Three Novel Eremophilanolides from Ligularia virgaurea spp. oligocephala

From the alcoholic extract of the whole plant of Ligularia virgaurea spp. oligocephala, three novel eremophilane sesquiterpene lactones, 6α, 10α-dihydroxy- 1-oxoeremophila-7(11), 8(9)-dien-8, 12-olide, 613, 10α-dihydroxy-1-oxoeremophila-7 (ll), 8 (9)-dien-8, 12-olide and 10α-hydroxy-1-oxoeremophila-7(l 1), 8(9)-dien-8, 12-olide were isolated. Their structures were elucidated by various spectroscopic methods including intensive 2D NMR techniques (COSY,HMQC, HMBC and ^1H-^1H NOESY) and HR-MS.     

Sesquiterpenoids and Lignans from Ligularia virgaurea spp. oligocephala

From the BuOH extract of the whole plant of Ligularia virgaurea spp. oligocephala, a series of sesquiterpenes, sesquiterpene glycosides, and lignan glycosides were isolated, including the three new compounds (1α)‐1‐hydroxy‐8‐oxo‐eremophila‐6,9‐dien‐12‐oic acid ( 1 ), 8‐[(β‐D ‐glucopyranosyl)oxy]eremophila‐1(10),8,11‐trien‐2‐one ( 2 ), and 4‐[(β‐D ‐glucopyranosyl)oxy]pinoresinol ( 4 ). Their structures were elucidated by 1D‐ and 2D‐NMR as well as HR‐ESI‐MS analyses, and by comparison of the spectroscopic data with those reported for structurally related compounds.     

Novel Sesquiterpenes from Ligularia virgaurea spp. oligocephala

Two novel sesquiterpene dimers, ligularin A ( 1 ) and ligulolide D ( 2 ), and one new sesquiterpenoid, 1β,10α‐dihydroxy‐6β‐[(2‐methylpropyl)oxy]furanoeremophil‐9‐one ( 3 ), as well as two known sesquiterpenoids, 6β‐[(2‐methylpropyl)oxy]‐furanoeremophil‐1(10)‐en‐9‐one ( 4 ) and 1‐hydroxy‐3,7‐dimethyl‐2‐(pent‐3‐enyl)benzofuran ( 5 ), were isolated from the petroleum‐ether fraction from an alcoholic extract of the whole plant of Ligularia virgaurea spp. oligocephala. Their structures were elucidated by 1D and 2D‐NMR spectroscopy together with HR‐ESI‐MS analysis, and comparison of the spectroscopic data with those reported for structurally related compounds. In addition, the cytotoxicities against human gastric cancer SGC‐7910 cell were measured in vitro, the results demonstrated that these sesquiterpenes have no cytotoxicity against the selected tumor cell (all IC₅₀ values >200 μM ).     

A new eremophilane-type sesquiterpene from Ligularia virgaurea

A new eremophilane-type sesquiterpene,1α,8β,10β-trihydroxy-6β-(2-methylacryloyl)oxyeremophil-7(11)-en-8α,12-olide, was isolated from the roots of Ligularia virgaurea.Its structure was established on the basis of various spectroscopic analyses, including the 1D,2D NMR techniques and HR-ESI-MS.     

Eremophilane,bakkane, secoeremophilane,and secobakkane sesquiterpenoids from Ligularia virgaurea collected in China

Secobakkane B (C-6/C-7 cleaved secobakkane type aldehyde), secovirgaurenols B and C (C-8/C-9 cleaved secoeremophilane type), a 1β,10β-epoxyfuranoeremophilane, two 1β,10β-epoxyeremophilanolides, and fukinospirolide C (bakkane-type lactone), as well as 33 known compounds were isolated from three samples of Ligularia virgaurea collected in China. Two of the three analyzed samples were grouped in the neoadenostylone (N) type, and the rest, a mixture of the 6-hydroxyeuryopsyn (H) and cacalol (C) types, out of five chemotypes found in this species.     

Two New Sesquiterpenes from Ligularia macrophylla

Two new eremophilane sesquiterpenes, 15β-formic ether-6-oxo-furanoeremophilane （1） and 6α, 15β-epoxy eremophila-7（11）-en-8α, 12-olide （2） were isolation from the roots of Ligularia macrophylla. Their structures were deduced from spectroscopic methods and 2D NMR experiments.     

Eremophilane‐Type Sesquiterpenes from the Roots of Ligularia virgaurea

From the roots of Ligularia virgaurea, five new eremophilane‐type sesquiterpenes were isolated, including three new eremophilenolides, 6β‐(angeloyloxy)‐1α,8β,10β‐trihydroxyeremophil‐7(11)‐en‐12,8α‐olide ( 1 ), 6β‐(angeloyloxy)‐1β,10β‐epoxy‐8β‐ethoxyeremophil‐7(11)‐en‐12,8α‐olide ( 2 ), and 1β,10β‐epoxy‐8β‐ethoxy‐6β‐[(2‐methylacryloyl)oxy]eremophil‐7(11)‐en‐12,8α‐olide ( 3 ), two new noreremophilanes, 3β‐[(2‐methylacryloyl)oxy]‐8‐oxo‐12‐noreremophil‐6‐en‐11‐one ( 9 ), and 9β‐hydroxy‐8‐oxo‐12‐noreremophil‐6‐en‐11‐one ( 10 ), and six known eremophilanes, namely 4 – 8 , and 11 . Their structures were elucidated by means of spectral methods, such as IR, HR‐ESI‐MS, and 1D‐ and 2D‐NMR, and by comparison of the spectral data with those reported for structurally related compounds.     

Sesquiterpenoids from the Rhizome of Ligularia virgaurea

Two novel sesquiterpene dimers, compounds 1 and 2 , were isolated from the rhizome of Ligularia virgaurea, together with the six known sesquiterpenoids 3 – 8 . Their structures were established by physico‐chemical and spectroscopic methods, especially by means of 1D‐ and 2D‐NMR as well as HR‐MS analyses. A mechanism based on a classical Diels–Alder cyclization is proposed for the formation of the dimer 1 from the precursors 8 and the quinone form of 6 (Scheme).     

Two New Eremophilane Sesquiterpene Lactones from Ligularia myriocephala Ling

Two new eremophilane sesquiterpene lactones, 1β-angeloyloxy-6β, 10β-dihydroxy-8β- methoxyeremophila-7（ll）en-8α,12-olide and 1β-angeloyloxy-6β,10α-dihydroxy-8α-methoxyeremo- phila-7（ 11）en-8β, 12-olide were isolated from the extract of the whole plant of Ligularia myriocephala Ling. Their structures and stereochemistry were elucidated by various spectroscopic methods including intensive 2D-NMR techniques （COSY, gHMQC, gHMBC and ^1H-^1H NOESY） and HR-ESIMS.     

Two New Eremophilane Sesquiterpenes from Cacalia ainsliaeflora

The root of C. ainsliaeflora has been used for curing pellagra, rheumatismal edema and insecticide1. In this paper, we report the structure elucidation of two new eremophilane sesquiterpenes (1, 2) from the roots of C. ainsliaeflora. Compound 1, colorless gum, [(]: -50 (c 0.50, CHCl3). HRESI-MS showed [M+H]+ at m/z 377.19528 (calcd for C21H29O6 377.19587), corresponding to a molecular formula C21H28O6. Its IR bands (1655, 1717, 1750cm-1) and UV absorptions (221 nm) displayed the typi…     

Eremophilane Sesquiterpenes from Cacalia Roborowskii

Themajorityofphytochemicalstudiesonsenencioneace(compositae)specieshavebeenconcentratedonthepyrrolizidinealkaloidsandsesquiteIPenesbecauseoftheirpotentialbioactivitiesandCytotoalcactivities.lCacaliaroborowskii(maxim)LinginslongbeenusedasfolkremedyinnorthwestemChina.Recently,wehadisolatedseveralneweremophilenolides'fromtherootsofthisplant.Asacontinuahonofourinvestigationontillsspecies,wenowpresenttileisolationandsmicturalelucid.ltionoffouraddihonalneweremophilanesesquiterpenes.Theirsmicturesw…     

Eremophilane Sesquiterpenoids from Ligularia fischeri

A novel eremophilane dimer, named as fischelactone, and a new sesquiterpene lactam, eremophila‐1(10),7(11),8‐triene‐12,8‐lactam, along with ten known compounds, were isolated from the roots of Ligularia fischeri. Their structures were established by means of spectroscopic analyses (EI‐MS, HR‐ESI‐MS, IR, and 1D‐ and 2D‐NMR data) and X‐ray diffraction study.     

Two new eremophilane Sesquiterpenoides from Ligularia dictyoneura

Abstract

Two new eremophilane sesquiterpenoides, 6α,9α-dihydroxyeremophilenolide (1), and 1β,10β-dihydroxyeremophilenolide (2), along with ten known eremophilane sesquiterpenoides (3–12) were isolated from the aerial parts of Ligularia dictyoneura (Franch.) Hand.-Mazz. Their structures were elucidated by means of extensive spectroscopic analysis. Compounds 3–6 were assessed for their cytotoxicity against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that they had no activity.     

Two Novel Epimeric Eremophilane Sesquiterpenes from the Flower of Cacalia tangutica

Two novel epimeric eremophilane sesquiterpenes, 7β-H-3α-angeloyl-9(10)-ene-11,12-epoxy-8-oxoeremophilane (1) and 7β-H-3α-angeloyl-9(10)-ene-11, 12-epoxy-8-oxoeremophilane (2) were isolated from the methanol extract of the flower of Cacalia tangutica (Franch.) Hand-Mazz. Their structures were characterized by 1D-, 2D-NMR (^1H-^1H COSY, HMQC, HMBC, ^1H-^1H NOESY) and HRESI-MS techniques.     

Five New Eremophilane Sesquiterpenes from Ligularia przewalskii

Five new eremophilane‐type sesquiterpenes, 3β‐(acetyloxy)‐7‐hydroxynoreremophila‐6,9‐dien‐8‐one ( 1 ), 8β‐hydroxy‐2‐dehydroxyliguhodgsonal ( 2 ), 3β‐(acetyloxy)‐11‐methoxy‐8‐oxoeremophila‐6,9‐dien‐12‐oic acid ( 3 ), 3β‐(acetyloxy)‐11‐(2′‐methylbutanoyloxy)‐8‐oxoeremophila‐6,9‐dien‐12‐oic acid ( 4 ), and 3β‐(acetyloxy)‐6α‐hydroxyligularenolide ( 5 ), along with the three known compounds 6 – 8 , were isolated from the roots of Ligularia przewalskii. The structures of the new compounds were elucidated through spectral studies including HR‐EI‐MS, IR, and NMR data.     

Two New Eremophilenolides from Ligularia sagitta

Chemical investigation of L.sagitta afforded two new eremophilenolides, which were identified as 6β-angeloyloxy-10β-hydroxy-8 β-methoxy-eremophil-7(11)-en-12, 8α-olide (1) and 6β, 8β-dimethoxy-10β-hydroxy-eremophil-7(11)-en-12, 8α-olide (2). Their structures were estab- lished by spectroscopic methods including 2D NMR experiments.     

Two New Eremophilenolides from Ligularia tongolensis

Chemical investigation of L. tongolensis afforded two new eremophilenolides, which were identified as 3β-（2＇-methylbutanoyloxy）-8βH-eremophil-7（11）-en-12, 8α（14, 6α）-diolide （1）and 8βH-eremophil-3, 7（11）-dien-12, 8α （14, 6α）-diolide （2）. Their structures were established by spectroscopic methods including 2D NMR experiments.     

Fischelactone B: A New Eremophilane Dimer from Ligularia fischeri

A new eremophilane dimer, namely fischelactone B, was isolated from the roots of Ligularia fischeri. Its structure was established on the basis of spectroscopic data, including IR, HR‐ESI‐MS, and 1D NMR and 2D NMR spectroscopy.     

Two New Eremophilenolides from Ligularia fischeri

Ligulariajischerihasl0ngbeenusedastraditi0naImedicinet0relievec0ugh,invig0ratethecircuIation0fbIo0dandst0ppain'.FromtheplantgrowinginShengnonaiia,Hubei-Chlna,t\v0neweremophiIen0lideshavebeenisolated.Comp0undlwasneedlecrystalsfrompetr0lether(60-9O'C),m.p.=148-l50'C.ItsformulawasdeterminedasC,,H,'O'by"C-NMRandDEPTspectrainaccordancewiththem0lecularionpeakm/z=280inEIMS.Thetypeofcarbonsignals(5xC,3xCH,4xCH,,4xCH,)(Table2)sh0wedithadabicyclicsesquiterpeneskeletonbearingameth0xy.ahemi-…