Cryptoporic acid D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01085 |
| CAS | 119979-95-2 |
| Molecular Weight | 816.97 |
| Molecular Formula | C44H64O14 |
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Description
It is produced by the strain of Cryptoporus volvatus.
Specification
| Synonyms | 7,11,24,28-Tetraoxapentacyclo(28.4.0.0(5,34).0(13,18).0(17,22))tetratriacontane-9,26-diacetic acid,8,25-bis(methoxycarbonyl)-13,17,30,34-tetramethyl-4,21-bis(methylene)-10,27-dioxo-,(1R-(1R*,5S*,8R*,9S*,13R*,17S*,18R*,22S*,25R*,26S*,30R*,34S*))- |
| IUPAC Name | 2-[(1S,5R,9S,10R,13S,17R,18S,22R,26S,27R,30S,34R)-26-(carboxymethyl)-10,27-bis(methoxycarbonyl)-1,5,18,22-tetramethyl-14,31-dimethylidene-8,25-dioxo-7,11,24,28-tetraoxapentacyclo[28.4.0.05,34.013,18.017,22]tetratriacontan-9-yl]acetic acid |
| Canonical SMILES | CC12CCCC3(C1CCC(=C)C3COC(C(C(=O)OCC4(CCCC5(C4CCC(=C)C5COC(C(C(=O)OC2)CC(=O)O)C(=O)OC)C)C)CC(=O)O)C(=O)OC)C |
| InChI | InChI=1S/C44H64O14/c1-25-11-13-31-41(3)15-9-17-43(31,5)29(25)21-55-35(39(51)53-7)27(19-33(45)46)37(49)58-24-42(4)16-10-18-44(6)30(26(2)12-14-32(42)44)22-56-36(40(52)54-8)28(20-34(47)48)38(50)57-23-41/h27-32,35-36H,1-2,9-24H2,3-8H3,(H,45,46)(H,47,48)/t27-,28-,29-,30-,31-,32-,35+,36+,41-,42-,43+,44+/m0/s1 |
| InChI Key | OXFMLGZWGZNFCM-UOXLEDAOSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 905.3 °C at 760 mmHg |
| Melting Point | 238-241 °C |
| Density | 1.24 g/cm3 |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Differential effects of cryptoporic acids D and E, inhibitors of superoxide anion radical release, on tumor promotion of okadaic acid in mouse skin
S Matsunaga, H Furuya-Suguri, S Nishiwaki, S Yoshizawa, M Suganuma, T Hashimoto, Y Asakawa, H Fujiki Carcinogenesis. 1991 Jun;12(6):1129-31. doi: 10.1093/carcin/12.6.1129.
Cryptoporic acids D and E, isolated from the fungus Cryptoporus volvatus, are inhibitors of superoxide anion radical release. Cryptoporic acid E inhibited tumor promotion of okadaic acid in two-stage carcinogenesis experiments on mouse skin, initiated with 7,12-dimethylbenz[a]anthracene. Treatment with cryptoporic acid E using two different doses per application, 1 (1.2 mumol) and 5 mg (5.9 mumol), reduced the percentage of tumor-bearing mice from 73.3 to 53.3% and 20.0%, and the average number of tumors per mouse from 4.2 to 2.3 and 0.5 respectively in week 20 of tumor promotion. However, cryptoporic acid D slightly enhanced tumor promotion rather than inhibition of okadaic acid. Cryptoporic acid D was expected to have additional biochemical activities, such as activation of protein kinases. Cryptoporic acid D at concentrations of up to 100 microM activated protein kinase C and stimulated other protein kinase activity in vitro, whereas cryptoporic acid E did not. These two compounds provided differential effects on tumor promotion of okadaic acid on mouse skin.
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.
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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 ╳
