西红花去柱头花部黄酮类成分分析Analysis of flavonoids from saffron floral bio-residues
向俊洁;陈娜;李化;张雪;杨滨;黄璐琦;
XIANG Jun-jie;CHEN Na;LI Hua;ZHANG Xue;YANG Bin;HUANG Lu-qi;Academician Workstation of Jiangxi University of Traditional Chinese Medicine;Institute of Chinese Materia Medica,China Academy of Chinese Medical Sciences;Shanghai Traditional Chinese Medicine Co.,Ltd.;China Academy of Chinese Medical Sciences;
摘要(Abstract):
为开发利用西红花去柱头花部,采用色谱及质谱技术对其黄酮类成分进行了定性定量分析。采用UPLC-Q-TOF-MS技术对西红花去柱头花部进行了化学成分的定性分析,推测了50个黄酮醇类化合物和5个花色苷类化合物;采用UPLC技术建立了西红花去柱头花部的指纹图谱及其主要黄酮类成分山柰酚-3-O-槐糖苷、飞燕草素-3,5-二-O-葡萄糖苷的含量测定方法,并对10批不同产地样品进行了测定分析,10批样品指纹图谱相似度均在0.99以上,山柰酚-3-O-槐糖苷质量分数为44.21~58.73 mg·g~(-1),飞燕草素-3,5-二-O-葡萄糖苷质量分数为2.11~6.37 mg·g~(-1);采用电子眼技术将样品的颜色数字化,发现样品颜色与飞燕草素-3,5-二-O-葡萄糖苷的含量显著相关。研究结果显示,西红花去柱头花部富含黄酮类成分,有开发利用的潜力;不同产地样品中花色苷类成分含量的差异较大,应注意样品前处理及贮藏的方法。
In order to better utilize saffron floral bio-residues(SFB), a qualitative and quantitative analysis of flavonoids in SFB was conducted using UPLC-MS and UPLC, respectively. On the one hand, 50 flavonols and 5 anthocyanins were putatively characte-rized by using UPLC-Q-TOF-MS. On the other hand, an UPLC method was established for determining the fingerprint of SFB as well as testing the main flavonoids kaempferol-3-O-sophoroside and delphinidin-3,5-di-O-glucoside. Contents of kaempferol-3-O-sophoroside and delphinidin-3,5-di-O-glucoside of 10 batches of samples were 44.21-58.73 mg·g~(-1) and 2.11-6.37 mg·g~(-1), respectively, and the similarities of 10 batches were more than 0.99. In addition, the color of the samples was digitized by using electronic eye technology, and it was found that the color of the samples was significantly correlated with the content of delphinidin-3,5-di-O-glucoside. The richness of flavonoids in SFB indicated its potential for development and utilization, and the large variation in anthocyanin content among samples from different regions suggested that more attention should be paid to the methods of sample pretreatment and storage.
关键词(KeyWords):
西红花去柱头花部;黄酮类成分;液质定性分析;指纹图谱;含量测定
saffron floral bio-residues;flavonoids;UPLC-Q-TOF-MS qualitative analysis;fingerprint;content determination
基金项目(Foundation): 国家重点研发计划“中医药现代化研究”专项(2018YFC1706103);; 中央本级重大增减支项目(2060302)
作者(Author):
向俊洁;陈娜;李化;张雪;杨滨;黄璐琦;
XIANG Jun-jie;CHEN Na;LI Hua;ZHANG Xue;YANG Bin;HUANG Lu-qi;Academician Workstation of Jiangxi University of Traditional Chinese Medicine;Institute of Chinese Materia Medica,China Academy of Chinese Medical Sciences;Shanghai Traditional Chinese Medicine Co.,Ltd.;China Academy of Chinese Medical Sciences;
Email:
DOI: 10.19540/j.cnki.cjcmm.20201214.302
参考文献(References):
- [1] 国家药典委员会.中华人民共和国药典.一部[S].北京:中国医药科技出版社,2015.
- [2] EBRAHIM-HABIBI M B,AMININASAB M,EBRAHIM-HABIBI A,et al.Fibrillation of alpha-lactalbumin:effect of crocin and safranal,two natural small molecules from Crocus sativus [J].Biopolymers,2010,93(10):854.
- [3] 刘江弟,欧阳臻,杨滨.西红花品质评价研究进展[J].中国中药杂志,2017,42(3):405.
- [4] SERRANO-DíAZ J,SáNCHEZ A M,MARTíNEZ-TOMé M,et al.Flavonoid determination in the quality control of floral bioresidues from Crocus sativus L.[J].J Agric Food Chem,2014,62(14):3125.
- [5] 陈娜,杨滨.西红花非药用部位化学成分和药理作用研究进展[J].中国中药杂志,2018,43(14):2884.
- [6] HOSSEINI A,RAZAVI B M,HOSSEINZADEH H.Saffron (Crocus sativus) petal as a new pharmacological target:a review [J].Iran J Basic Med Sci,2018,21(11):1091.
- [7] ABLAJAN K,ABLIZ Z,SHANG X Y,et al.Structural characterization of flavonol-3,7-di-O-glycosides and determination of the glycosylation position by using negative ion electrospray ionization tandem mass spectrometry [J].J Mass Spectrom,2006,41(3):352.
- [8] 马婷婷,龚慕辛,王智民,等.甘草色泽与有效成分含量的相关性研究[J].中国中药杂志,2017,42(19):3776.
- [9] KIM T H,KU S K,LEE I C,et al.Anti-inflammatory effects of kaempferol-3-O-sophoroside in human endothelial cells [J].Inflamm Res,2012,61(3):217.
- [10] KIM T H,KU S K,BAE J S.Inhibitory effects of kaempferol-3-O-sophoroside on HMGB1-mediated proinflammatory responses [J].Food Chem Toxicol,2012,50(3/4):1118.
- [11] SUN C T,NILE S H,ZHANG Y T,et al.Novel insight into utilization of flavonoid glycosides and biological properties of saffron (Crocus sativus L.) flower by-products [J].J Agric Food Chem,2020,doi:10.1021/acs.jafc.0c04076.
- [12] YANG Y,TIAN Y P,ZHANG Q H,et al.Comparative effects of flavonoids from Fructus Sophorae on rat osteoblasts in vitro [J].Rec Nat Prod,2019,14(1):65.
- [13] MARY S J,MERINA A J.Antibacterial activity of kaempferol-3-O-glucoside [J].Int J Sci Res,2012,3(5):46.
- [14] WANG Y,TANG C Y,ZHANG H.Hepatoprotective effects of kaempferol-3-O-rutinoside and kaempferol-3-O-glucoside from Carthamus tinctorius L.on CCl4-induced oxidative liver injury in mice [J].J Food Drug Anal,2015,23(2):310.
- [15] HE J W,HUANG X Y,WANG Y Q,et al.A new flavonol glycoside from the flowers of Hosta plantaginea with cyclooxygena-ses-1/2 inhibitory and antioxidant activities [J].Nat Prod Lett,2019,33(11):1599.
- [16] WANG R H,LIU Q,WU Z L,et al.Target-guided isolation of polar antioxidants from Abelmoschus esculentus (L).Moench by high-speed counter-current chromatography method coupled with wavelength switching and extrusion elution mode [J].J Sep Sci,2016,39(20):3983.
- [17] LEE Y S,LEE S,LEE H S,et al.Inhibitory effects of isorhamnetin-3-O-beta-D-glucoside from Salicornia herbacea on rat lens aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues [J].Biol Pharm Bull,2005,28(5):916.
- [18] VIEGAS O,FARIA M A,SOUSA J B,et al.Delphinidin-3-O-glucoside inhibits angiogenesis via VEGFR2 downregulation and migration through actin disruption [J].J Funct Foods,2019,54:393.
- [19] GIUSTI M M,WROLSTAD R E.Acylated anthocyanins from edi-ble sources and their applications in food systems [J].Biochem Eng J,2003,14(3):217.
- [20] PATRAS A,BRUNTON N P,O′DONNELL C,et al.Effect of thermal processing on anthocyanin stability in foods;mechanisms and kinetics of degradation [J].Trends Food Sci Technol,2010,21(1):3.
- [21] ESCHER G B,WEN M,ZHANG L,et al.Phenolic composition by UHPLC-Q-TOF-MS/MS and stability of anthocyanins from Clitoria ternatea L.(butterfly pea) blue petals [J].Food Chem,2020,331:127341.
- [22] MIGLIORINI A A,PIROSKI C S,DANIEL T G,et al.Red Chicory (Cichorium intybus) extract rich in anthocyanins:che-mical stability,antioxidant activity,and antiproliferative activity in vitro [J].J Food Sci,2019,84(5):990.
- [23] SAGDIC O,EKICI L,OZTURK I,et al.Cytotoxic and bioactive properties of different color tulip flowers and degradation kinetic of tulip flower anthocyanins [J].Food Chem Toxicol,2013,58:432.
- [24] TAVERNITI V,FRACASSETTI D,DEL B C,et al.Immunomodulatory effect of a wild blueberry anthocyanin-rich extract in human Caco-2 intestinal cells [J].J Agric Food Chem,2014,62(33):8346.
- [25] LIN B W,GONG C C,SONG H F,et al.Effects of anthocyanins on the prevention and treatment of cancer [J].Br J Pharmacol,2017,174(11):1226.
- [26] ZIBERNA L,TRAMER F,MOZE S,et al.Transport and bioactivity of cyanidin 3-glucoside into the vascular endothelium [J].Free Radical Biol Med,2012,52(9):1750.
- [27] ESCHER G B,MARQUES M B,DO CARMO M A V,et al.Clitoria ternatea L.petal bioactive compounds display antioxidant,antihemolytic and antihypertensive effects,inhibit α-amy-lase and α-glucosidase activities and reduce human LDL choles-terol and DNA induced oxidation [J].Food Res Int,2020,128:108763.
- 西红花去柱头花部
- 黄酮类成分
- 液质定性分析
- 指纹图谱
- 含量测定
saffron floral bio-residues - flavonoids
- UPLC-Q-TOF-MS qualitative analysis
- fingerprint
- content determination
- 向俊洁
- 陈娜
- 李化
- 张雪
- 杨滨
- 黄璐琦
XIANG Jun-jie- CHEN Na
- LI Hua
- ZHANG Xue
- YANG Bin
- HUANG Lu-qi
- Academician Workstation of Jiangxi University of Traditional Chinese Medicine
- Institute of Chinese Materia Medica
- China Academy of Chinese Medical Sciences
- Shanghai Traditional Chinese Medicine Co.
- Ltd.
- China Academy of Chinese Medical Sciences
- 向俊洁
- 陈娜
- 李化
- 张雪
- 杨滨
- 黄璐琦
XIANG Jun-jie- CHEN Na
- LI Hua
- ZHANG Xue
- YANG Bin
- HUANG Lu-qi
- Academician Workstation of Jiangxi University of Traditional Chinese Medicine
- Institute of Chinese Materia Medica
- China Academy of Chinese Medical Sciences
- Shanghai Traditional Chinese Medicine Co.
- Ltd.
- China Academy of Chinese Medical Sciences