Cryptoporic acid A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-01084 |
| CAS | 113592-87-3 |
| Molecular Weight | 412.52 |
| Molecular Formula | C22H36O7 |
Online Inquiry
Description
It is produced by the strain of Cryptoporus volvatus.
Specification
| Synonyms | (2R,3S)-3-Methoxycarbonyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethoxy)-pentanedioic acid 1-methyl ester |
| IUPAC Name | (3S,4R)-4-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methoxy]-5-methoxy-3-methoxycarbonyl-5-oxopentanoic acid |
| Canonical SMILES | CC1(CCCC2(C1CCC(=C)C2COC(C(CC(=O)O)C(=O)OC)C(=O)OC)C)C |
| InChI | InChI=1S/C23H36O7/c1-14-8-9-17-22(2,3)10-7-11-23(17,4)16(14)13-30-19(21(27)29-6)15(12-18(24)25)20(26)28-5/h15-17,19H,1,7-13H2,2-6H3,(H,24,25)/t15-,16-,17-,19+,23+/m0/s1 |
| InChI Key | OCKYURAITHEIMQ-UGECPWBJSA-N |
Properties
| Appearance | Oily Matter |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Species Prioritization Based on Spectral Dissimilarity: A Case Study of Polyporoid Fungal Species
Huong T Pham, Kwang Ho Lee, Eunah Jeong, Sunmin Woo, Jinsuh Yu, Woo-Young Kim, Young Woon Lim, Ki Hyun Kim, Kyo Bin Kang J Nat Prod. 2021 Feb 26;84(2):298-309. doi: 10.1021/acs.jnatprod.0c00977. Epub 2021 Feb 2.
Biological species collections are critical for natural product drug discovery programs. However, prioritization of target species in massive collections remains difficult. Here, we introduce an untargeted metabolomics-based prioritization workflow that uses MS/MS molecular networking to estimate scaffold-level distribution. As a demonstration, we applied the workflow to 40 polyporoid fungal species. Nine species were prioritized as candidates based on the chemical structural and compositional similarity (CSCS) metric. Most of the selected species showed relatively higher richness and uniqueness of metabolites than those of the others. Cryptoporus volvatus, one of the prioritized species, was investigated further. The chemical profiles of the extracts of C. volvatus culture and fruiting bodies were compared, and it was shown that derivative-level diversity was higher in the fruiting bodies; meanwhile, scaffold-level diversity was similar. This showed that the compounds found from a cultured fungus can also be isolated in wild mushrooms. Targeted isolation of the fruiting body extract yielded three unknown (1-3) and six known (4-9) cryptoporic acid derivatives, which are drimane-type sesquiterpenes with isocitric acid moieties that have been reported in this species. Cryptoporic acid T (1) is a trimeric cryptoporic acid reported for the first time. Compounds 2 and 5 exhibited cytotoxicity against HCT-116 cell lines with IC50 values of 4.3 and 3.6 μM, respectively.
2. Cryptoporic acid S, a new drimane-type sesquiterpene ether of isocitric acid from the fruiting bodies of Cryptoporus volvatus
Jun-Chi Wang, Guang-Zhi Li, Na Lv, Lian-Gang Shen, Lei-Ling Shi, Jian-Yong Si J Asian Nat Prod Res. 2017 Jul;19(7):719-724. doi: 10.1080/10286020.2016.1240170. Epub 2016 Oct 19.
A new drimane-type sesquiterpene with an isocitric acid moiety, cryptoporic acid S (1), together with six known compounds, cryptoporic acid D (2), β-sitosterol (3), β-daucosterol (4), stigmast-4-en-3-one (5), ergosterol (6), and (22E,24R)-ergosta-7,22-diene-3β,5α,6β-triol (7), was isolated from the fruiting bodies of Cryptoporus volvatus. The structures of these compounds were established on the basis of UV, IR, MS, 1D and 2D NMR analysis. In the meanwhile, compounds 1 and 2 were evaluated for antioxidant activity using the methods of 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity (DPPH-RSA) and ferric reducing antioxidant power (FRAP) assay, and they exhibited moderate antioxidant activities.
3. Cryptoporic acid E from Cryptoporus volvatus inhibits influenza virus replication in vitro
Li Gao, Jiayuan Han, Jianyong Si, Junchi Wang, Hexiang Wang, Yipeng Sun, Yuhai Bi, Jinhua Liu, Li Cao Antiviral Res. 2017 Jul;143:106-112. doi: 10.1016/j.antiviral.2017.02.010. Epub 2017 Feb 21.
Influenza virus infection is a global public health issue. The efficacy of antiviral agents for influenza virus has been limited by the emergence of drug-resistant virus strains. Thus, there is an urgent need to identify novel antiviral therapies. Our previous studies have found that Cryptoporus volvatus extract can potently inhibit influenza virus replication in vitro and in vivo. However, the effective component of Cryptoporus volvatus, which mediates the antiviral activity, hasn't been identified. Here, we identified a novel anti-influenza virus molecule, Cryptoporic acid E (CAE), from Cryptoporus volvatus. Our results showed that CAE had broad-spectrum anti-influenza activity against 2009 pandemic strain A/Beijing/07/2009 (H1N1/09pdm), seasonal strain A/Beijing/CAS0001/2007(H3N2), mouse adapted strains A/WSN/33 (H1N1), and A/PR8/34 (H1N1). We further investigated the mode of CAE action. Time-course-analysis indicated that CAE exerted its inhibition mainly at the middle stages of the replication cycle of influenza virus. Subsequently, we confirmed that CAE inhibited influenza virus RNA polymerase activity and blocked virus RNA replication and transcription in MDCK cells. In addition, we found that CAE also impaired influenza virus infectivity by directly targeting virus particles. Our data suggest that CAE is a major effective component of Cryptoporus volvatus.
Recommended Products
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
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 ╳
