Malabaricone B
(Synonyms: NSC 287967, NSC 630196) 目录号 : GC46031A diarylnonanoid with diverse biological activities
Cas No.:63335-24-0
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
Malabaricone B is a diarylnonanoid that has been found in Myristica and has diverse biological activities, including enzyme inhibitory, antimicrobial, anticancer, and antioxidant properties.1,2,3,4,5 It is an inhibitor of sphingomyelin synthase 1 and -2 (IC50s = 3.5 and 2.5 μM, respectively, in fibroblast cell lysates).1 It is active against the bacteria S. aureus, B. subtilis, and S. durans (MIC = 1 μg/ml for all) and three strains of the fungus C. albicans (MICs = 4-16 μg/ml).2 It is cytotoxic to A549, A375, Jurkat, A431, U937, and MCF-7 cells (IC50s = 8.1, 26.7, 27.4, 9.5, 27.5, and 9.3 μM, respectively) but not non-cancerous INT407, HEK293, or WI-38 cells.3 It increases the levels of intracellular reactive oxygen species (ROS) and induces apoptosis in A549 cells. It reduces the formation of thiobarbituric acid reactive substrates (TBARS) by 28.2% in rat liver mitochondria when used at a concentration of 2 μg/ml but scavenges only 5% of 2,2-diphenyl-picrylhydrazyl radicals at 7 μg/ml.4 Malabaricone B (10, 15, and 20 mg/kg) reduces stomach ulceration in a mouse model of indomethacin-induced gastric ulcer.5
|1. Othman, M.A., Yuyama, K., Murai, Y., et al. Malabaricone C as natural sphingomyelin synthase inhibitor against diet-induced obesity and its lipid metabolism in mice. Med. Chem. Lett. 10(8), 1154-1158 (2019).|2. Orabi, K.Y., Mossa, J.S., and El-Feraly, F.S. Isolation and characterization of two antimicrobial agents from mace (Myristica fragrans). J. Nat. Prod. 54(3), 856-859 (1991).|3. Tyagi, M., Maity, B., Saha, B., et al. Spice-derived phenolic, malabaricone B induces mitochondrial damage in lung cancer cells via a p53-independent pathway. Food Funct. 9(11), 5715-5727 (2018).|4. Patro, B.S., Bauri, A.K., Mishra, S., et al. Antioxidant activity of Myristica malabarica extracts and their constituents. J. Agric. Food Chem. 53(17), 6912-6918 (2005).|5. Banerjee, D., Bauri, A.K., Guha, R.K., et al. Healing properties of malabaricone B and malabaricone C, against indomethacin-induced gastric uleration and mechanism of action. Eur. J. Pharm. 578(2-3), 300-312 (2008).
| Cas No. | 63335-24-0 | SDF | |
| 别名 | NSC 287967, NSC 630196 | ||
| Canonical SMILES | OC1=C(C(CCCCCCCCC2=CC=C(O)C=C2)=O)C(O)=CC=C1 | ||
| 分子式 | C21H26O4 | 分子量 | 342.4 |
| 溶解度 | DMF: 25 mg/ml,DMSO: 20 mg/ml,Ethanol: 10 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 | 2.9206 mL | 14.6028 mL | 29.2056 mL |
| 5 mM | 0.5841 mL | 2.9206 mL | 5.8411 mL |
| 10 mM | 0.2921 mL | 1.4603 mL | 2.9206 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。
Healing properties of Malabaricone B and malabaricone C, against indomethacin-induced gastric ulceration and mechanism of action
Eur J Pharmacol 2008 Jan 14;578(2-3):300-12.PMID:17977527DOI:10.1016/j.ejphar.2007.09.041.
The healing activity of Malabaricone B and malabaricone C, the major antioxidant constituents of the spice Myristica malabarica against the indomethacin-induced gastric ulceration in mice has been studied. The histological indices revealed maximum ulceration on the 3rd day after indomethacin administration, which was effectively healed by Malabaricone B, malabaricone C (each 10 mg/kg body weight/day) and omeprazole (3 mg/kg body weight/day) for 3 days. Compared to the untreated ulcerated mice, treatment with Malabaricone B, malabaricone C and omeprazole reduced the ulcer indices by 60.3% (P<0.01), 88.4% and 86.1% respectively (P<0.001). All the test samples accelerated ulcer healing than observed in natural recovery even after 7 days. Stomach ulceration reduced the total antioxidant status of plasma by 41% (P<0.05), which was significantly increased by Malabaricone B (36%, P<0.01), malabaricone C (61%, P<0.001) and omeprazole (53%, P<0.001). Compared to the ulcerated untreated mice, those treated with Malabaricone B reduced the levels of thiobarbituric acid reactive substances and protein carbonyls by 17% and approximately 34% respectively (P<0.05), while malabaricone C and omeprazole reduced the parameters almost equally (approximately 30%, P<0.01, and approximately 40%, P<0.01 respectively). Likewise, all the test samples reduced the oxidation of protein and non-protein thiols significantly (P<0.05). The antioxidant activity of the test samples could partly account their healing capacities. However, the differential potency of them was explainable by considering their relative abilities to modulate mucin secretion, PGE(2) synthesis and expression of EGF receptor and COX isoforms, malabaricone C being most effective in controlling all these factors.
Spice-derived phenolic, Malabaricone B induces mitochondrial damage in lung cancer cells via a p53-independent pathway
Food Funct 2018 Nov 14;9(11):5715-5727.PMID:30318526DOI:10.1039/c8fo00624e.
The spice-derived phenolic, Malabaricone B (mal B) showed selective toxicity to human lung cancer (A549), malignant melanoma (A375) and T cell leukemia (Jurkat) cell lines, without showing toxicity to human normal intestinal (INT407), human kidney (HEK293) and lung fibroblast (WI-38) cells. Among the chosen cancer cell lines, mal B showed maximum cytotoxicity to the A549 cells (IC50 = 8.1 ± 1.0 μM), which was significantly better than that of curcumin (IC50 = 26.7 ± 3.1 μM). Further morphological studies by phase contrast microscopy and a clonogenic assay of the A549 cells revealed that mal B treatment increased the number of shrinking cells and also abolished the clonal proliferation of the cells. Mal B induced apoptotic cell death was confirmed by DNA laddering and quantified by cytoplasmic oligonucleosome formation and annexin V/PI assays. The mal B-induced apoptosis was mediated by an increase in the intracellular reactive oxygen species (ROS), because the cell-permeable antioxidants, N-acetylcysteine (NAC) and PEG-SOD, strongly inhibited its cytotoxicity to the A549 cells. Mal B increased the BAX level while simultaneously decreasing the BCL-2 and BCL-XL levels in the A549 cells, triggering the mitochondrial apoptotic pathway as revealed from the release of cytochrome c, and the activation of caspase-9 and caspase-3. Pre-treatment of cells with caspase-9, caspase-3 and pan-caspase inhibitors made them more resistant to mal B treatment. This effect of mal B was strongly associated with the concomitant decrease in anti-apoptotic (IAP1, IAP2 and survivin), angiogenic (growth factors) and cancer invasiveness (matrix metalloproteinase-9, COX-2) modulating proteins. Mal B induced cytotoxicity was unaffected by the shRNA-mediated depletion of p53 in A549 cells. Most importantly, mal B sensitized a wide range of human carcinoma cells regardless of their p53 status. Finally, mal B (100 mg kg-1) also inhibited lung tumor (xenograft) growth in SCID mice.
Angiogenic and cell proliferating action of the natural diarylnonanoids, Malabaricone B and malabaricone C during healing of indomethacin-induced gastric ulceration
Pharm Res 2008 Jul;25(7):1601-9.PMID:18071876DOI:10.1007/s11095-007-9512-0.
Purpose: To evaluate the plant phenolics, Malabaricone B (mal B) and malabaricone C (mal C) in healing stomach ulcer by modulating angiogenesis. Materials and methods: Male Swiss albino mice, ulcerated with indomethacin (18 mg/kg, p. o., single dose) were treated up to 7 days with different doses of mal B or mal C. The healing capacities of the drugs and their effects on the angiogenic parameters were assessed. Results: Maximum ulceration, observed on the 3rd day after indomethacin administration was effectively healed by mal B and mal C (each 10 mg/kg, p. o. x 3 days), the latter showing equivalent potency (~78% p < 0.001) as that of Omez (3 mg/kg, p. o. x 3 days) and misoprostol (10 mug/kg, p. o. x 3 days). Compared to the untreated mice, those treated with mal B or mal C respectively for 3 days increased the mucosal EGF level (139 and 178%, p < 0.001), the serum VEGF level (56%, p < 0.01 and 95%, p < 0.001) and microvessels formation (37%, p < 0.05 and 62%, p < 0.01), while reducing the serum endostatin level (37%, p < 0.05 and 61%, p < 0.01). The relative healing capacities of mal B and mal C correlated well with their respective abilities to modulate the angiogenic factors. The healing by Omez and misoprostol was not due to improved angiogenesis. Conclusions: The drugs, mal B and mal C could effectively heal indomethacin-induced stomach ulceration in mice by promoting angiogenesis.
Regulation of arginase/nitric oxide synthesis axis via cytokine balance contributes to the healing action of Malabaricone B against indomethacin-induced gastric ulceration in mice
Int Immunopharmacol 2009 Apr;9(4):491-8.PMID:19291837DOI:10.1016/j.intimp.2009.01.028.
The role of the arginine-metabolism in the healing action of the Myristica malabarica phenol Malabaricone B (mal B) and omeprazole against indomethacin-induced stomach ulceration in mouse was investigated. Indomethacin (18 mg kg- 1) was found to induce maximum stomach ulceration in Swiss albino mice on the 3rd day of its administration, which was associated with reduced arginase activity (30.8%, P < 0.01), eNOS expression, along with increased iNOS expression, total NOS activity (5.55 folds, P < 0.001), NO generation (2.19 folds, P < 0.001), and ratio of pro-/anti-inflammatory cytokines. Besides providing comparable healing as omeprazole (3 mg kg- 1 x 3 days), mal B (10 mg kg- 1 x 3 days, p. o.) shifted the iNOS/NO axis to the arginase/polyamine axis as revealed from the increased arginase activity (51.6%, P < 0.001), eNOS expression, and reduced iNOS expression, total NOS activity (approximately 75%, P < 0.001), and NO level (50.6%, P < 0.01). These could be attributed to a favourable anti/pro inflammatory cytokines ratio, generated by mal B. The healing by omeprazole was however, not significantly associated with those parameters.
Isolation and characterization of two antimicrobial agents from mace (Myristica fragrans)
J Nat Prod 1991 May-Jun;54(3):856-9.PMID:1955885DOI:10.1021/np50075a017.
The two antimicrobial resorcinols Malabaricone B [1] and malabaricone C [2] were isolated from mace, the dried seed covers of Myristica fragrans. Both compounds exhibited strong antifungal and antibacterial activities. Structure modifications by methylation or reduction resulted in diminished activity.