A New Triterpene and New Sesquiterpenes from the Roots of Ligularia sagitta

One new triterpene and seven new eremophilane‐type sesquiterpenes were isolated from the roots of Ligularia sagitta, among them 1a , an O‐acetylated oleanane type triterpene, 2a and 3a , two 11‐nor eremophilane‐type sesquiterpenes, 4a, 5 , and 6 , three standard eremophilane‐type sesquiterpenes, and 7 and 8 , two tri‐nor eremophilane‐type sesquiterpenes. Their structures were established by extensive spectral analyses (1D, 2D‐NMR, IR, and MS). Compound 1a showed moderate cytotoxicity against two tumor cell lines.     

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.     

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 Sesquiterpenes from Ligularia lankongensis

In continuation of a systematic investigation into the chemotaxonomic and bioactive components of pyrrolizidine alkaloids and sesquiterpenoids of Ligularia plants, two new, highly oxygenated, rare bisabolene sesquiterpenes, compounds 1 and 2 , were isolated from the roots of Ligularia lankongensis. Their structures and relative configurations were elucidated by means of 1D‐ and 2D‐NMR as well as MS analyses.     

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 ).     

New Oplopane‐Type Sesquiterpenes from Ligularia narynensis

Four new, highly oxygenated oplopane‐type sesquiterpenes ( 3 – 6 ) were isolated from the roots of Ligularia narynensis, together with four known compounds, and their structures were elucidated by spectroscopic methods and comparison with literature data. Selected congeners were evaluated for their in vitro cytotoxic activities against cultured SMMC‐7721 (human hepatoma), L02 (human hepatocyte), and HL‐60 (human promyelocytic leukemia) cells, but were found to be inactive.     

Two New Sesquiterpenes from Ligularia Duciformis

ＡｐｒｅｖｉｏｕｓｐｈｙｔｏｃｈｅｍｉｃａｌｓｔｕｄｙｏｆＬｉｇｕｌａｒｉａｄｕｃｉｆｏｒｍｉｓｄｅａｌｔｗｉｔｈｔｈｅｉｓｏｌａｔｉｏｎｏｆｃｏｎｉｆｅｒｙｌａｌｃｏｈｏｌｄｅｒｉｖａｔｉｖｅｓ［１,２］．Ｉｎｏｒｄｅｒｔｏｆｉｎｄｓｅｓｑｕｉｔｅ...     

Sesquiterpenes from the Roots of Ligularia duciformis

Two new sesquiterpenes named liguducin-A ( 1 ) and -B ( 4 ) were isolated from a Chinese medicinal plant, the dried roots of Ligularia duciformis, together with four known sesquiterpenes, 4α, 10β-dihydroxy-1β,5α-H-guai-6-ene ( 2 ), 4α-hydroxy-1β,5α,11α-H-guai-9-en-12,8α-olide ( 3 ), 1β-hydroxyeudesm-4,11-dien-3-one ( 5 ) and 1β,6α-dihydroxyeudesm-4(15)-ene ( 6 ). On the basis of the spectral evidence, their structures were determined.     

Three New Sesquiterpenes from Laggera pterodonta

A new eremophilane sesquiterpene, (2β)‐2‐deoxo‐2‐methoxytessaric acid ( 1 ), and two new eudesmane sesquiterpenes, (3β,10α)‐3‐methoxyleudesma‐4,11(13)‐dien‐12‐oic acid ( 2 ) and (3α,4β,8α)‐4‐(acetyloxy)‐3‐(2,3‐dihydroxy)‐2‐methyl‐1‐oxobutoxy‐8‐hydroxyeudesm‐7(11)‐eno‐12,8‐lactone ( 3 ), along with the ten known compounds 4 – 13 were isolated from the aerial parts of Laggera pterodonta. The structures of the new compounds were elucidated by spectroscopic analyses, including 2D‐NMR data.     

A New Eremophilane Sesquiterpenoid from Ligularia przewalskii

Chemistry of Natural Compounds - A new eremophilane sesquiterpenoid, 3β-acetoxy-6α-angeloyloxy-eremophil-1(10),7(11),8(9)-trien-12,8-olide (1), was isolated from Ligularia przewalskii....     

Two New Sesquiterpenes from Ligularia veitchiana

A new furanoeremophilane and a new eudesmane were isolated from the roots of Ligularia veitchiana .Their structures were elucidated as 1 β,10β-epoxy-6β-isobutyryloxy-9-oxo-furanoeremophilane and 8α-hydroxy-4(15),11-eudesmadiene by spectroscopic methods.     

Three New Bisabolane Sesquiterpenes from Ligularia songarica

Three new bisabolane sesquiterpenes, songaricalarins F–H ( 1 – 3 , resp.), and five known analogs, 4 – 8 , were isolated from roots and rhizomes of Ligularia songarica. The structures were elucidated by spectroscopic methods, including 2D‐NMR techniques. The isolated compounds were also evaluated for their cytotoxic activities, against human lung carcinoma (A‐549) and human breast adenocarcinoma (MCF‐7) cell lines, and three compounds were found to show moderate cytotoxicities.     

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.     

Pyrrolizidine Alkaloids and Bisabolane Sesquiterpenes from the Roots of Ligularia cymbulifera

The new pyrrolizidine alkaloid glycoside 1 , and the three new highly oxygenated bisabolane sesquiterpenes 4 – 6 , together with the two known pyrrolizidine alkaloids 2 and 3 , were isolated from the roots of Ligularia cymbulifera (W. W. Smith ) Hand .‐Mazz . Their structures were established on the basis of spectroscopic analysis, especially 1D‐ and 2D‐NMR data. The cytotoxic activities of compounds 1, 2 , and 4 – 6 were evaluated against hepatoma (BEL‐7402), human leukemia (HL‐60), human ovarian carcinoma (HO‐8910), and nasopharyngeal carcinoma (KB) cell lines (Tables 1–3). Compound 6 s howed weak cell‐growth inhibition of BEL‐7402 cell.     

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.     

Sesquiterpenes from Ligularia Hodgsonii

A new nor‐sesquiterpenoid eremophilane derivative and a new eudesmane derivative were isolated from the whole plants of Ligularia hodgsonii. Their structures were elucidated by spectroscopic methods and 2D NMR techniques.     

Sesquiterpenes from Ligularia Fischeri

Phytochemical investigation of the whole plant of Ligularia fischeri afforded two new sesquiterpenes 11‐hydroxy‐eremophil 1(10)‐en‐2,9‐dione (1) ; and 1β,11‐dihydroxy‐eremophil‐9‐ene (2) ; four known compounds (‐)‐4β,7α‐aromadendranediol (3) ; 1β,6α‐dihydroxyeudesm‐4(15)‐ene (4) ; Teucdiol A (5) ; Teucdiol B (6) . The new compound structures were elucidated by spectroscopic methods including 2D‐NMR techniques.     

Two New Bisabolane Sesquiterpenes from Ligularia Thyrsoidea

ＩｎＣｈｉｎａ，ｍｏｒｅｔｈａｎ２０Ｌｉｇｕｌａｒｉａｓｐｅｃｉｅｓ（Ｃｏｍｐｏｓｉｔａｅ）ｈａｖｅｂｅｅｎｕｓｅｄｆｏｒｆｏｌｋｍｅｄｉｃｉｎｅｓｗｉｔｈａｎｔｉｂｉｏｔｉｃ，ａｎｔｉｐｈｌｏｇｉｓｔｉｃａｎｄａｎｔｉｔｕｍｏｒａｃｔｉｖｉｔｉｅｓ...