| ORIGINAL ARTICLES |
|
|
|
|
|
Two pyrrole acids isolated from Phyllanthus emblica L. and their bioactivities |
| Shu-Hui Wang, Cong Guo, Wen-Jin Cui, Qing-Xia Xu, Jun Zhang, Jin-Zhu Jiang, Yan Liu, Sha Chen, Chang Chen, Jin-Tang Cheng, An Liu |
| Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, China |
|
|
|
|
Abstract An undescribed pyrrole acid, 1-(4'-methoxy-4'-oxobutyl)-1 H-pyrrole-2,5-dicarboxylic acid (1) and one known pyrrole acid (2) were isolated from the fruits of Phyllanthus emblica. The structures of these compounds were elucidated via the comprehensive analyses of IR, HRESIMS, 1D and 2D spectroscopic data. A series of biological assays revealed that compounds 1 and 2 could inhibit LPS-induced over-production of nitric oxide (NO), interleukin-6 (IL-6), monocyte chemotactic protein 1 (MCP-1) and tumor necrosis factor-α (TNF-α) by reducing the phosphorylation of extracellular regulated protein kinases (ERK) and c-Jun N-terminal kinases (JNK) in RAW 264.7 cells. Additionally, compounds 1 and 2 were found to reduce lipid deposition and increase the mRNA expression of ATP-binding cassette transporter A1 in oxidized low-density lipoprotein-treated RAW264.7 macrophages.
|
| Keywords
Pyrrole acid
Phyllanthus emblica L.
Lipid deposition
ATP-binding cassette transporter A1
RAW264.7 macrophages
|
| Fund:We gratefully acknowledge financial support from Scientific and technological innovation project of China Academy of Chinese Medical Sciences (CI2021A04409, CI2021A04404, CI2021A04405), the fundamental research funds for the central public welfare research institutes (No. ZZ13-YQ-061, ZXKT22012, ZXKT22039). |
|
Corresponding Authors:
Jin-Tang Cheng,E-mail:jtcheng@icmm.ac.cn;An Liu,E-mail:la62@163.com
E-mail: la62@163.com;jtcheng@icmm.ac.cn;la62@163.com
|
|
Issue Date: 08 October 2023
|
|
|
1. Bäck M, Hansson GK. Anti-inflammatory therapies for atherosclerosis. Nat Rev Cardiol. 2015;12:199–211.
2. Liu Z, Xu S, Huang X, Wang J, Gao S, Li H, Zhou C, Ye J, Chen S, Jin ZG, Liu P. Cryptotanshinone, an orally bioactive herbal compound from Danshen, attenuates atherosclerosis in apolipoprotein E-deficient mice: role of lectin-like oxidized LDL receptor-1 (LOX-1). Br J Pharm. 2015;172:5661–75.
3. Angelovich TA, Hearps AC, Jaworowski A. Inflammation-induced foam cell formation in chronic inflammatory disease. Immunol Cell Biol. 2015;93:683–93.
4. Newman DJ, Cragg GM. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J Nat Prod. 2020;83:770–803.
5. Cragg GM, Newman DJ. Natural products: a continuing source of novel drug leads. Biochim Biophys Acta. 2013;1830:3670–95.
6. Kumaran A, Karunakaran RJ. Nitric oxide radical scavenging active components from Phyllanthus emblica L. Plant Food Hum Nutr. 2006;61:1–5.
7. Luo W, Zhao M, Yang B, Ren J, Shen G, Rao G. Antioxidant and antiproliferative capacities of phenolics purified from Phyllanthus emblica L. fruit. Food Chem. 2011;126:277–82.
8. Mathai RT, Tonse R, Kalekhan F, Colin MD, Prabhu HS, Rao S, Baliga MS. Chapter 3-Amla in the prevention of aging: scientific validation of the ethnomedicinal claims. In: Watson RR, editor. Foods and Dietary supplements in the Prevention and Treatment of Disease in older adults. San Diego: Academic Press; 2015. pp. 29–35.
9. Yang B, Kortesniemi M, Liu P, Karonen M, Salminen JP. Analysis of hydrolyzable tannins and other phenolic compounds in emblic leafflower (Phyllanthus emblica L.) fruits by high performance liquid chromatography-electrospray lonization mass spectrometry. J Agric Food Chem. 2012;60:8672–83.
10. Sreeramulu D, Raghunath M. Antioxidant activity and phenolic content of roots, tubers and vegetables commonly consumed in India. Food Res Int. 2010;43:1017–20.
11. Ryu YB, Kim JH, Park SJ, Chang JS, Rho MC, Bae KH, Park KH, Lee WS. Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis. Bioorg Med Chem Lett. 2010;20:971–4.
12. Buzzini P, Arapitsas P, Goretti M, Branda E, Turchetti B, Pinelli P, Ieri F, Romani A. Antimicrobial and antiviral activity of hydrolysable tannins. Mini-rev Med Chem. 2008;8:1179–87.
13. Adams LS, Seeram NP, Aggarwal BB, Takada Y, Sand D, Heber D. Pomegranate juice, total pomegranate ellagitannins, and punicalagin suppress inflammatory cell signaling in colon cancer cells. J Agric Food Chem. 2006;54:980–5.
14. Matito C, Mastorakou F, Centelles J, Torres J, Cascante M. Antiproliferative effect of antioxidant polyphenols from grape in murine Hepa-1C1C7. Eur J Nutr. 2003;42:43–9.
15. Gao Q, Xiang HY, Chen W, Ling J, Chen X, Li J, Zhang TD, Li XM, Zou M, Yang GY, Hu QF. Two new isobenzofuranone derivatives from Phyllanthus emblica and their bioactivity. Chem Nat Comp. 2019;55:847–50.
16. Mahata S, Pandey A, Shukla S, Tyagi A, Husain SA, Das BC, Bharti AC. Anticancer activity of Phyllanthus emblica Linn. (indian gooseberry): inhibition of transcription factor AP-1 and HPV gene expression in cervical cancer cells. Nutr Cancer. 2013;65:88–97.
17. Yokozawa T, Kim HY, Kim HJ, Tanaka T, Sugino H, Okubo T, Chu DC, Juneja LR. Amla (Emblica officinalis Gaertn.) Attenuates age-related renal dysfunction by oxidative stress. J Agric Food Chem. 2007;55:7744–52.
18. Majeed M, Bhat B, Jadhav AN, Srivastava JS, Nagabhushanam K. Ascorbic acid and tannins from Emblica officinalis Gaertn. fruits-A revisit. J Agric Food Chem. 2009;57:220–5.
19. Liu H, Qiu N, Ding H, Yao R. Polyphenols contents and antioxidant capacity of 68 chinese herbals suitable for medical or food uses. Food Res Int. 2008;41:363–70.
20. Yang B, Liu P. Composition and biological activities of hydrolysable tannins of fruits of Phyllanthus emblica. J Agric Food Chem. 2014;62:529–41.
21. Colucci R, Dragoni F, Conti R, Pisaneschi L, Lazzeri L, Moretti S. Evaluation of an oral supplement containing Phyllanthus emblica fruit extracts, vitamin E, and carotenoids in vitiligo treatment. Dermatol Ther. 2015;28:17–21.
22. Scartezzini P, Antognoni F, Raggi MA, Poli F, Sabbioni C. Vitamin C content and antioxidant activity of the fruit and of the ayurvedic preparation of Emblica officinalis Gaertn. J Ethnopharmacol. 2006;104:113–8.
23. Ruangchakpet A, Sajjaanantakul T. Effect of browning on total phenolic, flavonoid content and antioxidant activity in indian gooseberry (Phyllanthus emblica Linn). Kasetsart J (Nat Sci). 2007;41:331–7.
24. Rose K, Wan C, Thomas A, Seeram NP, Ma H. Phenolic compounds isolated and identified from Amla (Phyllanthus emblica) juice powder and their antioxidant and neuroprotective activities. Nat Prod Commun. 2018;13:1309–11.
25. Gaire BP, Subedi L. Phytochemistry, pharmacology and medicinal properties of Phyllanthus emblica Linn. Chin J Integr Med. 2014. https://doi.org/10.1007/s11655-014-1984-2.
26. Wang SH, Cheng JT, Guo C, Cui WJ, Shi J, Liu A. Study on chemical constituents of. Phyllanthus emblica Zhongcaoyao. 2019;50:4873–8.
27. Koštálová D, Hrochová V, Suchý V, Buděšínský M, Ubik K. Two pyrrole acids from Berberis koreana. Phytochemistry. 1992;31:3669–70.
28. Gaestel M, Kotlyarov A, Kracht M. Targeting innate immunity protein kinase signaling in inflammation. Nat Rev Drug Discov. 2009;8:480–99.
29. Ma Q, Zhang XM, Jiang JG, Zhu W. Apigenin-7-O-β-D-glucuronide inhibits modified low-density lipoprotein uptake and foam cell formation in macrophages. J Funct Foods. 2017;35:615–21.
30. Shen CY, Jiang JG, Huang CL, Zhu W. Gypenoside LVI attenuates foam cell formation by promoting cholesterol export and inhibiting inflammation response. J Funct Foods. 2018;50:71–7.
31. Shrestha E, Hussein MA, Savas JN, Ouimet M, Barrett TJ, Leone S, Yates JR, Moore KJ, Fisher EA, Garabedian MJ. Poly (ADP-ribose) polymerase 1 represses liver x receptor-mediated ABCA1 expression and cholesterol efflux in macrophages. J Biol Chem. 2016;291:11172–84. |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
| |
Shared |
|
|
|
|
| |
Discussed |
|
|
|
|
