Citation: Ye Li, Kun-Lai Sun, Yi Wang, Peng Fu, Pei-Pei Liu, Chen Wang, Wei-Ming Zhu. A cytotoxic pyrrolidinoindoline diketopiperazine dimer from the algal fungus Eurotium herbariorum HT-2[J]. Chinese Chemical Letters, ;2013, 24(12): 1049-1052. shu

A cytotoxic pyrrolidinoindoline diketopiperazine dimer from the algal fungus Eurotium herbariorum HT-2

  • Corresponding author: Wei-Ming Zhu, 
  • Received Date: 7 April 2013
    Available Online: 25 June 2013

    Fund Project: This work is financially supported by NSFC (No. 21172204) & NSFS (No. ZR2009CQ014) (No. 21172204) and Scientific Research Foundation for the Returned Overseas Chinese Scholars, Ministry of Education of China (No. [2010]1174). (No. 2010CB833804)

  • A new cytotoxic pyrrolidinoindoline diketopiperazine dimer, cristatumin E (1), was isolated from the fermentation broth of the algal fungus Eurotium herbariorum HT-2 associated with the marine algae, Enteromorpha prolifera. The structure was determined by spectroscopic analyses and Marfey's amino acid analysis. Cristatumin E (1) showed cytotoxicity against K562 tumor cell line and antibacterial activity against Enterobacter aerogenes and Escherichia coli with IC50 and MIC values of 8.3, 44.0 and 44.0 μmol/L, respectively.
  • 加载中
    1. [1]

      [1] W.H. Gerwick, B.S. Moore, Lessons from the past and charting the future of marine natural products drug discovery and chemical biology, Chem. Biol. 19 (2012) 85- 98.

    2. [2]

      [2] H. Greve, I.E. Mohamed, A. Pontius, et al., Fungal metabolites: structural diversity as incentive for anticancer drug development, Phytochem. Rev. 9 (2010) 537-545.

    3. [3]

      [3] N. Benjamin, L.G. Kenneth, B.R. Miller, et al., Neuteboom STC (2006) NPI-2358 is a tubulin-depolymerization agent: in vitro evidence for activity as a tumor vascular- disrupting agent, Anticancer Drugs 17 (2006) 25-31.

    4. [4]

      [4] (a) K. Kanoh, S. Kohno, T. Asari, et al., (-)-Phenylahistin: a new mammalian cell cycle inhibitor produced by Aspergillus ustus, Bioorg. Med. Chem. Lett. 7 (1997) 2847-2852;

    5. [5]

      (b) K. Kanoh, S. Kohno, J. Katada, et al., (-)-Phenylahistin arrests cells in mitosis by inhibiting tubulin polymerization, J. Antibiot. 52 (1999) 134-141;

    6. [6]

      (c) K. Kanoh, S. Kohno, J. Katada, et al., Antitumor activity of phenylahistin in vitro and in vivo, Biosci. Biotechnol. Biochem. 63 (1999) 1130-1133.

    7. [7]

      [5] (a) J.K. Zheng, H.J. Zhu, K. Hong, et al., Novel cyclic hexapeptides from marinederived fungus, Aspergillus sclerotiorum PT06-1, Org. Lett. 11 (2009) 5262-5265;

    8. [8]

      (b) Z.Y. Lu, Y. Wang, C.D. Miao, et al., Sesquiterpenoids and benzofuranoids from the marine-derived fungus Aspergillus ustus 094102, J. Nat. Prod. 72 (2009) 1761- 1767;

    9. [9]

      (c) Z.Y. Lu, H.J. Zhu, P. Fu, et al., Cytotoxic polyphenols from the marine-derived fungus Penicillium expansum, J. Nat. Prod. 73 (2010) 911-914;

    10. [10]

      (d) J.K. Zheng, Z.H. Xu, Y. Wang, et al., Cyclic tripeptides from the halotolerant fungus Aspergillus sclerotiorum PT06-1, J. Nat. Prod. 73 (2010) 1133-1137;

    11. [11]

      (e) X.P. Peng, Y. Wang, K.L. Sun, et al., Cerebrosides and 2-pyridone alkaloids from the halotolerant fungus Penicillium chrysogenum grown in a hypersaline medium, J. Nat. Prod. 74 (2011) 1298-1302;

    12. [12]

      (f) Y.B. Zhuang, X.C. Teng, Y. Wang, et al., New quinazolinone alkaloids within rare amino acid residue from coral-associated fungus, Aspergillus versicolor LCJ-5-4, Org. Lett. 13 (2011) 1130-1133;

    13. [13]

      (g) Y.B. Zhuang, X.C. Teng, Y. Wang, et al., Cyclopeptides and polyketides from coral-associated fungus, Aspergillus versicolor LCJ-5-4, Tetrahedron 67 (2011) 7085-7089;

    14. [14]

      (h) J.F. Wang, Z.Y. Lu, P.P. Liu, et al., Cytotoxic polyphenols from the fungus Penicillium expansum 091006 endogenous with mangrove plant Excoecaria agallocha, Planta Med. 78 (2012) 1861-1866;

    15. [15]

      (i) J.F. Wang, P.P. Liu, Y. Wang, et al., Antimicrobial aromatic polyketides from gorgonian-associated fungus, Penicillium commune 518, Chin. J. Chem. 30 (2012) 1236-1242.

    16. [16]

      [6] K.L. Sun, Y. Wang, P. Fu, P.P. Liu, W.M. Zhu, Studies on the secondary metabolites of Eurotium herbariorum HT-2 symbiotic with Enteromorpha prolifera, Chin. Mar. Drugs 32 (2013) 37-45.

    17. [17]

      [7] J.R. Zhang, X.L. Tang, G.Q. Li, Studies on chemical constituents of Entermorpha prolifera, Period. Ocean Univ. China 40 (2010) 93-95.

    18. [18]

      [8] Y. Okai, K.H. Okai, Potent anti-inflammatory activity of pheophytin a derived from edible green alga, Entermorpha prolifera (Sujiao-Nori), Int. J. Immunopharmacol. 19 (1997) 355-358.

    19. [19]

      [9] G.J. Slack, E. Puniani, J.C. Frisvad, et al., Secondary metabolites from Eurotium species, Aspergillus calidoustus and A. insuetus common in Canadian homes with a review of their chemistry and biological activities, Mycol. Res. 113 (2009) 480- 490.

    20. [20]

      [10] V.D. Hauser, H.P. Weber, H.P. Sigg, Isolation and configuration of chaetocin, Helv. Chim. Acta 53 (1970) 1061-1073.

    21. [21]

      [11] C.R. Isham, J.D. Tibodeau, A.R. Bossou, The anticancer effects of chaetocin are independent of programmed cell death and hypoxia, and are associated with inhibition of endothelial cell proliferation, Br. J. Cancer 106 (2012) 314-323.

    22. [22]

      [12] P. Marfey, Determination of D-amino acids. II. Use of a bifunctional reagent 1,5- difluoro-2, 4-dinitrobenzene, Carlsberg Res. Commun. 49 (1984) 591-596.

    23. [23]

      [13] C. Pérez-Balado, H. Sun, C. Griesinger, et al., Residual dipolar coupling enhanced NMR spectroscopy and chiroptics: a powerful combination for the complete elucidation of symmetrical small molecules, Chem. Eur. J. 17 (2011) 11983-11986.

    24. [24]

      [14] C.J. Barrow, P. Cai, J.K. Snyder, et al., WIN 64821, a new competitive antagonist to substance P, isolated from an Aspergillus species: structure determination and solution conformation, J. Org. Chem. 58 (1993) 6016-6021.

    25. [25]

      [15] C. Takahashi, K. Minoura, T. Yamada, et al., Potent cytotoxic metabolites from a Leptosphaeria species. Structure determination and conformational analysis, Tetrahedron 51 (1995) 3483-3498.

    26. [26]

      [16] L.L. Zaika, Spices and herbs: their antimicrobial activity and its determination, J. Food Safety 9 (1988) 97-118.

    27. [27]

      [17] T. Mosmann, Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, Immunol. Methods 65 (1983) 55-63.

  • 加载中
    1. [1]

      Jin WangXiaoyan PanJunyu ZhangQingqing ZhangYanchen LiWeiwei GuoJie Zhang . Active molecule-based theranostic agents for tumor vasculature normalization and antitumor efficacy. Chinese Chemical Letters, 2024, 35(8): 109187-. doi: 10.1016/j.cclet.2023.109187

    2. [2]

      Chuan LiYangyang HanYanan ZhaiKe LiXingzhong LiuZhuan ZhangCai JiaYongsheng Che . Phomaketals A and B, pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.. Chinese Chemical Letters, 2024, 35(7): 109019-. doi: 10.1016/j.cclet.2023.109019

    3. [3]

      Qianqian Zhong Yucui Hao Guotao Yu Lijuan Zhao Jingfu Wang Jian Liu Xiaohua Ren . Comprehensive Experimental Design for the Preparation of the Magnetic Adsorbent Based on Enteromorpha Prolifera and Its Utilization in the Purification of Heavy Metal Ions Wastewater. University Chemistry, 2024, 39(8): 184-190. doi: 10.3866/PKU.DXHX202312013

    4. [4]

      Jing JINZhuming GUOZhiyin XIAOXiujuan JIANGYi HEXiaoming LIU . Tuning the stability and cytotoxicity of fac-[Fe(CO)3I3]- anion by its counter ions: From aminiums to inorganic cations. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 991-1004. doi: 10.11862/CJIC.20230458

    5. [5]

      Shuige ZhaoPengcheng YanPeipei LiuHaishan LiuNing LiPeng FuWeiming Zhu . Pyridapeptides F‒I, cyclohexapeptides from marine sponge-derived Streptomyces sp. OUCMDZ-4539. Chinese Chemical Letters, 2024, 35(7): 108950-. doi: 10.1016/j.cclet.2023.108950

    6. [6]

      Jiatong LiLinlin ZhangPeng HuangChengjun Ge . Carbon bridge effects regulate TiO2–acrylate fluoroboron coatings for efficient marine antifouling. Chinese Chemical Letters, 2025, 36(2): 109970-. doi: 10.1016/j.cclet.2024.109970

    7. [7]

      Shule Liu . Application of SPC/E Water Model in Molecular Dynamics Teaching Experiments. University Chemistry, 2024, 39(4): 338-342. doi: 10.3866/PKU.DXHX202310029

    8. [8]

      Hong ZhangCui-Ping LiLi-Li WangZhuo-Da ZhouWen-Sen LiLing-Yi KongMing-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351

    9. [9]

      Jingfeng Lan Li Wu Guangnong Lu Liu Yang Xiaolong Li Xiangyang Xu Yongwen Shen E Yu . Application of 3E Method in the Negative List Management System in Teaching Laboratory. University Chemistry, 2024, 39(4): 54-61. doi: 10.3866/PKU.DXHX202310130

    10. [10]

      Guo-Ping YinYa-Juan LiLi ZhangLing-Gao ZengXue-Mei LiuChang-Hua Hu . Citrinsorbicillin A, a novel homotrimeric sorbicillinoid isolated by LC-MS-guided with cytotoxic activity from the fungus Trichoderma citrinoviride HT-9. Chinese Chemical Letters, 2024, 35(8): 109035-. doi: 10.1016/j.cclet.2023.109035

    11. [11]

      Aimin FuChunmei ChenQin LiNanjin DingJiaxin DongYu ChenMengsha WeiWeiguang SunHucheng ZhuYonghui Zhang . Niduenes A−F, six functionalized sesterterpenoids with a pentacyclic 5/5/5/5/6 skeleton from endophytic fungus Aspergillus nidulans. Chinese Chemical Letters, 2024, 35(9): 109100-. doi: 10.1016/j.cclet.2023.109100

    12. [12]

      Qi TanRun-Zhu FanWencong YangGe ZouTao ChenJianying WuBo WangSheng YinZhigang She . (+)/(−)-Mycosphatide A, a pair of highly oxidized polyketides with lipid-lowering activity from the mangrove endophytic fungus Mycosphaerella sp. SYSU-DZG01. Chinese Chemical Letters, 2024, 35(9): 109390-. doi: 10.1016/j.cclet.2023.109390

    13. [13]

      Yan Li Xinze Wang Xue Yao Shouyun Yu . Kinetic Resolution Enabled by Photoexcited Chiral Copper Complex-Mediated Alkene EZ Isomerization: A Comprehensive Chemistry Experiment for Undergraduate Students. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053

Metrics
  • PDF Downloads(0)
  • Abstract views(668)
  • HTML views(41)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return