CC BY-NC-ND 4.0 · Planta Medica International Open 2021; 8(03): e114-e121
DOI: 10.1055/a-1543-1261
Original Papers

Triterpenoids from Alisma orientale and their NF-кB Inhibitory Activity

Qian Yang
1   State Key Lab. of New Drug and Pharmaceutical Process, China State Institute of Pharmaceutical Industry, Shanghai, PR China
4   Innovation center of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai, PR China
,
Yinqing Li
2   Shineway Pharmaceutical Group Ltd., Shijiazhuang, PR China
3   Hebei key Laboratory of Famous Classical Formulas and TCM Quality Process Control, Shijiazhuang, PR China
,
Xizi Liu
1   State Key Lab. of New Drug and Pharmaceutical Process, China State Institute of Pharmaceutical Industry, Shanghai, PR China
4   Innovation center of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai, PR China
,
Shiyi Han
1   State Key Lab. of New Drug and Pharmaceutical Process, China State Institute of Pharmaceutical Industry, Shanghai, PR China
4   Innovation center of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai, PR China
,
Siyang Fan
1   State Key Lab. of New Drug and Pharmaceutical Process, China State Institute of Pharmaceutical Industry, Shanghai, PR China
4   Innovation center of Traditional Chinese Medicine, Shanghai Institute of Pharmaceutical Industry, Shanghai, PR China
› Author Affiliations
Funding This work was supported by grants from the National Natural Science Foundation of China (No. 81603279), the National Science and Technology Project of China (No. 2018ZX09731–016), and the S&T Program of Hebei (20272502D).

Abstract

The rhizome of Alisma orientale (sam.) Juz. is used in clinics for eliminating dampness, reducing edema, and promoting diuresis. This study aimed to elucidate the compounds and investigate their nuclear factor-kappa inhibitory activities in human embryonic kidney 293 cells. A new triterpene, alismaketone B (1); a new natural nortriterpene, noralisolic acid A (2); and 13 known protostane-type triterpenes were isolated from the rhizome of A. orientale. The new structures and their absolute configurations were established using HRESIMS, NMR, and electronic circular dichroism experiments. All isolated compounds were evaluated for their inhibitory activity on NF-κB. The compounds 8, 9, 10, and 14 showed moderate NF-κB inhibitory activities with their IC50 values being 64.7, 32.3, 47.3, and 37.3 μM, respectively.

Supplementary Material



Publication History

Received: 10 March 2021
Received: 23 June 2021

Accepted: 25 June 2021

Article published online:
25 August 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).

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  • References

  • 1 Pharmacopoeia CoN. Pharmacopoeia of the People's Republic of China. Beijing: The Medicine Science and Technology Press of China; 2020
  • 2 Shu Z, Pu J, Chen L, Zhang Y, Rahman K, Qin L, Zheng C. Alisma orientale: Ethnopharmacology, phytochemistry and pharmacology of an important traditional Chinese medicine. Am J Chin Med 2016; 44: 227-251
  • 3 Zhang LL, Xu W, Xu YL, Chen X, Huang M, Lu JJ. Therapeutic potential of Rhizoma Alismatis: a review on ethnomedicinal application, phytochemistry, pharmacology, and toxicology. Ann N Y Acad Sci 2017; 1401: 90-101
  • 4 Li HM, Chen XJ, Luo D, Fan M, Zhang ZJ, Peng LY, Wu XD, Li RT, Ji X, Zhao Q-S. Protostane-type triterpenoids from Alisma orientale . Chem Biodivers 2017; 14: e1700452
  • 5 Xin XL, Xin XL, Zhao XY, Huo XK, Sun CP, Zhang HL, Tian Y, Zhao XY, Liu Y, Tian X-G, Wang X. Two new protostane-type triterpenoids from Alisma orientalis . Nat Prod Res 2018; 32: 189-194
  • 6 Li HM, Fan M, Xue Y, Peng LY, Wu XD, Liu D, Li RT, Zhao QS. Guaiane-type sesquiterpenoids from Alismatis rhizoma and their anti-inflammatory activity. Chem Pharm Bull 2017; 65: 403-407
  • 7 Feng YL, Chen H, Tian T, Chen DQ, Zhao YY, Lin RC. Diuretic and anti-diuretic activities of the ethanol and aqueous extracts of Alismatis rhizoma . J Ethnopharmacol 2014; 154: 386-390
  • 8 Xu F, Yu H, Lu C, Chen J, Gu W. The cholesterol-lowering effect of alisol acetates based on HMG-CoA reductase and its molecular mechanism. Evid Based Complement Alternat Med 2016; 2016: 4753852
  • 9 Huo XK, Liu J, Yu ZL, Wang YF, Wang C, Tian XG, Ning J, Feng L, Sun CP, Zhang BJ, Ma XC. Alisma orientale extract exerts the reversing cholestasis effect by activation of farnesoid X receptor. Phytomedicine 2018; 42: 34-42
  • 10 Lin HR. Triterpenes from Alisma orientalis act as farnesoid X receptor agonists. Bioorg Med Chem Lett 2012; 22: 4787-4792
  • 11 Zhao XY, Wang G, Wang Y, Tian XG, Zhao JC, Huo XK, Sun CP, Feng L, Ning J, Wang C, Zhang B-J, Wang X. Chemical constituents from Alisma plantago-aquatica subsp. orientale (Sam.) Sam and their anti-inflammatory and antioxidant activities. Nat Prod Res 2018; 32: 2749-2755
  • 12 Dou F, Miao H, Wang JW, Chen L, Wang M, Chen H, Wen AD, Zhao YY. An integrated lipidomics and phenotype study reveals protective effect and biochemical mechanism of traditionally used Alisma orientale juzepzuk in chronic kidney disease. Front Pharmacol 2018; 9: 53
  • 13 Han CW, Kwun MJ, Kim KH, Choi JY, Oh SR, Ahn KS, Lee JH, Joo M. Ethanol extract of Alismatis rhizoma reduces acute lung inflammation by suppressing NF-κB and activating Nrf2. J Ethnopharmacol 2013; 146: 402-410
  • 14 Kim KH, Kwun MJ, Choi JY, Ahn KS, Oh SR, Lee YG, Christman JW, Sadikot RT, Han CW, Joo M. Therapeutic effect of the tuber of Alisma orientale on lipopolysaccharide-induced acute lung injury. Evid Based Complement Alternat Med 2013; 2013: 863892
  • 15 Jin H-G, Jin Q, Ryun Kim A, Choi H, Lee JH, Kim YS, Lee DG, Woo ER. A new triterpenoid from Alisma orientale and their antibacterial effect. Arch Pharmacal Res 2012; 35: 1919-1926
  • 16 Nakajima Y, Satoh Y, Katsumata M, Tsujiyama K, Ida Y, Shoji J. Terpenoids of Alisma orientale rhizomes and the crude drug Alismatis rhizoma . Phytochemistry 1994; 36: 119-127
  • 17 Yoshikawa M, Murakami T, Ikebata A, Ishikado A, Murakami N, Yamahara J, Matsuda H. Absolute stereostructures of alismalactone 23-acetate and alismaketone-a 23-acetate, new seco-protostane and protostane-type triterpenes with vasorelaxant effects from Chinese Alismatis rhizoma . Chem Pharm Bull 1997; 45: 756-758
  • 18 Mai ZP, Wang C, Huo XK, Dong PP, Deng S, Zhang BJ, Zhang HL, Huang SS, Ma XC, Zhou K, Ge GB. Protostane triterpenoids from the rhizome of Alisma orientale exhibit inhibitory effects on human carboxylesterase 2. J Nat Prod 2015; 78: 2372-2380
  • 19 Hu XY, Guo YQ, Gao WY, Zhang TJ, Chen HX. Two new triterpenes from the rhizomes of Alisma orientalis . J Asian Nat Prod Res 2008; 10: 487-490
  • 20 Lainer J, Dawid C, Dunkel A, Gläser P, Wittl S, Hofmann T. Characterization of bitter-tasting oxylipins in poppy seeds (Papaver somniferum L.). J Agr and Food Chem 2020; 68: 10361-10373
  • 21 Matsuda H, Kageura T, Toguchida I, Murakami T, Kishi A, Yoshikawa M. Effects of sesquiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages: absolute stereostructures of alismaketones-B 23-acetate and-C 23-acetate. Bioorg Med Chem Lett 1999; 9 (21) 3081-3086
  • 22 Zhao M, Gödecke T, Gunn J, Anh Tuan L, Che C-T. Protostane and fusidane triterpenes: A mini-review. Molecules 2013; 18: 4054-4080
  • 23 Lee SM, Min BS, Bae KH. Chemical modification of alisol B 23-acetate and their cytotoxic activity. Arch Pharm Res 2002; 25: 608-612
  • 24 Ma Q, Han L, Bi X, Wang X, Mu Y, Guan P, Li L, Huang X. Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale . Phytochemistry 2016; 131: 150-157
  • 25 Kubo M, Matsuda H, Tomohiro N, Yoshikawa M. Studies on Alismatis Rhizoma. I. Anti-allergic effects of methanol extract and six terpene components from Alismatis rhizoma (dried rhizome of Alisma orientale). Biol Pharm Bull 1997; 20: 511-516
  • 26 Lee JH, Kwon OS, Jin HG, Woo ER, Kim YS, Kim HP. The rhizomes of Alisma orientale and alisol derivatives inhibit allergic response and experimental atopic dermatitis. Biol Pharm Bull 2012; 35: 1581-1587
  • 27 Shi FF, Wei W, Wang YC, Su QP, Xue XH. The effect of alisol A 24-acetate on lipid metabolic factors ABCA1, CD36 and inflammatory factors CD147, MMP-9 in oxidized low density lipoprotein-induced macrophages. Chin J Arteriosclerosis 2016; 24: 7-12
  • 28 Yang Q, Jia A, Liu XZ, Han SY, Fan SY. Chemical constituents from Chloranthus elatior and their inhibitory effect onhuman dihydroorotate dehydrogenase. Planta Med advance online publication 2021; doi: 10.1055/a-1449-2642
  • 29 Hino K, Nagata H, Shimonishi M, Ido M. High-throughput screening for small-molecule adiponectin secretion modulators. J Biomol Screen 2011; 16: 628-636