Clavilactone C
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| Category | Antibiotics |
| Catalog number | BBF-00365 |
| CAS | |
| Molecular Weight | 304.29 |
| Molecular Formula | C16H16O6 |
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Description
Clavilactone C is produced by the strain of Clitocybe clavipes. It can inhibit the germination of seeds.
Specification
| IUPAC Name | (1S,4E,6S,13R,14S)-6,8,11-trihydroxy-5-methyl-15,17-dioxatetracyclo[11.2.2.01,14.07,12]heptadeca-4,7,9,11-tetraen-16-one |
| Canonical SMILES | CC1=CCCC23C(O2)C(C4=C(C=CC(=C4C1O)O)O)OC3=O |
| InChI | InChI=1S/C16H16O6/c1-7-3-2-6-16-14(22-16)13(21-15(16)20)11-9(18)5-4-8(17)10(11)12(7)19/h3-5,12-14,17-19H,2,6H2,1H3/b7-3+/t12-,13+,14-,16-/m0/s1 |
| InChI Key | UUTMDRVBLMQCDI-VAXWODBPSA-N |
Properties
| Appearance | Yellow Crystallineline |
| Melting Point | 178-182 °C |
Reference Reading
1. Total Synthesis and Structural Revision of Clavilactone D
Ken-Ichi Takao, Ryuichi Nemoto, Kento Mori, Ayumi Namba, Keisuke Yoshida, Akihiro Ogura Chemistry. 2017 Mar 17;23(16):3828-3831. doi: 10.1002/chem.201700483. Epub 2017 Feb 23.
A structural revision of clavilactone D, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a γ-butenolide. The syntheses confirmed that the correct structure of clavilactone D has an amino group at C-3 instead of a hydroxy group at C-2 in the originally proposed structure.
2. Highly convergent three component benzyne coupling: the total synthesis of ent-clavilactone B
Igor Larrosa, Marianne I Da Silva, Patricio M Gómez, Peter Hannen, Eunjung Ko, Steven R Lenger, Simon R Linke, Andrew J P White, Donna Wilton, Anthony G M Barrett J Am Chem Soc. 2006 Nov 1;128(43):14042-3. doi: 10.1021/ja0662671.
The first total synthesis of (+)-clavilactone B, a potent antifungal agent and novel tyrosine kinase inhibitor, is described. The absolute configuration of clavilactones has been unambiguously established by using Sharpless asymmetric epoxidation to generate the enantiomerically pure substrate. The strategy highlights the use of a powerful and convergent three-component benzyne coupling with a methylallyl Grignard and a chiral epoxy-aldehyde to generate two C-C bonds and install the carbon skeleton of clavilactone. Oxidative lactonization, ten-membered ring construction by ring closing metathesis, and oxidation gave clavilactone B.
3. Novel geranylhydroquinone derived meroterpenoids from the fungus Clitocybe clavipes and their cytotoxic activity
Yong Hou, Qinglong Li, Meiying Chen, Haifeng Wu, Junshan Yang, Zhaocui Sun, Xudong Xu, Guoxu Ma Fitoterapia. 2022 Sep;161:105251. doi: 10.1016/j.fitote.2022.105251. Epub 2022 Jul 6.
Three novel geranylhydroquinone derived meroterpenoids, named clavilactones J and K (1-2) and clavipol C (3), were isolated from the basidiomycete Clitocybe clavipes. Their structures were unambiguously identified by extensive spectroscopic data analysis, and the electronic circular dichroism (ECD) calculation, Gauge-Including Atomic Orbitals (GIAO) NMR calculations and Mo2(OAc)4-induced electronic circular dichroism experiments were used to establish their absolute configurations. Compound 1, with two epoxy groups located at the 10-membered carbocycle, is uncommon in the reported meroterpenoids from C. clavipes. All the obtained compounds (1-3) were tested for their cytotoxic activity against human tumor cell line HGC-27 by using the MTT assay. All the compounds exhibited moderate cytotoxic activities against HGC-27 cell with IC50 values ranging from 33.5 to 56.6 μM.
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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 ╳
