Hyperforin
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| Category | Antibiotics |
| Catalog number | BBF-01874 |
| CAS | 11079-53-1 |
| Molecular Weight | 536.78 |
| Molecular Formula | C35H52O4 |
| Purity | >95% |
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Description
Hyperforin is produced by the strain of Hypericum perforatum. It has anti-gram-positive bacterial and mycobacterium activity.
Specification
| Synonyms | hiperforina; hyperforine; (1R,5S,6R,7S)-4-hydroxy-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)-5-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione; Bicyclo[3.3.1]non-3-ene-2,9-dione, 4-hydroxy-6-methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-, (1R,5S,6R,7S)- |
| IUPAC Name | (1R,5R,7S,8R)-4-hydroxy-8-methyl-3,5,7-tris(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-ene-2,9-dione |
| Canonical SMILES | CC(C)C(=O)C12C(=O)C(=C(C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C |
| InChI | InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1 |
| InChI Key | KGSZHKRKHXOAMG-HQKKAZOISA-N |
Properties
| Appearance | Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 616.825°C at 760 mmHg |
| Melting Point | 75-80°C |
| Density | 1.010±0.06 g/cm3 |
Reference Reading
1. Enantioselective Total Synthesis of Hyperforin and Pyrohyperforin
Yunpeng Ji, Benke Hong, Ivan Franzoni, Mengyang Wang, Weiqiang Guan, Hongli Jia, Houhua Li Angew Chem Int Ed Engl. 2022 Apr 11;61(16):e202116136. doi: 10.1002/anie.202116136. Epub 2022 Feb 19.
Capitalizing on the late-stage diversification of an essential 1,3-diene intermediate, we describe herein a 9-step enantioselective total synthesis of (+)-hyperforin and (+)-pyrohyperforin, starting from commercially available allylacetone. Our convergent synthesis features a series of critical reactions: 1) an enantioselective deconjugative α-alkylation of α,β-unsaturated acid using chiral lithium amides as noncovalent stereodirecting auxiliaries; 2) a HfCl4 -mediated carbonyl α-tert-alkylation to forge the intricate bicyclo[3.3.1]nonane framework; 3) an abiotic cascade pyran formation; and 4) a selective 1,4-semihydrogenation of polyenes. During the course of our synthesis, we also identified a 1,2-cyclopropanediol overbred intermediate which was responsible for the 1,3-diene precursor formation through a controlled fragmentation.
2. Targeting the biological activity and biosynthesis of hyperforin: a mini-review
Shuqin Liu, Beilei Yu, Jungui Dai, Ridao Chen Chin J Nat Med. 2022 Oct;20(10):721-728. doi: 10.1016/S1875-5364(22)60189-4.
Hyperforin is a representative polycyclic polyprenylated acylphloroglucinols (PPAPs) that exerts a variety of pharmacological activities. The complete biosynthesis pathway of hyperforin has not been elucidated due to its complex structure and unclear genetic background of its source plants. This mini-review focuses on the bioactivity and biosynthesis of hyperforin. These analyses can provide useful insights into the biosynthesis investigations of hyperforin and other PPAPs with complex structures.
3. Hyperforin: A natural lead compound with multiple pharmacological activities
Xin-Xin Li, Yu Yan, Jia Zhang, Kang Ding, Cong-Yuan Xia, Xue-Ge Pan, Yan-Jing Shi, Jie-Kun Xu, Jun He, Wei-Ku Zhang Phytochemistry. 2023 Feb;206:113526. doi: 10.1016/j.phytochem.2022.113526. Epub 2022 Nov 26.
Hypericum perforatum L. (Clusiaceae), commonly known as St. John's wort, has a rich historical background as one of the oldest and most widely studied herbal medicines. Hyperforin is the main antidepressant active ingredient of St. John's wort. In recent years, hyperforin has attached increasing attention due to its multiple pharmacological activities. In this review, the information on hyperforin was systematically summarized. Hyperforin is considered to be a lead compound with diverse pharmacological activities including anti-depression, anti-tumor, anti-dementia, anti-diabetes and others. It can be obtained by extraction and synthesis. Further pharmacological studies and more precise detection methods will help develop a value for hyperforin. In addition, structural modification and pharmaceutical preparation technology will be beneficial to promoting the research progress of hyperforin based innovative drugs. Although these works are full of known and unknown challenges, researchers are still expected to make hyperforin play a greater value.
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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 ╳
