Ilicicolin C
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| Category | Antibiotics |
| Catalog number | BBF-01497 |
| CAS | 22562-67-0 |
| Molecular Weight | 406.94 |
| Molecular Formula | C23H31ClO4 |
| Purity | >95% |
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Description
Ilicicolin C is originally isolated from Cylinddrocladium ilicicola MFC-870. It inhibits Bacillus carbonifera with the concentration of 6 μg/mL and its toxic concentration to Hela cells is 0.2 μg/mL.
Specification
| Synonyms | LL-Z 1272delta; 3-Chloro-4,6-dihydroxy-2-methyl-5-((2E)-3-methyl-5-((1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl)-2-pentenyl)benzaldehyde |
| IUPAC Name | 5-chloro-2,4-dihydroxy-6-methyl-3-[(E)-3-methyl-5-[(1S,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]pent-2-enyl]benzaldehyde |
| Canonical SMILES | CC1CCC(=O)C(C1(C)CCC(=CCC2=C(C(=C(C(=C2O)Cl)C)C=O)O)C)C |
| InChI | InChI=1S/C23H31ClO4/c1-13(10-11-23(5)14(2)7-9-19(26)16(23)4)6-8-17-21(27)18(12-25)15(3)20(24)22(17)28/h6,12,14,16,27-28H,7-11H2,1-5H3/b13-6+/t14-,16+,23+/m1/s1 |
| InChI Key | IJEHYEVNWOYGMS-WGUBEYSISA-N |
Properties
| Appearance | Yellow Acicular Crystalline |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 134-136°C |
Reference Reading
1. Complete biosynthetic pathways of ascofuranone and ascochlorin in Acremonium egyptiacum
Yasuko Araki, Takayoshi Awakawa, Motomichi Matsuzaki, Rihe Cho, Yudai Matsuda, Shotaro Hoshino, Yasutomo Shinohara, Masaichi Yamamoto, Yasutoshi Kido, Daniel Ken Inaoka, Kisaburo Nagamune, Kotaro Ito, Ikuro Abe, Kiyoshi Kita Proc Natl Acad Sci U S A. 2019 Apr 23;116(17):8269-8274. doi: 10.1073/pnas.1819254116. Epub 2019 Apr 5.
Ascofuranone (AF) and ascochlorin (AC) are meroterpenoids produced by various filamentous fungi, including Acremonium egyptiacum (synonym: Acremonium sclerotigenum), and exhibit diverse physiological activities. In particular, AF is a promising drug candidate against African trypanosomiasis and a potential anticancer lead compound. These compounds are supposedly biosynthesized through farnesylation of orsellinic acid, but the details have not been established. In this study, we present all of the reactions and responsible genes for AF and AC biosyntheses in A. egyptiacum, identified by heterologous expression, in vitro reconstruction, and gene deletion experiments with the aid of a genome-wide differential expression analysis. Both pathways share the common precursor, ilicicolin A epoxide, which is processed by the membrane-bound terpene cyclase (TPC) AscF in AC biosynthesis. AF biosynthesis branches from the precursor by hydroxylation at C-16 by the P450 monooxygenase AscH, followed by cyclization by a membrane-bound TPC AscI. All genes required for AC biosynthesis (ascABCDEFG) and a transcriptional factor (ascR) form a functional gene cluster, whereas those involved in the late steps of AF biosynthesis (ascHIJ) are present in another distantly located cluster. AF is therefore a rare example of fungal secondary metabolites requiring multilocus biosynthetic clusters, which are likely to be controlled by the single regulator, AscR. Finally, we achieved the selective production of AF in A. egyptiacum by genetically blocking the AC biosynthetic pathway; further manipulation of the strain will lead to the cost-effective mass production required for the clinical use of AF.
2. Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347
Bin Wu, Vanessa Oesker, Jutta Wiese, Susann Malien, Rolf Schmaljohann, Johannes F Imhoff Mar Drugs. 2014 Apr 1;12(4):1924-38. doi: 10.3390/md12041924.
A novel spirocyclic drimane coupled by two drimane fragment building blocks 2 and a new drimane 1 were identified in mycelia and culture broth of Stachybotrys sp. MF347. Their structures were established by spectroscopic means. This is the first example of spirocyclic drimane coupled by a spirodihydrobenzofuranlactam unit and a spirodihydroisobenzofuran unit; and the connecting position being N-C instead of an N and N connecting unit. Strain MF347 produced also the known spirocyclic drimanes stachybocin A (12) and stachybocin B (11) featured by two sesquiterpene-spirobenzofuran structural units connected by a lysine residue; the known spirocyclic drimanes chartarlactam O (5); chartarlactam K (6); F1839A (7); stachybotrylactam (8); stachybotramide (9); and 2α-acetoxystachybotrylactam acetate (10); as well as ilicicolin B (13), a known sesquiterpene. The relative configuration of two known spirobenzofuranlactams (3 and 4) was determined. All compounds were subjected to biological activity tests. The spirocyclic drimane 2, 11, and 12, as well as the sesquiterpene 13, exhibited antibacterial activity against the clinically relevant methicillin-resistant Staphylococcus aureus (MRSA).
3. Discovery of a new structural class of competitive hDHODH inhibitors with in vitro and in vivo anti-inflammatory, immunosuppressive effects
Wenbin Shen, Xiao Ren, Jingtong Zhu, Yan Xu, Jie Lin, Yeying Li, Feng Zhao, Haizhou Zheng, Ruolan Li, Xiaolan Cui, Xuexia Zhang, Xinhua Lu, Zhihui Zheng Eur J Pharmacol. 2016 Nov 15;791:205-212. doi: 10.1016/j.ejphar.2016.09.004. Epub 2016 Sep 3.
Human dihydroorotate dehydrogenase (hDHODH) is an inner mitochondrial membrane enzyme that involves in the fourth step of the biosynthesis of pyrimidine base. Inhibitors of hDHODH have been proven efficacy for the treatments of inflammation, rheumatoid arthritis, multiple sclerosis and cancer. In the present study, ascochlorin (ASC) and its derivatives, natural compounds from fungal metabolites, were discovered as hDHODH inhibitors by high-throughput screening. Enzyme kinetics studies showed that ASC competitively binds to hDHODH at the site of coenzyme Q substrate. In ex vivo study, ASC significantly inhibited the ConA-stimulated T lymphocytes proliferation and interleukin-2, interferon-γ production. Furthermore, ASC showed significant in vivo anti-inflammatory and immunosuppressive effects on the mice ears swelling, allogenic skin grafts and rat collagen-induced arthritis animal disease models. ASC significantly reduced ears edema level of mice, increased the survival time of allogenic skin implanted on the mice and attenuated arthritis severity of rat model. In conclusion, ASC was identified as a new structural class of hDHODH inhibitors with efficient anti-inflammatory, immunosuppressive activity, and may be a promising candidate for the development of new therapy in the treatment of autoimmune diseases.
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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 ╳
