Jatrophane and rearranged jatrophane-type diterpenes: biogenesis, structure, isolation, biological activity and SARs (1984–2019)

Abstract

Diterpene compounds specially macrocyclic ones comprising jatrophane, lathyrane, terracinolide, ingenane, pepluane, paraliane, and segetane skeletons occurring in plants of the Euphorbiaceae family are of considerable interest in the context of natural product drug discovery programs. They possess diverse complex skeletons and a broad spectrum of therapeutically relevant biological activities including anti-inflammatory, anti-chikungunya virus, anti-HIV, cytotoxic, and multidrug resistance-reversing activities as well as curative effects on thrombotic diseases. Among macrocyclic diterpenes of Euphorbia, the discovery of jatrophane and modified jatrophane diterpenes with a wide range of structurally unique polyoxygenated polycyclic derivatives and as a new class of powerful inhibitors of P-glycoprotein has opened new frontiers for research studies on this genus. In this review, an attempt has been made to give in-depth coverage of the articles on the naturally occurring jatrophanes and rearranged jatrophane-type diterpenes isolated from species belonging to the Euphorbiaceae family published from 1984 to March 2019, with emphasis on the biogenesis, isolation methods, structure, biological activity, and structureactivity relationship.

Molecular Simulation-Based Investigation of Highly Potent Natural Products to Abrogate Formation of the nsp10–nsp16 Complex of SARS-CoV-2

“…Paraliane diterpene has shown anti-inflammatory and antiviral effects against human immunodeficiency virus (HIV) [ 61 ]. Experiments with MT-4 cells have shown that the antiviral activity of paraliane diterpene against HIV-1 replication arises through inhibition of the virus-induced cytopathicity and a moderate antiviral activity (EC50 = 14 mg/mL) [ 62 ]. In vivo, paraliane diterpene demonstrated comparable properties to dexamethasone [ 63 ].…”

New Insights on Euphorbia dendroides L. (Euphorbiaceae): Polyphenol Profile and Biological Properties of Hydroalcoholic Extracts from Aerial Parts

“…In particular, it is well known that the Euphorbia genus is a rich source of jatrophane and modified jatrophane diterpenes, a wide range of structurally unique macrocyclic and polyoxygenated derivatives, which opened new frontiers for research studies on this genus [ 21 ]. Many of them have been isolated from the latex and aerial parts of E. dendroides and, for this reason, the phytochemical research on this species has mainly focused in recent years on this class of compounds [ 12 , 13 , 15 , 19 ].…”

Bioactive Compounds from Euphorbia usambarica Pax. with HIV-1 Latency Reversal Activity

“…Compound 1 exhibited a 6/6/3-fused ring system with an α-methyl-α,β-unsaturated cyclopentanone moiety to construct a rare diterpenoid lactone, this skeleton was the second time discovered from nature [34]. The other compounds could be summarized in 4 types of diterpenoids, including jatrophanes (2-11), tiglianes (12)(13)(14)(15), abietanes (16)(17)(18)(19)(20)(21)(22)(23), and kaurane (24), alone with coumarinolignoid (25), lignan (26), coniferyl acetate (27), and benzenoids (28)(29)(30)(31). Especially, usambariphanes A (2) and B (3) displayed an unusual lactone ring constructed between C-17 and C-2 in the jatrophane structure, which is different from such lactone ring commonly constructed between C-17 and C-3 or between C-17 and C-5.…”

“…Moreover, sesquiterpenoids, triterpenoids, flavonoids, alkaloids, polyphenols, tannins, volatile compounds, and phytosterols have also been discovered in Euphorbia species, many of which are in active use as traditional medicines [ 8 , 9 , 10 ]. The pharmacological effects of Euphorbia species are related to anti-inflammatory [ 11 ], multidrug-resistance-reversing [ 12 , 13 ], antiviral [ 14 , 15 ], cytotoxic [ 16 , 17 ], anti-arrhythmic [ 18 ], antifungal [ 19 ], anti-thrombotic [ 20 ], antiallergic [ 21 ], and muscle relaxant [ 22 ] properties.…”