Vicanicin
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| Category | Others |
| Catalog number | BBF-05142 |
| CAS | 33211-22-2 |
| Molecular Weight | 383.22 |
| Molecular Formula | C18H16Cl2O5 |
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Description
Vicanicin is a depsidone isolated from the lichen Teloschistesflavicans (Sw.) Norm. Vicanicin can induce apoptosis of DU-145 and LNCaP cells.
Specification
| Synonyms | 2,7-Dichloro-3-hydroxy-8-methoxy-1,4,6,9-tetramethyl-11H-dibenzo[b,e][1,4]dioxepin-11-one |
| IUPAC Name | 2,8-dichloro-9-hydroxy-3-methoxy-1,4,7,10-tetramethylbenzo[b][1,4]benzodioxepin-6-one |
| Canonical SMILES | CC1=C2C(=C(C(=C1Cl)O)C)OC3=C(C(=C(C(=C3OC2=O)C)OC)Cl)C |
| InChI | InChI=1S/C18H16Cl2O5/c1-6-10-14(8(3)13(21)11(6)19)24-16-7(2)12(20)15(23-5)9(4)17(16)25-18(10)22/h21H,1-5H3 |
| InChI Key | DJIUVCGPONSSSV-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 563.7±50.0°C (Predicted) |
| Density | 1.399±0.06 g/cm3 (Predicted) |
Reference Reading
1. Cytotoxic activity and antioxidant capacity of purified lichen metabolites: an in vitro study
Fabrizia Brisdelli, Mariagrazia Perilli, Doriana Sellitri, Marisa Piovano, Juan A Garbarino, Marcello Nicoletti, Argante Bozzi, Gianfranco Amicosante, Giuseppe Celenza Phytother Res. 2013 Mar;27(3):431-7. doi: 10.1002/ptr.4739. Epub 2012 May 25.
The purpose of this study was to investigate the effects of six lichen metabolites (diffractaic acid, lobaric acid, usnic acid, vicanicin, variolaric acid, protolichesterinic acid) on proliferation, viability and reactive oxygen species (ROS) level towards three human cancer cell lines, MCF-7 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and HCT-116 (colon carcinoma). Cells were treated with different concentrations (2.5-100 μM) of these compounds for 48 h. In this comparative study, our lichen metabolites showed various cytotoxic effects in a concentration-dependent manner, and usnic acid was the most potent cytotoxic agent, while variolaric acid did not inhibit the proliferation of any of the three cell lines used. All tested lichen compounds did not exhibit free radical scavenging activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The lichen metabolites did not significantly increase the intracellular ROS level and did not prevent oxidative injury induced by t-butylhydroperoxide in HeLa cells. To better clarify the mechanism(s) of cytotoxic effect induced by protolichesterinic acid in HeLa cells, we investigated apoptotic markers such as condensation and fragmentation of nuclear chromatin and activation of caspase-3, 8 and 9. Our results revealed that the antiproliferative activity of 40 μM protolichesterinic acid in HeLa cells is related to its ability to induce programmed cell death involving caspase-3, 8 and 9 activation.
2. A New Depsidone from Teloschistes flavicans and the Antileukemic Activity
Angga Sanjaya, Avidlyandi Avidlyandi, Morina Adfa, Masayuki Ninomiya, Mamoru Koketsu J Oleo Sci. 2020 Dec 1;69(12):1591-1595. doi: 10.5650/jos.ess20209. Epub 2020 Nov 12.
Lichens produce a variety of secondary metabolites that could be potential sources of pharmaceutically useful chemicals. However, only a limited number of lichen metabolites have been investigated for their biological significance. The objective of this study was to identify the potential compounds responsible for the antileukemic activity of lichen Teloschistes flavicans. Among three fractions (n-hexane, EtOAc, and MeOH-H2O), the ethyl acetate (EtOAc) fraction of T. flavicans methanolic extract showed the strongest inhibition in the HL-60 cell line. Additionally, the EtOAc fraction was further purified to obtain a new depsidone, 2,7-dichloro-3,8-dimethoxy-1,6,9-trimethyl-11H-dibenzo[b,e][1,4]dioxepin-11-one, named as flavicansone, along with rhizonic acid, parietin, and vicanicin. Flavicansone demonstrated the most significant inhibitory action against cell proliferation among the four isolated compounds.
3. Effect of vicanicin and protolichesterinic acid on human prostate cancer cells: role of Hsp70 protein
A Russo, S Caggia, M Piovano, J Garbarino, V Cardile Chem Biol Interact. 2012 Jan 5;195(1):1-10. doi: 10.1016/j.cbi.2011.10.005. Epub 2011 Oct 29.
With the aim of identifying novel agents with antigrowth and pro-apoptotic activity on prostate cancer cells, in the present study, we evaluated the effect of five lichen secondary metabolites the depsides atranorin (1), diffrattaic (2) and divaricatic (3) acids, the depsidone vicanicin (4) and the protolichesterinic acid (5) on cell growth in androgen-sensitive (LNCaP) and androgen-insensitive (DU-145) human prostate cancer cells. The cell viability was measured using MTT assay. LDH release, a marker of membrane breakdown, was also measured. For the detection of apoptosis, the evaluation of DNA fragmentation (COMET assay) and caspase-3 activity assay were employed. The expression of Bcl-2, Bax, TRAIL, COX-2, NOS2 and Hsp70 proteins was detected by western blot analysis. Generation of reactive oxygen species was measured by using a fluorescent probe. It was observed that atranorin (1), diffrattaic (2) and divaricatic (3) acids showed a lower activity inhibiting the prostate cancer cells only at more high concentrations (25 and 50μM). Whereas compounds vicanicin (4) and protolichesterinic acid (5) showed a dose-response relationship in the range of 6.25-50μM concentrations in DU-145 and LNCaP cells, activating an apoptotic process. The novel finding, in the present study, is that apoptosis induced by these compounds appears to be mediated, at least in part, via the inhibition of Hsp70 expression, that may be correlated with a modulation of redox-sensitive mechanisms. The combination of vicanicin (4) and protolichesterinic acid (5) with other anti-prostate cancer therapies could be considered a promising strategy that warrants further in vivo evaluation.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
