BE-54238A

BE-54238A

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Category Mycotoxins
Catalog number BBF-03243
CAS 205433-26-7
Molecular Weight 397.42
Molecular Formula C22H23NO6

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Description

BE-54238A is a cytotoxic agent produced by Streptomyces sp. A54238. It has anti-proliferative effects on tumor cells such as P388, DLD4, PC-13, MKN-45, colon 26, etc., with IC50 of (μg/mL) 9.1, 3.5, 11.3, 8.1, 8.6.

Specification

Synonyms BE-54238 A; (-)-Be-54238a; 2-(5-Hydroxy-11-(1-hydroxyethyl)-4-methyl-6-oxo-1,4,6,9,10,11-hexahydro-2H-benzo(cd)pyrano(3,4-g)pyrrolo(1,2-a)indol-2-yl)acetic acid
IUPAC Name 2-[10-hydroxy-3-(1-hydroxyethyl)-14-methyl-12-oxo-15-oxa-2-azapentacyclo[9.7.1.02,6.07,19.013,18]nonadeca-1(19),6,8,10,13(18)-pentaen-16-yl]acetic acid
Canonical SMILES CC1C2=C(CC(O1)CC(=O)O)C3=C4C(=C5N3C(CC5)C(C)O)C=CC(=C4C2=O)O
InChI InChI=1S/C22H23NO6/c1-9(24)14-4-5-15-12-3-6-16(25)20-19(12)21(23(14)15)13-7-11(8-17(26)27)29-10(2)18(13)22(20)28/h3,6,9-11,14,24-25H,4-5,7-8H2,1-2H3,(H,26,27)
InChI Key MEQMTDCBXJRPBS-UHFFFAOYSA-N

Properties

Appearance Orange Powder
Antibiotic Activity Spectrum neoplastics (Tumor)
Boiling Point 679.5±55.0°C at 760 mmHg
Density 1.6±0.1 g/cm3

Reference Reading

1. Glenthenamines A-F: Enamine Pyranonaphthoquinones from the Australian Pasture Plant Derived Streptomyces sp. CMB-PB042
Taizong Wu, Angela A Salim, Hui Cui, Zeinab G Khalil, Paul V Bernhardt, Robert J Capon J Nat Prod. 2022 Feb 25;85(2):337-344. doi: 10.1021/acs.jnatprod.1c00821. Epub 2022 Jan 24.
Chemical investigations into solid phase cultivations of an Australian sheep station pasture plant derived Streptomyces sp. CMB-PB042 yielded the rare enamine naphthopyranoquinones BE-54238A (1) and BE-54238B (2), together with four new analogues, glenthenamines B-D (4-6) and F (8), and two handling artifacts, glenthenamines A (3) and E (7). Single-crystal X-ray analyses of 1 and 2 resolved configurational ambiguities in the scientific literature, while detailed spectroscopic analysis and biosynthetic considerations assigned structures inclusive of absolute configuration to 3-8. We propose a plausible sequence of biosynthetic transformations linking structural and configurational features of 1-8 and apply a novel Schiff base "fishing" approach to detect a key deoxyaminosugar precursor. These enamine naphthopyranoquinones disclose a new P-gp inhibitory pharmacophore capable of reversing doxorubicin resistance in P-gp overexpressing colon carcinoma cells.
2. New cytotoxic agents, BE-54238A and B, produced by a streptomycete
M Tsukamoto, S Nakajima, K Murooka, M Hirayama, K Hirano, S Yoshida, K Kojiri, H Suda J Antibiot (Tokyo). 2000 Jan;53(1):26-32. doi: 10.7164/antibiotics.53.26.
New cytotoxic substances, designated BE-54238A and B, were isolated from the culture broth of Streptomyces sp. A54238. The active principles were extracted from the mycelium by methanol and purified by Diaion HP-20 and Sephadex LH-20 column chromatographies. BE-54238A and B exhibited cytotoxic activity against murine and human tumor cell lines.
3. Discovery of C-Glycosylpyranonaphthoquinones in Streptomyces sp. MBT76 by a Combined NMR-Based Metabolomics and Bioinformatics Workflow
Changsheng Wu, Chao Du, Koji Ichinose, Young Hae Choi, Gilles P van Wezel J Nat Prod. 2017 Feb 24;80(2):269-277. doi: 10.1021/acs.jnatprod.6b00478. Epub 2017 Jan 27.
Mining of microbial genomes has revealed that actinomycetes harbor far more biosynthetic potential for bioactive natural products than anticipated. Activation of (cryptic) biosynthetic gene clusters and identification of the corresponding metabolites has become a focal point for drug discovery. Here, we applied NMR-based metabolomics combined with bioinformatics to identify novel C-glycosylpyranonaphthoquinones in Streptomyces sp. MBT76 and to elucidate the biosynthetic pathway. Following activation of the cryptic qin gene cluster for a type II polyketide synthase (PKS) by constitutive expression of its pathway-specific activator, bioinformatics coupled to NMR profiling facilitated the chromatographic isolation and structural elucidation of qinimycins A-C (1-3). The intriguing structural features of the qinimycins, including 8-C-glycosylation, 5,14-epoxidation, and 13-hydroxylation, distinguished these molecules from the model pyranonaphthoquinones actinorhodin, medermycin, and granaticin. Another novelty lies in the unusual fusion of a deoxyaminosugar to the pyranonaphthoquinone backbone during biosynthesis of the antibiotics BE-54238 A and B (4, 5). Qinimycins showed weak antimicrobial activity against Gram-positive bacteria. Our work shows the utility of combining bioinformatics, targeted activation of cryptic gene clusters, and NMR-based metabolic profiling as an effective pipeline for the discovery of microbial natural products with distinctive skeletons.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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