Umbilicaric acid
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-05128 |
| CAS | 30666-92-3 |
| Molecular Weight | 482.44 |
| Molecular Formula | C25H22O10 |
Online Inquiry
Description
Umbilicaric acid is an organic polyphenolic carboxylic acid.
Specification
| IUPAC Name | 2-hydroxy-4-[2-hydroxy-4-(4-hydroxy-2-methoxy-6-methylbenzoyl)oxy-6-methylbenzoyl]oxy-6-methylbenzoic acid |
| Canonical SMILES | CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)OC3=CC(=C(C(=C3)C)C(=O)O)O)O)OC)O |
| InChI | InChI=1S/C25H22O10/c1-11-5-14(26)8-19(33-4)22(11)25(32)35-16-7-13(3)21(18(28)10-16)24(31)34-15-6-12(2)20(23(29)30)17(27)9-15/h5-10,26-28H,1-4H3,(H,29,30) |
| InChI Key | RLRCNRNYRSKNOO-UHFFFAOYSA-N |
Properties
| Boiling Point | 724.2±60.0°C (Predicted) |
| Melting Point | 203°C (dec.) |
| Density | 1.431±0.06 g/cm3 (Predicted) |
Reference Reading
1. Chemotype variations among lichen ecotypes of Umbilicaria aprina as revealed by LC-ESI-MS/MS: a survey of antioxidant phenolics
Hooman Norouzi, Ali Azizi, Mansour Gholami, Mohammad Sohrabi, Joel Boustie Environ Sci Pollut Res Int. 2020 Nov;27(32):40296-40308. doi: 10.1007/s11356-020-10053-2. Epub 2020 Jul 13.
In the present study, we characterized the phytochemical properties, which were specifically associated with phenolic compounds and antioxidant activities in six distinct ecotypes of Umbilicaria aprina Nyl. from Iran (including Kivarestan, Mishan, Takht-e Nader, Tochal, Sabalan, and Sahand) to detect diversities within the species. Total phenolic concentration (TPC) and radical scavenging capacities of U. aprina ecotypes were evaluated. Moreover, qualitative differences between chemical profiles were surveyed using liquid chromatography electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS). Relatively moderate TPCs (Kivarestan = 36.12 ± 2.1, Mishan = 41.59 ± 2.2, Takht-e Nader = 31.85 ± 1.3, Tochal = 37.55 ± 2.3, Sabalan = 28.91 ± 2.5, and Sahand = 31.59 ± 2.2) were observed for ecotypes, but a very strong correlation (r = -0/842) was obtained between TPCs and IC50 values. Based on the results of LC-ESI-MS/MS, the following chemical substances were identified: orsellinic acid (1), lecanoric acid (2), evernic acid (3), gyrophoric acid (4), umbilicaric acid (5), hiascic acid (6), stictic acid (7) methyl hiascic acid (8), and an unknown substance (9). The MS/MS fragmentation scheme for each substance was determined and proposed. Wide discrepancies were observed in the chemical profiles of lichen ecotypes, which may corroborate the influence of ecological locality conditions, for example, altitude and slope aspects on secondary metabolism of lichen species U. aprina. The north-facing and east-facing ecotypes (Sabalan and Mishan, respectively) lacked depsidones (stictic acid) mainly because they receive the least direct radiation. Mishan ecotype, as the only east-facing ecotype, showed the most different chemical profile.
2. A Candidate Gene Cluster for the Bioactive Natural Product Gyrophoric Acid in Lichen-Forming Fungi
Garima Singh, Anjuli Calchera, Dominik Merges, Henrique Valim, Jürgen Otte, Imke Schmitt, Francesco Dal Grande Microbiol Spectr. 2022 Aug 31;10(4):e0010922. doi: 10.1128/spectrum.00109-22. Epub 2022 Jul 14.
Natural products of lichen-forming fungi are structurally diverse and have a variety of medicinal properties. Despite this, they have limited implementation in industry mostly because the corresponding genes are unknown for most of their natural products. Here, we implement a long-read sequencing and bioinformatic approach to identify the putative biosynthetic gene cluster of the bioactive natural product gyrophoric acid (GA). Using 15 high-quality genomes representing nine GA-producing species of the lichen-forming fungal genus Umbilicaria, we identify the most likely GA cluster and investigate the cluster gene organization and composition across the nine species. Our results show that GA clusters are promiscuous within Umbilicaria, and only three genes are conserved across species, including the polyketide synthase (PKS) gene. In addition, our results suggest that the same cluster codes for different, but structurally similar compounds, namely, GA, umbilicaric-, and hiascic acid, bringing new evidence that lichen metabolite diversity is also generated through regulatory mechanisms at the molecular level. Ours is the first study to identify the most likely GA cluster and, thus, provides essential information to open new avenues for biotechnological approaches to producing and modifying GA and similar lichen-derived compounds. GA PKS is the first tridepside PKS to be identified. IMPORTANCE The implementation of natural products in the pharmaceutical industry relies on the possibility of modifying the natural product (NP) pathway to optimize yields and pharmacological effects. Characterization of genes and pathways underlying natural product biosynthesis is a major bottleneck for exploiting the medicinal properties of the natural products. Genome mining is a promising and relatively cost- and time-effective approach to utilize unexplored NP resources for drug discovery. In this study, we identify the most likely gene cluster for the lichen-forming fungal depside gyrophoric acid in nine Umbilicaria species. This compound shows cytotoxic and antiproliferative properties against several cancer cell lines and is also a broad-spectrum antimicrobial agent. This information paves the way for generating GA analogs with modified properties by selective activation/deactivation of genes.
Recommended Products
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-00764 | Cerebroside C | 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 ╳
