原花青素C1

原花青素C1
	IUPAC名; (12R,13R,14R,22R,23R,24S,32R,33R)-12,22,32-Tris(3,4-dihydroxyphenyl)-12H,22H,32H-[14,28:24,38-ter-1-benzopyran]-13,15,17,23,25,27,33,35,37-nonol
别名	Procyanidin C1; Procyanidol C1; Epicatechin-(4.beta.-->8)epicatechin-(4.beta.-->8)epicatechin; Epicatechin-(4β→8)-epicatechin--(4β→8)-epicatechin
识别
CAS号	37064-30-5
PubChem	169853
ChemSpider	148540
SMILES	c1cc(c(cc1[C@@H]2[C@@H](Cc3c(cc(c(c3O2)[C@H]4c5c(cc(c(c5O[C@@H]([C@@H]4O)c6ccc(c(c6)O)O)[C@H]7c8c(cc(cc8O[C@@H]([C@@H]7O)c9ccc(c(c9)O)O)O)O)O)O)O)O)O)O)O;
InChI	1/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1;
InChIKey	MOJZMWJRUKIQGL-XILRTYJMBW
ChEBI	75643
KEGG	C17624
性质
化学式	C45H38O18
摩尔质量	866.77 g/mol g·mol⁻¹
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

原花青素C1（Procyanidin C1，简称PCC1）是一种B型前花青素（B type proanthocyanidin），是一种可在酿酒葡萄中找到的表儿茶素三聚体。^[1]

自然中的分布与功用

原花青素C1可从酿酒葡萄的种子萃取物中分离出来。^[2]

化学合成

有七种芐酯前花青素三聚体（其中包括原花青素C1、原花青素C2及其他几种“表儿茶素-(4β-8)-儿茶素-(4α-8)-表儿茶素”三聚体），可透过以三氟甲磺酸三甲基硅酯进行催化的凝结反应进行高产量的不对称合成；而苄酯化的原花青素C2的结构可借由比较以两种不同路径合成的受保护的原花青素C2的1H NMR光谱进行确认；此外，对“(+)-儿茶素”以及“(-)-表儿茶素”三聚体衍生物的去保护作用，可以相当良好的产量制成四种自然的原花青素三聚体。^[3]

研究

原花青素C1可以延长老鼠的寿命并使其更加健康；此外，在植入人类前列腺癌细胞的小鼠模型中，原花青素C1可以大幅增加化学疗法的效果。^[2]^[4]

外部链接

Carissa Wong: Grape seed chemical allows mice to live longer by killing aged cells （页面存档备份，存于互联网档案馆）. NewScientist, 6 December 2021

参考资料

^ Proanthocyanidin composition of red Vitis vinifera varieties from the Douro valley during ripening : Influence of cultivation altitude. Mateus Nuno, Marques Sara, Goncalves Ana C., Machado José M. and De Freitas Victor, American journal of enology and viticulture, 2001, vol. 52, no2, pp. 115-121, INIST（法语：Institut de l'information scientifique et technique）:1129642
^ ^2.0 ^2.1 Carissa Wong. Grape seed chemical allows mice to live longer by killing aged cells. New Scientist. Dec 6, 2021 [2022-02-07]. （原始内容存档于2021-12-21）.
^ Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation. Akiko Saito, Akira Tanaka, Makoto Ubukata and Noriyuki Nakajima, Synlett, 2004, volume 6, pages 1069-1073, doi:10.1055/s-2004-822905
^ Xu, Qixia; et al. The flavonoid procyanidin C1 has senotherapeutic activity and increases lifespan in mice. Nature Metabolism. Dec 6, 2021 [2022-02-07]. doi:10.1038/s42255-021-00491-8. （原始内容存档于2022-02-18）.

[1] Proanthocyanidin composition of red Vitis vinifera varieties from the Douro valley during ripening : Influence of cultivation altitude. Mateus Nuno, Marques Sara, Goncalves Ana C., Machado José M. and De Freitas Victor, American journal of enology and viticulture, 2001, vol. 52, no2, pp. 115-121, INIST（法语：Institut de l'information scientifique et technique）:1129642

[Wong-2] 2.0 ^2.1 Carissa Wong. Grape seed chemical allows mice to live longer by killing aged cells. New Scientist. Dec 6, 2021 [2022-02-07]. （原始内容存档于2021-12-21）.

[3] Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation. Akiko Saito, Akira Tanaka, Makoto Ubukata and Noriyuki Nakajima, Synlett, 2004, volume 6, pages 1069-1073, doi:10.1055/s-2004-822905

[4] Xu, Qixia; et al. The flavonoid procyanidin C1 has senotherapeutic activity and increases lifespan in mice. Nature Metabolism. Dec 6, 2021 [2022-02-07]. doi:10.1038/s42255-021-00491-8. （原始内容存档于2022-02-18）.

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