scholarly journals Trichilianones A-D, Novel Cyclopropane-Type Limonoids from Trichilia adolfi

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1019
Author(s):  
Ivan Limachi ◽  
Mariela Gonzalez-Ramirez ◽  
Sophie Manner ◽  
Juan C. Ticona ◽  
Efrain Salamanca ◽  
...  

The fractionation of an ethanol extract of the bark of Trichilia adolfi yielded four novel limonoids (trichilinones A-D, 1–4), with five fused rings and related to the hortiolide-type limonoids. Starting with an ε-lactone, which is α,β-unsaturated in trichilinones A and D (1 and 4), attached to a tetrahydrofuran ring that is connected to an unusual bicyclo [5.1.0] hexane system, joined with a cyclopentanone with a 3-furanyl substituent [(2-oxo)-furan-(5H)-3-yl in trichilinone D (4)], the four compounds isolated display a new 7/5/3/5/5 limonoid ring system. Their structures were established based on extensive analysis of NMR spectroscopic data. As the crude extract possessed anti-leishmanial properties, the compounds were assayed for cytotoxic and anti-parasitic activities in vitro in murine macrophages cells (Raw 264.7) and leishmania promastigotes (L. amazoniensis and L. braziliensis), respectively. The compounds showed moderate cytotoxicity (approximately 70 μg/mL), but are not responsible for the leishmanicidal effect of the extract.


Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3070
Author(s):  
Mariela Gonzalez-Ramirez ◽  
Ivan Limachi ◽  
Sophie Manner ◽  
Juan C. Ticona ◽  
Efrain Salamanca ◽  
...  

In addition to the trichilianones A–D recently reported from Trichilia adolfi, a continuing investigation of the chemical constituents of the ethanol extract of the bark of this medicinal plant yielded the five new limonoids 1–5. They are characterized by having four fused rings and are new examples of prieurianin-type limonoids, having a ε-lactone which in 4 and 5 is α, β- unsaturated. The structures of the isolated metabolites were determined by high field NMR spectroscopy and HR mass spectrometry. The new metabolites were shown to have the ε-lactone fused with a tetrahydrofuran ring which is connected to an oxidized hexane ring joined with a cyclo-pentanone having a 3-furanyl substituent. As the crude extract possesses antileishmanial activity, the compounds were assayed for cytotoxic and antiparasitic activities in vitro in murine macrophage cells (raw 264.7 cells) and in Leishmania amazoniensis as well as L. braziliensis promastigotes. Metabolites 1–3 and 5 showed moderate cytotoxicity (between 30–94 µg/mL) but are not responsible for the antileishmanial effect of the extract.





2021 ◽  
Vol 12 ◽  
Author(s):  
Gaoran Liu ◽  
Ruiyun Huo ◽  
Yanan Zhai ◽  
Ling Liu

Three new secondary metabolites pestalothenins A–C (1–3), including two new humulane-derived sesquiterpeniods (1 and 2) and one new caryophyllene-derived sesquiterpeniod (3), together with five known compounds (4–8) were isolated from the crude extract of the plant endophytic fungus Pestalotiopsis theae (N635). Their structures were elucidated by the extensive analyses of HRESIMS and NMR spectroscopic data. The absolute configurations of 1–3 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. The cytotoxic effects of these compounds were evaluated in vitro. Compound 6 showed moderate cytotoxicity against T24 and MCF7 cell lines. In addition, compounds 1–8 were also evaluated for antibacterial activity.



Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2202 ◽  
Author(s):  
Charinya Khamphukdee ◽  
Orawan Monthakantirat ◽  
Yaowared Chulikhit ◽  
Suradet Buttachon ◽  
Michael Lee ◽  
...  

The previously unreported flavone glycoside, demethyltorosaflavone B (2) and the E-propenoic acid substituted flavone, torosaflavone E (3a), were isolated together with nine previously reported metabolites, including indole-3-carbaldehyde, oleanonic acid, vanillic acid, p-hydroxybenzoic acid, altheranthin (1a), alternanthin B (1b), demethyltorosaflavone D (3b), luteolin 8-C-E-propenoic acid (4) and chrysoeriol 7-O-rhamnoside (5), from the ethanol extract of the aerial part of Althernanthera philoxeroides. The crude ethanol extract was evaluated for its in vitro estrogenic activity in MCF-7 breast cancer cell line. The crude ethanol extract was also investigated in vivo for its antidepressant-like effects on ovariectomized mice using tail suspension and forced swimming tests, while its effect on the locomotor activity was evaluated by a Y-maze test. The effect of the crude extract on the serum corticosterone level, size and volume of uterus of the ovariectomized mice were also investigated. The expression of the mouse cyclic adenosine monophosphate (cAMP) response element-binding protein (CREB), brain-derived neurotrophic factor (BDNF) and β-actin mRNAs in hippocampus and frontal cortex was also evaluated, using semiquantitative reverse transcription-polymerase chain reaction. The crude extract and the isolated compounds 1a, 1b, 3a, 3b and 5, were evaluated for their inhibitory effects on monoamine oxidases (MAOs)-A and -B.



Author(s):  
Novie E. Mauliku ◽  
Hendro W. ◽  
Suharyo Hadi Saputro ◽  
Tri N. Kristina

Objective: This study aimed to evaluate the antitubercular activity of extracts and compounds isolated of Morinda citrofolia Linn (noni) against Mycobacterium tuberculosis strains (H37Rv) with a dose of 10 mg/ml, 20 mg/ml, 30 mg/ml and 40 mg/ml. Methods: The noni fruits was extracted using 96% ethanol. A crude ethanol extract of noni tested by phytochemical fractionation to obtain flavonoids, alkaloids, scopoletin, and anthraquinone. Extract and active compounds of noni testing antibacterial activity against tuberculosis (H37RV) bacterial with a dose of 10 mg / ml, 20 mg / ml, 30 mg / ml and 40 mg / ml. This study was performed in vitro with laboratory-based experimental study. Statistical analysis was performed by analysis of variance.Results: Compounds of noni shown to have antitubercular activity in inhibiting the growth of MDR TB bacteria at various doses compared to controls (p = 0.00). The mean number of bacterial colonies on the MDR TB crude ethanol extract (59.0± 60.51), alkaloids (64.8 ± 49.36), anthraquinone (69.5 ± 50.40), flavonoids (72.9 ± 58.7), scopoletin (95.9 ± 33.3) and negative controls (189.3 ± 35.19). Crude extract, alkaloids, anthraquinones, and flavonoid have highly bactericidal inhibition than scopoletin and negative control. The exhibited minimum inhibitory concentration (MIC) against M. Tuberculosis on the compound of the noni fruit is at a dose of 40 mg / ml Conclusion: All compounds and extract of noni fruits represents a potent active anti-TB against M. tuberculosis strains. An crude extract of  noni was the most active compound against M. tuberculosis strains (H37RV). 



Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 56
Author(s):  
Yan Chen ◽  
Ge Zou ◽  
Wencong Yang ◽  
Yingying Zhao ◽  
Qi Tan ◽  
...  

One new diterpenoid, diaporpenoid A (1), two new sesquiterpenoids, diaporpenoids B–C (2,3) and three new α-pyrone derivatives, diaporpyrones A–C (4–6) were isolated from an MeOH extract obtained from cultures of the mangrove endophytic fungus Diaporthe sp. QYM12. Their structures were elucidated by extensive analysis of spectroscopic data. The absolute configurations were determined by electronic circular dichroism (ECD) calculations and a comparison of the specific rotation. Compound 1 had an unusual 5/10/5-fused tricyclic ring system. Compounds 1 and 4 showed potent anti-inflammatory activities by inhibiting the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW264.7 cells with IC50 values of 21.5 and 12.5 μM, respectively.



2009 ◽  
Vol 77 (4) ◽  
pp. 1636-1648 ◽  
Author(s):  
John Shanks ◽  
Mary N. Burtnick ◽  
Paul J. Brett ◽  
David M. Waag ◽  
Kevin B. Spurgers ◽  
...  

ABSTRACT Burkholderia mallei, a category B biothreat agent, is a facultative intracellular pathogen that causes the zoonotic disease glanders. The B. mallei VirAG two-component regulatory system activates the transcription of ∼60 genes, including a large virulence gene cluster encoding a type VI secretion system (T6SS). The B. mallei tssM gene encodes a putative ubiquitin-specific protease that is physically linked to, and transcriptionally coregulated with, the T6SS gene cluster. Mass spectrometry and immunoblot analysis demonstrated that TssM was secreted in a virAG-dependent manner in vitro. Surprisingly, the T6SS was found to be dispensable for the secretion of TssM. The C-terminal half of TssM, which contains Cys and His box motifs conserved in eukaryotic deubiquitinases, was purified and biochemically characterized. Recombinant TssM hydrolyzed multiple ubiquitinated substrates and the cysteine at position 102 was critical for enzymatic activity. The tssM gene was expressed within 1 h after uptake of B. mallei into RAW 264.7 murine macrophages, suggesting that the TssM deubiquitinase is produced in this intracellular niche. Although the physiological substrate(s) is currently unknown, the TssM deubiquitinase may provide B. mallei a selective advantage in the intracellular environment during infection.



2014 ◽  
Vol 10 (2) ◽  
Author(s):  
Nadia Naitullah ◽  
Faisal Jamin ◽  
Frengki Frengki ◽  
Maryulia Dewi

This research aimed to determine the effect of ethanol extract of Impatiens balsamina Linn leaves on the growth of Candida albicans in vitro. One kilogram of Impatiens balsamina leaves which grows in Aceh was used. The leaves were washed, dried and blended into powder. The powder was then extracted with ethanol, filtrated, and evaporated. The crude extract was then made into serial concentration of 100, 75, 50, and 25%. The test of the effect of giving ethanol extract in Impatiens balsamina Linn is determined by the Kirby-Bauer disc diffusion method. Results showed that inhibition zones for 0, 25, 50, 75, and 100% were 0.0, 8.66±1.53, 11.66±1.55, 13.66±1.52, and 6±5.29 consecutively. It can be concluded that the ethanol extract of Impatiens balsamina Linn leaves± inhibit the growth of Candida albicans.Key words: Candida albicans, balsamina leaf, Impatiens balsamina Linn, extract



2013 ◽  
Vol 16 (1) ◽  
pp. 33-37 ◽  
Author(s):  
Md Arafat Hossan ◽  
Mohammed Ibrahim ◽  
Md Qamrul Ahsan ◽  
Fahima Aktar ◽  
Md Ruhul Kuddus ◽  
...  

The present study was conducted to investigate the bio-activities of ethanol extract of Etlingera linguiformis (Roxb.) R.M.Sm. as well as to determine the chemical profiles of the extract. The antibacterial and antifungal activities of the crude extract were evaluated by the disc diffusion method against 4 Gram positive and 7 Gram negative pathogenic bacteria and 7 fungi using Ciprofloxacin and Fluconazole as standards, respectively. The minimum inhibitory concentration (MIC) was determined by the serial dilution method. The anti-atherothrombosis activity was assessed by using Streptokinase (SK) as standard. Moreover, the in-vitro anti-inflammatory and membrane stablization tests were performed. In the anti-bacterial and antifungal activity test, the zones of inhibition were found within the range of 10.0-15.0 and 10.0-22.0 mm, respectively. The highest zone of inhibition was obtained against Bacillus cereus (15.0 mm) and Blastomyces dermatitidis (22.0 mm). In the minimum inhibitory concentration (MIC) test the crude extract inhibited the growth of Blastomyces dermatitidis significantly at 31.2 ?g/ml. In the anti-atherothrombosis activity test, the extract revealed moderate clot lysis by 15.15%. Moreover, the extract produced inhibition of protein denaturation and haemolysis by 34% and 38.98% in the in vitro antiinflammatory and membrane stablization tests. Preliminary phytochemical screenings of the crude extractives demonstrated the presence of alkaloids, steroids, tannins, reducing sugars and gums. The extract also exhibited good biological activities. Therefore, the plant should be subjected to systematic bioactivity guided isolation in order to obtain the active molecules. DOI: http://dx.doi.org/10.3329/bpj.v16i1.14488 Bangladesh Pharmaceutical Journal 16(1): 33-37, 2013



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