Ligularol (1), a furanoeremophilane, was isolated together with eremophil-1(10)-en-11-ol (2) from one of eight collected samples of Ligularia nelumbifolia and L. kongkalingensis, a closely related species. It is proposed that the ability to produce the furanoeremophilane has been acquired through hybridization.
KurodaC., HanaiR., NaganoH., ToriM., GongX. (2012) Diversity of furanoeremophilanes in major Ligularia species in the Hengduan Mountains. Natural Product Communications, 7, 539–548.
2.
(a) ToriM., HondaK., NakamizoH., OkamotoY., SakaokuM., TakaokaS., GongX., ShenY., KurodaC., HanaiR. (2006) Chemical constituents of Ligularia virgaurea and its diversity in southwestern Sichuan of China. Tetrahedron, 62, 4988–4995; (b) Saito Y, Takashima Y, Kamada A, Suzuki Y, Suenaga M, Okamoto Y, Matsunaga Y, Hanai R, Kawahara T, Gong X, Tori M, Kuroda C. (2012) Chemical and genetic diversity of Ligularia virgaurea collected in northern Sichuan and adjacent areas of China. Isolation of 13 new compounds. Tetrahedron, 68, 10011–10029.
3.
NaganoH., IwazakiY., GongX., ShenY., KurodaC., HanaiR. (2006) Chemical and genetic differentiation of Ligularia pleurocaulis in northwestern Yunnan and southwestern Sichuan Provinces of China. Bulletin of the Chemical Society of Japan, 79, 300–304.
4.
ToriM., NakamizoH., MiharaK., SatoM., OkamotoY., NakashimaK., TanakaM., SaitoY., SonoM., GongX., ShenY., HanaiR., KurodaC. (2008) Chemical and genetic diversity of Ligularia vellerea in Yunnan, China. Phytochemistry, 69, 1158–1165.
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 the Chemical Society of Japan, 78, 1302–1308.
6.
(a) 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; (b) Shimizu A, Suzuki Y, Torihata A, Hanai R, Saito Y, Tori M, Gong X, Kuroda C. (2012) Complex diversity in Ligularia kanaitzensis. Natural Product Communications, 7, 431–434.
7.
LiuS., IllarionovaI.D. (2011) In Flora of China, WuZY, RavenPH, HongDY. (Eds). Science Press (Beijing) and Missouri Botanical Garden Press (St. Louis), Vol., 20–21, pp 376–415.
8.
NaganoH., HanaiR., YamadaH., MatsushimaM., MiuraY., HoyaT., OzawaM., FujiwaraM., KodamaH., TorihataA., OnukiH., NezuY., KawaiS., YamazakiM., HirotaH., SaitoY., ToriM., OhsakiA., GongX., KurodaC. (2012) Chemical and genetic study of Ligularia duciformis and related species in Sichuan and Yunnan Provinces of China. Chemistry and Biodiversity, 9, 789–805.
9.
(a) GaoK., JiaZ.J. (2000) Two new compounds from Ligularia duciformis. Indian Journal of Chemistry, 39B, 160–161; (b) Gao K, Wang WS, Jia ZJ. (1998) Coniferyl and sinapyl alcohol derivatives from Ligularia duciformis. Phytochemistry, 47, 269–272.
10.
GaoK., YangL., JiaZ.J. (1999) Sesquiterpenes from the roots of Ligularia duciformis. Journal of the Chinese Chemical Society, 46, 619–622.
11.
ToriM., FujiwaraM., OkamotoY., TanakaM., GongX., ShenY., HanaiR., KurodaC. (2007) New oplopane-type sesquiterpenoids from Ligularia duciformis. Natural Product Communications, 2, 357–360.
12.
(a) FuK., YuN., ZhangY., ZhaoY. (2007) Chemical constituents of Ligularia duciformis. Acta Pharmaceutica Sinica, 42, 621–624; (b) Wang WS, Dai X, Hong LY, Lu P, Feng JC, Jiao YG. (2008) New sesquiterpenoids from Ligularia duciformis. Helvetica Chimica Acta, 91, 1118–1123.
13.
HanaiR., YamadaH., SuzukiY., NaganoH., KawaharaT., YuJ.J., GongX., KurodaC. (2012) Chemical constituents of Ligularia nelumbifolia and L. subspicata hybrid collected in Shangrila County, Yunnan province of China. Natural Product Communications, 7, 1565–1568.
YamakawaK., SatohT. (1979) Studies on terpenoids and related alicyclic compounds. XVIII. Stereoselective synthesis of (±)-furanofukinol and (±)-petasalbin. Chemical and Pharmaceutical Bulletin, 27, 1747–1752.
16.
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.
17.
(a) ToriM., OkamotoY., TachikawaK., MiharaK., WatanabeA., SakaokuM., TakaokaS., TanakaM., GongX., KurodaC., HattoriM., HanaiR. (2008) Isolation of new eremophilane-type sesquiterpenoids, subspicatins A-D and subspicatolide from Ligularia subspicata, and chemical and genetic diversity of the species. Tetrahedron, 64, 9136–9142; (b) Saito Y, Hattori M, Iwamoto Y, Takashima Y, Mihara K, Sasaki Y, Fujiwara M, Sakaoku M, Shimizu A, Chao X, Kuroda C, Gong X, Hanai R, Tori M. (2011) Overlapping chemical and genetic diversity in Ligularia lamarum and Ligularia subspicata. Isolation of ten new eremophilanes and a new seco-bakkane compound. Tetrahedron, 67, 2220–2231.
18.
NaganoH., IwazakiY., MatsushimaM., SatoM., GongX., ShenY., HirotaH., KurodaC., HanaiR. (2007) High diversity of Ligularia dictyoneura in chemical composition and DNA sequence. Chemistry and Biodiversity, 4, 2874–2888.
