Hypaphorine (Synonyms: L-Hypaphorine, (+)-Tryptophan, Tryptophan Betaine) |
رقم الكتالوجGC38797
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Hypaphorine عبارة عن قلويد إندولي معزول من Pisolithus tinctorius ، وله تأثيرات عصبية وخفض الجلوكوز في القوارض
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 487-58-1
Sample solution is provided at 25 µL, 10mM.
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Hypaphorine, an indole alkaloid extracted from leguminous plants, exerts anti-inflammatory, antioxidant, and neuroprotective effects by modulating multiple signaling pathways, including PI3K/Akt/mTOR and p38/JNK. Hypaphorine is frequently investigated in studies related to neurodegenerative diseases and metabolic disorders[1-2]. Additionally, Hypaphorine has been shown to effectively prevent osteoporosis[3], and exhibits antiviral activity against Dengue virus[4].
In vitro, pretreatment of human microvascular endothelial cells (HMEC-1) with Hypaphorine (0–100μM) for 6 hours, followed by lipopolysaccharide (LPS, 500ng/mL) stimulation for 48 hours, significantly suppressed LPS-induced expression of pro-inflammatory cytokines (TNF-α, IL-1β, MCP-1, VCAM-1). Hypaphorine also reversed LPS-induced upregulation of TLR4 protein and mRNA levels and downregulation of PPAR-γ. Furthermore, it blocked LPS-activated PI3K/Akt/mTOR signaling[5]. In RAW 264.7 macrophages, Hypaphorine (12.5–50μM) pretreatment for 1 hour, followed by LPS (1μg/mL) stimulation for 24 hours, markedly inhibited LPS-induced pro-inflammatory cytokine (TNF-α, IL-1β, IL-6, IL-10, MCP-1) expression and NO/PGE₂ release, while downregulating COX-2 and iNOS protein expression. Hypaphorine also suppressed LPS-induced phosphorylation of ERK, IκBα, IKKβ, and NF-κB, and inhibited NF-κB nuclear translocation[6].
In vivo, Hypaphorine (10mg/kg; intraperitoneal injection) administered 2 hours after LPS (20mg/kg) significantly attenuated LPS-induced acute lung injury (ALI) in male Sprague-Dawley (SD) rats. Hypaphorine reduced lung histopathological damage, decreased total cell counts and neutrophil proportions in bronchoalveolar lavage fluid (BALF), and lowered lung wet/dry weight ratio, microvascular permeability, and lactate dehydrogenase (LDH)/myeloperoxidase (MPO) activity. Mechanistically, Hypaphorine upregulated DUSP1 expression and inhibited p38/JNK activation, thereby suppressing pro-inflammatory cytokines (TNF-α, IL-6, IL-1β, IL-18) [7]. Hypaphorine (10mg/kg; intraperitoneal injection) was found to selectively inhibit acetylcholinesterase (AChE) activity across all brain regions (cortex, cerebellum, striatum, hippocampus) in normal rat after 24 hours, with the D-enantiomer demonstrating potent inhibition in key brain areas[8].
References:
[1] Qin P, Li Y, Su Y, et al. Bifidobacterium adolescentis-derived hypaphorine alleviates acetaminophen hepatotoxicity by promoting hepatic Cry1 expression. J Transl Med. 2024 May 31;22(1):525.
[2] Chen H, Guo T, Wang D, et al. Vaccaria hypaphorine impairs RANKL-induced osteoclastogenesis by inhibition of ERK, p38, JNK and NF-κB pathway and prevents inflammatory bone loss in mice. Biomed Pharmacother. 2018 Jan;97:1155-1163.
[3] Zhang T, Yan Y, Xue Y, et al. Pharmacokinetic Study of Hypaphorine, a Potential Agent for Treating Osteoclast-based Bone Loss, on Rats Using LC-MS/MS. Comb Chem High Throughput Screen. 2022;25(11):1889-1896.
[4] Bai S, Liang H, Jiang W, et al. Identifying hypaphorine as a novel antiviral compound against dengue virus. Antiviral Res. 2025 Jun 24;240:106220.
[5] Sun H, Zhu X, Cai W, et al. Hypaphorine Attenuates Lipopolysaccharide-Induced Endothelial Inflammation via Regulation of TLR4 and PPAR-γ Dependent on PI3K/Akt/mTOR Signal Pathway. Int J Mol Sci. 2017 Apr 17;18(4):844.
[6] Sun H, Cai W, Wang X, et al. Vaccaria hypaphorine alleviates lipopolysaccharide-induced inflammation via inactivation of NFκB and ERK pathways in Raw 264.7 cells. BMC Complement Altern Med. 2017 Feb 20;17(1):120.
[7] Ding YH, Miao RX, Zhang Q. Hypaphorine exerts anti-inflammatory effects in sepsis induced acute lung injury via modulating DUSP1/p38/JNK pathway. Kaohsiung J Med Sci. 2021 Oct;37(10):883-893.
[8] Yonekawa MKA, Penteado BB, Dal'Ongaro Rodrigues A, et al. l-Hypaphorine and d-hypaphorine: Specific antiacetylcholinesterase activity in rat brain tissue. Bioorg Med Chem Lett. 2021 Sep 1;47:128206.
| Cell experiment [1]: | |
Cell lines | Human microvascular endothelial cells (HMEC-1) |
Preparation Method | HMEC-1 cells were seeded into 6-well plates at a density of 5×10⁴ cells per well and cultured until 80% confluence. Cells were pretreated with Hypaphorine (0, 25, 50, or 100μM) for 6 hours, followed by lipopolysaccharide (LPS, 500ng/mL) stimulation for an additional 48 hours to establish the endothelial inflammation model. |
Reaction Conditions | Hypaphorine (0–100μM); 6-hour pretreatment+48-hour LPS stimulation. |
Applications | Hypaphorine downregulated pro-inflammatory cytokines (TNF-α, IL-1β, MCP-1, VCAM-1) at both mRNA and protein levels, inhibited PI3K/Akt/mTOR pathway activation, and blocked NF-κB nuclear translocation and ERK phosphorylation. |
| Animal experiment [2]: | |
Animal models | Sprague-Dawley rats |
Preparation Method | Lipopolysaccharide (LPS, 20mg/kg) was administered intratracheally to induce sepsis-associated acute lung injury (ALI). Hypaphorine (10mg/kg) was injected intraperitoneally 2 hours post-LPS. Control groups received saline or LPS alone. Rats were sacrificed after 24 hours for tissue and fluid collection. |
Dosage form | 10mg/kg; i.p. |
Applications | Hypaphorine exerted anti-inflammatory and anti-apoptotic effects by upregulating DUSP1 to inactivate the p38/JNK pathway, thereby mitigating LPS-induced ALI in rats. |
References: | |
| Cas No. | 487-58-1 | SDF | |
| المرادفات | L-Hypaphorine, (+)-Tryptophan, Tryptophan Betaine | ||
| Canonical SMILES | C[N+](C)(C(C([O-])=O)CC1=CNC2=C1C=CC=C2)C | ||
| Formula | C14H18N2O2 | M.Wt | 246.3 |
| الذوبان | H2O : 100 mg/mL (406.01 mM; Need ultrasonic); DMSO : < 1 mg/mL (insoluble or slightly soluble) | Storage | Store at -20°C,protect from light |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 4.0601 mL | 20.3004 mL | 40.6009 mL |
| 5 mM | 812 μL | 4.0601 mL | 8.1202 mL |
| 10 mM | 406 μL | 2.03 mL | 4.0601 mL |
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.
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Note: 1. Please make sure the liquid is clear before adding the next solvent.
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Quality Control & SDS
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- Purity: >99.50% Appearance: A solid
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Average Rating: 5 (Based on Reviews and 23 reference(s) in Google Scholar.)