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

Abstract

Two flavanones named (2S)-7-Hydroxy-5-methoxy-6,8-dimethyl flavanone (1), (S)-5,7-dihydroxy-6,8-dimethyl-flavanone (2), along with known chalcone, namely, (E)-2ʹ,4ʹ-dihydroxy-6ʹ-methoxy-3ʹ,5ʹ-dimethylchalcone (3) and two triterpenoids, namely, betulinic and ursolic acids (4 and 5), were isolated from the leaves of Syzygium campanulatum Korth (Myrtaceae). The structures of compounds (1 and 2) were determined on the basis of UV-visible, FTIR, NMR spectroscopies and LC-EIMS analytical techniques. Furthermore, new, simple, precise, selective, accurate, highly sensitive, efficient and reproducible RP-HPLC method was developed and validated for the quantitative analysis of the compounds (1-5) from S. campanulatum plants of five different age. RP-HPLC method was validated in terms of specificity, linearity (r 2 ≤ 0.999), precision (2.0% RSD), and recoveries (94.4%-105%). The LOD and LOQ of these compounds ranged from 0.13-0.38 and 0.10-2.23 µg·mL −1 , OPEN ACCESSMolecules 2015, 20 14213 respectively. Anti-proliferative activity of isolated flavanones (1 and 2) and standardized extract of S. campanulatum was evaluated on human colon cancer (HCT 116) cell line. Compounds (1 and 2) and extract revealed potent and dose-dependent activity with IC50 67.6, 132.9 and 93.4 µg·mL −1 , respectively. To the best of our knowledge, this is the first study on isolation, characterization, X-ray crystallographic analysis of compounds (1 and 2) and simultaneous RP-HPLC determination of five major compounds (1-5) from different age of S. campanulatum plants.

Assessing product adulteration ofEurycoma longifolia(Tongkat Ali) herbal medicinal product using DNA barcoding and HPLC analysis

“…The results were calculated as % w/w using the formula: (calculated concentration/Loaded concentration × 100% (Memon et al. 2015 ).…”

Potential anti-viral compounds from Malaysian Plant Natural Product Repository and Database (MyNature50000) for DENV2

“…Correspondingly, several high polarity volatile compounds have been isolated from other plants belonging to the same genus Syzygium, including triterpene glycoside, myricetin 4-O-methylether-3-O-a-L-rhamnopyranoside, myricetin 3-O-b-D-glucopyranoside, ursolic acid, quadranoside IV, friedelin, b-sitosterol, botulin, phenethyl D-rutinoside, officinoside B, crotalionoside C, and n-butyl-b-D-fructopyranoside [24]. In another study, the leaf extract of S. campanulatum Korth was shown to contain two types of flavanones which were later identified as (2S)-7-hydroxy-5-methoxy-6,8dimethyl flavanone and (S)-5,7-dihydroxy-6,8-dimethylflavanone, along with the known chalcone, (E)-2 0 ,4 0 - dihydroxy-6 0 -methoxy-3 0 ,5 0 -dimethylchalcone and two triterpenoids, namely, betulinic and ursolic acids which reportedly impart anti-proliferative activity to the isolated flavanone compounds [25]. Volatile compounds are also found in the Syzygium genus and therapeutically used such as S. aromatic.…”

A comparative study of conventional and supercritical fluid extraction methods for the recovery of secondary metabolites from Syzygium campanulatum Korth

“…The quantifications of HMDF, HMF, DMC, BA, and UA in crude extracts were performed using the HPLC method as previously described (Memon et al, 2015). Briefly, analysis was performed using a C-18 reverse phase ZORBAX Eclipse Plus Phenyl Hexyl column (4.6 mm×250 mm, 5 µm).…”

“…Traditionally, it is reported as a stomachic (Memon et al, 2014). Scientifically, its n-hexane: methanol (n-HEX:MeOH) extract is characterized as (E)-2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (DMC), (2S)-7-hydroxy-5-methoxy-6,8-dimethyl flavanone (HMDF), (S)-5,7-dihydroxy-6,8-dimethylflavanone (HMF), betulinic acid (BA), and ursolic acid (UA) (Memon et al, 2014;2015). The MeOH extract of S. campanulatum has been analyzed for anticolon cancer activity (Aisha et al, 2013).…”