3,4,3',4'-Bisdehydroxanthomegnin

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Category Antibiotics
Catalog number BBF-00157
CAS 78693-31-9
Molecular Weight 570.46
Molecular Formula C30H18O12

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Description

3,4,3',4'-Bisdehydroxanthomegnin is an antibiotic produced by Nannizzia cajetani.

Specification

Synonyms Bisdehydroxanthomegnin
IUPAC Name 10-hydroxy-8-(10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxobenzo[g]isochromen-8-yl)-7-methoxy-3-methylbenzo[g]isochromene-1,6,9-trione
Canonical SMILES CC1=CC2=CC3=C(C(=C2C(=O)O1)O)C(=O)C(=C(C3=O)OC)C4=C(C(=O)C5=C(C4=O)C(=C6C(=C5)C=C(OC6=O)C)O)OC
InChI InChI=1S/C30H18O12/c1-9-5-11-7-13-17(23(33)15(11)29(37)41-9)25(35)19(27(39-3)21(13)31)20-26(36)18-14(22(32)28(20)40-4)8-12-6-10(2)42-30(38)16(12)24(18)34/h5-8,33-34H,1-4H3
InChI Key XJPVLWVZQWRVSC-UHFFFAOYSA-N

Properties

Appearance Dark red Powder
Boiling Point 882.2±65.0 °C at 760 mmHg
Density 1.7±0.1 g/cm3

Reference Reading

1. 3,4,3'-Tri- O-methylellagic acid as an anticancer agent: in vitro and in silico studies
Andika Pramudya Wardana, Muhammad Ikhlas Abdjan, Nanik Siti Aminah, Mochamad Zakki Fahmi, Imam Siswanto, Alfinda Novi Kristanti, Mirza Ardella Saputra, Yoshiaki Takaya RSC Adv. 2022 Oct 19;12(46):29884-29891. doi: 10.1039/d2ra05246f. eCollection 2022 Oct 17.
We report a natural product compound isolated from Syzygium polycephalum known as 3,4,3'-tri-O-methylellagic acid (T-EA) as a candidate drug for cancer treatment. The characterization of the isolated T-EA compound was carried out using various spectroscopic methods. The in vitro evaluation showcased the inhibition activity of T-EA towards the T47D and HeLa cell lines with EC50 values of 55.35 ± 6.28 μg mL-1 and 12.57 ± 2.22 μg mL-1, respectively. Meanwhile, the in silico evaluation aimed to understand the interaction of T-EA with enzymes responsible for cancer regulation at the molecular level by targeting the hindrance of cyclin-dependent kinase 9 (CDK9) and sirtuin 1 (SIRT1) enzymes. T-EA showed a binding free energy towards the SIRT1 protein of ΔG bind (MM-GBSA): -30.98 ± 0.25 kcal mol-1 and ΔG bind (MM-PBSA): -24.07 ± 0.30 kcal mol-1, while that of CDK9 was ΔG bind (MM-GBSA): -29.50 ± 0.22 kcal mol-1 and ΔG bind (MM-PBSA): -25.87 ± 0.40 kcal mol-1. The obtained results from this research could be considered as important information on 3,4,3'-tri-O-methylellagic acid as a drug to treat cervical and breast cancers.
2. Efficacy of omega-3 PUFAs in depression: A meta-analysis
Yuhua Liao, Bo Xie, Huimin Zhang, Qian He, Lan Guo, Mehala Subramanieapillai, Beifang Fan, Ciyong Lu, Roger S McIntyre Transl Psychiatry. 2019 Aug 5;9(1):190. doi: 10.1038/s41398-019-0515-5.
We conducted this meta-analysis of double-blind randomized placebo-controlled trials to estimate the efficacy of omega-3 polyunsaturated fatty acids (PUFAs), especially docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA), in the improvement of depression. We applied a systematic bibliographic search in PubMed and EMBASE for articles published prior to 20 December 2017. This meta-analysis was performed using RevMan 5.3 and R 3.4.3, and means and standard deviations were calculated in fixed- or random-effects models based on the results of the Q-test. A sensitivity analysis was also conducted to evaluate the stability of the results, and publication bias was evaluated by a funnel plot and Egger's linear regression analysis. Our search resulted in 180 articles; we analyzed 26 studies, which included 2160 participants. The meta-analysis showed an overall beneficial effect of omega-3 polyunsaturated fatty acids on depression symptoms (SMD = -0.28, P = 0.004). Compared with placebo, EPA-pure (=100% EPA) and EPA-major formulations (≥60% EPA) demonstrated clinical benefits with an EPA dosage ≤1 g/d (SMD = -0.50, P = 0.003, and SMD = -1.03, P = 0.03, respectively), whereas DHA-pure and DHA-major formulations did not exhibit such benefits.Current evidence supports the finding that omega-3 PUFAs with EPA ≥ 60% at a dosage of ≤1 g/d would have beneficial effects on depression. Further studies are warranted to examine supplementation with omega-3 PUFAs for specific subgroups of subjects with inflammation, severity of depression, and the dose response for both EPA and DHA supplementation.
3. Dipolar cycloaddition strategy for three-component synthesis of chromeno[3',4':3,4]pyrido[2,1-a]isoquinoline derivatives
Abdolali Alizadeh, Parinaz Jamal, Atefeh Roosta, Reza Rezaiyehraad, Tian-Fu Liu, Mojtaba Khanpour Mol Divers. 2021 May;25(2):701-710. doi: 10.1007/s11030-020-10041-1. Epub 2020 Feb 1.
A rapid and efficient protocol to fused pentacyclic compounds, the chromeno[3',4':3,4]pyrido[2,1-a]isoquinolines, via a diastereoselective 1,4-dipolar cycloaddition reaction of isoquinoline, dialkyl acetylenedicarboxylates, and 3-acetyl coumarins, is described.

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