Journal List > Nat Prod Sci > v.23(2) > 1060698

Kwon, Kim, Kim, and Chun: Acetylcholinesterase Inhibitors from Angelica polymorpha Stem

Abstract

Fourteen compounds were isolated from the stem of Angelica polymorpha. On the basis of spectral data, these compounds were identified as isoimperatorin (1), phellopterin (2), bergapten (3), xanthyletin (4), cnidilin (5), geijerine (6), (−)-3'-acetyl hamaudol (7), 7-demethylsuberosine (8), dehydrogeijerin (9), (–)-hamaudol (10), (+)-visamminol (11), divaricatol (12), scopoletin (13), and decursidate (14), respectively. Among them, compounds 4 – 6, 8, 9, 13, and 14 were isolated for the first time from A. polymorpha. Dehydrogeijerin (6) and geijerin (9) were isolated for the first time from genus Angelica. All isolates tested for inhibitory activity against acetylcholinesterae. Compounds 1 to 13 showed acetylcholinesterase inhibitory activity with IC50 values ranging from 1.4 to 37.5 µM.

References

(1). Lee W. T.Standard illustrations of Korean plants; Academy Pub. Co.: Seoul,. 1996. , p. 254.
(2). Editorial Committee of Zhong Hua Ben Cao of State Administration of Traditional Chinese Medicine of People's Republic of China. Zhong Hua Ben Cao; Shanghai Science and Technology Press: Shanghai,. 1999. 892–893.
(3). Yang Y.., Zhang Y.., Ren F. X.., Yu N. J.., Xu R.., Zhao Y. M.Yao Xue Xue Bao,. 2013. 48:718–722.
(4). Yang S. J.., Yao Q. Q.., Li Y. N.., Chen X. X.., Cui S. X.., Bai S. Y.., Wang F. L. J.Asian Nat. Prod. Res. 2012. 14:76–79.
(5). Dan F. J.., Chu L. J.., Tian Y.., Dong J. X.., Cai Z. J.Shizhen Guoyi Guoyao. 2011. 22:299–300.
(6). Yang Y.., Yu N.., Zhang Y.., Ren F.., Zhang A.., Zhao Y.Zhongguo Yaoxue Zazhi. 2010. 45:1320–1323.
(7). Yang Y.., Yu N.., Liang F.., Zhang Y.., Ren F. X.., Zhang A.., Zhao Y.Pharm. J. Chin. PLA. 2010. 26:189–191.
(8). Han S.., Bai S. Y.., Yang S. J. J.Jining Med. Univ. 2010. 33:13–14.
(9). Li Y.., Yang S.., Bai S.Zhongguo Zhong Yao Za Zhi. 2009. 34:854–857.
(10). Pachaly P.., Kroll-Horstmann A.., Sin K. S.Pharmazie. 2000. 55:777–778.
(11). Coyle J. T.., Price D. L.., DeLong M. R.Science. 1983. 219:1184–1190.
(12). Mukherjoo P. K.., Kumar V.., Mal M.., Houghton P. J.Phytomedicine. 2007. 14:289–300.
(13). Houghton P. J.., Ren Y.., Howes M. J.Nat. Prod. Rep. 2006. 23:181–199.
(14). Anand P.., Singh B.Arch. Pharm. Res. 2013. 36:375–399.
(15). Ellman G. L.., Courtney K. D.., Andres Jr. V.., Feather-Stone R. M.Biochem. Pharmacol. 1961. 7:88–95.
(16). Kim S. J.., Chin Y. W.., Yoon K. D.., Ryu M. Y.., Yang M. H.., Lee J. H.., Kim J. W.Kor. J. Pharmacogn. 2008. 39:357–364.
(17). Wu T. S.., Kuoh C. S.., Furukawa H.Chem. Pharm. Bull. 1983. 31:895–900.
(18). Abreu V. G. C.., Silva M. C.., Magalhâes R. M.., Pilo-Veloso D.., Xavier I. F. S.., Oliveira P. M.., Alcântra A. F. C.Acta Amazonica. 2010. 40:711–718.
(19). Lee K. H.., Soine T. O. J.Pharm. Sci. 1969. 58:675–681.
(20). Frank K.., Porzel A.., Masaoud M.., Adam G.., Schmidt J.Phytochemistry. 2001. 56:611–621.
(21). Fujioka T.., Furumi K.., Fujii H.., Okabe H.., Mihashi K.., Nakano Y.., Matsunaga H.., Katano M.., Mori M.Chem. Pharm. Bull. 1999. 47:96–100.
(22). An R. B.., Park B. Y.., Kim J. H.., Kwon O. K.., Lee J. K.., Min B. S.., Ahn K. S.., Oh S. R.., Lee H. K.Nat. Prod. Sci. 2005. 11:79–84.
(23). Park H. Y.., Kwon S. B.., Heo N. K.., Chun W.., Kim M. J.., Kwon Y. J.Korean Soc. Appl. Biol. Chem. 2011. 54:194–199.
(24). Skalicak-Wo niak K.., Mroczek T.., Garrard I.., G owniak K. J.Sep. Sci. 2012. 35:790–797.
(25). Wang L.., Yu M. M.., Chi Y. Q.., Ouyang W. B.., Zang Z.., Zhao Y.Zhongguo Zhong Yao Za Zhi,. 2014. 39:3969–3973.
(26). Kong L. Y.., Yao N. H.Chin. Chem. Lett. 2000. 11:315–318.
(27). Lee H. K.., Oh S. R.., Kwon O. K.., Ahn K. S.., Lee J.., Kim J. C.., Min B. S.., Joung H.Phytother. Res. 2007. 21:406–409.
(28). Steck W.., Mazurek M.Lloydia. 1972. 35:418–439.
(29). Cairns N.., Harwood L. M.., Astles D. P.Tetrahedron. 1992. 36:7581–7590.
(30). Domínguez X. A.., Cano G.., Luna I.., Dieck A.Phytochemistry,. 1977. 16:1096.
(31). Ritchie E.., Taylor W. C.., Young L. M.Aust. J. Chem. 1968. 21:1381–1382.
(32). Lahey F. N.., Wluka D. J.Aust. J. Chem. 1955. 8:125–128.
(33). Kim, D. K; Lim J. P.., Yang J. H.., Eom D. O.., Eun J. S.., Leem K. H.Arch. Pharm. Res. 2002. 25:856–859.
(34). Lee J. H.., Lee K. T.., Yang J. H.., Baek N. I.., Kim D. K.Arch. Pharm. Res. 2004. 27:53–56.
(35). Kang S. Y.., Lee K. Y.., Sung S. H.., Park M. J.., Kim Y. C. J.Nat. Prod. 2001. 64:683–685.

Fig. 1.
Structures of 1 – 14.
nps-23-97f1.tif
Table 1.
Acetylcholinesterase inhibitory activity of compounds 1 – 14
Tested compounds IC501) (µg/ml) IC50 (µM)
1 7.7 28.5
2 1.3 4.0
3 0.3 1.4
4 2.0 8.8
5 1.9 6.3
6 2.5 9.7
7 4.0 12.6
8 2.0 8.7
9 2.7 10.4
10 6.9 23.2
11 2.4 8.7
12 4.3 12.9
13 7.2 37.5
14 > 100
Galanthamine-hydrobromide2) 0.3 0.8

1) The inhibitory activity dose that reduced 50% of aceylcho-lineseterase activity and expressed as mean of two different experiments.

2) A positive control.

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