Isolation, Characterization, Crystal Structure Elucidation, and Anticancer Study of Dimethyl Cardamonin, Isolated from Syzygium campanulatum Korth

Abstract

Syzygium campanulatum Korth is an equatorial, evergreen, aboriginal shrub of Malaysia. Conventionally it has been used as a stomachic. However, in the currently conducted study dimethyl cardamonin or 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone (DMC) was isolated from S. campanulatum Korth, leaf extract. The structural characterization of DMC was carried out by making use of various techniques including UV, IR, NMR spectral followed by LC-MS, and X-ray crystallographic techniques. For determining the purity of compound, highly effective techniques including TLC, HPLC, and melting point were used. The cytotoxicity of DMC and three different extracts of S. campanulatum was evaluated against human colon cancer cell line (HT-29) by three different assays. DMC and ethanolic extract revealed potent and dose-dependent cytotoxic activity on the cancer cell line with IC50 12.6 and 90.1 µg/mL, respectively. Quite astonishingly to our knowledge, this is the very first report on S. campanulatum as being a rich source (3.5%) of DMC, X-ray crystallography, and anticancer activity on human colon cancer cells.

Isolation, Characterization, Crystal Structure Elucidation of Two Flavanones and Simultaneous RP-HPLC Determination of Five Major Compounds from Syzygium campanulatum Korth

“…The UV-Vis spectra of compounds (1)(2)(3)(4)(5) showed absorption at λmax 330 and 210 nm ( Figure 1). (5) and (E)-2ʹ,4ʹ-dihydroxy-6ʹ-methoxy chalcone (6).…”

“…Figure 3. PCA data can be used to differentiate age of plant with maximum concentration of all compounds (1)(2)(3)(4)(5).…”

“…Therefore mobile phase containing 0. The concentration of each compound (1)(2)(3)(4)(5) in the extracts of different age plants was calculated from the experimental peak areas by interpolation to standard calibration curves (Table 3). Table 3.…”

“…It is widely distributed from Malaysia to north-eastern Australia [1]. It is reported that the genus Syzygium is rich in secondary metabolites such as terpenoids [2,3], phenylpropanoids [4], chalcones [5], flavonoids [6], lignans [7], alkyl phloroglucinols [8], hydrolysable tannins and chromone derivatives [9]. Therapeutically, Syzygium genus is used in the treatment of rheumatism [10], haemorrhage, GIT disorders [11], diabetes [12], inflammation, allergy [13,14], convulsion [15], hypertension [16] and bacterial infections [17].…”

“…Despite its wide distribution, scientific research about S. campanulatum is scarce. Memon et al, 2014 reported isolation, characterization, crystal structure elucidation, and anticancer effect of dimethyl cardamonin isolated from Syzygium campanulatum Korth [5]. Aisha et al, 2013 reported anti-angiogenesis and antitumor effects of Syzygium campanulatum extracts [18].…”