Duclauxin
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| Category | Antibiotics |
| Catalog number | BBF-01178 |
| CAS | 1732-37-2 |
| Molecular Weight | 546.48 |
| Molecular Formula | C29H22O11 |
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Description
It is produced by the strain of Penicillum stipitatum. It has inhibitory effect on Ehrlician ascites carcinoma, lymphoma L-5178 and sarcoma 37.
Specification
| Synonyms | 15H-8,15a-Methano-3H,13H-benzo[de]cycloocta[1,2-g_3,4,5-d'e']bis[2]benzopyran-3,9,13,16-tetrone,17-(acetyloxy)-6b,7,8,15b-tetrahydro-4,12-dihydroxy-6b-methoxy-6,10-dimethyl- |
| IUPAC Name | [(1S,2R,13S,14R,24S)-9,19-dihydroxy-13-methoxy-11,17-dimethyl-3,7,15,21-tetraoxo-6,22-dioxaheptacyclo[12.9.1.11,16.14,8.02,13.012,26.020,25]hexacosa-4,8,10,12(26),16(25),17,19-heptaen-24-yl] acetate |
| Canonical SMILES | CC1=CC(=C2C3=C1C(=O)C4C(C3(COC2=O)C5C4(C6=C7C(=COC(=O)C7=C(C=C6C)O)C5=O)OC)OC(=O)C)O |
| InChI | InChI=1S/C29H22O11/c1-9-5-14(32)18-20-15(9)23(34)21-25(40-11(3)30)28(20,8-39-27(18)36)24-22(33)12-7-38-26(35)17-13(31)6-10(2)19(16(12)17)29(21,24)37-4/h5-7,21,24-25,31-32H,8H2,1-4H3/t21-,24-,25+,28-,29-/m1/s1 |
| InChI Key | WBQDAYWQELBEPU-UWFIUXRYSA-N |
Properties
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 891.0 °C at 760 mmHg |
| Melting Point | 137-236 °C |
| Density | 1.66 g/cm3 |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Biosynthesis of Heptacyclic Duclauxins Requires Extensive Redox Modifications of the Phenalenone Aromatic Polyketide
Shu-Shan Gao, Tao Zhang, Marc Garcia-Borràs, Yiu-Sun Hung, John M Billingsley, K N Houk, Youcai Hu, Yi Tang J Am Chem Soc. 2018 Jun 6;140(22):6991-6997. doi: 10.1021/jacs.8b03705. Epub 2018 May 24.
Duclauxins are dimeric and heptacyclic fungal polyketides with notable bioactivities. We characterized the cascade of redox transformations in the biosynthetic pathway of duclauxin from Talaromyces stipitatus. The redox reaction sequence is initiated by a cupin family dioxygenase DuxM that performs an oxidative cleavage of the peri-fused tricyclic phenalenone and affords a transient hemiketal-oxaphenalenone intermediate. Additional redox enzymes then morph the oxaphenoalenone into either an anhydride or a dihydrocoumarin-containing monomeric building block that is found in dimeric duxlauxins. Oxidative coupling between the monomers to form the initial C-C bond was shown to be catalyzed by a P450 monooxygenase, although the enzyme responsible for the second C-C bond formation was not found in the pathway. Collectively, the number and variety of redox enzymes used in the duclauxin pathway showcase Nature's strategy to generate structural complexity during natural product biosynthesis.
2. Duclauxin Derivatives From Fungi and Their Biological Activities
Hamza Shahid, Teng Cai, Yuyang Wang, Caiqing Zheng, Yuting Yang, Ziling Mao, Ping Ding, Tijiang Shan Front Microbiol. 2021 Dec 22;12:766440. doi: 10.3389/fmicb.2021.766440. eCollection 2021.
Duclauxin is a heptacyclic oligophenalenone dimer consisting of an isocoumarin and a dihydroisocoumarin unit. These two tricyclic moieties are joined by a cyclopentane ring to form a unique hinge or castanets-like structure. Duclauxin is effective against numerous tumor cell lines because it prevents adenosine triphosphate (ATP) synthesis by inhibiting mitochondrial respiration. There are about 36 reported natural duclauxin analogs mainly produced by 9 Penicillium and Talaromyces species (T. duclauxii, T. aculeatus, T. stipitatus, T. bacillisporus, T. verruculosus, T. macrosporus, P. herquei, P. manginii, and Talaromyces sp.). These metabolites exhibit remarkable biological activities, including antitumor, enzyme inhibition, and antimicrobial, showing tremendous potential in agricultural and medical applications. This review highlights the chemical structures and biological activities of fungal duclauxins, together with biosynthesis, absolute configuration, and mode of action for important duclauxins. Furthermore, phylogenetic analysis and correct names of Penicillium and Talaromyces species producing duclauxins are presented in this review.
3. Talauxins: Hybrid Phenalenone Dimers from Talaromyces stipitatus
Nirmal K Chaudhary, Andrew Crombie, Daniel Vuong, Ernest Lacey, Andrew M Piggott, Peter Karuso J Nat Prod. 2020 Apr 24;83(4):1051-1060. doi: 10.1021/acs.jnatprod.9b01066. Epub 2020 Mar 2.
Cultivation and extraction of the fungus Talaromyces stipitatus led to the isolation of five new oxyphenalenone-amino acid hybrids, which were named talauxins E, Q, V, L, and I based on the corresponding one-letter amino acid codes, along with their putative biosynthetic precursor, duclauxin. The rapid reaction of duclauxin with amino acids to produce talauxins was demonstrated in vitro and exploited to generate a small library of natural and unnatural talauxins. Talauxin V was shown to undergo spontaneous elimination of methyl acetate to yield the corresponding neoclauxin scaffold. This process was modeled using density functional theory calculations, revealing a dramatic change in conformation resulting from the syn elimination of methyl acetate.
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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 ╳
