Product name: Camelliaside B
Synonym name:
Catalogue No.: BP1471
Cas No.: 131573-90-5
Formula: C₃₂H₃₈O₁₉
Mol Weight: 726.637
Botanical Source: Camellia oleifera Abel.
Physical Description:
Type of Compound: Flavonoids

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
Inquire for bulk scale.

Description:

Camelliaside B is a natural product from Camellia oleifera Abel.

References:

J Sci Food Agric. 2011 Oct;91(13):2315-21.    

Isolation and anti-inflammatory effect of astragalin synthesized by enzymatic hydrolysis of tea seed extract.   

The application of tea seed extract (TSE) has been widely investigated because of its biological activities. In this paper, two flavonol triglycosides in TSE-camelliaside A (CamA) and Camelliaside B(CamB)-were subjected to hydrolysis in the presence of two commercial enzyme complexes (Pectinex™ series): Smash and Mash. 

METHODS AND RESULTS:

Smash hydrolyzed only the xylosyl moiety of CamB, and the main product was kaempferol diglycoside (nicotiflorin, NF). On the other hand, Mash induced the hydrolysis of both CamA and CamB, and kaempferol monoglycoside (astragalin, AS) was found to be a main product. Pure AS with > 96% purity was prepared by enzymatic hydrolysis of TSE using Mash, and the chemical structure of AS was confirmed by (1)H- and (13)C-nuclear magnetic resonance analyses. The prepared pure AS showed anti-inflammatory activities by significantly inhibiting cellular nitrite oxide (IC(50) = 363 μg mL(-1)), prostaglandin E(2) (IC(50) = 134 μg mL(-1)) and interleukin-6 production (IC(50) = 289 μg mL(-1)) by lipopolysaccharide -stimulated RAW 264.7 cells. 

CONCLUSIONS:

It was concluded that pure AS can be prepared by enzymatic partial hydrolysis of TSE and employed as an anti-inflammatory material. This is the first study to address the preparation of pure AS from natural sources.    

HPLC of Camelliaside B

HNMR of Camelliaside B

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

Introduction/Overview

Natural products, as an important source of drug discovery and development, play an irreplaceable role in the history of human disease treatment. Flavonoids, as one of the major categories, have attracted much attention due to their wide range of biological activities and low toxicity. Camellia glycoside B (CAS: 131573-90-5) is a type of flavonoid glycoside isolated from the seed residue of Camellia oleifera. Its unique chemical structure endows it with diverse pharmacological activities, especially in the field of anti-tumor, showing great potential. In recent years, with a deeper understanding of the molecular mechanisms of tumor occurrence and development, as well as the rise of multi-target therapy strategies, theanine B has become a research hotspot due to its regulatory effects on multiple key tumor related targets. This article aims to provide a systematic review of the chemical properties, plant sources, pharmacological activities, molecular mechanisms of action, pharmacological evaluation, and clinical application prospects of camellia glycoside B, in order to provide comprehensive scientific references for the in-depth research and development of this natural product.

Chemical structure and physicochemical properties

Camellia glycoside B is a flavonoid glycoside compound. Its molecular formula is C ∝₂ H ∝₈ O ₁₉, and its molecular weight is 726.6370. Its core structure is the flavonol skeleton, which connects multiple sugar groups through glycosidic bonds. The typical structure of camellia glycoside B often contains quercetin or kaempferol as aglycones, which are linked to multiple monosaccharide units such as glucose and rhamnose to form a polysaccharide glycosidic chain. This highly glycosylated structure is the main characteristic that distinguishes it from other simple flavonoid glycosides.

Based on its chemical structure, camellia glycoside B exhibits the following key physicochemical properties:
1. solubility The calculated water solubility value is 4.1618, indicating that it has a certain solubility in water, mainly due to the presence of multiple hydrophilic hydroxyl and sugar groups in the molecule. Meanwhile, it can also dissolve in polar organic solvents such as methanol and ethanol.
2. Lipophilic nature The calculated LogP value is -0.7273, confirming that it is a compound with strong hydrophilicity, and its transmembrane passive diffusion ability may be limited.
3. Polar Surface Area The topologically polar surface area is as high as 308.1200 Å ², which further confirms its strong polarity and hydrophilicity characteristics, and suggests that it may have broad potential for hydrogen bonding interactions with biomolecules such as proteins.
4. Stability As a glycoside compound, it may undergo hydrolysis under acidic or specific enzyme conditions (such as β - glucosidase), releasing aglycones. Glycosides usually have stronger cell membrane permeability, but lower water solubility.

These physical and chemical properties directly affect their bioavailability, in vivo distribution, and subsequent formulation development strategies.

Plant sources and extraction methods

Camellia glycoside B mainly comes from plants of the Camellia genus in the Theaceae family, especially Camellia oleifera Oil tea is an important woody oil crop in China, whose seeds are used to extract tea oil, and the large amount of residue (tea meal) produced after oil extraction is traditionally used as fertilizer or fuel. Research has found that tea meal contains abundant bioactive components, and theaflavins B are one of the important active substances isolated and identified from its methanol extract.

Its extraction and separation usually follow the following process:
1. Raw material pretreatment Oil tea seed meal is dried, crushed, and sieved to obtain a uniform powder.
2. Solvent extraction The most commonly used is methanol or Methanol water Mixing solvents for extraction or reflux extraction. Ethanol is also a feasible alternative solvent due to its high safety. The extraction process may be supplemented with ultrasound, microwave, or heating to improve efficiency.
3. Extraction and Enrichment After vacuum concentration, the crude extract was subjected to liquid-liquid extraction using organic solvents such as petroleum ether, ethyl acetate, and n-butanol in sequence. Camellia glycoside B is mainly enriched in due to its strong polarity n-butanol or water In the middle.
4. Separation and purification: The enriched parts are finely separated by modern chromatographic techniques, such as silica gel column chromatography, reversed phase C18 column chromatography (ODS), Sephadex gel column chromatography (LH-20), high performance liquid chromatography (HPLC) and preparative liquid chromatography (prep HPLC). Structural identification was performed using techniques such as nuclear magnetic resonance (NMR) and mass spectrometry (MS).

This extraction process reflects the "turning waste into treasure" idea of high-value development and utilization of natural active ingredients from agricultural by-products, and has dual economic and environmental significance.

Pharmacological activity research

Numerous in vitro and in vivo studies have shown that camellia glycoside B has a wide range of pharmacological activities, among which Antitumor activity The most prominent and in-depth.

1. Antitumor activity：

   • In vitro cytotoxicity: Theanin B shows growth inhibition and cytotoxicity to a variety of human cancer cell lines, including breast cancer (such as MCF-7), liver cancer (such as HepG2), colon cancer (such as HT-29), lung cancer (such as A549), etc. Its effect is concentration and time-dependent.
   • Inducing cell apoptosis Camellia glycoside B can significantly induce apoptosis in tumor cells, manifested as morphological changes, phosphatidylserine eversion, activation of caspase family proteases, and DNA fragmentation.
   • Inhibit cell migration and invasion Research has shown that camellia glycoside B can effectively inhibit the migration and invasion ability of cancer cells, indicating its potential for anti-tumor metastasis.
   • Inhibit angiogenesis In models such as chicken embryo chorioallantoic membrane, camellian B showed inhibitory effects on neovascularization, which is another important pathway of its anti-tumor effect.
   • In vivo anti-tumor effect In animal models such as nude mice transplanted with tumors, administration of camellia glycoside B can significantly inhibit tumor growth and weight, and has little effect on animal body weight, indicating its safety.

2. Other potential activities Based on the commonality of flavonoids, camellia glycoside B may also have antioxidant, anti-inflammatory and other activities, but there is relatively little specialized research in these areas, which is its future research direction that can be expanded.

Mechanism of action and molecular targets

The anti-tumor effect of camellia glycoside B is not achieved through a single pathway, but through a synergistic regulatory network of multiple targets and pathways, which is consistent with its characteristics as a natural product. The key targets and pathways studied include:

1. Regulating apoptosis related proteins (BCL2 family)Camellia glycoside B can downregulate anti apoptotic proteins BCL2 and MCL1 At the same time, it may upregulate the expression of pro apoptotic proteins (such as BAX), disrupt mitochondrial membrane potential, lead to the release of cytochrome C, and activate endogenous apoptotic pathways.
2. Inhibition of STAT3 signaling pathway Signal Transduction and Transcription Activation Factor 3（STAT3）It is an important oncogenic transcription factor. Camellia glycoside B can inhibit the phosphorylation (activation) of STAT3, prevent its nuclear translocation and transcription of downstream target genes (such as Cyclin D1, BCL2, MMP2), thereby inhibiting cell proliferation, promoting apoptosis, and reducing invasiveness.
3. Intervention in MAPK/ERK pathway Camellia glycoside B pairs MAPK1 (ERK2) The activity has a regulatory effect. The MAPK/ERK pathway regulates cell growth and survival, and its inhibition contributes to the growth inhibitory effect of camellia glycoside B.
4. Inhibition of matrix metalloproteinases (MMPs)Camellia glycoside B can be down regulated MMP2 Expression and activity of gelatinase A. MMP2 is a key enzyme that degrades the extracellular matrix, and its inhibition is one of the core mechanisms by which camellian B inhibits tumor invasion and metastasis.
5. Affects DNA topoisomerase Research suggests that camellia glycoside B may have an impact on TOP1 and TOP2A Has inhibitory effect. Topoisomerase is a key enzyme in DNA replication and transcription, and its inhibition can lead to DNA damage and cell death.
6. Inhibition of hypoxia inducible factor (HIF-1 α)Camellia glycoside B can reduce HIF1A The stability or expression of proteins. HIF-1 α is a core regulatory factor for tumor adaptation to hypoxic microenvironment, and its downregulation can inhibit tumor angiogenesis and glycolysis.
7. Regulating estrogen related pathways Camellia glycoside B pairs ESR1 (estrogen receptor alpha) and CYP19A1 (aromatase) Show regulatory effects. This suggests that it has potential application value in the treatment of hormone dependent tumors (such as some breast cancer), and may play a role by interfering with estrogen synthesis or signal transduction.

In summary, camellia glycoside B forms a synergistic anti-tumor effect network by simultaneously acting on multiple key links such as apoptosis regulation, signal transduction, extracellular matrix remodeling, DNA metabolism, and tumor microenvironment adaptation.

Evaluation of drug properties and pharmacokinetics

Despite the significant pharmacological activity of camellia glycoside B, its drug affinity is the key to determining its successful development as a drug.

1. Preliminary evaluation based on computational parameters：

   • absorb High TPSA (>140 Å ²) and negative LogP values indicate that its oral bioavailability may be low and its passive absorption in the intestine may be poor. It may rely on active transport carriers.
   • distribution: Predict it Low blood-brain barrier permeability This is not beneficial for treating central nervous system tumors, but may reduce central nervous system side effects.
   • Metabolism and toxicity：HERG inhibition risk is' no 'This means that the potential risk of inducing QT interval prolongation in the heart is low, which is a favorable safety signal.The Ames test value is 0.6(It is generally believed that>1.0 has a mutagenic risk), and preliminary indications suggest that it has no significant genetic toxicity.
   • Five rules for classifying drugs Its molecular weight (726.6) far exceeds 500, with a large number of sugar groups, seriously violating multiple of the "Five Rules" (such as molecular weight<500, hydrogen bond donor<5, hydrogen bond acceptor<10), which is a huge development challenge from the perspective of traditional small molecule drugs.

2. Pharmacokinetic challenges and strategies：

   • challenge Camellia glycoside B, as a highly polar glycoside class, is expected to have problems such as poor oral absorption, significant first pass effects, rapid metabolism in vivo (possibly hydrolyzed into aglycones by glycosidases in gut microbiota or tissues), and low systemic exposure.
   • Research status Currently, there is a significant lack of publicly available pharmacokinetic studies (such as in vivo ADME) data on the camellia glycoside B system, which is a key shortcoming in its transformation research.
   • Improvement strategy：
     • Prodrug modification Chemical modification of sugar or phenolic hydroxyl groups to prepare lipophilic prodrugs, improve membrane permeability, and convert them into active ingredients in vivo.
     • New drug delivery system Develop nano formulations (such as liposomes, polymer micelles, and nanoparticles) to encapsulate camellia glycoside B, improve its stability, promote intestinal lymphatic absorption, and achieve targeted delivery and sustained release.
     • Simplified structure Using it as a lead compound, synthesize derivatives or analogues with simpler structures and better physicochemical properties.

Clinical application prospects and prospects

The research on camellia glycoside B is in a transitional stage from basic activity discovery to exploration of translational applications.

1. Direct application prospects：

   • As a functional food or health supplement additive Develop food or dietary supplements with potential anti-cancer and antioxidant health benefits by utilizing the natural and safe nature of their source (tea meal).
   • As a lead compound Its rich pharmacological activity and clear multi-target mechanism of action make it a valuable tool for medicinal chemists to optimize and modify its structure Excellent lead compounds The goal is to obtain derivatives with stronger activity and better drug properties.

2. Prospects for drug development：

   • combination therapy Due to its multi-target nature, camellia glycoside B or its optimized products may be used in combination with existing chemotherapy drugs (such as topoisomerase inhibitors and antiestrogenic drugs) to enhance sensitivity, reduce toxicity, and overcome drug resistance.
   • Targeted drug development Developing tumor targeted nano delivery systems is a highly promising direction to address its drug defects. For example, loading camellia glycoside B into nanocarriers that respond to the tumor microenvironment (such as low pH, high MMP) to achieve specific release at the tumor site.
   • Expand the field of diseases Based on the roles of STAT3, MAPK, and other targets in inflammation and autoimmune diseases, the application of camellia glycoside B in non tumor chronic diseases can be explored.

3. Future research focus：

   • In depth mechanism research By utilizing CRISPR-Cas9, proteomics, and other technologies, we can more accurately verify its direct target and draw a more complete signal network map.
   • Systematic pharmacokinetic study Conduct comprehensive in vivo ADME research to clarify its absorption, distribution, metabolism, and excretion patterns, providing a basis for dosage form design.
   • Preclinical safety evaluation Complete standardized preclinical safety assessment studies on acute toxicity, long-term toxicity, reproductive toxicity, etc.
   • Sustainable source assurance Optimize the process of large-scale extraction and purification of camellia glycoside B from Camellia oleifera meal to ensure stable and economical supply of raw materials.

Conclusion

Camellia glycoside B is a flavonoid glycoside with significant anti-tumor activity discovered from the by-products of Camellia oleifera. It exhibits multidimensional effects in inhibiting tumor cell proliferation, inducing apoptosis, preventing invasion and metastasis, and angiogenesis by synergistically regulating multiple key targets such as MCL1, BCL2, STAT3, MMP2, and HIF1A. However, its large molecular weight, strong polarity, and complex sugar based structure constitute the main obstacles to its transformation into traditional small molecule drugs, manifested as low predicted oral bioavailability and drug development challenges. In the future, the research value of camellia glycoside B will focus more on its optimization as a multi-target lead compound, as well as the development of new targeted formulations using modern pharmaceutical technologies, especially nanotechnology. The combination of the multi efficacy advantages of natural products with modern drug design concepts is the key to promoting the clinical application of camellia glycoside B from the laboratory. At the same time, its in-depth development also meets the strategic needs of high-value utilization and sustainable development of agricultural resources, and has important scientific significance and socio-economic value.