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Laminaran

Alias: beta-1,3-Glucan; Iodus 40; Laminaran
Cat No.:V14201 Purity: ≥98%
Laminaran is a β-1-3-glucan developed from Eisenia Bicyclis, a typical ligand of Dectin-1, with Immune-modulatory, radioprotective and anti-cancer effect.
Laminaran
Laminaran Chemical Structure CAS No.: 9008-22-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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500mg
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Product Description
Laminaran is a β-1-3-glucan developed from Eisenia Bicyclis, a typical ligand of Dectin-1, with Immune-modulatory, radioprotective and anti-cancer effect. Laminaran consists of beta (1→3)-glucan with beta (1→6) branches and can be catalyzed by enzymes like glucosidase (EC 3.2.1.6), which destroys beta (1→3 ) key. Laminaran is a promising immunostimulatory molecule for the study of cancer immunity.
Laminaran (CAS: 9008-22-4), also known as laminarin, is a natural storage β-glucan extracted from the cell walls of brown algae (such as Laminaria species). As a low molecular weight (approximately 4-5 kDa) polysaccharide, its structure consists of a β-(1→3)-D-glucose main chain with少量 β-(1→6) glycosidic linkages as branches. Laminaran exhibits excellent biocompatibility, biodegradability, and low toxicity, leading to its widespread application in functional foods and nutraceuticals. Recently, its biological activities, including immunomodulation, antitumor, anti-inflammatory, antioxidant, and lipid-lowering effects, have attracted considerable attention, and it has been utilized as an oral drug delivery vehicle for macrophage-targeted therapies.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary target of Laminaran is the Dectin-1 receptor, a C-type lectin receptor expressed mainly on the surface of innate immune cells such as macrophages and dendritic cells. Through specific recognition and binding to Dectin-1, Laminaran can mediate targeted delivery and modulate immune responses. Additionally, Laminaran can regulate the expression of Toll-like receptor 2 (TLR2) in gut-associated lymphoid tissue (GALT). In cholesterol metabolism, Laminaran reduces intestinal cholesterol uptake by downregulating NPC1L1 (Niemann-Pick C1-Like 1) protein expression in intestinal epithelial cells, representing a key mechanism for its lipid-lowering effects.
ln Vitro
Laminar polysaccharide (100-800 µg/mL; 24 hours) does not cause any cytotoxicity to human melanoma cells SK-MEL-28 or normal epidermal cells JB6 Cl41. After 24 hours of treatment, the inhibition percentage of viable cell numbers is less than 15% at concentrations as high as 800. The last µg/mL [1]. After 24 and 48 hours of treatment, laminarin (200 µg/mL; 24-72 hours) did not decrease the development of SK-MEL-28 cells; however, after 72 hours of treatment, cell proliferation was reduced by 36%[1]. The phosphorylation of c-Raf (Ser259), ERK1/2 (Tyr202/Tyr204), and MEK1/2 (Ser 221) kinases, as well as total kinases examined protein expression levels, were not affected by low quantities of laminarin (25–50 µg/mL; 24 hours). On the other hand, at 50 µg/mL, p-MEK and p-ERK1/2 will decrease[1].
In vitro studies have demonstrated that Laminaran possesses多种 biological activities. In Caco-2 cells (human colorectal adenocarcinoma cells), Laminaran inhibits BODIPY-cholesterol uptake in a concentration-dependent manner, with an EC50 of 20.69 μM. Further studies indicate that this effect is associated with downregulation of NPC1L1 protein expression, as siRNA-mediated knockdown of NPC1L1 attenuates Laminaran's inhibitory effect on cholesterol uptake. In macrophage targeting studies, Laminaran, as a coating material for nanoscale delivery systems, protects miRNA-223 from nuclease degradation and is selectively taken up by macrophages via Dectin-1 receptor-mediated endocytosis. Furthermore, Laminaran exhibits anti-inflammatory, antioxidant, and antitumor activities in vitro.
ln Vivo
When compared to mice treated with PBS, OVA, and laminarin alone, the combination of laminarin (iv; 12.5, 25, and 50 mg/kg; 21 days) with OVA (50 μg) dramatically decreased tumor mass [3].
In vivo animal models have demonstrated that Laminaran exhibits multiple pharmacological activities. In a mouse model of colitis, oral administration of Laminaran-coated miRNA-223 nanogene delivery system targets macrophages in inflamed colonic regions, promotes M1-to-M2 polarization, and alleviates intestinal inflammation while improving disease outcomes. In high-fat diet (HFD)-fed mice, Laminaran significantly reduces serum total cholesterol (TC), triglycerides (TG), and low-density lipoprotein cholesterol (LDL-C) levels, while decreasing hepatic lipid accumulation and promoting fecal cholesterol excretion. Laminaran also ameliorates local villous damage in the jejunum of HFD-fed mice. In normal mice, gavage administration of Laminaran (1-5 mg/mouse for 14 days) increases CD3, CD19, and Mac-3 positive cell populations, reduces lactate dehydrogenase (LDH) levels, and elevates glutamic pyruvic transaminase (GPT) levels. Furthermore, oral Laminaran administration enhances resistance to Staphylococcus aureus and Candida albicans infection in mice.
Enzyme Assay
Cell-free in vitro assays for Laminaran receptor binding commonly employ surface plasmon resonance (SPR) technology to evaluate binding affinity to the Dectin-1 receptor. The procedure is as follows: Immobilize recombinant Dectin-1 receptor protein on an SPR sensor chip. Inject different concentrations of Laminaran (e.g., 0.1-1000 μg/mL) diluted in running buffer (such as HBS-EP containing 10 mM HEPES, 150 mM NaCl, 3 mM EDTA, 0.005% Tween-20, pH 7.4) at an appropriate flow rate (e.g., 30 μL/min) with a 2-3 min association time and 5-10 min dissociation time. Record association and dissociation curves using a Biacore instrument to calculate binding constants (KD) and kinetic parameters. Alternatively, enzyme-linked immunosorbent assay (ELISA) can be used: coat microplates with Laminaran, incubate with Dectin-1-Fc fusion protein, and detect binding signals using HRP-labeled anti-Fc antibodies.
Cell Assay
Cell Viability Assay[1]
Cell Types: JB6 Cl41 and SK-MEL-28 Cell
Tested Concentrations: 100, 200, 400 and 800 µg/mL
Incubation Duration: 24 hrs (hours)
Experimental Results: No cytotoxicity to normal epidermal cells JB6 Cl41 and human melanoma Cells SK-MEL-28.

Cell proliferation assay[1]
Cell Types: SK-MEL-28 Cell
Tested Concentrations: 200 µg/mL
Incubation Duration: 24 hrs (hours)
Experimental Results: diminished cell proliferation at 72 hrs (hours).

Western Blot Analysis[1]
Cell Types: SK-MEL-28 Cell
Tested Concentrations: 25 µg/mL; 50 µg/mL
Incubation Duration: 24 hrs (hours)
Experimental Results: Inhibition of phosphorylation of c-Raf, MEK1/2 and ERK1/2 kinases.
In vitro cellular assays commonly employ macrophage cell lines (e.g., RAW 264.7, THP-1-differentiated macrophages) or intestinal epithelial cell lines (e.g., Caco-2). For cholesterol uptake assays: seed Caco-2 cells in 96-well plates or confocal culture dishes and culture to confluence. Pre-treat with different concentrations of Laminaran (e.g., 0-100 μM) for 1-2 hours, followed by incubation with BODIPY-labeled cholesterol (2.5 μM) for an additional 2 hours. Wash cells three times with pre-chilled PBS, then quantify intracellular fluorescence using a fluorescence microplate reader (excitation 488 nm, emission 525 nm) or observe cholesterol uptake via confocal microscopy. Use NPC1L1 siRNA knockdown experiments to verify target specificity. For immunomodulatory studies, incubate Laminaran nanoformulations with macrophages, then assess uptake efficiency by flow cytometry and measure cytokine expression by qRT-PCR.
Animal Protocol
Animal/Disease Models: C57BL/6 mice were injected subcutaneously (sc) (sc) with B16-OVA cells [3] Doses: 12.5, 25 and 50 mg/kg; 21-day
Route of Administration: intravenous (iv) (iv)injection
Experimental Results: Prevent B16-OVA tumors by inducing Ag-specific immune responses grow.
In vivo studies of Laminaran employ various animal models. For pharmacokinetic studies, male Sprague-Dawley rats receive oral Laminaran (1 mg/kg), with blood collected at various time points post-administration (0.5, 1, 2, 4, 6, 8, 12, 24 hours); plasma drug concentrations are determined using specific β-glucan detection methods. In the colitis model, C57BL/6 mice receive dextran sulfate sodium (DSS) in drinking water to induce colitis, followed by oral administration of Laminaran-coated miRNA nanoformulation (every other day); monitor body weight changes, disease activity index (DAI), colon length, and histology scores. In the hyperlipidemia model, C57BL/6J mice are fed a high-fat diet (HFD) with concurrent Laminaran administration (50-200 mg/kg/day, gavage) for 4-8 weeks; measure serum lipids, hepatic lipids, and fecal cholesterol. For immunomodulatory studies, BALB/c mice receive Laminaran by gavage (1, 2.5, 5 mg/mouse for 14 days); collect blood for cell phenotype and biochemical analyses.
ADME/Pharmacokinetics
The pharmacokinetic properties of Laminaran have been studied in rats. Following oral administration at a dose of 1 mg/kg, plasma Laminaran concentrations exhibit two peaks between 0.5 and 12 hours, suggesting possible enterohepatic circulation or multiple absorption sites. At 24 hours post-administration, approximately 20 ± 7% of Laminaran remains in the serum. Laminaran is bound and internalized by intestinal epithelial cells and gut-associated lymphoid tissue (GALT) cells in a Dectin-1-independent manner. The liver does not significantly contribute to plasma Laminaran clearance. Regarding physicochemical properties, Laminaran is a white to light yellow powder, slightly soluble in water, soluble in DMSO when heated, with a specific rotation [α]D of -40° to -50° (C=0.9, H₂O). Its molecular formula is C18H32O16 with a molecular weight of approximately 504 g/mol.
Toxicity/Toxicokinetics
Available toxicological studies indicate that Laminaran has a favorable safety profile. According to multiple research sources, Laminaran is described as a non-toxic, biodegradable biopolymer. In product specifications, Laminaran has an RTECS number of OE1523500 and its TSCA status is "Yes" (registered under the US Toxic Substances Control Act). In a 14-day mouse toxicity study, gavage administration of Laminaran (1-5 mg/mouse) did not result in animal death, but dose-dependent decreases in body weight, liver weight, and spleen weight were observed. Notably, Laminaran increased glutamic pyruvic transaminase (GPT) levels while decreasing lactate dehydrogenase (LDH) levels in normal mice, suggesting potential liver-protective rather than hepatotoxic effects. Due to its favorable safety profile, Laminaran is widely used in functional foods. It should be stored in a cool, dry place away from oxidizing agents.
References

[1]. Laminaran from brown alga Dictyota dichotoma and its sulfated derivative as radioprotectors and radiosensitizers in melanoma therapy.Carbohydr Polym. 2019 Feb 15;206:539-547.

[2]. Laminaran. https://en.wikipedia.org/wiki/Laminarin

[3]. Laminarin promotes anti-cancer immunity by the maturation of dendritic cells.Oncotarget. 2017 Jun 13;8(24):38554-38567.

Additional Infomation
Chemical Structure: Laminaran consists of a β-(1→3)-D-glucopyranose main chain with β-(1→6) linkages as branches. Based on the reducing end, there are two chain types: M-type (terminating with 1-O-substituted D-mannitol) and G-type (terminating with D-glucose), with ratios varying by algal species and season. Source: Primarily extracted from brown algae of the family Laminariaceae, commonly from Laminaria, Saccharina, and Eisenia species. Physicochemical Properties: White powder; slightly soluble in water, soluble in DMSO when heated; hygroscopic; specific rotation -45° (C=0.9, water). Synonyms: 昆布多糖, 昆布糖, Laminarin. Research Advances: As a natural biomaterial, Laminaran has been utilized for constructing oral nucleic acid drug delivery systems, nanocarriers for photodynamic therapy, and amphiphilic carrier materials with dual pH/redox sensitivity. IEMDC Status: Not listed. Carcinogenicity: According to available databases, Laminaran has not been classified as a carcinogen by the International Agency for Research on Cancer (IARC).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H32O16
Molecular Weight
504.43
Exact Mass
504.169
CAS #
9008-22-4
PubChem CID
439306
Appearance
White to off-white solid powder
Density
1.8±0.1 g/cm3
Boiling Point
902.8±65.0 °C at 760 mmHg
Flash Point
499.8±34.3 °C
Vapour Pressure
0.0±0.6 mmHg at 25°C
Index of Refraction
1.673
LogP
-6.08
Hydrogen Bond Donor Count
11
Hydrogen Bond Acceptor Count
16
Rotatable Bond Count
7
Heavy Atom Count
34
Complexity
641
Defined Atom Stereocenter Count
12
SMILES
C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OC2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)OC3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
InChi Key
DBTMGCOVALSLOR-VPNXCSTESA-N
InChi Code
InChI=1S/C18H32O16/c19-1-4-7(22)10(25)11(26)17(31-4)34-15-9(24)6(3-21)32-18(13(15)28)33-14-8(23)5(2-20)30-16(29)12(14)27/h4-29H,1-3H2/t4-,5-,6-,7-,8-,9-,10+,11-,12-,13-,14+,15+,16?,17?,18?/m1/s1
Chemical Name
(3R,4S,5R,6R)-4-[(3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol
Synonyms
beta-1,3-Glucan; Iodus 40; Laminaran
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~16.67 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: 33.33 mg/mL (Infinity mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9824 mL 9.9122 mL 19.8244 mL
5 mM 0.3965 mL 1.9824 mL 3.9649 mL
10 mM 0.1982 mL 0.9912 mL 1.9824 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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