COX-1/cyclooxygenase-1 (IC50 = 3.2μM)

(-)-表儿茶素的 IC50 为 3.2 μM，在 70 μg/mL 浓度下对环加氧酶-1 (COX-1) 的抑制作用 > 95% [1]。 (-)-表儿茶素 NF-阻断 κB p65 亚基的核定位，从而阻止 IL-1β 诱导的 iNOS 产生。已证明，添加 IL-1β 会导致 (-)-表儿茶素爆发并限制 RINm5F 细胞中胰岛素的释放。此外，还证明(-)-表儿茶素具有溶胀性。它通过抑制 Jurkat T 细胞和霍奇金定位细胞的生长，增强 (-)-表儿茶素阻止 NF-κB 与这些细胞中的 DNA 结合的能力。将 20 μM 人参二醇与 150、200 或 250 μM (-)-表儿茶素组合可分别抑制人直肠癌 HCT-116 细胞的增殖 51%、97% 和 95%。膜联蛋白 V/PI 染色显示，交换后的细胞荧光水平分别增加了 11.9%、16.6% 和 25.8% [2]。

每天两次通过壁管饲法给动物喂水（媒介物）或1mg/kg的(-)-表儿茶素。在 15 天的过程中，锻炼组使用跑步机。使用 (-)-表儿茶素可以将原位访问期间的疲劳抵抗力提高约 30%，并将跑步机性能提高约 50% [3]。

Experimental design and approach[2]
A between-subjects design was used to determine the effects of (–)-epicatechin on the hindlimb muscles of 1-year-old mice. This age was selected because it has been shown that by 1 year there are decreases in exercise capacity when compared to young (4–6 months) mice (Leick et al. 2010). All animals performed an incremental treadmill test and were then subsequently randomized into four groups: (1) water, (2) water–exercise (W-Ex), (3) (–)-epicatechin ((–)-Epi), and (4) (–)-epicatechin–exercise ((–)-Epi-Ex). Groups 2 and 4 performed exercise on a rodent treadmill Monday through Friday during the study period. On the day after the final training session, all mice performed an incremental treadmill test. Forty-eight hours following the treadmill test, the mice were killed. The quadriceps femoris, extensor digitorum longus (EDL), and plantaris muscles for all groups were harvested and used for morphometric, biochemical, isolated-muscle preparation, and molecular analyses.

---

(–)-Epicatechin administration[3]
Mice in the (–)-epicatechin groups 3 and 4 were given 1.0 mg (kg body mass)−1 twice a day (morning and evening) for 15 consecutive days, whereas animals in the control groups 1 and 2 received the vehicle (water). Both (–)-epicatechin and vehicle were administered via oral gavage.

Metabolism / Metabolites
Epicatechin has known human metabolites that include 5-(3',4'-dihydroxyphenyl)-gamma-valerolactone and Phloroglucinol.

---

A small quantitative clinical study with human subjects consuming 80 grams of procyanidin-rich chocolate containing 137 mg (470 μmol) (−)-epicatechin showed that blood (−)-epicatechin increased 12-fold over baseline levels to 257 ± 66 nmol/L after 2 hours and then declined to baseline levels in 8 out of the ten subjects after 6 hours, while it further increased in the remaining two individuals [39]. This suggests that there is a large heterogeneity regarding the half-life and metabolism of (−)-epicatechin in humans. Bioavailability of native (−)-epicatechin is therefore smaller than for vitamins C and E, with about ~1/200 and ~1/150 bioavailability, respectively. Given that most of the ingested (−)-epicatechin undergoes chemical modifications, the glucuronidated and methylated products likely play a key role for the biological effect in addition to the native compound.[2]

[1]. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer. 2001;40(2):173-9.

[2]. Molecular Mechanisms and Therapeutic Effects of (-)-Epicatechin and Other Polyphenols in Cancer, Inflammation, Diabetes, and Neurodegeneration. Oxid Med Cell Longev. 2015;2015:181260.

[3]. (-)-Epicatechin enhances fatigue resistance and oxidative capacity in mouse muscle. J Physiol. 2011 Sep 15;589(Pt 18):4615-31.

(-)-epicatechin is a catechin with (2R,3R)-configuration. It has a role as an antioxidant. It is a polyphenol and a catechin. It is an enantiomer of a (+)-epicatechin.
Epicatechin has been used in trials studying the treatment of Pre-diabetes.
(-)-Epicatechin has been reported in Camellia sinensis, Cecropia hololeuca, and other organisms with data available.
An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.
See also: Crofelemer (monomer of); Bilberry (part of); Cat's Claw (part of) ... View More ...

---

With recent insight into the mechanisms involved in diseases, such as cardiovascular disease, cancer, stroke, neurodegenerative diseases, and diabetes, more efficient modes of treatment are now being assessed. Traditional medicine including the use of natural products is widely practiced around the world, assuming that certain natural products contain the healing properties that may in fact have a preventative role in many of the diseases plaguing the human population. This paper reviews the biological effects of a group of natural compounds called polyphenols, including apigenin, epigallocatechin gallate, genistein, and (-)-epicatechin, with a focus on the latter. (-)-Epicatechin has several unique features responsible for a variety of its effects. One of these is its ability to interact with and neutralize reactive oxygen species (ROS) in the cell. (-)-Epicatechin also modulates cell signaling including the MAP kinase pathway, which is involved in cell proliferation. Mutations in this pathway are often associated with malignancies, and the use of (-)-epicatechin holds promise as a preventative agent and as an adjunct for chemotherapy and radiation therapy to improve outcome. This paper discusses the potential of some phenolic compounds to maintain, protect, and possibly reinstate health.[2]
The flavanol (-)-epicatechin, a component of cacao (cocoa), has been shown to have multiple health benefits in humans. Using 1-year-old male mice, we examined the effects of 15 days of (-)-epicatechin treatment and regular exercise on: (1) exercise performance, (2) muscle fatigue, (3) capillarity, and (4) mitochondrial biogenesis in mouse hindlimb and heart muscles. Twenty-five male mice (C57BL/6N) were randomized into four groups: (1) water, (2) water-exercise (W-Ex), (3) (-)-epicatechin ((-)-Epi), and (4) (-)-epicatechin-exercise ((-)-Epi-Ex). Animals received 1 mg kg(-1) of (-)-epicatechin or water (vehicle) via oral gavage (twice daily). Exercise groups underwent 15 days of treadmill exercise. Significant increases in treadmill performance (∼50%) and enhanced in situ muscle fatigue resistance (∼30%) were observed with (-)-epicatechin. Components of oxidative phosphorylation complexes, mitofilin, porin, nNOS, p-nNOS, and Tfam as well as mitochondrial volume and cristae abundance were significantly higher with (-)-epicatechin treatment for hindlimb and cardiac muscles than exercise alone. In addition, there were significant increases in skeletal muscle capillarity. The combination of (-)-epicatechin and exercise resulted in further increases in oxidative phosphorylation-complex proteins, mitofilin, porin and capillarity than (-)-epicatechin alone. These findings indicate that (-)-epicatechin alone or in combination with exercise induces an integrated response that includes structural and metabolic changes in skeletal and cardiac muscles resulting in greater endurance capacity. These results, therefore, warrant the further evaluation of the underlying mechanism of action of (-)-epicatechin and its potential clinical application as an exercise mimetic.[3]

C15H14O6

290.27

290.079

C, 62.07; H, 4.86; O, 33.07

490-46-0

(-)-Epicatechin gallate;1257-08-5;(+)-Epicatechin;35323-91-2;(±)-Epicatechin-13C3;1217780-28-3; 490-46-0

72276

White to light yellow solid powder

1.6±0.1 g/cm3

630.4±55.0 °C at 760 mmHg

240 °C (dec.)(lit.)

335.0±31.5 °C

0.0±1.9 mmHg at 25°C

1.742

0.49

110.38

5

6

1

21

364

2

C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O

PFTAWBLQPZVEMU-UKRRQHHQSA-N

InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

epi-Catechin; (-)-Epicatechin; (-)-Epicatechin; Epicatechin; 490-46-0; L-Epicatechin; Epicatechol; l-Acacatechin; (-)-Epicatechol; epi-Catechin; Epicatechin

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~344.51 mM)
H2O : ~2 mg/mL (~6.89 mM)

配方 1 中的溶解度: ≥ 2.5 mg/mL (8.61 mM) (饱和度未知) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将100 μL 25.0 mg/mL澄清DMSO储备液加入到400 μL PEG300中，混匀；然后向上述溶液中加入50 μL Tween-80，混匀；加入450 μL生理盐水定容至1 mL。
*生理盐水的制备：将 0.9 g 氯化钠溶解在 100 mL ddH₂O中，得到澄清溶液。

---

配方 2 中的溶解度: ≥ 2.5 mg/mL (8.61 mM) (饱和度未知) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL澄清DMSO储备液加入900 μL 20% SBE-β-CD生理盐水溶液中，混匀。
*20% SBE-β-CD 生理盐水溶液的制备（4°C，1 周）：将 2 g SBE-β-CD 溶解于 10 mL 生理盐水中，得到澄清溶液。

---

View More

配方 3 中的溶解度: ≥ 2.5 mg/mL (8.61 mM) (饱和度未知) in 10% DMSO + 90% Corn Oil (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 25.0 mg/mL 澄清 DMSO 储备液加入到 900 μL 玉米油中并混合均匀。

---

请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。