The chemical and genetic diversity of Ligularia species in the Hengduan Mountains area of China is reviewed. A hypothesis that the production of furanoeremophilanes is ecologically advantageous is proposed.
LiuSW, DengDS, LiuJQ. (1994) The origin, evolution and distribution of Ligularia Cass. (Compositae). Acta Phytotaxonomica Sinica, 297, 514–524.
4.
IshizakiY, TanahashiY, TsuyukiT, TakahashiT, ToriK. (1979) Furanoeremophilan-14ß,6α-olide. A new furanosesquiterpene lactone of an eremophilane-type from Ligularia hodgsoni Hook, f Bulletin of the Chemical Society of Japan, 52, 1182–1186;
5.
IshizakiY, TanahashiY, TakahashiT. (1969) Furanoeremophilan-14ß,6α-olide, a new furanosesquiterpene lactone from Ligularia hodgsoni Hook, f The structure and nuclear Overhauser effects. Journal of the Chemical Society, Chemical Communications, 551–552;
6.
PatilF, OurissonG, TanahashiY, WadaM, TakahashiT. (1968) La furanoligularenone. Bulletin de la Société Chimique de France, 1047–1054;
7.
SatoT, MoriyamaY, NaganoH, TanahashiY, TakahashiT. (1975) New furanosesquiterpenes from Ligularia fischeri Turcz. 1ß,10ß-Epoxyfuranoeremophilan-6ß-ol and its derivative. Bulletin of the Chemical Society of Japan, 48, 112–114;
8.
MoriyamaY, TakahashiT. (1976) New sesquiterpene lactones of eremophilane-type from Ligularia fauriei (Fr.) Koidz. Bulletin of the Chemical Society of Japan, 49, 3196–3199;
9.
TadaM, MoriyamaY, TanahashiY, TakahashiT. (1974) Furanoeremophilane-6ß,10ß-diol and its derivatives. New furanosesquiterpenes from Ligularia japonica Less. Bulletin of the Chemical Society of Japan, 47, 1999–2002.
10.
IshiiH, TozyoT, MinatoH. (1965) Studies on sesquiterpenoids-IX. Structure of ligularol and ligularone from Ligularia sibirica Cass. Tetrahedron, 21, 2605–2610.
11.
BohlmannF, ZderoC. (1980) New furanoeremophilane derivatives from Ligularia thyrsoidea. Phytochemistry, 19, 1550–1551;
12.
BohlmannF, GrentzM. (1979) Ein neues furanoeremophilane-derivat aus Ligularia macrophylla. Phytochemistry, 18, 491–492;
13.
BohlmannF, EhlersD, ZderoC, GrenzM. (1977) Über inhaltsstoffe der gattung Ligularia. Chemische Berichte, 110, 2640–2648.
14.
ZhangCF, ZhangM, QuR, WangZT. (2004) Studies on sesquiterpenes constituents of Ligularia pleurocaulis. Chinese Journal of Natural Medicine, 2, 341–343;
LiY, WangZ, ZhangM, ZhouH, ChenJ, LuoS. (2004) New eremophilane-type sesquiterpenes from Ligularia lapathifolia. Planta Medica, 70, 239–243;
17.
LiYS, WangZT, LuoSD, LiSS, ZhuDY. (2006) Sensitized photooxidation of furanoeremophilane with singlet oxygen and their biogenetic relationship. Natural Product Research, 20, 724–730;
18.
WangQ, MuQ, ShibanoM, Morris-NatschkeSL, LeeKH, ChenDF. (2007) Eremophilane sesquiterpenes from Ligularia macrophylla. Journal of Natural Products, 70, 1259–1262.
KurodaC, UeshinoT, NaganoH. (2004) Ehrlich's reaction of furanoeremophilanes. Bulletin of the Chemical Society of Japan, 77, 1737–1740.
21.
KurodaC, NishioE. (2007) Substituent effect in color of Ehrlich's test of tetrahydrobenzofuran. Natural Product Communications, 2, 581–585.
22.
SoltisDE, SoltisPS. (1998) In Molecular systematics of plants. II DNA sequencing. SoltisPS, SoltisDE, DoyleJJ. (Eds). Kluwer Academic Publishers, Boston, 1–42.
23.
GaikwadNW, MadyasthaKM. (2002) Biosynthesis of ß-substituted furan skeleton in the lower furanoterpenoids: a model study. Biochemical and Biophysical Research Communications, 290, 589–594.
24.
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.
25.
MatsushimaM, (2009) Intra-specific diversity of Ligularia dictyoneura and some other Ligularia species in China. Master's Thesis, Ochanomizu University.
26.
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.
ChenHM, WangYY, MaoJM, CaiMS, JiaZJ. (1997) Synthesis and pharmacological activities of the derivatives of furanosesquiterpenes from Ligularia virgaurea. Planta Medica, 63, 299–302;
29.
JiaZJ, ChenHM. (1991) Benzofuranosesquiterpenes from Ligularia virgaurea. Phytochemistry, 30, 3132–3134;
30.
WuQX, WeiQY, ShiYP. (2006) Sesquiterpenes with various carbon skeletons from Ligularia virgaurea spp. oligocephala. Pharmazie, 61, 241–243.
31.
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.
32.
KochMA, DobešC, Mitchell-OldsT, (2003) Multiple hybrid formation in natural populations: concerted evolution of the internal transcribed spacer of nuclear ribosomal DNA (ITS) in North American Arabis divaricarpa (Brassicaceae). Molecular Biology and Evolution, 20, 338–350.
33.
TorihataA, HanaiR, GongX, ShenY, KurodaC. (2007) Chemical and genetic differentiation of Ligularia tsangchanensis in Yunnan and Sichuan Provinces of China. Chemistry and Biodiversity, 4, 500–507.
34.
TerabeM, TadaM, TakahashiT. (1978) Absolute stereochemistry of cacalol. Bulletin of the Chemical Society of Japan, 51, 661–662.
35.
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.
36.
IidaK, MitaniM, KurodaC. (2007) Fixation of natural furanoeremophilane by Diels-Alder reaction. Bulletin of the Chemical Society of Japan, 80, 966–971.
37.
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.
38.
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.
39.
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.
40.
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.
41.
SaitoY, HattoriM, IwamotoY, TakashimaY, MiharaK, SasakiY, FujiwaraM, SakaokuM, ShimizuA, ChaoX, KurodaC, GongX, HanaiR, ToriM. (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.
42.
SaitoY, IchiharaM, OkamotoY, GongX, KurodaC, ToriM. (2011) Five new subspicatins and noreremophilane from Parasenecio petasitoides collected in China. Tetrahedron Letters, 52, 6388–6391.
43.
TorihataA, ChaoX, KurodaC, HanaiR, HirotaH, GongX. (2009) Chemical and genetic differentiation of Ligularia hodgsonii in Japan and China. Chemistry and Biodiversity, 6, 2184–2191.
44.
NaganoH, MatsushimaM, YamadaH, HanaiR, GongX, KurodaC. (2010) Two new furanoeremophilane sesquiterpenoids from Ligularia oligonema. Natural Product Communications, 5, 1–4.
45.
NaganoH, KandaM, YamadaH, HanaiR, GongX, KurodaC. (2010) Chemical and genetic study of Ligularia anoleuca and L. veitchiana in Yunnan and Sichuan Provinces of China. Helvetica Chimica Acta, 93, 1945–1952.
46.
ToriM, TanioY, OkamotoY, SaitoY, GongX, KurodaC, HanaiR. (2008) Chemical constituents of Ligularia franchetiana collected in Yunnan Province of China. Heterocycles, 75, 2029–2034.
47.
KurodaC, KiuchiK, TorihataA, TakeshitaK, GongX, ShenY, HirotaH, OnukiH, HanaiR. (2007) Chemical and genetic diversity of Ligularia latihastata and Ligularia villosa in Yunnan Province of China. Chemistry and Biodiversity, 4, 2210–2217.
48.
OnukiH, YamazakiM, NakamuraA, HanaiR, KurodaC, GongX, ShenY, HirotaH.Chemical constituents and diversity of Ligularia lankongensis in Yunnan Province of China. (2008) Journal of Natural Products, 71, 520–524.
49.
ToriM, FujiwaraM, OkamotoY, TanakaM, GongX, ShenY, HanaiR, KurodaC. (2007) New oplopane-type sesquiterpenoids from Ligularia duciformis. Natural Product Communications, 2, 357–360.
50.
GaoK, JiaZJ. (2000) Two new compounds from Ligularia duciformis. Indian Journal of Chemistry, 39B, 160–161;
51.
GaoK, WangWS, JiaZJ. (1998) Coniferyl and sinapyl alcohol derivatives from Ligularia duciformis. Phytochemistry, 47, 269–272;
52.
GaoK, JiaZ, WangW. (1997) Five coniferyl alcohol derivatives from Ligularia duciformis. Chemical Research in Chinese Universities, 13, 382–385.
53.
YusteF, DíazE, WallsF, JankowskiK. (1976) The structure of cacalone. The Journal of Organic Chemistry, 41, 4103–4106;
54.
OmuraK, NakanishiM, TakaiK, NayaK. (1978) The sesquiterpenes of Cacalia species: 8-oxocacalol and the stereochemistry of cacalone epimers. Chemistry Letters, 1257–1260.
BohlmannF, KnollKH. (1979) Zwei neue eremophilan-derivate aus Senecio sauveolens. Liebigs Annalen der Chemie, 470–472;
57.
BohlmannF, ZiescheJ, KingRM, RobinsonH. (1980) Seven furanoeremophilanes from three Senecio species. Phytochemistry, 19, 2675–2679;
58.
BohlmannF, ZderoC. (1978) New norsesquiterpenes from Senecio digitalifolius. Phytochemistry, 17, 759–761.
59.
Garduño-RamírezML, TrejoA, NavarroV, ByeR, LinaresE, DelgadoG. (2001) New modified eremophilanes from the roots of Psacalium radulifolium. Journal of Natural Products, 64, 432–435;
60.
AnayaAL, Hernández-BautistaBE, Torres-BarragánA, León-CanteroJ, Jiménez-EstradaM. (1996) Phytotoxicity of cacalol and some derivatives obtained from the roots of Psacalium decompositum (A. Gray) H. Rob. & Brettell (Asteraceae), Matarique or Maturin. Journal of Chemical Ecology, 22, 393–403.
61.
BohlmannF, KnollKH. (1978) Weitere furanoeremophilane aus Othonna-arten. Phytochemistry, 17, 461–465.
62.
BohlmannF, ZderoC. (1978) Neue furanoeremophilane und andere sesquiterpene aus vertretern der gattung Euryops. Phytochemistry, 17, 1135–1153.
63.
LiuJQ, WangYJ, WangAL, OhbaH, AbbottRJ. (2006) Radiation and diversification within the Ligularia-Cremanthodium-Parasenecio complex (Asteraceae) triggered by uplift of the Qinghai-Tibetan plateau. Molecular Phylogenetics and Evolution, 38, 31–49.