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Author:

Fan, Guotao (Fan, Guotao.) | Li, Zelin (Li, Zelin.) | Shen, Shi (Shen, Shi.) | Zeng, Yi (Zeng, Yi.) | Yang, Yishu (Yang, Yishu.) | Xu, Minjuang (Xu, Minjuang.) | Bruhn, Torsten (Bruhn, Torsten.) | Bruhn, Heike (Bruhn, Heike.) | Morschhaeuser, Joachim (Morschhaeuser, Joachim.) | Bringmann, Gerhard (Bringmann, Gerhard.) | Lin, Wenhan (Lin, Wenhan.)

Indexed by:

Scopus SCIE

Abstract:

Fifteen new DOPA-derived pyrrole alkaloids, named baculiferins A-O (2-16), were isolated from the Chinese marine sponge Iotrochota baculifera, together with the known alkaloids purpurone (1) and ningalin A (17). Most of the new compounds contain one to three O-sulfate units. Their structures were determined by extensive spectroscopic analysis including (1)H and (13)C NMR (COSY, HMQC, HMBC) and ESIMS data. A possible pathway for the biosynthetic origin of the isolated alkaloids is proposed, in which DOPA is assumed to be a joint biogenetic precursor. Baculiferins C, E-H, and K-N (4, 6-9, 12-15) were found to be potent inhibitors against the HIV-1 IIIB virus in both, MT4 and MAGI cells. Additional bioassay revealed that baculiferins could dramatically bind to the HIV-1 target proteins Vif, APOBEC3G, and gp41, for which structure-activity relationships are discussed. (C) 2010 Elsevier Ltd. All rights reserved.

Keyword:

Baculiferins A-O Iotrochota baculifera HIV-1 IIIB virus Marine sponge HIV-1 target proteins

Author Community:

  • [ 1 ] [Bruhn, Torsten]Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
  • [ 2 ] [Bringmann, Gerhard]Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
  • [ 3 ] [Fan, Guotao]Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
  • [ 4 ] [Shen, Shi]Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
  • [ 5 ] [Xu, Minjuang]Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
  • [ 6 ] [Lin, Wenhan]Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
  • [ 7 ] [Li, Zelin]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100022, Peoples R China
  • [ 8 ] [Zeng, Yi]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100022, Peoples R China
  • [ 9 ] [Yang, Yishu]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100022, Peoples R China
  • [ 10 ] [Bruhn, Heike]Univ Wurzburg, Inst Mol Infect Biol, D-97080 Wurzburg, Germany
  • [ 11 ] [Morschhaeuser, Joachim]Univ Wurzburg, Inst Mol Infect Biol, D-97080 Wurzburg, Germany

Reprint Author's Address:

  • [Bringmann, Gerhard]Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

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Source :

BIOORGANIC & MEDICINAL CHEMISTRY

ISSN: 0968-0896

Year: 2010

Issue: 15

Volume: 18

Page: 5466-5474

3 . 5 0 0

JCR@2022

ESI Discipline: CHEMISTRY;

JCR Journal Grade:2

CAS Journal Grade:3

Cited Count:

WoS CC Cited Count: 52

SCOPUS Cited Count: 61

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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