Two new dimeric naphthoquinones with neuraminidase inhibitory activity from Lithospermum erythrorhizon

Natural Product Research

Volumn 29, Issue 10, 2015, Pages 908-913

  Yang, Yanqin ^a,b   Zhao, Dapeng ^c   Yuan, Kailong ^b   Zhou, Guojun ^b   Wang, Yu ^a   Xiao, Yanmeng ^a   Wang, Chenxu ^a   Xu, Jingwei ^a   Yang, Wei ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b China Tobacco Zhejiang Industrial Co Ltd   (China)

^c Changchun Institute of Biological Products Co Ltd   (China)

Author keywords

dimeric naphthoquinone; Lithospermum erythrorhizon; neuraminidase inhibitory

Indexed keywords

NAPHTHOQUINONE; PLANT EXTRACT; QUERCETIN; SHIKOMETABOLIN A; SHIKOMETABOLIN E; SHIKOMETABOLIN F; SIALIDASE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; ENZYME INHIBITOR;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; LITHOSPERMUM; LITHOSPERMUM ERYTHRORHIZON; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET RADIATION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; PLANT ROOT;

LITHOSPERMUM ERYTHRORHIZON;

ENZYME INHIBITORS; LITHOSPERMUM; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NAPHTHOQUINONES; NEURAMINIDASE; PLANT ROOTS;

EID: 84928677872     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786419.2014.957695     Document Type: Article

References (32)

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2. Chang MJ, Huang HC, Chang HC, Chang TM. 2008. Cosmetic formulations containing Lithospermum erythrorhizon root extract show moisturizing effects on human skin. Arch Dermatol Res. 300: 317-323.
3. Cho MH, Paik YS, Hahn TR. 1999. Propionylshikonin from the roots of Lithospermum erythrorhizon. Arch Pharmacal Res. 22: 414-416.
4. Graikou K, Baranek KS, Pietrosiuk A, Damianakos H, Jeziorek M, Chinou I. 2011. Chemical analysis of Lithospermum canescens (Michx.) Lehm. hairy roots through TLC, CC, GC-MS, ESI-MS, and NMR methods. Acta Chromatogr. 23: 353-363.
5. Gwon SY, Ahn JY, Chung CH, Moon B, Ha TY. 2012. Lithospermum erythrorhizon suppresses high-fat diet-induced obesity, and acetylshikonin, a main compound of Lithospermum erythrorhizon, inhibits adipocyte differentiation. J Agric Food Chem. 12: 9089-9096.
6. Han H, Weng X, Bi K. 2008. Antioxidants from a Chinese medicinal herb-Lithospermum erythrorhizon. Food Chem. 106: 2-10.
7. Ito Y, Onobori K, Yamazaki T, Kawamura Y. 2011. Tigloylshikonin, a new minor shikonin derivative, from the roots and the commercial root extract of Lithospermum erythrorhizon. Chem Pharm Bull. 59: 117-119.
8. Li MY, Xu ZT, Zhu CL, Wang J. 2012. Effect of different derivatives of Shikonin from Lithospermum erythrorhizon against the pathogenic dental bacteria. Curr Pharm Anal. 8: 255-260.
9. Lu L, Qin A, Huang H, Zhou P, Zhang C, Liu N, Li S, Wen G, Zhang C, Dong W., et al. 2011. Shikonin extracted from medicinal Chinese herbs exerts anti-inflammatory effect via proteasome inhibition. Eur J Pharmacol. 658: 242-247.
10. Meselhy MR, Kadota S, Tsubono K, Kusai A, Hattori M, Namba T. 1994. Shikometabolins A, B, C and D, novel dimeric naphthoquinone metabolites obtained from shikonin by human intestinal bacteria. Tetrahedron Lett. 35: 583-586.
11. Syklowska-Baranek K, Pietrosiuk A, Naliwajski MR, Kawiak A, Jeziorek M, Wyderska S, Lojkowska E, Chinou I. 2012. Effect of l -phenylalanine on PAL activity and production of naphthoquinone pigments in suspension cultures of Arnebia euchroma (Royle) Johnst. In Vitro Cell Dev Biol: Plant. 48: 555-564.
12. Tian L, Wang Z, Wu H, Wang S, Wang Y, Wang Y, Xu J, Wang L, Qi F, Fang M., et al. 2011. Evaluation of the anti-neuraminidase activity of the traditional Chinese medicines and determination of the anti-influenza A virus effects of the neuraminidase inhibitory TCMs in vitro and in vivo. J Ethnopharmacol. 137: 534-542.
13. Weng XC, Xiang GQ, Jiang AL, Liu YP, Wu LL, Dong XW, Duan S. 2000. Antioxidant properties of components extracted from puccoon (Lithospermum erythrorhizon Sieb. et Zucc.). Food Chem. 69: 143-146.
14. Yang H, Zhou P, Huang H, Chen D, Ma N, Cui QC, Shen S, Dong W, Zhang X, Lian W., et al. 2009. Shikonin exerts antitumor activity via proteasome inhibition and cell death induction in vitro and in vivo. Int J Cancer. 124: 2450-2459.
15. Yin SY, Peng AP, Huang LT, Wang YT, Lan CW, Yang NS. 2013. The phytochemical shikonin stimulates epithelial-mesenchymal transition (EMT) in skin wound healing. J Evidence-Based Complementary Altern Med. 2013.
16. Zhao XP, Jin YC, Zeng X, Zhang BL, Zhang YF. 2011. Screening and identifying of nephrotoxic compounds in Lithospermum erythrorhizon using live-cell fluorescence imaging and liquid chromatography coupled with tandem mass spectrometry. Chem Res Chin Univ. 27: 562-565.
17. Andujar I, Recio MC, Giner RM, Rios JL. 2013. Traditional Chinese medicine remedy to jury: the pharmacological basis for the use of shikonin as an anticancer therapy. Curr Med Chem. 20:2892-2898.
18. Chang MJ, Huang HC, Chang HC, Chang TM. 2008. Cosmetic formulations containing Lithospermum erythrorhizon root extract show moisturizing effects on human skin. Arch Dermatol Res. 300:317-323.
19. Cho MH, Paik YS, Hahn TR. 1999. Propionylshikonin from the roots of Lithospermum erythrorhizon. Arch Pharmacal Res. 22:414-416.
20. Graikou K, Baranek KS, Pietrosiuk A, Damianakos H, Jeziorek M, Chinou I. 2011. Chemical analysis of Lithospermum canescens (Michx.) Lehm. hairy roots through TLC, CC, GC-MS, ESI-MS, and NMR methods. Acta Chromatogr. 23:353-363.
21. Gwon SY, Ahn JY, Chung CH, Moon B, Ha TY. 2012. Lithospermum erythrorhizon suppresses high-fat diet-induced obesity, and acetylshikonin, a main compound of Lithospermum erythrorhizon, inhibits adipocyte differentiation. J Agric Food Chem. 12:9089-9096.
22. Han H, Weng X, Bi K. 2008. Antioxidants from a Chinese medicinal herb-Lithospermum erythrorhizon. Food Chem. 106:2-10.
23. Ito Y, Onobori K, Yamazaki T, Kawamura Y. 2011. Tigloylshikonin, a new minor shikonin derivative, from the roots and the commercial root extract of Lithospermum erythrorhizon. Chem Pharm Bull. 59:117-119.
24. Li MY, Xu ZT, Zhu CL, Wang J. 2012. Effect of different derivatives of Shikonin from Lithospermum erythrorhizon against the pathogenic dental bacteria. Curr Pharm Anal. 8:255-260.
25. Lu L, Qin A, Huang H, Zhou P, Zhang C, Liu N, Li S, Wen G, Zhang C, Dong W, et al. 2011. Shikonin extracted from medicinal Chinese herbs exerts anti-inflammatory effect via proteasome inhibition. Eur J Pharmacol. 658:242-247.
26. Meselhy MR, Kadota S, Tsubono K, Kusai A, Hattori M, Namba T. 1994. Shikometabolins A, B, C and D, novel dimeric naphthoquinone metabolites obtained from shikonin by human intestinal bacteria. Tetrahedron Lett. 35:583-586.
27. Syklowska-Baranek K, Pietrosiuk A, Naliwajski MR, Kawiak A, Jeziorek M, Wyderska S, Lojkowska E, Chinou I. 2012. Effect of L-phenylalanine on PAL activity and production of naphthoquinone pigments in suspension cultures of Arnebia euchroma (Royle) Johnst. In Vitro Cell Dev Biol: Plant. 48:555-564.
28. Tian L, Wang Z, Wu H, Wang S, Wang Y, Wang Y, Xu J, Wang L, Qi F, Fang M, et al. 2011. Evaluation of the antineuraminidase activity of the traditional Chinese medicines and determination of the anti-influenza A virus effects of the neuraminidase inhibitory TCMs in vitro and in vivo. J Ethnopharmacol. 137:534-542.
29. Weng XC, Xiang GQ, Jiang AL, Liu YP, Wu LL, Dong XW, Duan S. 2000. Antioxidant properties of components extracted from puccoon (Lithospermum erythrorhizon Sieb. et Zucc.). Food Chem. 69:143-146.
30. Yang H, Zhou P, Huang H, Chen D, Ma N, Cui QC, Shen S, Dong W, Zhang X, Lian W, et al. 2009. Shikonin exerts antitumor activity via proteasome inhibition and cell death induction in vitro and in vivo. Int J Cancer. 124:2450-2459.
31. Yin SY, Peng AP, Huang LT, Wang YT, Lan CW, Yang NS. 2013. The phytochemical shikonin stimulates epithelial-mesenchymal transition (EMT) in skin wound healing. J Evidence-Based Complementary Altern Med. 2013.
32. Zhao XP, Jin YC, Zeng X, Zhang BL, Zhang YF. 2011. Screening and identifying of nephrotoxic compounds in Lithospermum erythrorhizon using live-cell fluorescence imaging and liquid chromatography coupled with tandem mass spectrometry. Chem Res Chin Univ. 27:562-565.