Synthesis and bioactivity of Luffarin I

Aitor Urosa; Isidro S Marcos; David Díez; Anna Lithgow; Gabriela B Plata; José M Padrón; Pilar Basabe

doi:10.3390/md13042407

Synthesis and bioactivity of Luffarin I

Mar Drugs. 2015 Apr 20;13(4):2407-23. doi: 10.3390/md13042407.

Authors

Aitor Urosa¹, Isidro S Marcos², David Díez³, Anna Lithgow⁴, Gabriela B Plata⁵, José M Padrón⁶, Pilar Basabe⁷

Affiliations

¹ Department of Organic Chemistry, Chemistry Faculty, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. aitor_ug@usal.es.
² Department of Organic Chemistry, Chemistry Faculty, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. ismarcos@usal.es.
³ Department of Organic Chemistry, Chemistry Faculty, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. ddm@usal.es.
⁴ Nuclear Magnetic Resonance Service, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. tille1962@usal.es.
⁵ BioLab, 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, Spain. g.b.plata@gmail.com.
⁶ BioLab, 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, Spain. jmpadron@ull.es.
⁷ Department of Organic Chemistry, Chemistry Faculty, University of Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain. pbb@usal.es.

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemical synthesis
4-Butyrolactone / chemistry
4-Butyrolactone / pharmacology
Animals
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology
Australia
Cell Line, Tumor
Cell Proliferation / drug effects
Diterpenes / chemistry
Furans / chemical synthesis*
Furans / chemistry
Furans / pharmacology
Humans
Indicators and Reagents / chemistry
Molecular Conformation
Molecular Structure
Neoplasms / drug therapy*
Neoplasms / pathology
Osmolar Concentration
Pacific Ocean
Porifera / chemistry
Sesterterpenes / chemical synthesis*
Sesterterpenes / chemistry
Sesterterpenes / pharmacology
Stereoisomerism

Substances

Antineoplastic Agents
Diterpenes
Furans
Indicators and Reagents
Sesterterpenes
luffarin I
sclareol
4-Butyrolactone