Lactonic sophorolipid (1',4"-Sophorolactone 6',6"-diacetate)

目录号: GC41857纯度: >80.00%同义词: 槐糖脂
Lactonic sophorolipid由槐糖基与长链羟基脂肪酸通过内酯键构成,兼具细胞毒性效应和表面活性特性。

Lactonic sophorolipid (1',4"-Sophorolactone 6',6"-diacetate)
Cas No.: 148409-20-5
规格价格库存数量操作
100mg¥906.00现货
1
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1
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1

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产品描述 Description

Lactonic sophorolipid is made up of a sophorose moiety attached to a long chain of hydroxyl fatty acid, with cytotoxic effects and surface-active properties[1]. Lactonic sophorolipid exerts bacteriostatic and bactericidal effects by disrupting the cell wall, increasing the permeability of the cell membrane, and causing the efflux of intracellular substances[2]. Lactonic sophorolipid has been widely used to inhibit oral pathogens both in planktonic and oral biofilm states[3].

In vitro, Lactonic sophorolipid treatment for 24 hours significantly inhibited the viability of HepG2 cells, with an IC50 value of 25μg/ml[4]. Lactonic sophorolipid treatment at 6mg/ml for 4 hours significantly hindered the synthesis of the cell wall of Pseudomonas aeruginosa, resulting in a decrease in the ATP content of the bacteria and inhibition of bacterial growth[5].

In vivo, Lactonic sophorolipid treatment via oral administration at a dose of 50mg/kg (every other day for 70 days) significantly increased the number and size of intestinal polyps in Apcmin+/- mice[6].

References:
[1] Van Bogaert I N A, Saerens K, De Muynck C, et al. Microbial production and application of sophorolipids[J]. Applied microbiology and biotechnology, 2007, 76(1): 23-34.
[2] Cho W Y, Ng J F, Yap W H, et al. Sophorolipids—bio-based antimicrobial formulating agents for applications in food and health[J]. Molecules, 2022, 27(17): 5556.
[3] Elshikh M, Moya‐Ramírez I, Moens H, et al. Rhamnolipids and lactonic sophorolipids: natural antimicrobial surfactants for oral hygiene[J]. Journal of applied microbiology, 2017, 123(5): 1111-1123.
[4] Wang X, Xu N, Li Q, et al. Lactonic sophorolipid–induced apoptosis in human HepG2 cells through the Caspase-3 pathway[J]. Applied Microbiology and Biotechnology, 2021, 105(5): 2033-2042.
[5] Ma X, Wang T, Zhang H, et al. Comparison of inhibitory effects and mechanisms of lactonic sophorolipid on different pathogenic bacteria[J]. Frontiers in Microbiology, 2022, 13: 929932.
[6] Callaghan B, Lydon H, Roelants S L K W, et al. Lactonic sophorolipids increase tumor burden in Apcmin+/-mice[J]. PloS one, 2016, 11(6): e0156845.

Lactonic sophorolipid由槐糖基与长链羟基脂肪酸通过内酯键构成,兼具细胞毒性效应和表面活性特性[1]。Lactonic sophorolipid通过破坏细胞壁、增加细胞膜通透性及引发胞内物质外流,发挥抑菌和杀菌作用[2]。Lactonic sophorolipid已广泛应用于抑制浮游状态和口腔生物膜状态下的口腔致病菌生长[3]

在体外,Lactonic sophorolipid处理24小时可显著抑制HepG2细胞活力,IC50值为25μg/ml[4]。使用6mg/ml的Lactonic sophorolipid处理铜绿假单胞菌4小时,能显著阻碍细胞壁合成,导致细菌ATP含量下降并抑制细菌生长[5]

在体内,隔日口服50mg/kg剂量的Lactonic sophorolipid连续70天,可显著增加Apcmin+/-小鼠肠道息肉的数量和大小[6]

实验参考方法 Experimental Reference Method

Cell experiment [1]:

Cell lines

HepG2 cells

Preparation Method

HepG2 cells were cultured in DMEM medium supplemented with 10% fetal bovine serum (FBS), 100U/ml penicillin, and 100μg/ml streptomycin. Cells were cultured in an incubator at 37°C with 5% CO2. HepG2 cells (1×104 cells/well) were seeded in 96-well plates and cultured with Lactonic sophorolipid at different concentrations (2.5, 5, 10, 20, 40, 80, and 160μg/ml) in complete medium for 24, 48, and 72 hours. During the last 4h of incubation, MTT (5mg/ml) was added to each well, and DMSO was added to dissolve the crystals before absorbance was measured at a wavelength of 490nm.

Reaction Conditions

2.5, 5, 10, 20, 40, 80, and 160μg/ml; 24, 48, and 72h

Applications

Lactonic sophorolipid treatment inhibited the viability of HepG2 cells in a dose- and time-dependent manner.
Animal experiment [2]:

Animal models

Male Apcmin+/- mice

Preparation Method

Male Apcmin+/- mice were housed under 12/12h light/dark cycles and had ad libitum access to food and water. Every other day, mice were orally administered vehicle solution or 0.1% ethanol/10% sucrose solution containing 50mg/kg Lactonic sophorolipid (using a sterile p20 pipet tip). The whole experiment lasted for 70 days and, histopathological changes in the intestine were evaluated.

Dosage form

50mg/kg; every other day for 70 days; p.o.

Applications

Lactonic sophorolipid treatment significantly resulted in an increase in the number and size of intestinal polyps in mice.

References:
[1] Wang X, Xu N, Li Q, et al. Lactonic sophorolipid–induced apoptosis in human HepG2 cells through the Caspase-3 pathway[J]. Applied Microbiology and Biotechnology, 2021, 105(5): 2033-2042.
[2] Callaghan B, Lydon H, Roelants S L K W, et al. Lactonic sophorolipids increase tumor burden in Apcmin+/-mice[J]. PloS one, 2016, 11(6): e0156845.

产品文档 Product Documents

Purity:>80.00%

化学性质Chemical Properties

CAS 号
148409-20-5
同义词
槐糖脂
SMILES
O=C1CCCCCCC/C=C/CCCCCC[C@H](C)O[C@]2([H])O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@@]2([H])O[C@@](O[C@@H]3COC(C)=O)([H])[C@H](O)[C@@H](O)[C@]3([H])O1
分子式
C34H56O14
分子量
688.8 g/mol
溶解性
DMF: 30 mg/mL,DMSO: 30 mg/mL,Ethanol: 30 mg/mL,Ethanol:PBS (pH 7.2) (1:4): 0.2 mg/mL
保存条件
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°C,然后在超声波浴中震荡一段时间。
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。

计算工具摩尔浓度 / 稀释 / 分子量 / 单位换算 / 体内配方 / 溶解度

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