New seco-anthraquinone glucoside from the roots of Rumex crispus

doi:10.1007/s13659-022-00350-3

Natural Products and Bioprospecting ›› 2022, Vol. 12 ›› Issue (5): 29-29.DOI: 10.1007/s13659-022-00350-3

• ORIGINAL ARTICLES • Previous Articles Next Articles

New seco-anthraquinone glucoside from the roots of Rumex crispus

Yong-Xiang Li^1,2, Na Li¹, Jing-Juan Li¹, Man Zhang¹, Hong-Tao Zhu¹, Dong Wang¹, Ying-Jun Zhang^1,3

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3 Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China

Received:2022-05-05 Revised:2022-06-07 Online:2022-10-12 Published:2022-10-24
Contact: Ying Jun Zhang,E-mail:zhangyj@mail.kib.ac.cn
Supported by:
This research was supported by Ministry of Science and Technology of the People's Republic of China,2021YFE0103600.

New seco-anthraquinone glucoside from the roots of Rumex crispus

Yong-Xiang Li^1,2, Na Li¹, Jing-Juan Li¹, Man Zhang¹, Hong-Tao Zhu¹, Dong Wang¹, Ying-Jun Zhang^1,3

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
3 Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China

通讯作者: Ying Jun Zhang,E-mail:zhangyj@mail.kib.ac.cn
基金资助:
This research was supported by Ministry of Science and Technology of the People's Republic of China,2021YFE0103600.

Abstract

Abstract: A new seco-anthraquinone, crispuside A (1), and three new 3,4-dihydronaphthalen-1(2H)-ones, napthalenones A-C (2–4), were isolated from the roots of Rumex crispus L., along with 10 known anthraquinones (6–14) and naphthalenone (5). Their structures were fully determined by extensive spectroscopic analyses, including ECD, and X-ray crystallography in case of compound 5, whose absolute configuration was determined for the first time. The isolates 1, 6–14 were evaluated for their anti-inflammatory and anti-fungal activity against three skin fungi, e.g., Epidermophyton floccosum, Trichophyton rubrum, and Microsporum gypseum. Most of the isolates showed weak antifungal and anti-inflammatory activity. Only compound 9 exhibited obvious anti-fungal activity against E. floccosum (MIC₅₀ = 2.467 ± 0.03 μM) and M. gypseum ( MIC₅₀ = 4.673 ± 0.077 μM), while the MIC₅₀ values of the positive control terbinafine were 1.287 ± 0.012 and 0.077 ± 0.00258 μM, respectively. The results indicated that simple emodin type anthraquinone is more potential against skin fungi than its oxyglucosyl, C-glucosyl and glycosylated seco analogues.

Key words: Polygonaceae, Rumex crispus L., Anthranoids, Anti-fungal activity

摘要： A new seco-anthraquinone, crispuside A (1), and three new 3,4-dihydronaphthalen-1(2H)-ones, napthalenones A-C (2–4), were isolated from the roots of Rumex crispus L., along with 10 known anthraquinones (6–14) and naphthalenone (5). Their structures were fully determined by extensive spectroscopic analyses, including ECD, and X-ray crystallography in case of compound 5, whose absolute configuration was determined for the first time. The isolates 1, 6–14 were evaluated for their anti-inflammatory and anti-fungal activity against three skin fungi, e.g., Epidermophyton floccosum, Trichophyton rubrum, and Microsporum gypseum. Most of the isolates showed weak antifungal and anti-inflammatory activity. Only compound 9 exhibited obvious anti-fungal activity against E. floccosum (MIC₅₀ = 2.467 ± 0.03 μM) and M. gypseum ( MIC₅₀ = 4.673 ± 0.077 μM), while the MIC₅₀ values of the positive control terbinafine were 1.287 ± 0.012 and 0.077 ± 0.00258 μM, respectively. The results indicated that simple emodin type anthraquinone is more potential against skin fungi than its oxyglucosyl, C-glucosyl and glycosylated seco analogues.

关键词: Polygonaceae, Rumex crispus L., Anthranoids, Anti-fungal activity

Yong-Xiang Li, Na Li, Jing-Juan Li, Man Zhang, Hong-Tao Zhu, Dong Wang, Ying-Jun Zhang. New seco-anthraquinone glucoside from the roots of Rumex crispus[J]. Natural Products and Bioprospecting, 2022, 12(5): 29-29.

Yong-Xiang Li, Na Li, Jing-Juan Li, Man Zhang, Hong-Tao Zhu, Dong Wang, Ying-Jun Zhang. New seco-anthraquinone glucoside from the roots of Rumex crispus[J]. 应用天然产物, 2022, 12(5): 29-29.

References

1. Augustin N, Nuthakki VK, Abdullaha M, Hassan QP, Gandhi SG, Bharate SB. Discovery of helminthosporin, an anthraquinone isolated from Rumex abyssinicus Jacq as a dual cholinesterase inhibitor. ACS Omega. 2020;5:1616–24.
2. Demirezer Ö, Kuruüzüm A, Bergere I, Schiewe HJ, Zeeck A. Five naphthalene glycosides from the roots of Rumex patientia. Phytochemistry. 2001;56:399–402.
3. Orsolya OG, Ildikó L, Judit H, Gusztáv J, Andrea V. Xanthine oxidase inhibitory activity of extracts prepared from Polygonaceae species. Phytother Res. 2015;29:459–65.
4. Bicker J, Petereit F, Hensel A. Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L. Fitoterapia. 2009;80:483–95.
5. Zhang H, Guo Z, Wu N, Xu WM, Han L, Li N, Han YX. Two novel naphthalene glucosides and an anthraquinone isolated from Rumex dentatus and their antiproliferation activities in four cell lines. Molecules. 2012;17:843–50.
6. Vasas A, Orbán-Gyapai O, Hohmann J. The genus Rumex: review of traditional uses, phytochemistry and pharmacology. J Ethnopharmacol. 2015;175:198–228.
7. Jeong KS. Extraction characteristics of soluble solid from Rumex crispus(curled dock) roots. J Environ Sci Int. 2011;20:1265–72.
8. Zhang Y, Xu H, Chen H, Wang F, Huai H. Diversity of wetland plants used traditionally in china: a literature review. J Ethnobiol Ethnomed. 2014;10:72.
9. Shim KS, Lee B, Ma JY. Water extract of Rumex crispus prevents bone loss by inhibiting osteoclastogenesis and inducing osteoblast mineralization. BMC Complementary Med Ther. 2017;17:483.
10. Shariati MA. Bioactive compounds and health benefits of edible Rumex species-a review. Cell Mol Biol. 2018;64:27–34.
11. Park ES, Song GH, Kim SH, Lee SM, Kim YG, Lim YL, Kang SA, Park KY. Rumex crispus and Cordyceps militaris mixture ameliorates production of pro-inflammatory cytokines induced by lipopolysaccharide in C57bl/6 mice splenocytes. Prev Nutr Food Sci. 2018;23:374.
12. Eom T, Kim E, Kim JS. In vitro antioxidant, antiinflammation, and anticancer activities and anthraquinone content from Rumex crispus root extract and fractions. Antioxidants. 2020;9:726.
13. Feduraev P, Chupakhina G, Maslennikov P. Variation in phenolic compounds content and antioxidant activity of different plant organs from Rumex crispus L. and Rumex obtusifolius L. at different growth stages. Antioxidants. 2019;8:237.
14. Minh TN, Van TM, Andriana Y, Vinh LT, Hau DV, Duyen DH, Guzman-Gelani C. Antioxidant, xanthine oxidase, α-amylase and α-glucosidase inhibitory activities of bioactive compounds from Rumex crispus L. Root Molecules. 2019;24:3899.
15. Jiang L, Zhang S, Xuan L. Oxanthrone C-glycosides and epoxynaphthoquinol from the roots of Rumex japonicus. Phytochemistry. 2007;68:2444–9.
16. Mei R, Liang H, Wang J, Zeng L, Lu Q, Cheng YX. New seco-anthraquinone glucosides from Rumex nepalensis. Planta Med. 2009;75:1162–4.
17. Zhang X, Liu F, Feng ZM, Yang YN, Jiang JS, Zhang PC. Bioactive phenylpropanoid esters of sucrose and anthraquinones from polygonum cuspidatum. Fitoterapia. 2020;146: 104673.
18. Yang L, Li T, Yang L, Dong L, Chen J. Two-dimensional correlation spectroscopy indicates the infrared spectral markers of the optimum scorching degree of rhubarb (Rhei Radix et Rhizoma) to enhance the anti-inflammatory activity. Spectrochim Acta Part A. 2022;270:120853.
19. Kim G, Xu YJ, Farha AK, Sui ZQ, Corke H. Bactericidal and antibiofilm properties of Rumex japonicus Houtt. on multidrug-resistant Staphylococcus aureus isolated from milk. J Dairy Sci. 2022;105:2011–24.
20. Liu X, Ma S, Huang Y, Li L. Identification of metabolites of Dachengqi Decoction in human intestinal microflora in vitro by HPLC-QTOF-MS/MS. Tradit Chin Drug Res Clin Pharmacol. 2021;32:1004–11.
21. Yu M, Chen TT, Zhang T, Jia HM, Li JJ, Zhang HW, Zou ZM. Anti-inflammatory constituents in the root and rhizome of Polygonum cuspidatum by UPLC-PDA-QTOF/MS and lipopolysaccharide-activated RAW264.7 macrophages. J Pharm Biomed Anal. 2021;195:113839.
22. Wang ZY, Zhao HP, Zuo YM, Wang ZQ, Tang XM. Two new C-glucoside oxanthrones from Rumex gmelini. Chin Chem Lett. 2009;20:839–41.
23. Yang Y, Yan YM, Wei W, Luo J, Zhang LS, Zhou XJ, Wang PC, Yang YX, Cheng YX. Anthraquinone derivatives from Rumex plants and endophytic Aspergillus fumigatus and their effects on diabetic nephropathy. Bioorg Med Chem Lett. 2013;23:3905–9.
24. Liu HJ, Chen SH, Liu WY, Liu YY, Huang XS, She ZG. Polyketides with immunosuppressive activities from Mangrove endophytic fungus Penicillium sp. ZJ-SY2. Mar Drugs. 2016;14:217.
25. Qi FF, Zhang W, Xue YY, Geng C, Huang XN, Sun J, Lu XF. Bienzymecatalytic and dioxygenation-mediated anthraquinone ring opening. J Am Chem Soc. 2021;143:16326–21633.
26. Tran TD, Wilson BAP, Henrich CJ, Staudt LM, Krumpe LRH, Smith EA, King J, Wendt KL, Stchigel AM, Miller AN, Cichewicz RH, O’Keefe BR, Gustafson KR. Secondary metabolites from the fungus Dictyosporium sp. and their MALT1 inhibitory activities. J Nat Prod. 2019;82:154–62.
27. Nhung LTH, Linh NTT, Cham BT, Thuy TT, Tam NT, Thien DD, Huong PTM, Tan VM, Tai BH, Anh NTH. New phenolics from Dianella ensifolia Nat. Prod Res. 2019;35:3063–70.
28. Qu GX, Qi XL, Liu HW, Cai QF. Preliminary screening of traditional Chinese anti-fungi medicines. J Shenyang Pharm Univ. 2002;03:218–20.
29. Xin Y, Xu J, Lv JJ, Zhu HT, Wang D, Yang CR, Zhang YJ. New ent-Kaurane and cleistanthane diterpenoids with potential cytotoxicity from Phyllanthus acidus (L.) Skeels. Fitoterapia. 2020;157:105133.

New seco-anthraquinone glucoside from the roots of Rumex crispus

New seco-anthraquinone glucoside from the roots of Rumex crispus

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 1

Recommended Articles

Metrics

Comments