Chemical Constituents from the Roots of Scrophularia ningpoensis Hemsl and Their Anti-inflammatory Activities
HUO Yu-feng1, ZHAN Zhi-lai2, WANG Huai-li1*, WEI Er-hu1, JIA Pei-sheng1, LIU Hui-qiong1, FAN Xiao-lei1, YAN Kun-li1
1. Department of Pediatrics, the First Affiliated Hospital of Zhengzhou University, Zhengzhou 450052, China;
2. National Resource Center for Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China
OBJECTIVE To study the chemical constituents in the roots of Scrophularia ningpoensis Hemsl. METHODSE Compounds were isolated by chromatographic techniques and their structures were elucidated by spectral methods. The anti-inflammatory activities of all isolated compounds were evaluated by lipopolysaccharides (LPS)-stimulated BV2 cells model. RESULTS Eighteen compounds were isolated and identified as 2'''-acetyl angroside C (1), saccatoside (2), 6-O-α-L-(2″-O-feruloyl)rhamnopyranosylcatalpol (3), scrophularioside (4), harprocumbide A (5), 6″-O-β-D-glucopyranosylharpagoside (6), harpagoside (7), 8-O-(p-coumaroyl)-harpagide (8), 8-O-feruloylharpagide (9), 6-O-α-D-galactopyranosylharpagoside (10), 6′-O-cinnamoylharpagide (11), angoroside B (12), angoroside C (13), scrophuloside B1 (14), 2-(3-hydroxy-4-methoxyphenyl)ethyl-O-α-L-arabinopyranosyl-(1→6)-O-α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (15), darendoside B (16), 6-O-caffeoyl-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside (17), and sibirioside A (18). CONCLUSION Compound 1 is new compound, and compounds 2-4, 12, 14, and 17 are isolated from this plant for the first time. Compounds 1, 12, and 13 show significant inhibition against nitric oxide production in LPS-stimulated BV2 cells model.
霍玉峰, 詹志来, 王怀立, 魏二虎, 贾沛生, 刘会琼, 范晓蕾, 闫坤丽. 中药玄参中化学成分及其抗炎活性研究[J]. 中国药学杂志, 2020, 55(14): 1207-1214.
HUO Yu-feng, ZHAN Zhi-lai, WANG Huai-li, WEI Er-hu, JIA Pei-sheng, LIU Hui-qiong, FAN Xiao-lei, YAN Kun-li. Chemical Constituents from the Roots of Scrophularia ningpoensis Hemsl and Their Anti-inflammatory Activities. Chinese Pharmaceutical Journal, 2020, 55(14): 1207-1214.
ZHANG W J, LIU Y Q, LI X C, et al. Chemical constituents from Scrophularia ningpoensis [J]. Acta Bot Yunnan(云南植物研究), 1994, 16(4): 407-412.
[3]
CHEN Y H, QI J, HUA J, et al. Structural characterization and identification of major constituents in Radix Scrophulariae by HPLC coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry [J]. Chin J Nat Med(中国天然药物), 2014, 12(1): 47-54.
[4]
HUA J, QI J, YU B Y. Iridoid and phenylpropanoid glycosides from Scrophularia ningpoensis Hemsl. and their α-glucosidase inhibitory activities [J]. Fitoterapia, 2014, 93: 67-73.
[5]
ZHU L J, HOU Y L, SHEN X Y, et al. Monoterpene pyridine alkaloids and phenolics from Scrophularia ningpoensis and their cardioprotective effect [J]. Fitoterapia, 2013, 88: 44-49.
[6]
LI Y M, JIANG S H, GAO W Y, et al. Liposoluble constituents from the roots of Scrophularia ningpoensis [J]. Acta Pharm Sin(药学学报), 1999, 34(6): 448-450.
[7]
HUO Y F, WANG H L, WEI E H, et al. Two new compounds from the roots of Scrophularia ningpoensis and their anti-inflammatory activities [J]. J Asian Nat Prod Res(亚洲天然产物研究杂志), 2019, 21(11):1083-1089.
[8]
OTSUKA H, SASAKI Y, YAMASAKI K. Iridoid diglycoside monoacyl esters from the leaves of Premna japonica [J]. J Nat Prod, 1990, 53(1):107-111.
[9]
OTSUKA H, KUBO N, SASAKI Y, et al. Iridoid diglycoside monoacyl esters from stems of Premna japonica [J]. Phytochemistry, 1991, 30(6):1917-1920.
[10]
JUNIOR P. Iso-scrophularioside, a new iridoid glucoside from Penstemon eriantherus [J]. Planta Med, 1981, 43(1):34-38.
[11]
QI J, CHEN J J, CHENG Z H, et al. Iridoid glycosides from Harpagophytum procumbens D.C. (devil′s claw) [J]. Phytochemistry, 2006, 67(13):1372-1377.
[12]
CHEN B, LIUY, LIU H W, et al. Iridoid and aromatic glycosides from Scrophularia ningpoensis Hemsl. and their inhibition of [Ca2+](i) increase induced by KCl [J]. Chem Biodivers, 2008, 5(9):1723-1735.
[13]
TIAN J F, YEX L, SHANG Y H, et al. Preparative isolation and purification of harpagoside and angroside C from the root of Scrophularia ningpoensis Hemsley by high-speed counter-current chromatography [J]. J Sep Sci, 2012, 35(19):2659-2664.
[14]
KIKUCHI T, MATSUDA S, KUBO Y, et al. New iridoid glucosides from Harpagophytum procumbens DC [J]. Chem Pharm Bull, 1983, 31(7):2296-2301.
[15]
LI Y M, JIANG S H, GAO W Y, et al. Iridoid glycosides from Scrophularia ningpoensis [J]. Phytochemistry, 1999, 50(1):101-104.
[16]
NIU Z R, WANG R F, SHANG M Y, et al. A new iridoid glycoside from Scrophularia ningpoensis [J]. Nat Prod Res, 2009, 23(13):1181-1188.
[17]
CALIS I, GROSS G A, STICHER O. Two phenylpropanoid glycosides from Scrophularia scopolii [J]. Phytochemistry, 1988, 27(5):1465-1468.
[18]
MIYASE T, MIMATSU A. Acylated iridoid and phenylethanoid glycosides from the aerial parts of Scrophularia nodosa [J]. J Nat Prod, 1999, 62(8):1079-1084.
[19]
CALIS I, SARACOGLU I, BASARAN A A, et al. Two phenethyl alcohol glycosides from Scutellaria orientalis subsp. pinnatifida [J]. Phytochemistry, 1993, 32(6):1621-1623.
[20]
WANG M F, SHAO Y, LI J G, et al. Antioxidative phenolic glycosides from Sage (Salvia officinalis) [J]. J Nat Prod, 1999, 62(3):454-456.
[21]
LIN W H, WANG T X, CAI M S, et al. Studies on the structures of cinnamoyl glucosides from the roots of Veronicastrum sibirics (L.) Pennell [J]. Acta Pharm Sin (药学学报), 1995, 30(10):752-756.
[22]
YANG S, TAMAI R, AKASHI S, et al. Synergistic effect of muramyldipeptide with lipopolysaccharide or lipoteichoic acid to induce inflammatory cytokines in human monocytic cells in culture [J]. Infect Immun, 2001, 69(4):2045-2053.