Two Novel Guaiane Sesquiterpenes from the Whole Plant of Youngia japonica

Ji Young Lee; Mi-Ran Cha; Mi Ri Kim; Kwangho Lee; Sang-Un Choi; Shi Yong Ryu

doi:10.1055/s-0035-1557794

Planta Medica Letters, Inhaltsverzeichnis

Planta Medica Letters 2015; 2(01): e31-e34
DOI: 10.1055/s-0035-1557794

Letter

Georg Thieme Verlag KG Stuttgart · New York

Two Novel Guaiane Sesquiterpenes from the Whole Plant of Youngia japonica

Ji Young Lee

¹Research Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, Daejeon, Korea

²Graduate School of New Drug Discovery and Development, Chungnam National University, Daejeon, Korea

,

Mi-Ran Cha

¹Research Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, Daejeon, Korea

,

Mi Ri Kim

¹Research Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, Daejeon, Korea

,

Kwangho Lee

¹Research Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, Daejeon, Korea

,

Sang-Un Choi

¹Research Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, Daejeon, Korea

,

Shi Yong Ryu

¹Research Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, Daejeon, Korea

²Graduate School of New Drug Discovery and Development, Chungnam National University, Daejeon, Korea

› Institutsangaben

Abstract

Two new guaiane-type sesquiterpenes (1 and 2) together with eight related sesquiterpenoidal constituents (3–10) were isolated from the whole extract of Youngia japonica. The chemical structures of 1–10 were established by spectroscopic analyses as 4-epi-isolipidiol (1), 4′-p-hydroxyphenylacetyl crepiside E (2), isolipidiol (3), isoambeboin (4), grosheimin (5), annuionone D (6), loliolide (7), youngiajaponicoside A (8), crepiside H (9), and crepiside E (10), respectively. Among the isolated components, 5 exhibited a significant inhibitory effect on the proliferation of cultured human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT15).

Key words

Youngia japonica - Asteraceae - guaiane sesquiterpene - cytotoxicity

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Referenzen

References
1 Kim IS, Seo BB, Song SD, Park JH, Lee MO, Kim JS. The identification of unrecorded subspecies of Youngia japonica . Kor J Plant Tax 2000; 30: 55-73
2 Jang DS, Ha TJ, Choi SU, Nam SH, Park KH, Yang MS. Isolation of isoamberboin and isolipidiol from whole plants of Youngia japonica (L.) DC. Kor J Pharmacogn 2000; 31: 306-309
3 Lee WB, Kwon HC, Yi JH, Choi SU, Lee KR. A new cytotoxic triterpene hydroperoxide from the aerial part of Youngia japonica . Yakhak Hoeji 2002; 46: 1-5
4 Dat NT, Cai XF, Bae KH, Kim YH. Terpenoid constituents from Youngia koidzumiana . Nat Prod Sci 2002; 8: 55-57
5 Adegawa S, Miyase T, Fukushima S. Sesquiterpene glycosides from Youngia denticulata (Houtt.) Kitam. Chem Pharm Bull 1986; 34: 3769-3773
6 Arai Y, Wama M, Ageta H. Composite constituents: aliphatics and triterpenoids isolated from the aerial parts of Youngia denticulata . Yakugaku Zasshi 1982; 102: 1089-1091
7 Jo YM, Suh JY, Bae SJ, Jung JH, Im KS. Sesquiterpene lactones from the roots of Ixeris sonchifolia . Nat Prod Sci 2005; 11: 55-57
8 Srivastava RP, Proksch P, Wray V. Toxicity and antifeedant activity of a sesquiterpene lactone from Encelia against Spodoptera littoralis . Phytochmistry 1990; 29: 3445-3448
9 Ahn EM, Bang MH, Song MC, Park MH, Kim HY, Kwon BM, Baek NI. Cytotoxic and ACAT-inhibitory sesquiterpene lactones from the root of Ixeris dentata forma albiflora . Arch Pharm Res 2006; 29: 937-941
10 Gonzalez AG, Garcia BM, Breton J. Terpenoids of compositae. X. Structure of grosshemin, lipidiol, and isolipidiol. Lactones of Amberboa lipii and their stereochemistry. Anales de Quimica 1970; 66: 799-811
11 Cha MR, Choi YH, Choi CW, Yoo DS, Kim YS, Choi SU, Kim YH, Ryu SY. New guaiane sesquiterpene lactones from Ixeris dentata . Planta Med 2011; 77: 380-382
12 Fazylova AS, Turdybekov KM, Kadirberlina GM, Rakhimova BB, Adekenov SM. Molecular structure of crepidioside a and isolipidiol from Crepis multicaulis . Chem Nat Cmpd 2000; 36: 177-180
13 Jang DS, Ha TJ, Choi SU, Nam SH, Park KH, Yang MS. Isolation of isoamberboin and isolipidiol from whole plants of Youngia japonica (L.) DC. Kor J Pharmacogn 2000; 31: 306-309
14 Oksuz S, Ulubelen A, Aynechi Y, Wagner H. A guaianolide from Centaurea behen . Phytochemistry 1982; 21: 2747-2749
15 Xie XD, Niu YF, Lai PX, Row KH. Sesquiterpenoids and other constituents from Senecio argunensis . Chem Pharm Bull 2010; 58: 991-994
16 He Z, Zhang A, Ding L, Lei X, Sun J, Zhang L. Chemical composition of the green alga Codium divaricatum Holmes. Fitoterapia 2010; 81: 1125-1128
17 Chen WL, Liu QF, Wang J, Zou J, Meng DH, Zuo JP, Zhu XZ, Zhao WM. New guaiane, megastigmane and eudesmane-type sesquiterpenoids and anti-inflammatory constituents from Youngia Japonica . Planta Med 2006; 72: 143-150
18 Miyase T, Yamada M, Fukushima S. Studies on sesquiterpene glycoside from Prenanthes acerifolia BENTH. Chem Pharm Bull 1987; 35: 1969-1974
19 Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990; 82: 1107-1112

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