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

Camila Luiz Gomes, Victor de Albuquerque Wanderley Sales, Camila Gomes de Melo, Rosali Maria Ferreira da Silva, Rodolfo Hideki Vicente Nishimura, Larissa Araújo Rolim, Pedro José Rolim Neto

Journal: Phytochemistry 2021;186():112713

PMID: 33667813

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Abstract

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.

Address: Laboratório de Tecnologia Dos Medicamentos, Department of Pharmaceutical Sciences, Federal University of Pernambuco, 50670-901, Av. Professor Artur de Sá, S/n - Cidade Universitária, Recife, PE, Brazil.; Central de Análise de Fármacos, Medicamentos e Alimentos (CAFMA), Federal University of Vale Do São Francisco, 56304-205, Av. José de Sá Maniçoba, S/n - Centro, Petrolina, PE, Brazil.; Laboratório de Tecnologia Dos Medicamentos, Department of Pharmaceutical Sciences, Federal University of Pernambuco, 50670-901, Av. Professor Artur de Sá, S/n - Cidade Universitária, Recife, PE, Brazil. Electronic address: [email protected].

DOI: 10.1016/j.phytochem.2021.112713

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MeSH Terms: Anti-Infective Agents, Humans, Melanoma, Naphthoquinones, Wound Healing