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

Molecules

Abdul Hakeem Memon¹  Zhari Ismail¹  Fouad Saleih Resq Al-Suede²  Abdalrahim F. A. Aisha¹  Mohammad Shahrul Ridzuan Hamil¹  Mohammed Ali Ahmed Saeed¹  Madeeha Laghari³  Amin Malik Shah Abdul Majid² 

[1] Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia; E-Mails:;EMAN Research and Testing Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia; E-Mails:;Department of Pharmaceutical Technology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800-Minden, Penang, Malaysia; E-Mail:

关键词: Syzygium campanulatum Korth;    secondary metabolites;    X-ray crystallography;    RP-HPLC;   

DOI  :  10.3390/molecules200814212

来源: mdpi

【 摘 要 】

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 (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, 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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.