Fiscalin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00930 |
| CAS | |
| Molecular Weight | 487.55 |
| Molecular Formula | C27H29N5O4 |
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Description
Fiscalin C is a substance P inhibitor produced by Neosartorya fischeri.
Specification
| Synonyms | Scequinadoline B |
| IUPAC Name | (1S,4R)-4-[[(3aR,4R)-4-hydroxy-2,2-dimethyl-1-oxo-3,3a-dihydroimidazo[1,2-a]indol-4-yl]methyl]-1-propan-2-yl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione |
| Canonical SMILES | CC(C)C1C2=NC3=CC=CC=C3C(=O)N2C(C(=O)N1)CC4(C5NC(C(=O)N5C6=CC=CC=C64)(C)C)O |
| InChI | InChI=1S/C27H29N5O4/c1-14(2)20-21-28-17-11-7-5-9-15(17)23(34)31(21)19(22(33)29-20)13-27(36)16-10-6-8-12-18(16)32-24(27)30-26(3,4)25(32)35/h5-12,14,19-20,24,30,36H,13H2,1-4H3,(H,29,33)/t19-,20+,24-,27-/m1/s1 |
| InChI Key | VHQZIMAMLQIPDR-KLGADWMXSA-N |
Reference Reading
1. Cytotoxic activity of Secondary Metabolites from Marine-derived Fungus Neosartorya siamensis in Human Cancer Cells
M Prata-Sena, A A Ramos, S Buttachon, B Castro-Carvalho, P Marques, T Dethoup, A Kijjoa, E Rocha Phytother Res. 2016 Nov;30(11):1862-1871. doi: 10.1002/ptr.5696. Epub 2016 Aug 17.
Compounds isolated from the marine sea fan-derived fungus Neosartorya siamensis (KUFA 0017), namely, 2,4-dihydroxy-3-methylacetophenon (1), chevalone C (2), nortryptoquivaline (4), tryptoquivaline H (6), tryptoquivaline F (7), fiscalin A (8), epi-fiscalin A (9), epi-neofiscalin A (11) and epi-fiscalin C (13) were tested for anti-proliferative activity by MTT assay, DNA damage induction by comet assay, and induction of cell death by nuclear condensation assay on colon HCT116, liver HepG2 and melanoma A375 cancer cell lines. Compounds 2, 4, 8, 9, 11 and 13 presented IC50 values ranging from 24 to 153 μM in the selected cell lines. Cell death was induced in HCT116 by compounds 2, 4 and 8. In HepG2, compounds 4, 8, 9 and 11 were able to induce significant cell death. This induction of cell death is possibly not related to genotoxicity because none of the compounds induced significant DNA damage. These results suggest that selected compounds present an interesting anti-proliferative activity and cell death induction, consequently showing potential (specifically epi-fiscalin C) as future leads for chemotherapeutic agents. Further studies on mechanisms of action should ensue. Copyright © 2016 John Wiley & Sons, Ltd.
2. New pyrazinoquinazoline alkaloids Isolated from a culture of Stenotrophomonas maltophilia QB-77
Sheng-Yan Qian, Cai-Ling Yang, Afsar Khan, Rong-Xiang Chen, Ming-Song Wu, Li Tuo, Qian Wang, Jian-Guo Liu, Gui-Guang Cheng Nat Prod Res. 2019 May;33(9):1387-1391. doi: 10.1080/14786419.2018.1475381. Epub 2018 May 17.
Two new pyrazinoquinazoline alkaloids, epi-fiscalin D (1) and epi-fiscalin E (2), as well as three known analogues, norquinadoline A (3), quinadoline A (4), and fiscalin C (5), were isolated from ethyl acetate extract of the fermentation broth of Stentrophomonas maltophilia QB-77. The structures of new compounds were elucidated on the basis of extensive spectroscopic data analysis including UV, HRESIMS, and 1D and 2D NMR experiments. All the isolated compounds were tested for their in vitro cytotoxicity against five human cancer cell lines (SMMC-7721, MCF-7, HL-60, SW480, and A-549) and antibacterial activities against Bacillus subtilis, Escherichia coli, and Staphylococcus aureus.
3. Can marine-derived fungus Neosartorya siamensis KUFA 0017 extract and its secondary metabolites enhance antitumor activity of doxorubicin? An in vitro survey unveils interactions against lung cancer cells
Alice A Ramos, Bruno Castro-Carvalho, Maria Prata-Sena, Fernanda Malhão, Suradet Buttachon, Tida Dethoup, Anake Kijjoa, Eduardo Rocha Environ Toxicol. 2020 Apr;35(4):507-517. doi: 10.1002/tox.22886. Epub 2019 Dec 5.
Doxorubicin (Dox) is one of the most successful anticancer drugs in use. However, chemoresistance is one of the main limitations that patients face. Therefore, development of new strategies to improve the efficacy of Dox is needed. Marine-derived fungi are especially promising sources of new anticancer compounds. In this work, antitumor activity of crude ethyl extract of the cultures of the marine-derived fungus Neosartorya siamensis KUFA 0017 (NS), combined with Dox, was evaluated in six cancer cell lines. To evaluate possible mechanisms involved in the eventual improvement of Dox's cytotoxicity by NS extract, effects on DNA damage, cell death, ultrastructural modifications, and intracellular accumulation of Dox were assessed. The NS extract demonstrated a significant enhancement of Dox's cytotoxic activity in A549 cells, inducing DNA damage, cell death, and intracellular accumulation of Dox. Additionally, the cytotoxic effect of eight compounds, isolated from this extract, that is, 2,4-dihydroxy-3-methylacetophenone-(C1), nortryptoquivaline-(C2), chevalone C-(C3), tryptoquivaline H-(C4), fiscalin A-(C5), epi-fiscalin-C (C6), epi-neofiscalin A-(C7), and epi-fiscalin A-(C8), alone and combined with Dox was also evaluated in lung cancer cells. The cytotoxic effect of Dox was potentiated by all the isolated compounds (except C1) in A549 cells. Therefore, we concluded that NS extract potentiated cytotoxicity by inhibiting cell proliferation, increasing intracellular accumulation of Dox, and inducing cell death (possibly by an autophagic process). The isolated compounds also enhanced the activity of Dox, supporting the potential of this sort of combination. These data call for further studies to characterize drug interactions and underlying mechanisms.
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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 ╳
