Byssochlamic acid
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| Category | Mycotoxins |
| Catalog number | BBF-00194 |
| CAS | 743-51-1 |
| Molecular Weight | 332.35 |
| Molecular Formula | C18H20O6 |
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Description
Byssochlamic acid is a mycotoxin produced by Byssochlamys fulva (Paecilomyces variotii) and Bys. nivea.
Specification
| IUPAC Name | (2S,10R)-10-ethyl-2-propyl-6,14-dioxatricyclo[10.3.0.04,8]pentadeca-1(12),4(8)-diene-5,7,13,15-tetrone |
| Canonical SMILES | CCCC1CC2=C(CC(CC3=C1C(=O)OC3=O)CC)C(=O)OC2=O |
| InChI | InChI=1S/C18H20O6/c1-3-5-10-8-12-11(15(19)23-16(12)20)6-9(4-2)7-13-14(10)18(22)24-17(13)21/h9-10H,3-8H2,1-2H3/t9-,10+/m1/s1 |
| InChI Key | NRDWUPPIGBHWAS-ZJUUUORDSA-N |
Properties
| Melting Point | 163.5°C |
Reference Reading
1. Novel nonadride, heptadride and maleic acid metabolites from the byssochlamic acid producer Byssochlamys fulva IMI 40021 - an insight into the biosynthesis of maleidrides
Agnieszka J Szwalbe, Katherine Williams, Daniel E O'Flynn, Andrew M Bailey, Nicholas P Mulholland, Jason L Vincent, Christine L Willis, Russell J Cox, Thomas J Simpson Chem Commun (Camb). 2015 Dec 14;51(96):17088-91. doi: 10.1039/c5cc06988b.
The filamentous fungus Byssochlamys fulva strain IMI 40021 produces (+)-byssochlamic acid 1, its novel dihydroanalogue 2 and four related secondary metabolites. Agnestadrides A, 17 and B, 18 constitute a novel class of seven-membered ring, maleic anhydride-containing (hence termed heptadride) natural products. The putative maleic anhydride precursor 5 for both nonadride and heptadride biosynthesis was isolated as a fermentation product for the first time and its structure confirmed by synthesis. Acid 5 undergoes facile decarboxylation to anhydride 6. The generic term maleidrides is proposed to encompass biosynthetically-related compounds containing maleic anhydride moieties fused to an alicyclic ring, varying in size and substituents.
2. In vitro studies of maleidride-forming enzymes
Sen Yin, Steffen Friedrich, Vjaceslavs Hrupins, Russell J Cox RSC Adv. 2021 Apr 21;11(25):14922-14931. doi: 10.1039/d1ra02118d.
In vitro assays of enzymes involved in the biosynthesis of maleidrides from polyketides in fungi were performed. The results show that the enzymes are closely related to primary metabolism enzymes of the citric acid cycle in terms of stereochemical preferences, but with an expanded substrate selectivity. A key citrate synthase can react both saturated and unsaturated acyl CoA substrates to give solely anti substituted citrates. This undergoes anti-dehydration to afford an unsaturated precursor which is cyclised in vitro by ketosteroid-isomerase-like enzymes to give byssochlamic acid.
3. A new diimide derivative from the co-culture broth of two mangrove fungi (strain no. E33 and K38)
Chun-Yuan Li, Wei-Jia Ding, Chang-Lun Shao, Zhi-Gang She, Yong-Cheng Lin J Asian Nat Prod Res. 2010 Sep;12(9):809-13. doi: 10.1080/10286020.2010.497757.
A new diimide derivative, named (-)-byssochlamic acid bisdiimide (1), was isolated from the mixed broth of two mangrove fungi (strain no. K38 and E33) from the South China sea coast. The structure of 1 was determined by comprehensive spectroscopic methods, including 1D and 2D NMR (COSY, HMQC, and HMBC) and semi-synthesis. Primary bioassays showed that 1 had weak cytotoxic activity against Hep-2 and HepG2 cells.
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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 ╳
