Moniliphenone
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| Category | Others |
| Catalog number | BBF-04879 |
| CAS | 104022-80-2 |
| Molecular Weight | 302.28 |
| Molecular Formula | C16H14O6 |
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Description
Moniliphenone is a benzophenone biosynthetic intermediate produced by Monilinia fructicola and its anthraquinone precursors.
Specification
| IUPAC Name | methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxybenzoate |
| Canonical SMILES | CC1=CC(=C(C(=C1)O)C(=O)C2=C(C=CC=C2O)C(=O)OC)O |
| InChI | InChI=1S/C16H14O6/c1-8-6-11(18)14(12(19)7-8)15(20)13-9(16(21)22-2)4-3-5-10(13)17/h3-7,17-19H,1-2H3 |
| InChI Key | OLWGLSCBBRIVGJ-UHFFFAOYSA-N |
Properties
| Boiling Point | 451.1±40.0°C at 760 mmHg |
| Density | 1.392±0.06 g/cm3 (Predicted) |
Reference Reading
1. Isolation and characterization of two new chroman-4-ones from the endophytic fungus Penicillium chrysogenum obtained from Eucommia ulmoides Oliver
Sheng-Yue Liu, Li-Zhi Wang, Yue-Fei Wang, Lin Li, Guo-Ying Han, Bing-Yang Zhang, Ying Guo, Yong-Zhi He, Shi-Ming Fang, Han Zhang Nat Prod Res. 2022 Jul;36(13):3297-3302. doi: 10.1080/14786419.2020.1855161. Epub 2020 Dec 1.
Two new chroman-4-ones penicichromanone A (1) and penicichromanone B (2), together with three known compounds conioxepinol C (3), emodin (4) and moniliphenone (5), were obtained from the endophytic fungus Penicillium chrysogenum, which was isolated from the bark of Eucommia ulmoides Oliver. The structures of 1 and 2 were elucidated by detailed analysis of HRESIMS, 1D/2D NMR and ECD spectra. All the compounds were evaluated for their anti-inflammatory activities using HEK293 cells, and compounds 1, 3, 4 and 5 exhibited significant inhibitory effects on TNF-α-stimulated NF-κB activation.
2. Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi
Anna Dalinova, Leonid Chisty, Dmitry Kochura, Varvara Garnyuk, Maria Petrova, Darya Prokofieva, Anton Yurchenko, Vsevolod Dubovik, Alexander Ivanov, Sergey Smirnov, Andrey Zolotarev, Alexander Berestetskiy Biomolecules. 2020 Jan 4;10(1):81. doi: 10.3390/biom10010081.
The fungus, Alternaria sonchi is considered to be a potential agent for the biocontrol of perennial sowthistle (Sonchus arvensis). A new chlorinated xanthone, methyl 8-hydroxy-3-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (1) and a new benzophenone derivative, 5-chloromoniliphenone (2), were isolated together with eleven structurally related compounds (3-13) from the solid culture of the fungus, which is used for the production of bioherbicidal inoculum of A. sonchi. Their structures were determined by spectroscopic (mostly by NMR and MS) methods. Alternethanoxins A and B, which were reported in A. sonchi earlier, were re-identified as moniliphenone and pinselin, respectively. The isolated compounds were tested for phytotoxic, antimicrobial, insecticidal, cytotoxic and esterase-inhibition activities. They did not demonstrate high phytotoxicity (lesions up to 2.5 mm in diameter/length at a concentration of 2 mg/mL) when tested on leaf disks/segments of perennial sowthistle (Sonchus arvensis) and couch grass (Elytrigia repens). They did not possess acute toxicity to Paramecium caudatum, and showed moderate to low cytotoxicity (IC50 > 25 µg/mL) for U937 and K562 tumor cell lines. However, chloromonilicin and methyl 3,8-dihydroxy-6-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (4) were shown to have antimicrobial properties with MIC 0.5-5 µg/disc. Compound 4 and chloromonilinic acid B were found to have contact insecticidal activity to wheat aphid (Schizaphis graminum) at 1 mg/mL. Compounds 2 and methyl 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate displayed selective carboxylesterase inhibition activity at concentration of 100 µg/mL. Therefore, the waste solid substrate for production of A. sonchi spores can be re-utilized for the isolation of a number of valuable natural products.
3. Rabenchromenone and Rabenzophenone, Phytotoxic Tetrasubstituted Chromenone and Hexasubstituted Benzophenone Constituents Produced by the Oak-Decline-Associated Fungus Fimetariella rabenhorstii
Samaneh Bashiri, Jafar Abdollahzadeh, Roberta Di Lecce, Daniela Alioto, Marcin Górecki, Gennaro Pescitelli, Marco Masi, Antonio Evidente J Nat Prod. 2020 Feb 28;83(2):447-452. doi: 10.1021/acs.jnatprod.9b01017. Epub 2020 Jan 22.
A new phytotoxic tetrasubstituted chromen-4-one (1) and a new hexasubstituted benzophenone (2), named rabenchromenone and rabenzophenone, respectively, were isolated from the culture filtrates of Fimetariella rabenhorstii, an oak-decline-associated fungus in Iran. Rabenchromenone and rabenzophenone, isolated together with known moniliphenone (3) and coniochaetone A (4), were characterized as methyl 3-chloro-1,8-dihydroxy-6-methyl-9-oxo-1,9-dihydrocyclopenta[b]chromene-1-carboxylate and methyl 4-chloro-2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxybenzoate, respectively, by spectroscopic methods (primarily nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry). The R absolute configuration at C-1 of rabenchromenone was determined by quantum chemical calculations and electronic circular dichroism experiments. All metabolites (1-4) were tested by leaf puncture on tomato and oak plants. All compounds were active in this assay by causing in both plants a necrosis diameter in the range of 0.2-0.7 cm. Specifically, rabenzophenone (2) was found to be the most phytotoxic compound in both plants.
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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 ╳
