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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H36O18
Molecular Weight 864.7565
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CINNAMTANNIN B1

SMILES

[H][C@@]1(O)[C@@H]2C3=C(O)C=C(O)C=C3O[C@]1(OC4=C2C5=C([C@@H]([C@@H](O)[C@H](O5)C6=CC(O)=C(O)C=C6)C7=C8O[C@@H]([C@H](O)CC8=C(O)C=C7O)C9=CC(O)=C(O)C=C9)C(O)=C4)C%10=CC(O)=C(O)C=C%10

InChI

InChIKey=BYSRPHRKESMCPO-WIYGYKBVSA-N
InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)62-45(17-3-6-22(49)26(53)9-17)44(59)38(33)36-32(63-45)14-29(56)35-37(39(58)41(61-43(35)36)16-2-5-21(48)25(52)8-16)34-28(55)13-23(50)19-12-30(57)40(60-42(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38?,39-,40-,41-,44-,45+/m1/s1

HIDE SMILES / InChI

Molecular Formula C45H36O18
Molecular Weight 864.7565
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Cinnamtannin B-1 is a naturally occurring A-type proanthocyanidins, available in a limited number of plants, including C. zeylanicum and L. nobilis, that exhibit a large number of cellular actions mostly derived from its antioxidant activity, including antitumoral activity mediated by a selective pro-apoptotic action in a number of tumoral cell lines associated with a remarkable antiapoptotic activity in normal cells. In addition, cinnamtannin B-1 shows antithrombotic actions through inhibition of platelets' endogenous ROS generation, Ca2 mobilization and subsequently aggregation. This has been reported to be especially relevant in platelets from diabetic patients where cinnamtannin B-1 reverses both platelet hypersensitivity and hyperactivity. Considering the large number of cellular effects of cinnamtannin B-1, this compound might be further investigated for the development of therapeutic strategies based on its use for thrombotic disorders or certain types of cancer. Cinnamtannin B-1 is a potent antioxidant and protective agent against oxidative stress and apoptosis in human platelets. Cinnamtannin B-1 is a Cox-2 (cyclooxygenase-2) inhibitor. Cinnamtannin B1 was a potent cancer cell proliferation inhibitor and a good intracellular antioxidant.

Approval Year

PubMed

PubMed

TitleDatePubMed
Immunosuppressive Effects of A-Type Procyanidin Oligomers from Cinnamomum tamala.
2014
Patents

Sample Use Guides

Mice: Six male C57BL/6 mice each from the control and cinnamtannin B-1-treated groups were injected with 0.4 mL phosphate-buffered saline (PBS) or cinnamtannin B-1 solution (2.0 mg/kg via the vena caudalis), respectively.
Route of Administration: Intravenous
Cinnamtannin B-1 (10 uM) significantly reduced Ca(2+) influx in mouse pancreatic acinar cells evoked by cholecystokinin in the presence of ethanol.
Substance Class Chemical
Created
by admin
on Sun Dec 18 07:33:19 UTC 2022
Edited
by admin
on Sun Dec 18 07:33:19 UTC 2022
Record UNII
H1059K9GIN
Record Status Validated (UNII)
Record Version
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Name Type Language
CINNAMTANNIN B1
Common Name English
(-)-EPICATECHIN-(4.BETA.->8, 2.BETA.-O->7)-EPICATECHIN-(4.BETA.->8)-EPICATECHIN)
Common Name English
8,14-METHANO-2H,14H-1-BENZOPYRANO(7,8-D)(1,3)BENZODIOXOCIN-3,5,11,13,15-PENTOL, 2,8-BIS(3,4-DIHYDROXYPHENYL)-4-((2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-3,5,7-TRIHYDROXY-2H-1-BENZOPYRAN-8-YL)-3,4-DIHYDRO-, (2R,3R,4S,8S,14R,15R)-
Systematic Name English
CINNAMTANNIN B1 (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]
Common Name English
CINNAMTANNIN B1 (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]
Common Name English
(-)-EPICATECHIN-(4BETA-8, 2BETA-OMICRON-7)-EPICATECHIN-(4BETA-8)-EPICATECHIN)
Common Name English
LDN 0022358
Code English
LDN-0022358
Code English
Code System Code Type Description
PUBCHEM
475277
Created by admin on Sun Dec 18 07:33:20 UTC 2022 , Edited by admin on Sun Dec 18 07:33:20 UTC 2022
PRIMARY
FDA UNII
H1059K9GIN
Created by admin on Sun Dec 18 07:33:20 UTC 2022 , Edited by admin on Sun Dec 18 07:33:20 UTC 2022
PRIMARY
EPA CompTox
DTXSID601030258
Created by admin on Sun Dec 18 07:33:20 UTC 2022 , Edited by admin on Sun Dec 18 07:33:20 UTC 2022
PRIMARY
WIKIPEDIA
Cinnamtannin B1
Created by admin on Sun Dec 18 07:33:20 UTC 2022 , Edited by admin on Sun Dec 18 07:33:20 UTC 2022
PRIMARY
CAS
88082-60-4
Created by admin on Sun Dec 18 07:33:20 UTC 2022 , Edited by admin on Sun Dec 18 07:33:20 UTC 2022
PRIMARY
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