A Bioactive Triterpene from Laggera pterodonta (Asteraceae) (DC.) Sch. Bip (original) (raw)
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1 Bioactive Terpenoid. NJCR 2009
Laggera pterodonta (DC.) Sch. Bip. aerial part was extracted successively with hexane, ethyl acetate and methanol. The ethyl acetate extract was subjected to chromatography to give a pentacyclic triterpenoid ester which was identified as taraxasteryl acetate based on spectroscopic evidence. The triterpenoid exhibited antimicrobial activity against Staphylococcus aureus, Klebsiella pneumoniae, Klebsiella ozaenae, Bacillus cereus, Shigella dysenteriae, Escherica.coli and Streptococcus faecalis with MICs ranging from 25-50µg/ml. This is the first time taraxasteryl acetate has been isolated from the genus, Laggera.
Further sesquiterpenoids and phenolics from Taraxacum officinale
Fitoterapia, 2000
From roots of Taraxacum flavostylum and Taraxacum lucidum, the species included in the section Taraxacum F. H. Wigg. of the genus Taraxacum F. H. Wigg., eight sesquiterpene lactones, including taraxinic acid (1) and 11β,13dihydrotaraxinic acid (2), taraxinic acid β-glucopyranosyl ester (3) and its 11β,13-dihydroderivative (4), ainslioside (5), deacetylmatricarin (6), 3-epi-11β,13-dihydrodeacylcynaropicrin (7) and ixerin D (8) together with six phenolic metabolites (9-14) were isolated. 3-Epi-11β,13-dihydrodeacylcynaropicrin (7), 3-hydroxy-1-(4hydroxy-3-methoxyphenyl)-1-propanone (9) and 5-methoxy-eugenyl-4-O-β-glucopyranoside (11) were found for the first time in Taraxacum spp. Compounds 1-14 were isolated from T. flavostylum roots, whereas only three germacranolides (3-5), a guaianolide (8) and dihydrosyringin (13) were present in the extract from T. lucidum. Structures of the compounds were elucidated based on spectroscopic data. In vitro cytotoxic activity of taraxinic acid (1) and its derivatives (2-4) against three human melanoma cell lines (A375, HTB140 and WM793), human normal keratinocytes (HaCaT), human normal prostate epithelial cells (PNT-2), and human prostate carcinoma cell line (DU145) was also examined in this study.
Spatula DD - Peer Reviewed Journal on Complementary Medicine and Drug Discovery, 2011
A new pentacyclic triterpenoid glucoside, together with fourteen known compounds, was isolated from the roots of Combretum racemosum (Combretaceae). The structure of the new compound was established as 28-O--D-glucopyranosyl-2,3,21,23-tetrahydroxyolean-18en-28-oate (1) on the basis of detailed spectroscopic data including MS, 1D, and 2D NMR. The inhibitory activity of compounds 1-15 against promyelocytic leukemia HL-60 and human erythromyeloblastoid leukemia K562 cell lines was evaluated. Compounds 11 (3-O-β-acetylursolic acid), 14 (betulinic acid), and 15 (quadranoside II) exhibited significant cytotoxicity, with IC 50 values of 13 to 50 µM. Among the isolated triterpenes, compounds 1, 3 (arjungenin), 5 (terminolic acid), and 11 exhibited moderate antibacterial activity against Staphylococcus aureus, Escherichia coli and Enterococcus faecalis (MICs within a range of 64 and 256 µg/mL). Highlights ►A new pentacyclic triterpenoid glucoside was isolated from Combretum racemosum. ►Four triterpenes isolated from this plant showed antibacterial activity. ►Three triterpenes showed cytotoxic activity against HL-60 and K562 cells.
2018
Clerodendrum capitatum used locally in the treatment of cough and respiratory tract infection was investigated for antimicrobial and anti-tubercular activities. A lanostane type triterpene carboxylic acid (1) and a lupane type triterpenoid (2) were isolated from the ethyl acetate soluble fraction of the leaves of Clerodendrum capitatum. The structures of the compounds were elucidated based on analysis of their spectral data, including 1H, 13C and 2D NMR and by comparison of the data with those reported in the literature. Compound 1 inhibited the growth of Mycobacterium bovis (BCG) at a minimum inhibitory concentration (MIC) of 250 µg/mL. The compounds were also active against 9 out of 12 tested microorganisms including; Bacillus subtillis, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans and two resistant strains (vancomycin resistant entrococci (VRE) and methicillin resistant Staphylococcus aureus (MRSA)). The zones of inhibition (ZI) ranged between 20 and 29 mm agai...
Natural Product Research, 2020
The chemical studies of roots and aerial parts of Taraxacum portentosum Kirschner & St ep anek, a member of the section Palustria (H. Lindb.) Dahlst. (Asteraceae), led to the isolation of one new eudesmanolide and 13 known compounds, including five sesquiterpenoids: taraxinic acid, 11b,13-dihydrotaraxinic acid, taraxinic acid b-glucopyranosyl ester and its 11b,13-dihydroderivative, ixerin D, one apocarotenoidloliolide and seven phenolics: scopoletin, 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone, methyl p-hydroxyphenylacetate, 5-methoxy-eugenyl-4-O-b-glucopyranoside, syringin, dihydroconiferin, and dihydrosyringin. Their structures were established by 1 H NMR. The new compound was characterized as 3-oxo-4bH-11,13-eudesmen-12,6-olide-8-O-b-glucopyranoside based on spectroscopic data (1 D and 2 D NMR) and HRESI mass spectrometry.
Antibacterial and cytotoxic triterpenoids from Lantana viburnoides ssp viburnoides var kisi
Spatula DD - Peer Reviewed Journal on Complementary Medicine and Drug Discovery, 2011
A new pentacyclic triterpenoid glucoside, together with fourteen known compounds, was isolated from the roots of Combretum racemosum (Combretaceae). The structure of the new compound was established as 28-O--D-glucopyranosyl-2,3,21,23-tetrahydroxyolean-18en-28-oate (1) on the basis of detailed spectroscopic data including MS, 1D, and 2D NMR. The inhibitory activity of compounds 1-15 against promyelocytic leukemia HL-60 and human erythromyeloblastoid leukemia K562 cell lines was evaluated. Compounds 11 (3-O-β-acetylursolic acid), 14 (betulinic acid), and 15 (quadranoside II) exhibited significant cytotoxicity, with IC 50 values of 13 to 50 µM. Among the isolated triterpenes, compounds 1, 3 (arjungenin), 5 (terminolic acid), and 11 exhibited moderate antibacterial activity against Staphylococcus aureus, Escherichia coli and Enterococcus faecalis (MICs within a range of 64 and 256 µg/mL). Highlights ►A new pentacyclic triterpenoid glucoside was isolated from Combretum racemosum. ►Four triterpenes isolated from this plant showed antibacterial activity. ►Three triterpenes showed cytotoxic activity against HL-60 and K562 cells.
Turkish Journal of Chemistry, 2020
Introduction The genus Laggera Sch. Bip. ex Benth. & Hook., belonging to the Asteraceae (Compositae) plant family, has about 20 species, distributed mainly in sub-Saharan Africa and southeastern Asia [1]. Most of its species are often used in folk and traditional medicines for the treatment of inflammation, jaundice, leukemia, bronchitis, removing phlegm, and bacterial diseases, and their leaves, as well as aerial parts, have been reported to have antiinflammatory, antibacterial, antiviral, antioxidant, hepatoprotective, insecticidal, antifungal, anthelmintic, sedative, antituberculosis, and antidiarrheal properties [2]. The essential oils (EOs) of Laggera species have also been reported to exhibit antibacterial, antifungal, antioxidant, larvicidal, and insecticidal activities [3-5]. To date, the chemical constituents of the extracts and/or EOs of only 8 plants of the genus Laggera have been reported from 13 countries [2]. However, many bioactive compounds with many-sided activities have been identified from these plants, which has drawn researchers to further investigate Laggera species [1,2]. The genus is rich in flavonoids, cyclitols, monoterpenes, and sesquiterpenes (eremophilanes and eudesmanes). Flavones, fatty acids, and their derivatives, sterols (stigmasterol and β-sitosterol), phenolic acids like 2-hydroxybenzoic acid, and phytotoxic thymol derivatives, such as 3-hydroxythymoquinone and 5-acetoxy-2hydroxythymol, have also been reported from extracts of the plants of the genus Laggera [1,2,6,7]. 2,5-dimethoxy-pcymene, α-humulene, β-caryophyllene, γ-eudesmol, 10-epi-γ-eudesmol, and juniper camphor are the most frequent chemical compounds in the EOs of these plants, and the former (oxygenated monoterpene) is the most abundant, as well as the most dominant constituent of many of the EOs [2]. Laggera tomentosa Sch. Bip. ex Oliv. et Hiern, an annual fragrant subshrub or bushy herb, is an endemic medicinal plant of Ethiopia. Its leaves are used to treat various diseases, including the common cold, cough, flu, rabies, leech infestation, dysentery, and febrile illness and headaches, while the aerial parts are used for the treatment of toothache, swelling, and
Sesquiterpenoids and phenolics from Taraxacum hondoense
Fitoterapia, 2005
Eleven sesquiterpene lactones, including the new guaianolide 11h-hydroxydeacetylmatricarin-8-O-h-glucopyranoside, along with four known phenolic glucosides were isolated from Taraxacum hondoense. The compounds were characterized by spectral methods.
Taraxastane and Lupane Triterpenoids from the Bark of Manilkara zapota
International Research Journal of Pure and Applied Chemistry, 2015
Discovering new lead compounds against cancer and bacterial infections is a crucial step to ensuring a sustainable global pipeline for new effective drugs. This study focus on the isolation of secondary metabolites of methanol extract from the bark of Manilkara zapota (Sapotaceae) a Cameroonian medicinal plant. Study Design: According to the literature, plants of the genus Manilkara are potential sources of antibacterial and anticancer secondary metabolites. Methodology: The air-dried and powdered bark (4.0 kg) of M. zapota was extracted at room temperature for 72 h with a methanol. The extract was concentrated to dryness under vacuum and the residue was subjected to repeated column chromatographic separation. The structures of the Toze et al.; IRJPAC, 7(4): 157-164, 2015; Article no.IRJPAC.2015.064 158 isolates were established by means of spectroscopic methods. These compounds were screened in vitro for their activity against bacterial and human Caucasian prostate adenocarcinoma cell line PC-3. Results: Two new pentacyclic triterpenoids, 3-acetyltaraxer-14-en-12-one (1) and 3-hydroxy-7oxolup-20(29)-en-28-oic acid (4), together with eleven known compounds were isolated from the methanol extract from the bark of Manilkara zapota. The structures of all compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral (EI and ESI) data and comparison with previously known analogs. The agar diffusion test delivered low to missing antimicrobial activities, corresponding with MICs > 1mg/ml. In addition, compounds 1, 4-7, 11 and 12 displayed moderate cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3 with IC 50 value ranging from 14.1-30.6 g/ml, while compounds 2 and 3 showed weak cytotoxic activity with an IC 50 value of 61.2-62.5 g/ml, compared to the standard doxorubicin (IC 50 = 0.9 µg/ml). Conclusion: Two new triterpenoids were isolated, some isolated compounds displayedmissing or low activities against bacterial, plant pathogen oomycetes and moderate cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3.