Sesquiterpene Lactone Glycosides from Carpesium macrocephalum

Two new sesquiterpene lactone glycosides were isolated from the seeds of Carpesium meacrocephalum. Their structures were elucidated as 2α-O-β-D-glucopyranosy-5α,11αH-eudesma-4(15)-en-12,8β-olide and 2α-O-β-D-glucopyranosy-5αH-eudesma-4(15),11(13)-dien-12,8β-olide by spectral methods (HRMS,1D and 2D NMR).     

Eudesmanolides and Guaianolides from Carpesium triste

A new eudesmanolide, 1‐oxo‐11αH‐eudesma‐2,4(14)‐dien‐12,8β‐olide ( 1 ), and four new guaianolides, 9β,10β‐epoxy‐4α‐hydroxy‐1βH,11αH‐guaian‐12,8α‐olide ( 2 ), 9β,10β‐epoxy‐4α‐hydroxy‐1βH,11βH‐guaian‐12,8α‐olide ( 3 ), 4α,9α‐dihydroxy‐1βH,11αH‐guai‐10(14)‐en‐12,8α‐olide ( 4 ), and 4α,9α‐dihydroxy‐1βH,11βH‐guai‐10(14)‐en‐12,8α‐olide ( 5 ), together with one known eudesmanolide and two known germacranolides, were isolated from the whole plants of Carpesium triste. Their structures and relative configurations were elucidated on the basis of spectroscopic methods, including 2D‐NMR techniques.     

New Acyclic 12‐Hydroxygeranylgeraniol‐Derived Diterpenoids from the Seeds of Carpesium triste

Five new acyclic 12‐hydroxygeranylgeraniol‐derived diterpenoids, i.e., 1 – 5 , were isolated from the seeds of Carpesium triste. The structures including the absolute configurations of the new compounds were elucidated by spectroscopic methods. All the compounds, except for 2 , were evaluated for their in vitro cytotoxic activity against cultured SMMC‐7721 (human hepatoma), HL‐60 (human promyelocytic leukemia), and L02 (human hepatocyte) cells.     

Synthesis of 8‐Desoxythunberginol A and (±)‐8‐Desoxy‐3,4‐Dihydrothunberginol A

A two step synthesis of title isocoumarin isolated from Homalium longifolium and its conversion into corresponding 3,4‐dihydroisocoumarin has been described. 3,4‐Dimethoxybenzoyl chloride on condensation with homophthalic acid afforded 3‐(3′,4′‐dimethoxyphenyl)isocoumarin which was demethylated to furnish the 8‐desoxythunberginol A, whereas its sequential saponification, reduction and demethylation yielded the (±)‐8‐desoxy‐3,4‐dihydrothunberginol A. The synthesized compounds were examined in vitro for antibacterial activity.     

Two New Bisabolane Sesquiterpenes from Leontopodium longifolium

Leontopodium longifolium (Compositae) have long been used as folk medicine in China for releasing a cough, expectorant and treatment of bronchitis1,2. The chemical constituents of the Leontopodium longifolium were not reported so far. Here we report the s…     

Germacranolides from Carpesium divaricatum: Some New Data on Cytotoxic and Anti-Inflammatory Activity

Carpesium divaricatum Sieb. & Zucc., a traditional medicinal plant used as an inflammation-relieving remedy, is a rich source of terpenoids. At least 40 germacrane-type sesquiterpene lactones, representatives of four different structural groups, were isolated from the plant. Cytotoxicity against cancer cells in vitro is the most frequently described biological activity of the compounds. However, little is known about the selectivity of the cytotoxic effect. The anti-inflammatory activity of the germacranolides is also poorly documented. The objective of the present study was to assess the cytotoxic activity of selected C. divaricatum germacranolides-derivatives of 4,5,8,9-tetrahydroxy-3-oxo-germacran-6,12-olide towards cancer and normal cell lines (including cells of different p53 status). Moreover, to assess the anti-inflammatory effect of the compounds, the release of four proinflammatory cytokines/chemokines (IL-1β, IL-8, TNF-α and CCL2) by lipopolysaccharide-stimulated human neutrophils was measured by ELISA. The investigated sesquiterpene lactones demonstrated nonselective activity towards prostate cancer (Du145 and PC3) and normal prostate epithelial cells (PNT2) as well as against melanoma cells (A375 and HTB140) and keratinocytes (HaCaT). Cytotoxic activity against osteosarcoma cells was independent of their p53 status. In sub-cytotoxic concentrations (0.5–2.5 µM) the studied compounds significantly decreased cytokine/chemokine release by lipopolysaccharide-stimulated human leukocytes.     

New Sesquiterpene Lactones from Carpesium Lipskyi

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Composition of Essential Oils from Roots and Aerial Parts of Carpesium cernuum and Their Antibacterial and Cytotoxic Activities

Carpesium cernuum L., one of the two Carpesium species occurring in Europe, in the Far East and India, found use as a vegetable and a traditional medicinal remedy for several ailments. In the present study, compositions of essential oils distilled from roots and shoots of C. cernuum plants, cultivated in the open field, have been studied by GC-MS-FID supported by NMR spectroscopy. The analyses led to the identification of 120 compounds in total, of which 115 were found in aerial parts and 37 in roots of the plants. The major constituents found in the oil from shoots were: α-pinene (35%) and 2,5-dimethoxy-p-cymene (thymohydroquinone dimethyl ether, 12%), whereas 2,5-dimethoxy-p-cymene (55%), thymyl isobutyrate (9%) and thymol methyl ether (8%) predominated in the essential oil obtained from the roots. Antibacterial and cytotoxic activities of the essential oils distilled from C. cernuum were also tested. The essential oil from aerial parts of the plant demonstrated good inhibitory activity against Staphylococcus aureus ATCC 29213 and Escherichia coli ATCC 25922 (MIC: 15.6 μL/mL).     

A New Eudesmanolide and a New Aromatic Derivative from Carpesium cernuun

Carpesium cernuun L. has long been used as chinese folk medicine for its anti-inflammatory, pain-relief, and detoxication properties1. Up to now, no phytochemical studies of Carpesium cernuun has been carried out. Here we report the structure elucidation of a new eudesmanolide 1 and a new aromatic derivative 2, which were obtained from this plant. Compound 1 was isolated as colorless gum, [(]+128.4 (c 0.43, CHCl3). Its EIMS revealed a molecular ion peak m/z 248. Together with the support …     

A New Eudesmanoilde from Carpesium macrocephalum

A new eudesmanoilde was isolated from the aerial parts of Carpesium macrocephalum. Its structure was elucidated as 2α-acetoxy-11αH-eudesma-4-en-12,8β-olide by spectral methods.