Product name: D-Pinitol
Synonym name: 3-O-Methyl-D-chiro-inositol; Matezitol; Sennitol; Cathartomannitol
Catalogue No.: BP0515
Cas No.: 10284-63-6
Formula: C₇H₁₄O₆
Mol Weight: 194.183
Botanical Source: Widely distributed in plants. Produced on a large scale from the heartwood of Pinus lambertiana
Physical Description: Powder
Type of Compound: Miscellaneous

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle

Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.

The product could be supplied from milligrams to grams, up to kilograms
Inquire for bulk scale.

Descriptions:
D-Pinitol is azole nucleoside analogue, as potential antitumor agents; it reduces the migration and the invasion of prostate cancer cells (PC3 and DU145) at noncytotoxic concentrations, reduces mRNA and cell surface expression of αvβ3 integrin, exerts its inhibitory effects by reducing focal adhesion kinase (FAK) phosphorylation, c-Src kinase activity and NF-kB activation; thus, D-pinitol may be a novel anti-metastasis agent for the treatment of prostate cancer metastasis.[1,2]
D-Pinitol has hepatoprotective effects by attenuating hyperglycaemia-mediated pro-inflammatory cytokines and oxidative stress.[3]
D-Pinitol and myo-inositol stimulate translocation of glucose transporter 4 in skeletal muscle of C57BL/6 mice, they have the potential to prevent diabetes mellitus by reducing the postprandial blood glucose level and stimulating GLUT4 translocation in the skeletal muscle.[4]
D-Pinitol significantly inhibits the proliferation of MCF-7 cells in a concentration-dependent manner, while upregulating the expression of p53, Bax and down regulating Bcl-2 and NF-kB, thus, D-pinitol induces apotosis in MCF-7 cells through regulation of proteins of pro- and anti-apoptotic cascades.[5]
D-Pinitol efficiently attenuates the hazardous consequences of the environmental carcinogen 7,12-DMBA through modulating cell surface glycoproteins, membrane protective role both in lysosomal and ATPase compartment via its antioxidant nature which ultimately results in the findings of future innovative remedies for genotoxin mediated hazards.[6]

References:
[1] Tianrong Z, Hongxiang L. Carbohyd Res, 2007, 342(6):865-9.
[2] Lin T H, Tan T W, Tsai T H, et al. Int J Mol Sci, 2013, 14(5):9790-802.
[3] Sivakumar S, Palsamy P, Subramanian S P. Free Radical Res, 2010, 44(6):668-78.
[4] Dang N T, Mukai R, Yoshida K, et al. Biosci Biotech Biochem, 2010, 74(5):1062-7.
[5] Rengarajan T, Nandakumar N, Rajendran P, et al. Asian Pac J Cancer P, 2014, 15(4):1757-62.
[6] Rengarajan T, Nandakumar N, Balasubramanian M P. J Exp Ther Oncol, 2012, 10(1):39-49.
[7] Ling C, Jian H, Yang L V, et al. Chinese Journal of Experimental Traditional Medical Formulae, 2011, 17(5):80-2.

HPLC of D-Pinitol

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

Introduction/Overview

D-Pinitol (CAS No.: 10284-63-6), chemically named 3-O-methyl-D-Quilo-inositol, is a naturally occurring cyclic polyol compound widely found in pine and legume plants. As a natural product with multiple biological activities, D-pine alcohol has attracted widespread attention in the field of natural product pharmacology in recent years due to its significant blood sugar-lowering effects and cardiovascular protective effects. In addition, D-Silantulol also exhibits antiviral and larvicidal activities, indicating its potential multi-target pharmacological value. This paper reviews the chemical structure and physicochemical properties of D-pine alcohol, its plant origins and extraction methods, systematically reviews its pharmacological activity and mechanism of action, explores its druggability and pharmacokinetic characteristics, and looks ahead to its clinical application prospects, providing theoretical basis and practical guidance for subsequent research and development.

Chemical structure and physicochemical properties

D-Slone alcohol has the molecular formula C7H14O6 and a molecular weight of 194.1830. Its structure is 3-O-methyl-D-quilo-inositol, a cyclic hexahydroxy alcohol derivative with high polarity. Its LogP value was -2.0723, indicating strong hydrophilicity of D-sulene alcohol, with water solubility reaching 391.0067 mg/mL, demonstrating good water solubility. The polar surface area (TPSA) is 110.38 Ų, indicating that its molecules have a high number of hydrogen bond donors and acceptors, which facilitate binding to biomacromolecules. Low blood-brain barrier permeability indicates limited penetration ability in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames mutagenic test result was 0.0, indicating good genotoxicity safety.

From a chemical structure perspective, the 3-O-methylation modification of D-sudanol imparts different bioactivity to other inositol isomers, especially showing unique functions in regulating glucose metabolism and signal transduction. Multiple hydroxyl groups in its molecule not only enhance its water solubility but also provide abundant hydrogen bond sites for binding to target proteins.

Plant Origins and Extraction Methods

D-Pinol naturally occurs in various plants, especially those in the Pinaceae and Fabaceae families. Common plants with higher levels include pine (Pinus spp.), soybean (Glycine max), red bean (Vigna angularis), and other legumes. D-Pinol mainly exists in free or bound form in plants, distributed in tissues such as seeds, leaves, and bark.

Traditional methods for extracting D-Silene alcohol mainly include water extraction and alcohol extraction. Generally, hot water or 70%-80% ethanol is used as the solvent, extracted by heating reflux or ultrasound-assisted extraction. The extract is concentrated, centrifuged, and filtered, then purified by column chromatography (such as silica gel columns, ion exchange columns) or high-performance liquid chromatography (HPLC). In recent years, supercritical CO2 extraction and membrane separation technologies have also been applied to improve extraction efficiency and purity.

Optimization of the extraction process mainly focuses on improving the recovery rate and purity of D-pine alcohol while reducing interference from other polysaccharides and impurities in the plants. Some studies have also attempted to efficiently produce D-pine alcohol from plant polysaccharides or inositol derivatives through biotransformation and enzymatic hydrolysis techniques, promoting its large-scale production.

Pharmacological activity research

Blood sugar-lowering effect

D-Silone Alcohol is best known for its remarkable blood sugar-lowering effect. Multiple in and vitro studies have shown that D-sulenol can improve insulin resistance, promote glucose uptake and metabolism, and lower blood sugar levels. In diabetic animal models, oral or injection of D-pine alcohol significantly reduced fasting blood glucose and glucose tolerance, improving the function of islet β cells.

Its hypoglycemic effect is reflected not only in regulating glucose metabolism but also in improving lipid metabolism and reducing antioxidant stress, thereby alleviating the development of diabetes and its complications. Compared with traditional hypoglycemic drugs, D-sudanol has fewer side effects, higher safety, and shows good application potential.

Cardiovascular protective effects

D-Silantol has multiple protective effects on the cardiovascular system, including antioxidant, anti-inflammatory, improved vascular endothelial function, and regulation of blood lipids. Experimental studies have found that D-sulanol can lower dyslipidemia, alleviate atherosclerotic lesions, inhibit myocardial cell apoptosis, and improve myocardial ischemia-reperfusion injury.

By regulating multiple signaling pathways, it alleviates oxidative stress and inflammatory responses, protects cardiovascular tissue from damage, and has potential value as an adjunct therapy for cardiovascular diseases.

Antiviral and larvicidal activity

D-Sulfonol also exhibits certain antiviral activity, capable of inhibiting the replication and infection processes of various viruses. Relevant in vitro experiments have shown that D-sufenol inhibits certain RNA and DNA viruses, possibly by interfering with the virus's entry into cells and replication processes.

In addition, D-suphenol also has a killing effect on certain agricultural pest larvae, demonstrating its potential application value in pesticide development.

Mechanism of action and molecular targets

The pharmacological effects of D-pine alcohol involve multiple signaling pathways and key molecular targets, especially in the anti-diabetic field, where its mechanism of action is relatively clear.

AMPK signaling pathway activates

AMPK (5' AMP-activated protein kinase) is a key regulator of cellular energy metabolism. D-Pinol can activate AMPK (the PRKAA1 subunit), promote glucose uptake and fatty acid oxidation, and improve insulin sensitivity. AMPK activation also inhibits hepatic gluconeogenesis and lowers blood glucose production.

Targets related to glucose transport and metabolism

D-Supinol affects several proteins related to glucose transport and metabolism, including:

• SGLT2 (sodium-glucose cotransporter 2):D-suponol may regulate SGLT2 expression or activity, reduce renal glucose reabsorption, and promote urinary glucose excretion.
• GCK (Glucose Kinase): Promotes glucose phosphorylation and enhances intracellular glucose metabolism.
• SLC2A4 (GLUT4): Promotes the translocation of glucose transporter 4, increasing glucose uptake in muscle and fat tissue.
• IRS1 (insulin receptor substrate 1) and PIK3R1 (phospholipidinositol 3-kinase regulatory subunit): enhance insulin signaling and improve insulin resistance.

Nuclear receptors are regulated by kinases

D-Sulene alcohol regulates PPARG (Peroxisome Proliferator-Activated Receptor γ) expression, promoting lipid metabolism and insulin sensitivity. Its activation of AKT1 (protein kinase B) promotes downstream signal transduction, regulates cellular metabolism, and regulates survival.

DPP4 inhibitory effect

D-Pinol has a certain inhibitory effect on DPP4 (dipeptidyl peptidase 4), prolongs the half-life of glucagon-like peptide-1 (GLP-1), promotes insulin secretion, and lowers blood sugar.

In summary, D-Silenol achieves comprehensive anti-diabetic and cardiovascular protective effects through multi-target and multi-pathway synergistic effects.

Druggability evaluation and pharmacokinetics

Druggability evaluation of D-Silantol shows it has good safety and pharmacokinetic characteristics:

• High water solubility (391.0067 mg/mL), which is beneficial for the development of oral formulations.
• A low LogP value (-2.0723) suggests strong hydrophilicity, and absorption may be limited by cell membrane permeability, but it is suitable for intestinal absorption.
• The blood-brain barrier has low permeability, reducing the risk of central nervous system side effects.
• No hERG channel suppression, reducing the risk of cardiotoxicity.
• Ames test is negative, with low genotoxicity risk.

Pharmacokinetic studies show that D-pine alcohol is rapidly absorbed orally, has a moderate plasma half-life, and is mainly excreted by the kidneys. Its bioavailability is influenced by intestinal transporters and metabolic enzymes. Some studies show high affinity for binding to glucose metabolism-related targets, supporting its potential for oral drug development.

Currently, preclinical safety evaluation and toxicological studies of D-sulenol are relatively sufficient, but further systematic pharmacokinetic and clinical pharmacological studies are needed to clarify its dosing range and long-term safety.

Prospects and outlooks for clinical applications

With the rising incidence of diabetes and cardiovascular diseases, there is an urgent need to develop safe and effective natural blood sugar-lowering and cardiovascular protection drugs. D-Siloneol is a strong candidate for natural antidiabetic drugs due to its multi-target mechanism of action and good safety.

The future clinical application prospects mainly include:

• Diabetes adjunct therapy: As an insulin sensitizer and blood glucose regulator, D-Sulfantol can be used in combination with existing drugs to improve treatment outcomes and reduce side effects.
• Cardiovascular disease prevention and treatment: Through its antioxidant and anti-inflammatory effects, D-sutriol holds promise as an adjunct treatment for atherosclerosis, hyperlipidemia, and myocardial ischemia.
• Antiviral and agricultural applications: Its antiviral and larvicidal activities provide new ideas for the development of novel anti-infective drugs and biopesticides.

However, the clinical promotion of D-Silantol still faces some challenges:

• Pharmacokinetic optimization: It is necessary to improve oral bioavailability and improve in vivo stability.
• Dosage Form Development: Developing stable dosage forms suitable for long-term use.
• Clinical trial validation: Systematically conduct Phase I-III clinical trials to verify efficacy and safety.

Future research should focus on deeply elucidating its molecular mechanisms, optimizing extraction and synthesis processes, and conducting multicenter clinical studies to promote clinical translation of D-Sulenol.

Conclusion

D-Silenol is a naturally occurring 3-O-methyl-D-chilo-inositol, demonstrating broad drug development potential due to its remarkable hypoglycemic and cardiovascular protective effects. Its multi-target and multi-pathway mechanisms provide new strategies for treating diabetes and related metabolic diseases. Its excellent druggability and safety make it a hot topic in pharmacological research of natural products. In the future, as pharmacokinetics and clinical research deepen, D-Silantol is expected to become an important natural drug in the treatment of diabetes and cardiovascular diseases, contributing new strength to human health.