(±)-Hyalodendrin
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| Category | Antibiotics |
| Catalog number | BBF-03506 |
| CAS | 40380-24-3 |
| Molecular Weight | 324.42 |
| Molecular Formula | C14H16N2O3S2 |
| Purity | ≥95% |
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Description
(±)-Hyalodendrin is an antibiotic produced by Penicillum turbatum. It has anti-gram-positive bacteria and several viral activities.
Specification
| Related CAS | 53777-19-8 (Deleted CAS) 51920-94-6 ((+)-isomer) |
| Synonyms | 2,3-Dithia-5,7-diazabicyclo[2.2.2]octane-6,8-dione, 1-(hydroxymethyl)-5,7-dimethyl-4-(phenylmethyl)-; Antibiotic A 26771A; 1-Benzyl-1,4-dimethyl-5-hydroxymethyl-2,5-epi-dithio-3,6-diketopiperazine; 1-(Hydroxymethyl)-5,7-dimethyl-4-(phenylmethyl)-2,3-dithia-5,7-diazabicyclo[2.2.2]octane-6,8-dione; 2-Benzyl-1,4-dimethyl-5-hydroxymethyl-2,5-epi-dithia-3,6-diketopiperazine; 2-Benzyl-1,4-dimethyl-5-hydroxymethyl-2,5-epidithiapiperazine-3,6-dione |
| IUPAC Name | 1-benzyl-4-(hydroxymethyl)-5,7-dimethyl-2,3-dithia-5,7-diazabicyclo[2.2.2]octane-6,8-dione |
| Canonical SMILES | CN1C(=O)C2(N(C(=O)C1(SS2)CC3=CC=CC=C3)C)CO |
| InChI | InChI=1S/C14H16N2O3S2/c1-15-12(19)14(9-17)16(2)11(18)13(15,20-21-14)8-10-6-4-3-5-7-10/h3-7,17H,8-9H2,1-2H3 |
| InChI Key | SJRIMIDQFZMJPZ-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; viruses |
| Boiling Point | 580.5±50.0°C at 760 mmHg |
| Melting Point | 105°C |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. A Modular Construction of Epidithiodiketopiperazines
Thomas N Snaddon, Toya D Scaggs, Colin M Pearson, James W B Fyfe Org Lett. 2019 Jun 21;21(12):4873-4877. doi: 10.1021/acs.orglett.9b01770. Epub 2019 Jun 11.
Epidithiodiketopiperazines (ETPs) possess remarkably diverse biological activities and have attracted significant synthetic attention. The preparation of analogues is actively pursued; however, they are structurally challenging, and more direct and modular methods for their synthesis are desirable. To this end, the utility of a bifunctional triketopiperazine building block for the straightforward synthesis of ETPs is reported. A modular strategy consisting of enolate alkylation followed by site-selective nucleophile addition enables the concise synthesis of (±)-hyalodendrin and a range of analogues.
2. Secondary Metabolites from the Culture of the Marine-derived Fungus Paradendryphiella salina PC 362H and Evaluation of the Anticancer Activity of Its Metabolite Hyalodendrin
Ambre Dezaire, Christophe H Marchand, Marine Vallet, Nathalie Ferrand, Soraya Chaouch, Elisabeth Mouray, Annette K Larsen, Michèle Sabbah, Stéphane D Lemaire, Soizic Prado, Alexandre E Escargueil Mar Drugs. 2020 Apr 3;18(4):191. doi: 10.3390/md18040191.
High-throughput screening assays have been designed to identify compounds capable of inhibiting phenotypes involved in cancer aggressiveness. However, most studies used commercially available chemical libraries. This prompted us to explore natural products isolated from marine-derived fungi as a new source of molecules. In this study, we established a chemical library from 99 strains corresponding to 45 molecular operational taxonomic units and evaluated their anticancer activity against the MCF7 epithelial cancer cell line and its invasive stem cell-like MCF7-Sh-WISP2 counterpart. We identified the marine fungal Paradendryphiella salina PC 362H strain, isolated from the brown alga Pelvetia caniculata (PC), as one of the most promising fungi which produce active compounds. Further chemical and biological characterizations of the culture of the Paradendryphiella salina PC 362H strain identified (-)-hyalodendrin as the active secondary metabolite responsible for the cytotoxic activity of the crude extract. The antitumor activity of (-)-hyalodendrin was not only limited to the MCF7 cell lines, but also prominent on cancer cells with invasive phenotypes including colorectal cancer cells resistant to chemotherapy. Further investigations showed that treatment of MCF7-Sh-WISP2 cells with (-)-hyalodendrin induced changes in the phosphorylation status of p53 and altered expression of HSP60, HSP70 and PRAS40 proteins. Altogether, our study reveals that this uninvestigated marine fungal crude extract possesses a strong therapeutic potential against tumor cells with aggressive phenotypes and confirms that members of the epidithiodioxopiperazines are interesting fungal toxins with anticancer activities.
3. Hyalodendrins A and B, New Decalin-Type Tetramic Acid Larvicides from the Endophytic Fungus Hyalodendriella sp. Ponipodef12
Ziling Mao, Weixuan Wang, Ruixue Su, Gan Gu, Zhi Long Liu, Daowan Lai, Ligang Zhou Molecules. 2019 Dec 27;25(1):114. doi: 10.3390/molecules25010114.
Two new decalin/tetramic acid hybrid metabolites, hyalodendrins A (1) and B (2) were isolated from plant endophytic fungus Hyalodendriella sp. Ponipodef12. The structures of the new compounds were elucidated by analysis of the spectroscopic data, including NMR, HRMS and ECD, and by chemical conversion. Compounds 1 and 2 were phomasetin analogues, and both showed potent larvicidal activity against the fourth-instar larvae of Aedes aegypti with the median lethal dose (LC50) values of 10.31 and 5.93 μg/mL, respectively.
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Bio Calculators
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