Lapachol: An overview

Abstract

Lapachol is a naphthoquinone that was first isolated by E. Paterno from Tabebuia avellanedae (Bignoniaceae) in 1882. A wide spectrum of therapeutic activities have been attributed to lapachol or its derivatives viz., anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, bactericidal, fungicidal, insectifugal, pesticidal, protisticidal, respiradepressant, schistosomicidal, termiticidal, and viricidal. Originally isolated from species of the Bignoniaceae family, lapachol can also be found in other families such as Verbenaceae, Proteaceae, Leguminosae, Sapotaceae, Scrophulariaceae, and Malvaceae. The interesting and most usefull knowledge on lapachol, which is reviewed in this paper, can be used as a starting point in future research endeavors.

Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone

“…Because it has been considered that isoprenyl pyrophosphate couples with 2-hydroxy-1,4-naphthoquinone (lawsone, 1a)t of orm lapachol in Bignoniaceous plants, [16] we initially embarked on the synthesis of lapacholf rom lawsone. Because it has been considered that isoprenyl pyrophosphate couples with 2-hydroxy-1,4-naphthoquinone (lawsone, 1a)t of orm lapachol in Bignoniaceous plants, [16] we initially embarked on the synthesis of lapacholf rom lawsone.…”

“…In the preparation of a-lapachone, b-lapachone, and related compounds, lapachol was thought to be the best startingm aterial. Because it has been considered that isoprenyl pyrophosphate couples with 2-hydroxy-1,4-naphthoquinone (lawsone, 1a)t of orm lapachol in Bignoniaceous plants, [16] we initially embarked on the synthesis of lapacholf rom lawsone. Kazantzi et al reported the Pd(PPh 3 ) 4 -catalyzed alkylation of lawsone with 1-bromo-3-methyl-2-butene in acidic conditions at reflux; [17] however,t he yield waslessthan 45 %.…”

Antioxidant, Antibacterial and Antitumor Activity of Ethanolic Extract of the <i>Psidium guajava</i> Leaves

“…The LD 50 for leaf extract was 185.15 µg/ml and lapachol was 22.74 µg/ml. Lapachol is natural product with known anticancer properties, anti-inflammatory, analgesic, antibiotic, antimalarial, anti-trypanosome, antiulcer and regarded as relatively high toxicity [29]. The assay is considered a useful tool for preliminary assessment of toxicity [30].…”

Unraveling Natural Products’ Role in Osteoarthritis Management—An Overview

“…As in the cases of many other plant extracts exhibiting therapeutic characteristics, it must be noted that a number of compounds isolated from the water extract of the plant, inter alia, some cyclopentenyl esters, and the known naphthoquinone: lapachol, have been documented to have in vitro anti-inflammatory properties as well [72,73,75]. Notably, some of these derivatives effectively ameliorated NO, PGE 2 , TNF-α, and IL-1β production.…”