摘要：

This review analyzes the more recent publications concerning the distribution, chemistry, and bioactivities of naphthoquinones (NQs) in higher plants. These highly reactive molecules have a diverse distribution in nature being isolated from bacteria, algae, fungi, lichens, insects, and higher plants, where they mostly occur in Eudicots. Over 200 species reported to produce NQs are listed according to orders and families. Out of 65 orders, only 16 report their occurrence, suggesting that the phylogenetically more advanced orders (Caryophyllales, Ericales, and Lamiales) have a higher percentage of NQ-producing families. Certain classes of NQs appear confined to certain orders. Chemically, the NQs found range from simple monomeric 1, 4- and 1, 2-NQ isomers to dimers, trimers, and tetramers, as well as furano, pyrano, and prenylated derivatives. The major bioactivities are summarized, including cytotoxicity and antitumor (a-dunnione, plumbagin, and shikonin), antibacterial (diospyrin), anti-inflammatory (iso-eleutherin), antiparasitic (sterekunthal A), antifungal (droserone). Some NQs are considered to be phytoalexins (e.g., O-hibiscanone induced by fungal infection of Hibiscus cannabinus with Verticillium dahliae ). Many of these activities are associated with their inhibition of electron transport, uncoupling of oxidative phosphorylation, and their intercalation with DNA. Many NQ-containing plants are of importance to humans, commercially as dyes (lawsone, shikonin) or as medicines in systems of Traditional Medicine (e.g., Lapacho, a herbal medicine used by South and Central American indigenous peoples to treat ailments including infection, fever, and stomach complaints). The review underlines the importance of NQs in taxonomy, chemistry, and their bioactive potential as novel biocides and chemotherapeutic agents.

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