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Synonym name: Bacopaside II
Catalogue No.: BP0227
Cas No.: 382146-66-9
Formula: C47H76O18
Mol Weight: 929.107
Botanical Source: Bacopa monnieri
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:
Bacopaside II is a potential anti-angiogenic agent, it can reduce endothelial cell migration and tubulogenesis and induce apoptosis. Bacopaside II shows antioxidant and antidepressant activities, it can inhibit both basal activity as well as verapamil-stimulated ATPase activity, suggesting its affinity towards P-gp.
References:
Int J Mol Sci. 2018 Feb 26;19(3). pii: E653.
The Aquaporin 1 Inhibitor Bacopaside II Reduces Endothelial Cell Migration and Tubulogenesis and Induces Apoptosis.
Expression of aquaporin-1 (AQP1) in endothelial cells is critical for their migration and angiogenesis in cancer.
METHODS AND RESULTS:
We tested the AQP1 inhibitor, Bacopaside II, derived from medicinal plant Bacopa monnieri, on endothelial cell migration and tube-formation in vitro using mouse endothelial cell lines (2H11 and 3B11) and human umbilical vein endothelial cells (HUVEC). The effect of Bacopaside II on viability, apoptosis, migration and tubulogenesis was assessed by a proliferation assay, annexin-V/propidium iodide flow cytometry, the scratch wound assay and endothelial tube-formation, respectively. Cell viability was reduced significantly for 2H11 at 15 μM (p = 0.037), 3B11 at 12.5 μM (p = 0.017) and HUVEC at 10 μM (p < 0.0001). At 15 μM, the reduced viability was accompanied by an increase in apoptosis of 38%, 50% and 32% for 2H11, 3B11 and HUVEC, respectively. Bacopaside II at ≥10 μM significantly reduced migration of 2H11 (p = 0.0002) and 3B11 (p = 0.034). HUVECs were most sensitive with a significant reduction at ≥7.5 μM (p = 0.037). Tube-formation was reduced with a 15 μM dose for all cell lines and 10 μM for 3B11 (p < 0.0001).
CONCLUSIONS:
These results suggest that Bacopaside II is a potential anti-angiogenic agent.
Heliyon. 2016 Feb 15;2(2):e00068.
Beneficial effects of Bacopa monnieri extract on opioid induced toxicity.
The present study examined the hepatotoxicity and nephrotoxicity of morphine and illicit street heroin and their amelioration by a standardized methanolic extract of Bacopa monnieri (L.) (mBME) in rats.
METHODS AND RESULTS:
Morphine or street heroin was administered at a dose of 20 mg/kg for 14 and 21 days. mBME (40 mg/kg) or ascorbic acid (50 mg/kg) was administered two hours before morphine or street heroin. High performance liquid chromatography (HPLC) was used for the standardization of bacoside-A major components in mBME. The antioxidant potential of mBME was evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay. Administration of morphine and street heroin resulted in marked elevation of serum alanine aminotransferase (ALT), aspartate aminotransferase (AST) and creatinine. Histopathological changes induced by morphine and street heroin after 14 days were of reversible nature while treatment for 21 days was associated with irreversible changes. Pretreatment with mBME or ascorbic acid restored the elevation of serum ALT, AST and creatinine and protected liver and kidneys from the toxicological influence of morphine and street heroin. HPLC analysis showed that mBME contained bacoside-A major components i.e. bacoside A3 (37.5 μg/mg), Bacopaside II (4.62 μg/mg) and bacopasaponin C (1.91 μg/mg). The EC50 for the DPPH free radical scavenging assay revealed that mBME possessed strong antioxidant potential.
METHODS AND RESULTS:
These results concluded that as compared to morphine, street heroin was associated with severe biochemical and histopathological changes in the liver and kidneys. Bacopa monnieri having strong antioxidant potential may provide a beneficial herbal remedy for the efficient management of opioid related hepatotoxicity and nephrotoxicity.
NMR of Bacopaside II
HPLC of Bacopaside II
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
304.7600
-2.0000
-2.0000
No
No
No
Unknown
Unknown
No
Unknown
Bacopaside II (CAS No.: 382146-66-9) is an important triterpene saponin compound isolated from the traditional medicinal plant Bacopa monnieri. As an important medicinal ingredient in India's traditional medicine system—Ayurveda—false purslane has been widely studied for its remarkable neuroprotection, cognitive improvement, and anti-inflammatory effects. In recent years, with the deepening development of natural product pharmacology, pseudopursenoside II has gradually become a research hotspot due to its unique bioactivity, especially its potential roles in anti-tumor, anti-angiogenic effects, and metabolic disease regulation.
Pseudopursenoside II exhibited an inhibitory effect on aquaporin AQP1, thereby exerting anti-angiogenic activity, suggesting its potential value in tumor microenvironment regulation. In addition, this compound exhibits significant cytotoxicity, capable of inducing apoptosis in various cancer cells, and demonstrating strong anti-cancer potential. Meanwhile, pseudopurslanesaponin II is associated with various metabolite-related targets (such as AMPK, SGLT2, etc.), suggesting its promising application in metabolic diseases like hyperglycemia.
This paper aims to systematically review the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity and mechanism of action of Pseudopurslanesaponin II, druggability evaluation, and pharmacokinetic characteristics, and, combined with existing research, explore its clinical application prospects, aiming to provide theoretical basis and research directions for the in-depth development and application of this natural product.
Pseudopursenoside II belongs to the triterpene saponin class of natural products, with a complex molecular formula and a molecular weight of 912.1000 Da. The structural core of this compound is a tetracyclic triterpene backbone, connecting multiple glycosyl residues to form a typical saponin structure. Its LogP value was -2.0000, indicating strong hydrophilicity and good water solubility. The total polar surface area (TPSA) reaches as high as 304.76 Ų, reflecting the presence of a large number of polar groups, especially hydroxyl and glycosyls, which imposes certain limitations on cell membrane permeability.
The molecule of Pseudopursenoside II contains 18 hydrogen bond receptors, further enhancing its binding ability to biological macromolecules such as proteins and enzymes, possibly forming the molecular basis for its multi-target action. Its structure does not show the ability to penetrate the blood-brain barrier, suggesting that its direct role in the central nervous system may be limited.
From a physicochemical property perspective, the high polarity and large molecular weight of pseudopursenoside II may affect its oral bioavailability and distribution in vivo, but its good water solubility is beneficial for solubility issues in formulation development. In the future, structural modification or nanocarrier technology is expected to improve its pharmacokinetic properties.
Saponin II is mainly found in the whole plant of Bacopa monnieri, which is widely distributed in tropical and subtropical regions, especially in India and Southeast Asia. As a traditional herbal medicine, false purslane has been used for thousands of years. Modern pharmacological research has confirmed it contains various active ingredients, including saponins, flavonoids, phenols, and alkaloids.
Common methods for extracting pseudopurslaneside II include solvent extraction and chromatographic separation. Typically, ethanol or methanol is first used for crude extraction, followed by separation and purification of saponins using liquid-liquid separation, silica gel column chromatography, high-performance liquid chromatography (HPLC), and other techniques. In recent years, new technologies such as ultrasound-assisted extraction and microwave-assisted extraction have also been applied to improve extraction efficiency and purity.
Optimizing the extraction process not only affects the yield and purity of the product, but also affects its biological activity. Research shows that different extraction solvents and conditions significantly affect the content and activity of Pseudopurslaneside II, requiring process design tailored to specific application requirements.
Pharmacological studies on the pharmacological activity of Purslane Saponin II have mainly focused on its anti-tumor, anti-angiogenesis, and metabolic regulatory effects.
Multiple in vitro cell experiments have shown that pseudopurslaneside II exhibits significant cytotoxicity against various cancer cell lines (such as breast cancer, colon cancer, and lung cancer cells). Its mechanism of action involves inducing cell cycle blockade and activating intracellular apoptosis signaling pathways (such as mitochondria-dependent pathways and activation of caspase family proteins), thereby promoting cancer cell apoptosis. Additionally, pseudopursenoside II can inhibit cancer cell migration and invasion, slowing tumor progression.
Angiogenesis is a key process for tumor growth and metastasis. Pseudopursenoside II exhibits significant anti-angiogenic activity by inhibiting the function of aquaporin AQP1, interfering with endothelial cell migration and lumen formation. In vivo tumor model studies also support its role in blocking angiogenesis in the tumor microenvironment and inhibiting tumor growth.
Pseudopursenoside II has potential associations with various hyperglycemia-related targets (such as AMPK, SGLT2, GCK, etc.), suggesting that it may lower blood glucose and improve metabolic syndrome by regulating mechanisms such as glucose metabolism, insulin signaling pathways, and glucose transport. Although related research is still in its early stages, its multi-target regulatory characteristics provide new ideas for the treatment of metabolic diseases.
The mechanism of action of pseudopursenoside II is complex, involving multiple signaling pathways and molecular targets.
AQP1 (aquaporin 1) plays an important role in endothelial cell migration and angiogenesis. As an AQP1 inhibitor, pseudopursenoside II blocks transmembrane transport of water molecules, interferes with endothelial cell morphological changes and migration, inhibits angiogenesis, and thereby limits tumor growth and metastasis.
Pseudopursenoside II can activate various apoptosis-related proteins within cells, including caspase-3, caspase-9, and Bax proteins, promoting mitochondrial membrane potential loss and cytochrome C release, thereby initiating the endogenous apoptosis pathway. At the same time, it suppresses the expression of the anti-apoptotic protein Bcl-2, enhances apoptosis signaling, and ultimately leads to programmed death of cancer cells.
Pseudopurslaneside II interacts with various metabolic-related targets:
The multiple regulation of these targets gives Pseudopursaburoside II a potential advantage in the treatment of metabolic diseases.
The druggability evaluation of pseudopurslaneside II shows certain challenges in its physicochemical properties. High molecular weight (912 Da) and high polarity (TPSA 304.76 Ų) limit its ability to pass through cell membranes, potentially leading to lower oral bioavailability. LogP is -2, indicating good water solubility but poor lipid solubility, affecting its distribution in vivo.
The ability to penetrate the blood-brain barrier suggests that its direct efficacy in the central nervous system is limited, making it more suitable for peripheral targeted therapy. Safety indicators such as hepatotoxicity, cardiotoxicity, hERG channel inhibition, and Ames-related mutagenicity remain unclear and require validation through systematic in vivo and vitro toxicology studies.
In terms of pharmacokinetics, there is currently a lack of systematic in vivo metabolic and pharmacokinetic data. Given its complex structure, it may exhibit rapid enterohepatic first-pass effects and metabolic degradation. Future use of drug carrier technology or structural modification will be needed to optimize its in vivo stability and targeting properties.
As a versatile natural product, Pseudopursenoside II has broad clinical application potential. Its antitumor and anti-angiogenic activities make it a potential candidate drug in cancer treatment, especially in combination chemotherapy and targeted therapy, where it may exert synergistic effects.
In the field of metabolic diseases, pseudopursenoside II demonstrates promising application in treating hyperglycemia and related metabolic syndromes by modulating multiple targets to improve glucose metabolism and insulin sensitivity. In the future, combining modern drug design with nanotechnology is expected to overcome druggability limitations and improve clinical translation rates.
Furthermore, the safety of pseudopursenoside II still requires further research, especially in the toxicological assessment of long-term use. Preclinical animal models and early clinical trials will be key steps in verifying their efficacy and safety.
With advances in molecular biology and pharmacological techniques, the mechanism of action of pseudopurslaneside II will be further elucidated, providing a solid foundation for its clinical development. Multidisciplinary collaboration will facilitate the transition from laboratory research to clinical applications.
As an important active ingredient in purslane, Pseudopursenoside II shows broad application prospects in the fields of anti-tumor, anti-angiogenic and metabolic disease treatments due to its unique chemical structure and multi-target pharmacological activity. Although its high polarity and large molecular weight pose certain druggability challenges, modern drug development technologies are expected to overcome these limitations and achieve clinical translation.
Future research should focus on elucidating its detailed mechanism of action, safety evaluation, and pharmacokinetic optimization, promoting Pseudopursenoside II as a model of new natural medicines and providing new strategies and options for related disease treatment.
Shenshuai
Wenjing
Hedandan
