Monoterpenoids from the root bark of Acanthopanax gracilistylus and their inhibitory effects on neutrophil elastase, 5-lipoxygenase, andcyclooxygenase-2 in vitro

被引:4
作者
Yang, Hao-Dong [1 ]
Tang, Zhi-Shu [1 ,2 ]
Xue, Tao-Tao [1 ]
Xu, Huai-Li [1 ]
Hou, Bao-Long [1 ]
Zhu, Ya-Ya [1 ]
Su, Zeng-Hu [1 ]
Xu, Hong-Bo [1 ]
机构
[1] Shaanxi Univ Chinese Med, Coconstruct Collaborat Innovat Ctr Chinese Med Res, State Key Lab Res & Dev Characterist Qin Med Resou, Xianyang 712083, Peoples R China
[2] China Acad Chinese Med Sci, Beijing 100700, Peoples R China
基金
中国国家自然科学基金;
关键词
Acanthopanacis cortex; Araliaceae; Monoterpenoids; Neutrophil elastase; 5-Lipoxygenase; Cyclooxygenase-2; ALPHA-PINENE; BETA-PINENE; TERPENOIDS; PRODUCTS; BIOTRANSFORMATION; TRANSFORMATIONS; IDENTIFICATION; CONSTITUENTS; OZONOLYSIS; PINANE;
D O I
10.1016/j.phytochem.2023.113851
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Twenty-four monoterpenoids, including three previously undescribed compounds (1-3), were isolated from the root bark of Acanthopanax gracilistylus W. W. Smith (Acanthopanacis Cortex). Their structures were unambiguously established based on spectroscopic analysis (HR-ESIMS, IR, 1D, and 2D NMR), and the absolute configurations of 1-3 were elucidated by comparing their experimental and calculated electronic circular dichroism spectra. In addition, the structure of 8 was confirmed by single-crystal X-ray diffraction. The inhibitory activities of 1-24 against neutrophil elastase, 5-lipoxygenase, and cyclooxygenase-2 (COX-2) were studied in vitro for the first time, and the results showed that compound 24 possessed a significant inhibitory effect on COX-2 with an IC50 value of 1.53 +/- 0.10 mu\M. This research first reported the presence of monoterpenoids in Acanthopanacis Cortex, including one monoterpenoid 2 with an unusual 4/5 bicyclic lactone system, and compounds 4 and 5 have never been reported in nature.
引用
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页数:8
相关论文
共 44 条
  • [1] Becker H, 1999, Z NATURFORSCH C, V54, P997
  • [2] Optically active organotin compounds derived from β-pinene.: The quest for chiral polystannanes
    Beckmann, Jens
    Duthie, Andrew
    Grassmann, Marian
    Semisch, Annetta
    [J]. ORGANOMETALLICS, 2008, 27 (07) : 1495 - 1500
  • [3] Chacko Susan, 2000, Fitoterapia, V71, P616, DOI 10.1016/S0367-326X(00)00195-7
  • [4] Chinese Pharmacopeia Commission, 2020, Pharmacopoeia of the People's Republic of China Version, P67
  • [5] OLEX2: a complete structure solution, refinement and analysis program
    Dolomanov, Oleg V.
    Bourhis, Luc J.
    Gildea, Richard J.
    Howard, Judith A. K.
    Puschmann, Horst
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 : 339 - 341
  • [6] Terpenoids and phenethyl glucosides from Hyssopus cuspidatus (Labiatae)
    Furukawa, Megumi
    Makino, Mitsuko
    Ohkoshi, Emika
    Uchiyama, Taketo
    Fujimoto, Yasuo
    [J]. PHYTOCHEMISTRY, 2011, 72 (17) : 2244 - 2252
  • [7] Galli R, 2002, HELV CHIM ACTA, V85, P3400, DOI 10.1002/1522-2675(200210)85:10<3400::AID-HLCA3400>3.0.CO
  • [8] 2-2
  • [9] P450camr, a cytochrome P450 catalysing the stereospecific 6-endo-hydroxylation of (1R)-(+)-camphor
    Grogan, G
    Roberts, GA
    Parsons, S
    Turner, NJ
    Flitsch, SL
    [J]. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2002, 59 (4-5) : 449 - 454
  • [10] Reactions of allyl alcohols of the pinane series and of their epoxides in the presence of montmorillonite clay
    Il'ina, Irina V.
    Volcho, Konstantin P.
    Korchagina, Dina V.
    Barkhash, Vladimir A.
    Salakhutdinov, Nariman F.
    [J]. HELVETICA CHIMICA ACTA, 2007, 90 (02) : 353 - 368