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Topopyrone D

Name: Topopyrone D
Brand: BOC Sciences
Rating: 5 (1 reviews)

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Category	Enzyme inhibitors
Catalog number	BBF-02703
CAS
Molecular Weight	338.27
Molecular Formula	C18H10O7

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

It is produced by the strain of Phoma sp. BAUA 2861 and Penicillum sp. BAUA 4206. Topopyrone A selectively inhibits topoisomerase I with the IC50 of 19.63 ng/mL.

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IUPAC Name	5,7,9-trihydroxy-2-methylnaphtho[2,3-g]chromene-4,6,11-trione
Canonical SMILES	CC1=CC(=O)C2=C(O1)C=C3C(=C2O)C(=O)C4=C(C3=O)C=C(C=C4O)O
InChI	InChI=1S/C18H10O7/c1-6-2-10(20)15-12(25-6)5-9-14(18(15)24)17(23)13-8(16(9)22)3-7(19)4-11(13)21/h2-5,19,21,24H,1H3
InChI Key	WKOUXLOBNJWENY-UHFFFAOYSA-N

Appearance	Orange Powder
Melting Point	>280°C

1. Identification and Heterologous Expression of the Topopyrone Nonaketide Synthase Gene from Phoma sp

Nobuyuki Kashiwa, Yutaka Ebizuka, Isao Fujii Chem Pharm Bull (Tokyo). 2016;64(7):947-51. doi: 10.1248/cpb.c16-00172.

Non-reducing iterative type I polyketide synthase genes, pnk1 and pnk2, were cloned from the fungus Phoma sp. BAUA2861, which produces the topoisomerase I inhibitors, topopyrones A to D. Heterologous expression of these polyketide synthase genes under the α-amylase promoter in Aspergillus oryzae was carried out to identify their functions. The pnk2 transformant produced topopyrones C, D, and haematommone. Therefore, the pnk2 gene was found to encode for the topopyrone nonaketide synthase.

2. Total synthesis of topopyrones B and D

Jason Samuel Tan, Marco A Ciufolini Org Lett. 2006 Oct 12;8(21):4771-4. doi: 10.1021/ol0617291.

[reaction: see text] We describe a straightforward synthesis of topopyrones B and D, which are potent and selective inhibitors of topoisomerase I. The chemistry should be suitable for additional structure-activity relationship (SAR) work.

3. Novel human topoisomerase I inhibitors, topopyrones A, B, C and D. II. Structure elucidation

D Ishiyama, Y Kanai, H Senda, W Iwatani, W Iwatani, H Konno, S Kanazawa J Antibiot (Tokyo). 2000 Sep;53(9):873-8. doi: 10.7164/antibiotics.53.873.

The structures of novel topoisomerase I inhibitors, topopyrones A, B, C and D were elucidated by spectral analysis of the chemical derivatives. These compounds are an anthraquinone type containing a fused 1,4-pyrone moiety. Topopyrones A and B contain a chlorine atom, however C and D do not. It was suggested that topopyrones B and D are converted from topopyrones A and C, respectively by Wessely-Moser type rearrangement.

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