A new chromanone acid from the stem bark of Calophyllum teysmannii

Abstract

A new chromanone acid, namely caloteysmannic acid (1), along with three known compounds, calolongic acid (2), isocalolongic acid (3) and stigmasterol (4) were isolated from the stem bark of Calophyllum teysmannii. All these compounds were evaluated for their cytotoxic and antioxidant activities in the MTT and DPPH assays, respectively. The structure of compound 1 was determined by means of spectroscopic methods including 1D and 2D NMR experiments as well as HR-EIMS spectrometry. The stereochemical assignment of compound 1 was done based on the NMR results and X-ray crystallographic analysis. The preliminary assay results revealed that all the test compounds displayed potent inhibitory activity against HeLa cancer cell line, in particular with compound 1 which exhibited the highest cytotoxic activity comparable to the positive control used, cisplatin. However, no significant antioxidant activity was observed for all the test compounds in the DPPH radical scavenging capacity assay.

In vitro cytotoxic activity of isolated compounds from Malaysian Calophyllum species

“…1) were established by spectroscopic methods and comparison with literature data (Plattner et al, 1974;Guilet et al, 2001;Lin et al, 2006;Bayma et al, 1998;Dharmaratne et al, 2009;Sousa et al, 2012;Lim et al, 2015). Isolation of isodispar B (1) was previously reported from C. dispar (Guilet et al, 2001).…”

“…Friedelin (3), stigmasterol (7), and friedelinol (11) were ubiquitous compounds commonly found in higher plants, which have been extensively studied to show antibacterial (Viswanathan et al, 2012), antifungal (Jain et al, 2001), and cytotoxic (Csupor-Löffler et al, 2011;Shen et al, 2012) activities. Tesymannic acid (4) isolated from C. teysmannii was found to exhibit potent inhibitory activity against HeLa cancer cells (IC 50 value of 7.3 µM) (Lim et al, 2015). Calolongic acid (5) and isocalolongic acid (6) previously isolated from C. caledonicum were both reported to exert strong antifungal activities against Aspergillus fumigatus, showing MIC 80 values of 4 and 2 µg/mL, respectively (Hay et al, 2004).…”

New chromanone derivatives containing thiazoles: Synthesis and antitumor activity evaluation on A549 lung cancer cell line

“…Chromane (3,4‐dihydro‐2 H ‐1‐benzopyran; 3,4‐dihydro‐2 H ‐chromene) ring is medicinally important structure together with its very similar ring analogs 4 H ‐chromene (benzopyran) and 2 H ‐chromene. Chroman‐4‐one and its analogs chromone and coumarine derivatives besides flavanone (2‐phenyl‐2,3‐dihydrochromen‐4‐one), flavone (2‐phenyl‐4 H ‐chromen‐4‐one), and homoisoflavonoids ((3‐benzylidene‐4)‐chromanones) derivatives are widely studied derivatives (Figure 1) (Alizadeh et al, 2008; Demirayak et al, 2017; Kaviarasan et al, 2020; Lim et al, 2015; Masesane & Desta, 2012; Patil & Sawant, 2015).…”

5,9,11-Trihydroxy-2,2-dimethyl-3-(2-methylbut-3-en-2-yl)pyrano[2,3-a]xanthen-12(2H)-one from the Stem Bark of Calophyllum tetrapterum Miq.

“…This genus is well known to be a rich source of bioactive xanthones [1][2][3][4], coumarins [5][6][7], chromanone acids [8][9][10][11], and flavonoids [12]. Some these were reported to exhibit of biological activities including anti-HIV, anticancer, antimalarial and antimicrobial [13,14].…”