柑桔果实品质和类黄酮的含量特征及橙汁掺假检测的研究
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摘要
柑桔是世界第一大水果。2006年我国柑桔种植面积达到1814．5千公顷，居全世界第一，产量达到1789多万吨，仅次于巴西，是世界第二大柑桔生产国。柑桔类水果中富含糖、酸、维生素C、矿物质元素，还含有类黄酮、类胡萝卜素、类柠檬苦素等活性物质。这些活性物质不仅具有抗氧化、抗癌、抗炎症、抗过敏及抗菌等功效，还作为特征成分可用于柑桔育种材料初筛和橙汁掺假检测。我国几乎没有对柑桔的品质和类黄酮特征进行系统性研究，尤其对柑桔理化品质和类黄酮含量特征研究较少。因此，有必要对我国柑桔果实中类黄酮化合物的含量等进行系统研究。本文以三峡库区主栽柑桔品种的83个样品(普通甜橙31个，脐橙29个，椪柑9个，温州蜜柑9个，柚2个，柠檬3个)和国家柑桔种质资源圃的68个品种(品系)的果实为样本，对柑桔的理化品质和10种类黄酮含量进行了分析、统计，探讨柑桔品质和类黄酮与柑桔类别、品种之间的相互关系，为柑桔及相关产品的品种溯源、质量控制以及柑桔品种分类、杂种初筛等提供技术支撑。具体研究结果如下：
(1)在国内首次建立了一种高效液相色谱法在35 min内分离测试柑桔果汁和柑桔果皮中柚皮素-7-β-芸香糖苷等7种黄烷酮和甜橙黄酮等3种多甲氧基黄酮的方法，即：采用WatersSymmetry C_(18)分析柱(250 mm×4．6 mm，5μm)；流动相为乙腈-乙酸溶液进行梯度洗脱；流速为1．0 mL／min，柱温25℃，进样量20μL，检测波长287 nm和330 nm；该方法在0．01 mg／L～27 mg／L的线性范围内，具有良好的相关性(r≥0．98)，检出限为0．01-0．02mg／L。果汁中类黄酮的回收率为94．17％-106．58％，相对标准偏差为1．15％～5．41％；果皮中类黄酮的回收率为95．15％～101．19％，相对标准偏差为1．47％～3．78％。该方法简便、快速、准确，可用于柑桔中黄烷酮和多甲氧基黄酮的定量测定。
(2)分析了三峡库区83个主栽柑桔样品的品质，结果表明：橙类、宽皮柑桔、柚和柠檬的品质指标中果形指数、出汁率、可食率等指标的变异系数较小，而可溶性固形物、糖、酸等的变异系数较大。普通甜橙、脐橙、椪柑和温州蜜柑果汁中所含的类黄酮主要有黄烷酮HES、NART和DIDY以及多甲氧基黄酮SNT、NOB和TNG等，其中以HES的含量最为丰富，其次是NART、DIDY；多甲氧基黄酮SNT、NOB和TNG等在椪柑果汁中的含量最为丰富，而在普通甜橙、脐橙和温州蜜柑果汁中的含量较低。柚汁中NGIN含量最为丰富，柠檬汁中的类黄酮主要是NART。另外，研究还发现柑桔果汁类黄酮含量的变异系数也较大，但某些类黄酮间的比值的变异系数较小。
(3)采用马氏距离法对果汁理化指标和类黄酮含量指标进行简化，从22个变量中筛选出NAR／HES，DIDY等10个变量。以1，2，3，4分别表示普通甜橙、脐橙、椪柑和温州蜜柑四类，建立果汁种类的判别函数，其中：Y_1=9．990 X_(RS)+1．239 X_(Vc)+2．564 X_(SSM/TA)+0．187 X_(HES)-0．470X_(DIDY)+34．579 X_(NBL)+38．827 X_(TNG)+68．732 X_(NAR／HES)-20．022 X_(PMFs)+245．751 X_(SNT／PMFs)-141．315；Y_2=12．018 X_(RS)+1．287 X_(Vc)+3．172 X_(SSM/TA)+0．225 X_(HES)-0．453 X_(DIDY)+32．262 X_(NBL)+40．844 X_(TNG)+102．431X_(NAR／HES)-19．396 X_(PMFs)+242．498X_(SNT/PMFs)-179．077；Y_3=6．785 X_(RS)+0．561 X_(Vc)+4．710 X_(SSM/TA)+0．347X_(HES)-2．016 X_(DIDY)+136．977 X_(NBL)+102．087 X_(TNG)+139．780 X_(NAR／HES)-71．182 X_(PMFs)+296．171 X_(SNT/PMFs)-304．856；Y_4=10．506 X_(RS)+0．551 X_(Vc)+3．041 X_(SSM/TA)+0．284 X_(HES)-1．289 X_(DIDY)+40．770 X_(NBL)+38.711 X_(TNG)+184．325 X_(NAR／HES)-24．687 X_(PMFs)+140．168 X_(SNT／PMFs)-126．867。将原始数据回代入判别函数，回判的正确率达到96．15％；另外，将资源圃中的18个橙类样品的相关数据代入方程中，得到的判别结果为：有2个普通甜橙样品即冰糖橙和冰糖柑误判为脐橙样品，误判率为11．11％，可能是由于资源圃样品更复杂和无酸甜橙的固酸比指标更接近脐橙等原因导致的。
(4)分析了国家柑桔资源圃的68个品种(品系)的理化品质和类黄酮含量。结果表明宽皮柑桔由于来源复杂，样品品质差异较大，莽山野桔、扁桔等品种的食用品质较差；南丰蜜桔、本地早等食用品质较好；橙类、柚类品种的综合理化品质较好；葡萄柚可滴定酸含量高，达到1．32～1．79 g/100mL果汁(以柠檬酸计)，固酸比较低，仅为4．4～5．1；酸橙、宜昌橙的鲜食品质也较差。
柑桔资源品种果汁中黄烷酮的含量要高于多甲氧基黄酮，其中分布最广的黄烷酮是HES和NART，在68个品种中均有检出，其次是DIDY、NHES、NGIN，而HET和NGEN较少检出；SNT、NBL和TNG等多甲氧基黄酮分布也较广。不同品种或品系柑桔果汁中类黄酮的种类和含量也不尽相同，宽皮柑桔及其杂种中的类黄酮主要有HES、NART、DIDY、SNT、NBL和TNG等，其中以HES的平均含量最高，达188．98 mg／L，其次为NART、DIDY等，NHES、NGIN、NGEN和HET仅在部分宽皮柑桔样品中检出；橙类资源品种主要含NART、HES、DIDY、SNT、NBL和TNG等类黄酮，其中以HES含量最高，纽荷尔脐橙中的含量尤为丰富；柚类果汁中的类黄酮主要为NGIN、HES和NART，其中以NGIN含量最为丰富，平均含量达77．88 mg／L；葡萄柚果汁中的类黄酮主要为NGIN、NART、NHES、HES和DIDY等，含量最丰富的是NGIN，平均含量达到651．88 mg／L；柠檬果汁中主要类黄酮为HES、NGIN和NRAT，其中HES含量最高，平均含量达到55．87 mg／L；酸橙中类黄酮有NGIN、NART、HES、NHES和DIDY，其中以NGIN的含量最高，平均达到173．87 mg/L；宜昌橙所含类黄酮的种类包括NGIN、HES、NART、NHES、NGEN、HET和SNT等，其中以NGIN的含量(177．60mg／L)最为丰富。
另外，在资源品种中发现了一些具有开发利用价值的我国特有或古老的品种。如莽山野桔中DIDY(221．54 mg/L)远高于其它品种，含量第二丰富的纽荷尔脐橙中DIDY也仅只有莽山野桔中的21％，是资源品种平均含量的15倍；扁桔的多甲氧其黄酮尤其是NOB的含量也远远高于其它品种，是武隆酸桔(含量第二)NOB的2．3倍，是资源品种平均含量的15倍；广西粗柠檬中SNT的含量也高达12．69 mg／L，远远高于其它品种。DIDY、NOB和SNT等生物活性成分具有抗癌、抗氧化等多种功能作用，因此这些品种具有良好的开发前景和利用价值。
(5)应用方差分析法从27个柑桔果汁理化和类黄酮含量指标中提取出9个主成分，并计算出每个样品的各主成分分值。对样品的主成分分值进行快速聚类分析，发现对柚、柠檬等的分类效果较好，而宽皮柑桔和橙类效果较差，这从侧面反应出宽皮柑桔和橙类的亲缘关系较近。分层聚类的结果表明，莽山野桔与其它柑桔品种距离最远，其次是扁桔、柚、金山橙、朱桔和曼桔等。该结果与柑桔品种分类的结果较一致，表明柑桔果汁的理化品质和类黄酮等指标能在一定程度上反映柑桔品种品系间的亲缘关系。
(6)应用Logit模型，从果汁的25个变量指标中筛选出5个变量X_(DIDY)、X_(NAR／HES)、X_(PMFs)、X_(SNT／PMFs)和X_(NBL／PMFs)，建立了原橙汁的掺假判断模型：y=1-e~(-x)/1+e~(-x)其中，x=0．603X_(DIDY)=142．058X_(NAR/HES)+2．430X_(PMFs)+54．384X_(SNT／PMFs)-143．634X_(NBL/PMFs)+51．671并根据拟合结果，确定30％为门槛值，即当拟合值低于30％时，认为样品为掺杂样品，当拟合值高于70％时，认为样品为原橙汁；介于30％～70％时则不能判断。因此，当原橙汁的掺杂量低于5％时，该模型不能判断出其是否掺杂；掺杂量大于或等于5％，该模型能判断出橙汁掺杂。
本论文有以下几个方面的创新：
(1)首次系统地对我国柑桔主栽品种和资源品种(品系)果汁的品质和类黄酮含量特征进行了分析，初步建立相对完整的柑桔果汁中类黄酮种类和含量数据库，为我国柑桔区域规划制订、品种选育和加工原料的选择等积累了基础资料；
(2)首次建立基于类黄酮为评价指标的适宜我国橙汁特征的真实度评价模型，为我国修订橙汁含量检测标准、制定橙汁产品标准等提供依据。
本论文为科技部“十一五”科技支撑计划“橙汁全程质量安全控制及检测技术开发研究”(2007BAD47807)和科技部科研院所社会公益研究专项“柑桔产品质量检测关键技术及标准研究”(2004DIB4J147)的部分研究内容。
Citrus is the biggest fruit in the world. In China, the planting area of Citrus in 2006 has come to 1814.5 thousand hectare and the production was more than 1789 million metric tons, which was the first and second, next to Brazil in the world respectively. The biochemical materials in citrus fruits such as flavonoids, carotenoids and limonoides not only have active effects of anti-oxidantion, anti-cancer, prevention of circulatory disorders, anti-inflammatory, anti-allergic, anti-bacterial and so on but also can be used as the marks of screening species initially and adulteration detection of orange juice. The physical & chemical characters and contents of flavanoids of 83 citrus samples cultivated in three gorges districts and 68 varieties collected from Chinese citrus germplasm resource garden were analyzed. The variation of the every index was analyzed by statistical software, and based on results, the classification function of the main cultivated varieties, the relative relation among different varieties revealed by the character of juice, the model of adulteration for orange juice were discussed.. The main results of this paper are as follows.
1) A RP-HPLC method was developed for simultaneous determination of 7 flavanones (narirutin, naringin, hesperidin, neohesperidin, didymin, naringenin, hesperetin) and 3 polymethoxylated flavones (sinensetin, nobiletin, and tangeretin) in citrus within 35 minutes. A waters Symmetry C18 column was used with 0.2% acetic acid solvent and acetonitrile as mobile phase at a flow rate of 1.0 mL /min. The column temperature was 25℃and the UV detection wavelengths were 287 nm and 330 nm. The flavonoids were qualified by external standard, and the linear ranges of 10 flavonoids were 0.01～20mg/L (r≥0.9988) , and the detection limits were 0.005～0.01lmg / L. The average recoveries of flavonoids in juice and dry peel power were 94.20%～106.58% and 95.15%～101.19% respectively; RSD were 1.15%～5.41% and 1.47%～3.78% respectively. The results indicate that the method is fast, sensitive, reproducible and practical for the routine analysis of flavonoids in citrus.
2) The physical & chemical character and contents of flavanoids of 83 citrus samples cultivated in three gorges districts were analyzed. The results showed that the soluble solids, sugar and acid varied greatly and the coefficient of variability of the index of fruit shape, rate of juice and rate of edible material were smaller than other characters in orange, madarin, pumelo and lemon. The main flavonoids in juice of common sweet orange, navel orange, Ponkan and Satsuma mandarins were hesperidin, narirutin, didymin, sinensetin , nobiletin and tangeretin. The amount of hesperidin was heighest, then was narirutin and didymin. The amount of polymethoxylated flavones of sinensetin , nobiletin and tangeretin was richest in Ponkan juice, which amount to 8.50 mg/L, but they were lower in common orange, navel orange and Satsuma mandarins. The main flavonoids in juice of pumelo and lemon were narirutin, naringin and hesperidin, and the highest in pumelo was naringin and the highest in lemon was narirutin. The results showed the amount of flavonoids varied greatly but the ratio of flavonoids varied little.
3)The variables of physical & chemical character and contents of flavanoids were simplified by Mahalanobis distance method and selected 10 variables from 22 variables. The classification functions of common orange, navel orange, Ponkan and Satsuma mandarins were established based on the 10 variables. Y1=9.990 X_(RS) +1.239 X_(Vc)+2.564 X_(SSM/TA)+0.187 X_(HES) -0.470 X_(DIDY)+34.579 X_(NBL)+38.827 X_(TNG)+68.732 X_(NAR/HES)-20.022 X_(APMFs)+245.751 X_(SNT/PMFs) -141.315; Y2=12.018 X_(RS)+ 1.287 X_(Vc)+3.172 X_(SSM/TA)+0.225 X_(HES)-0.453 X_(DIDY)+32.262 X_(NBL)+40.844 X_(TNG)+102.431 X_(NAR/HES)-19.396 X_(PMFs)+242.498X_(SNT/PMFs)-79.077; Y3=6.785 X_(RS)+0.561 X_(Vc)+4.710 X_(SSM/TA)+0.347 X_(HES)-2.016X_(DIDY) +136.977 X_(NBL)+102.087 X_(TNG)+139.780 X_(NAR/HES)-71.182 X_(PMFs)+296.171 X+_(SNT/PMFs)-304.856;Y4 =10.506 X_(RS)+0.551 X_(Vc)+3.041 X_(ASSM/TA)+0.284 X_(HES)-1.289 X_(DIDY)+40.770 X_(NBL)+38.71 1 X_(TNG)+ 184.325 X_(NAR/HES)-24.687 X_(PMFs)+140.168 X_(SNT/PMFs)-126.867. The orginal counts were used to test the classification functions, and the 96.15% were classified correctly. The data of 18 orange samples from Chinese Citrus Germplasm Resource Garden were used to test the classification functions, and two common oranges were classified as Navel orange. The reason may be the samples were complicated and the index such as SSM/TA of acidless orange was similar to Navel's.
4) The physical & chemical character and contents of flavanoids of 68 citrus biotypes from Chinese citrus germplasm resource garden were analyzed. The results showed the physical & chemical character of C. reticulata Blanco varied largely because the source of the were complicated. The edible qualities of C. kinokuni and Pentitsao were good, while wild Mangshan tangerine、Bian Ju were not suitable for edit while they were good resources of bioactive constitutents. The physical & chemical character of orange and pomelo were better. The content of titratable acid of grapefruit juice was high, which reaching 1.32～1.79g/100mL, while the ration of soluble solid material and titratable acid was only 4.4～5.1. The sour orange was not suitable for edible too while it was a good product for pharmaceutical use and its flower, leave and fruit can be used as material to extract essential oil. The edible quality of C. ichangensis was bad and can only be used as rootstock.
The contents of flavanone glycosides were higher than aglycones in all biotypes. In these flavanone glycosides, hesperidin and narirutin were distributed wildly and they were detested in every biotype, then didymin, neohesperidin and naringin.The aglycones, Sinensetin, nobiletin and tangeretin were also distributed wildly, but naringenin and hesperetin were only detected in little varieties. The types and contents of flavonoids in different biotypes varied largely. The main flavonoids in C. reticulata Blanco and hybrids were hesperidin, narirutin, didymin, sinensetin, nobiletin and tangeretin, and the highest was hesperidin,which got to 188.98 mg/L, then was narirutin, didymin in turn.Neohesperidin, naringin, naringenin and hesperetin only were detected in little varieties. The main flavonoids in C. sinensis Osbeck were hesperidin, narirutin, didymin, sinensetin, nobiletin and tangeretin, and the highest was hesperidin too. The main flavonoids in pumelo were naringin, hesperidin and narirutin, and the highest was naringin, which amount to 77.88 mg/L. The main flavonoids in grapefruit were naringin, hesperidin, narirutin, neo hesperidin, hesperetin and didymin, and the content of naringin (651.88 mg/L) was highest. The main flavonoids in lemon were hesperidin, naringin and narirutin, and the highest was hesperidin, with the average contents of 55.87 mg/L. The main flavonoids in sour orange were naringin, narirutin, and didymin, and the highest was naringin, with the average contents of 173.87 mg/L. The main flavonoids in C. ichangensis were included naringin, hesperidin, narirutin, neohesperidin, naringenin, hesperetin and sinensetin, and the richest was naringin(177.60 mg/L).
5)Nine principal component were got from 27 indexes about physical & chemical character and contents of flavanoids by analysis of variance, and the score of PCA were calculated. The PCA scores of sample were used to. The results of K-cluster analysis showed that pomelo and lemon could be separated from other species respectively, and the C. reticulata Blanco and C. sinensis Osbeck couldn't be separated. The graph of hierarchical cluster, which indicated the distances between the species, showed that Mangshan wild orange had the longest distance from the other species, then was Bian Ju, pumelo, Jianshan orange, Zhu Ju, Man Ju and so on. The Euclidean distance between samples of C. sinensis Osbeck were very closed, Tian Cao tanglo also had the short Euclidean distance to C. sinensis Osbeck. The Euclidean distances of samples of grapefruits were short, and Euclidean distances among grapefruits, sour orange, C. ichangensis were short too.
6) Five varieties were selected from 25 by Z-statistics, which were X_(DIDY)、X_(NAR/HES)、X_(PMFs)、X_(SNT/PMFs) and X_(NBL/PMF)(actually they were six initial index). An alteration model for orange juice was established by logit model using these selected varieties. The alteration model isy=1-e~(-x)/1+e~(-x)In which x=0.603X_(DIDY)-142.058X_(NAR/HES)+2.430X_(PMFs)+54.384X_(SNT/PMFs)-143.634X_(NBL/PMFs)+5 1.671
As the fitted results of all manderine, hybrid juice were below 30%, and the fitted results of most common orange juice were above 70%, so threshold value was decided as 30%. When the fitted figure less than 30%, the sample was considered alteration by the model, when the fitted results figure more than 30%, the sample was considered pure orange, but when the figure below 70% and above, the sample cannot be discriminated by the model.
This dissertation possesses the following innovations: (1)The physical & chemical character and contents of flavanoids of main cultivated citrus samples and citrus biotypes were analyzed systematically. The database for types and contents of flavonoids of citrus juice in China were established initially, which could be basic information for identification of juice adulteration, product standards development, screening biotypes and choosing right processing materials.(2) Flavonoids were first used as evaluation index to establish the model for evaluation the authentic of orange juice suitable for China.
(1)在国内首次建立了一种高效液相色谱法在35 min内分离测试柑桔果汁和柑桔果皮中柚皮素-7-β-芸香糖苷等7种黄烷酮和甜橙黄酮等3种多甲氧基黄酮的方法，即：采用WatersSymmetry C_(18)分析柱(250 mm×4．6 mm，5μm)；流动相为乙腈-乙酸溶液进行梯度洗脱；流速为1．0 mL／min，柱温25℃，进样量20μL，检测波长287 nm和330 nm；该方法在0．01 mg／L～27 mg／L的线性范围内，具有良好的相关性(r≥0．98)，检出限为0．01-0．02mg／L。果汁中类黄酮的回收率为94．17％-106．58％，相对标准偏差为1．15％～5．41％；果皮中类黄酮的回收率为95．15％～101．19％，相对标准偏差为1．47％～3．78％。该方法简便、快速、准确，可用于柑桔中黄烷酮和多甲氧基黄酮的定量测定。
(2)分析了三峡库区83个主栽柑桔样品的品质，结果表明：橙类、宽皮柑桔、柚和柠檬的品质指标中果形指数、出汁率、可食率等指标的变异系数较小，而可溶性固形物、糖、酸等的变异系数较大。普通甜橙、脐橙、椪柑和温州蜜柑果汁中所含的类黄酮主要有黄烷酮HES、NART和DIDY以及多甲氧基黄酮SNT、NOB和TNG等，其中以HES的含量最为丰富，其次是NART、DIDY；多甲氧基黄酮SNT、NOB和TNG等在椪柑果汁中的含量最为丰富，而在普通甜橙、脐橙和温州蜜柑果汁中的含量较低。柚汁中NGIN含量最为丰富，柠檬汁中的类黄酮主要是NART。另外，研究还发现柑桔果汁类黄酮含量的变异系数也较大，但某些类黄酮间的比值的变异系数较小。
(3)采用马氏距离法对果汁理化指标和类黄酮含量指标进行简化，从22个变量中筛选出NAR／HES，DIDY等10个变量。以1，2，3，4分别表示普通甜橙、脐橙、椪柑和温州蜜柑四类，建立果汁种类的判别函数，其中：Y_1=9．990 X_(RS)+1．239 X_(Vc)+2．564 X_(SSM/TA)+0．187 X_(HES)-0．470X_(DIDY)+34．579 X_(NBL)+38．827 X_(TNG)+68．732 X_(NAR／HES)-20．022 X_(PMFs)+245．751 X_(SNT／PMFs)-141．315；Y_2=12．018 X_(RS)+1．287 X_(Vc)+3．172 X_(SSM/TA)+0．225 X_(HES)-0．453 X_(DIDY)+32．262 X_(NBL)+40．844 X_(TNG)+102．431X_(NAR／HES)-19．396 X_(PMFs)+242．498X_(SNT/PMFs)-179．077；Y_3=6．785 X_(RS)+0．561 X_(Vc)+4．710 X_(SSM/TA)+0．347X_(HES)-2．016 X_(DIDY)+136．977 X_(NBL)+102．087 X_(TNG)+139．780 X_(NAR／HES)-71．182 X_(PMFs)+296．171 X_(SNT/PMFs)-304．856；Y_4=10．506 X_(RS)+0．551 X_(Vc)+3．041 X_(SSM/TA)+0．284 X_(HES)-1．289 X_(DIDY)+40．770 X_(NBL)+38.711 X_(TNG)+184．325 X_(NAR／HES)-24．687 X_(PMFs)+140．168 X_(SNT／PMFs)-126．867。将原始数据回代入判别函数，回判的正确率达到96．15％；另外，将资源圃中的18个橙类样品的相关数据代入方程中，得到的判别结果为：有2个普通甜橙样品即冰糖橙和冰糖柑误判为脐橙样品，误判率为11．11％，可能是由于资源圃样品更复杂和无酸甜橙的固酸比指标更接近脐橙等原因导致的。
(4)分析了国家柑桔资源圃的68个品种(品系)的理化品质和类黄酮含量。结果表明宽皮柑桔由于来源复杂，样品品质差异较大，莽山野桔、扁桔等品种的食用品质较差；南丰蜜桔、本地早等食用品质较好；橙类、柚类品种的综合理化品质较好；葡萄柚可滴定酸含量高，达到1．32～1．79 g/100mL果汁(以柠檬酸计)，固酸比较低，仅为4．4～5．1；酸橙、宜昌橙的鲜食品质也较差。
柑桔资源品种果汁中黄烷酮的含量要高于多甲氧基黄酮，其中分布最广的黄烷酮是HES和NART，在68个品种中均有检出，其次是DIDY、NHES、NGIN，而HET和NGEN较少检出；SNT、NBL和TNG等多甲氧基黄酮分布也较广。不同品种或品系柑桔果汁中类黄酮的种类和含量也不尽相同，宽皮柑桔及其杂种中的类黄酮主要有HES、NART、DIDY、SNT、NBL和TNG等，其中以HES的平均含量最高，达188．98 mg／L，其次为NART、DIDY等，NHES、NGIN、NGEN和HET仅在部分宽皮柑桔样品中检出；橙类资源品种主要含NART、HES、DIDY、SNT、NBL和TNG等类黄酮，其中以HES含量最高，纽荷尔脐橙中的含量尤为丰富；柚类果汁中的类黄酮主要为NGIN、HES和NART，其中以NGIN含量最为丰富，平均含量达77．88 mg／L；葡萄柚果汁中的类黄酮主要为NGIN、NART、NHES、HES和DIDY等，含量最丰富的是NGIN，平均含量达到651．88 mg／L；柠檬果汁中主要类黄酮为HES、NGIN和NRAT，其中HES含量最高，平均含量达到55．87 mg／L；酸橙中类黄酮有NGIN、NART、HES、NHES和DIDY，其中以NGIN的含量最高，平均达到173．87 mg/L；宜昌橙所含类黄酮的种类包括NGIN、HES、NART、NHES、NGEN、HET和SNT等，其中以NGIN的含量(177．60mg／L)最为丰富。
另外，在资源品种中发现了一些具有开发利用价值的我国特有或古老的品种。如莽山野桔中DIDY(221．54 mg/L)远高于其它品种，含量第二丰富的纽荷尔脐橙中DIDY也仅只有莽山野桔中的21％，是资源品种平均含量的15倍；扁桔的多甲氧其黄酮尤其是NOB的含量也远远高于其它品种，是武隆酸桔(含量第二)NOB的2．3倍，是资源品种平均含量的15倍；广西粗柠檬中SNT的含量也高达12．69 mg／L，远远高于其它品种。DIDY、NOB和SNT等生物活性成分具有抗癌、抗氧化等多种功能作用，因此这些品种具有良好的开发前景和利用价值。
(5)应用方差分析法从27个柑桔果汁理化和类黄酮含量指标中提取出9个主成分，并计算出每个样品的各主成分分值。对样品的主成分分值进行快速聚类分析，发现对柚、柠檬等的分类效果较好，而宽皮柑桔和橙类效果较差，这从侧面反应出宽皮柑桔和橙类的亲缘关系较近。分层聚类的结果表明，莽山野桔与其它柑桔品种距离最远，其次是扁桔、柚、金山橙、朱桔和曼桔等。该结果与柑桔品种分类的结果较一致，表明柑桔果汁的理化品质和类黄酮等指标能在一定程度上反映柑桔品种品系间的亲缘关系。
(6)应用Logit模型，从果汁的25个变量指标中筛选出5个变量X_(DIDY)、X_(NAR／HES)、X_(PMFs)、X_(SNT／PMFs)和X_(NBL／PMFs)，建立了原橙汁的掺假判断模型：y=1-e~(-x)/1+e~(-x)其中，x=0．603X_(DIDY)=142．058X_(NAR/HES)+2．430X_(PMFs)+54．384X_(SNT／PMFs)-143．634X_(NBL/PMFs)+51．671并根据拟合结果，确定30％为门槛值，即当拟合值低于30％时，认为样品为掺杂样品，当拟合值高于70％时，认为样品为原橙汁；介于30％～70％时则不能判断。因此，当原橙汁的掺杂量低于5％时，该模型不能判断出其是否掺杂；掺杂量大于或等于5％，该模型能判断出橙汁掺杂。
本论文有以下几个方面的创新：
(1)首次系统地对我国柑桔主栽品种和资源品种(品系)果汁的品质和类黄酮含量特征进行了分析，初步建立相对完整的柑桔果汁中类黄酮种类和含量数据库，为我国柑桔区域规划制订、品种选育和加工原料的选择等积累了基础资料；
(2)首次建立基于类黄酮为评价指标的适宜我国橙汁特征的真实度评价模型，为我国修订橙汁含量检测标准、制定橙汁产品标准等提供依据。
本论文为科技部“十一五”科技支撑计划“橙汁全程质量安全控制及检测技术开发研究”(2007BAD47807)和科技部科研院所社会公益研究专项“柑桔产品质量检测关键技术及标准研究”(2004DIB4J147)的部分研究内容。
Citrus is the biggest fruit in the world. In China, the planting area of Citrus in 2006 has come to 1814.5 thousand hectare and the production was more than 1789 million metric tons, which was the first and second, next to Brazil in the world respectively. The biochemical materials in citrus fruits such as flavonoids, carotenoids and limonoides not only have active effects of anti-oxidantion, anti-cancer, prevention of circulatory disorders, anti-inflammatory, anti-allergic, anti-bacterial and so on but also can be used as the marks of screening species initially and adulteration detection of orange juice. The physical & chemical characters and contents of flavanoids of 83 citrus samples cultivated in three gorges districts and 68 varieties collected from Chinese citrus germplasm resource garden were analyzed. The variation of the every index was analyzed by statistical software, and based on results, the classification function of the main cultivated varieties, the relative relation among different varieties revealed by the character of juice, the model of adulteration for orange juice were discussed.. The main results of this paper are as follows.
1) A RP-HPLC method was developed for simultaneous determination of 7 flavanones (narirutin, naringin, hesperidin, neohesperidin, didymin, naringenin, hesperetin) and 3 polymethoxylated flavones (sinensetin, nobiletin, and tangeretin) in citrus within 35 minutes. A waters Symmetry C18 column was used with 0.2% acetic acid solvent and acetonitrile as mobile phase at a flow rate of 1.0 mL /min. The column temperature was 25℃and the UV detection wavelengths were 287 nm and 330 nm. The flavonoids were qualified by external standard, and the linear ranges of 10 flavonoids were 0.01～20mg/L (r≥0.9988) , and the detection limits were 0.005～0.01lmg / L. The average recoveries of flavonoids in juice and dry peel power were 94.20%～106.58% and 95.15%～101.19% respectively; RSD were 1.15%～5.41% and 1.47%～3.78% respectively. The results indicate that the method is fast, sensitive, reproducible and practical for the routine analysis of flavonoids in citrus.
2) The physical & chemical character and contents of flavanoids of 83 citrus samples cultivated in three gorges districts were analyzed. The results showed that the soluble solids, sugar and acid varied greatly and the coefficient of variability of the index of fruit shape, rate of juice and rate of edible material were smaller than other characters in orange, madarin, pumelo and lemon. The main flavonoids in juice of common sweet orange, navel orange, Ponkan and Satsuma mandarins were hesperidin, narirutin, didymin, sinensetin , nobiletin and tangeretin. The amount of hesperidin was heighest, then was narirutin and didymin. The amount of polymethoxylated flavones of sinensetin , nobiletin and tangeretin was richest in Ponkan juice, which amount to 8.50 mg/L, but they were lower in common orange, navel orange and Satsuma mandarins. The main flavonoids in juice of pumelo and lemon were narirutin, naringin and hesperidin, and the highest in pumelo was naringin and the highest in lemon was narirutin. The results showed the amount of flavonoids varied greatly but the ratio of flavonoids varied little.
3)The variables of physical & chemical character and contents of flavanoids were simplified by Mahalanobis distance method and selected 10 variables from 22 variables. The classification functions of common orange, navel orange, Ponkan and Satsuma mandarins were established based on the 10 variables. Y1=9.990 X_(RS) +1.239 X_(Vc)+2.564 X_(SSM/TA)+0.187 X_(HES) -0.470 X_(DIDY)+34.579 X_(NBL)+38.827 X_(TNG)+68.732 X_(NAR/HES)-20.022 X_(APMFs)+245.751 X_(SNT/PMFs) -141.315; Y2=12.018 X_(RS)+ 1.287 X_(Vc)+3.172 X_(SSM/TA)+0.225 X_(HES)-0.453 X_(DIDY)+32.262 X_(NBL)+40.844 X_(TNG)+102.431 X_(NAR/HES)-19.396 X_(PMFs)+242.498X_(SNT/PMFs)-79.077; Y3=6.785 X_(RS)+0.561 X_(Vc)+4.710 X_(SSM/TA)+0.347 X_(HES)-2.016X_(DIDY) +136.977 X_(NBL)+102.087 X_(TNG)+139.780 X_(NAR/HES)-71.182 X_(PMFs)+296.171 X+_(SNT/PMFs)-304.856;Y4 =10.506 X_(RS)+0.551 X_(Vc)+3.041 X_(ASSM/TA)+0.284 X_(HES)-1.289 X_(DIDY)+40.770 X_(NBL)+38.71 1 X_(TNG)+ 184.325 X_(NAR/HES)-24.687 X_(PMFs)+140.168 X_(SNT/PMFs)-126.867. The orginal counts were used to test the classification functions, and the 96.15% were classified correctly. The data of 18 orange samples from Chinese Citrus Germplasm Resource Garden were used to test the classification functions, and two common oranges were classified as Navel orange. The reason may be the samples were complicated and the index such as SSM/TA of acidless orange was similar to Navel's.
4) The physical & chemical character and contents of flavanoids of 68 citrus biotypes from Chinese citrus germplasm resource garden were analyzed. The results showed the physical & chemical character of C. reticulata Blanco varied largely because the source of the were complicated. The edible qualities of C. kinokuni and Pentitsao were good, while wild Mangshan tangerine、Bian Ju were not suitable for edit while they were good resources of bioactive constitutents. The physical & chemical character of orange and pomelo were better. The content of titratable acid of grapefruit juice was high, which reaching 1.32～1.79g/100mL, while the ration of soluble solid material and titratable acid was only 4.4～5.1. The sour orange was not suitable for edible too while it was a good product for pharmaceutical use and its flower, leave and fruit can be used as material to extract essential oil. The edible quality of C. ichangensis was bad and can only be used as rootstock.
The contents of flavanone glycosides were higher than aglycones in all biotypes. In these flavanone glycosides, hesperidin and narirutin were distributed wildly and they were detested in every biotype, then didymin, neohesperidin and naringin.The aglycones, Sinensetin, nobiletin and tangeretin were also distributed wildly, but naringenin and hesperetin were only detected in little varieties. The types and contents of flavonoids in different biotypes varied largely. The main flavonoids in C. reticulata Blanco and hybrids were hesperidin, narirutin, didymin, sinensetin, nobiletin and tangeretin, and the highest was hesperidin,which got to 188.98 mg/L, then was narirutin, didymin in turn.Neohesperidin, naringin, naringenin and hesperetin only were detected in little varieties. The main flavonoids in C. sinensis Osbeck were hesperidin, narirutin, didymin, sinensetin, nobiletin and tangeretin, and the highest was hesperidin too. The main flavonoids in pumelo were naringin, hesperidin and narirutin, and the highest was naringin, which amount to 77.88 mg/L. The main flavonoids in grapefruit were naringin, hesperidin, narirutin, neo hesperidin, hesperetin and didymin, and the content of naringin (651.88 mg/L) was highest. The main flavonoids in lemon were hesperidin, naringin and narirutin, and the highest was hesperidin, with the average contents of 55.87 mg/L. The main flavonoids in sour orange were naringin, narirutin, and didymin, and the highest was naringin, with the average contents of 173.87 mg/L. The main flavonoids in C. ichangensis were included naringin, hesperidin, narirutin, neohesperidin, naringenin, hesperetin and sinensetin, and the richest was naringin(177.60 mg/L).
5)Nine principal component were got from 27 indexes about physical & chemical character and contents of flavanoids by analysis of variance, and the score of PCA were calculated. The PCA scores of sample were used to. The results of K-cluster analysis showed that pomelo and lemon could be separated from other species respectively, and the C. reticulata Blanco and C. sinensis Osbeck couldn't be separated. The graph of hierarchical cluster, which indicated the distances between the species, showed that Mangshan wild orange had the longest distance from the other species, then was Bian Ju, pumelo, Jianshan orange, Zhu Ju, Man Ju and so on. The Euclidean distance between samples of C. sinensis Osbeck were very closed, Tian Cao tanglo also had the short Euclidean distance to C. sinensis Osbeck. The Euclidean distances of samples of grapefruits were short, and Euclidean distances among grapefruits, sour orange, C. ichangensis were short too.
6) Five varieties were selected from 25 by Z-statistics, which were X_(DIDY)、X_(NAR/HES)、X_(PMFs)、X_(SNT/PMFs) and X_(NBL/PMF)(actually they were six initial index). An alteration model for orange juice was established by logit model using these selected varieties. The alteration model isy=1-e~(-x)/1+e~(-x)In which x=0.603X_(DIDY)-142.058X_(NAR/HES)+2.430X_(PMFs)+54.384X_(SNT/PMFs)-143.634X_(NBL/PMFs)+5 1.671
As the fitted results of all manderine, hybrid juice were below 30%, and the fitted results of most common orange juice were above 70%, so threshold value was decided as 30%. When the fitted figure less than 30%, the sample was considered alteration by the model, when the fitted results figure more than 30%, the sample was considered pure orange, but when the figure below 70% and above, the sample cannot be discriminated by the model.
This dissertation possesses the following innovations: (1)The physical & chemical character and contents of flavanoids of main cultivated citrus samples and citrus biotypes were analyzed systematically. The database for types and contents of flavonoids of citrus juice in China were established initially, which could be basic information for identification of juice adulteration, product standards development, screening biotypes and choosing right processing materials.(2) Flavonoids were first used as evaluation index to establish the model for evaluation the authentic of orange juice suitable for China.
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