Bioactive Xanthones from <i>Cratoxylum cochinchinense</i>

Raksat, Achara; Sripisut, Tawanun; Maneerat, Wisanu

doi:10.1177/1934578x1501001141

Cited by 6 publications

(13 citation statements)

References 28 publications

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“…The IR spectrum showed absorption bands due to a hydroxy group and a carbonyl group at ν max 3324 br and 1643 cm −1 , respectively. UV bands were observed at λ max 234, 268, 318, and 384 nm, similar to those of cochinchinone A (7), also isolated in the course of this study, suggesting a 1,3,7-trioxygenated xanthone chromophore [18]. The 1 H NMR (CDCl 3 ) spectrum of 1 showed three aromatic protons with ABC-type signals at δ H 7.37 (1H, d, J = 8.9 Hz, H-5), δ H 7.24 (1H, dd, J = 8.9, 3.1 Hz, H-6), and δ The UV spectrum of 3 exhibited characteristic absorption bands of a xanthone (λ max 202, 236, 264 sh, 308, 364 nm).…”

Section: Resultsmentioning

confidence: 73%

“…The extract of C. cochinchinense has a broad spectrum of biological activities [3,4], and the plant is a rich source of xanthones, anthraquinones, and other phenolic compounds [5,6]. Some isolated xanthones have shown antibacterial [7,8], cytotoxic [6,9], and antimalarial [6,10] activities. The most thoroughly studied xanthones are αmangostin and garcinone E, which have been isolated from mangosteen fruit (Garcinia mangostana L, Guttiferae) [11,12].…”

Section: Introductionmentioning

confidence: 99%

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Four New Xanthones from Cratoxylum cochinchinense and Their In Vitro Antiproliferative Effects

et al. 2017

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The study of the chemical constituents of branches and twigs of collected in Singapore led to the isolation and structural elucidation of four new xanthones, named cratoxanthone A (), B (), C (), and D (), together with six known xanthones (-) and one known dihydroanthracenone (). Eight xanthones (including and) and were tested for their antiproliferative activity in three human carcinoma cell lines (lung adenocarcinoma A549, colorectal carcinoma Colo205, and epidermoid carcinoma KB) and a human acute lymphoblastic leukemia B cell line (NALM-6), and the mitochondrial membrane potential was determined in KB cells. New xanthones and attenuated NALM-6 cell proliferation with IC values of 17.78 and 8.27 µM, respectively. Furthermore, KB cells treated with these compounds had significantly decreased mitochondrial membrane potentials. Notably, the proliferation of A549 cells was specifically inhibited by , but not the xanthones.

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Section: Resultsmentioning

confidence: 73%

Section: Introductionmentioning

confidence: 99%

Four New Xanthones from Cratoxylum cochinchinense and Their In Vitro Antiproliferative Effects

et al. 2017

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“…These compounds have been previously isolated from different organs of G. mangostana [ 36 , 37 , 38 ]. 9-hydroxycalabaxanthone 1 has been found in the Clusiaceae and Hypericaceae families and has been characterized by its anticancer, antioxidant, and ability to inhibit the PL and AG enzymes [ 34 , 39 , 40 ]. 8-deoxygartanin 2 has been reported in other species of the Clusiaceae family and has been found to have anticancer, anti-Alzheimer’s properties, and the ability to inhibit the PL and AG enzymes [ 34 , 39 , 40 ].…”

Section: Resultsmentioning

confidence: 99%

“…9-hydroxycalabaxanthone 1 has been found in the Clusiaceae and Hypericaceae families and has been characterized by its anticancer, antioxidant, and ability to inhibit the PL and AG enzymes [ 34 , 39 , 40 ]. 8-deoxygartanin 2 has been reported in other species of the Clusiaceae family and has been found to have anticancer, anti-Alzheimer’s properties, and the ability to inhibit the PL and AG enzymes [ 34 , 39 , 40 ]. Gartanin 3 has been reported to be found in other species of the Clusiaceae family and multiple studies have shown its anticancer and antitumor properties, and ability to inhibit enzymes such as PL and AA [ 34 , 41 , 42 ].…”

Section: Resultsmentioning

confidence: 99%

Multitarget Action of Xanthones from Garcinia mangostana against α-Amylase, α-Glucosidase and Pancreatic Lipase

et al. 2022

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Digestive enzymes such α-amylase (AA), α-glucosidase (AG) and pancreatic lipase (PL), play an important role in the metabolism of carbohydrates and lipids, being attractive therapeutic targets for the treatment of type 2 diabetes and obesity. Garcinia mangostana is an interesting species because there have been identified xanthones with the potential to inhibit these enzymes. In this study, the multitarget inhibitory potential of xanthones from G. mangostana against AA, AG and PL was assessed. The methodology included the isolation and identification of bioactive xanthones, the synthesis of some derivatives and a molecular docking study. The chemical study allowed the isolation of five xanthones (1–5). Six derivatives (6–11) were synthesized from the major compound, highlighting the proposal of a new solvent-free methodology with microwave irradiation for obtaining aromatic compounds with tetrahydropyran cycle. Compounds with multitarget activity correspond to 2, 4, 5, 6 and 9, highlighting 6 with IC50 values of 33.3 µM on AA, 69.2 µM on AG and 164.4 µM on PL. Enzymatic kinetics and molecular docking studies showed that the bioactive xanthones are mainly competitive inhibitors on AA, mixed inhibitors on AG and non-competitive inhibitors on PL. The molecular coupling study established that the presence of methoxy, hydroxyl and carbonyl groups are important in the activity and interaction of polyfunctional xanthones, highlighting their importance depending on the mode of inhibition.

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“…By comparison with those data from the literatures, the known analogues were identified as cochinchinoxanthone ( 2 ) [21], 1,4,7-trihydroxy-8-methoxyxanthone ( 3 ) [22], gentisein ( 4 ) [23], 1,6-dihydroxy-2,5,8-trimethoxyxanthone ( 5 ) [23], 1,7-dihydroxyxanthone ( 6 ) [24], 1,7-dihydroxy-4-methoxyxanthone ( 7 ) [25], 1,7-dihydroxy-3,6-dimethoxyxanthone ( 8 ) [26], 1,7-dihydroxy-8-methoxyxanthone ( 9 ) [27], 1,5,6-trihydroxy-7-methoxyxanthone ( 10 ) [28], 1,4,7-trihydroxyxanthone ( 11 ) [29], 1,5,6-trihydroxy-3,7-dimethoxyxanthone ( 12 ) [30], 1,3,5,6-tetrahydroxyxanthone ( 13 ) [31], 1,3,6,7-tetrahydroxyxanthone ( 14 ) [32], 1,3,6-trihydroxy-7-methoxyxanthone ( 15 ) [29], cratoxanthone C ( 16 ) [33], 1,2,4-trimethoxy-3,8-dimethoxyxanthone ( 17 ) [34], 1,3,7-trihydroxy-2-(3-methylbut-2-enyl)-xanthone ( 18 ) [35], dulcisxanthone B ( 19 ) [20], cudratricusxanthone E ( 20 ) [36], γ-mangostin ( 21 ) [37], 1,3,7-trihydroxy-2,4-diisoprenylxanthone ( 22 ) [38], cochinchinone A ( 23 ) [33], cochinchinone B ( 24 ) [33], pruniflorone Q ( 25 ) [39], 1,3,5-trihydroxy-6′,6′-dimethyl-2 H -pyrano(2′,3:6,7)xanthone ( 26 ) [30], pruniflorone N ( 27 ) [40], xanthone V 1 ( 28 ) [41], osajaxanthone ( 29 ) [42], cochinchinone I ( 30 ) [43], 1,7-dihydroxy-4-(3,7-dimethylocta-2,6-dienyl)-5′-(1-hydroxy-1-methylethyl)-4′,5′-dihydrofuro[2′,3′:3,2]-xanthone ( 31 ) [44].…”

Section: Resultsmentioning

confidence: 99%

A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense

et al. 2019

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Background The simple and caged xanthones from Clusiaceae showed significant antineoplastic activity. This study aims to identify structural diverse xanthones and search for novel antitumor natural products from this family plants. Methods The structures of new compounds 1a and 1b were elucidated mainly through comprehensive NMR and MS spectroscopic data, and their absolute configurations were determined by the comparison of the experimental and calculated electronic circular dichroism. Results A pair of new xanthone enantiomers, (+)- and (−)-cracochinxanthone A ( 1a and 1b ), along with thirty known analogues ( 2 – 31 ), were isolated from extracts of the stems and leaves of C. cochinchinense. Preliminary biological assay of some isolates against HL-60, PC-3, and MDA-MB-231 cancer cell lines. Conclusion Some isolated xanthones exhibited high sensitivity against three human malignant cell lines and the structure–activity relationship study showed that the prenyl and geranyl units may play an important role in antitumor activity. Electronic supplementary material The online version of this article (10.1186/s13020-019-0235-z) contains supplementary material, which is available to authorized users.

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Bioactive Xanthones from Cratoxylum cochinchinense

Cited by 6 publications

References 28 publications

Four New Xanthones from Cratoxylum cochinchinense and Their In Vitro Antiproliferative Effects

Four New Xanthones from Cratoxylum cochinchinense and Their In Vitro Antiproliferative Effects

Multitarget Action of Xanthones from Garcinia mangostana against α-Amylase, α-Glucosidase and Pancreatic Lipase

A pair of new enantiomers of xanthones from the stems and leaves of Cratoxylum cochinchinense

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