Semisynthesis of Justicidone and a 1,2-Quinone Lignan. Cytotoxic Activity of Some Natural and Synthetic Lignans

The dioxo-lignans of the arylnaphthalene-type named justicidone (2) and elenodione (3) were obtained from elenoside (1) through a short and efficient semisynthetic process. Justicidone (2), one of its synthetic precursors, 4-(benzo[d][1,3]dioxol-5-yl)-5,6,8-trimethoxy-3a,4-dihydronaphtho[2,3-c]furan...

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Published in:Natural product communications 2009-02, Vol.4 (2), p.235-238
Main Authors: Boluda, Carlos J., Trujillo, Juan M., Pérez, José A., López, Hermelo, Aragón, Zulma, Díaz, Raquel G.
Format: Article
Language:English
Subjects:
Acanthaceae - chemistry
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
Cell Line, Tumor
Humans
Lignans - chemical synthesis
Lignans - chemistry
Molecular Structure
Quinones - chemical synthesis
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container_title Natural product communications
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creator Boluda, Carlos J.
Trujillo, Juan M.
Pérez, José A.
López, Hermelo
Aragón, Zulma
Díaz, Raquel G.
description The dioxo-lignans of the arylnaphthalene-type named justicidone (2) and elenodione (3) were obtained from elenoside (1) through a short and efficient semisynthetic process. Justicidone (2), one of its synthetic precursors, 4-(benzo[d][1,3]dioxol-5-yl)-5,6,8-trimethoxy-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one (9), and the aglycone of elenoside (5) showed cytotoxic activity towards the HL-60 cell line (IC50 = 7.25 μM, 5.41 μM and 2.06 μM, respectively).
doi_str_mv 10.1177/1934578X0900400214
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subjects Acanthaceae - chemistry
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
Cell Line, Tumor
Humans
Lignans - chemical synthesis
Lignans - chemistry
Molecular Structure
Quinones - chemical synthesis
title Semisynthesis of Justicidone and a 1,2-Quinone Lignan. Cytotoxic Activity of Some Natural and Synthetic Lignans
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