Benzomalvin A
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| Category | Others |
| Catalog number | BBF-00629 |
| CAS | 157047-96-6 |
| Molecular Weight | 381.43 |
| Molecular Formula | C24H19N3O2 |
| Purity | ≥95% |
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Description
It is produced by the strain of Penicillum sp. Benzomalvin A was isolated as an active inhibitor of substance P binding to mammalian neurokinin NK1 receptors. Benzomalvin A is a fungal metabolite produced by Penicillium. It inhibits yeast α-glucosidase in vitro with IC50 of 383.2 μM. Benzomalvin A also acts as an antagonist of neurokinin-1 (NK1) receptors, inhibiting binding of substance P to guinea pig, rat, and human NK1 (Kis = 12, 42, and 43 μM, respectively).
Specification
| Synonyms | (-)-Benzomalvin A; Enzomalvin-A |
| IUPAC Name | (7S)-7-benzyl-6-methyl-7H-quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione |
| Canonical SMILES | CN1C(C2=NC3=CC=CC=C3C(=O)N2C4=CC=CC=C4C1=O)CC5=CC=CC=C5 |
| InChI | InChI=1S/C24H19N3O2/c1-26-21(15-16-9-3-2-4-10-16)22-25-19-13-7-5-11-17(19)24(29)27(22)20-14-8-6-12-18(20)23(26)28/h2-14,21H,15H2,1H3/t21-/m0/s1 |
| InChI Key | YYWUABJYAOCACI-NRFANRHFSA-N |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 599.3±60.0 °C |
| Melting Point | 105-115 °C |
| Density | 1.28±0.1 g/cm3 |
| Solubility | Soluble in DMSO. |
Reference Reading
1. Benzomalvins, new substance P inhibitors from a Penicillium sp
D M Sedlock, R Cooper, C J Barrow, H H Sun, A M Gillum J Antibiot (Tokyo) . 1994 May;47(5):515-22. doi: 10.7164/antibiotics.47.515.
In the course of screening microbial broths for neurokinin receptor antagonists, a series of new benzodiazepines, benzomalvins A (1), B (2) and C (3), has been isolated from the culture broth of a fungus identified as a Penicillium sp. Benzomalvin A (1) showed inhibitory activity against substance P with Ki values of 12, 42 and 43 microM at the guinea pig, rat and human neurokinin NK1 receptors, respectively. Benzomalvins B (2) and C (3) were only weakly active. The structures of these compounds were determined by spectroscopic methods including MS measurements and NMR analysis.
2. Interrogation of Benzomalvin Biosynthesis Using Fungal Artificial Chromosomes with Metabolomic Scoring (FAC-MS): Discovery of a Benzodiazepine Synthase Activity
KaHoua Yang, Kenneth D Clevenger, Cynthia Chen, Edward Wu, Md Nurul Islam, Nancy P Keller, Jin Woo Bok, Peng Gao, Michael Swyers, Chengcang C Wu, Neil L Kelleher, Rosa Ye, Galen P Miley, Matthew T Robey, Paul M Thomas Biochemistry . 2018 Jun 12;57(23):3237-3243. doi: 10.1021/acs.biochem.8b00076.
The benzodiazepine benzomalvin A/D is a fungally derived specialized metabolite and inhibitor of the substance P receptor NK1, biosynthesized by a three-gene nonribosomal peptide synthetase cluster. Here, we utilize fungal artificial chromosomes with metabolomic scoring (FAC-MS) to perform molecular genetic pathway dissection and targeted metabolomics analysis to assign the in vivo role of each domain in the benzomalvin biosynthetic pathway. The use of FAC-MS identified the terminal cyclizing condensation domain as BenY-CTand the internal C-domains as BenZ-C1and BenZ-C2. Unexpectedly, we also uncovered evidence suggesting BenY-CTor a yet to be identified protein mediates benzodiazepine formation, representing the first reported benzodiazepine synthase enzymatic activity. This work informs understanding of what defines a fungal CTdomain and shows how the FAC-MS platform can be used as a tool for in vivo analyses of specialized metabolite biosynthesis and for the discovery and dissection of new enzyme activities.
3. Two new Penicillium species Penicillium buchwaldii and Penicillium spathulatum, producing the anticancer compound asperphenamate
Jos Houbraken, Suuske Popma, Robert A Samson, Jens C Frisvad FEMS Microbiol Lett . 2013 Feb;339(2):77-92. doi: 10.1111/1574-6968.12054.
Penicillium buchwaldii sp. nov. (type strain CBS 117181(T) = IBT 6005(T) = IMI 30428(T) ) and Penicillium spathulatum sp. nov. (CBS 117192(T) = IBT 22220(T) ) are described as new species based on a polyphasic taxonomic approach. Isolates of P. buchwaldii typically have terverticillate conidiophores with echinulate thick-walled conidia and produce the extrolites asperphenamate, citreoisocoumarin, communesin A and B, asperentin and 5'-hydroxy-asperentin. Penicillium spathulatum is unique in having restricted colonies on Czapek yeast agar (CYA) with an olive grey reverse, good growth on CYA supplemented with 5% NaCl, terverticillate bi- and ter-ramulate conidiophores and consistently produces the extrolites benzomalvin A and D and asperphenamate. The two new species belong to Penicillium section Brevicompacta and are phylogenetically closely related to Penicillium tularense. With exception of Penicillium fennelliae, asperphenamate is also produced by all other species in section Brevicompacta (P. tularense, Penicillium brevicompactum, Penicillium bialowiezense, Penicillium olsonii, Penicillium astrolabium and Penicillium neocrassum). Both new species have a worldwide distribution. The new species were mainly isolated from indoor environments and food and feedstuffs. The fact that asperphenamate has been found in many widely different plants may indicate that endophytic fungi rather than the plants are the actual producers.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
