Pyxinol
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| Category | Others |
| Catalog number | BBF-05099 |
| CAS | 25330-18-1 |
| Molecular Weight | 476.73 |
| Molecular Formula | C30H52O4 |
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Description
Pyxinol is the main metabolite of 20S-protopanaxadiol in the human liver.
Specification
| Synonyms | Pixinol; Dammarane-3β,12β,25-triol, 20,24-epoxy-, (20R,24S)- (8CI); (3β,12β,20R,24S)-20,24-Epoxydammarane-3,12,25-triol |
| IUPAC Name | (3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol |
| Canonical SMILES | CC1(C2CCC3(C(C2(CCC1O)C)CC(C4C3(CCC4C5(CCC(O5)C(C)(C)O)C)C)O)C)C |
| InChI | InChI=1S/C30H52O4/c1-25(2)20-10-15-28(6)21(27(20,5)13-11-22(25)32)17-19(31)24-18(9-14-29(24,28)7)30(8)16-12-23(34-30)26(3,4)33/h18-24,31-33H,9-17H2,1-8H3/t18-,19+,20-,21+,22-,23+,24-,27-,28+,29+,30-/m0/s1 |
| InChI Key | DOAJFZJEGHSYOI-LEJKDQSTSA-N |
Properties
| Boiling Point | 563.8±45.0°C (Predicted) |
| Melting Point | 225-226°C |
| Density | 1.082±0.06 g/cm3 (Predicted) |
Reference Reading
1. Design, synthesis and biological evaluation of novel pyxinol derivatives with anti-heart failure activity
Junli Liu, Yunhe Liu, Hui Yu, Ying Zhang, Alan Chen-Yu Hsu, Mingming Zhang, Yawei Gou, Wei Sun, Fang Wang, Pingya Li, Jinping Liu Biomed Pharmacother. 2021 Jan;133:111050. doi: 10.1016/j.biopha.2020.111050. Epub 2020 Nov 30.
Heart failure (HF) is an important and leading cause of substantial morbidity and mortality globally. The angiotensin-converting enzymatic (ACE) is the causative source for congestive heart failure. Natural products and its derivatives play a vital role in drug discovery and development owing to their efficacy and low toxicity. Pyxinol is a potent natural agent for cardiovascular disease. Thus we investigated the effect on ACE and HF of pyxinol derivatives. We designed and synthesized 32 novel fatty acid ester derivatives of pyxinol via esterification. Among them, compounds 2e (IC50=105 nM) and 3b (IC50=114 nM) displayed excellent ACE inhibitory activity in vitro, and exhibited non-toxic to H9c2 cells. The interactions between ACE and compounds were predicted by molecular docking respectively. In verapamil-induced zebrafish HF model, the activity assay showed that these two derivatives could improve cardiovascular physiological indexes including heart beats, venous congestion, heart dilation, cardiac output, ejection fraction and fractional shortening in a dose-dependent manner. A UPLC-QTOF-MS-based serum metabolomics approach was applied to explore the latent mechanism. A total of 25 differentiated metabolites and 8 perturbed metabolic pathways were identified. These results indicated that pyxinol fatty acid ester derivatives 2e and 3b might be considered as potent drug candidates against heart failure and deserved further research and development.
2. Protective Effect of Pyxinol, One Active Ingredient of Lichenes on Cisplatin-Induced Nephrotoxicity via Ameliorating DNA Damage Response
Yanting Yang, Xiuhong Zhu, Guohua Yu, Jinbo Ma Front Pharmacol. 2021 Sep 6;12:735731. doi: 10.3389/fphar.2021.735731. eCollection 2021.
Background: Cisplatin is a valuable chemotherapeutic agent against malignant tumors. However, the clinical use of cisplatin is limited by its side effects such as renal injury. Pyxinol is an active constituent of Lichenes and its effects on cisplatin-induced nephrotoxicity is currently unknown. This study aims to examine the potential protective effects of pyxinol on cisplatin-induced renal injury and explore the underlying mechanisms. Methods: In vivo rat model of cisplatin-induced nephrotoxicity was induced by intraperitoneal (i.p) administration of cisplatin. The blood urea nitrogen and creatinine levels were measured and renal histological analysis was conducted to evaluate the renal function; The TUNEL staining, western blotting and real-time PCR assays were conducted to examine related molecular changes. Finally, the in vivo anti-tumor efficacy was examined in the xenograft tumor model using nude mice. Results: Pretreatment with pyxinol attenuated cisplatin-induced increase in blood urea nitrogen, creatinine and urinary protein excretion and the magnitude of injury in the renal tubules. Pyxinol ameliorated the activation of p53 via attenuating the DNA damage response, which then attenuated the tubular cell apoptosis. Finally, pyxinol could potentiate the in vivo anti-tumor efficacy of cisplatin against the xenograft tumor of cervical cancer cells in nude mice. Conclusions: Combining pyxinol with cisplatin could alleviate cisplatin-induced renal injury without decreasing its therapeutic efficacy, which might represent a beneficial adjunct therapy for cisplatin-based chemotherapeutic regimens in the clinic.
3. Design, Synthesis, and Anti-Inflammatory Activities of 12-Dehydropyxinol Derivatives
Yunxiao Wang, Xiaoliang Mi, Yuan Du, Shuang Li, Liping Yu, Meng Gao, Xiaoyue Yang, Zhihua Song, Hui Yu, Gangqiang Yang Molecules. 2023 Jan 30;28(3):1307. doi: 10.3390/molecules28031307.
Pyxinol skeleton is a promising framework of anti-inflammatory agents formed in the human liver from 20S-protopanaxadiol, the main active aglycone of ginsenosides. In the present study, a new series of amino acid-containing derivatives were produced from 12-dehydropyxinol, a pyxinol oxidation metabolite, and its anti-inflammatory activity was assessed using an NO inhibition assay. Interestingly, the dehydrogenation at C-12 of pyxinol derivatives improved their potency greatly. Furthermore, half of the derivatives exhibited better NO inhibitory activity than hydrocortisone sodium succinate, a glucocorticoid drug. The structure-activity relationship analysis indicated that the kinds of amino acid residues and their hydrophilicity influenced the activity to a great extent, as did R/S stereochemistry at C-24. Of the various derivatives, 5c with an N-Boc-protected phenylalanine residue showed the highest NO inhibitory activity and relatively low cytotoxicity. Moreover, derivative 5c could dose-dependently suppress iNOS, IL-1β, and TNF-α via the MAPK and NF-κB pathways, but not the GR pathway. Overall, pyxinol derivatives hold potential for application as anti-inflammatory agents.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
