Synthesis and Bioactivity of Luffarin I

The first synthesis of Luffarin I, sesterterpenolide isolated from sponge Luffariella geometrica, has been accomplished from commercially available sclareol. The key strategy involved in this synthesis is the diastereoselective reduction of an intermediate ketone. Luffarin I against human solid tumo...

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Main Authors: Aitor Urosa, Isidro S. Marcos, David Díez, Anna Lithgow, Gabriela B. Plata, José M. Padrón, Pilar Basabe
Format: Article
Language:English
Published: MDPI AG 2015-04-01
Series:Marine Drugs
Subjects:
Online Access:http://www.mdpi.com/1660-3397/13/4/2407
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author Aitor Urosa
Isidro S. Marcos
David Díez
Anna Lithgow
Gabriela B. Plata
José M. Padrón
Pilar Basabe
author_facet Aitor Urosa
Isidro S. Marcos
David Díez
Anna Lithgow
Gabriela B. Plata
José M. Padrón
Pilar Basabe
author_sort Aitor Urosa
collection DOAJ
description The first synthesis of Luffarin I, sesterterpenolide isolated from sponge Luffariella geometrica, has been accomplished from commercially available sclareol. The key strategy involved in this synthesis is the diastereoselective reduction of an intermediate ketone. Luffarin I against human solid tumor cell lines showed antiproliferative activities (GI50) in the range 12–17 μM.
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spelling doaj.art-3cda19a8e89242b5af5add8d57c678f42022-12-22T01:56:42ZengMDPI AGMarine Drugs1660-33972015-04-011342407242310.3390/md13042407md13042407Synthesis and Bioactivity of Luffarin IAitor Urosa0Isidro S. Marcos1David Díez2Anna Lithgow3Gabriela B. Plata4José M. Padrón5Pilar Basabe6Department of Organic Chemistry, Chemistry Faculty, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, SpainDepartment of Organic Chemistry, Chemistry Faculty, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, SpainDepartment of Organic Chemistry, Chemistry Faculty, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, SpainNuclear Magnetic Resonance Service, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, SpainBioLab, University Institute of Bio-Organic "Antonio González" (IUBO-AG), Centre of Biomedicine Research of Canarias (CIBICAN), University of La Laguna, C/Astrofísico Francisco Sánchez 2, 38206 La Laguna, SpainBioLab, University Institute of Bio-Organic "Antonio González" (IUBO-AG), Centre of Biomedicine Research of Canarias (CIBICAN), University of La Laguna, C/Astrofísico Francisco Sánchez 2, 38206 La Laguna, SpainDepartment of Organic Chemistry, Chemistry Faculty, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, SpainThe first synthesis of Luffarin I, sesterterpenolide isolated from sponge Luffariella geometrica, has been accomplished from commercially available sclareol. The key strategy involved in this synthesis is the diastereoselective reduction of an intermediate ketone. Luffarin I against human solid tumor cell lines showed antiproliferative activities (GI50) in the range 12–17 μM.http://www.mdpi.com/1660-3397/13/4/2407luffarin Isclareoldiastereoselective reductionspongessesterterpenolidemarine metabolites
spellingShingle Aitor Urosa
Isidro S. Marcos
David Díez
Anna Lithgow
Gabriela B. Plata
José M. Padrón
Pilar Basabe
Synthesis and Bioactivity of Luffarin I
Marine Drugs
luffarin I
sclareol
diastereoselective reduction
sponges
sesterterpenolide
marine metabolites
title Synthesis and Bioactivity of Luffarin I
title_full Synthesis and Bioactivity of Luffarin I
title_fullStr Synthesis and Bioactivity of Luffarin I
title_full_unstemmed Synthesis and Bioactivity of Luffarin I
title_short Synthesis and Bioactivity of Luffarin I
title_sort synthesis and bioactivity of luffarin i
topic luffarin I
sclareol
diastereoselective reduction
sponges
sesterterpenolide
marine metabolites
url http://www.mdpi.com/1660-3397/13/4/2407
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