3-Bromohomofascaplysin A, a fascaplysin analogue from a Fijian Didemnum sp ascidian

被引：13

作者：

Lu, Zhenyu ^{[1
]}

Ding, Yuanqing ^{[2
,3
]}

Li, Xing-Cong ^{[2
,3
]}

Djigbenou, Daignon R. ^{[4
,5
]}

Grimberg, Brian T. ^{[5
]}

Ferreira, Daneel ^{[2
,3
]}

Ireland, Chris M. ^{[1
]}

Van Wagoner, Ryan M. ^{[1
]}

机构：

[1] Univ Utah, Dept Med Chem, Salt Lake City, UT 84112 USA

[2] Univ Mississippi, Dept Pharmacognosy, University, MS 38677 USA

[3] Univ Mississippi, Sch Pharm, Natl Ctr Nat Prod Res, University, MS 38677 USA

[4] Case Western Reserve Univ, Div Infect Dis, Cleveland, OH 44106 USA

[5] Case Western Reserve Univ, Ctr Global Hlth & Dis, Cleveland, OH 44106 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2011年 / 19卷 / 22期

关键词：

Fascaplysin analogues; Ascidian; Antimalarial; Absolute configuration; Experimental and theoretically calculated ECD; CRYPTOLEPINE ANALOGS; FLOW-CYTOMETRY; MARINE; ALKALOIDS; ANTIMALARIAL; THIAZOLE; PEPTIDES; MALARIA; PIGMENT; CDK4;

D O I：

10.1016/j.bmc.2011.05.046

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new fascaplysin analogue, 3-bromohomofascaplysin A (1), along with two known analogues, homofascaplysin A (2) and fascaplysin (3), were isolated from a Fijian Didemnum sp. ascidian. The absolute configurations of 3-bromohomofascaplysin A (1) and homofascaplysin A (2) were determined via experimental and theoretically calculated ECD spectra. The differential activities of 1-3 against different blood-borne life stages of the malaria pathogen Plasmodium falciparum were assessed. Homofascaplysin A (2) displayed an IC(50) of 0.55 +/- 0.11 nM against ring stage parasites and 105 +/- 38 nM against all live parasites. Given the stronger resistance of ring stage parasites against most current antimalarials relative to the other blood stages, homofascaplysin A (2) represents a promising agent for treatment of drug resistant malaria. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6604 / 6607

页数：4

共 6 条

[1] A reinvestigation of the didemnaketals from the Palauan ascidian Didemnum sp
Pika, J
Faulkner, DJ
NATURAL PRODUCT LETTERS, 1995, 7 (04): : 291 - 296
[2] Purification, Characterization and Antibacterial Properties of Peptide from Marine Ascidian Didemnum sp.
Velusamy Arumugam
Manigandan Venkatesan
Karthik Ramachandran
Saravanan Ramachandran
Satheesh Kumar Palanisamy
Umamaheswari Sundaresan
International Journal of Peptide Research and Therapeutics, 2020, 26 : 201 - 208
[3] Purification, Characterization and Antibacterial Properties of Peptide from Marine Ascidian Didemnum sp.
Arumugam, Velusamy
Venkatesan, Manigandan
Ramachandran, Karthik
Ramachandran, Saravanan
Palanisamy, Satheesh Kumar
Sundaresan, Umamaheswari
INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2020, 26 (01) : 201 - 208
[4] Lepadins I-K, 3-O-(3′-Methylthio)acryloyloxy-decahydroquinoline Esters from a Bahamian Ascidian Didemnum sp Assignment of Absolute Stereostructures
Omarsdottir, Sesselja
Wang, Xiao
Liu, Hong-bing
Duggan, Brendan M.
Molinski, Tadeusz F.
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (22) : 13670 - 13677
[5] Synthesis of didemnolines A-D, N9-substituted β-carboline alkaloids from the marine ascidian Didemnum sp.
Schumacher, RW
Davidson, BS
TETRAHEDRON, 1999, 55 (04) : 935 - 942
[6] Isolation and biological activities of secondary metabolites from the sponges Monanchora aff. arbuscula, aplysina sp petromica ciocalyptoides and Topsentia ophiraphidites, from the ascidian Didemnum ligulum and from the octocoral Carijoa rusei
Kossuga, Miriam H.
de Lira, Simone P.
Nascimento, Andrea M.
Gambardella, Maria Teresa P.
Berlinck, Roberto G. S.
Torres, Yohandra R.
Nascimento, Gislene G. E.
Pimenta, Eli E.
Silva, Marcio
Thiemann, Otavio H.
Oliva, Glaucius
Tempone, Andre G.
Melhem, Marcia S. C.
de Souza, Ana O.
Galetti, Fabio C. S.
Silva, Celio L.
Cavalcanti, Bruno
Pessoa, Claudia O.
Moraes, Manoel O.
Hajdu, Eduardo
Peixinho, Solange
Rocha, Rosana M.
QUIMICA NOVA, 2007, 30 (05): : 1194 - 1202

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