Synonym name: 7-Hydroxylathyrol
Catalogue No.: BP0097
Cas No.: 34208-98-5
Formula: C₂₀H₃₀O₅
Mol Weight: 350.455
Botanical Source: Euphorbia lathyris

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.

For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.

Description:

Reference standards.

References:

Journal of Molecular Catalysis B: Enzymatic, 2017:S1381117717300279.    

Regioselective hydroxylation of lathyrane diterpenoids biocatalyzed by microorganisms and its application in integrated synthesis.   

METHODS AND RESULTS:

The regioselective oxidation of three lathyrane diterpenoids (lathyrol, 1; 7-beta-Hydroxylathyrol, 2; and Euphorbia factor L3, 3) catalyzed by the fungi Mortierella ramanniana CGMCC 3.03413, Mucor circinelloides CICC 40242, and the actinomycete Nocardia iowensis sp. nov. NRRL 5646 was investigated. Ten new metabolites (4–13) including two unprecedented cyclopropane-rearranged products (4 and 5) have been obtained. Metabolites (6, 10 and 11) were further converted chemically to eight acylated derivatives (6a, 10a–10f and 11a). 

CONCLUSIONS:

The structures of all compounds were elucidated on the basis of extensive NMR and MS data analyses. All the metabolites and enzyme-chemical products were evaluated for their cytotoxicities against three human cancer cell lines as well as their multidrug resistance (MDR) reversing effects in adriamycin (ADM)-resistant human MCF-7 breast cancer cells (MCF-7/ADM). 

HPLC of 7-beta-Hydroxylathyrol

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

7-beta-Hydroxylathyol (CAS No. 34208-98-5) is a natural compound with significant pharmacological activity, belonging to the diterpene alcohol class. This compound was originally isolated from plants of the genus Cylindrium, and due to its unique chemical structure and diverse biological activities, it has attracted widespread attention in the field of natural product pharmacology in recent years. 7-Hydroxycynicin diterpene alcohol demonstrates potential therapeutic effects across various disease models, especially demonstrating unique advantages in the prevention and treatment of neoplastic diseases such as adenomas. Its mechanism of action involves multiple molecular targets, including APP, STAT3, ESR2, and others, suggesting that it may achieve efficacy through coordinated regulation of multiple targets. This paper aims to systematically review the chemical properties, plant origin, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of 7-hydroxy-cylyzine diterpene alcohol, providing a theoretical basis and reference for subsequent research and development.

Chemical structure and physicochemical properties

7-Hydroxycylypine diterpene alcohol is a typical diterpene alcohol compound, with a molecular formula of C_20H_34O_4 and a molecular weight of 346.44. Its structural features include a diterpene framework with a seven-position β-hydroxyl functional group, giving it strong polarity and bioactivity. In terms of physicochemical properties, the compound has a LogP value of 2.55, indicating moderate lipid solubility, which facilitates cell membrane penetration but is less prone to excessive lipophilusis leading to reduced bioavailability. Its topological pole surface area (TPSA) is 92.86 Ų, and it has 5 hydrogen bond acceptors, indicating good affinity and selectivity when binding to biological macromolecules. Although 7-hydroxyquinaziterpene alcohol does not easily cross the blood-brain barrier (BBB), its pharmacological activity in peripheral tissues remains significant. Regarding its safety indicators such as hepatotoxicity, cardiotoxicity, hERG channel inhibition, and genotoxicity (Ames test), there is currently no definitive data and further systematic evaluation is needed.

Plant Origins and Extraction Methods

7-Hydroxycylysine diterpene alcohol mainly comes from plants of the genus Euphorbia, with Euphorbia lathyris being particularly abundant. As a traditional Chinese medicinal herb, Qianjin Zi has long been used to treat various diseases. Its active components are complex, and diterpenoids are one of its main medicinal substances.

The extraction method typically uses organic solvent extraction combined with chromatography separation technology. The specific steps include:

1. Raw material pretreatment: collect Qianjinzi, dry it, and crush it to increase surface area.
2. Solvent extraction by extraction: ethanol or methanol is commonly used as extraction solvents, with reflux or ultrasonic-assisted extraction to improve extraction efficiency.
3. Crude extract concentration: Extract extract is obtained by removing solvents through vacuum concentration.
4. Separation and purification: 7-hydroxycynium diterpene alcohol is separated and purified using silica gel column chromatography, reversed-phase high-performance liquid chromatography (RP-HPLC), and other methods.
5. Structural identification: Confirm compound structure using methods such as nuclear magnetic resonance (NMR), mass spectrometry (MS), infrared spectroscopy (IR), and other methods.

In recent years, supercritical fluid extraction and molecular blotting techniques have also been attempted to improve the extraction purity and efficiency of 7-hydroxy-cylyzonium diterpene alcohol.

Pharmacological activity research

7-Hydroxyquinzinditerpene alcohol exhibits broad pharmacological activity across various in vivo and in vitro models, mainly including anti-tumor, anti-inflammatory, antioxidant, and cellular signaling pathway regulation.

Antitumor activity

Adenomas are a key disease model in the study of 7-hydroxycynicin-diterpene alcohol. In vitro cell experiments have shown that this compound can significantly inhibit the proliferation of adenoma cells and induce apoptosis. Its antitumor effects are related to regulating various signaling pathways, such as inhibiting the STAT3 signaling pathway and blocking the growth and metastasis ability of tumor cells. Additionally, 7-hydroxycynine diterpene alcohol can influence hormone-dependent growth of adenoma cells by regulating ESR2 (estrogen receptor β) expression.

Anti-inflammatory and antioxidant effects

This compound can downregulate the expression of inflammation-related enzymes such as ALOX5 and ALOX15, inhibiting the production of inflammatory mediators and thereby reducing inflammatory responses. It activates the NFE2L2 (nuclear factor red 2-related factor 2) signaling pathway, enhancing cellular antioxidant defense, reducing oxidative stress damage, and possessing potential protective effects.

Other pharmacological effects

7-Hydroxycynical diterpene alcohol also demonstrates the ability to regulate metabolic-related targets NR1H4 (farnesol X receptor) and SIRT1 (silencing information regulatory factor 2-related enzyme 1), suggesting its potential role in metabolic and aging-related diseases.

Mechanism of action and molecular targets

The pharmacological mechanism of 7-hydroxycynine diterpene alcohol is complex, involving regulation of multiple key molecular targets, reflecting its multi-target and multi-pathway characteristics.

• APP (amyloid precursor protein): regulates intracellular signal transduction, which may affect cell proliferation and apoptosis.
• STAT3 (Signal Transduction and Transcription Activator 3): As an important regulatory factor for tumor cell proliferation and immune evasion, 7-hydroxycynical diterpene alcohol blocks the expression of its downstream pro-tumor genes by inhibiting STAT3 activation.
• ESR2 (estrogen receptor β): involved in the occurrence and development of hormone-dependent tumors, regulating cell proliferation and differentiation.
• TYR (tyrosinase): Although mainly related to melanin synthesis, its regulation may affect cellular redox states.
• APEX1 (DNA lyase): involved in DNA repair and cellular stress responses, 7-hydroxycynical diterpene alcohol may protect cells from DNA damage by modulating APEX1.
• ALOX15/ALOX5 (lipoxygenase): mediates inflammatory responses and lipid metabolism; inhibiting its activity helps reduce inflammation.
• NFE2L2 (antioxidant stress regulator): activates antioxidant gene expression and enhances cellular antioxidant capacity.
• NR1H4 (Farnesol X receptor): Regulates bile acid metabolism and lipid homeostasis, affecting metabolic balance.
• SIRT1 (deacetylase): regulates cellular metabolism, lifespan, and stress responses; 7-hydroxycynical diterpene alcohol may delay cellular aging by activating SIRT1.

In summary, 7-hydroxycynium diterpene alcohol regulates cell proliferation, apoptosis, inflammation, and metabolic processes through multi-target synergistic effects, providing a molecular basis for its broad pharmacological activity.

Druggability evaluation and pharmacokinetics

Druggability is a key step in developing natural products into drugs. The molecular weight (346.44) and LogP (2.55) of 7-hydroxycylysine diterpene alcohol both met the Lipinski rule, suggesting good oral bioavailability potential. TPSA was 92.86, which is within the ideal range, which is beneficial for cell membrane penetration and targeted binding.

However, the compound does not easily cross the blood-brain barrier, limiting its application in central nervous system diseases. In terms of safety, there is currently a lack of systematic data on hepatotoxicity, cardiotoxicity, and genotoxicity, which require further clarification through in vivo and in vitro toxicological studies.

Pharmacokinetic research is still in its early stages. In vivo metabolic pathways may involve hydroxylation of liver enzyme systems and glucuronic acid binding, and the activity and safety of these metabolites require further investigation. In the future, in vivo pharmacokinetics (PK) and pharmacokinetic (PD) studies should be combined to optimize dosing regimens and dosage form designs.

Prospects and outlooks for clinical applications

As a multi-target natural product, 7-hydroxycythian diterpene alcohol possesses broad pharmacological activity and good druggable potential, especially demonstrating unique advantages in the prevention and treatment of adenomas and related tumors. Its anti-inflammatory, antioxidant, and metabolic regulatory effects also provide new ideas for the treatment of chronic inflammatory and metabolic diseases.

The key to future clinical applications lies in:

1. Safety evaluation: Systematic toxicological studies to clarify potential adverse reactions and safe dosage ranges.
2. Pharmacokinetic optimization: Improves bioavailability, improves in vivo stability, and reduces the toxicity of metabolic products.
3. Dosage Form Development: Developing dosage forms suitable for clinical applications, such as oral formulations and sustained-release formulations.
4. Clinical trial design: Conduct early-stage clinical trials to verify efficacy and safety, especially in patients with adenomas and related tumors.
5. Multi-target combination therapy: Combining modern drug design concepts to explore synergistic effects with other drugs to enhance therapeutic outcomes.

Moreover, based on the diversity of its molecular targets, 7-hydroxycynicin-diterpene alcohol may also have potential value in neurodegenerative diseases, immunomodulatory, and anti-aging fields, warranting further in-depth study.

Conclusion

As an important natural diterpene alcohol compound, 7-hydroxycynium diterpene alcohol shows broad research and application prospects due to its unique chemical structure and multi-target pharmacological activity. Currently, there is a preliminary understanding of its chemical properties, origins, pharmacological effects, and mechanisms of action, but systematic safety evaluation and clinical translational research still need to be strengthened. In the future, through multidisciplinary collaboration combined with modern drug development technologies, 7-hydroxycyclinediterpene alcohol is expected to advance clinical application, providing new natural drug candidates for the treatment of adenomas and related diseases.