New spinosin derivatives from the seeds of Ziziphus mauritiana

Bin Wang; Hong-Tao Zhu; Dong Wang; Chong-Ren Yang; Min Xu; Ying-Jun Zhang

doi:10.1007/s13659-013-0028-5

. 2013 May 7;3(3):93–98. doi: 10.1007/s13659-013-0028-5

New spinosin derivatives from the seeds of Ziziphus mauritiana

Bin Wang ^128,²²⁸, Hong-Tao Zhu ¹²⁸, Dong Wang ¹²⁸, Chong-Ren Yang ¹²⁸, Min Xu ^128,^✉, Ying-Jun Zhang ^128,^✉

PMCID: PMC4131668

Abstract

Three new acylated flavonoid C-glycosides, 6‴-(-)-phaseoylspinosin (1), 6‴-(3″″,4″″,5″″-trimethoxyl)-(E)-cinnamoylspinosin (2), and 6‴-(4″″-O-β-D-gluco-pyranosyl)-benzoylspinosin (3), were isolated from the seeds of Ziziphus mauritiana (Rhamnaceae). A further 19 known compounds including eight spinosin analogues (4–11) were also isolated. Their structures were elucidated by means of spectroscopic analysis and chemical method. Among spinosin derivatives 1, 2, 4, 7, 8, and triterpenoid saponin 14, jujuboside A (14) displayed moderate acetylcholinesterase (AchE) inhibitory activity with an inhibition value of 46.2% at a concentration of 1 µM. graphic file with name 13659_2013_28_Article_Fig1_HTML.jpg

Electronic Supplementary Material

Supplementary material is available for this article at 10.1007/s13659-013-0028-5 and is accessible for authorized users.

Keywords: Ziziphus mauritiana, Rhamnaceae, seeds, spinosin derivatives, jujuboside A, acetylcholinesterase inhibitory

Electronic supplementary material

13659_2013_28_MOESM1_ESM.pdf^{(845.8KB, pdf)}

Supplementary material, approximately 846 KB.

Footnotes

This article is published with open access at Springerlink.com

Contributor Information

Min Xu, Email: xumin@mail.kib.ac.cn.

Ying-Jun Zhang, Email: zhangyj@mail.kib.ac.cn.

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

13659_2013_28_MOESM1_ESM.pdf^{(845.8KB, pdf)}

Supplementary material, approximately 846 KB.

[CR1] [1].Ji C J, Zeng G Z, Han J, He W J, Zhang Y M, Tan N H. Bioorg. Med. Chem. Lett. 2012;22:6377–6380. doi: 10.1016/j.bmcl.2012.08.074. [DOI] [PubMed] [Google Scholar]

[CR2] [2].Chen Y L, Zhou B K. In Chinese Flora. Beijing: Science Press; 1982. pp. 131–146. [Google Scholar]

[CR3] [3].Liu M J. Acta Hortic. Sin. 1999;26:302–308. [Google Scholar]

[CR4] [4].Cheng G, Bai Y J, Zhao Y Y, Tao J, Liu Y, Tu G Z, Ma L B, Liao N, Xu X J. Tetrahedron. 2000;56:8915–8920. doi: 10.1016/S0040-4020(00)00842-5. [DOI] [Google Scholar]

[CR5] [5].Zhang L, Xu Z L, Wu C F, Yang J Y, Kano Y, Yuan D. J. Asian. Nat. Prod. Res. 2012;14:121–128. doi: 10.1080/10286020.2011.637491. [DOI] [PubMed] [Google Scholar]

[CR6] [6].Xie Y Y, Xu Z L, Wang H, Kano Y, Yuan D. J. Asian. Nat. Prod. Res. 2011;13:1151–1157. doi: 10.1080/10286020.2011.623128. [DOI] [PubMed] [Google Scholar]

[CR7] [7].Tan N H, Zhou J. Chem. Rev. 2006;106:840–895. doi: 10.1021/cr040699h. [DOI] [PubMed] [Google Scholar]

[CR8] [8].Tschesche R, Wilhelm H, Fehlhaber H W. Tetrahedron Lett. 1972;26:2609–2612. doi: 10.1016/S0040-4039(01)84887-5. [DOI] [Google Scholar]

[CR9] [9].Tschesche R, Wilhelm H, Kauβmann E U, Eckhardt G. Justus Liebigs Ann. Chem. 1974. pp. 1694–1701. [Google Scholar]

[CR10] [10].Tschesche R, Hillebrand D, Wilhelm H, Ammermann E, Eckhardt G. Phytochemistry. 1977;16:1025–1028. doi: 10.1016/S0031-9422(00)86715-1. [DOI] [Google Scholar]

[CR11] [11].Jossang A, Zahir A, Diakite D. Phytochemistry. 1996;42:565–567. doi: 10.1016/0031-9422(95)00965-5. [DOI] [Google Scholar]

[CR12] [12].Panseeta P, Lomchoey K, Prabpai S, Kongsaeree P, Sukasamrarn A, Ruchiraeat S, Suksamrarn S. Phytochemistry. 2011;72:909–915. doi: 10.1016/j.phytochem.2011.03.003. [DOI] [PubMed] [Google Scholar]

[CR13] [13].Srivastava S K, Srivastava S D. Phytochemistry. 1979;18:1758–1759. doi: 10.1016/0031-9422(79)80210-1. [DOI] [Google Scholar]

[CR14] [14].Agarwal S K, Singh S S, Verma S, Kumar S. Indian J. Chem. B: Org. Chem. Incl. Med. Chem. 2000;39:872–874. [Google Scholar]

[CR15] [15].Krasutsky P A. Nat. Prod. Rep. 2006;23:919–942. doi: 10.1039/b606816b. [DOI] [PubMed] [Google Scholar]

[CR16] [16].Lee S S, Chen W C, Huang C F, Su Y. J. Nat. Prod. 1998;61:1343–1347. doi: 10.1021/np9800856. [DOI] [PubMed] [Google Scholar]

[CR17] [17].Lv T, Xu M, Wang D, Zhu H T, Yang C R, Zhang T T, Zhang Y J. Nat. Prod. Bioprospect. 2012;2:217–221. doi: 10.1007/s13659-012-0067-3. [DOI] [Google Scholar]

[CR18] [18].Xu M, Wang D, Zhang Y J, Yang C R. J. Nat. Prod. 2007;70:880–883. doi: 10.1021/np070012z. [DOI] [PubMed] [Google Scholar]

[CR19] [19].Xu M, Zhang M, Zhang Y J, Yang C R. Helv. Chim. Acta. 2009;92:321–327. doi: 10.1002/hlca.200800258. [DOI] [Google Scholar]

[CR20] [20].Tanaka Y, Sanada S. Shoyakugaku Zasshi. 1991;45:148–152. [Google Scholar]

[CR21] [21].Wu Y, He F, Pan Q, Shi Y, Min Z D, Liang J Y. Chem. Nat. Compd. 2011;47:369–372. doi: 10.1007/s10600-011-9936-y. [DOI] [Google Scholar]

[CR22] [22].Xie C, Veitch N C, Houghton P J, Simmonds M S J. Chem. Pharm. Bull. 2003;51:1204–1207. doi: 10.1248/cpb.51.1204. [DOI] [PubMed] [Google Scholar]

[CR23] [23].Kitajima J, Kimizuka K, Arai M, Tanaka Y. Chem. Pharm. Bull. 1998;46:1647–1649. doi: 10.1248/cpb.46.1647. [DOI] [Google Scholar]

[CR24] [24].Renault J H, Ghedira K, Thepenier P, Lavaud C, Zeches-Hanrot M, Men-Olivier L L. Phytochemistry. 1997;44:1321–1327. doi: 10.1016/S0031-9422(96)00721-2. [DOI] [PubMed] [Google Scholar]

[CR25] [25].Schumacher B, Scholle S, Holzl J, Khudeir N, Hess S, Muller C E. J. Nat. Prod. 2002;65:1479–1485. doi: 10.1021/np010464q. [DOI] [PubMed] [Google Scholar]

[CR26] [26].Deyama T, Ikawa T, Kitagawa S, Nishibe S. Chem. Pharm. Bull. 1987;35:1785–1789. doi: 10.1248/cpb.35.1785. [DOI] [Google Scholar]

[CR27] [27].Ho J C, Chen C M, Row L C. J. Chin. Chem. Soc. 2003;50:1271–1274. doi: 10.1002/jccs.200300183. [DOI] [Google Scholar]

[CR28] [28].Wang C Z, Jia Z J. Phytochemistry. 1997;45:159–166. doi: 10.1016/S0031-9422(96)00770-4. [DOI] [Google Scholar]

[CR29] [29].Masataka S, Masao K. Heterocycles. 1993;36:117–121. doi: 10.3987/COM-92-6187. [DOI] [Google Scholar]

[CR30] [30].Han B H, Park M H, Han Y N. Arch. Pharm. Res. 1989;12:263–268. doi: 10.1007/BF02911058. [DOI] [Google Scholar]

[CR31] [31].Aldrich Library of 13C and 1H FT NMR Spectra. 1992;3:143. [Google Scholar]

[CR32] [32].Hirai N, Kondo S, Ohigashi H. Biosci. Biotechnol. Biochem. 2003;67:2408–2415. doi: 10.1271/bbb.67.2408. [DOI] [PubMed] [Google Scholar]

[CR33] [33].Kitahara T, Touhara K, Watanabe H, Mori K. Tetrahedron. 1989;45:6387–6400. doi: 10.1016/S0040-4020(01)89516-8. [DOI] [Google Scholar]

[CR34] [34].Payo-Hill A L, Domingueza R S, Suareza M O, Batista-Baeza M, Castro Velez H T, Rastrelli L, Aquinoc R. Phytochemistry. 2000;54:927–932. doi: 10.1016/S0031-9422(00)00087-X. [DOI] [PubMed] [Google Scholar]

[CR35] [35].Ellman G L, Courtney K D, Andres V J, Featherstone R M. Biochem Pharmacol. 1961;7:88–95. doi: 10.1016/0006-2952(61)90145-9. [DOI] [PubMed] [Google Scholar]

PERMALINK

New spinosin derivatives from the seeds of Ziziphus mauritiana

Bin Wang

Hong-Tao Zhu

Dong Wang

Chong-Ren Yang

Min Xu

Ying-Jun Zhang

Abstract

Electronic Supplementary Material

Electronic supplementary material

Footnotes

Contributor Information

References

Associated Data

Supplementary Materials

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PERMALINK

New spinosin derivatives from the seeds of Ziziphus mauritiana

Bin Wang

Hong-Tao Zhu

Dong Wang

Chong-Ren Yang

Min Xu

Ying-Jun Zhang

Abstract

Electronic Supplementary Material

Electronic supplementary material

Footnotes

Contributor Information

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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