Abstract
Natural arylnaphthalene lactones are representative lignans that are found in various dietary and medicinal plants. Their unique structural features and significant pharmacological activity have attracted considerable attention from both synthetic and medicinal chemists. Owing to their unique structural features such as relative rigid tetracyclic skeleton, structural diversity of more than five substituents, and no chiral center, arylnaphthalene lactones are recognized as a valuable scaffold for drug discovery, in addition to their significant pharmacological activities. This review covers the structures and isolation of all naturally occurring arylnaphthalene lactone congeners reported. Based on the aryl substituents, they were categorized as Type I and Type II and further classified according to the oxidation state of the ring and glycosylation level. Special attention has been paid to natural arylnaphthalene lactones owing to their broad spectrum of biological activities such as cytotoxic, antiplatelet, antiviral, anti-HIV, antifungal, neuroprotective, and anti-inflammatory properties. All the products were reorganized based on their biological activities, and selected data are presented.
Highlights
Arylnaphthalene lignan lactones are naturally occurring fused tricyclic naphthalene lactones with aryl substituents
Natural arylnaphthalene lactones have a 70-phenyl naphthalene lactone skeleton in which the phenyl ring and naphthalene ring are polyhydroxylated, which are further transformed to methyl ethers or dioxolane
They can be classified into Type I and Type II arylnaphthalene lactones by the cis and trans relationship of lactone carbonyl and the aryl substituents
Summary
Arylnaphthalene lignan lactones are naturally occurring fused tricyclic naphthalene lactones with aryl substituents. In 1996, Chen et al determined the 50% inhibitory activity to the arachidonic acid (AA)-induced aggregation of rabbit platelets at 20 lg/mL from the EtOH extract of the whole plant of J. procumbens They isolated nine arylnaphthalide lignans, neojusticin A (105), justicidin B (1), justicidin A (26), taiwanin E methyl ether (32), neojusticin B (103), chinensinaphthol methyl ether (30), taiwanin E (20), chinensinaphthol (19), and diphyllin (18), from J. procumbens and evaluated these for their antiplatelet activity. Phyllamyricin C (12) showed the most significant antifungal activity with MIC and minimum fungicidal concentration values of 4.0 and 62.5 lg/ mL, respectively, and the seven lignans inhibited conidia germination of F. oxysporum in a concentration-dependent manner (Windayani et al 2014). The active compound diphyllin acetylapioside (43) was isolated and showed a significant inhibitory effect against TPA-induced inflammation in mice with a 50% inhibitory dose (ID50) value at 0.27 lMol/ear (Prieto et al 1996). They showed significant inhibition of IL-12 and TNF-a production with IC50 values ranging from 12.5 to 100 lM (Rao et al 2006)
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