U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Identification of phenolics in litchi and evaluation of anticancer cell proliferation activity and intracellular antioxidant activity.
2015 Jul
Trimer procyanidin oligomers contribute to the protective effects of cinnamon extracts on pancreatic β-cells in vitro.
2016 Aug
Structural characterization and bioactivity of proanthocyanidins from indigenous cinnamon (Cinnamomum osmophloeum).
2016 Nov
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 Sat Dec 16 11:23:23 UTC 2023
Edited
by admin
on Sat Dec 16 11:23:23 UTC 2023
Record UNII
H1059K9GIN
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Dec 16 11:23:23 UTC 2023 , Edited by admin on Sat Dec 16 11:23:23 UTC 2023
PRIMARY
FDA UNII
H1059K9GIN
Created by admin on Sat Dec 16 11:23:23 UTC 2023 , Edited by admin on Sat Dec 16 11:23:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID601030258
Created by admin on Sat Dec 16 11:23:23 UTC 2023 , Edited by admin on Sat Dec 16 11:23:23 UTC 2023
PRIMARY
WIKIPEDIA
Cinnamtannin B1
Created by admin on Sat Dec 16 11:23:23 UTC 2023 , Edited by admin on Sat Dec 16 11:23:23 UTC 2023
PRIMARY
CAS
88082-60-4
Created by admin on Sat Dec 16 11:23:23 UTC 2023 , Edited by admin on Sat Dec 16 11:23:23 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP