Further ineupatorolide-like germacranolides from Inula cuspidata

Bohlmann, Ferdinand; Singh, Pahup; Jakupovic, Jasmin

doi:10.1016/0031-9422(82)80034-4

Cited by 43 publications

(20 citation statements)

References 6 publications

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“…Compounds 8 – 14 and the known compounds divaricin A–C 8 are assigned as subtype II (named 2 α ,5 α -epoxygermacranolide), having a 7,8- α -methylene- γ -lactone ring and the 2 α ,5 α -hemiacetal group. The known compounds incaspitolide A–C 22 , 23 and eight germacranolides we previously reported from C. divaricatum 12 are classified as subtype III (named 9-oxo-germacranolide) with structural features of one 6,7- α -methylene- γ -lactone ring and the 9-ketone group. Compounds 15 – 20 represent subtype IV (named 3-oxo-germacranolide), possessing a 6,7- α -methylene- γ -lactone ring and the 9-ketone group.…”

Section: Introductionmentioning

confidence: 99%

Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum

Zhang

Chen

et al. 2018

Sci Rep

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Five sets of germacrane isomers (1/8/17, 2/7/10/11/13/16/18, 3/4/5/14/20, 6/12/15, and 9/19) with different skeletal types, including seven new ones (1–3, 8–9, and 15–16) were isolated from the whole plant of Carpesium divaricatum. Among them, there are six pairs of stereoisomers (1/8, 2/13, 4/14, 6/12, 7/11 and 10/11). The planar structures and relative configurations of the new compounds were elucidated by detailed spectroscopic analysis. The absolute configurations of 4, 10, 11, and 17 were established by circular dichroism (CD) spectra and X-ray crystallographic analyses, and the stereochemistry of the new compounds 1–3, 8–9, and 15–16 were determined by similar CD spectra with 4, 10, 11, and 17, respectively. The confusion in the literature about subtypes I and II of germacranolides was clarified in this paper. The NMR data of 10–11, and the absolute configurations of the known compounds 4–6, 13–14, and 17–20 were reported for the first time. Compounds 13, 17, and 18 showed cytotoxicity against human cervical (HeLa), colon (LoVo) and stomach cancer (BGC-823) cell lines with IC50 values in the range 4.72–13.68 μM compared with the control cis-platin (7.90–15.34 μM).

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Section: Introductionmentioning

confidence: 99%

Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum

Zhang

Chen

et al. 2018

Sci Rep

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“…10 Previous chemical investigations revealed the presence of monoterpenoids, sesquiterpenoids, flavonoids and glycosides in the plant. 11 , 12 , 13 In the previous studies different extracts of leaves have been studied for anti-inflammatory activity. 14 The aqueous extracts of stem and whole plant have been recently investigated for anti-inflammatory and hepatoprotective activities.…”

Section: Introductionmentioning

confidence: 99%

Studies on analgesic, anti-inflammatory activities of stem and roots of Inula cuspidata C.B Clarke

Paliwal

Sati

Faujdar

et al. 2017

Journal of Traditional and Complementary Medicine

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The present study was carried out to evaluate analgesic and anti-inflammatory activities in Inula cuspidata stem and root extracts along with heavy metals estimation in stem and root powder.Stem and roots were extracted with chloroform (ICSCE, ICRCE) and methanol (ICSME, ICRME). Acute oral toxicity of all extracts was determined by OECD guidelines 425. Analgesic activity was investigated by using hot plate and acetic acid induced writhing models. Anti-inflammatory activity (acute) of all extracts was evaluated by carrageenan induced paw edema model. In addition, root and stem powder was screened for heavy metals (As, Pb, Cd, Hg) estimation using atomic absorption spectroscopy. In acute toxicity study no mortality was observed when each extract was orally administered with 2.0 g/kg. At the doses (100 and 200 mg/kg) ICRME followed by ICSME showed significant and dose dependent analgesic and anti-inflammatory effects compared with chloroform extracts. The heavy metals concentration in stem and root powders was found to be within the permissible limits as recommended by WHO for herbal raw materials. The findings of the present study validated the folkloric use of Inula cuspidata as analgesic and anti-inflammatory. In addition, the results intimate that heavy metals present in raw material were found to be within the defined limits, and it exhibits that the therapeutic efficacy of plant may not be effected, which can be otherwise possibly effected if the plant sequester high concentration of heavy metals from the polluted environment as well as from the soil rich in pesticides and sewage sludge etc.

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“…Compounds 3 – 4 possessed molecular formulas of C 24 H 34 O 9 and C 23 H 32 O 8 , from their HRESIMS at m/z 489.2108 [M + Na] + , and m/z 459.1971 [M + Na] + , respectively. The 1 H and 13 C NMR data of 3–4 were similar to those of incaspitolide A ( 1 ) 24 , except that the 2′-hydroxy-isobutyryloxy group at C-5 and the angeloyloxy group at C-8 in 3 were observed in place of two isobutyryloxy groups in 1 , and an isobutyryloxy group at C-8 in 1 was replaced by the 2-methylacryloyl group in 4 , respectively. These observations were confirmed by analyses of relevant 1 H- 1 H COSY, HSQC and HMBC data ( Fig.…”

Section: Resultsmentioning

confidence: 59%

“…Compound 1 ( Fig. 1 ) was identified as incaspitolide A ( 1 ) 24 , by comparison of its MS, 1 H NMR data, as well as optical rotation data with reported data. However, its 13 C NMR data have not been reported and absolute configuration has not been determined.…”

Section: Resultsmentioning

confidence: 90%

“…The isobutyryloxy group at C-8 in 1 was placed by a 3-methylbutyry- loxy group in 6 and the 2-methylbutyryloxy group of 7 , respectively. Compounds 6 – 7 have been reported as a mixture from Inula cuspidata 24. Actually, the exact linkage sites of the substituted groups have not been determined in the previous report and the authors speculate the mixture may contain two pairs of mixtures (incaspitolide B and C).…”

Section: Resultsmentioning

confidence: 93%

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New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity

Zhang

et al. 2016

Sci Rep

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Eight highly oxygenated germacranolides (1–8) including four new ones (2–5) were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by NMR experiment and HRESIMS data. The absolute configuration of 1 was established by circular dichroism (CD) method and X-ray diffraction, and the stereochemistry of the new compounds 2–5 were determined by similar CD spectra with 1. Compound 2 is the first hydroperoxyl germacrane from the genus Carpesium. The 13C NMR data of 1, NMR data of 6–7, and their absolute configurations were reported for the first time. Two new compounds (2 and 4) and two known compounds (6 and 8) exhibited potent cytotoxicity against human cervical cancer (HeLa) cells, superior to that of the positive control doxorubicin.

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Further ineupatorolide-like germacranolides from Inula cuspidata

Cited by 43 publications

References 6 publications

Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum

Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum

Studies on analgesic, anti-inflammatory activities of stem and roots of Inula cuspidata C.B Clarke

New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity

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