Inhibition of NO production in LPS-stimulated RAW264.7 macrophage cells with curcuminoids and xanthorrhizol from the rhizome of Curcuma xanthorrhiza Roxb. and quantitative analysis using HPLC

• Published in: Applied biological chemistry Vol. 57; no. 3; pp. 407 - 412
• Main Authors: Park, Ji-Hae, Jung, Ye-Jin, Shrestha, Sabina, Lee, Sang Min, Lee, Tae Hoon, Lee, Chang-Ho, Han, Daeseok, Kim, Jiyoung, Baek, Nam-In
• Format: Journal Article
• Language: English
• Published: Seoul The Korean Society for Applied Biological Chemistry 01.06.2014; Springer Nature B.V; 한국응용생명화학회
• Subjects: Applied Microbiology; Biological Techniques; Bioorganic Chemistry; Chemistry; Chemistry and Materials Science; Chromatography; Column chromatography; Curcuma zanthorrhiza; Curcumin; High performance liquid chromatography; Identification methods; Infrared spectroscopy; Lipopolysaccharides; Liquid chromatography; Macrophages; Mass spectrometry; Mass spectroscopy; Nitric oxide; NMR; Nuclear magnetic resonance; Quantitative analysis; Resins; Rhizomes; Silica; Silica gel; Silicon dioxide; Xanthorrhizol; 농학; xanthorrhizol; high performance liquid chromatography; curcuminoid; nitric oxide production
• ISSN: 1738-2203; 2468-0834; 2234-344X; 2468-0842
• DOI: 10.1007/s13765-014-4132-y

Three diarylheptanoids, bisdemethoxycurcumin ( 1 ), curcumin ( 2 ), and demethoxycurcumin ( 3 ), two diarylpentanoids, 3,3′-bis(7,7′-hydroxy-6,6′-methoxyphenyl)-penta-(3 E ,2′ E )-3,2′-dien-1-one ( 4 ) and 3,3′-bis(7,7′-hydroxy-6-methoxyphenyl)-penta-(3 E ,2′ E )-3,2′-dien-1-one ( 5 ), and a bisabolane sesquiterpene, xanthorrhizol ( 6 ), were isolated from the rhizome of Curcuma xanthorrhiza through repeated column chromatography. Silica gel (SiO 2 ), octadecyl silica gel (ODS), and Sephadex LH-20 resins were used. Compounds were identified by spectroscopic methods, including nuclear magnetic resonance, mass spectrometry, and infrared spectroscopy. Compounds 1 (IC 50 : 8.21 μM), 2 (IC 50 : 10.01 μM), 3 (IC 50 : 4.86 μM), and 4 (IC 50 : 2.20 μM) inhibited nitric oxide production in LPS-stimulated RAW264.7 macrophage cells. High performance liquid chromatography was used to determine the content of curcuminoids and xanthorrhizol in C. xanthorrhiza extract to be 0.46±0.08% ( 1 ), 10.69±0.18% ( 2 ), 2.35±0.06% ( 3 ), 0.18±0.05% ( 4 ), 0.03±0.01% ( 5 ), and 27.47±2.42% ( 6 ).