title: 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)-2',4'- dihydroxy-6'-methoxy-3',5'-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 (r2 ≤ 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 ACCESS 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.
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia. memon_h79@yahoo.com.
authors.forename: Abdul Hakeem
authors.initials: AH
authors.lastname: Memon
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia. ismailzhari@gmail.com.
authors.forename: Zhari
authors.initials: Z
authors.lastname: Ismail
authors.affiliation: EMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia.
authors.forename: Fouad Saleih Resq
authors.initials: FS
authors.lastname: Al-Suede
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia. abedaisheh@yahoo.com.
authors.forename: Abdalrahim F A
authors.initials: AF
authors.lastname: Aisha
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia. shahrul.ridzuan18@gmail.com.
authors.forename: Mohammad Shahrul Ridzuan
authors.initials: MS
authors.lastname: Hamil
authors.affiliation: Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia. mohali141@yahoo.com.
authors.forename: Mohammed Ali Ahmed
authors.initials: MA
authors.lastname: Saeed
authors.affiliation: Department of Pharmaceutical Technology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia. fairy_rose25@yahoo.com.
authors.forename: Madeeha
authors.initials: M
authors.lastname: Laghari
authors.affiliation: EMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia. aminmalikshah@gmail.com.
authors.forename: Amin Malik Shah Abdul
authors.initials: AM
authors.lastname: Majid
mesh_terms: D001688:Biological Products / Q000032:analysis*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D049109:Cell Proliferation / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D056148:Chromatography, Reverse-Phase / Q000379:methods*; D018360:Crystallography, X-Ray; D044950:Flavanones / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D045325:HCT116 Cells; D006801:Humans; D025341:Principal Component Analysis; D012015:Reference Standards; D015203:Reproducibility of Results; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D027842:Syzygium / Q000737:chemistry*
chemical_list: D001688:Biological Products; D044950:Flavanones; C028610:flavanone
keywords: RP-HPLC; Syzygium campanulatum Korth; X-ray crystallography; secondary metabolites