helvolinic acid
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01336 |
| CAS | 10072-61-4 |
| Molecular Weight | 526.66 |
| Molecular Formula | C31H42O7 |
| Purity | >95% |
Online Inquiry
Description
It is produced by the strain of Cephalosporium caerulens. It is a steroidal antibiotic. It has anti-gram-positive bacterial activity.
Specification
| Synonyms | (8α,9β,13α,14β,17Z)-16β-(Acetyloxy)-7α-hydroxy-3,6-dioxo-29-nor-5α-dammara-1,17(20),24-trien-21-oic acid; 29-Nor-8a,9b,13a,14b-dammara-1,17(20),24-trien-21-oicacid,7a,16b-dihydroxy-3,6-dioxo-, 16-acetate, (Z)-(8Cl) |
| IUPAC Name | (2Z)-2-[(4S,5S,6S,8S,9S,10R,13R,14S,16S)-16-acetyloxy-6-hydroxy-4,8,10,14-tetramethyl-3,7-dioxo-5,6,9,11,12,13,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid |
| Canonical SMILES | CC1C2C(C(=O)C3(C(C2(C=CC1=O)C)CCC4C3(CC(C4=C(CCC=C(C)C)C(=O)O)OC(=O)C)C)C)O |
| InChI | InChI=1S/C31H42O7/c1-16(2)9-8-10-19(28(36)37)24-20-11-12-23-29(5)14-13-21(33)17(3)25(29)26(34)27(35)31(23,7)30(20,6)15-22(24)38-18(4)32/h9,13-14,17,20,22-23,25-26,34H,8,10-12,15H2,1-7H3,(H,36,37)/b24-19-/t17-,20+,22+,23+,25-,26+,29-,30+,31-/m1/s1 |
| InChI Key | ZGQQEJUGWPCCHA-SIZJDIOISA-N |
Properties
| Appearance | White Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 202.5-203 °C |
| Solubility | Soluble in Methanol, Ethanol, Acetone, Chloroform; Insoluble in Petroleum Ether |
Reference Reading
1. Genome-Inspired Chemical Exploration of Marine Fungus Aspergillus fumigatus MF071
Jianying Han, Miaomiao Liu, Ian D Jenkins, Xueting Liu, Lixin Zhang, Ronald J Quinn, Yunjiang Feng Mar Drugs. 2020 Jul 6;18(7):352. doi: 10.3390/md18070352.
The marine-derived fungus Aspergillus fumigatus MF071, isolated from sediment collected from the Bohai Sea, China, yielded two new compounds 19S,20-epoxy-18-oxotryprostatin A (1) and 20-hydroxy-18-oxotryprostatin A (2), in addition to 28 known compounds (3-30). The chemical structures were established on the basis of 1D, 2D NMR and HRESIMS spectroscopic data. This is the first report on NMR data of monomethylsulochrin-4-sulphate (4) and pseurotin H (10) as naturally occurring compounds. Compounds 15, 16, 20, 23, and 30 displayed weak antibacterial activity (minimum inhibitory concentration: 100 μg/mL). Compounds 18 and 19 exhibited strong activity against S. aureus (minimum inhibitory concentration: 6.25 and 3.13 μg/mL, respectively) and E. coli (minimum inhibitory concentration: 6.25 and 3.13 μg/mL, respectively). A genomic data analysis revealed the putative biosynthetic gene clusters ftm for fumitremorgins, pso for pseurotins, fga for fumigaclavines, and hel for helvolinic acid. These putative biosynthetic gene clusters fundamentally underpinned the enzymatic and mechanistic function study for the biosynthesis of these compounds. The current study reported two new compounds and biosynthetic gene clusters of fumitremorgins, pseurotins, fumigaclavines and helvolinic acid from Aspergillus fumigatus MF071.
2. New Helvolic Acid Derivatives with Antibacterial Activities from Sarocladium oryzae DX-THL3, an Endophytic Fungus from Dongxiang Wild Rice ( Oryza rufipogon Griff.)
Zhi-Bin Zhang, Si-Yao Du, Bo Ji, Chang-Jiu Ji, Yi-Wen Xiao, Ri-Ming Yan, Du Zhu Molecules. 2021 Mar 24;26(7):1828. doi: 10.3390/molecules26071828.
Three new helvolic acid derivatives (named sarocladilactone A (1), sarocladilactone B (2) and sarocladic acid A (3a)), together with five known compounds (6,16-diacetoxy-25-hy- droxy-3,7-dioxy-29-nordammara-1,17(20)-dien-21-oic acid (3b), helvolic acid (4), helvolinic acid (5), 6-desacetoxy-helvolic acid (6) and 1,2-dihydrohelvolic acid (7)), were isolated from the endophytic fungus DX-THL3, obtained from the leaf of Dongxiang wild rice (Oryza rufipogon Griff.). The structures of the new compounds were elucidated via HR-MS, extensive 1D and 2D NMR analysis and comparison with reported data. Compounds 1, 2, 4, 5, 6 and 7 exhibited potent antibacterial activities. In particular, sarocladilactone B (2), helvolinic acid (5) and 6-desacetoxy-helvolic acid (6) exhibited strongly Staphylococcus aureus inhibitory activity with minimum inhibitory concentration (MIC) values of 4, 1 and 4 μg/mL, respectively. The structure-activity relationship (SAR) of these compounds was primarily summarized.
Recommended Products
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | 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 ╳
