Free accessResearch articleFirst published online 2015-6
Four New Sesquiterpenoids from Ligularia subspicata Collected in China;Isolation of a Bakkane-type Lactone,an Eremophilane-type Lactone,and Two Ortho Esters
A bakkane type lactone, an eremophilane type lactone, and two ortho esters were isolated from Ligularia subspicata collected in Sichuan Province, China. The ortho ester type compound has been isolated from Ligularia for the first time.
LiuSW. (1989) Flora Reipublicae Popularis Sinicae, Science Press, Beijing, Vol. 77;
2.
LiuS, IllarionovaID. (2011) Flora of China, Science Press, Beijing, and Missouri Botanical Garden Press, St. Louis, Vol. 20–21.
3.
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.
4.
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.
5.
HanaiR, YamadaH, SuzukiY, NaganoH, KawaharaT, YuJJ, 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.
6.
ShimizuA, WatanabeS, HanaiR, OkamotoY, ToriM, GongX, KurodaC. (2014) Chemical and genetic studies on hybrid of Ligularia subspicata and Ligularia cycthiceps collected in Yunnan Province of China. Chemistry & Biodiversity, 11, 1438–1448.
7.
OkamotoY, SaitoY, KurodaC, HanaiR, GongX, ToriM. (2010) Direct MS measurement of the extract of Ligularia virgaurea collected in Yunnan and Sichuan Provinces of China. Phytochemical Analysis, 21, 513–523.
8.
KurodaC, HanaiR, NaganoH, ToriM, GongX. (2012) Diversity of furanoeremophilanes in major Ligularia species in the Hengduan mountains. Natural Product Communications, 7, 539–548.
9.
SaitoY, IchiharaM, OkamotoY, GongX, KurodaM, ToriM. (2014) Twelve new compounds from Ligularia melanothyrsa; isolation of melanothyrsins A-E, normelanothyrsin A, and other eremophilane sesquiterpenoids. Tetrahedron, 70, 2621–2628.
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.
ShirahataK, KatoT, KitaharaY. (1969) Constituents of genus Petasites-IV. Tetrahedron, 25, 3179–3191.
12.
GotoY, KojimaY, NakayamaT, TerazawaM (2001) Allelopathic sesquiterpenoids from rhizomes of Petasites japonicus ssp. giganteus Kitam. Phytochemistry, 57, 109–113.
13.
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.
14.
AbeN, OnodaR, ShirahataK, KatoT, WoodsMC, KitaharaY. (1968) The structure of bakkenolide-A. Tetrahedron Letters, 369–373.
15.
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.
16.
PérezAL, VidalesP, CárdenasJ, VivarAR. (1991) Eremophilanolides from Senecio toluccanus var. modestus. Phytochemistry, 30, 905–908.
17.
BatesRB, PaknikarSK. (1966) Eremophilone and alloeremophilone from hydroxydihydroeremophilone. Chemistry & Industry, 2170–2171.
18.
NayaK, TakagiI, KawaguchiY, AsadaY. (1968) The structure of fukinone, a constituent of Petasites japonicus Maxim. Tetrahedron, 24, 5871–5879.
19.
NayaK, TsujiK, HakuU. (1972) The constituents of Arctium lappa L. Chemistry Letters, 235–236.
20.
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.
