Bioactive Coumarins and Xanthones From Calophyllum Genus and Analysis of Their Druglikeness and Toxicological Properties

Gómez-Verján, Juan Carlos; Hernández, Karla Rodríguez; Reyes‐Chilpa, Ricardo

doi:10.1016/b978-0-444-63930-1.00008-9

Cited by 9 publications

(9 citation statements)

References 79 publications

(50 reference statements)

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“…Whether similar route is present in other β-mangostin-producing species such as Calophyllum spp. (Gómez-Verjan et al, 2017;Zailan et al, 2021) still needs further investigation. These xanthones (α-, βand γ-mangostin) are known to possess antitumor, antioxidant, antidiabetic, antimicrobial, and anti-inflammatory properties, among others (Aizat et al, 2019;Marzaimi and Aizat, 2019).…”

Section: Biosynthetic Pathways Of Xanthone Derivatives In Plants Thro...mentioning

confidence: 99%

“…Although xanthone structures and chromatographic patterns are comparable to that of flavonoids, xanthones are present in only a few restricted species (Jensen and Schripsema, 2002;Vieira and Kijjoa, 2005). For example, xanthones can only be isolated from 20 families of higher plants of which most of them reside within Clusiaceae, Hypericaceae, and Gentianaceae families (Tovilovic-Kovacevic et al, 2020), and to some extent in Calophyllaceae family (Gómez-Verjan et al, 2017;Zailan et al, 2021). Prenylated xanthones can be mainly isolated from different Garcinia species (Clusiaceae).…”

Section: Introductionmentioning

confidence: 99%

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Xanthone Biosynthetic Pathway in Plants: A Review

2022

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Xanthones are secondary metabolites rich in structural diversity and possess a broad array of pharmacological properties, such as antitumor, antidiabetic, and anti-microbes. These aromatic compounds are found in higher plants, such as Clusiaceae, Hypericaceae, and Gentianaceae, yet their biosynthetic pathways have not been comprehensively updated especially within the last decade (up to 2021). In this review, plant xanthone biosynthesis is detailed to illuminate their intricacies and differences between species. The pathway initially involves the shikimate pathway, either through L-phenylalanine-dependent or -independent pathway, that later forms an intermediate benzophenone, 2,3′,4,6-tetrahydoxybenzophenone. This is followed by a regioselective intramolecular mediated oxidative coupling to form xanthone ring compounds, 1,3,5-trihydroxyxanthone (1,3,5-THX) or 1,3,7-THX, the core precursors for xanthones in most plants. Recent evidence has shed some lights onto the enzymes and reactions involved in this xanthone pathway. In particular, several biosynthetic enzymes have been characterized at both biochemical and molecular levels from various organisms including Hypericum spp., Centaurium erythraea and Garcinia mangostana. Proposed pathways for a plethora of other downstream xanthone derivatives including swertianolin and gambogic acid (derived from 1,3,5-THX) as well as gentisin, hyperixanthone A, α-mangostin, and mangiferin (derived from 1,3,7-THX) have also been thoroughly covered. This review reports one of the most complete xanthone pathways in plants. In the future, the information collected here will be a valuable resource for a more directed molecular works in xanthone-producing plants as well as in synthetic biology application.

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Section: Biosynthetic Pathways Of Xanthone Derivatives In Plants Thro...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Xanthone Biosynthetic Pathway in Plants: A Review

2022

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“…1,3,7-THX is proposed to be a precursor compound for prenylated xanthones, such as rubraxanthone from Garcinia [ 266 , 267 ] and Calophyllum species [ 9 , 268 , 269 ] and scortechinone B from Garcinia scortechinii King [ 270 , 271 ], as well as simple xanthones, such as 1,7-dihydroxy-3-methoxyxanthone (gentisin) and 1,3-dihydroxy-7-methoxyxanthone (isogentisin) from G. lutea [ 146 , 272 ]. In G. mangostana , γ-mangostin is proposed to be generated by prenylation of the 1,3,6,7-tetrahydroxyxanthones, and α-mangostin by the subsequent O-methylation [ 273 , 274 ].…”

Section: Xanthone Biosynthesismentioning

confidence: 99%

Xanthones: Biosynthesis and Trafficking in Plants, Fungi and Lichens

Badiali

Petruccelli

Brasili

et al. 2023

Plants

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Xanthones are a class of secondary metabolites produced by plant organisms. They are characterized by a wide structural variety and numerous biological activities that make them valuable metabolites for use in the pharmaceutical field. This review shows the current knowledge of the xanthone biosynthetic pathway with a focus on the precursors and the enzymes involved, as well as on the cellular and organ localization of xanthones in plants. Xanthone biosynthesis in plants involves the shikimate and the acetate pathways which originate in plastids and endoplasmic reticulum, respectively. The pathway continues following three alternative routes, two phenylalanine-dependent and one phenylalanine-independent. All three routes lead to the biosynthesis of 2,3′,4,6-tetrahydroxybenzophenone, which is the central intermediate. Unlike plants, the xanthone core in fungi and lichens is wholly derived from polyketide. Although organs and tissues synthesizing and accumulating xanthones are known in plants, no information is yet available on their subcellular and cellular localization in fungi and lichens. This review highlights the studies published to date on xanthone biosynthesis and trafficking in plant organisms, from which it emerges that the mechanisms underlying their synthesis need to be further investigated in order to exploit them for application purposes.

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“…This genus is an important source of bioactive natural products, including coumarins, xanthones, chromanones and triterpenes [ 3 , 4 ]. Xanthones and coumarins from Calophyllum species are known to possess cytotoxic, antiviral, antimicrobial, antiparasite, analgesic, anti-inflammatory and chemopreventive properties [ 5 , 6 ]. (+)-Calanolide A, a pyranocoumarin isolated from C. lanigerum , reached phase II of a clinical trial for its potent inhibitory activity of HIV-1 reverse transcriptase [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Metabolites from Calophyllum tacamahaca Willd.: Isolation and Detection through Feature-Based Molecular Networking

Gerometta¹,

Herbette

Garayev

et al. 2023

Metabolites

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Isocaloteysmannic acid (1), a new chromanone, was isolated from the leaf extract of the medicinal species Calophyllum tacamahaca Willd. along with 13 known metabolites belonging to the families of biflavonoids (2), xanthones (3–5, 10), coumarins (6–8) and triterpenes (9, 11–14). The structure of the new compound was characterized based on nuclear magnetic resonance (NMR), high-resolution electrospray mass spectrometry (HRESIMS), ultraviolet (UV) and infrared (IR) data. Its absolute configuration was assigned through electronic circular dichroism (ECD) measurements. Compound (1) showed a moderate cytotoxicity against HepG2 and HT29 cell lines, with IC50 values of 19.65 and 25.68 µg/mL, respectively, according to the Red Dye method. Compounds 7, 8 and 10–13 exhibited a potent cytotoxic activity, with IC50 values ranging from 2.44 to 15.38 µg/mL, against one or both cell lines. A feature-based molecular networking (FBMN) approach led to the detection of a large amount of xanthones in the leaves extract, and particularly analogues of the cytotoxic isolated xanthone pyranojacareubin (10).

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Bioactive Coumarins and Xanthones From Calophyllum Genus and Analysis of Their Druglikeness and Toxicological Properties

Cited by 9 publications

References 79 publications

Xanthone Biosynthetic Pathway in Plants: A Review

Xanthone Biosynthetic Pathway in Plants: A Review

Xanthones: Biosynthesis and Trafficking in Plants, Fungi and Lichens

Cytotoxic Metabolites from Calophyllum tacamahaca Willd.: Isolation and Detection through Feature-Based Molecular Networking

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