Chemical study of four samples of Ligularia brassicoides collected in Sichuan Province of China afforded 18 compounds, five of which were new. LC-MS profiles were somehow similar to each other, although the compound ratio was slightly different. One of the new compound was a Diels-Alder adduct between franoeremophilan-10β-ol and methacrylic acid.
KurodaC, HanaiR, NaganoH, ToriM, GongX. (2012) Diversity of furanoeremophilanes in major Ligularia species in the Hengduan mountains. Natural Product Communications, 7, 539–548.
2.
LiuSW. (1989) Flora Reipublicae Popularis Sinicae, Science Press, Beijing, Vol. 77;
3.
LiuS, IllarionovaID. (2011) Flora of China, Science Press, Beijing, and Missouri Botanical Garden Press, St. Louis, Vol. 20–21.
4.
SaitoY, SasakiY, OhsakiA, OkamotoY, GongX, KurodaC, ToriM. (2014) Structures of six new compounds from Ligularia brassicoides. Tetrahedron, 70, 9726–9730.
5.
BohlmannF, Le VanN. (1978) Neues sesqui- und diterpene aus Bedfordia salicina, Phytochemistry, 17, 1173–1178.
6.
NaganoH, KurodaC, MoriyamaY, TsuyukiT, TakahashiT. (1982) Mass spectra of furanoeremophilane derivatives. Bulletin of the Chemical Society of Japan, 55, 1221–1227.
7.
TadaM, TanahashiY, MoriyamaY, TakahashiT. (1972) Skeletal rearrangement of furanoeremophilane-6β,10β-diol into farfugin A and farfugin B. Tetrahedron Letters, 5255–5258.
8.
ToriM, WatanabeA, MatsuoS, OkamotoY, TachikawaK, TakaokaS, GongX, KurodaC, HanaiR. (2008) Diversity of Ligularia kanaitzensis in sesquiterpenoid composition and neutral DNA sequences. Tetrahedron, 64, 4486–4495.
9.
NayaK, NogiN, MoriyamaY, TakashinaH, ImagawaT. (1977) The photosensitized oxygenation of furanoeremophilanes. II. The preparation and stereochemistry of the isomeric hydroperoxides and the corresponding lactones from furanofukinin and furanoeremophilane. Bulletin of the Chemical Society of Japan, 50, 3002–3006.
10.
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.
11.
NayaK, KanazawaR, SawadaM. (1975) The photosensitized oxygenation of furanoeremophilanes. I. The isomeric hydroperoxides from petasalbin and their transformations to lactones. Bulletin of the Chemical Society of Japan, 48, 3220–3225.
12.
TadaM, MoriyamaY, TanahashiY, TakahashiT, FukuyamaM, SatoK. (1971) New furanosesquiterpenes from Ligularia japonica. Furanoeremophilane-6β,10β-diol, 10β-hydroxy-6β-methoxyfuranoeremophilane, and 10β-hydroxyfuranoeremophilan-6β-yl 2′ξ-methylbutanoate, Tetrahedron Letters, 4007–4010.
13.
MashEA, FrylingJA. (1987) Homochiral ketals in organic synthesis. Enantioselective synthesis of (+)-β-eudesmol, Journal of Organic Chemistry, 52, 3000–3003.
14.
ToyotaM, SaitoT, AsakawaY. (1999) The absolute configuration of eudesmane-type sequiterpenoids found in the Japanese liverwort Chiloscyphus polyanthus, Phytochemistry, 51, 913–920.
15.
ItokawaH, MoritaH, WatanabeK, MihashiS, IitakaY. (1985) Agarofuran-, eudesmane- and eremophilane-type sesquiterpenoids from Alpinia japonica (Thunb.)Miq, Chemical and Pharmaceutical Bulletin, 33, 1148–1153.
16.
MassiotP, NuzillardJM, Le Men-OlivierL, AclinouP, BenkouiderA, KhelifaA. (1990) Eremophilenolides from Hertia cheirifolia, Phytochemistry, 29, 2207–2210.
17.
HafezS, JakupovicJ, BohlmannF, SargTM, OmarAA. (1989) Transformation products of furoeremophilanes and other constituents from Euryops arabicus, Phytochemistry, 29, 843–847.
18.
ShirahataK, KatoT, KitaharaY. (1969) Constituents of genus Petasites—IV: Bakkenolide-A, a sesquiterpene of novel carbon skeleton, Tetrahedron, 25, 3179–3191.
19.
SheldrickGM. (1997) SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany.