Erinacine

Last updated
Chemical structures of erinacines A-I Erinacine A-I.gif
Chemical structures of erinacines A-I

Erinacines are natural substances isolated from Hericium erinaceus . They belong to the group of cyathin diterpenoids (erinacines A-K, P, and Q) and are subjects of pharmacological research.

Contents

Erinacine A

Erinacine A, isolated from the cultured mycelia of Hericium erinaceus , the main representative of this compounds group, has an enhancing effect on nerve growth factor synthesis in vitro . [1] It also increases catecholamine in the central nervous system of rats.[ citation needed ]

Erinacine A has also been prepared by total synthesis. [2]

Erinacine E

Erinacine E is a kappa opioid receptor agonist. [3]

Related Research Articles

<span class="mw-page-title-main">Salvinorin A</span> Chemical compound

Salvinorin A is the main active psychotropic molecule in Salvia divinorum. Salvinorin A is considered a dissociative hallucinogen.

<span class="mw-page-title-main">Opioid receptor</span> Group of biological receptors

Opioid receptors are a group of inhibitory G protein-coupled receptors with opioids as ligands. The endogenous opioids are dynorphins, enkephalins, endorphins, endomorphins and nociceptin. The opioid receptors are ~40% identical to somatostatin receptors (SSTRs). Opioid receptors are distributed widely in the brain, in the spinal cord, on peripheral neurons, and digestive tract.

<span class="mw-page-title-main">Salvinorin</span> Group of chemical compounds

Salvinorins are a group of natural chemical compounds and their structural analogs. Several salvinorins have been isolated from Salvia divinorum. They are classified as diterpenoid furanolactones. Salvinorin A is a hallucinogen with dissociative effects.

<span class="mw-page-title-main">Opioid peptide</span> Class of peptides that bind to opioid receptors

Opioid peptides or opiate peptides are peptides that bind to opioid receptors in the brain; opiates and opioids mimic the effect of these peptides. Such peptides may be produced by the body itself, for example endorphins. The effects of these peptides vary, but they all resemble those of opiates. Brain opioid peptide systems are known to play an important role in motivation, emotion, attachment behaviour, the response to stress and pain, control of food intake, and the rewarding effects of alcohol and nicotine.

κ-opioid receptor Protein-coding gene in the species Homo sapiens, named for ketazocine

The κ-opioid receptor or kappa opioid receptor, abbreviated KOR or KOP for its ligand ketazocine, is a G protein-coupled receptor that in humans is encoded by the OPRK1 gene. The KOR is coupled to the G protein Gi/G0 and is one of four related receptors that bind opioid-like compounds in the brain and are responsible for mediating the effects of these compounds. These effects include altering nociception, consciousness, motor control, and mood. Dysregulation of this receptor system has been implicated in alcohol and drug addiction.

<i>Hericium erinaceus</i> Edible mushroom

Hericium erinaceus is an edible mushroom belonging to the tooth fungus group. Native to North America, Europe, and Asia, it can be identified by its long spines, occurrence on hardwoods, and tendency to grow a single clump of dangling spines. The fruit bodies can be harvested for culinary use.

<span class="mw-page-title-main">Metazocine</span> Opioid analgesic

Metazocine is an opioid analgesic related to pentazocine. While metazocine has significant analgesic effects, mediated through a mixed agonist–antagonist action at the mu opioid receptor, its clinical use is limited by dysphoric and hallucinogenic effects which are most likely caused by activity at kappa opioid receptors and/or sigma receptors.

<span class="mw-page-title-main">SNC-80</span> Opioid analgesic drug

SNC-80 is an opioid analgesic compound that selectively activates μ–δ opioid receptor heteromers and is used in scientific research. It was discovered in 1994.

<span class="mw-page-title-main">Enadoline</span> Chemical compound

Enadoline is a drug which acts as a highly selective κ-opioid agonist.

<span class="mw-page-title-main">Spiradoline</span> A κ-opioid agonist drug

Spiradoline (U-62066) is a drug which acts as a highly selective κ-opioid agonist. It has analgesic, diuretic, and antitussive effects, and produces subjective effects in animals similar to those of ketazocine and alazocine. The main effect in humans is sedation, along with analgesic and diuretic effects, but significant side effects such as dysphoria and hallucinations have stopped it from being used clinically.

<span class="mw-page-title-main">HZ-2</span> Chemical compound

HZ-2 is a drug which acts as a highly selective κ-opioid agonist. It is a potent analgesic with around the same potency as morphine, with a long duration of action and high oral bioavailability. Side effects include sedation, nausea and dysphoria as well as diuretic effects.

<span class="mw-page-title-main">U-50488</span> Chemical compound

U-50488 is a drug which acts as a highly selective κ-opioid agonist, but without any μ-opioid antagonist effects. It has analgesic, diuretic and antitussive effects, and reverses the memory impairment produced by anticholinergic drugs. U-50488 was one of the first selective kappa agonists invented and research on its derivatives has led to the development of a large family of related compounds. This compound has never received FDA approval and there are no reported human cases in the literature involving an U-50488 overdose.

<span class="mw-page-title-main">Cinobufagin</span> Chemical compound

Cinobufagin is a cardiotoxic bufanolide steroid secreted by the Asiatic toad Bufo gargarizans. It has similar effects to digitalis and is used in traditional Chinese medicine.

<i>Hericium</i> Genus of fungi

Hericium is a genus of edible mushrooms in the family Hericiaceae. Species in this genus are white and fleshy and grow on dead or dying wood; fruiting bodies resemble a mass of fragile icicle-like spines that are suspended from either a branched supporting framework or from a tough, unbranched cushion of tissue. This distinctive structure has earned Hericium species a variety of common names—monkey's head, lion's mane, and bear's head are examples. Taxonomically, this genus was previously placed within the order Aphyllophorales, but recent molecular studies now place it in the Russulales.

<i>Rhodocollybia maculata</i> Species of fungus

Rhodocollybia maculata, commonly known as the spotted toughshank, is a species of basidiomycete fungus in the family Marasmiaceae. It often appears in decomposing conifer duff. R. maculata is a source of collybolide, a sesquiterpenoid containing a furyl-ẟ-lactone motif reminiscent of salvinorin A.

<span class="mw-page-title-main">Mitragynine pseudoindoxyl</span> Opioid analgesic compound

Mitragynine pseudoindoxyl is a rearrangement product of 7-hydroxymitragynine and active metabolite of mitragynine. It is an analgesic being more potent than morphine.

<span class="mw-page-title-main">Hericenone</span> Class of chemical compounds

Hericenones is a class of benzaldehydes that are isolates of the fruiting body of Hericium erinaceum that promote nerve growth factor synthesis in vitro.

<span class="mw-page-title-main">RB-64</span> Chemical compound

RB-64 is a semi-synthetic derivative of salvinorin A. It is an irreversible agonist, with a reactive thiocyanate group that forms a bond to the κ-opioid receptor (KOR), resulting in very high potency. It is functionally selective, activating G proteins more potently than β-arrestin-2. RB-64 has a bias factor of up to 96 and is analgesic with fewer of the side-effects associated with unbiased KOR agonists. The analgesia is long-lasting. Compared with unbiased agonists, RB-64 evokes considerably less receptor internalization.

<span class="mw-page-title-main">Collybolide</span> Chemical compound

Collybolide is a secondary metabolite of the Rhodocollybia maculata mushroom, a basidiomycete fungus that grows on rotting conifer wood. It was previously believed to be a potent and selective kappa-opioid receptor agonist. However, a total synthesis and independent biological assay determined that collybolide neither excites nor suppresses kappa-opioid receptor signaling. Collybolide is unlikely to be psychoactive, although it has been shown to inhibit L-type calcium channels in isolated rat aorta.

References

  1. Hirokazu Kawagishi; Atsushi Shimada; Ryoko Shirai; Kenji Okamoto; Fumihiro Ojima; Hideki Sakamoto; Yukio Ishiguro; Shoei Furukawa (1994). "Erinacines A, B and C, strong stimulators of nerve growth factor (NGF)-synthesis, from the mycelia of Hericium erinaceum". Tetrahedron Letters. 35 (10): 1569–1572. doi:10.1016/S0040-4039(00)76760-8.
  2. Barry B. Snider; Nha Huu Vo; Steven V. O'Neil & Bruce M. Foxman (1996). "Synthesis of (±)-Allocyathin B2 and (+)-Erinacine A". J. Am. Chem. Soc. 118 (32): 7644–7645. doi:10.1021/ja9615379.
  3. Saito T, Aoki F, Hirai H, et al. (November 1998). "Erinacine E as a kappa opioid receptor agonist and its new analogs from a basidiomycete, Hericium ramosum". The Journal of Antibiotics. 51 (11): 983–90. doi: 10.7164/antibiotics.51.983 . PMID   9918390.

Further reading