Name | Procyanidin B3 |
Synonyms | Procyanidin B3 Procyanidol B3 PROCYANIDIN B3 [4,8''-Biflavan]-3,3',3'',3''',4',4''',5,5'',7,7''-decol stereoisomer (2R,2'R,3S,3'S,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-4,8'-bichroman-3,3',5,5',7,7'-hexol (2R,2'R,3S,3'S,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichroman]-3,3',5,5',7,7'-hexaol (2R,2'R,3S,3'S,4α)-3,3',4,4'-Tetrahydro-2α,2'α-bis(3,4-dihydroxyphenyl)-4,8'-bi[2H-1-benzopyran]-3,3',5,5',7,7'-hexol |
CAS | 23567-23-9 |
Molecular Formula | C30H26O12 |
Molar Mass | 578.52 |
Density | 1.705 |
Melting Point | 218-219℃ |
Boling Point | 955.3±65.0 °C(Predicted) |
Appearance | Powder |
pKa | 9.29±0.60(Predicted) |
Storage Condition | Sealed in dry,2-8°C |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
Reference Show more | 1. Xianan Zhang, Xin Li, Mingshen Su, Jihong Du, Huijuan Zhou, Xiongwei Li, Zhengwen Ye, A comparative UPLC-Q-TOF/MS-based metabolomics approach for distinguishing peach (Prunus persica (L.) Batsch) fruit cultivars with varying antioxidant activity, Food Rese 2. Yan, Fangfang, et al. "Comparison of the inhibitory effects of procyanidins with different structures and their digestion products against acrylamide-induced cytotoxicity in IPEC-J2 cells." Journal of Functional Foods 72 (2020): 104073.https://doi.org/10.1 3. [IF=6.475] Xianan Zhang et al."A comparative UPLC-Q-TOF/MS-based metabolomics approach for distinguishing peach (Prunus persica (L.) Batsch) fruit cultivars with varying antioxidant activity."Food Res Int. 2020 Nov;137:109531 4. [IF=4.451] Fangfang Yan et al."Comparison of the inhibitory effects of procyanidins with different structures and their digestion products against acrylamide-induced cytotoxicity in IPEC-J2 cells."J Funct Foods. 2020 Sep;72:104073 |
Polyflavonoids | Proanthocyanidin B3 is a polyflavonoid compound formed by connecting flavan-3-ol units through C- C or C- O-C. It has antioxidant, scavenging free radicals, inhibiting tumor growth and other physiological activities. |
physical properties | brown amorphous powder,[α]18D-158.0 °(c = 0.5, acetone-water, 1:1),[α]D-235 ° (aqueous methanol),Rf (toluene-acetone-formic acid, 3:6:1):0.40[3]. 13CNMR. fig. 1 is the structural formula of the original flower Qingsu B3. |
Plant source | 1. Birch family (Betulaceae): Betula pubescens Ehrh. Inner bark; Betula spp. 2. Camellia family (Camelliaceae): Pu'er tea Camellia sinensis var.assamica Kitamura leaves (yield: 0.0006%) 3. Rhododendron family (Ericaceae): blueberry Vaccinium vitis-idaea L. leaves 4. Palmae: Areca catechu L. 5. Pinaceae (Pinaceae): larix gmelini(Rupr.)Rupr. Bark 6. Pyrola family (Pyrolaceae): Pyrola incarnata Fisch. ex DC. Whole herb 7. Rosaceae (Rosaceae): Potentilla Patentilla viscosa J.Don root; Rosa henryi Bouleng of seven roses. Root; Rosa laevigata Michx. Leaves 8. Willow family (Salicaceae): Salix caprea L. Catkins 9. Saxifraga family (Saxifragaceae): Chinese cabbage Bergenia purpurascens Engl. Root (yield: 0.096%) 10. Grape family (Vitaceae): Vitis vinifera L. seed, residue |
physiological effects | procyanidins are a good oxygen free radical scavenger and lipid peroxidation inhibitor. their main functions are: ① effectively scavenging superoxide anion radicals and hydroxyl radicals, etc., and can also interrupt the free radical chain reaction. ② Participate in the metabolism and protein phosphorylation of phospholipids and arachidonic acid, protect lipids from peroxidation damage. ③ It is a powerful metal chelating agent, which can chelate metal ions and form inert compounds in the body. ④ Protect and stabilize vitamin C, which helps the absorption of vitamin C. This information is edited and sorted out by Yalin. |
biological activity | Procyanidin B3 is a natural product, a specific inhibitor of histone acetyltransferase (HAT), which can bind to other sites of p300 instead of inactive sites to selectively inhibit p300-mediated acetylation of androgen receptors. Procyanidin B3 had no effect on HDAC or histone methyltransferase (HMT). |
target | p300 |
use | used for content determination/identification/pharmacological experiments, etc. |