Selected Compounds Structurally Related to Acyclic Sesquiterpenoids and Their Antibacterial and Cytotoxic Activity

Bonikowski, Radosław; Świtakowska, Paulina; Sienkiewicz, Monika; Zakłos‐Szyda, Małgorzata

doi:10.3390/molecules200611272

Cited by 17 publications

(10 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This peak identifies the compound Q which is farnesyl acetate which has the name 3,7,11trimethyl-1,6,10-dodecatrien-3-ol. This Q compound has biological activity as an antibacterial against S. aureus, E. faecalis, E. faecium, E. coli, K. pneumoniae and A. baumannii [11].…”

Section: Resultsmentioning

confidence: 99%

Identification and Prediction of Potential Drug-like Compounds From Ruku-Ruku Leaves (Ocimum tenuiflorum Linnen) in West Sumatera

Parbuntari¹,

Etika²,

Mulia³

2020

Proceedings of the International Conference on Biology, Sciences and Education (ICoBioSE 2019)

View full text Add to dashboard Cite

Ruku-ruku leaves are one of the natural resources in West Sumatra. However, the use of ruku-ruku leaves nowadays has only been used to enrich the taste of cuisine such as fish curry dishes. The distinctive odor of the ruku-ruku leaves can eliminate the fishy odor in the fish. This distinctive odor comes from secondary metabolite compounds on the leaves of the ruku-ruku. Based on previous research, the content of secondary metabolites can be differentiated from one region to another. In fact, to maximise its function, secondary metabolites are first identified and tested for biological activity. Therefore, this study identified secondary metabolites in the ruku-ruku leaves. The results showed that there were about 17 secondary metabolite compounds present in the ruku-ruku leaves. Limonnen, geranyl acetate, and citronellal are the three compounds that have the highest percentage in ruku-ruku leaves, respectively, 59.04%, 14.80%, and 7.81%. In addition, secondary metabolites present in the ruku-ruku leaves have biological activities such as antibacterial properties.

show abstract

Section: Resultsmentioning

confidence: 99%

Identification and Prediction of Potential Drug-like Compounds From Ruku-Ruku Leaves (Ocimum tenuiflorum Linnen) in West Sumatera

Parbuntari¹,

Etika²,

Mulia³

2020

Proceedings of the International Conference on Biology, Sciences and Education (ICoBioSE 2019)

View full text Add to dashboard Cite

show abstract

“…On the other hand, Bonikowski et al studied the antibacterial and cytotoxic effects of 30 components which are structurally related to geranyl acetone, nerolidol, farnesal, farnesol, and farnesyl acetate were obtained. The authors stated that these components have negligible toxicity on various human cell lines and may have the potential to be used safely (Bonikowski et al, 2015). In another study, the effects of farnesol on HeLa human cervical cancer cells were investigated.…”

Section: Discussionmentioning

confidence: 99%

“…Farnesol also exerts a growth inhibitory effect and increases the formation of reactive oxygen species (ROS) (Joo et al, 2015). On the other hand, authors stated that these components have negligible toxicity on various human cell lines and may have the potential to be used safely (Bonikowski et al, 2015). In another study, the effects of farnesol on HeLa human cervical cancer cells were investigated.…”

Section: Discussionmentioning

confidence: 99%

The investigation of in vitro effects of farnesol at different cancer cell lines

Öztürk

Feyzullazade

Dag

et al. 2022

Microscopy Res & Technique

View full text Add to dashboard Cite

Farnesol (trans, trans-3,7,11-trimethyl-2,6,10-dodecatriene-1-ol) is an essential oil component that can be found in a variety of plants. In this study, in vitro effects of farnesol on human lung cancer A549 cell line, colon adenocarcinoma (Caco-2) cell line and healthy human lung epithelial BEAS-2B cell lines, WST-1 cytotoxicity test, dual staining of cell survival (DAPI-PI) analysis, micronucleus test, and transmission electron microscopy (TEM). Farnesol acted in a concentration-dependent manner at the dose ranges studied for cancer cell lines, and while at certain doses it reduced proliferation, interestingly at higher concentrations it induced growth more than the control. In the healthy BEAS-2B cell line, it was tested over a wide range of doses and at all studied concentrations, it did not suppress cellular growth, but rather increased. This seems promising in that farnesol harms cancer cell lines but does not cause significant damage to healthy cells. Obtained TEM data after treatment with farnesol at IC50 dose showed both autophagic and apoptotic findings in cancer cell lines compared to control, and normal findings exhibited in BEAS-2B cell line, cell survival, and micronucleus analyzes showed the presence of apoptotic findings and chromosomal damage as a result of farnesol application in cancer cell lines. Research Highlights• Farnesol has dose-dependent effects on human lung cancer and colon adenocarcinoma cell lines, with no significant damaging effects on healthy human lung epithelial cell lines.• TEM, cell survival, and micronucleus findings support the findings of autophagic, apoptotic, and chromosomal damage on cancer cell lines.

show abstract

“…Our findings of antilymphoma activity of terpenes isolated from PEAm are consistent with previously published reports. Specifically, the authors of [ 44 ] found that sesquiterpene FA induced cytotoxicity against the HL-60 cell line [ 44 ]. In addition, researchers have found that Gg exhibits important chemopreventive and suppressive ac-tivities on cancer cell lines by arresting the cell cycle in the G1 phase and inducing the down-expression of cyclin D1 and induced apoptosis by activating caspases 8, 9, and 3 in cell lines DU145 and DLD1 [ 45 , 46 , 47 , 48 ].…”

Section: Discussionmentioning

confidence: 99%

Understanding the Antilymphoma Activity of Annona macroprophyllata Donn and Its Acyclic Terpenoids: In Vivo, In Vitro, and In Silico Studies

et al. 2022

View full text Add to dashboard Cite

Annona macroprophyllata Donn (A. macroprophyllata) is used in traditional Mexican medicine for the treatment of cancer, diabetes, inflammation, and pain. In this work, we evaluated the antitumor activity of three acyclic terpenoids obtained from A. macroprophyllata to assess their potential as antilymphoma agents. We identified the terpenoids farnesyl acetate (FA), phytol (PT) and geranylgeraniol (Gg) using gas chromatography–mass spectroscopy (GC-MS) and spectroscopic (1H, and 13C NMR) methods applied to petroleum ether extract of leaves from A. macroprophyllata (PEAm). We investigated antitumor potential in Balb/c mice inoculated with U-937 cells by assessing brine shrimp lethality (BSL), and cytotoxic activity in these cells. In addition, to assess the potential toxicity of PEAm, FA, PT and Gg in humans, we tested their acute oral toxicity in mice. Our results showed that the three terpenoids exhibited considerable antilymphoma and cytotoxic activity. In terms of lethality, we determined a median lethal dose (LD50) for thirteen isolated products of PEAm. Gg, PT and AF all exhibited a higher lethality with values of 1.41 ± 0.42, 3.03 ± 0.33 and 5.82 ± 0.58 µg mL−1, respectively. To assess cytotoxic activity against U-937 cells, we calculated the mean cytotoxic concentration (CC50) and found that FA and PT were closer in respect to the control drug methotrexate (MTX, 0.243 ± 0.007 µM). In terms of antilymphoma activity, we found that FA, PT and Gg considerably inhibited lymph node growth, with median effective doses (ED50) of 5.89 ± 0.39, 6.71 ± 0.31 and 7.22 ± 0.51 mg kg−1 in females and 5.09 ± 0.66, 5.83 ± 0.50 and 6.98 ± 0.57mg kg −1 in males, respectively. Regarding acute oral toxicity, we classified all three terpenoids as category IV, indicating a high safety margin for human administration. Finally, in a molecular docking study of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, we found binding of terpenoids to some amino acids of the catalytic site, suggesting an effect upon activity with a resulting decrease in the synthesis of intermediates involved in the prenylation of proteins involved in cancer progression. Our findings suggest that the acyclic terpenoids FA, PT, and Gg may serve as scaffolds for the development of new treatments for non-Hodgkin’s lymphoma.

show abstract

Selected Compounds Structurally Related to Acyclic Sesquiterpenoids and Their Antibacterial and Cytotoxic Activity

Cited by 17 publications

References 19 publications

Identification and Prediction of Potential Drug-like Compounds From Ruku-Ruku Leaves (Ocimum tenuiflorum Linnen) in West Sumatera

Identification and Prediction of Potential Drug-like Compounds From Ruku-Ruku Leaves (Ocimum tenuiflorum Linnen) in West Sumatera

The investigation of in vitro effects of farnesol at different cancer cell lines

Understanding the Antilymphoma Activity of Annona macroprophyllata Donn and Its Acyclic Terpenoids: In Vivo, In Vitro, and In Silico Studies

Contact Info

Product

Resources

About