Chemical Constituents of Coix lachryma-jobi and Their Activities on Seed Germination
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    Abstract:

    In order to understand the chemical constituents of bran shell of Coix lachryma-jobi, fifteen compounds were isolated from ethyl acetate fraction of ethanol extract by using various chromatographic methods. Based on their spectroscopic data, their structures were isolated as p-coumaric acid (1), p-coumaric acid methyl ester (2), (E)-2-hydroxyethyl-3-(4-hydroxyphenyl) acrylate (3), caffeic acid methyl ester (4), methyl (E)-3-(4-hydroxy-3-methoxyphenyl) acrylate (5), (E)-3-(4-methoxyphenyl)acrylic acid (6), 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one (7), 2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone (8), p-hydro-xybenzoic acid (9), 3-hydroxy-4-methoxybenzoic acid (10), 1,3,5-trimethoxybenzene (11), methyl (3-hydroxy-2-oxo-2,3-dihydroindol-3-yl)-acetate (12), allantoin (13), 2-(2-hydroxyethyl)-3-methylfumaric acid (14) and 9-octadecenoic acid (15). The compounds 3, 7, 12, 13 and 14 were isolated from coix for the first time. The compounds 1, 2, 9, 10 and 11 had significant inhibitory activity on seed germination.

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    [1] YANG X Y, JIANG L P. Starch grain analysis reveals ancient diet at Kuahuqiao Site, Zhejiang Province[J]. Chin Sci Bull, 2010, 55(12):1150-1156. doi:10.1007/s11434-009-0545-0.
    [2] JIN L M, LIU Y Z, ZHAO X L, et al. Research progress on effective constituents ín coix seed[J]. J Anhui Agric Sci, 2011, 29(10):5734, 5750. doi:10.3969/j.issn.0517-6611.2011.10.024.金黎明, 刘垠孜, 赵晓蕾, 等. 薏苡仁有效成分研究进展[J]. 安徽农业科学, 2011, 29(10):5734,5750. doi:10.3969/j.issn.0517-6611. 2011.10.024.
    [3] LIN Y, LU S H, YU Q R, et al. Study on the antitumor activity of petroleum ether fractions of the extract from stems and leaves of Coix in vitro[J]. Chin J Clin Pharmacol, 2018, 34(3):282-284. doi:10. 13699/j.cnki.1001-6821.2018.03.028.林瑶, 陆世惠, 喻巧容, 等. 薏苡茎叶提取物石油醚部位的体外抗肿瘤活性研究[J]. 中国临床药理学杂志, 2018, 34(3):282-284. doi:10.13699/j.cnki.1001-6821.2018.03.028.
    [4] WANG C, ZHOU L B, ZHANG G B, et al. Drought resistance identification and drought resistance indices screening of job's tears (Coxi lacryma-jobi L.) germplasm resources at seedling stage[J]. Sci Agric Sin, 2017, 50(15):2872-2887. doi:10.3864/j.issn.0578-1752. 2017.15.003.汪灿, 周棱波, 张国兵, 等. 薏苡种质资源苗期抗旱性鉴定及抗旱指标筛选[J]. 中国农业科学, 2017, 50(15):2872-2887. doi:10. 3864/j.issn.0578-1752.2017.15.003.
    [5] SHI M, LI X D, PAN H. Guizhou Industrial Development Status and Research Progress Report of Coix lachryma-jobi in 2018[M]. Beijing:Social Sciences Academic Press, 2018:263-271.石明, 李祥栋, 潘虹. 2018年贵州薏苡产业发展现状及研究进展报告[M]. 北京:社科文献出版社, 2018:263-271.
    [6] DENG S F, YANG Y Q, LIN Z N, et al. Prospect analysis of high value utilization of wastes in Coix lacryma-jobi[C]//Proceedings of the 2016 Annual Conference of Chinese Society of Tropical Crops. Nan-ning:Chinese Society of Tropical Crops, 2016:2.邓素芳, 杨有泉, 林忠宁, 等. 薏苡废弃物高值利用前景解析[C]//中国热带作物学会2016年学术年会论文集. 南宁:中国热带作物学会, 2016:2.
    [7] FORINO M, TARTAGLIONE L, DELL'AVERSANO C, et al. NMR-based identification of the phenolic profile of fruits of Lycium barbarum (goji berries). Isolation and structural determination of a novel N-feruloyl tyramine dimer as the most abundant antioxidant polyphenol of goji berries[J]. Food Chem, 2016, 194:1254-1259. doi:10.1016/j.foodchem.2015.08.129.
    [8] GOPALAKRISHNAN S, SUBBARAO G V, NAKAHARA K, et al. Nitrification inhibitors from the root tissues of Brachiaria humidicola, a tropical grass[J]. J Agric Food Chem, 2007, 55(4):1385-1388. doi:10.1021/jf062593o.
    [9] DELLAGRECA M, PREVITERA L, PURCARO R, et al. Cinnamic ester derivatives from Oxalis pes-caprae (Bermuda Buttercup)[J]. J Nat Prod, 2007, 70(10):1664-1667. doi:10.1021/np0702786.
    [10] LIU W B, DONG L M, LUO B, et al. Chemical constituents from the leaves of Cyclocarya paliurus[J]. J Trop Subtrop Bot, 2018, 26(3):317-322. doi:10.11926/jtsb.3820.刘文斌, 董丽梅, 罗碧, 等. 青钱柳叶的化学成分研究[J]. 热带亚热带植物学报, 2018, 26(3):317-322. doi:10.11926/jtsb.3820.
    [11] WANG L F, CHEN J Y, XIE H H, et al. Phytochemical profiles and antioxidant activity of adlay varieties[J]. J Agric Food Chem, 2013, 61(21):5103-5113. doi:10.1021/jf400556s.
    [12] THANG P T, THOA H T, GIAP T H, et al. Chemical constituents from the ethyl acetate extract of the stems of Macaranga balansae Gagnep[J]. Vietnam J Chem, 2018, 56(2):249-253. doi:10.1002/vjch.201800022.
    [13] OTSUKA H, TAKEUCHI M, INOSHIRI S, et al. Phenolic compounds from Coix lachryma-jobi var. ma-yuen[J]. Phytochemistry, 1989, 28(3):883-886. doi:10.1016/0031-9422(89)80136-0.
    [14] LUO Y, SHEN H Y, ZHANG M, et al. Chemical constituents from the dregs of Brucea javanica[J]. J Trop Subtrop Bot, 2019, 27(3):294-298. doi:10.11926/jtsb.3984.罗应, 申海艳, 张敏, 等. 鸦胆子药渣的化学成分研究[J]. 热带亚热带植物学报, 2019, 27(3):294-298. doi:10.11926/jtsb.3984.
    [15] ZHANG S, SONG L Y, CHEN Y L, et al. Antioxidant chemical composition and determination of total content of phenolic acid in seeds of Actinidia chinensis Planch.[J]. Chin Pharma J, 2019, 54(20):1653-1659. doi:10.11669/cpj.2019.20.004.张珊, 宋乐园, 陈林玉, 等. 中华猕猴桃籽中抗氧化化学成分研究及总酚酸含量测定[J]. 中国药学杂志, 2019, 54(20):1653-1659. doi:10.11669/cpj.2019.20.004.
    [16] GUO Y Z, WEI Q, GAO J, et al. Metabolites of the psychrophilic fungus Pseudogymnoascus pannorum[J]. Nat Prod Res Dev, 2019, 31(3):446-449,505. doi:10.16333/j.1001-6880.2019.3.012.郭永智, 魏茜, 高洁, 等. 嗜低温真菌Pseudogymnoascus pannorum次级代谢产物研究[J]. 天然产物研究与开发, 2019, 31(3):446-449,505. doi:10.16333/j.1001-6880.2019.3.012.
    [17] DING H Y. Extracts and constituents of Rubus chingii with 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity[J]. Int J Mol Sci, 2011, 12(6):3941-3949. doi:10.3390/ijms12063941.
    [18] SANG S M, LAO A N, WANG H C, et al. A phenylpropanoid glycoside from Vaccaria segetalis[J]. Phytochemistry, 1998, 48(3):569-571. doi:10.1016/S0031-9422(97)00896-0.
    [19] SAMY M N, KHALIL H E, SUGIMOTO S, et al. Phytoconstituents from the aerial parts of Lampranthus spectabilis[J]. S Afr J Bot, 2018, 118:179-182. doi:10.1016/j.sajb.2018.07.014.
    [20] SUN X, WU Y Z, ZHANG Y B. Chemical constituents from the twigs and leaves of Croton tiglium[J]. J Chin Med Mat, 2019, 42(8):1796-1800. doi:10.13863/j.issn1001-4454.2019.08.017.孙欣, 吴泳樟, 张玉波. 巴豆枝叶的化学成分研究[J]. 中药材, 2019, 42(8):1796-1800. doi:10.13863/j.issn1001-4454.2019.08.017.
    [21] GAO J X, WU S J, ZHOU Z Y, et al. A study on the explotation and utilization of Coix laclyma-jobi:An experiment on its cultivation and the analysis of its nutrition[J]. J Anhui Agrotechnol Teach Coll, 1994, 8(1):66-68.高金香, 吴世景, 周宗运, 等. 薏苡饲料资源开发和利用的研究——栽培试验及营养分析[J]. 安徽农业技术师范学院学报, 1994, 8(1):66-68.
    [22] DENG S F, YANG Y Q, LI C Y, et al. Feeding value evaluation of coix based on amino acid analysis[J]. Chin J Trop Crops, 2017, 38(8):1468-1477. doi:10.3969/j.issn.1000-2561.2017.08.016.邓素芳, 杨有泉, 李春燕, 等. 基于氨基酸分析的薏苡饲用价值评价[J]. 热带作物学报, 2017, 38(8):1468-1477. doi:10.3969/j.issn. 1000-2561.2017.08.016.
    [23] LIU F Z, ZHOU M Q, BAN X W, et al. Comparative trial of 11 cultivars of Coix lacryma-jobi L.[J]. Chin J Trop Crops, 2016, 37(9):1670-1676. doi:10.3969/j.issn.1000-2561.2016.09.003.刘凡值, 周明强, 班秀文, 等. 11个薏苡属牧草品种材料比较试验[J]. 热带作物学报, 2016, 37(9):1670-1676. doi:10.3969/j.issn.1000-2561. 2016.09.003.
    [24] LI X K, GU K, LIANG M W, et al. Research progress on chemical constituents and pharmacological effects of Coicis semen[J]. Chin Trad Herb Drugs, 2020, 51(21):5645-5657. doi:10.7501/j.issn.0253-2670.2020.21.031.李晓凯, 顾坤, 梁慕文, 等. 薏苡仁化学成分及药理作用研究进展[J]. 中草药, 2020, 51(21):5645-5657. doi:10.7501/j.issn.0253-2670. 2020.21.031.
    [25] GUO Y L, FU H Y, HUANG G H, et al. Allelopathy effects of ferulic acid and coumarin on Microcystis aeruginosa[J]. Environ Sci, 2013, 34(4):1492-1497. doi:10.13227/j.hjkx.2013.04.001.郭亚丽, 傅海燕, 黄国和, 等. 阿魏酸和香豆素对铜绿微囊藻的化感作用[J]. 环境科学, 2013, 34(4):1492-1497. doi:10.13227/j.hjkx. 2013.04.001.
    [26] HE S S, WANG L, LI J, et al. Study on extraction and biological activity of coumalic acid from Spirulina platensis[J]. Food Indust, 2018, 39(8):1-5.何善生, 王力, 李健, 等. 螺旋藻中香豆酸的提取及其生物活性研究[J]. 食品工业, 2018, 39(8):1-5.
    [27] HE Z X, MAO P S, SUN Y, et al. Review of the current status of grass seed coating technology[J]. Acta Prata Sin, 2016, 24(2):270-277. doi:10.11733/j.issn.1007-0435.2016.02.005.何祖欣, 毛培胜, 孙彦, 等. 草类种子包衣技术现状综述[J]. 草地学报, 2016, 24(2):270-277. doi:10.11733/j.issn.1007-0435.2016.02.005.
    [28] DEVARAJ R D, JEEPIPALLI S P K, XU B J. Phytochemistry and health promoting effects of Job's tears (Coix lacryma-jobi):A critical review[J]. Food Biosci, 2020, 34:100537. doi:10.1016/j.fbio.2020. 100537.
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魏艳梅,周丽琬,陈惠琴,杨理,杨小雨,刘凡值,梅文莉,徐幸莲,戴好富.薏苡糠壳的化学成分及其种子萌发活性研究[J].热带亚热带植物学报,2021,29(5):556~562

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  • Received:November 24,2020
  • Revised:January 25,2021
  • Online: September 23,2021
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