Three new eremophilanes were isolated from a sample of Ligularia collected in Yunnan province of China and their structures were determined. The chemical constituents including eleven eremophilanes (major constituents: 6-acyloxyfuranoeremophilan-10β-ols) were similar to those of a hybrid of L. cyathiceps and L. subspicata, however, the base sequence of the ITS1-5.8S-ITS2 region was typical of L. cyathiceps, indicating backcrossing.
RiesbergLH, CarneySE. (1998) Plant hybridization. New Phytologist, 140, 599–624.
2.
KurodaC, HanaiR, NaganoH, ToriM, GongX. (2012) Diversity of furanoeremophilanes in major Ligularia species in the Hengduan Mountains. Natural Product Communications, 7, 539–548
3.
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.
4.
ShimizuA, WatanabeS, HanaiR, OkamotoY, ToriM, GongX, KurodaC. (2014) Chemical and Genetic Study on Hybrid of Ligularia subspicata and L. cyathiceps Collected in Yunnan Province of China. Chemistry and Biodiversity, 11, 1438–1448.
5.
NaganoH, TorihataA, MatsushimaM, HanaiR, SaitoY, BabaM, TanioY, OkamotoY, TakashimaY, IchiharaM, GongX, KurodaC, ToriM. (2009) Chemical and genetic study of Ligularia cyathiceps in Yunnan province of China. Helvetica Chimica Acta, 92, 2071–2081.
6.
SaitoY, HattoriM, IwamotoY, TakashimaY, MiharaK, SasakiY, FujiwaraM, SakaokuM, ShimizuA, ChaoX, KurodaC, GongX, HanaiRToriM. (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.
7.
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.
8.
SaitoY, IchiharaM, OkamotoY, GongX, KurodaC, ToriM. (2011) Five new subspicatins and noreremophilane from Parasenecio petasitoides collected in China. Tetrahedron Letters, 52, 6388–6391.
9.
BohlmannF, ZderoC, BergerD, SuwitaA, MahantaP, JeffreyC. (1979) Neue Furanoeremophilane und weitere Inhaltsstoffe aus Südafrikanischen Senecio-Arten. Phytochemistry, 18, 79–93.
10.
TadaM, MoriyamaY, TanahashiY, TakahashiT. (1971) New furanosesquiterpenes from Ligularia japonica Less. Furanoeremophilane-6ß,10ß-diol, 10ß-hydroxy-6ß-methoxyfuranoeremophilane and 10ß-hydroxyfuranoeremophilan-6ß-yl 2′Ç-methylbutanoate. Tetrahedron Letters, 12, 4007–4010.
11.
BohlmannF, ZderoC, GrenzM. (1974) Natürlich vorkommende Terpen-Derivate, XLII. Neue Sesquiterpene der Gattung Orthonna. Chemische Berichte, 107, 3928–3945.
12.
JenningsPW, HurleyJC, ReederSK, HolianA, LeeP, CaughlanCN, LarsenRD. (1976) Isolation and structure determination of the second toxic constituent from Tetradymia glabrata. Journal of Organic Chemistry, 41, 4078–4081.
13.
BohlmannF, JakupovicJ, WarningU, GrenzM, Chau-ThiTV, KingM, RobinsonH. (1986) Sesquiterpenes with new carbon skeletons. Furoeremophilanes, secoeremophilanes, and other constituents from Argentinian Senecio species. Bulletin de la Société chimique de Belgique, 95, 707–736.
14.
BohlmannF, ZderoC. (1978). Neue Furanoeremophilane und andere Sesquiterpene aus Vertretem der Gattung Euryops. Phytochemistry, 17, 1135–1153.
15.
BohlmannF, SuwitaA. (1976) Natürlich vorkommende Terpen-Derivate, LVII. Weitere Furanoeremophilane aus Orthonna-Arten. Chemische Berichte, 109, 1230–1238.
16.
WhiteTJ, BrunsT, LeeS, TaylorJ. (1990) Amplification and direct sequencing of fungal ribosomal RNA genes for phylogenetics. In PCR protocols: a guide to methods and applications. InnisMA, GelfandDH, SminskiJJ, WhiteTJ. (Ed). Academic Press, San Diego, 315–322.
17.
TaylorDL, BoothMG, McFarlandJW, HerriottIC, LennonNJ, NusbaumC, MarrTG. (2008) Increasing ecological inference from high throughput sequencing of fungi in the environment through a tagging approach. Molecular Ecology Resources, 8, 742–752.
18.
NaganoH, MatsushimaM, YamadaH, HanaiR. Gong X, Kuroda, C. (2010) Two new furanoeremophilane sesquiterpenoids from Ligularia oligonema. Natural Product Communications, 5, 1–4.