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

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

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 oxidored...

Full description

Saved in:
Bibliographic Details
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
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. [Display omitted] •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.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-3
content type line 23
ObjectType-Review-1
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2021.112713