Beta-lapachone: Natural occurrence, physicochemical properties, biological activities, toxicity and synthesis

• Published in: Phytochemistry (Oxford) Vol. 186; p. 112713
• Main Authors: Gomes, Camila Luiz, de Albuquerque Wanderley Sales, Victor, Gomes de Melo, Camila, Ferreira da Silva, Rosali Maria, Vicente Nishimura, Rodolfo Hideki, Rolim, Larissa Araújo, Rolim Neto, Pedro José
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-06-2021
• Subjects: Anti-Infective Agents; Bigoniaceae; Handroanthus impetiginosus; Humans; Melanoma; Naphthoquinones; Naphthoquinones - pharmacology; Red lapacho tree; Review; Wound Healing; β-Lapachone; Handroanthus impetiginosus; Review; β-Lapachone; Bigoniaceae; Naphthoquinones; Red lapacho tree
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2021.112713

β-Lapachone is an ortho-naphthoquinone originally isolated from the heartwood of Handroanthus impetiginosus and can be obtained through synthesis from lapachol, naphthoquinones, and other aromatic compounds. β-Lapachone is well known to inhibit topoisomerase I and to induce NAD(P)H: quinone oxidoreductase 1. Currently, phase II clinical trials are being conducted for the treatment of pancreatic cancer. In view of ever-increasing scientific interest in this naphthoquinone, herein, the authors present a review of the synthesis, physicochemical properties, biological activities, and toxicity of β-lapachone. This natural compound has shown activity against several types of malignant tumors, such as lung and pancreatic cancers and melanoma. Furthermore, this ortho-naphthoquinone has antifungal and antibacterial activities, underscoring its action against resistant microorganisms and providing anti-inflammatory, antiobesity, antioxidant, neuroprotective, nephroprotective, and wound-healing properties. β-Lapachone presents low toxicity, with no signs of toxicity against alveolar macrophages, dermal fibroblast cells, hepatocytes, or kidney cells.
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•The formation of ROS is the primary mechanism of β-lapachone against cancer cells.•The β-lapachone has shown antiviral, antiparasitic and antimicrobial effects.•Anti-inflammatory activities of β-lapachone may be due to synergistic mechanisms.•β-lapachone has potential therapeutic effects on obesity by the fat-browning effect.•β-Lapachone is able to suppress metastasis in vivo by several mechanisms.