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珊瑚共附生黄柄曲霉次级代谢产物研究

王洪亮,  姜文丽,  李冉,  许聪聪,  张文

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文章导航 > 药学实践与服务  > 2019 >  37(2): 151-155
王洪亮, 姜文丽, 李冉, 许聪聪, 张文. 珊瑚共附生黄柄曲霉次级代谢产物研究[J]. 药学实践与服务, 2019, 37(2): 151-155. doi: 10.3969/j.issn.1006-0111.2019.02.010
引用本文: 王洪亮, 姜文丽, 李冉, 许聪聪, 张文. 珊瑚共附生黄柄曲霉次级代谢产物研究[J]. 药学实践与服务, 2019, 37(2): 151-155. doi: 10.3969/j.issn.1006-0111.2019.02.010
shu
WANG Hongliang, JIANG Wenli, LI Ran, XU Congcong, ZHANG Wen. Study on the secondary metabolites of Aspergillus flavipes isolated from coral[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(2): 151-155. doi: 10.3969/j.issn.1006-0111.2019.02.010
Citation: WANG Hongliang, JIANG Wenli, LI Ran, XU Congcong, ZHANG Wen. Study on the secondary metabolites of Aspergillus flavipes isolated from coral[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(2): 151-155. doi: 10.3969/j.issn.1006-0111.2019.02.010
shu

珊瑚共附生黄柄曲霉次级代谢产物研究

doi: 10.3969/j.issn.1006-0111.2019.02.010
  • 1.

    海军军医大学药学院 上海 200433;陆军军医大学士官学校, 河北 石家庄 050000

  • 2.

    海军军医大学药学院 上海 200433

  • 3.

    安徽中医药大学, 安徽 合肥 230000

基金项目: 国家自然科学基金（41576157）

Study on the secondary metabolites of Aspergillus flavipes isolated from coral

  • 1.

    Research Center for Marine Drugs, School of Pharmacy, Naval Medical University, Shanghai 200433, China;Sergeant School of Army Medical University, Shijiazhuang 050000, China

  • 2.

    Research Center for Marine Drugs, School of Pharmacy, Naval Medical University, Shanghai 200433, China

  • 3.

    Anhui University of Chinese Medicine, Hefei 230038, China

  • 摘要: 目的 研究东沙短足软珊瑚（Cladiella sp.）来源的黄柄曲霉菌（Aspergillus flavipes）中的活性次级代谢产物。 方法 采用硅胶柱层析、凝胶柱层析、制备HPLC等分离手段对真菌发酵液乙酸乙酯提取物进行分离，运用现代波谱技术结合文献报道数据，对化合物的结构进行鉴定；采用核因子κB受体活化因子配基（RANKL）诱导小鼠骨髓单核巨噬细胞（bone marrow macrophage cells，BMMs）分化为成熟的破骨细胞，经抗酒石酸酸性磷酸酶（TRAP）特异性染色，对化合物抑制破骨细胞分化活性进行研究。 结果 从该株真菌中分离得到4个细胞松弛素类化合物，其结构鉴定为trichalasins H，aspergilluchalasin，aspochalasin I和aspochalasin D。体外活性测试结果显示，化合物3和4可不同程度抑制BMMs向破骨细胞分化。 结论 对化合物3和4抑制破骨细胞分化活性的报告是本文首次报道，对新型抗骨质疏松活性物质研究具有科学价值。
    Abstract: Objective To investigate the active secondary metabolites of coral derived fungi Aspergillus flavipes. Methods Compounds were isolated and purified by means of various chromatographic techniques,including Silica gel column chromatography,Sephadex LH-20 chromatography and HPLC.The structure of the compounds was identified by NMR combined with the data reported.The nuclear factor kappa B receptor activating factor ligand (RANKL) was used to induce bone marrow macrophage cells (BMMs) differentiate into mature osteoclasts.The tartrate-resistant acid phosphatase (TRAP) specific staining was used to test the inhibitory activity of compounds on osteoclast differentiation. Results Four cytochalasins were isolated from the fungus and their structures were identified as trichalasins H,aspergilluchalasin,aspochalasin I and aspochalasin D.Compounds 3 and 4 showed inhibitory activity on osteoclast differentiation. Conclusion This was the first report of inhibiting osteoclast differentiation activity of compounds 3 and 4.These two compounds might have great significance in the study of new anti-osteoporosis drugs.
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    [2] ZHU W M,WANG J F.A review on studies of secondary metabolites from marine fungi[J].Mycosystema,2011,30(2):218-228.
    [3] 宋双,许佳怡.海洋来源的曲霉属真菌次级代谢产物及其活性研究进展[J].中山大学研究生学刊:自然科学与医学版,2015(3):20-32.
    [4] ROCHFORT S,FORD J,OVENDEN S,et al.A novel aspochalasin with HIV-1 integrase inhibitory activity from Aspergillus flavipes[J].J Antibiot,2005,58(4):279-283.
    [5] ZHOU G X,WIJERATNE E M K,BIGELOW D,et al.Aspochalasins I,J,and K:Three new cytotoxic cytochalasans of Aspergillus flavipes from the Rhizosphere of Ericameria laricifolia of the Sonoran desert1[J].J Nat Prod,2004,67(3):328-332.
    [6] BARROW C J,SUN H H.Spiroquinazoline,a novel substance P inhibitor with a new carbon skeleton,isolated from Aspergillus flavipes[J].J Nat Prod,1994,57(4):471-476.
    [7] KWON YJ,MJ,CJ,et al.Flavimycins A and B,dimeric 1,3-dihydroisobenzofurans with peptide deformylase inhibitory activity from Aspergillus flavipes[J].J Nat Prod,2012,75(2):271-274.
    [8] EL AMRANI M,LAI D,DEBBAB A,et al.Protein kinase and HDAC inhibitors from the endophytic fungus Epicoccum nigrum[J].J Nat Prod,2014,77(1):49-56.
    [9] RUKACHAISIRIKUL V,RUNGSAIWATTANA N,KLAIKLAY S,et al.γ-Butyrolactone,cytochalasin,cyclic carbonate,eutypinic acid,and phenalenone derivatives from the soil fungus Aspergillus sp.PSU-RSPG185[J].J Nat Prod,2014,77(11):2375-2382.
    [10] CHEN L,LIU Y T,SONG B,et al.Stereochemical determination of new cytochalasans from the plant endophytic fungus Trichoderma gamsii.[J].Fitoterapia,2014,96(3):115-122.
    [11] CHOO S J,YUN B S,RYOO I J,et al.Aspochalasin I,a melanogenesis inhibitor from Aspergillus sp.[J].J Microbiol Biotechnol,2009,19(4):368-371.
    [12] TOMIKAWA T,SHIN-YA K,KINOSHITA T,et al.Selective cytotoxicity and stereochemistry of aspochalasin D[J].J Antibiot,2001,54(4):379-381.
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    [14] IWAMOTO C,YAMADA T,ITO Y,et al.Cytotoxic cytochalasans from a Penicillium,species separated from a marine alga[J].Tetrahedron,2001,57(15):2997-3004.
    [15] QUANG D N,STADLER M,FOURNIER J,et al.Carneic acids A and B,chemotaxonomically significant antimicrobial agents from the xylariaceous ascomycete Hypoxylon carneum[J].J Nat Prod,2006,69(8):1198-1202.
    [16] ALVI K A,NAIR B,PU H,et al.Phomacins:Three novel antitumor cytochalasan constituents produced by a Phoma sp.[J].J Org Chem,1997,62(7):2148-2151.
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    [18] SI Y,TANG M,LIN S,et al.Cytotoxic cytochalasans from Aspergillus flavipes PJ03-11 by OSMAC method[J].Tetrahedron Letters,2018,59(18):1767-1771.
    [19] ZHAI Z J,LI H W,LIU G W,et al.Andrographolide suppresses RANKL-induced osteoclastogenesis in vitro and prevents inflammatory bone loss in vivo[J].Br J Pharmacol,2014,171(3):663-675.
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  • 收稿日期:  2018-11-04
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珊瑚共附生黄柄曲霉次级代谢产物研究

doi: 10.3969/j.issn.1006-0111.2019.02.010
  • 1. 海军军医大学药学院 上海 200433;陆军军医大学士官学校, 河北 石家庄 050000
  • 2. 海军军医大学药学院 上海 200433
  • 3. 安徽中医药大学, 安徽 合肥 230000
    • 基金项目:  国家自然科学基金（41576157）
  • 收稿日期: 2018-11-04
  • 修回日期: 2019-03-04

摘要: 目的 研究东沙短足软珊瑚（Cladiella sp.）来源的黄柄曲霉菌（Aspergillus flavipes）中的活性次级代谢产物。 方法 采用硅胶柱层析、凝胶柱层析、制备HPLC等分离手段对真菌发酵液乙酸乙酯提取物进行分离，运用现代波谱技术结合文献报道数据，对化合物的结构进行鉴定；采用核因子κB受体活化因子配基（RANKL）诱导小鼠骨髓单核巨噬细胞（bone marrow macrophage cells，BMMs）分化为成熟的破骨细胞，经抗酒石酸酸性磷酸酶（TRAP）特异性染色，对化合物抑制破骨细胞分化活性进行研究。 结果 从该株真菌中分离得到4个细胞松弛素类化合物，其结构鉴定为trichalasins H，aspergilluchalasin，aspochalasin I和aspochalasin D。体外活性测试结果显示，化合物3和4可不同程度抑制BMMs向破骨细胞分化。 结论 对化合物3和4抑制破骨细胞分化活性的报告是本文首次报道，对新型抗骨质疏松活性物质研究具有科学价值。

English Abstract

王洪亮, 姜文丽, 李冉, 许聪聪, 张文. 珊瑚共附生黄柄曲霉次级代谢产物研究[J]. 药学实践与服务, 2019, 37(2): 151-155. doi: 10.3969/j.issn.1006-0111.2019.02.010
引用本文: 王洪亮, 姜文丽, 李冉, 许聪聪, 张文. 珊瑚共附生黄柄曲霉次级代谢产物研究[J]. 药学实践与服务, 2019, 37(2): 151-155. doi: 10.3969/j.issn.1006-0111.2019.02.010
shu
WANG Hongliang, JIANG Wenli, LI Ran, XU Congcong, ZHANG Wen. Study on the secondary metabolites of Aspergillus flavipes isolated from coral[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(2): 151-155. doi: 10.3969/j.issn.1006-0111.2019.02.010
Citation: WANG Hongliang, JIANG Wenli, LI Ran, XU Congcong, ZHANG Wen. Study on the secondary metabolites of Aspergillus flavipes isolated from coral[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(2): 151-155. doi: 10.3969/j.issn.1006-0111.2019.02.010
shu

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