From the roots of Ligularia cymbulifera collected in Yunnan Province, China, two new eremophilane-type sesquiterpenoids (1 and 2) together with ten known compounds (3–12) were obtained through the precise chemical component elucidation. The structure determination was mainly carried out with 1D and 2D NMR data.
ShimizuA., HanaiR., OkamotoY., ToriM., YuJ.J., GongX., KurodaC. (2016) Chemical constituents in hybrids of Ligularia tongolensis and L. cymbulifera: Chemical introgression in L. tongolensis. Chemistry and Biodiversity, 13, 837–844.
2.
KurodaC., HanaiR., ToriM., OkamotoY., SaitoY., NaganoH., OhsakiA., HirotaH., KawaharaT., GongX. (2014) Diversity in furanoeremophilane composition produced by Ligularia species (Asteraceae) in the Hengduan Mountains area of China. Journal of Synthetic Organic Chemistry, Japan, 72, 717–725.
3.
KurodaC., HanaiR., NaganoH., ToriM., GongX. (2012) Diversity of furanoeremophilanes in major Ligularia species in the Hengduan Mountains. Natural Product Communications, 7, 539–548.
4.
(a) HirotaH., HoriguchiY., KawaiiS., HanaiR., GongX., KurodaC. (2014) The first isolation of furanoeremophilane from Ligularia nelumbifolia. Natural Product Communications, 9, 325–327; (b) Hirota H, Horiguchi Y, Kawaii S, Kuroda C, Hanai R, Gong X. (2012) Four new bisabolane-type sesquiterpenes from Ligularia lankongensis. Natural Product Communications, 7, 451–454; (c) Onuki H, Yamazaki M, Nakamura A, Hanai R, Kuroda C, Gong X, Shen Y, Hirota H. (2008) Chemical constituents and diversity of Ligularia lankongensis in Yunnan Province of China. Journal of Natural Products, 71, 520–524.
5.
HanaiR., GongX., ToriM., KondoS., OtoseK., OkamotoY., NishihamaT., MurotaA., ShenY., WuS., KurodaC. (2005) Chemical and genetic Study of Ligularia tongolensis, Ligularia cymbulifera, and Ligularia atroviolacea in the Hengduan Mountains of China. Bulletin of Chemical Society of Japan, 78, 1302–1308.
6.
(a) WuY-X, ChenY-J, LiuC-M, GaoK. (2012) Four new sesquiterpenoids from Ligularia cymbulifera. Journal of Asian Natural Products Research, 14, 1130–1136; (b) Liu C-M, Wang H-X, Wei S-L, Gao K. (2008) Pyrrolizidine alkaloids and bisabolane sesquiterpenes from the roots of Ligularia cymbulifera. Helvetica Chimica Acta, 91, 308–316; (c) Liu C-M, Fei D-Q, Wu Q-H, Gao K. (2006) Bisabolane sesquiterpenes from the roots of Ligularia cymbulifera. Journal of Natural Products, 69, 695–699.
7.
JenningsP.W., ReederS.K., HurleyJ.C., CaughlamC.N., SmithG.D. (1974) Isolation and structure determination of one of the toxic constituents from Tetradymia glabrata. Journal of Organic Chemistry, 39, 3392–3398.
8.
IshiiH., TozyoT., MinatoH. (1966) Studies on sesquiterpenoids. Part XIII. Components of the root of Ligularia fischeri Turcz. Journal of the Chemical Society C, 1545–1548.
9.
BohlmannF., KnollK-H. (1978) Weitere Furanoeremophilane aus Othonna-arten. Phytochemistry, 17, 461–465.
10.
BohlmannF., JakupovicJ., MohammadiD. (1984) Shikimic acid derivative from Senecio hieracioides. Journal of Natural Products, 47, 718–720.
11.
MassiotG., NuzillardJ-M, Le Men-OlivierL., AclinouP., BenkouiderA., KhelifaA. (1990) Eremophilenolides from Hertia cheirfolia. Phytochemistry, 29, 2207–2210.
12.
LiS., HuangH., LiuJ., SongT., WuaK., HanY., XiaM. (2013) Two new sesquiterpenes from Ligularia dictyoneura. Phytochemistry Letters, 6, 315–317.
13.
HanY.F., PanJ., GaoK., JiaZ.J. (2005) Sesquiterpenes, nortriterpenes and other constituents from Ligularia tongolensis. Chemical and Pharmceutical Bulletin, 53, 1338–1341.
14.
LiuX., LiJ., LuoJ., LiD., ZhangH., GuoZ. (2016) A new sesquiterpene from Ligularia fischeri. Chemistry of Natural Compounds, 52, 642–646.
TaniguchiM., NakashimaK., OkamotoY., GongX., KurodaC., ToriM. (2015) Constituents of Ligularia brassicoides collected in China: A new Diels-Alder adduct of eremophilan-10p-ol and methacrylic acid. Natural Product Communications, 10, 827–830.
17.
(a) IidaK., MitaniM., KurodaC. (2007) Fixation of natural furanoeremophilane by Diels-Alder reaction. Bulletin of the Chemical Society of Japan, 80, 966–971; (b) Torihata A, Kuroda C. (2008) Reaction of furanoeremophilans with pyridoxal. Natural Product Communications, 3, 1659–1662.