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目录号 : GC45811

A fungal metabolite

GKK1032B Chemical Structure

Cas No.:358375-11-8

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1mg
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产品描述

GKK1032B is a fungal metabolite originally isolated from Penicillium sp. GKK1032 that has antiproliferative and antibacterial activities.1,2 GKK1032B inhibits the growth of HeLa S3 cervical and MCF-7 breast cancer cells (IC50s = 17.7 and 14.71 μM, respectively) and Vero cells (IC50 = 29.55 μM). It also inhibits the growth of B. subtilis (MIC = 20.8 μg/ml) and M. tuberculosis (MIC = 48.35 μM).

|1. Li, X.-W., Ear, A., and Nay, B. Hirsutellones and beyond: Figuring out the biological and synthetic logics toward chemical complexity in fungal PKS-NRPS compounds. Nat. Prod. Rep. 30(6), 765-782 (2013).|2. Rukachaisirikul, V., Satpradit, S., Klaiklay, S., et al. Polyketide anthraquinone, diphenyl ether, and xanthone derivatives from the soil fungus Penicillium sp. PSU-RSPG99. Tetrahedron 70(34), 5148-5152 (2014).

Chemical Properties

Cas No. 358375-11-8 SDF
Canonical SMILES C[C@@H]1C[C@H](C)[C@]2([H])[C@@]([C@@](C(C)=C[C@@](C=C)(C)[C@]3([H])C4=O)([H])[C@]3([H])[C@]2([H])OC5=CC=C(C[C@@]6([H])[C@@]4([H])C(NC6=O)=O)C=C5)(C)C1
分子式 C32H39NO4 分子量 501.7
溶解度 Dichloromethane: soluble,DMSO: soluble,Ethanol: soluble 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 1.9932 mL 9.9661 mL 19.9322 mL
5 mM 0.3986 mL 1.9932 mL 3.9864 mL
10 mM 0.1993 mL 0.9966 mL 1.9932 mL
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Research Update

GKK1032B from endophytic Penicillium citrinum induces the apoptosis of human osteosarcoma MG63 cells through caspase pathway activation

Chin J Nat Med 2022 Jan;20(1):67-73.PMID:35101251DOI:10.1016/S1875-5364(21)60108-5.

Chemical investigation of the culture extract of an endophytic Penicillium citrinum from Dendrobium officinale, afforded nine citrinin derivatives (1-9) and one peptide-polyketide hybrid GKK1032B (10). The structures of these compounds were determined by spectroscopic methods. The absolute configurations of 1 and 2 were determined for the first time by calculation of electronic circular dichroism (ECD) data. Among them, GKK1032B (10) showed significant cytotoxicity against human osteosarcoma cell line MG63 with an IC50 value of 3.49 μmol·L-1, and a primary mechanistic study revealed that it induced the apoptosis of MG63 cellsvia caspase pathway activation.

GKK1032C, a new alkaloid compound from the endophytic fungus Penicillium sp. CPCC 400817 with activity against methicillin-resistant S. aureus

J Antibiot (Tokyo) 2019 Apr;72(4):237-240.PMID:30737454DOI:10.1038/s41429-019-0144-5.

Five alkaloid compounds (1-5), including one new compound, GKK1032C (1), and four known compounds, pyrrospirones E (2) and F (3), and GKK1032B (4) and A2 (5) were isolated from the culture of endophytic fungus Penicillium sp. CPCC 400817. The planar structures of all compounds were elucidated by NMR and MS spectra. The relative configuration of new compound GKK1032C (1) was deduced from the vicinal J-values and ROESY spectral data. Compound 1 exhibited potent antibacterial activity against methicillin-resistant Staphylococcus aureus with an MIC value of 1.6 μg ml-1.

Chromone Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA0220 and Their Antibacterial Activity

Mar Drugs 2018 Aug 20;16(8):289.PMID:30127313DOI:10.3390/md16080289.

A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin (1c), and four previously undescribed chromone derivatives, including pyanochromone (3b), spirofuranochromone (4), 7-hydroxy-6-methoxy-4-oxo-3-[(1E)-3-oxobut-1-en-1-yl]-4H-chromene-5-carboxylic acid (5), a pyranochromone dimer (6) were isolated, together with thirteen known compounds: β-sitostenone, ergosterol 5,8-endoperoxide, citromycin (1a), 12-methoxycitromycin (1b), myxotrichin D (1d), 12-methoxycitromycetin (1e), anhydrofulvic acid (2a), myxotrichin C (2b), penialidin D (2c), penialidin F (3a), SPF-3059-30 (7), GKK1032B (8) and secalonic acid A (9), from cultures of the marine sponge- associated fungus Penicillium erubescens KUFA0220. Compounds 1a⁻e, 2a, 3a, 4, 7⁻9, were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 8 exhibited an in vitro growth inhibition of all Gram-positive bacteria whereas 9 showed growth inhibition of methicillin-resistant Staphyllococus aureus (MRSA). None of the compounds were active against Gram-negative bacteria tested.