The chemical composition of a sample of the title species collected in Pianma, Lushui County, Yunnan Province of China, was examined. Two 3,6,10-oxygenated and two 3,6-oxygenated furanoeremophilanes were isolated. Structures of two new compounds were elucidated. The 3,6-oxygenated furanoeremophilanes were not detected in a sample of the same species previously collected in Laojunshan, Jianchuan County, Yunnan, indicating chemical diversity in the species.
(a) LiuS., IllarionovaI.D. (2011) In Flora of China, WuZ.Y., RavenP.H., HongD.Y. (Eds). Science Press (Beijing) and Missouri Botanical Garden Press (St. Louis), Vol. 20–21, pp 376–415; (b) Liu SW. (1989) Flora Reipublicae Popularis Sinicae, Science Press, Beijing, Vol. 77.
2.
(a) KurodaC., HanaiR., NaganoH., ToriM., GongX. (2012) Diversity of furanoeremophilanes in major Ligularia species in the Hengduan Mountains. Natural Product Communications, 7, 539–548; (b) Kuroda C, Hanai R, Tori M, Okamoto Y, Saito Y, Nagano H, Ohsaki A, Hirota H, Kawahara T, Gong X. (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.
NaganoH., MatsushimaM., YamadaH., HanaiR., GongX., KurodaC. (2010) Two new furanoeremophilane sesquiterpenoids from Ligularia oligonema. Natural Product Communications, 5, 1–4.
4.
ToriM., TanioY., OkamotoY., SaitoY., GongX., KurodaC., HanaiR. (2008) Chemical constituents of Ligularia franchetiana collected in Yunnan Province of China. Heterocycles, 75, 2029–2034.
5.
HirotaH., HoriguchiY., KawaiiS., HanaiR., GongX., KurodaC. (2014) The first isolation of furanoeremophilane from Ligularia nelumbifolia. Natural Product Communications, 9, 325–327.
6.
(a) KurodaC., UeshinoT., NaganoH. (2004) Ehrlich's reaction of furanoeremophilanes. Bulletin of the Chemical Society of Japan, 77, 1737–1740; (b) Kuroda C, Nishio, E. (2007) Substituent effect in color of Ehrlich's test of tetrahydrobenzofuran. Natural Product Communications, 2, 581–585.
7.
BohlmannF., ZderoC. (1978) New furanoeremophilanes from south African Senecio species. Phytochemistry, 17, 1161–1164.
8.
(a) TadaM., SatoT., TakahashiT., ToriK., HoribeI., KuriyamaK. (1981) Conformational equilibria of eremophilanes, naturally occurring cis-decalin derivatives, studied by NMR and CD spectroscopy. Journal of the Chemical Society, Perkin Transactions 1, 2695–2701; (b) Sato T, Tada M, Takahashi T, Horibe I, Ishii H, Tori K. (1977) Carbon-13 and hydrogen-1 NMR studies of conformations of ligularol and 6-epiligularol, naturally occurring cis-decalin derivatives. Tetrahedron Letters, 3895–3898.
9.
(a) OkamotoY., TaniguchiM., TeradaK., NakashimaK., GongX., HanaiR., ToriM., KurodaC. (2016) Diversity in chemical constituents of Ligularia longihastata collected in China. Natural Product Communications, 11, 145–148; (b) Kuroda C, Shibayama C, Inoue K, Okamoto Y, Tori M, Saito Y, Hanai R, Gong X. Chemical lineages of Ligularia fischeri. Natural Product Communications, 11, 139–143.
10.
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.
11.
TorihataA., ChaoX., KurodaC., HanaiR., HirotaH., GongX. (2009) Chemical and Genetic Differentiation of Ligularia hodgsonii in Japan and China. Chemistry and Biodiversity, 6, 2184–2191.
12.
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.
13.
(a) LiW.X., LeiM., FeiD.Q., GaoK. (2009) Eremophilane-type sesquiterpene derivatives from Ligularia hodgsonii. Planta Medica, 75, 635–640; (b) Xu JQ, Li YS, Li YM, Jiang SH, Tan CH, Zhu DY. (2006) New eremophilane-type sesquiterpenes from Ligularia hodgsonii. Planta Medica, 72, 567–569.
14.
(a) DengM., DongW., JiaoW., LuR. (2009) New eremophilane sesquiterpenes from the roots of Ligularia fischeri. Helvetica Chimica Acta, 92, 495–501; (b) Xu JQ, Hu LH. (2009) New eremophilane sesquiterpenes from Ligularia japonica. Helvetica Chimica Acta, 92, 357–361; (c) Wang WS, Dai X, Hong LY, Lu P, Feng JC, Jiao YG. (2008) New sesquiterpenoids from Ligularia duciformis. Helvetica Chimica Acta, 91, 1118–1123.