Cladospolide B
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00353 |
| CAS | 96443-55-9 |
| Molecular Weight | 228.28 |
| Molecular Formula | C12H20O4 |
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Description
It is produced by the strain of Cladosporium sp. FT-0012. Cladospolide B has little antibacterial activity.
Specification
| Synonyms | 4,5-di-epi-Cladospolide C |
| IUPAC Name | (3Z,5S,6S,12R)-5,6-dihydroxy-12-methyl-1-oxacyclododec-3-en-2-one |
| Canonical SMILES | CC1CCCCCC(C(C=CC(=O)O1)O)O |
| InChI | InChI=1S/C12H20O4/c1-9-5-3-2-4-6-10(13)11(14)7-8-12(15)16-9/h7-11,13-14H,2-6H2,1H3/b8-7-/t9-,10+,11+/m1/s1 |
| InChI Key | PLHJPQNLCWFPFY-DCOWIPOFSA-N |
Properties
| Appearance | White Powder |
Reference Reading
1. Lipid-lowering polyketides from a soft coral-derived fungus Cladosporium sp. TZP29
Meilin Zhu, Huquan Gao, Chongming Wu, Tianjiao Zhu, Qian Che, Qianqun Gu, Peng Guo, Dehai Li Bioorg Med Chem Lett. 2015 Sep 1;25(17):3606-9. doi: 10.1016/j.bmcl.2015.06.072. Epub 2015 Jul 3.
Two new C12 polyketides, cladospolides E and F (1 and 2), together with four known derivatives seco-patulolides A and C (3 and 4), 11-hydroxy-γ-dodecalactone (5) and iso-cladospolide B (6), were isolated from a soft coral-derived fungus Cladosporium sp. TZP-29. Their structures, including the absolute configurations, were elucidated by spectroscopic analysis, modified Mosher's method, and the analysis of their biogenesis. All compounds were non-cytotoxic while compounds 1 and 3-5 showed potent lipid-lowering activity in HepG2 hepatocytes.
2. A flexible and unified strategy for syntheses of cladospolides A, B, C, and iso-cladospolide B
Debjani Si, Narayana M Sekar, Krishna P Kaliappan Org Biomol Chem. 2011 Oct 21;9(20):6988-97. doi: 10.1039/c1ob05787a. Epub 2011 Aug 18.
A simple, efficient and flexible strategy for the syntheses of cladospolides A-C and iso-cladospolide B is reported here. This strategy involves Julia-Kocienski olefination and Yamaguchi macrolactonization as key steps, starting from either d-ribose or suitable tartaric acid esters. Although our initial efforts towards cladospolide A involving a ring closing metathetic approach were not successful, changing the mode of ring closure and the use of Julia-Kocienski olefination for the construction of the key intermediate solved this issue and paved the way for the completion of total syntheses of this class of natural products.
3. Metabolites From the Mangrove-Derived Fungus Cladosporium sp. HNWSW-1
Xi Cao, Lei Guo, Caihong Cai, Fandong Kong, Jingzhe Yuan, Cuijuan Gai, Haofu Dai, Pei Wang, Wenli Mei Front Chem. 2021 Dec 16;9:773703. doi: 10.3389/fchem.2021.773703. eCollection 2021.
Two new benzoic acids, cladoslide A (1) and cladoslide B (2); one new β-carboline derivative, cladospomine (3); and one new pyridin-2(1H)-one, cladoslide C (4), were isolated from the fermentation cultures of the mangrove-derived fungus Cladosporium sp. HNWSW-1, along with the previously reported N-acetyl-β-oxotryptamine (5), (4S,5S,11R)-iso-cladospolide B (6), (4S,5S,11S)-iso-cladospolide B (7), and (4R,5S,11R)-iso-cladospolide B (8). Their structures were elucidated by spectroscopic analysis, Rh2(OCOCF3)4-induced ECD experiments, and Marfey's method. Compound 1 showed cytotoxicity against the K562 cell line with IC50 values of 13.10 ± 0.08 μM. Moreover, compounds 1 and 5 exhibited inhibitory activity against α-glycosidase with IC50 values of 0.32 ± 0.01 mM and 0.17 ± 0.01 mM, respectively.
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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 ╳
