Ganoderic acid U
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| Category | Bioactive by-products |
| Catalog number | BBF-01479 |
| CAS | 86377-51-7 |
| Molecular Weight | 472.70 |
| Molecular Formula | C30H48O4 |
| Purity | ≥98% by HPLC |
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Description
Ganoderic acid U is a substance isolated from Ganoderma lucidum with anti-tumor activity.
Specification
| Synonyms | (24E)-3α,7α-Dihydroxy-5α-lanosta-8,24-dien-26-oic acid |
| IUPAC Name | (E,6R)-6-[(3R,5R,7R,10S,13R,14R,17R)-3,7-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid |
| Canonical SMILES | CC(CCC=C(C)C(=O)O)C1CCC2(C1(CCC3=C2C(CC4C3(CCC(C4(C)C)O)C)O)C)C |
| InChI | InChI=1S/C30H48O4/c1-18(9-8-10-19(2)26(33)34)20-11-16-30(7)25-21(12-15-29(20,30)6)28(5)14-13-24(32)27(3,4)23(28)17-22(25)31/h10,18,20,22-24,31-32H,8-9,11-17H2,1-7H3,(H,33,34)/b19-10+/t18-,20-,22-,23+,24-,28-,29-,30+/m1/s1 |
| InChI Key | QHLHTTNIUVMWRY-BMGHSXGVSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 166-169°C |
| Solubility | Soluble in Ethanol, Chloroform |
Reference Reading
1. Changes in content of triterpenoids and polysaccharides in Ganoderma lingzhi at different growth stages
Toshinori Nakagawa, Qinchang Zhu, Sonam Tamrakar, Yhiya Amen, Yasuhiro Mori, Hiroto Suhara, Shuhei Kaneko, Hiroko Kawashima, Kotaro Okuzono, Yoshiyuki Inoue, Koichiro Ohnuki, Kuniyoshi Shimizu J Nat Med. 2018 Jun;72(3):734-744. doi: 10.1007/s11418-018-1213-y. Epub 2018 Apr 20.
Ganoderma lingzhi is a traditional medicinal mushroom, and its extract contains many bioactive compounds. Triterpenoids and polysaccharides are the primary bioactive components that contribute to its medicinal properties. In this study, we quantified 18 triterpenoids, total triterpenoid content and total polysaccharide content in the ethanol and water extracts of G. lingzhi at different growth stages. Triterpenoids were quantified by liquid chromatograph-tandem mass spectrometry in the multiple-reaction-monitoring mode. Total triterpenoid and total polysaccharide content were determined by colorimetric analysis. The results indicated that the fruit bodies at an early growth stage had a higher content of ganoderic acid A, C2, I and LM2, as well as of ganoderenic acid C and D, than those at a later growth stage. In contrast, ganoderic acid K, TN and T-Q contents were higher in mature fruit bodies (maturation stage). The highest total triterpenoid and total polysaccharide contents were found in fruit bodies before maturity (stipe elongation stage or early stage of pileus formation). Our results provide information which will contribute to the establishment of an efficient cultivation system for G. lingzhi with a higher content of triterpenoids.
2. Pharmacokinetic, Metabolomic, and Stability Assessment of Ganoderic Acid H Based Triterpenoid Enriched Fraction of Ganoderma lucidum P. Karst
Mohd Hafizur Rehman Ansari, Washim Khan, Rabea Parveen, Sadia Saher, Sayeed Ahmad Metabolites. 2022 Jan 21;12(2):97. doi: 10.3390/metabo12020097.
Ganoderma lucidum P. karst is an edible fungus that is used in traditional medicine and contains triterpenoids as the major phytoconstituents. Ganoderic acids are the most abundant triterpenoids that showed pharmacological activity. As Indian varieties contain ganoderic acid H (GA-H), we aimed to prepare GA-H-based triterpenoid enriched fraction (TEF) and evaluated its pharmacokinetics, metabolomics, and stability analysis. A high-performance liquid chromatography (HPLC) method was developed to quantify GA-H in TEF and rat plasma. Based on GA-H content, a stability assessment and pharmacokinetic study of TEF were also performed. After its oral administration to rats, TEF's the metabolic pattern recognition was performed through ultra-performance liquid chromatography mass spectroscopy (UPLC-MS). The developed HPLC method was found to be simple, sensitive, precise (90% recovery) for the quantification of GA-H. Pharmacokinetic analysis showed that GA-H reached its maximum plasma concentration (Cmax 2509.9 ng/mL) within two hours and sustained quantifiable amount up to 12 h with a low elimination rate (Kel) 0.05 L/h. TEF contained ten bioavailable constituents. The prepared TEF was found to be stable for up to one year at room temperature. The prepared TEF, enriched with ganoderic acid, is stable, contains bioavailable constituents, and can be explored as phytopharmaceuticals for different pharmacological properties. Highlights: (1). Preparation of triterpenoid enriched fraction (TEF) from Ganoderma lucidum. (2). Major triterpenoid in TEF is ganoderic acid H (GA-H). (3). TEF contains several bioavailable phytoconstituents. (4). TEF (considering only GA-H) is stable for up to one year at room temperature. (5). GA-H is rapidly absorbed and has high systemic exposure.
3. Molecular Docking Based Analysis to Elucidate the DNA Topoisomerase IIβ as the Potential Target for the Ganoderic Acid; A Natural Therapeutic Agent in Cancer Therapy
Kaushal K Sharma, Brijendra Singh, Somdutt Mujwar, Prakash S Bisen Curr Comput Aided Drug Des. 2020;16(2):176-189. doi: 10.2174/1573409915666190820144759.
Introduction: Intermediate covalent complex of DNA-Topoisomerase II enzyme is the most promising target of the anticancer drugs to induce apoptosis in cancer cells. Currently, anticancer drug and chemotherapy are facing major challenges i.e., drug resistance, chemical instability and, dose-limiting side effect. Therefore, in this study, natural therapeutic agents (series of Ganoderic acids) were used for the molecular docking simulation against Human DNATopoisomerase II beta complex (PDB ID:3QX3). Methods: Molecular docking studies were performed on a 50 series of ganoderic acids reported in the NCBI-PubChem database and FDA approved anti-cancer drugs, to find out binding energy, an interacting residue at the active site of Human DNA-Topoisomerase II beta and compare with the molecular arrangements of the interacting residue of etoposide with the Human DNA topoisomerase II beta. The autodock 4.2 was used for the molecular docking and pharmacokinetic and toxicity studies were performed for the analysis of physicochemical properties and to check the toxicity effects. Discovery studio software was used for the visualization and analysis of docked pose. Results and conclusion: Ganoderic acids (GS-1, A and DM) were found to be a more suitable competitor inhibitor among the ganoderic acid series with appropriate binding energy, pharmacokinetic profile and no toxicity effects. The interacting residue (Met782, DC-8, DC-11 and DA-12) shared a chemical resemblance with the interacting residue of etoposide present at the active site of human topoisomerase II beta receptor.
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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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
