ZHANG Liangcong, SUN Li, CHEN Min, HUANG Wuyang, SHEN Li. Study on antioxidant activity of azaphilone compound Penicilone B in vitro
[J]. Journal of Clinical Medicine in Practice, 2021, 25(2): 5-9. DOI: 10.7619/jcmp.20201341
Citation: ZHANG Liangcong, SUN Li, CHEN Min, HUANG Wuyang, SHEN Li. Study on antioxidant activity of azaphilone compound Penicilone B in vitro
[J]. Journal of Clinical Medicine in Practice, 2021, 25(2): 5-9. DOI: 10.7619/jcmp.20201341

Study on antioxidant activity of azaphilone compound Penicilone B in vitro

More Information
  • Received Date: November 03, 2020
  • Available Online: January 26, 2021
  • Published Date: January 27, 2021
  •   Objective  To study antioxidant activity of azaphilone compound Penicilone B in vitro and analyze its antioxidant mechanism using Density Functional Theory (DFT).
      Methods  Three in vitro antioxidant methods including ABTS[2, 2′-azino-bis(3-ethylbenzothiazoline-6-sulfonate)] radical scavenging ability, DPPH (2, 2-diphenyl-1-picrylhydrazyl) radical scavenging ability and oxygen radical absorbance capacity (ORAC) assays were used to determine the antioxidant activity of an azaphilone compound Penicilone B firstly. Moreover, DFT was used to optimize molecular structure of Penicilone B and to analyze the antioxidant mechanism from the aspects of the molecular structure parameters, bond dissociation enthalpy (BDE) of the phenolic hydroxyl group, ionization potential (IP) and frontier molecular orbital (FMO) at the level of M06-2x/6-31+G**.
      Results  Penicilone B showed certain antioxidant activity in vitro. The scavenging rates of Penicilone B on ABTS radicals and DPPH radicals were (11.62±1.19)% and (22.68±2.81)% at 100 μg/mL, respectively, while the scavenging rates of positive control vitamin C (Vc) were (43.17±3.88)% and (58.73±4.70)%, respectively. In addition, the ORAC values of Penicilone B and Vc were (1.06±0.06) and (2.87±0.15) μmol trolox/mg, respectively. The DFT calculation results found that phenolic hydroxyl group at C15 position was easy to occur hydrogen-abstraction reaction. Besides, Penicilone B may also terminate the chain reaction of oxidation by directly binding to active free radicals and ring A and ring B were the primary active sites.
      Conclusion  The antioxidant mechanism of azaphilone compounds is investigated by DFT method for the first time in this study. The theoretical calculation result is in agreement with the experiment in vitro, which provides a theoretical basis for the development of azaphilones.
  • [1]
    KUDRYAVTSEVA A V, KRASNOV G S, DMITRIEV A A, et al. Mitochondrial dysfunction and oxidative stress in aging and cancer[J]. Oncotarget, 2016, 7(29): 44879-44905. doi: 10.18632/oncotarget.9821
    [2]
    CAI H, HARRISON D G. Endothelial dysfunction in cardiovascular diseases: the role of oxidant stress[J]. Circ Res, 2000, 87(10): 840-844. doi: 10.1161/01.RES.87.10.840
    [3]
    FORBES J M, COOPER M E. Mechanisms of diabetic complications[J]. Physiol Rev, 2013, 93(1): 137-188. doi: 10.1152/physrev.00045.2011
    [4]
    THANAN R, OIKAWA S, HIRAKU Y, et al. Oxidative stress and its significant roles in neurodegenerative diseases and cancer[J]. Int J Mol Sci, 2014, 16(1): 193-217. doi: 10.3390/ijms16010193
    [5]
    WU Z H, LI Y, LIU D, et al. New resorcinol derivatives from a sponge-derived fungus Hansfordia sinuosae[J]. Chem Biodivers, 2017, 14(6): e1700059. doi: 10.1002/cbdv.201700059
    [6]
    LIU Z, TAN H, CHEN K, et al. Rhizophols A and B, antioxidant and axially chiral benzophenones from the endophytic fungus Cytospora rhizophorae[J]. Org Biomol Chem, 2019, 17(47): 10009-10012. doi: 10.1039/C9OB02282A
    [7]
    CHEN M, SHEN N X, CHEN Z Q, et al. Penicilones A-D, anti-MRSA azaphilones from the marine-derived fungus Penicillium janthinellum HK1-6[J]. J Nat Prod, 2017, 80(4): 1081-1086. doi: 10.1021/acs.jnatprod.6b01179
    [8]
    OSMANOVA N, SCHULTZE W, AYOUB N. Azaphilones: a class of fungal metabolites with diverse biological activities[J]. Phytochem Rev, 2010, 9(2): 315-342. doi: 10.1007/s11101-010-9171-3
    [9]
    GAO J M, YANG S X, QIN J C. Azaphilones: chemistry and biology[J]. Chem Rev, 2013, 113(7): 4755-4811. doi: 10.1021/cr300402y
    [10]
    RE R, PELLEGRINI N, PROTEGGENTE A, et al. Antioxidant activity applying an improved ABTS radical cation decolorization assay[J]. Free Radic Biol Med, 1999, 26(9/10): 1231-1237. http://www.bioone.org/servlet/linkout?suffix=i0031-8655-81-3-623-b31&dbid=8&doi=10.1562%2F2004-06-14-RA-200.1&key=10381194
    [11]
    HUANG D J, OU B X, PRIOR R L. The chemistry behind antioxidant capacity assays[J]. J Agric Food Chem, 2005, 53(6): 1841-1856. doi: 10.1021/jf030723c
    [12]
    FRISCH M J, TRUCKS G W, SCHLEGEL H B, et al. Gaussian 16, Revision A.03[CP]. Wallingford CT: Gaussian, Inc., 2016.
    [13]
    GLAZER A N. Fluorescence-based assay for reactive oxygen species: a protective role for creatinine[J]. Faseb J, 1988, 2(9): 2487-2491. doi: 10.1096/fasebj.2.9.3371593
    [14]
    GUAN X H, WANG D, WANG Q, et al. Estimation of various chemical bond dissociation enthalpies of large-sized kerogen molecules using DFT methods[J]. Mol Phys, 2016, 114(11): 1705-1755. doi: 10.1080/00268976.2016.1143983
    [15]
    BLANKSBY S J, ELLISON G B. Bond dissociation energies of organic molecules[J]. Accounts Chem Res, 2003, 36(4): 255-263. doi: 10.1021/ar020230d
    [16]
    郑文锐, 傅尧, 王华静, 等. 烃类化合物碳氢键解离焓的密度泛函理论研究[J]. 有机化学, 2008, 28(3): 459-466. https://www.cnki.com.cn/Article/CJFDTOTAL-YJHU200803016.htm
    [17]
    汤定华, 杨频. 前线分子轨道与化学反应性[J]. 山西大学学报: 自然科学版, 1978, 1(1): 26-46. https://www.cnki.com.cn/Article/CJFDTOTAL-SXDR197801002.htm
    [18]
    SAY-LIANG-FAT S, CORNARD J P. Al(Ⅲ) complexation by alizarin studied by electronic spectroscopy and quantum chemical calculations[J]. Polyhedron, 2011, 30(13): 2326-2332. doi: 10.1016/j.poly.2011.06.014
    [19]
    SUN W W, WU W H, LIU X L, et al. Bioactive compounds isolated from marine-derived microbes in China: 2009-2018[J]. Mar Drugs, 2019, 17(6): 339-345. doi: 10.3390/md17060339
  • Related Articles

    [1]ZOU Yingcai, ZHOU Li, WANG Jiangning, GAO Lei. Effects of antibiotic-loaded bone cement coverage versus negative pressure wound therapy on diabetic foot ulcer wound healing[J]. Journal of Clinical Medicine in Practice, 2024, 28(23): 105-109, 115. DOI: 10.7619/jcmp.20243314
    [2]WANG Haihong, XU Yinan, JIAO Hao. Role of chlorophyll derivative in improving wound healing after hemorrhoidectomy[J]. Journal of Clinical Medicine in Practice, 2024, 28(1): 90-93. DOI: 10.7619/jcmp.20232914
    [3]YANG Yuan, YU Chenghao, ZUO Rui, LIU Zhe, FU Yi, HOU Ruixing. Research progress on role and mechanism of angiopoietin-like protein 4 in skin wound healing[J]. Journal of Clinical Medicine in Practice, 2022, 26(23): 134-137, 142. DOI: 10.7619/jcmp.20222677
    [4]XIE Zhennian, AN Xiaojing, ZHOU Haiyang, WANG Fangli, WANG Liping. Effect of compound chamomile and lidocaine hydrochloride gel on skin wound healing in rats[J]. Journal of Clinical Medicine in Practice, 2022, 26(17): 18-23. DOI: 10.7619/jcmp.20222308
    [5]XIONG Shi, SUN Changsheng, LIN Cuiling. Effect of skin soft tissue expansion and composite skin transplantation on recovery time of wound healing and skin blood supply in burn patients[J]. Journal of Clinical Medicine in Practice, 2020, 24(13): 26-28. DOI: 10.7619/jcmp.202013008
    [6]LI Yanhui, ZHANG Li, XIAO Houan. Therapeutic effect of local oxygen therapy on woundhealing in patients with chronic wound skin graft[J]. Journal of Clinical Medicine in Practice, 2019, 23(13): 27-29. DOI: 10.7619/jcmp.201913007
    [7]CAO Fangmin, WANG Chunmei, LI Shan. Effect of different cold compress methods on postoperative pain and wound healing after tonsillectomy[J]. Journal of Clinical Medicine in Practice, 2019, 23(9): 81-84. DOI: 10.7619/jcmp.201909023
    [8]WANG Chunmei, CAO Fangmin, XU Min, CHENG Fang. Effect of evidence-based pain nursing on postoperative pain and wound healing in patients with hemorrhoid surgery[J]. Journal of Clinical Medicine in Practice, 2019, 23(8): 104-107. DOI: 10.7619/jcmp.201908029
    [9]HU Liang, SUN Bingwei, XIAO Guixi, YU Ye. Effect of bioactive glass combined with bath therapy on treatment of patients with residual burn wound[J]. Journal of Clinical Medicine in Practice, 2014, (9): 72-75. DOI: 10.7619/jcmp.201409020
    [10]LIU Min, ZHANG Bing, ZHANG Liping. Influence of comprehensive nursing intervention on healing of wound in patients with anterior cervical operation[J]. Journal of Clinical Medicine in Practice, 2013, (12): 74-76. DOI: 10.7619/jcmp.201312028
  • Cited by

    Periodical cited type(6)

    1. 沈良伟,李涛,金祝华,黄刚. CT定位辅助神经内镜手术对脑包虫病的疗效分析. 临床神经病学杂志. 2023(01): 39-43 .
    2. 廖佳奇,许金仙,叶新运,温小华. 桥小脑角肿瘤微创切除术中应用神经内镜对其功能恢复及预后的影响. 广州医药. 2023(05): 61-64+69 .
    3. 宋少谦. 神经内镜辅助显微手术治疗囊性脑肿瘤的疗效观察. 临床研究. 2022(11): 8-11 .
    4. 蔡昌呈,陈星宇,向城卫,刘应刚,李维民,罗可. 神经内镜联合颅底显微神经外科手术对脑肿瘤患者的影响. 内蒙古医科大学学报. 2022(06): 634-636+640 .
    5. 侯晓峰,张春阳. 探讨神经内镜辅助显微手术应用于囊性脑肿瘤患者治疗的临床效果. 影像研究与医学应用. 2020(13): 219-220 .
    6. 杨文凯. 神经内镜辅助显微手术治疗囊性脑肿瘤的疗效观察. 航空航天医学杂志. 2020(11): 1342-1343 .

    Other cited types(0)

Catalog

    Article views (370) PDF downloads (51) Cited by(6)

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return