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Dehydrocyclopeptine Sale

目录号 : GC43402

An intermediate in the synthesis of benzodiazepine alkaloids in Penicillium

Dehydrocyclopeptine Chemical Structure

Cas No.:31965-37-4

规格 价格 库存
1mg
¥2,998.00
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5mg
¥13,500.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

Dehydrocyclopeptine is an intermediate in the synthesis of benzodiazepine alkaloids in Penicillium. It is formed when the 3S-isomer of cyclopeptine undergoes reversible transformation by cyclopeptine dehydrogenase to displace hydrogens from the 3- and 10-positions of the benzodiazepine core.

Chemical Properties

Cas No. 31965-37-4 SDF
Canonical SMILES O=C(N(C)/C(C(N1)=O)=C\C2=CC=CC=C2)C3=C1C=CC=C3
分子式 C17H14N2O2 分子量 278.3
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 3.5932 mL 17.9662 mL 35.9324 mL
5 mM 0.7186 mL 3.5932 mL 7.1865 mL
10 mM 0.3593 mL 1.7966 mL 3.5932 mL
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Research Update

Secondary metabolites from Penicillium sp. 8PKH isolated from deteriorated rice straws

Z Naturforsch C J Biosci 2019 Nov 26;74(11-12):283-288.PMID:31246580DOI:10.1515/znc-2019-0010.

In the search for bioactive secondary metabolites from terrestrial fungi, four compounds, namely, 3-methyl-3H-quinazolin-4-one (1), aurantiomide C (2), 3-O-methylviridicatin (3), and Dehydrocyclopeptine (4), were isolated from Penicillium sp. 8PKH, fungal strain, isolated from deteriorated rice straws. The structures of the isolated compounds were identified by extensive NMR and mass analyses and comparison with literature data. This is the first report of the structure of 3-methyl-3H-quinazolin-4-one (1) with full NMR spectral data having been previously identified by GC-MS from Piper beetle. Analysis of the non-polar fractions of the strain extract by GC-MS revealed the presence of additional eight compounds: methyl-hexadecanoate, methyl linoleate, methyl-9 (Z)-octadecenoate, methyl-octadecanoate, cis-9-oxabicyclo (6.1.0) nonane, 9,12-octadecadienal (9E,12E), ethyl-(E)-9-octadecenoate, and 3-buten-2-ol. The isolated compounds were evaluated for their antimicrobial and cytotoxic activities and exhibited little or no inhibitory activities against the test strains. The taxonomical characterisation and fermentation of the fungal strain were reported as well.

In Vitro Evaluation of the Photoprotective Potential of Quinolinic Alkaloids Isolated from the Antarctic Marine Fungus Penicillium echinulatum for Topical Use

Mar Biotechnol (NY) 2021 Jun;23(3):357-372.PMID:33811268DOI:10.1007/s10126-021-10030-x.

Marine-derived fungi proved to be a rich source of biologically active compounds. The genus Penicillium has been extensively studied regarding their secondary metabolites and biological applications. However, the photoprotective effects of these metabolites remain underexplored. Herein, the photoprotective potential of Penicillium echinulatum, an Antarctic alga-associated fungus, was assessed by UV absorption, photostability study, and protection from UVA-induced ROS generation assay on human immortalized keratinocytes (HaCaT) and reconstructed human skin (RHS). The photosafety was evaluated by the photoreactivity (OECD TG 495) and phototoxicity assays, performed by 3T3 neutral red uptake (3T3 NRU PT, OECD TG 432) and by the RHS model. Through a bio-guided purification approach, four known alkaloids, (-)-cyclopenin (1), Dehydrocyclopeptine (2), viridicatin (3), and viridicatol (4), were isolated. Compounds 3 and 4 presented absorption in UVB and UVA-II regions and were considered photostable after UVA irradiation. Despite compounds 3 and 4 showed phototoxic potential in 3T3 NRU PT, no phototoxicity was observed in the RHS model (reduction of cell viability < 30%), which indicates their very low acute photoirritation and high photosafety potential in humans. Viridicatin was considered weakly photoreactive, while viridicatol showed no photoreactivity; both compounds inhibited UVA-induced ROS generation in HaCaT cells, although viridicatol was not able to protect the RHS model against UVA-induced ROS production. Thus, the results highlighted the photoprotective and antioxidant potential of metabolites produced by P. echinulatum which can be considered a new class of molecules for photoprotection, since their photosafety and non-cytotoxicity were predicted using recommended in vitro methods for topical use.