Speramides A-B, two new prenylated indole alkaloids from the freshwater-derived fungus Aspergillus ochraceus KM007

被引：24
作者：
Chang, Yao-Wen [1 ,2 ,4 ]
Yuan, Chun-Mao [1 ,2 ]
Zhang, Jing [1 ,3 ]
Liu, Shuai [1 ,4 ]
Cao, Pei [1 ,4 ]
Hua, Hui-Ming [2 ]
Di, Ying-Tong [1 ,4 ]
Hao, Xiao-Jiang [1 ,4 ]
机构：
[1] Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming Inst Bot, Kunming 650201, Yunnan, Peoples R China
[2] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Liaoning, Peoples R China
[3] Xinjiang Med Univ, Sch Chinese Tradit Med, 393 Xinyi Rd, Urumqi 830011, Xinjiang, Peoples R China
[4] Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 45期
基金：
中国国家自然科学基金;
关键词：
Speramide; Brevianamide; Prenylated indole alkaloid; Aspergillus ochraceus; Notoamide; STEREOCONTROLLED TOTAL-SYNTHESIS; NOTOAMIDE-B; STEPHACIDIN; BIOSYNTHESIS;
D O I：
10.1016/j.tetlet.2016.09.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two new prenylated indole alkaloids, named Speramides A (1) and B (2) were isolated from the extraction of the freshwater-derived fungus Aspergillus ochraceus KM007. Their structures were elucidated by means of spectroscopic analysis. Compound 1 is the first prenylated brevianamide derivative. These compounds isolated were evaluated for their antimicrobial activity, among which, compound 1 showed moderate activity against Pseudomonas aeruginosa with a MIC value of 0.8 mu M. (C) 2016 Published by Elsevier Ltd.
引用
收藏
页码：4952 / 4955
页数：4
相关论文
共 26 条
  • [1] Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B
    Artman, Gerald D., III
    Grubbs, Alan W.
    Williams, Robert M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (19) : 6336 - 6342
  • [2] Bioactive Indole Alkaloids and Phenyl Ether Derivatives from a Marine-Derived Aspergillus sp Fungus
    Chen, Min
    Shao, Chang-Lun
    Fu, Xiu-Mei
    Xu, Ru-Fang
    Zheng, Juan-Juan
    Zhao, Dong-Lin
    She, Zhi-Gang
    Wang, Chang-Yun
    [J]. JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04): : 547 - 553
  • [3] Genome-Based Characterization of Two Prenylation Steps in the Assembly of the Stephacidin and Notoamide Anticancer Agents in a Marine-Derived Aspergillus sp.
    Ding, Yousong
    de Wet, Jeffrey R.
    Cavalcoli, James
    Li, Shengying
    Greshock, Thomas J.
    Miller, Kenneth A.
    Finefield, Jennifer M.
    Sunderhaus, James D.
    McAfoos, Timothy J.
    Tsukamoto, Sachiko
    Williams, Robert M.
    Sherman, David H.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (36) : 12733 - 12740
  • [4] Unprecedented Quassinoids with Promising Biological Activity from Harrisonia perforata
    Fang, Xin
    Di, Ying Tong
    Zhang, Yu
    Xu, Zhi Ping
    Lu, Yang
    Chen, Qian Qian
    Zheng, Qi Tai
    Hao, Xiao Jiang
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) : 5592 - 5595
  • [5] Fungal Origins of the Bicyclo[2.2.2]diazaoctane Ring System of Prenylated Indole Alkaloids
    Finefield, Jennifer M.
    Frisvad, Jens C.
    Sherman, David H.
    Williams, Robert M.
    [J]. JOURNAL OF NATURAL PRODUCTS, 2012, 75 (04): : 812 - 833
  • [6] Biosynthetic Studies of the Notoamides: Isotopic Synthesis of Stephacidin A and Incorporation into Notoamide B and Sclerotiamide
    Finefield, Jennifer M.
    Kato, Hikaru
    Greshook, Thomas J.
    Sherman, David H.
    Tsukamoto, Sachiko
    Williams, Robert M.
    [J]. ORGANIC LETTERS, 2011, 13 (15) : 3802 - 3805
  • [7] Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600
    Greshock, Thomas J.
    Grubbs, Alan W.
    Jiao, Ping
    Wicklow, Donald T.
    Gloer, James B.
    Williams, Robert M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) : 3573 - 3577
  • [8] Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)
    Kagiyama, Ippei
    Kato, Hikaru
    Nehira, Tatsuo
    Frisvad, Jens C.
    Sherman, David H.
    Williams, Robert M.
    Tsukamoto, Sachiko
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (03) : 1128 - 1132
  • [9] Kato H., 2007, Angrew Chem, V119, P2304
  • [10] Isolation of Notoamide S and Enantiomeric 6-epi-Stephacidin A from the Fungus Aspergillus amoenus: Biogenetic Implications
    Kato, Hikaru
    Nakahara, Takashi
    Sugimoto, Kayo
    Matsuo, Kanae
    Kagiyama, Ippei
    Frisvad, Jens C.
    Sherman, David H.
    Williams, Robert M.
    Tsukamoto, Sachiko
    [J]. ORGANIC LETTERS, 2015, 17 (03) : 700 - 703
123