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Plants belonging to Artemisia spp. are known to biosynthesize a wide panel of 3,3-dimethylallyl- and sesquiterpenyl- substituted coumarins. In this short communication we applied a novel extraction methodology based on the use of subcritical butane under a counter-current mode to further characterize the presence of selected biologically active oxyprenylated phenylpropanoids, namely coumarins and ferulic acid derivatives, in extracts deriving from aerial parts of Artemisia vulgaris L. (commonly known as "common mugwort") (Asteraceae). In the mean time, we assessed the efficiency of the above mentioned extractive methodology with other routes like maceration and ultrasounds and microwaves-based methods using absolute EtOH as the solvents. UHPLC analysis coupled to UV/Vis detection revealed that, among the 5 pure chemical standard assayed, only umbelliprenin (7-farnesyloxycoumarin) was recorded, while boropinic acid, 4'-geranyloxyferulic acid, 7-isopentenyloxycoumarin, and auraptene were not detected. The best extractive yield (0.18 %) was obtained after extaction with subcritical butane. The presence of umbelliprenin in Artemisia plant species has been reported herein for the first time. This coumarin may represent the biosynthetic precursors of sesquiterpenyloxycoumarins with more complex structures typically found in this genus., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier B.V. All rights reserved.)

Spinach leaves, goji berries and quinoa seeds are claimed to have a great nutraceutical potential due to their high content of compounds providing benefits for human health, such as amino acids, polyunsaturated fatty acids, carotenoids, betaine, vitamins, fibre, minerals and polyphenols. Samples of these plants were extracted with different solvent mixtures (e.g. EtOH, H 2 O/EtOH 3:7 and H 2 O/EtOH 7:3) and extractions were accomplished using a microwave apparatus. Subsequent UHPLC analysis and photodiode array detection were employed for the quantification of biologically active compounds like 7-isopentenyloxycoumarin, auraptene, umbelliprenin, boropinic acid and 4'-geranyloxyferulic acid. EtOH was found to be the best solvent in terms of extractive yields and the above-mentioned phytochemicals were recorded in the concentration range 2.01-49.22 µg/g dry extract. The findings depicted herein revealed that spinach, goji and quinoa are good sources of oxyprenylated umbelliferone and ferulic acid derivatives., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

Oxyprenylated secondary metabolites (e.g. phenylpropanoids and polyketides) represent a rare class of natural compounds. Over the past two decades, this group of phytochemicals has become a topic of intense research activity by several teams worldwide due to their in vitro and in vivo pharmacological activities, and to their great therapeutic and nutraceutical potential for the chemoprevention of acute and chronic diseases affecting humans. Such investigations have provided evidence that oxyprenylated secondary metabolites are able to interact with several biological targets at different levels accounting for their observed anticarcinogenic, anti-inflammatory, neuroprotective, immunomodulatory, antihypertensive, and metabolic effects. The aim of the present contribution is to provide a detailed survey of the so far reported data on the capacities of selected oxyprenylated phenylpropanoids and polyketides to trigger receptors, enzymes, and other types of cellular factors for which they exhibit a high degree of affinity and therefore evoke specific responses. With respect to the rather small amounts of these compounds available from natural sources, their chemical synthesis is also highlighted.

An analytical strategy based on different extraction methodologies and HPLC with spectrophotometric (UV-vis) detection has been developed to investigate the presence of and to quantitate biologically active selected unprenylated and O-prenylated phenylpropanoids, namely umbelliferone, 4'-geranyloxyferulic acid, 7-isopentenyloxycoumarin, auraptene, and umbelliprenin in dill (Anethum graveolens L.), anise (Pimpinella anisum L.), and wild celery (Angelica archangelica L.). Absolute ethanol or 7:3 water/ethanol mixtures were seen to be the most powerful extraction solvents to perform "classic" maceration or ultrasound-assisted one in terms of yields in secondary metabolites. For anethum and anise, umbelliprenine was found to be the most abundant prenyloxy secondary metabolite, while in wild celery 4'-geranyloxyferulic acid recorded the highest concentration. Our experimental approach demonstrated to be efficient for the simultaneous identification and quantitation of the above mentioned prenyloxyphenylpropanoids in the title plant species, that is reported herein for the first time in the literature., (Copyright © 2016 Elsevier B.V. All rights reserved.)

The genus Skimmia is a rich source of interesting secondary metabolites, including 20 alkaloids derived from anthranilic acid, 45 coumarins, 21 limonoids, four cholestane derivatives, six pentacyclic triterpenes, six flavonoids, and two unusual fatty acid derivatives. Skimmia is employed in folk medicine e.g. against fever, inflammations, and rheumatism. Skimmia extracts, Skimmia essential oils and pure compounds isolated from Skimmia extracts have been experimentally shown to have various bioactivities such as antioxidant, anti-inflammatory, antimicrobial, and insecticidal. In this review we discuss the exact structures of compounds isolated from members of the genus Skimmia, bioactivities of Skimmia extracts and pure compounds derived from them, and systematic implications of the patterns of occurrence of these compounds. Moreover, research gaps and interesting avenues for future research are discussed briefly., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

4'-Geranyloxyferulic (GOFA) and boropinic acid have been discovered during the last decade as interesting phytochemicals having valuable pharmacological effects as cancer chemopreventive, anti-inflammatory, neuroprotective, and anti-Helicobacter pylori agents. A reverse-phase HPLC-UV/Vis method for the separation and quantification of the title oxyprenylated ferulic acid derivatives in extracts obtained from peels of nine edible Citrus and Fortunella fruits was successfully applied. Concentration values showed a great variation between the different species, being orange (C. sinensis) the fruit richest in GOFA (0.141 ± 0.011 mg/g of exocarp fresh weight) and kumquat (Fortunella japonica) the one in which boropinic acid was recorded as the most abundant phytochemical (0.206 ± 0.002 mg/g of exocarp fresh weight). Both secondary metabolites were not detected only in three species. The set-up methodology showed limits of quantification (LOQ) values, that were able to selectively quantify both GOFA and boropinic acid. Results described herein depict a potential chemopreventive dietary feeding role for the Rutaceae spp. under investigation.

The genus Acronychia (Rutaceae) comprise 44 species, most of which are represented by shrubs and small trees, distributed in a wide geographical area of South-Eastern Asia comprising China, India, Malaysia, Indonesia, Australia, and the islands of the western Pacific Ocean. Most of the species of the genus Acronychia have been used for centuries as natural remedies in the ethnomedical traditions of indigenous populations as anti-microbial, anti-fungal, anti-spasmodic, stomachic, anti-pyretic, and anti-haemorragic agent. Moreover fruits and aerial parts are used as food in salads and condiments, while the essential oil obtained from flowers and leaves has been employed in cosmetics production. Phytochemicals isolated from Acronychia spp. include acetophenones, quinoline and acridone alkaloids, flavonoids, cinnamic acids, lignans, coumarins, steroids, and triterpenes. The reported biological activities of the above mentioned natural compounds refer to anti-plasmodial, anti-cancer, anti-oxidant, anti-inflammatory, anti-fungal, and neuroprotective effects. The aim of this review is to examine in detail from a phytochemical and pharmacologically point of view what is reported in the current literature about the properties of phytopreparations or individual active principles obtained from plants belonging to the Acronychia genus., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

Several natural compounds containing an anthraquinone core linked to a prenyloxy chain have been reported in the literature in recent years. The discovery in the plant kingdom of such secondary metabolites is a novel acquisition in the phytochemistry research field and in many cases led to a re-consideration of the secondary metabolite pool of well known anthraquinone-containing plants. In this review article we will focus on the phytochemistry and pharmacognosy of prenyloxyanthraquinones putting in evidence the natural sources and their biological properties as anti-microbial and anticancer agents.