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Chlorophyll a

(Synonyms: 叶绿素A) 目录号 : GC49064

Chlorophyll a是主要的光合色素,在放氧光合作用中具有双重功能:既捕获光能,又将吸收的光子能量转化为化学能。

Chlorophyll a Chemical Structure

Cas No.:479-61-8

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500 µg
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1 mg
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5 mg
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Sample solution is provided at 25 µL, 10mM.

Description

Chlorophyll a, the main photosynthetic pigment, serves a dual role in oxygenic photosynthesis: in light harvesting as well as in converting the energy of absorbed photons to chemical energy[1]. Chlorophyll a exhibits both antioxidant and immunostimulatory properties[2]. Chlorophyll a absorbs light most efficiently in the red and blue regions of the spectrum, with peak absorption at around 430 and 662 nanometers, respectively[3].

In vitro, treating 3T3-L1 cells for 48h with chlorophyll a at 0, 5, 10, or 30nM induced cell cycle arrest at the G0/G1 phase and caused a decrease in the S phase in a dose–response manner[4]. Treating HEK293 cells with chlorophyll a (5-20μg/mL) for 30min concentration-dependently inhibited lipopolysaccharide-induced tumor necrosis factor-α gene expression, with almost complete suppression observed at 5μg/mL[5]. Treating C3H10T1/2 cells with 10µg/mL chlorophyll a markedly down-regulated the protein levels of the adipogenic transcription factors CCAAT/enhancer-binding protein alpha (C/EBPα), peroxisome proliferator-activated receptor gamma (PPARγ), and adipocyte protein 2 (aP2)[6].

In vivo, topical pretreatment of BALB/c mice dorsal skin with 50 or 250μg chlorophyll a significantly and dose-dependently reduced both the incidence of tumors and the average number of tumors per mouse[7]. Feeding rats 1.2mmol/kg of natural chlorophyll a for 14 days completely blocked heme-induced increases in colonic cytotoxicity, epithelial hyperproliferation, accelerated epithelial turnover, and lipid-radical formation[8].

References:
[1] Björn LO, Papageorgiou GC, Blankenship RE, Govindjee. A viewpoint: why chlorophyll a?. Photosynth Res. 2009;99(2):85-98.
[2] Yang Z, Li F, Shen S, et al. Natural chlorophyll: a review of analysis methods, health benefits, and stabilization strategies. Crit Rev Food Sci Nutr. 2025;65(16):3069-3083.
[3] Martins T, Barros AN, Rosa E, Antunes L. Enhancing Health Benefits through Chlorophylls and Chlorophyll-Rich Agro-Food: A Comprehensive Review. Molecules. 2023 Jul 11;28(14):5344.
[4] Wu SJ, Ng LT, Wang GH, Huang YJ, Chen JL, Sun FM. Chlorophyll a, an active anti-proliferative compound of Ludwigia octovalvis, activates the CD95 (APO-1/CD95) system and AMPK pathway in 3T3-L1 cells. Food Chem Toxicol. 2010;48(2):716-721.
[5] Subramoniam A, Asha VV, Nair SA, et al. Chlorophyll revisited: anti-inflammatory activities of chlorophyll a and inhibition of expression of TNF-α gene by the same. Inflammation. 2012;35(3):959-966.
[6] Seo YJ, Kim KJ, Choi J, Koh EJ, Lee BY. Spirulina maxima Extract Reduces Obesity through Suppression of Adipogenesis and Activation of Browning in 3T3-L1 Cells and High-Fat Diet-Induced Obese Mice. Nutrients. 2018;10(6):712.
[7] Higashi-Okai K, Okai Y. Potent suppressive activity of chlorophyll a and b from green tea (Camellia sinensis) against tumor promotion in mouse skin. J UOEH. 1998;20(3):181-188.
[8] de Vogel J, Jonker-Termont DS, Katan MB, van der Meer R. Natural chlorophyll but not chlorophyllin prevents heme-induced cytotoxic and hyperproliferative effects in rat colon. J Nutr. 2005;135(8):1995-2000.

Chlorophyll a是主要的光合色素,在放氧光合作用中具有双重功能:既捕获光能,又将吸收的光子能量转化为化学能[1]。Chlorophyll a具有抗氧化和免疫刺激特性[2]。对光谱的红光和蓝光吸收效率最高,吸收峰分别约为430nm和662nm[3]

在体外,用0、5、10或30nM的Chlorophyll a处理3T3-L1细胞48h,可剂量依赖性地诱导细胞周期阻滞于G0/G1期并降低S期比例[4]。用5-20μg/mL的Chlorophyll a处理HEK293细胞30min,可浓度依赖性地抑制脂多糖诱导的肿瘤坏死因子-α基因表达,5μg/mL时几乎完全抑制[5]。用10μg/mL的Chlorophyll a处理C3H10T1/2细胞,显著下调成脂转录因子(C/EBPα)、过氧化物酶体增殖物激活受体γ(PPARγ)和脂肪细胞蛋白2(aP2)的蛋白水平[6]

在体内,在BALB/c小鼠背部皮肤预先局部涂抹50或250μg的Chlorophyll a,可剂量依赖性地显著降低肿瘤发生率及平均每只鼠的肿瘤数[7]。大鼠连续14天按1.2mmol/kg饲喂Chlorophyll a,可完全阻断血红素诱导的结肠细胞毒性升高、上皮过度增殖、上皮更新加速及脂质自由基形成[8]

实验参考方法

Cell experiment [1]:

Cell lines

3T3-L1 cell

Preparation Method

Cells were treated with Chlorophyll a at various concentrations (0, 5,10, and 30nM) for 48h. Floating and adherent cells were then collected. The cells in suspension were fixed with 70% ice-cold methanol and then stored in the freezer until use. After washing with PBS, cells were stained with 50μg/ml propidium iodide (PI) in the presence of 25μg/ml RNase A at 37°C for 30min. A minimum of 10,000 cells per sample was collected. To estimate the percentage of each phase in the cell cycle, the DNA histograms were analyzed by Multicycle software.

Reaction Conditions

0, 5,10, and 30nM; 48h

Applications

After 48h of treatment, Chlorophyll a induced cell cycle arrest at the G0/G1 phase and caused a decrease in the S phase in a dose–response manner.

Animal experiment [2]:

Animal models

BALB/c mice

Preparation Method

Ten 7-week-old female BALB/c mice were assigned to each experimental group. In the positive-control group (Experiment A), tumorigenesis was initiated with a single dorsal application of 50nmol 7,12-dimethylbenz [a] anthracene (DMBA) in 200μL acetone; one week later, 2nmol 12-O-tetradecanoyl-phorbol-13-acetate (TPA) in 200μL acetone was applied twice weekly for 20 weeks as the promotion regimen. To examine the inhibitory effect of chlorophyll a, a parallel set of mice (Experiment B) received the same DMBA initiation, followed by topical application of chlorophyll a (50 or 250μg in 200μL acetone) 80min before each TPA treatment for 20 weeks.

Dosage form

50 or 250μg; topical application

Applications

Treatment with 50nmol DMBA as initiator, followed by twice-weekly 2nmol TPA as promoter, resulted in a markedly elevated skin tumor incidence: all mice developed tumors, averaging 20.1±4.3 tumors per animal. Pretreating the dorsal skin with 50 or 250μg of chlorophyll a 80min before each TPA application, however, produced a dose-dependent and significant suppression of both tumor incidence and the mean number of tumors per mouse.

References:
[1] Wu SJ, Ng LT, Wang GH, Huang YJ, Chen JL, Sun FM. Chlorophyll a, an active anti-proliferative compound of Ludwigia octovalvis, activates the CD95 (APO-1/CD95) system and AMPK pathway in 3T3-L1 cells. Food Chem Toxicol. 2010;48(2):716-721.
[2] Higashi-Okai K, Okai Y. Potent suppressive activity of chlorophyll a and b from green tea (Camellia sinensis) against tumor promotion in mouse skin. J UOEH. 1998;20(3):181-188.

化学性质

Cas No. 479-61-8 SDF
别名 叶绿素A
Canonical SMILES CC1=C2[N-](C3=C1C4=O)[Mg+2]56[N](C([C@H]7CCC(OC/C=C(C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)=O)=C3[C@H]4C(OC)=O)=C([C@H]7C)C=C8[N-]5C(C(C=C)=C8C)=CC9=[N]6C(C(CC)=C9C)=C2
分子式 C55H72MgN4O5 分子量 893.5
溶解度 Acetone: soluble,Ethanol: soluble 储存条件 -20°C
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1 mM 1.1192 mL 5.596 mL 11.1919 mL
5 mM 0.2238 mL 1.1192 mL 2.2384 mL
10 mM 0.1119 mL 0.5596 mL 1.1192 mL
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