Synonym name:
Catalogue No.: BP0765
Cas No.: 30220-46-3
Formula: C20H28O5
Mol Weight: 348.439
Botanical Source: Semen Euphorbia L.
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams, up to kilograms.
It can be manufactured in GMP plant on request.
For R&D, not for human use Directly!
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Ingenol, CAS number 30220-46-3, is a tetracyclic diterpene natural product derived from the genus Ingenol. Due to its unique chemical structure and remarkable biological activity, it has attracted widespread attention in the field of natural product pharmacology in recent years. As an activator of protein kinase C (PKC), Macroterol exhibits multiple pharmacological activities, especially showing potential therapeutic value in the anti-tumor field. It has inhibitory effects on various tumor cell lines including prostate cancer, and acts by regulating multiple signaling pathways, making it one of the key compounds for studying new cancer treatment strategies.
This paper will systematically review the chemical structure and physicochemical properties of Giant Alpha Ol, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and explore its clinical application prospects and future research directions, aiming to provide theoretical basis and reference for scientific research and drug development in related fields.
Giant terpene is a tetracyclic diterpene compound with a complex cyclic terpene skeleton. Its chemical structure is described as 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one, with a molecular formula of C20H28O5 and a molecular weight of 348.4390. Structurally, Macroalpha is replaced by hydroxyl groups at positions 5, 5a, and 6; methyl groups at positions 1, 1, 7, and 9; hydroxymethyl groups at position 4; and oxygen group group at position 1. Its stereochemical configuration is 1aR, 2S, 5R, 5aR, 6S, 8aS, 9R, and 10aR, demonstrating high stereoselectivity.
In terms of physicochemical properties, the LogP value of Giant Alpha Alcohol is 1.4461, indicating moderate lipid solubility that facilitates cell membrane penetration. The total polar surface area (TPSA) is 97.99 Ų, indicating moderate polarity and favorable binding to biomacromolecules. Water solubility is 0.9142 mg/mL, classifying it as a low-solubility compound, suggesting that solubility improvement strategies should be considered in drug formulation development. Its lower blood-brain barrier permeability reduces the risk of central nervous system toxicity. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test result was 0.0, indicating no significant mutagenicity.
Euphorbia spp. is mainly found in plants of the genus Euphorbia spp., especially species such as Euphorbia peplus and Euphorbia tirucalli. Plants of this genus are widely distributed in tropical and subtropical regions and have long been used in traditional medicine to treat skin diseases and tumors.
Common methods for extracting Giant Alpha Alcohol include solvent extraction, column chromatography separation, and high-performance liquid chromatography (HPLC) purification. Ethanol or methanol is generally used as the preliminary extraction solvent, with ultrasound-assisted extraction or reflux extraction improving extraction efficiency. The crude extract was separated by silica gel column chromatography and combined with thin-layer chromatography (TLC) monitoring, further purified to obtain high-purity Macroethyl Ol. In recent years, supercritical fluid extraction and membrane separation technologies have also been applied to improve extraction efficiency and purity.
Moreover, with the development of synthetic biology and chemical synthesis technologies, the total and semi-synthesis methods for Giant Alpha Alcohol have gradually matured, making large-scale production possible.
As a PKC activator, Macroterol exhibits multiple biological activities, with particularly in-depth research in the anti-tumor field. Its main pharmacological activities include:
Antitumor activity
Macroterol has inhibitory effects on various tumor cell lines, especially prostate cancer cells. In vitro experiments have shown that it can inhibit tumor cell proliferation, induce apoptosis, and block the cell cycle process. Its antitumor effect is partly attributed to the activation of PKCs, which in turn regulate downstream signaling pathways such as MAPK and STAT3, affecting cell survival and proliferation.
Immunomodulatory effects
By activating PKC, Macroterol can regulate immune cell function and promote immune responses. Research shows that it can enhance the activity of macrophages and T cells, and improve anti-tumor immune responses.
Antiviral activity
Some studies have found that Macroethyl has inhibitory effects on certain viruses, possibly blocking viral replication by modulating host cell signaling pathways.
Potential for treating skin diseases
Macrocephal derivatives have been used to treat skin cancer and psoriasis, showing good local application effects.
The core mechanism of action of Macroethyl is to regulate intracellular signaling by activating members of the PKC family. PKC is an important class of serine/threonine protein kinases involved in regulating cell proliferation, differentiation, apoptosis, and immune responses.
In prostate cancer, the key molecular targets of the effects of giant alpha alcohol include:
Macroterol regulates the expression and activity of these targets through PKC activation, thereby affecting tumor cell growth, apoptosis, and drug resistance. Additionally, PKC activation can promote changes in intracellular calcium ion concentration, regulate cytoskeletal reorganization and migration capacity, and influence tumor metastasis.
The drugability of Giant Alpha Alcohol demonstrates certain advantages and challenges:
In the future, further systematic pharmacokinetic studies are needed, including evaluation of absorption, distribution, metabolism, and excretion (ADME) characteristics, as well as toxicological studies, to improve the druggability evaluation system.
As a naturally derived PKC activator, Giant Alpha Alcohol has significant anti-tumor potential, especially showing unique advantages in the treatment of prostate cancer. Through multi-target and multi-pathway synergistic effects, it overcomes the limitations of traditional single-target drugs and has broad clinical application prospects.
Currently, Giant Alpha Alcohol and its derivatives have entered partial preclinical research stages, and some formulations have shown good efficacy for the treatment of topical skin diseases. Future research directions include:
Giant Alpha Alcohol, a unique tetracyclic diterpene natural product, demonstrates great potential as a novel antitumor drug due to its unique chemical structure and multi-target pharmacological activity. It regulates multiple signaling pathways through PKC activation, affecting tumor cell proliferation, apoptosis, and drug resistance, providing new ideas for tumor treatment.
Although there are still certain challenges in extraction and purification, pharmacokinetics, and clinical applications, with the development of modern medicinal chemistry, molecular biology, and pharmaceutical technologies, the research and application prospects for Juju Alpha Alcohol are broad. Future in-depth mechanistic research, structural optimization, and clinical validation will drive Giant Alpha Alcohol from the laboratory to clinical practice, benefiting more patients.
