การแยกสารและการดัดแปรโครงสร้างของ 2´,4´-ไดไฮดรอกซี-6´- เมทอกซี-3´,5´-ไดเมทิลชาลโคน จากเมล็ดมะเกี๋ยงที่เหลือใชข้อง อุตสาหกรรมน้า ผลไม้เพื่อใชเ้ป็นสารตา้นมะเร็ง

Abstract

2´,4´-Dihydroxy-6´-methoxy-3´,5´-dimethylchalcone or DMC is chalcone which showed desirable bioactivities such as antioxidant, anticancer, antimicrobial, anti-inflammatory, antimalarial and cytotoxicity activities. Generally, the DMC was isolated from Syzygium plants for instance, Syzygium samarangense. Moreover, one of these plants which found in northern Thailand is Syzygium nervosum A. Cunn. Ex DC (Ma-Kiang). Therefore, we isolated DMC from the ethyl acetate crude extract of Ma-kiang seeds which was residue from juice industry in Lampang (4.3615 g, 1.64% yield). In =addition, the two isolated flavanones were (–)-5,7-dihydroxy-6,8-dimethylflavanone (62, 0.62% yield) and 7-hydroxy-5-methoxy-6,8-dimethylflavanone (63, 0.11% yield). Then, we modified DMC structure through several reactions, including methylation, acetylation, allylation, benzylation, benzoylation, naphthalenesulfonylation, 2-naphthoylation, p-toluoylation and benzenesulfonylation under basic condition. The resulting products consisted of O-substituted chalcone and O-protected flavanone derivatives obtained compound 64‒80. Moreover, all modified compounds will be evaluated for anticancer, cytotoxicity activities and antibacterial. The cytotoxicity against cancer cell lines (KKU-M213, FaDu, HT-29, MDA-MB-231, A-549 and SH-SY5Y), compound 64 exhibited the highest cytotoxicity for SH-SY5Y cell lines with ED50 2.35 µg/mL. Next, compound 71 exhibited cytotoxicity for A-549 cell line with ED50 3.88 µg/mL. Beyond, DMC (9) exhibited cytotoxicity for SH-SY5Y cell line with ED50 3.91 µg/mL. While, compounds that showed non-cytotoxicity against nomal cell lines (CL) were compounds 66, 68, 73 and 80. Besides, the cytotoxicity against bacterial S. aureus ATCC 25923, E. coli ATCC 25922 and P. aeruginosa ATCC 27853, DMC (9) and derivatives of DMC exhibited rather non-cytotoxicity for these bacteria.