Yupeng LI, Xinglong CHEN, Shengxing YUAN, Yajuan CHEN, Rongping ZHANG. Chemical Compounds Isolated from Cremastra Appendiculata and Their Bioactive Activity[J]. Journal of Kunming Medical University, 2023, 44(2): 1-6. doi: 10.12259/j.issn.2095-610X.S20230209
Citation: Yupeng LI, Xinglong CHEN, Shengxing YUAN, Yajuan CHEN, Rongping ZHANG. Chemical Compounds Isolated from Cremastra Appendiculata and Their Bioactive Activity[J]. Journal of Kunming Medical University, 2023, 44(2): 1-6. doi: 10.12259/j.issn.2095-610X.S20230209

Chemical Compounds Isolated from Cremastra Appendiculata and Their Bioactive Activity

doi: 10.12259/j.issn.2095-610X.S20230209
  • Received Date: 2022-12-16
    Available Online: 2023-01-31
  • Publish Date: 2023-02-25
  •   Objective  To study the chemical compounds from the medicinal plants of Cremastra appendiculata and find its antitumor bioactive compounds.   Methods  The compounds were extracted by alcohol (95%) and isolated by column chromatography on silica gel and Sephadex LH-20. Their structures were identified by spectroscopic analysis (1H NMR, 13CNMR and EIMS). The antitumor activity of the compounds was studied by MTT assay in vitro.   Results  Twelve compounds were obtained and identified as bisbenzopyran (1), (22E)-ergosta-6, 22-dien-3β, 5α, 8α-triol (2), 3β-hydroxycholesta-5-ene (3), β-sistosterol (4), pinoresinol (5), 5, 4′-dihydroxy-7- (4-hydroxybenzoyl) -3′- methoxyflavone (6), 4-methoxy-2, 3, 7- trihydroxyphenanthrene (7), 2-hydroxy-4, 7-dimethoxyphenanthrene (8), 4, 4′-dimethoxy-[1, 1′-biphenanthrene]- 2, 2′, 7, 7′-tetrol (9), 4, 7, 4′, 9′-tetramethoxy-[1, 1′-biphenanthrene] 2, 2′, 7, 7′-tetrol (10), Bavachinine (11), 3-hydroxyphenpropionic acid- (2′-methoxy-4′- carboxy-phenol) ester (12); . The results of anti-tumor activity test of compounds 7~12 showed that 9 and 10 showed good inhibitory activity on MCF-7/S cell line.  Conclusions   Compounds 2, 3, 5, 7, 10 and 12 were isolated from this plant for the first time. IC50 of 9 and 10 on MCF-7/S cell lines were 2.16 and 5.09 respectively μmol/L.
  • [1]
    中国科学院中国植物志编辑委员会. 中国植物志(第18卷)[M]. 北京: 科学出版社, 1999: 164-167.
    [2]
    董海玲,郭顺星,王春兰,等. 山慈菇的化学成分和药理作用研究进展[J]. 中草药,2007,38(11):1734-1738. doi: 10.3321/j.issn:0253-2670.2007.11.048
    [3]
    Saleem R,Faizi S,Deeba F,et al. A New Bisbenzopyran from Aloe barbadensis Roots[J]. Planta Medica,1997,63(5):454-456. doi: 10.1055/s-2006-957732
    [4]
    Rivera A,Benavides OL,Rios-Motta J. (22E)-Ergosta-6,22-diene-3β,5α,8α-triol: A new polyhydroxysterol isolated from Lentinus edodes (Shiitake)[J]. Natural Product Research,2009,23(3):293-300. doi: 10.1080/14786410802038671
    [5]
    刘涛,李占林,王宇,等. 海洋来源真菌Hypocrea virens的次级代谢产物研究[J]. 沈阳药科大学学报,2012,29(2):93-97.
    [6]
    张海龙,田黎,付红伟,等. 海洋真菌Alternalia sp. 发酵液中化学成分的研究[J]. 中国中药杂志,2005,30(5):351. doi: 10.3321/j.issn:1001-5302.2005.05.008
    [7]
    Wang Z,Xu F,An S. Chemical constituents from the root bark of Dictamnus dasycarpus Turcz[J]. China journal of Chinese materia medica,1992,17(9):551-552,576.
    [8]
    Li S R,Yang H,Tan C,et al. Chemical constituents of ethyl acetate fraction from the stems of Saprosma merrillii Lo[J]. Chinese Pharmaceutical Journal,2015,50(12):1017-1020.
    [9]
    Hassan A E,Sayed M E,Hamed A I,et al. Bioactive constituents of Leptadenia arborea[J]. Fitoterapia,2003,74(1-2):184-187. doi: 10.1016/S0367-326X(02)00314-3
    [10]
    Ahmad I,Janbaz C K H. Cinerasenone,a new flavonoid from Vernonia cinerascens[J]. Journal Chemical Society of Pakistan,2010,32(1):101-103.
    [11]
    Leong Y W,Harrison L J,Powell A D. Phenanthrene and other aromatic constituents of Bulbophyllum vaginatum[J]. Phytochemistry,1999,50(7):1237-1241. doi: 10.1016/S0031-9422(98)00687-6
    [12]
    Leong Y W,Kang C C,Harrison L J,et al. Phenanthrenes,dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum[J]. Phytochemistry,1997,44(1):157-165. doi: 10.1016/S0031-9422(96)00387-1
    [13]
    Xue Z,Li S,Wang S J,et al. Mono-,Bi-,and Triphenanthrenes from the Tubers of Cremastra appendiculata[J]. Journal of Natural Products,2006,69(6):907-913. doi: 10.1021/np060087n
    [14]
    Yamaki M,Bai L,Inoue K,et al. Biphenanthrenes from Bletilla striata[J]. Phytochemistry,1989,28(12):3503-3505. doi: 10.1016/0031-9422(89)80373-5
    [15]
    Wang C,Shao S Y,Han S W,et al. Atropisomeric bi (9,10-dihydro) phenanthrene and phenanthrene/bibenzyl dimers with cytotoxic activity from the pseudobulbs of Pleione bulbocodioides[J]. Fitoterapia,2019,138:1-7.
    [16]
    Trinh P T N,Hao N C,Thao P T,et al. Chemical components of the rhizomes of Drynaria fortunei (KUNZE) J. Sm. (polypodiaceae) in Vietnam[J]. Collection of Czechoslovak Chemical Communications,2011,76(9):1133-1139. doi: 10.1135/cccc2010098
    [17]
    Xu Q X,Ying,Li G Y,Xu W,et al. Multi-Target Anti-Alzheimer Activities of Four Prenylated Compounds from Psoralea Fructus[J]. Molecules,2018,23(614):1-12.
    [18]
    Wang Y,Guan S H,Meng Y H,et al. Phenanthrenes,9,10-dihydrophenanthrenes,bibenzyls with their derivatives,and malate or tartrate benzyl ester glucosides from tubers of Cremastra appendiculata[J]. Phytochemistry,2013,94:268-276. doi: 10.1016/j.phytochem.2013.06.001
    [19]
    Liu L,Li J,Zeng K W,et al. Five New Biphenanthrenes from Cremastra appendiculata[J]. Molecules,2016,21(8):1-10.
    [20]
    陈诗,赵玥,王振,等. 山慈菇药理作用及临床应用研究进展[J]. 中华中医药学刊,2022,29(12):1-14.
    [21]
    司函瑞,司雨,焦玉凤,等. 山慈菇化学成分及其药理作用研究进展[J]. 辽宁中医药大学学报,2020,22(5):151-155.
    [22]
    王宏伟,田欣圆,于蕾. 山慈菇的化学成分及其抗肿瘤作用机制研究进展[J]. 内蒙古医科大学学报,2022,44(3):305-309.
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