1.000**	0.796*	0.213	0.434	0.575	-0.538	-0.598	0.573	0.596	0.757*
苹果酸	0.537	0.62	-0.606	0.662	0.796*	1.000**	0.451	0.629	0.818*	-0.462*	-0.363	0.772*	0.744*	0.960**
Malic acid	0.537	0.62	-0.606	0.662	0.796*	1.000**	0.451	0.629	0.818*	-0.462*	-0.363	0.772*	0.744*	0.960**
琥珀酸	0.354	0.2	0.148	0.372	0.213	0.451	1.000**	0.452	0.208	0.249	0.152	0.155	0.072	0.554
Succinic acid	0.354	0.2	0.148	0.372	0.213	0.451	1.000**	0.452	0.208	0.249	0.152	0.155	0.072	0.554
反式乌头酸	0.245	0.799*	-0.048	-0.068	0.434	0.629	0.452	1.000**	0.731*	-0.176	0.226	0.787*	0.688	0.773*
Trans-aconitic acid	0.245	0.799*	-0.048	-0.068	0.434	0.629	0.452	1.000**	0.731*	-0.176	0.226	0.787*	0.688	0.773*
柠檬酸	0.185	0.935**	-0.617	0.268	0.575	0.818*	0.208	0.731*	1.000**	-0.611	-0.19	0.978**	0.98**	0.813*
Citric acid	0.185	0.935**	-0.617	0.268	0.575	0.818*	0.208	0.731*	1.000**	-0.611	-0.19	0.978**	0.98**	0.813*
异柠檬酸	-0.008	-0.539	0.838*	-0.368	-0.538	-0.462	0.249	-0.176	-0.611	1.000**	0.785*	-0.53	-0.681	-0.292
Isocitric acid	-0.008	-0.539	0.838*	-0.368	-0.538	-0.462	0.249	-0.176	-0.611	1.000**	0.785*	-0.53	-0.681	-0.292
水杨酸	-0.317	-0.017	0.757*	-0.727*	-0.598	-0.363	0.152	0.226	-0.19	0.785*	1.000**	-0.094	-0.25	-0.136
p-Hydroxybenzoic acid	-0.317	-0.017	0.757*	-0.727*	-0.598	-0.363	0.152	0.226	-0.19	0.785*	1.000**	-0.094	-0.25	-0.136
奎尼酸	0.257	0.938**	-0.52	0.179	0.573	0.772*	0.155	0.787*	0.978**	-0.53	-0.094	1.000**	0.978**	0.800*
Quinic acid	0.257	0.938**	-0.52	0.179	0.573	0.772*	0.155	0.787*	0.978**	-0.53	-0.094	1.000**	0.978**	0.800*
莽草酸	0.192	0.94**	-0.63	0.228	0.596	0.744*	0.072	0.688	0.98**	-0.681	-0.25	0.978**	1.000**	0.733*
Shikimic acid	0.192	0.94**	-0.63	0.228	0.596	0.744*	0.072	0.688	0.98**	-0.681	-0.25	0.978**	1.000**	0.733*
强酸性成分	0.516	0.686	-0.381	0.504	0.757*	0.96**	0.554	0.773*	0.813*	-0.292	-0.136	0.8	0.733*	1.000**
Stroung sour components	0.516	0.686	-0.381	0.504	0.757*	0.96**	0.554	0.773*	0.813*	-0.292	-0.136	0.8	0.733*	1.000**

Table 3

Fig. 4

Table 4

Fig. 5

Fig. 6

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	低碳羧酸 Short-chain carboxylic acids	长链脂肪酸 Long-chain fatty acids	芳香族有机酸 Aromatic organic acids	一元酚酸 Monobasic phenol acids	氨基酸 Amino acids	强酸味贡献成分Strong-sour taste contributing components	弱酸味贡献成分Weak-sour taste contributing components	总有机酸 Total organic acids
低碳羧酸 Short-chain carboxylic acids	1.000**	0.947**	0.314	0.732*	0.692	0.999**	0.943**	0.963**
长链脂肪酸 Long-chain fatty acids	0.947**	1.000**	0.395	0.860**	0.690	0.955**	0.999**	0.998**
芳香族有机酸 Aromatic organic acids	0.314	0.395	1.000**	0.441	-0.068	0.325	0.440	0.419
一元酚酸 Monobasic phenol acids	0.732*	0.860**	0.441	1.000**	0.747*	0.755*	0.865**	0.848**
氨基酸 Amino acids	0.692	0.690	-0.068	0.747*	1.000**	0.709*	0.672	0.683
强酸味贡献成分 Strong-sour taste contributing components	0.999**	0.955**	0.325	0.755*	0.703	1.000**	0.951**	0.970**
弱酸味贡献成分 Weak-sour taste contributing components	0.943**	0.999**	0.440	0.865**	0.672	0.951**	1.000**	0.998**
总有机酸 Total organic acids	0.963**	0.998**	0.419	0.848**	0.683	0.970**	0.998**	1.000**

	9-OA	9,12-OA	HCA	10-HHA	9,10-DOA	TA	BA	NA	HSA	10,13-EA	7-HOA	总弱酸味有机酸 Total weak-sour organic acids
9-OA	1.00**	0.887**	0.812*	0.751*	0.488	0.262	0.422	0.002	0.696	0.580	0.649	0.936**
9,12-OA	0.887**	1.00**	0.982**	0.889**	0.810*	0.583	0.338	-0.087	0.946**	0.801*	0.901**	0.987**
HCA	0.812*	0.982**	1.00**	0.923**	0.869**	0.700	0.302	-0.149	0.966**	0.783*	0.952**	0.959**
10-HHA	0.751*	0.889**	0.923**	1.00**	0.776*	0.546	0.517	-0.320	0.877**	0.611	0.855**	0.902**
9,10-DOA	0.488	0.810*	0.869**	0.776*	1.00**	0.726*	0.122	-0.114	0.913**	0.828*	0.955**	0.747*
TA	0.262	0.583	0.700	0.546	0.726*	1.00**	-0.225	-0.199	0.701	0.551	0.782*	0.490
BA	0.422	0.338	0.302	0.517	0.122	-0.225	1.00**	0.221	0.283	-0.141	0.088	0.432
NA	0.002	-0.087	-0.149	-0.320	-0.114	-0.199	0.221	1.00**	-0.141	-0.242	-0.241	-0.067
HSA	0.696	0.946**	0.966**	0.877**	0.913**	0.701	0.283	-0.141	1.00**	0.824*	0.941**	0.896**
10,13-EA	0.580	0.801*	0.783*	0.611	0.828*	0.551	-0.141	-0.242	0.824*	1.00**	0.856**	0.725*
7-HOA	0.649	0.901**	0.952**	0.855**	0.955**	0.782*	0.088	-0.241	0.941**	0.856**	1.00**	0.851**
总弱酸味有机酸 Total weak-sour organic acids	0.936**	0.987**	0.959**	0.902**	0.747*	0.490	0.432	-0.067	0.896**	0.725*	0.851**	1.00**

Identification of the Fruit Characteristic Organic Acids of Chaenomeles speciosa from Qijiang, Chongqing by GC-MS and Their Dynamic Change Researching During Its Fruit Developing Period

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