Lenthionine

• CAS: 292-46-6
• Catalog Number: ACM292466-1
• Category: Main Products
• Molecular Weight: 188.4
• Molecular Formula: C₂H₄S₅
• Description: Lenthionine is a marine derived natural products found in Chondria acrorhizophora.
• Synonyms: 1,2,3,5,6-Pentasulfur-cylloheptane
• IUPAC Name: 1,2,3,5,6-Pentathiepane
• SMILES: C1SSCSSS1
• InChI: InChI=1S/C2H4S5/c1-3-4-2-6-7-5-1/h1-2H2
• InChI Key: DZKOKXZNCDGVRY-UHFFFAOYSA-N
• Boiling Point: 351.5±45.0 °C (lit.)
• Melting Point: 60-61 °C
• Flash Point: 190.3ºC
• Density: 1.483 g/cm³
• Complexity: 39.3
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Exact Mass: 187.891656
• Heavy Atom Count: 7
• Monoisotopic Mass: 187.891656
• Physical State: Powder
• Storage Conditions: Powder: -20°C for 3 years; In solvent: -80°C for 2 years
• Topological Polar Surface Area: 127 Ų

Case Study

Cyclodextrin Encapsulation of Lenthionine for Controlled Release and Enhanced Antiplatelet Bioavailability

Shimada, Shoichiro, et al. Journal of Food Bioactives 28 (2024). 68-75.

Lenthionine, the key cyclic polysulfur flavor compound responsible for the distinctive aroma of shiitake mushrooms, also exhibits potent antiplatelet aggregation activity both in laboratory assays and in living organisms. However, its volatile and hydrophobic nature severely restricts direct incorporation into food products. Encapsulation within cyclodextrin hosts was investigated as a strategy to overcome these limitations while preserving physiological function.
Experimental Protocol: Lenthionine was complexed with cyclodextrin at varying molar ratios in aqueous solution. The formation and stoichiometry of the inclusion complex were characterized by proton nuclear magnetic resonance spectroscopy at 500 MHz, diffusion-ordered spectroscopy, and two-dimensional rotating-frame Overhauser effect spectroscopy. The amount of included lenthionine was quantified by the phenol-sulfuric acid method. Volatile release was monitored via solid-phase microextraction coupled with gas chromatography-mass spectrometry. Antiplatelet activity was evaluated both in laboratory platelet-rich plasma assays and in an oral administration study using rats.
Performance Evaluation: Spectroscopic analysis confirmed that lenthionine was successfully accommodated within the hydrophobic cavity of cyclodextrin, with chemical shift changes observed for all six proton environments of lenthionine. The inclusion complex significantly suppressed the release of volatile lenthionine compared to the free compound. In animal studies, the complex achieved maximum inhibition of platelet aggregation between 4 and 8 hours after oral administration, an earlier onset than free lenthionine, which peaked at 8 to 16 hours. The accelerated inhibition profile suggests improved dissolution and absorption, expanding the potential for lenthionine in functional food and pharmaceutical formulations.

Elucidating the Molecular Mechanism of Lenthionine-Mediated Platelet Aggregation Suppression

Shimada, Shoichiro, et al. Journal of Food Bioactives 28 (2024). 50-58.

Lenthionine, the cyclic polysulfur compound from shiitake mushrooms containing both disulfide and trisulfide bonds, had previously been shown to inhibit platelet aggregation, but the underlying molecular mechanism remained unresolved. This investigation aimed to map the precise signaling pathway through which lenthionine exerts its antiplatelet effects.
Experimental Protocol: Platelet aggregation was measured by transmittance aggregometry using platelet-rich plasma from healthy human donors. Four agonists with distinct activation mechanisms were employed: platelet-activating factor, adenosine diphosphate, the calcium ionophore A23187, and phorbol 12-myristate 13-acetate. Platelet activation markers including CD62P (P-selectin) and the activated integrin conformation recognized by PAC-1 antibody were assessed by flow cytometry. Morphological changes were visualized by scanning electron microscopy. The phosphorylation status of key signaling proteins was examined by immunoblotting.
Performance Evaluation: Lenthionine demonstrated concentration-dependent inhibition against all four agonists with half-maximal inhibitory concentration values in the sub-millimolar range, indicating that its target lies downstream of multiple activation pathways. Flow cytometry confirmed that lenthionine suppressed both P-selectin surface exposure and integrin activation. Scanning electron microscopy revealed that lenthionine prevented the agonist-induced morphological transition from spherical resting platelets to spread, pseudopodal activated forms. Notably, lenthionine did not alter the phosphorylation or dephosphorylation of myosin light chain, cofilin, or talin, nor did it affect overall protein tyrosine phosphorylation patterns. These findings suggest that lenthionine interferes with platelet aggregation through a mechanism independent of these canonical signaling nodes, possibly involving direct modulation of integrin conformational states via its reactive sulfur moieties.

Biomass-Derived Lenthionine as a Sustainable Sulfur Source for Doping Graphene Electromagnetic Shields

Shahzad, Faisal, et al. ACS Applied Materials & Interfaces 8.14 (2016): 9361-9369.

The proliferation of wireless communication devices has created an urgent need for lightweight, thin, and highly effective electromagnetic interference shielding materials. A novel approach employed lenthionine, a naturally occurring sulfur compound extracted from mushrooms, as a renewable biomass-derived dopant source to enhance the electrical conductivity and shielding performance of reduced graphene oxide.
Experimental Protocol: Graphene oxide was first partially reduced by thermal treatment at 200 degrees Celsius, then reacted with lenthionine at 400 degrees Celsius to incorporate sulfur atoms into the carbon lattice. A subsequent high-temperature annealing step at 1100 degrees Celsius was applied to further graphitize the material. The resulting sulfur-doped graphene was characterized by transmission electron microscopy, X-ray photoelectron spectroscopy, Raman spectroscopy, and four-point probe electrical measurements. Electromagnetic interference shielding effectiveness was evaluated in the X-band frequency range.
Performance Evaluation: The lenthionine-derived sulfur-doped graphene achieved an electrical conductivity of 311 S/cm, representing a 52% improvement over undoped material at 205 S/cm. X-ray photoelectron spectroscopy confirmed successful sulfur incorporation at 1.95 atomic percent, with the dopant atoms acting as n-type donors to increase charge carrier density. The doped material delivered a shielding effectiveness of 38.6 dB, a 61% enhancement over the 24.4 dB measured for undoped graphene. Absorption was identified as the dominant shielding mechanism. This study demonstrates that a naturally occurring mushroom sulfur compound can serve as an effective and sustainable doping agent for producing high-performance electromagnetic shielding materials.

Custom Q&A

What is the molecular formula of Lenthionine?

The molecular formula of Lenthionine is C2H4S5.

What are some synonyms for Lenthionine?

Some synonyms for Lenthionine are 1,2,3,5,6-Pentathiepane and Lenthionin.

What is the molecular weight of Lenthionine?

The molecular weight of Lenthionine is 188.4 g/mol.

Is Lenthionine a natural product?

Yes, Lenthionine is a natural product found in Parkia speciosa and Lentinula edodes.

What is the IUPAC Name of Lenthionine?

The IUPAC Name of Lenthionine is 1,2,3,5,6-pentathiepane.

What is the InChIKey of Lenthionine?

The InChIKey of Lenthionine is DZKOKXZNCDGVRY-UHFFFAOYSA-N.

What is the CAS number of Lenthionine?

The CAS number of Lenthionine is 292-46-6.

What is the boiling point of Lenthionine?

The boiling point of Lenthionine is 287.00 °C at 760.00 mm Hg.

What is the melting point of Lenthionine?

The melting point of Lenthionine is 60 - 61 °C.

How many hydrogen bond acceptors are there in Lenthionine?

There are 5 hydrogen bond acceptors in Lenthionine.