Girinimbine
(Synonyms: 吉九里香碱,Girinimbin) 目录号 : GC62988
Girinimbine (Girinimbin) 是一种咔唑类生物碱，具有多种生物学作用。Girinimbine 可诱导细胞凋亡 (apoptosis)，具有抗锥虫、抗血小板活性、抗菌活性、抗炎、抗氧化和抗肿瘤活性。
Cas No.:23095-44-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Girinimbine (Girinimbin) is a carbazole alkaloid with a variety of biological effects. Girinimbine can induce apoptosis, and has antitrypanosomal, antiplatelet activity, antibacterial activity, anti-inflammatory, antioxidant and antitumor activities[1][2][3].
Girinimbine (1-400 µM; 24-72 h) decreases the viability of HepG2 cells in 24, 48 and 72 h with IC50 values of 61 µM, 56 µM, and 40 µM respectively. Girinimbine (10-100 µM; 24-48 h) increase of LDH leakage in both concentration- and time-dependent manner in HepG2 cells[1].Girinimbine (56 µM; 24-48 h) treatment results in DNA fragmentation and elevates levels of caspase-3 in HepG2 cells[1].HepG2 cells[1].Girinimbine (56 µM; 12-48 h) treatment also displays a time-dependent accumulation of the Sub-G0/G1 peak (hypodiploid) and caused G0/G1-phase arrest[1].Girinimbine shows a potent antitrypanosomal activitywith an IC50 value of 10.16 µg/mL[3].
Girinimbine (10-100 mg/kg; orally gavage; once) pretreatment helps limit total leukocyte migration, and reduced pro-inflammatory cytokine (IL-1β, TNF-α) levels in the peritoneal fluid[2]. In vivo in zebrafish embryos, Girinimbine (20 μg/mL; 24 hours) shows significant distribution of apoptotic cells in embryos[2].
[1]. Suvitha Syam, et al. The growth suppressing effects of girinimbine on HepG2 involve induction of apoptosis and cell cycle arrest. Molecules. 2011 Aug 23;16(8):7155-70.
[2]. Venoos Iman, et al. Anticancer and anti-inflammatory activities of girinimbine isolated from Murraya koenigii. Drug Des Devel Ther. 2016 Dec 28;11:103-121.
[3]. H O Dyary, et al. Antitrypanosomal and cytotoxic activities of botanical extracts from Murraya koenigii (L.) and Alpinia mutica Roxb. Trop Biomed. 2019 Mar 1;36(1):94-102.
| Cas No. | 23095-44-5 | SDF | |
| 别名 | 吉九里香碱,Girinimbin | ||
| 分子式 | C18H17NO | 分子量 | 263.33 |
| 溶解度 | 储存条件 | Store at 2-8°C,protect from light | |
| 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 | 3.7975 mL | 18.9876 mL | 37.9752 mL |
| 5 mM | 0.7595 mL | 3.7975 mL | 7.595 mL |
| 10 mM | 0.3798 mL | 1.8988 mL | 3.7975 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。
Pleiotropic Effect of Mahanine and Girinimbine Analogs: Anticancer Mechanism and its Therapeutic Versatility
Anticancer Agents Med Chem 2018;18(14):1983-1990.PMID:30173653DOI:10.2174/1871520618666180830151720.
Emerging evidence present credible support in favour of the potential role of mahanine and Girinimbine. Non-toxic herbal carbazole alkaloids occur in the edible part of Murraya koenigii, Micromelum minutum, M. zeylanicum, and M. euchrestiolia. Mahanine and Girinimbine are the major potent compounds from these species. In fact, they interfered with tumour expansion and metastasis development through down-regulation of apoptotic and antiapoptotic protein, also involved in the stimulation of cell cycle arrest. Consequently, these compounds were well proven for the in-vitro and in vivo evaluation that could be developed as novel agents either alone or as an adjuvant to conventional therapeutics. Therefore, mahanine and Girinimbine analogs have the potential to be the promising chemopreventive agents for the tumour recurrence and the treatment of human malignancies. In this review, an updated wide-range of pleiotropic anticancer and biological effects induction by mahanine and Girinimbine against cancer cells were deeply summarized.
Retracted: Girinimbine Inhibits the Proliferation of Human Ovarian Cancer Cells In Vitro via the Phosphatidylinositol-3-Kinase (PI3K)/Akt and the Mammalian Target of Rapamycin (mTOR) and Wnt/β-Catenin Signaling Pathways
Med Sci Monit 2021 Mar 11;27:e931225.PMID:33704262DOI:10.12659/MSM.931225.
This paper is retracted at the author's request. Reference: Qiu Xin, An Muer: Girinimbine Inhibits the Proliferation of Human Ovarian Cancer Cells In Vitro via the Phosphatidylinositol-3-Kinase (PI3K)/Akt and the Mammalian Target of Rapamycin (mTOR) and Wnt/ß-Catenin Signaling Pathways. Med Sci Monit 2018; 24: 5480-5487. 10.12659/MSM.910137.
Girinimbine from curry leaves promotes gastro protection against ethanol induced peptic ulcers and improves healing via regulation of anti-inflammatory and antioxidant mechanisms
Food Funct 2020 Apr 30;11(4):3493-3505.PMID:32248216DOI:10.1039/d0fo00053a.
Curry leaves (Murraya koenigii) are a leafy spice used in Indian cookery for its fragrant aroma. Many bioactive functional compounds have been identified, and among them carbazole alkaloids have attracted wide attention due to their multi-dimensional medicinal value. Even though it has been established that the carbazole alkaloid is responsible for the anti-ulcer effect showed by this culinary herb, there is no further evidence to say which phytochemical is responsible for this. In the present study, we investigated the gastro-protective effects and mechanism of Girinimbine, a major carbazole alkaloid present in curry leaves. Rats were administered with ethanol to produce gastric ulcers, and the prophylactic effect of Girinimbine was evaluated. A macroscopic and histological examination was carried out to examine the lesions. Furthermore, the mucus production, NO production, PGE2 synthesis, mucosal nonprotein sulphydryls, glutathione (GSH) level, lipid peroxidation (MDA) level and COX inhibition were assessed. In addition, in particular, TNF-α and IL-6, two important cytokines, were evaluated. Immunohistochemical and gene expression studies were conducted to determine the HSP70 and iNOS biomarkers. Our results indicated that Girinimbine significantly reduced the ulcer index and totally safeguarded the mucosa from lesions. The protective effect of Girinimbine was complemented through the restoration of the reduced GSH and NP-SH level. This was associated with a reduction of MDA, which was elevated by the administration of ethanol. Pre-treatment of the ethanol induced ulcer with Girinimbine reduced the NO concentration in the plasma and elevated PGE2 together with a decreased level of TNF-α and IL-6. Girinimbine had shown suppressing effects on COX-2 enzymes, but not on COX-1. In addition, significantly upregulated HSP70 and downregulated iNOS were observed in Girinimbine treated rat tissue at both the transcriptional and translational level. Our results clearly indicated that Girinimbine displayed a significant gastro-protection effect, via the capacity to inhibit inflammatory responses and antioxidant potential.
Naturally occurring Girinimbine alkaloid inhibits the proliferation, migration, and invasion of human breast cancer cells via induction of apoptosis and inhibition of MEK/ERK and STAT3 signalling pathways
Acta Biochim Pol 2021 Sep 2;68(4):647-652.PMID:34472799DOI:10.18388/abp.2020_5531.
The currently used anticancer drugs against breast cancer possess serious side effects, have limited efficacy, and often lead to recurrence of the malignancy. The main aim of this research was to investigate the anticancer potential of Girinimbine, a naturally occurring carbazole alkaloid, against ER-negative breast cancer cells (MDA-MB-453) along with its effects on cell migration and invasion, apoptosis, and MEK/ERK/STAT3 pathway. MTT assay was used to evaluate antiproliferative effects of Girinimbine while a clonogenic assay was used to study cell colony formation. Transwell migration and invasion assays were involved to study its effects on cell migration and invasion. Fluorescence microscopy using acridine orange/ethidium bromide was used to study apoptotic effects of Girinimbine which was quantified by annexin v-FITC assay. Effects of Girinimbine on MEK/ERK and STAT3 signalling pathways were evaluated by western blot assay. Results showed that Girinimbine exhibited dose-dependent as well as time-dependent antiproliferative effects in MDA-MB-453 cells along with strongly inhibiting the cell colony potency of these cancerous cells. Girinimbine can inhibit both cancer cell migration as well as invasion. Girinimbine has induced potent chromatin condensation and nuclear fragmentation. The percentage of both early and late apoptotic cells increased significantly after Girinimbine exposure. The anticancer effects of Girinimbine were shown to be mediated via inhibition of the MEK/ERK as well as STAT3 signalling pathways. In conclusion, it may be proposed that Girinimbine could be a promising anticancer agent against breast cancer, provided further in-depth studies are carried out.
Anticancer and anti-inflammatory activities of Girinimbine isolated from Murraya koenigii
Drug Des Devel Ther 2016 Dec 28;11:103-121.PMID:28096658DOI:10.2147/DDDT.S115135.
Therapy that directly targets apoptosis and/or inflammation could be highly effective for the treatment of cancer. Murraya koenigii is an edible herb that has been traditionally used for cancer treatment as well as inflammation. Here, we describe that Girinimbine, a carbazole alkaloid isolated from M. koenigii, induced apoptosis and inhibited inflammation in vitro as well as in vivo. Induction of apoptosis in human colon cancer cells (HT-29) by Girinimbine revealed decreased cell viability in HT-29, whereas there was no cytotoxic effect on normal colon cells. Changes in mitochondrial membrane potential, nuclear condensation, cell permeability, and cytochrome c translocation in girinimbine-treated HT-29 cells demonstrated involvement of mitochondria in apoptosis. Early-phase apoptosis was shown in both acridine orange/propidium iodide and annexin V results. Girinimbine treatment also resulted in an induction of G0/G1 phase arrest which was further corroborated with the upregulation of two cyclin-dependent kinase proteins, p21 and p27. Girinimbine treatment activated apoptosis through the intrinsic pathway by activation of caspases 3 and 9 as well as cleaved caspases 3 and 9 which ended by triggering the execution pathway. Moreover, apoptosis was confirmed by downregulation of Bcl-2 and upregulation of Bax in girinimbine-treated cells. In addition, the key tumor suppressor protein, p53, was seen to be considerably upregulated upon Girinimbine treatment. Induction of apoptosis by Girinimbine was also evidenced in vivo in zebrafish embryos, with results demonstrating significant distribution of apoptotic cells in embryos after a 24-hour treatment period. Meanwhile, anti-inflammatory action was evidenced by the significant dose-dependent Girinimbine inhibition of nitric oxide production in lipopolysaccharide/interferon-gamma-induced cells along with significant inhibition of nuclear factor-kappa B translocation from the cytoplasm to nucleus in stimulated RAW 264.7 cells. Girinimbine was also shown to have considerable antioxidant activity whereby 20 μg/mL of Girinimbine was equivalent to 82.17±1.88 μM of Trolox. In mice with carrageenan-induced peritonitis, oral pretreatment with Girinimbine helped limit total leukocyte migration (mainly of neutrophils), and reduced pro-inflammatory cytokine levels (interleukin-1beta and tumor necrosis factor-alpha) in the peritoneal fluid. These findings strongly suggest that Girinimbine could act as a chemopreventive and/or chemotherapeutic agent by inducing apoptosis while suppressing inflammation. There is a potential for Girinimbine to be further investigated for its applicability in treating early stages of cancer.