HUO Huazhen, CAI Aihua, XIE Yunchang. Determination of Content of 6 Triterpenic Acids in Malus doumeri Fruit by High-performance Liquid Chromatography[J]. Science and Technology of Food Industry, 2024, 45(13): 272−280. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2023090167.
Citation: HUO Huazhen, CAI Aihua, XIE Yunchang. Determination of Content of 6 Triterpenic Acids in Malus doumeri Fruit by High-performance Liquid Chromatography[J]. Science and Technology of Food Industry, 2024, 45(13): 272−280. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2023090167.

Determination of Content of 6 Triterpenic Acids in Malusdoumeri Fruit by High-performance Liquid Chromatography

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  • Received Date: September 17, 2023
  • Available Online: May 04, 2024
  • A HPLC method was developed for the simultaneous determination of euscaphic acid, 2α,19α-dihydroxy-3-oxo-urs-12-en-28-oic acid, maslinic acid, corosolic acid, oleanic acid, and ursolic acid in Malus doumeri fruits. Analyses were conducted on the distribution and content of these six triterpenic acids in Malus doumeri fruits from six producing areas in Guangxi. Using gradient elution at a flow rate of 0.8 mL/min, a Diamonsil C18 (2) column was used with a mobile phase of 0.1% formic acid aqueous solution/methanol (v/v). The detection wavelength was 210 nm and the column temperature was 30 ℃. The results showed that the mass concentrations of the six triterpenic acids had a good linear relationship with the chromatographic peak areas in the linear range. The correlation coefficients were greater than 0.9990, the detection limits were within 0.46~2.00 μg/mL, the lower quantitation limits were within 1.53~6.67 μg/mL, the coefficients of variation were less than 5.0%, and the recovery percentages were within 99.2%~101.3%. Six samples from different production areas contained six triterpenic acids (euscaphic acid, 2α,19α-dihydroxy-3-oxo-urs-12-en-28-oic acid, maslinic acid, corosolic acid, oleanic acid, and ursolic acid). Each of the six triterpenic acids was a pentacyclic triterpenic acid. Among the six triterpenic acids, euscaphic acid and 2α,19α-dihydroxy-3-oxo-urs-12-en-28-oic acid were first detected in Malus doumeri fruits. Ursolic acid, euscaphic acid, and 2α,19α-dihydroxy-3-oxo-urs-12-en-28-oic acid were predominant, accounting for 71.82%~81.38% of the total triterpenic acids. The total triterpenic acids content ranged from 808.74 to 1090.75 μg/g FM. The total triterpenic acids content of fruits from Liujiang district of Liuzhou and Pingle of Guilin were relatively high, reaching 1090.75 μg/g FM and 1045.20 μg/g FM, respectively. Overall, this study's HPLC method can detect the triterpenic acids content of Malus doumeri fruits and provide scientific references for the quality evaluation of Malus doumeri fruit's raw materials and products.
  • [1]
    曾勇豪, 唐初明, 周云涛. 广西风味小野果涩梨的特点及开发利用价值研究[J]. 林业勘查设计,2014(2):85−88. [ZENG Y H, TANG C M, ZHOU Y T. Study of characteristics and utilization value of Malus doumeri in Guangxi[J]. Forest Investigation Design,2014(2):85−88.]

    ZENG Y H, TANG C M, ZHOU Y T. Study of characteristics and utilization value of Malus doumeri in Guangxi[J]. Forest Investigation Design, 2014(2): 85−88.
    [2]
    王雷宏, 杨俊仙, 郑玉红, 等. 台湾林檎(Malus doumeri (Bois.) Chev.)地理分布模拟[J]. 东北林业大学学报,2012,40(9):15−18. [WANG L H, YANG J S, ZHENG Y H, et al. Modeling of geographic distribution of Malus doumeri[J]. Journal of Northeast Forestry University,2012,40(9):15−18.] doi: 10.3969/j.issn.1000-5382.2012.09.004

    WANG L H, YANG J S, ZHENG Y H, et al. Modeling of geographic distribution of Malus doumeri[J]. Journal of Northeast Forestry University, 2012, 40(9): 15−18. doi: 10.3969/j.issn.1000-5382.2012.09.004
    [3]
    黄欣欣. 大果山楂黄酮类物质的提取及其抗氧化性和降血脂功能研究[D]. 南宁:广西大学, 2015. [HANG X X. Study on the anti-oxidant activity and hypolipidemic effect of Malus doumeri (Bois.) Chev. flavonoids extraction[D]. Nanning:Guangxi University, 2015.]

    HANG X X. Study on the anti-oxidant activity and hypolipidemic effect of Malus doumeri (Bois.) Chev. flavonoids extraction[D]. Nanning: Guangxi University, 2015.
    [4]
    温玲蓉. 北山楂和大果山楂的活性成分及其抗氧化与抗增殖活性研究[D]. 广州:华南理工大学, 2016. [WEN L R. Study on the bioactive chemical constituents and their antioxidantive and anti-proliferative activities of Crataegus pinnatifida and Malus doumeri fruits[D]. Guangzhou:South China University of Technology, 2016.]

    WEN L R. Study on the bioactive chemical constituents and their antioxidantive and anti-proliferative activities of Crataegus pinnatifida and Malus doumeri fruits[D]. Guangzhou: South China University of Technology, 2016.
    [5]
    赵帅, 郝二伟, 杜正彩, 等. 广山楂的化学成分、药理作用与质量控制研究进展[J]. 中成药,2020,42(1):169−175. [ZHAO S, HAO E W, DU Z C, et al. Advance in studies on chemical constituents, pharmacology and quality control of Malus doumeri[J]. Chinese Traditional Patent Medicine,2020,42(1):169−175.] doi: 10.3969/j.issn.1001-1528.2020.01.035

    ZHAO S, HAO E W, DU Z C, et al. Advance in studies on chemical constituents, pharmacology and quality control of Malus doumeri[J]. Chinese Traditional Patent Medicine, 2020, 42(1): 169−175. doi: 10.3969/j.issn.1001-1528.2020.01.035
    [6]
    ZHU K, HUANG G B, JING X, et al. Preventive effect of flavonoids from Wushan Shencha (Malus doumeri leaves) on CCl4-induced liver injury[J]. Food Science Nutrition,2019,7(11):3808−3818. doi: 10.1002/fsn3.1243
    [7]
    黄翠丽, 李军集, 蓝金宣, 等. 靖西大果山楂叶、鲜果及酒中有效成分分析[J]. 广西林业科学,2021,50(1):66−70. [HUANG C L, LI J J, LAN J X, et al. Analysis on effective components of Crataegus jingxienis leaves, fresh fruit and wine[J]. Guangxi Forestry Science,2021,50(1):66−70.]

    HUANG C L, LI J J, LAN J X, et al. Analysis on effective components of Crataegus jingxienis leaves, fresh fruit and wine[J]. Guangxi Forestry Science, 2021, 50(1): 66−70.
    [8]
    邓家刚, 韦松基. 广西道地药材[M]. 北京:中国中医药出版社, 2007:24−31. [DENG J G, WEI S J. Authentic medicines of Guangxi[M]. Beijing:China Traditional Chinese Medicine Press, 2007:24−31.]

    DENG J G, WEI S J. Authentic medicines of Guangxi[M]. Beijing: China Traditional Chinese Medicine Press, 2007: 24−31.
    [9]
    广西壮族自治区食品药品监督管理局. 广西壮族自治区壮药质量标准(第二卷)[M]. 南宁:广西科学技术出版社, 2011:26−27. [Food and Drug Administration of Guangxi Autonomous Region. Quality standard of Zhuang medicine of Guangxi Autonomous Region Volume 2(2011 Edition)[M]. Nanning:Guangxi Science & Technology Press, 2011:26−27.]

    Food and Drug Administration of Guangxi Autonomous Region. Quality standard of Zhuang medicine of Guangxi Autonomous Region Volume 2(2011 Edition)[M]. Nanning: Guangxi Science & Technology Press, 2011: 26−27.
    [10]
    郭婷, 白向丽, 陈益能, 等. 干燥方式对大果山楂粉干燥速率及品质的影响[J]. 食品与机械,2019,35(10):122−125,188. [GUO T, BAI X L, CHEN Y N, et al. Effect of drying treatment methods on the drying rate and quality characteristics of big fruit hawthorn[J]. Food & Machinery,2019,35(10):122−125,188.]

    GUO T, BAI X L, CHEN Y N, et al. Effect of drying treatment methods on the drying rate and quality characteristics of big fruit hawthorn[J]. Food & Machinery, 2019, 35(10): 122−125,188.
    [11]
    张巧, 陈春喜, 陈振林, 等. 大果山楂酵素发酵过程中组分及抗氧化性研究[J]. 食品研究与开发,2018,39(22):15−19. [ZHANG Q, CHEN C X, CHEN Z L, et al. Research of compositions and antioxidant activity during natural fermentation of Malus domeri (Bois) Chev. enzyme drink[J]. Food Research and Development,2018,39(22):15−19.] doi: 10.3969/j.issn.1005-6521.2018.22.003

    ZHANG Q, CHEN C X, CHEN Z L, et al. Research of compositions and antioxidant activity during natural fermentation of Malus domeri (Bois) Chev. enzyme drink[J]. Food Research and Development, 2018, 39(22): 15−19. doi: 10.3969/j.issn.1005-6521.2018.22.003
    [12]
    WEN L R, ZHENG G Q, YOU L J, et al. Phytochemical profiles and cellular antioxidant activity of Malus doumeri (bois) chevalier on 2, 2′-azobis (2-amidinopropane) dihydrochloride (ABAP)-induced oxidative stress[J]. Journal of Functional Foods,2016,25:242−256. doi: 10.1016/j.jff.2016.06.004
    [13]
    陈秋虹, 黄岛平, 蒋艳芳. 大果山楂营养成分与功能成分分析及评价[J]. 轻工科技,2016,32(11):3−4. [CHEN Q H, HUANG D P, JIANG Y F. Analysis and evaluation of nutrients and functional components of Malus domeri (Bois) Chev

    J]. Light Industry Science and Technology,2016,32(11):3−4.
    [14]
    黄小兰, 何旭峰, 周浓, 等. HPLC法同时测定地参中3种三萜酸的含量[J]. 食品工业科技,2020,41(11):273−278,286. [HUANG X L, HE X F, ZHOU N, et al. Simultaneous determination of three triterpenic acids in Lycopus lucidus Turcz. var. hirtus Regel by high performance liquid chromatography[J]. Science and Technology of Food Industry,2020,41(11):273−278,286.]

    HUANG X L, HE X F, ZHOU N, et al. Simultaneous determination of three triterpenic acids in Lycopus lucidus Turcz. var. hirtus Regel by high performance liquid chromatography[J]. Science and Technology of Food Industry, 2020, 41(11): 273−278,286.
    [15]
    彭富全, 陈明权, 何风雷, 等. HPLC同时测定黑老虎药材中2种三萜酸的含量[J]. 中国医药导报,2018,15(22):31−34. [PENG F Q, CHEN M Q, HE F L, et al. Simultaneous determination of two triterpenic acids in root of Kadsura coccinea by HPLC[J]. China Medical Herald,2018,15(22):31−34.]

    PENG F Q, CHEN M Q, HE F L, et al. Simultaneous determination of two triterpenic acids in root of Kadsura coccinea by HPLC[J]. China Medical Herald, 2018, 15(22): 31−34.
    [16]
    孙燕, 葛斐林, 薛春苗, 等. 天然产物中五环三萜类化合物检测方法的研究进展[J]. 中国现代中药,2019,21(4):552−558. [SUN Y, GE F L, XUE C M, et al. Advances in determination method of pentacyclic triterpenoids in natural products[J]. Modern Chinese Medicine,2019,21(4):552−558.]

    SUN Y, GE F L, XUE C M, et al. Advances in determination method of pentacyclic triterpenoids in natural products[J]. Modern Chinese Medicine, 2019, 21(4): 552−558.
    [17]
    陈秋虹, 黄岛平, 徐慧. 超高效液相色谱测定法测定大果山楂中山楂酸[J]. 轻工科技,2016,32(12):6−7. [CHEN Q H, HUANG D P, XU H. Determination of maslinic acid in Malus domeri (Bois) Chev. by ultra performance liquid chromatography[J]. Light Industry Science and Technology,2016,32(12):6−7.]

    CHEN Q H, HUANG D P, XU H. Determination of maslinic acid in Malus domeri (Bois) Chev. by ultra performance liquid chromatography[J]. Light Industry Science and Technology, 2016, 32(12): 6−7.
    [18]
    张爽, 任亚梅, 刘春利, 等. 响应面试验优化苹果渣总三萜超声提取工艺[J]. 食品科学,2015,36(16):44−50. [ZHANG S, REN Y M, LIU C L, et al. Optimization of ultrasonic-assisted extraction of ttotal triterpenoids from apple pomace by response surface methodology[J]. Food Science,2015,36(16):44−50.] doi: 10.7506/spkx1002-6630-201516008

    ZHANG S, REN Y M, LIU C L, et al. Optimization of ultrasonic-assisted extraction of ttotal triterpenoids from apple pomace by response surface methodology[J]. Food Science, 2015, 36(16): 44−50. doi: 10.7506/spkx1002-6630-201516008
    [19]
    陈丹丹, 郭雪峰, 赵蕾, 等. HPLC法同时检测刚竹属竹叶中4种黄酮碳苷的含量[J]. 林产化学与工业,2019,39(5):108−114. [CHEN D D, GUO X F, ZHAO L, et al. Stimultaneous determination of four flavone C-glycosides in bamboo leaves of Phyllostachys by HPLC[J]. Chemistry and Industry of Forest Products,2019,39(5):108−114.] doi: 10.3969/j.issn.0253-2417.2019.05.015

    CHEN D D, GUO X F, ZHAO L, et al. Stimultaneous determination of four flavone C-glycosides in bamboo leaves of Phyllostachys by HPLC[J]. Chemistry and Industry of Forest Products, 2019, 39(5): 108−114. doi: 10.3969/j.issn.0253-2417.2019.05.015
    [20]
    刘康其, 马聿济, 华国瑛. 高纯甲醇用作反相高效液相色谱移动相[J]. 化学世界,1984(12):15−17. [LIU K Q, MA J Q, HUA G Y. High purity methanol as a mobile phase in reversed phase high performance liquid chromatography[J]. Chemical World,1984(12):15−17.]

    LIU K Q, MA J Q, HUA G Y. High purity methanol as a mobile phase in reversed phase high performance liquid chromatography[J]. Chemical World, 1984(12): 15−17.
    [21]
    孙博, 霍华珍, 蔡爱华, 等. HPLC法测定大果山楂果实中八种酚酸类成分的含量[J]. 广西植物,2021,41(7):1135−1144. [SUN B, HUO H Z, CAI A H, et al. Determination of content of 8 phenolic acids in Malus doumeri fruit by HPLC[J]. Guihaia,2021,41(7):1135−1144.] doi: 10.11931/guihaia.gxzw202003034

    SUN B, HUO H Z, CAI A H, et al. Determination of content of 8 phenolic acids in Malus doumeri fruit by HPLC[J]. Guihaia, 2021, 41(7): 1135−1144. doi: 10.11931/guihaia.gxzw202003034
    [22]
    杨鹏飞, 李保明, 王振中, 等. HPLC法同时测定桂枝茯苓胶囊中4种茯苓三萜酸成分[J]. 中草药,2016,47(18):3215−3218. [YANG P F, LI B M, WANG Z Z, et al. Determination of four triterpenoid acids from Guizhi Fuling capsules by HPLC[J]. Chinese Traditional and Herbal Drugs,2016,47(18):3215−3218.] doi: 10.7501/j.issn.0253-2670.2016.18.013

    YANG P F, LI B M, WANG Z Z, et al. Determination of four triterpenoid acids from Guizhi Fuling capsules by HPLC[J]. Chinese Traditional and Herbal Drugs, 2016, 47(18): 3215−3218. doi: 10.7501/j.issn.0253-2670.2016.18.013
    [23]
    刘宗洋, 赵文文, 武婧悦, 等. HPLC-ELSD测定壮药山绿茶中3对三萜同分异构体含量[J]. 中国中药杂志,2018,43(8):1662−1666. [LIU Z Y, ZHAO W W, WU J Y, et al. Determination of three pair of triterpenoid isomers in leaf of Ilex hainanensis by HPLC-ELSD[J]. China Journal of Chinese Materia Medica,2018,43(8):1662−1666.]

    LIU Z Y, ZHAO W W, WU J Y, et al. Determination of three pair of triterpenoid isomers in leaf of Ilex hainanensis by HPLC-ELSD[J]. China Journal of Chinese Materia Medica, 2018, 43(8): 1662−1666.
    [24]
    罗小凤, 邹盛勤. 南北山楂中5个三萜酸成分的比较研究[J]. 食品科技,2015,40(5):64−67. [LUO X, ZOU S Q. Comparative studies on content of five triterpenic acids in Crataegi cuneatae and Crataegus pinnatifida[J]. Food Science and Technology,2015,40(5):64−67.]

    LUO X, ZOU S Q. Comparative studies on content of five triterpenic acids in Crataegi cuneatae and Crataegus pinnatifida[J]. Food Science and Technology, 2015, 40(5): 64−67.
    [25]
    田春风, 郭宇帆, 商佳琪, 等. 熊果酸的生物活性研究进展[J]. 中国食品卫生杂志,2022,34(6):1361−1365. [TIAN C F, GUO Y F, SHANG J Q, et al. Research progress on biological activity of ursolic acid[J]. Chinese Journal of Food Hygiene,2022,34(6):1361−1365.]

    TIAN C F, GUO Y F, SHANG J Q, et al. Research progress on biological activity of ursolic acid[J]. Chinese Journal of Food Hygiene, 2022, 34(6): 1361−1365.
    [26]
    王向红, 崔同, 齐小菊, 等. HPLC法测定不同品种枣及酸枣中的齐墩果酸和熊果酸[J]. 食品科学,2002(6):137−138. [WANG X H, CUI T, QI X J, et al. Determination of ursolic scid and oleanolic acid in jujuba and wild jujuba by HPLC[J]. Food Science,2002(6):137−138.] doi: 10.3321/j.issn:1002-6630.2002.06.038

    WANG X H, CUI T, QI X J, et al. Determination of ursolic scid and oleanolic acid in jujuba and wild jujuba by HPLC[J]. Food Science, 2002(6): 137−138. doi: 10.3321/j.issn:1002-6630.2002.06.038
    [27]
    BUTKEVIČIŪTĖ A, LIAUDANSKAS M, KVIKLYS D, et al. Qualitative and quantitative composition of triterpenic compounds in the fruit of apple old cultivars grown in Lithuania[J]. Zemdirbyste-Agriculture,2021,108(1):63−70. doi: 10.13080/z-a.2021.108.009
    [28]
    孙莉琼, 郝雯菁, 唐晓清, 等. UPLC-MS/MS研究36个梨品种成熟果实中的特征性多酚和三萜酸类物质[J]. 食品科学,2020,41(22):206−214. [SUN L Q, HAO W J, TANG X Q, et al. Analysis of characteristic polyphenols and triterpenic acids in ripe pears of 36 cultivars by UPLC-MS/MS[J]. Food Science,2020,41(22):206−214.] doi: 10.7506/spkx1002-6630-20200423-301

    SUN L Q, HAO W J, TANG X Q, et al. Analysis of characteristic polyphenols and triterpenic acids in ripe pears of 36 cultivars by UPLC-MS/MS[J]. Food Science, 2020, 41(22): 206−214. doi: 10.7506/spkx1002-6630-20200423-301
    [29]
    JEONG N L, LEE S, CHOI Y A, et al. Inhibitory effects of euscaphic acid in the atopic dermatitis model by reducing skin inflammation and intense pruritus[J]. Inflammation,2022,45(4):1680−1691. doi: 10.1007/s10753-022-01652-x
    [30]
    SHI C F, LI Z C, WU Y Q, et al. Euscaphic acid and tormentic acid protect vascular endothelial cells against hypoxia-induced apoptosis via PI3K/AKT or ERK1/2 signaling pathway[J]. Life Sciences,2020,252(C):117666.
    [31]
    SUN L Q, TAO S T, ZHANG S L. Characterization and quantification of polyphenols and triterpenoids in thinned young fruits of ten pear varieties by UPLC-Q TRAP-MS/MS[J]. Molecules,2019,24(1):159−179. doi: 10.3390/molecules24010159
    [32]
    SHOKO T, YOKO I, ERI K, et al. Production of bioactive triterpenes by Eriobotrya japonica calli[J]. Phytochemistry,2002,59:315−323. doi: 10.1016/S0031-9422(01)00455-1
    [33]
    XU H X, ZENG F Q, WAN M, et al. Anti-HIV triterpene acids from Geum japonicum[J]. Journal of Natural Products,1996,59(7):643−645. doi: 10.1021/np960165e
    [34]
    DOMINGUES R M A, GUERRA A R, DUARTE M, et al. Bioactive triterpenic acids from agroforestry biomass residues to promising therapeutic tools[J]. Mini-Reviews in Organic Chemistry,2014,11:382−399. doi: 10.2174/1570193X113106660001
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