Naphthoquinones from Onosma paniculatum with Potential Anti-inflammatory Activity

Miao Dong; Dan Liu; Yan-Hong Li; Xuan-Qin Chen; Kai Luo; Yong-Min Zhang; Rong-Tao Li

doi:10.1055/s-0042-120545

Planta Medica, Table of Contents

Planta Med 2017; 83(07): 631-635
DOI: 10.1055/s-0042-120545

Biological and Pharmacological Activity

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Naphthoquinones from Onosma paniculatum with Potential Anti-inflammatory Activity

Authors

Miao Dong^*

¹Faculty of Environmental Science and Engineering, Kunming University of Science and Technology, Kunming, China

²Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, China
Dan Liu^*

²Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, China
Yan-Hong Li

²Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, China
Xuan-Qin Chen

²Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, China
Kai Luo

³Paris School of Business, Management and Strategy Department, Paris, France
Yong-Min Zhang

⁴Université Pierre et Marie Curie-Paris 6, Institute Parisien de Chimie Moléculaire, Paris, France
Rong-Tao Li

²Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming, China

Abstract

Four new naphthoquinones (1–4), including a dimeric one, shikometabolin G (1), together with six known ones (6–10), were isolated from the methanol extract of Onosma paniculatum. Their structures were established based on the analysis of NMR and MS spectroscopic data. All of the compounds were evaluated for inhibitory effects on NO production in murine macrophage RAW 264.7 cells. Compounds 2, 3, 5, 6, 7, 8, and 10 displayed good activity on the inhibition of NO production (IC₅₀ = 0.4–16.5 µM), suggesting the potential property of anti-inflammation.

Key words

Boraginaceae - Onosma paniculatum - naphthoquinone - shikometabolins - anti-inflammation

Full Text

References

References
1 Binzet R. A new species of Onosma L. (Boraginaceae) from Anatolia. Turk J Botany 2016; 40: 194-200
2 Mehrabian AR, Sheidai M, Noormohammadi Z, Mozafarian V, Asrei Y. Palynological diversity in the genus Onosma L. (Boraginaceae) of Iran. Ann Biol Res 2012; 3: 3885-3893
3 Shu DZ. Onosma Linnaeus. Flora of China (Zhongguo Zhiwu Zhi). Beijing: Science Press; 1995: 15
4 Kumar N, Kumar R, Kishore K. Onosma L: A review of phytochemistry and ethnopharmacology. Pharmacogn Rev 2013; 7: 140-151
5 Wang L, Li F, Liu X, Chen B, Yu K, Wang MK. Meroterpenoids and a naphthoquinone from Arnebia euchroma and their cytotoxic activity. Planta Med 2015; 81: 320-326
6 Chen X, Yu L, Oppenheim J, Howard O. Cellular pharmacological study of shikonin derivatives. Phytother Res 2002; 16: 199-209
7 Chen X, Yang L, Zhang N, Turpin JA, Buckheit RW, Osterling C, Oppenheim J, Howard OM. Shikonin, a component of Chinese herbal medicine, inhibits chemokine receptor function and suppresses human immunodeficiency virus type 1. Antimicrob Agents Chemother 2003; 9: 2810-2816
8 Meselhy RM, Shigetoehi K, Koji T, Kusai A, Hattori M, Nambaa T. Shikometabolias A, B, C and D, novel dimeric napbthoquinooe metabolites obtained from shikonin by human intestinal bacteria. Tetrahedron Lett 1994; 35: 583-584
9 Yang YQ, Zhao DP, Yuan KL, Zhou GJ, Wang Y, Xiao YM, Wang CX, Xu JW, Yang W. Two new dimeric naphthoquinones with neuraminidase inhibitory activity from Lithospermum erythrorhizon . Nat Prod Res 2015; 29: 908-913
10 Mallavadhani UV, Prasad CV, Shrivastava S, Naidu VGM. Synthesis and anticancer activity of some novel 5,6-fused hybrids of juglone based 1,4-naphthoquinones. Eur J Med Chem 2014; 83: 84-91
11 Kimura Y, Shimada A, Nakajima H, Hamasaki T. Structures of naphthoquinones produced by the fungus, Fusarium sp., and their biological activity toward pollen germination. Agric Biol Chem 1988; 52: 1253-1259
12 Machida K, Matsuoka E, Kasahara T, Kikuchi M. Studies on the constituents of Juglans species. I. Structural determination of (4S)- and (4R)-4-hydroxy-α-tetralone derivatives from the fruit of Juglans mandshurica MAXIM var. sieboldiana MAKINO. Chem Pharm Bull 2005; 53: 934-937
13 Inoue K, Akaji M, Inouye H. Quinones and related compounds in higher plants. XXI. New findings on the proton and carbon-13 nuclear magnetic resonance spectra of shikonin. Chem Pharm Bull 1985; 33: 3993-3997
14 Tian H, Sun D, Dou G, Yuan D, Meng Z. Quantitative determination of β,β-dimethylacrylshikonin (DASK) in rat whole blood by liquid chromatography-tandem mass spectrometry with pre-column derivation and its pharmacokinetic application. Biomed Chromatogr 2009; 23: 365-370
15 Han J, Weng X, Bi K. Antioxidants from a Chinese medicinal herb – Lithospermum erythrorhizon . Food Chem 2008; 106: 2-10
16 Liu X, Jing YP, Shi YP. Bothriodumin, a shikonin derivative from Bothriospermum secundum Maxim. Pharmazie 2009; 64: 619-621
17 Kim JY, Jeong HJ, Park JY, Kim YM, Park SJ, Cho JK, Park KH, Ryu YB, Lee WS. Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases. Bioorg Med Chem 2012; 20: 1740-1748
18 Versiani MA, Diyabalanage T, Ratnayake R, Henrich CJ, Bates SE, Mcmahon JB, Gustafson KR. Flavonoids from eight tropical plant species that inhibit the multidrug resistance transporter ABCG2. J Nat Prod 2011; 74: 262-266

Supplementary Material

Supporting Information (PDF)