Biomolecular Targets of Oxyprenylated Phenylpropanoids and Polyketides

Fiorito, Serena; Epifano, Francesco; Preziuso, Francesca; Taddeo, Vito Alessandro; Genovese, Salvatore

doi:10.1007/978-3-030-01099-7_2

Cited by 11 publications

(9 citation statements)

References 202 publications

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“…www.nature.com/scientificreports/ Emerging literature has indicated that lipids and lipid-like molecules have less anti-inflammatory properties, higher antioxidant effects, immunomodulatory effect, and decrease the risk of cholestasis, and improve clinical outcomes of certain subgroups of patients 35 . Research has shown that phenylpropanoid and polyketides possess anticarcinogenic, anti-inflammatory, neuroprotective, immunomodulatory, antihypertensive, and metabolic effects 36 . Benzenoids have the effect on anti-inflammatory 37 .…”

Section: Screening and Classification Of The Differential Metabolitesmentioning

confidence: 99%

UPLC/MS-based untargeted metabolomics reveals the changes of metabolites profile of Salvia miltiorrhiza bunge during Sweating processing

Cao

Liu

Jiang

et al. 2020

Sci Rep

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Salvia miltiorrhiza has numerous compounds with extensive clinical application. “Sweating”, a processing method of Traditional Chinese Medicine (TCM), results in great changes in pharmacology and pharmacodynamics. Previously, chromatogram of 10 characteristic metabolites in S. miltiorrhiza showed a significant difference after “Sweating”. Due to the complexity of TCM, changes in metabolites should be investigated metabolome-wide after “Sweating”. An untargeted UPLC/MS-based metabolomics was performed to discover metabolites profile variation of S. miltiorrhiza after “Sweating”. Multivariate analysis was conducted to screen differential metabolites. Analysis indicated distinct differences between sweated and non-sweated samples. 10,108 substance peaks had been detected altogether, and 4759 metabolites had been identified from negative and positive ion model. 287 differential metabolites were screened including 112 up-regulated and 175 down-regulated and they belong to lipids and lipid-like molecules, and phenylpropanoid and polyketides. KEGG analysis showed the pathway of linoleic acid metabolism, and glyoxylate and dicarboxylate metabolism were mainly enriched. 31 and 49 identified metabolites were exclusively detected in SSM and NSSM, respectively, which mainly belong to carboxylic acids and derivatives, polyketides and fatty acyls. By mapping tanshinones and salvianolic acids to 4759 identified metabolites library, 23 characteristic metabolites had been identified, among which 11 metabolites changed most. We conclude that “Sweating’’ has significant effect on metabolites content and composition of S. miltiorrhiza.

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Section: Screening and Classification Of The Differential Metabolitesmentioning

confidence: 99%

UPLC/MS-based untargeted metabolomics reveals the changes of metabolites profile of Salvia miltiorrhiza bunge during Sweating processing

Cao

Liu

Jiang

et al. 2020

Sci Rep

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“…Auraptene is the most abundant geranyloxycoumarin found in nature, and its plant sources and pharmacological properties were reviewed for the first time in 2011, and subsequently in 2020 [ 4 , 5 ]. Its presence has been documented in several edible fruits and vegetables, like Citrus spp.…”

Section: Introductionmentioning

confidence: 99%

Semisynthesis of Selenoauraptene

et al. 2021

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Selenium-containing compounds are gaining more and more interest due to their valuable and promising pharmacological properties, mainly as anticancer and antioxidant agents. Ebselen, the up to now only approved drugs, is well known to possess very good glutathione peroxidase mimicking effects. To date, the most of efforts have been directed to build pure synthetic Se containing molecules, while less attention have been devoted to Se-based semisynthetic products resembling natural compounds like terpenes, polyphenols, and alkaloids. The aim of this short communication is to report the synthesis of the first example of a Se-phenylpropanoids, namely selenoauraptene, containing a selenogeranyl side chain in position 7 of the umbelliferone core. The key step was the Newman-Kwart rearrangement to obtain a selenocarbamate in which the Se atom was directly attached to umbelliferone (replacing its 7-OH function) followed by hydrolysis to get diumbelliferyl diselenide, which was finally easily converted to the desired Se-geranyl derivative in quite a good overall yield (28.5%). The synthesized adduct displayed a greater antioxidant and a radical scavenger in vitro activity than parent auraptene. The procedure we describe herein, to the best of our knowledge for the first time in the literature, represents an easy-to-handle method for the synthesis of a wide array of seleno analogues of naturally occurring biologically active oxyprenylated secondary metabolites.

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“…The first group have been subject of more attention for what concerns the phytochemical and pharmacological properties. What was put in evidence for oxyprenylated phenylpropanoids is mainly their efficacy to act as chemopreventive agents of acute and chronic syndromes affecting humans like cancer, inflammation, stroke, neurological disorders, and several others (Fiorito et al 2019a). The most part of review and research articles appeared in the literature in recent years focused on two oxyprenylated coumarins, both derivatives of the widespread umbelliferone (1).…”

Section: Introductionmentioning

confidence: 99%

Auraptene and umbelliprenin: a review on their latest literature acquisitions

et al. 2020

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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.

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Biomolecular Targets of Oxyprenylated Phenylpropanoids and Polyketides

Cited by 11 publications

References 202 publications

UPLC/MS-based untargeted metabolomics reveals the changes of metabolites profile of Salvia miltiorrhiza bunge during Sweating processing

UPLC/MS-based untargeted metabolomics reveals the changes of metabolites profile of Salvia miltiorrhiza bunge during Sweating processing

Semisynthesis of Selenoauraptene

Auraptene and umbelliprenin: a review on their latest literature acquisitions

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