Hericenone B
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| Category | Mycotoxins |
| Catalog number | BBF-00948 |
| CAS | 126654-53-3 |
| Molecular Weight | 433.54 |
| Molecular Formula | C27H31NO4 |
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Description
Hericenone B is a cytotoxic substance extracted from the fruiting bodies of Hericium erinaceum. It can activate nerve growth factor (NGF) synthesis.
Specification
| IUPAC Name | 6-[(2Z)-3,7-dimethyl-5-oxoocta-2,6-dienyl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3H-isoindol-1-one |
| Canonical SMILES | CC(=CC(=O)CC(=CCC1=C(C=C2CN(C(=O)C2=C1O)CCC3=CC=CC=C3)OC)C)C |
| InChI | InChI=1S/C27H31NO4/c1-18(2)14-22(29)15-19(3)10-11-23-24(32-4)16-21-17-28(27(31)25(21)26(23)30)13-12-20-8-6-5-7-9-20/h5-10,14,16,30H,11-13,15,17H2,1-4H3/b19-10- |
| InChI Key | ZJTHOPGQZOXEJX-GRSHGNNSSA-N |
Properties
| Appearance | Crystal |
| Melting Point | 136-138°C |
Reference Reading
1. Divergent synthesis of bioactive resorcinols isolated from the fruiting bodies of Hericium erinaceum: total syntheses of hericenones A, B, and I, hericenols B-D, and erinacerins A and B
Shoji Kobayashi, Hidetsugu Tamanoi, Yuichi Hasegawa, Yusuke Segawa, Araki Masuyama J Org Chem. 2014 Jun 6;79(11):5227-38. doi: 10.1021/jo500795z. Epub 2014 May 23.
Total syntheses of 5'- and 7'-oxidized geranyl resorcylates isolated from the fruiting bodies of Hericium erinaceum and the submerged cultures of a Stereum species were achieved. Our synthesis features derivatization of a suitably functionalized 5'-oxidized geranyl phthalide as a common intermediate, which was obtained by Stille coupling between the phthalide core and the side chain, into a series of natural products by divergent functional group manipulations. The crucial C5'-oxygen functionality was installed at the initial stage by alkylation by an α-cyano ethoxyethyl ether. From a common synthetic intermediate, eight total syntheses including hericenones A, B, and I, hericenols B-D, and erinacerins A and B were achieved (hericenol B and erinacerin B were synthesized as racemates). The structure of hericenone B established in the isolation paper was unambiguously revised as the carbonyl regioisomer at the lactam moiety.
2. Inhibitory effect of hericenone B from Hericium erinaceus on collagen-induced platelet aggregation
Koichiro Mori, Haruhisa Kikuchi, Yutaro Obara, Masaya Iwashita, Yoshihito Azumi, Satomi Kinugasa, Satoshi Inatomi, Yoshiteru Oshima, Norimichi Nakahata Phytomedicine. 2010 Dec 1;17(14):1082-5. doi: 10.1016/j.phymed.2010.05.004. Epub 2010 Jul 16.
Platelet aggregation in the blood vessel causes thrombosis. Therefore, inhibitors of platelet aggregation promise to be preventive or therapeutic agents of various vascular diseases, including myocardial infarction and stroke. In the present study, we found that hericenone B had a strong anti-platelet activity and it might be a novel compound for antithrombotic therapy possessing a novel mechanism. Prior to this study, we examined anti-platelet aggregation activity of ethanol extracts of several species of mushrooms, and found that extract of Hericium erinaceus potently inhibited platelet aggregation induced by collagen. Therefore, we first fractionated the ethanol extract of H. erinaceus to identify the active substances. The anti-platelet activity of each fraction was determined using washed rabbit platelets. As a result, an active component was isolated and identified as hericenone B. Hericenone B selectively inhibited collagen-induced platelet aggregation, but it did not suppress the aggregation induced by U46619 (TXA₂ analogue), ADP, thrombin, or adrenaline. Furthermore, hericenone B did not inhibit arachidonic acid- or convulxin (GPVI agonist)-induced platelet aggregation. Therefore, hericenone B was considered to block collagen signaling from integrin α2/β1 to arachidonic acid release. Moreover, we found that collagen-induced aggregation was inhibited by hericenone B in human platelets, similar to in rabbit platelets.
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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 ╳
