Lachnone A
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| Category | Bioactive by-products |
| Catalog number | BBF-04266 |
| CAS | 903892-99-9 |
| Molecular Weight | 206.19 |
| Molecular Formula | C11H10O4 |
| Purity | >95% by HPLC |
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Description
It is a chromone isolated from the filamentous fungus, lachnum sp. It possesses weak activity against bacteria but has not been extensively investigated.
Specification
| Synonyms | Lanchnone A; 3,5-Dihydroxy-2,7-dimethyl-4H-1-benzopyran-4-one |
| Storage | Store at -20°C |
| IUPAC Name | 3,5-dihydroxy-2,7-dimethylchromen-4-one |
| Canonical SMILES | CC1=CC(=C2C(=C1)OC(=C(C2=O)O)C)O |
| InChI | InChI=1S/C11H10O4/c1-5-3-7(12)9-8(4-5)15-6(2)10(13)11(9)14/h3-4,12-13H,1-2H3 |
| InChI Key | BUDFSMORTDVVOU-UHFFFAOYSA-N |
| Source | Unidentified fungus |
Properties
| Appearance | Off-white to Grey Solid |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 386.2±42.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. A Hydrolase-Catalyzed Cyclization Forms the Fused Bicyclic β-Lactone in Vibralactone
Tao Feng, Yue Zhang, Ji-Kai Liu, Ying Zeng, Ke-Na Feng, Sheng-Xiong Huang, Yan-Long Yang, Yu-Xing Xu Angew Chem Int Ed Engl . 2020 Apr 27;59(18):7209-7213. doi: 10.1002/anie.202000710.
Vibralactone is isolated from the basidiomycete fungus Boreostereum vibrans as one of the strongest lipase inhibitors. Its unusual β-lactone-fused bicycle is derived from an aryl ring moiety by an oxidative ring-expansion prior to an intramolecular cyclization. Herein, we report the discovery of the cyclase VibC which belongs to the α/β-hydrolase superfamily and is involved in the vibralactone biosynthesis. Biochemical and crystal studies suggest that VibC may catalyze an aldol or an electrocyclic reaction initiated by the Ser-His-Asp catalytic triad. For the aldol and pericyclic chemistry in living cells, VibC is a unique hydrolase performing the carbocycle formation of an oxepinone to a fused bicyclic β-lactone. This presents a naturally occurring, new enzymatic reaction in both aldol and hydrolase (bio)chemistry that will guide future exploitation of these enzymes in synthetic biology for chemical-diversity expansion of natural products.
2. Lasiodiplactone A, a novel lactone from the mangrove endophytic fungus Lasiodiplodia theobromae ZJ-HQ1
Dongni Chen, Zhigang She, Senhua Chen, Zhaoming Liu, Hongju Liu, Yongjun Lu, Yuhua Long Org Biomol Chem . 2017 Aug 2;15(30):6338-6341. doi: 10.1039/c7ob01657c.
Lasiodiplactone A (1), an unprecedented lactone, was obtained from the mangrove endophytic fungus Lasiodiplodia theobromae ZJ-HQ1. The structure of 1 was established by analysis of NMR spectroscopic data and electronic circular dichroism (ECD) spectra. Lasiodiplactone A (1) was the first example of lactone that possesses a unique tetracyclic system (12/6/6/5) of RAL12(12-membered β-resorcylic acid lactone) with a pyran ring and a furan ring. A possible biogenetic pathway for 1 was proposed. Compound 1 showed anti-inflammatory activity by inhibiting nitric oxide (NO) production in lipopolysaccharide activated in RAW264.7 cells with IC50value of 23.5 μM and exhibited potential α-glucosidase inhibitory activity with IC50values of 29.4 μM.
3. Cochliomycin G, a 14-membered resorcylic acid lactone from a marine-derived fungus Cochliobolus lunatus
Chang-Yun Wang, Xiao-Jia Xue, Na-Na Wu, Wei-Feng Xu, Yue-Xuan Qi, Chang-Lun Shao Nat Prod Res . 2021 Feb;35(3):490-493. doi: 10.1080/14786419.2019.1633646.
Cochliomycin G (1), a new 14-membered resorcylic acid lactone, together with six known analogues (2-7), was isolated from the culture broth of a marine-derived fungusCochliobolus lunatus. The planar structure of1was established by extensive NMR spectroscopy, and the absolute configuration was elucidated by the combination of empirical rules, CD data, and13C chemical shift calculations. Compound1exhibited potent antifouling activity againstChlorella vulgaris,Chaetoceros socialis, andNavicula exigua, with EC50values of 1.09, 0.92, and 0.61μg/mL, 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 ╳
