Hecogenin
(Synonyms: 海柯吉宁; (+)-Hecogenin; NSC 115921) 目录号 : GC38428
A steroid sapogenin with diverse biological activities
Cas No.:467-55-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Hecogenin is a natural steroid sapogenin with diverse biological activities that was originally isolated from A. sisalana and has been used in the synthesis of steroids.1 It has antioxidant, anti-inflammatory, antiproliferative, and neuroprotective properties.2,3,4,5 Hecogenin (10 μM) decreases superoxide anion formation induced by N-Formyl-Met-Leu-Phe in rat neutrophils by 23.6%.2 It also inhibits myeloperoxidase (MPO) release from human neutrophils activated by phorbol 12-myristate 13-acetate when used at a concentration of 1 μg/ml.3 Hecogenin inhibits proliferation of the breast cancer cell lines MDA-MB-231, MDA-MB-468, MCF-10A, MCF-7, T47D, BT474, and SK-BR-3 (IC50s = 28.7-38.2 μM).4 It decreases the number of glutamate-induced TUNEL-positive primary rat spinal motor neurons by 11% when used at a concentration of 1 μM.5 In vivo, hecogenin (15 mg/kg) decreases the mucosal lesion area of ethanol-induced gastric ulceration in mice.3 It also decreases tumor volume in an MDA-MB-231 human breast cancer mouse xenograft model when administered at a dose of 10 mg/kg three times per week.4
1.Cripps, A.L., and Blunden, G.A quantitative gas-liquid chromatographic method for the estimation of hecogenin and tigogenin in the leaves, juice and sapogenin concentrates of Agave sisalanaSteroids31(5)661-669(1978) 2.Tsai, P.L., Wang, J.P., Chang, C.W., et al.Constituents and bioactive principles of Polygonum chinensisPhytochemistry49(6)1663-1666(1998) 3.Santos Cerqueira, G., dos Santos e Silva, G., Rios Vasconcelos, E., et al.Effects of hecogenin and its possible mechanism of action on experimental models of gastric ulcer in miceEur. J. Pharmacol.683(1-3)260-269(2012) 4.Elsayed, H.E., Ebrahim, H.Y., Haggag, E.G., et al.Rationally designed hecogenin thiosemicarbazone analogs as novel MEK inhibitors for the control of breast malignanciesBioorg. Med. Chem.25(24)6297-6312(2017) 5.Vincent, A.M., Backus, C., Taubman, A.A., et al.Identification of candidate drugs for the treatment of ALSAmyotroph. Lateral Scler. Other Motor Neuron Disord.6(1)29-36(2005)
| Cas No. | 467-55-0 | SDF | |
| 别名 | 海柯吉宁; (+)-Hecogenin; NSC 115921 | ||
| Canonical SMILES | [H][C@]1(O[C@@]2(OC[C@H](C)CC2)[C@@H](C)[C@@]1([C@]34C)[H])C[C@@]3([H])[C@]5([H])CC[C@@]6([H])C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC4=O | ||
| 分子式 | C27H42O4 | 分子量 | 430.62 |
| 溶解度 | DMF: 30 mg/ml, 0.8mg/ml in DMSO (ultrasonic and warming and heat), Ethanol: 30 mg/ml, Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.3222 mL | 11.6112 mL | 23.2223 mL |
| 5 mM | 0.4644 mL | 2.3222 mL | 4.6445 mL |
| 10 mM | 0.2322 mL | 1.1611 mL | 2.3222 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Hecogenin and its derivates: A pharmacology review
Biomed Pharmacother 2023 Mar;159:114251.PMID:36641922DOI:10.1016/j.biopha.2023.114251.
Despite the several uses of drugs from natural compounds in the pharmaceutical industry, new molecules have been discovered and associated with pharmacological activities over the years. Hecogenin, a steroidal saponin, has been the subject of several studies due to reports of pharmacological activities. This study combines the articles published to date that show the pharmacological activity and the mechanism of action of Hecogenin, its acetate, and its derivates. This compilation shows that the compounds can act in different pathologies that affect many systems of the human body. They showed pharmacological properties in inflammation, mediating cytokines, cells, and environment. Also, it participated in tumoral processes by pathways like PPGARγ, ERK½, and MMP-2 and showed antimicrobial effects against organisms like Candida and Aedes aegypti's larvae. This review indicates that continuing studies with these molecules are essential once they have the potential to be a future drug.
Effect of Hecogenin on DNA instability
Toxicol Rep 2016 Jun 16;3:539-543.PMID:28959577DOI:10.1016/j.toxrep.2016.06.004.
Hecogenin is a sapogenin found in Agave species in high quantities and is responsible for the many therapeutic effects of these medicinal plants. In addition, this compound is also widely used in the pharmaceutical industry as a precursor for the synthesis of steroidal hormones and anti-inflammatory drugs. Despite Hecogenin being widely used, little is known about its toxicological properties. Therefore, the present study aimed to investigate the cytotoxic, genotoxic and mutagenic effects of Hecogenin on HepG2 cells. Cytotoxicity was analyzed using the MTT test. Then, genotoxic and mutagenic potentials were assessed by comet assay and cytokinesis-block micronucleus assay, respectively. Cytotoxic effect was observed only when cells were exposed to concentrations of Hecogenin equal or higher than 100 μM. Although a lower concentration of Hecogenin caused DNA damage, a reduction on nuclear mutagenic markers in HepG2 cells was observed. The results indicated that Hecogenin treatment generated DNA damage, but in fact it would be repaired, avoiding dissemination of the damage throughout the cell division. Further studies need to be performed to confirm the observed protective effect of Hecogenin against genomic instability.
Hecogenin exhibits anti-arthritic activity in rats through suppression of pro-inflammatory cytokines in Complete Freund's adjuvant-induced arthritis
Immunopharmacol Immunotoxicol 2018 Feb;40(1):59-71.PMID:29192804DOI:10.1080/08923973.2017.1405439.
Hecogenin is a steroidal sapogenin isolated from the leaves of Agave genus species that plays an important role in the treatment of a variety of inflammatory diseases. The aim of the present study was to evaluate the anti-arthritic activity of Hecogenin in Complete Freund's adjuvant-induced arthritis in rats. The Hecogenin (40 µl of 50 µg/kg, orally) and Hecogenin + fluticasone (40 µl of 25 µg/kg, each, orally) was tested against Complete Freund's adjuvant-induced arthritis in rats by evaluating various parameters such as paw volume, arthritic score, joint diameter, spleen weight, thymus weight, haematological and biochemical parameters and pro-inflammatory cytokines. Histopathological and radiological analyzes of ankle joints were also carried out. Treatment of rats with Hecogenin and its combination elicited significant reduction in paw edema, arthritic score and joint diameter. Hecogenin and its combination also inhibited joint destruction in histopathological and radiological analyzes of ankle joint. Hecogenin and its combination significantly increased the levels of red blood cells and hemoglobin but decreased the white blood cell count. The anti-arthritic activity was also confirmed with the change in biochemical parameters and myeloperoxidase assay. In the present investigation, Hecogenin and its combination prevent destruction of cartilage and protect synovial membrane with improving health status through haematonic properties and down regulation of various cytokines. Hence, Hecogenin may be a potential therapeutic candidate for the treatment of rheumatoid arthritis.
Hecogenin and fluticasone combination attenuates TNBS-induced ulcerative colitis in rats via downregulation of pro-inflammatory mediators and oxidative stress
Immunopharmacol Immunotoxicol 2021 Apr;43(2):160-170.PMID:33435764DOI:10.1080/08923973.2021.1872617.
Objective: Ulcerative colitis is common types of severe, progressive, idiopathic inflammatory bowel disease that involves the mucosal lining of the large intestine. The purpose of the study is to explore the effects of Hecogenin in TNBS (2, 4, 6- trinitrobenzene sulfonic acid) induced ulcerative colitis model in rats. Material and methods: Thirty Wistar rats were randomized into five groups: (i) Normal Control (NC), (ii) Disease Control (DC), (iii) Hecogenin (HG) (50 µg/rat), (iv) Fluticasone (FC) (50 µg/rat), (v) Hecogenin + Fluticasone (HG + FC) combination (25 µg/rat). Colitis was induced by trans-rectal administration of TNBS using a catheter inserted 8 cm into the rectal portion of the rat. Colitis was evaluated by an independent observer who was blinded to the treatment. All treatment group results were compared to the TNBS group results. Results: The study results revealed that treatment of rats with HG and HG + FC significantly improved the body weight and colon length whereas; decreased the spleen weight, colon weight/length ratio, macroscopic lesions score, diarrhea score and adhesion score. The drug treatment in rats substantially decreased the development of inflammatory cytokines, levels of serum immunoglobulin E, colonic nitric oxide contents and restoration of antioxidant stress markers. Histopathological colon sample study significantly reduced colonic inflammation with a substantial decrease in inflammation score. Conclusion: Thus, HG and HG + FC combination could change the pathogenesis of the disease and may be a potential therapeutic target for the treatment of ulcerative colitis by a reduction in dose in conjunction with FC to prevent the persistent adverse effects associated with FC.
Anti-inflammatory potential of Hecogenin on atopic dermatitis and airway hyper-responsiveness by regulation of pro-inflammatory cytokines
Immunopharmacol Immunotoxicol 2019 Apr;41(2):327-336.PMID:31039648DOI:10.1080/08923973.2019.1608445.
Objective: Hecogenin is a sapogenin found in Agave sisalana species that is used extensively for the treatment of anti-inflammatory, antifungal, hypotensive, anti-nociceptive activity and cancer. We have studied the anti-inflammatory effect of Hecogenin and its combination with Fluticasone on atopic dermatitis and airway hyper-responsiveness in Balb/c mice. Material and methods: Dermatitis was induced by repeated application of 2, 4-dinitrofluorobenzene in Balb/c mice. After a topical application of Hecogenin, Fluticasone and their combination on the skin lesions, the ear thickness, ear weight and erythema score were evaluated. Asthma was induced by sensitization and challenge of ovalbumin in Balb/c mice. Results: The topical application of Hecogenin and its combination with Fluticasone in mice effectively suppressed the ear swelling and weight. As well as the levels of pro-inflammatory cytokines were decreased by Hecogenin and its combination in-vivo. Whereas, intra-nasal administration of Hecogenin and its combination in ovalbumin induced airway hyper-responsiveness reveals a significant decrement in total cell count, differential cell count and cytokines levels. Similar observations were obtained for myeloperoxidase level in ear and lung tissue. The results were supported by histological studies of ear and lung tissue. Conclusion: These data indicate that Hecogenin has been proved as a potential therapy for allergic skin diseases and bronchial asthma treatments in combination with Fluticasone by reducing its dose from 50 to 25 μg/mice in combination to circumvent the long term side effects of Fluticasone. The beneficial effect of Hecogenin may be related to the diminution of TNF-α and IL-12 cytokines production in Balb/c mice.