Auraptene and umbelliprenin: a review on their latest literature acquisitions

Abstract

Auraptene and umbelliprenin are among the most abundant naturally occurring prenyloxy umbelliferone derivatives. Both have been mainly isolated from plants belonging to numerous genera of the Rutaceae (in particular auraptene in Citrus spp.) and Apiaceae (in particular umbelliprenin in Ferula spp.) families, comprising different and widely used medicinal plants and in general plants having beneficial effects to human welfare as well as edible fruits and vegetables. Although known for quite a long time (nearly a century for auraptene and 50 years for umbelliprenin), only in the last two decades the two title natural compounds were revealed to possess valuable and promising pharmacological properties as dietary feeding active cancer chemopreventive, antibacterial, anti-protozoal, anti-fungal, anti-inflammatory, neuroprotective, and anti-oxidant agents among the activities best detailed in the recent literature. The aim of this comprehensive review is to outline in detail the effects described in the very last years for auraptene and umbelliprenin and what has been reported about the mechanisms of action underlying the observed pharmacological activities of these oxyprenylated secondary metabolites. In view of the herein described data suggestions on how to address the future research about both natural products in the best ways according to Authors will be also provided.

Photoswitchable Isoprenoid Lipids Enable Optical Control of Peptide Lipidation

“…Many of these exhibit linear isoprenoid chains that could be functionalized with an azobenzene in an analogous fashion to yield optical control of their function. Linear isoprenoid lipids with interesting bioactivity include the tocotrienols (Vitamin E), cannabinoids (cannabigerol or cannabigerolic acid), the moenomycin antibiotics, or other natural products such as auraptene and umbelliprenin . Isoprenoid lipids have further been used in the design of synthetic pharmacophores, such as the Ras inhibitor salirasib. , Future efforts will address the development of photoswitchable isoprenoids based on these and other bioactive metabolites to assess how modular the described approach is for the class of isoprenoid lipids.…”

Antioxidant, Antimicrobial Activities and Characterization of Polyphenol-Enriched Extract of Egyptian Celery (Apium graveolens L., Apiaceae) Aerial Parts via UPLC/ESI/TOF-MS

“…Auraptene (peak 75 at t R = 16.72 min. at m / z 297.15207 Da [C 19 H 21 O 3 ] − ) is a bioactive monoterpene coumarin ether which has been reported in celery to possess strong antioxidant and hepatoprotective activities [ 19 ] ( Figure S17 ). A unique terpenoid ester, tschimganin, reported previously in family Apiaceae [ 20 ], was identified in (TAE) (peak 78 at t R = 17.79 min.…”

Semisynthesis of Selenoauraptene

“…From a medicinal chemistry point of view, several structural analogues have been extracted from natural sources and/or synthesized. The modifications of the basic skeleton of auraptene to yield similarly biologically active compounds include substitution of the α,β-unsaturated lactone ring with α,β-unsaturated carboxylic acid [ 6 ] and α,β-unsaturated aldehyde moieties [ 7 ], introduction of methoxy groups, halogens, and additional terpenyl chains as substituents of the aromatic ring [ 8 , 9 , 10 ], functionalization of the geranyloxy side chain [ 11 , 12 ], and finally introduction of different substituents in the lactone portion [ 13 , 14 ]. The plethora of literature data related to this suggests that the synthesis and investigation of the pharmacological properties of isosters and structural analogues of auraptene is a field of current and active research with many potential outcomes and practical uses in the near future.…”