金花茶和白色山茶及其3个杂交品种类黄酮成分与花色的关系
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摘要
以金花茶(Camellianitidissima,深黄色)和山茶(C.japonica,白色)及其杂交品种(淡黄色)为试验材料,按照CIE L~*a~*b~*表色系法测量其花色,利用超高效液相色谱—四极杆—飞行时间质谱(UPLC-Q-TOF-MS)联用技术定性定量分析其类黄酮成分与含量,运用多元线性回归方法研究其花色与类黄酮成分之间的关系。在金花茶和白色山茶及其3个杂交品种中共检测到10种类黄酮成分,其中天竺葵素–3–O–葡萄糖苷(Pg3G)、木犀草素–7–O–芸香糖苷(Lu7R)、圣草素(Er)和染料木苷(Gin)为金花茶中首次发现,而在白色山茶品种‘银白查理斯’和‘白凤’中未检测到Pg3G、Er和Gin,Lu7R含量极低。金花茶中主要成分为槲皮素–3–O–葡萄糖苷(Qu3G)、槲皮素–3–O–芸香糖苷(Qu3R)、槲皮素–7–O–葡萄糖苷(Qu7G)、山萘酚–3–O–葡萄糖苷(Km3G)、Pg3G和Lu7R。杂交品种中木犀草素(Lu)、山萘酚(Km)和Er含量高于双亲,其余成分及类黄酮总量介于双亲之间。Qu3G和Qu3R是决定金花茶及其与白色山茶杂交的品种花瓣呈现黄色的主要成分,Qu3G和Qu3R含量的增加导致花色显著变黄;Qu3G含量的积累显著增加了花色鲜艳程度,Pg3G影响色调。
The flower colors,flavonoid components and contents in dark yellow Camellia nitidissima,white C. japonica and their pale yellow hybrid cultivars were studied. The flower colors were measured by CIE L~*a~*b~* scale,and flavonoids were qualitatively and quantitatively analyzed by ultra-performance liquid chromatography quadrupole-time-of-flight mass spectrometry. The relationship between flower colors and flavonoid components was explored by analyzed by multiple liner regression analyses. Ten flavonoids were detected in C. nitidissima,white C. japonica and their three hybrid cultivars. The flavonoids including pelargonium-3-O-glucoside(Pg3G),luteolin-7-O-rutinoside(Lu7 R),eriodictyol(Er)and genistin(Gin)were identified in C. nitidissima for the first time. Pg3G,Er and Gin were not determined in white C. japonica‘Yinbai Chalis' and‘Baifeng',and the contents of Lu7 R were extremely low. The main components of C. nitidissima were quercetin-3-O-glucoside( Qu3G),quercetin-3-O-rutinoside(Qu3R),quercetin-7-O-glucoside(Qu7 G),kaempferol-3-O-glucoside(Km3G),Pg3G and Lu7 R. The contents of luteolin(Lu),kaempferol(Km)and Er in hybrid cultivars surpassed their parents,and those of the rest and total flavonoids were between their parents. Qu3G and Qu3R were the important components which decided the yellow color of C. nitidissima and its hybrid cultivars,and the increase of their contents caused the flower color to remarkably turn yellow. The accumulation of Qu3G significantly enhanced the brilliance of flower color,and Pg3G affected the color tone.
The flower colors,flavonoid components and contents in dark yellow Camellia nitidissima,white C. japonica and their pale yellow hybrid cultivars were studied. The flower colors were measured by CIE L~*a~*b~* scale,and flavonoids were qualitatively and quantitatively analyzed by ultra-performance liquid chromatography quadrupole-time-of-flight mass spectrometry. The relationship between flower colors and flavonoid components was explored by analyzed by multiple liner regression analyses. Ten flavonoids were detected in C. nitidissima,white C. japonica and their three hybrid cultivars. The flavonoids including pelargonium-3-O-glucoside(Pg3G),luteolin-7-O-rutinoside(Lu7 R),eriodictyol(Er)and genistin(Gin)were identified in C. nitidissima for the first time. Pg3G,Er and Gin were not determined in white C. japonica‘Yinbai Chalis' and‘Baifeng',and the contents of Lu7 R were extremely low. The main components of C. nitidissima were quercetin-3-O-glucoside( Qu3G),quercetin-3-O-rutinoside(Qu3R),quercetin-7-O-glucoside(Qu7 G),kaempferol-3-O-glucoside(Km3G),Pg3G and Lu7 R. The contents of luteolin(Lu),kaempferol(Km)and Er in hybrid cultivars surpassed their parents,and those of the rest and total flavonoids were between their parents. Qu3G and Qu3R were the important components which decided the yellow color of C. nitidissima and its hybrid cultivars,and the increase of their contents caused the flower color to remarkably turn yellow. The accumulation of Qu3G significantly enhanced the brilliance of flower color,and Pg3G affected the color tone.
引文
Byamukama R,Jordheim M,Kiremire B,Namukobe J,Andersen Y M.2006.Anthocyanins from flowers of Hippeastrum cultivars.Scientia Horticulturae,109(3):262-266.
Gao Ji-yin,Su Yu-hua,Hu Xian-cong.2007.The identification and appreciation of the world’s outstanding Camellias.Hangzhou:Zhejiang Science and Technology Publishing House:8-9.(in Chinese)高继银,苏玉华,胡羡聪.2007.国内外茶花名种识别与欣赏.杭州:浙江科学技术出版社:8-9.
Guan Kai-yun,Li Ji-yuan,Wang Zhong-lang.2014.Camellias of China.Hangzhou:Zhejiang Science and Technology Publishing House:395-406.(in Chinese)管开云,李纪元,王仲朗.2014.中国茶花图鉴.杭州:浙江科学技术出版社:395-406.
Hashimoto F,Tanaka M,Maeda H,Tanaka M,Shimizu K.2002.Changes in flower coloration and sepal anthocyanins of cyanic Delphinium cultivars during flowering.Bioscience Biotechnology and Biochemistry,66(8):1652-1659.
He D Y,Li X Y,Xuan S,Wang L L,Li S Y,Xu Y P.2017.Camellia nitidissima,C.W.Chi:a review of botany,chemistry and pharmacology.Phytochemistry Reviews,10:1-23.
He D Y,Wang X T,Zhang P,Luo X X,Li X Y,Wang L L,Li S Y,Xu Y P.2015.Evaluation of the anxiolytic and antidepressant activities of the aqueous extract from Camellia euphlebia Merr.ex Sealy in mice.Evidence-Based Complementray and Alternative Medicine,11:1-8.
Hwang Y J,Yoshikawa K,Miyajima I,Okubo H.1992.Flower colors and pigments in hybrids with Camellia chrysantha.Scientia Horticulturae,51(s 3-4):251-259.
Li Bei-jia,Xiang Cheng,Yang Xiu-wei,Wu Li-jun,Guo De-an,Ye Min.2010.Fingerprints of tongmai keli by HPLC-DAD-MS.Acta Pharmaceutica Sinica,45(11):1410-1414.(in Chinese)李蓓佳,向诚,杨秀伟,吴立军,果德安,叶敏.2010.应用高效液相色谱-质谱联用技术研究通脉颗粒的指纹图谱.药学学报,45(11):1410-1414.
Li J B,Hashimoto F,Shimizu K,Sakata Y.2007.Anthocyanins from red flowers of Camellia reticulata L.Bioscience Biotechnology and Biochemistry,71(11):2833-2836.
Li J B,Hashimoto F,Shimizu K,Sakata Y.2008.Anthocyanins from red flowers of Camellia cultivar‘Dalicha’.Phytochemistry,69(18):3166-3171.
Li J B,Hashimoto F,Shimizu K,Sakata Y.2009.A new acylated anthocyan inform the red flowers of Camellia hongkongensis and characterization of anthocyanins in the Section Camellia species.Journal of Plant Ecology,51(6):545-552.
Liang Sheng-ye.1993.Camellia nitidissima.Beijing:China Forestry Publishing House:1-100.(in Chinese)梁盛业.1993.金花茶.北京:中国林业出版社:1-100.
Lin J N,Lin H Y,Yang N S,Li Y H,Lee M R,Chuang C H,Ho C T,Kuo S C,Way T D.2013.Chemical constituents and anticancer activity of yellow Camellias against MDA-MB-231 human breast cancer cells.Journal of Agricultural&Food Chemistry,61(40):9638-9644.
Mikanagi Y,Saito N,Yokoi M,Tatsuzawa F.2000.Anthocyanins in flowers of genus Rosa,sections Cinnamomeae(Rosa),Chinenses,Gallicanae and some modern garden roses.Biochemical Systematics and Ecology,28:887-902.
Miyashima K.1997.Study on flower color and anthocyanidin of Camellia chrysantha and F1 generation.Guangxi Forestry Science,26(1):52-53.(in Chinese)宫岛郁夫.1997.金花茶(Camellia chrysantha)及F1代的花色及花色素研究.广西林业科学,26(1):52-53.
Peng X,Yu D Y,Feng B M,Wang Y Q,Shi L Y.2012.A new acylated flavonoid glycoside from the flowers of Camellia nitidissima and its effect on the induction of apoptosis in human lymphoma U937 cells.Journal of Asian Natural Products Research,14(8):799-804.
Peng Xiao,Yu Da-yong,Feng Bao-min,Tang Ling,Wang Yong-qi,Shi Li-ying.2011.Chemical constituents from the flowers of Camellia chrysantha.Guihaia,31(4):550-553.(in Chinese)彭晓,于大永,冯宝民,唐玲,王永奇,史丽颖.2011.金花茶花化学成分的研究.广西植物,31(4):550-553.
Qi J,Shi R F,Yu J M,Li Y,Yuan S T,Yang J Z,Hu J M,Jia A Q.2016.Chemical constituents from leaves of Camellia nitidissima and their potential cytotoxicity on SGC7901 cells.Chinese Herbal Medicines,8(1):80-84.
Sangwan N S,Shanker S,Sangwan R S,Kumar S.2015.Plant-derived products as antimutagens.Phytotherapy Research,12(6):389-399.
Song L X,Wang X S,Zheng X Q,Huang D J.2011.Polyphenolic antioxidant profiles of yellow Camellia.Food Chemistry,129:351-357.
Tanaka Y,Tsuda S,Kusumi T.1998.Metabolic engineering to modify flower color.Plant Cell Physiology,39(11):1119-1126.
Tomás-Barberán F A,Harborne J B,Self R.1987.Dimalonated anthocyanins from the flowers of Salvia splendens and S.coccinea.Phytochemistry,26:2759-2760.
Uddin A F M J,Hashimoto F,Miwa T,Ohbo K,Sakata Y.2004.Seasonal variation in pigmentation and anthocyanidin phenetics in commercial Eustoma flowers.Scientia Horticulturae,100(1):103-115.
Wang L S,Hashimoto F,Shiraishi A,Aoki N,Li J J,Sakata Y.2004.Chemical taxonomy in Xibei tree peony from China by floral pigmentation.Journal of Plant Research,117(1):47-55.
Zhang Jie,Wang Liang-sheng,Gao Jin-ming,Li Sheng-bo,Xu Yan-jun,Li Chong-hui,Yang Rui-zhen.2011.Identification of anthocyanins involving in petal coloration in Chaenomeles speciosa cultivars.Acta Horticulturae Sinica,38(3):527-534.(in Chinese)张洁,王亮生,高锦明,李圣波,徐彦军,李崇晖,杨瑞珍.2011.贴梗海棠花青苷组成及其与花色的关系.园艺学报,38(3):527-534.
Zhang Wei-bing,Wang Zhi-cong,Zhang Ling-yi.2013.Determination of 10 caffeoylquinic acids and 22 flavonoids in chrysanthemum samples by ultra-high performance liquid chromatography-diode array detection-tandem Mass Spectrometry.Chinese Journal of Analytical Chemistry,41(12):1851-1861.(in Chinese)张维冰,王智聪,张凌怡.2013.超高效液相色谱-二极管阵列检测-串联质谱法测定菊花中的10种咖啡酰基奎宁酸和22种黄酮类化合物.分析化学,41(12):1851-1861.
Zhou X W,Fan Z Q,Chen Y,Zhu Y L,Li J Y,Yin H F.2013.Functional analyses of a flavonol synthase-like gene from Camellia nitidissima reveal its roles in flavonoid metabolism during floral pigmentation.Journal of Biosciences,38(3):593-604.
Gao Ji-yin,Su Yu-hua,Hu Xian-cong.2007.The identification and appreciation of the world’s outstanding Camellias.Hangzhou:Zhejiang Science and Technology Publishing House:8-9.(in Chinese)高继银,苏玉华,胡羡聪.2007.国内外茶花名种识别与欣赏.杭州:浙江科学技术出版社:8-9.
Guan Kai-yun,Li Ji-yuan,Wang Zhong-lang.2014.Camellias of China.Hangzhou:Zhejiang Science and Technology Publishing House:395-406.(in Chinese)管开云,李纪元,王仲朗.2014.中国茶花图鉴.杭州:浙江科学技术出版社:395-406.
Hashimoto F,Tanaka M,Maeda H,Tanaka M,Shimizu K.2002.Changes in flower coloration and sepal anthocyanins of cyanic Delphinium cultivars during flowering.Bioscience Biotechnology and Biochemistry,66(8):1652-1659.
He D Y,Li X Y,Xuan S,Wang L L,Li S Y,Xu Y P.2017.Camellia nitidissima,C.W.Chi:a review of botany,chemistry and pharmacology.Phytochemistry Reviews,10:1-23.
He D Y,Wang X T,Zhang P,Luo X X,Li X Y,Wang L L,Li S Y,Xu Y P.2015.Evaluation of the anxiolytic and antidepressant activities of the aqueous extract from Camellia euphlebia Merr.ex Sealy in mice.Evidence-Based Complementray and Alternative Medicine,11:1-8.
Hwang Y J,Yoshikawa K,Miyajima I,Okubo H.1992.Flower colors and pigments in hybrids with Camellia chrysantha.Scientia Horticulturae,51(s 3-4):251-259.
Li Bei-jia,Xiang Cheng,Yang Xiu-wei,Wu Li-jun,Guo De-an,Ye Min.2010.Fingerprints of tongmai keli by HPLC-DAD-MS.Acta Pharmaceutica Sinica,45(11):1410-1414.(in Chinese)李蓓佳,向诚,杨秀伟,吴立军,果德安,叶敏.2010.应用高效液相色谱-质谱联用技术研究通脉颗粒的指纹图谱.药学学报,45(11):1410-1414.
Li J B,Hashimoto F,Shimizu K,Sakata Y.2007.Anthocyanins from red flowers of Camellia reticulata L.Bioscience Biotechnology and Biochemistry,71(11):2833-2836.
Li J B,Hashimoto F,Shimizu K,Sakata Y.2008.Anthocyanins from red flowers of Camellia cultivar‘Dalicha’.Phytochemistry,69(18):3166-3171.
Li J B,Hashimoto F,Shimizu K,Sakata Y.2009.A new acylated anthocyan inform the red flowers of Camellia hongkongensis and characterization of anthocyanins in the Section Camellia species.Journal of Plant Ecology,51(6):545-552.
Liang Sheng-ye.1993.Camellia nitidissima.Beijing:China Forestry Publishing House:1-100.(in Chinese)梁盛业.1993.金花茶.北京:中国林业出版社:1-100.
Lin J N,Lin H Y,Yang N S,Li Y H,Lee M R,Chuang C H,Ho C T,Kuo S C,Way T D.2013.Chemical constituents and anticancer activity of yellow Camellias against MDA-MB-231 human breast cancer cells.Journal of Agricultural&Food Chemistry,61(40):9638-9644.
Mikanagi Y,Saito N,Yokoi M,Tatsuzawa F.2000.Anthocyanins in flowers of genus Rosa,sections Cinnamomeae(Rosa),Chinenses,Gallicanae and some modern garden roses.Biochemical Systematics and Ecology,28:887-902.
Miyashima K.1997.Study on flower color and anthocyanidin of Camellia chrysantha and F1 generation.Guangxi Forestry Science,26(1):52-53.(in Chinese)宫岛郁夫.1997.金花茶(Camellia chrysantha)及F1代的花色及花色素研究.广西林业科学,26(1):52-53.
Peng X,Yu D Y,Feng B M,Wang Y Q,Shi L Y.2012.A new acylated flavonoid glycoside from the flowers of Camellia nitidissima and its effect on the induction of apoptosis in human lymphoma U937 cells.Journal of Asian Natural Products Research,14(8):799-804.
Peng Xiao,Yu Da-yong,Feng Bao-min,Tang Ling,Wang Yong-qi,Shi Li-ying.2011.Chemical constituents from the flowers of Camellia chrysantha.Guihaia,31(4):550-553.(in Chinese)彭晓,于大永,冯宝民,唐玲,王永奇,史丽颖.2011.金花茶花化学成分的研究.广西植物,31(4):550-553.
Qi J,Shi R F,Yu J M,Li Y,Yuan S T,Yang J Z,Hu J M,Jia A Q.2016.Chemical constituents from leaves of Camellia nitidissima and their potential cytotoxicity on SGC7901 cells.Chinese Herbal Medicines,8(1):80-84.
Sangwan N S,Shanker S,Sangwan R S,Kumar S.2015.Plant-derived products as antimutagens.Phytotherapy Research,12(6):389-399.
Song L X,Wang X S,Zheng X Q,Huang D J.2011.Polyphenolic antioxidant profiles of yellow Camellia.Food Chemistry,129:351-357.
Tanaka Y,Tsuda S,Kusumi T.1998.Metabolic engineering to modify flower color.Plant Cell Physiology,39(11):1119-1126.
Tomás-Barberán F A,Harborne J B,Self R.1987.Dimalonated anthocyanins from the flowers of Salvia splendens and S.coccinea.Phytochemistry,26:2759-2760.
Uddin A F M J,Hashimoto F,Miwa T,Ohbo K,Sakata Y.2004.Seasonal variation in pigmentation and anthocyanidin phenetics in commercial Eustoma flowers.Scientia Horticulturae,100(1):103-115.
Wang L S,Hashimoto F,Shiraishi A,Aoki N,Li J J,Sakata Y.2004.Chemical taxonomy in Xibei tree peony from China by floral pigmentation.Journal of Plant Research,117(1):47-55.
Zhang Jie,Wang Liang-sheng,Gao Jin-ming,Li Sheng-bo,Xu Yan-jun,Li Chong-hui,Yang Rui-zhen.2011.Identification of anthocyanins involving in petal coloration in Chaenomeles speciosa cultivars.Acta Horticulturae Sinica,38(3):527-534.(in Chinese)张洁,王亮生,高锦明,李圣波,徐彦军,李崇晖,杨瑞珍.2011.贴梗海棠花青苷组成及其与花色的关系.园艺学报,38(3):527-534.
Zhang Wei-bing,Wang Zhi-cong,Zhang Ling-yi.2013.Determination of 10 caffeoylquinic acids and 22 flavonoids in chrysanthemum samples by ultra-high performance liquid chromatography-diode array detection-tandem Mass Spectrometry.Chinese Journal of Analytical Chemistry,41(12):1851-1861.(in Chinese)张维冰,王智聪,张凌怡.2013.超高效液相色谱-二极管阵列检测-串联质谱法测定菊花中的10种咖啡酰基奎宁酸和22种黄酮类化合物.分析化学,41(12):1851-1861.
Zhou X W,Fan Z Q,Chen Y,Zhu Y L,Li J Y,Yin H F.2013.Functional analyses of a flavonol synthase-like gene from Camellia nitidissima reveal its roles in flavonoid metabolism during floral pigmentation.Journal of Biosciences,38(3):593-604.