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
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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25857215 |
|||
Target ID: GO:0016209 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10528992 |
|||
Target ID: GO:0070527 |
|||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21875098 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Preventing | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26657737
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20002836
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
Edited
Sat Dec 16 11:23:23 GMT 2023
by
admin
on
Sat Dec 16 11:23:23 GMT 2023
|
Record UNII |
H1059K9GIN
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
475277
Created by
admin on Sat Dec 16 11:23:23 GMT 2023 , Edited by admin on Sat Dec 16 11:23:23 GMT 2023
|
PRIMARY | |||
|
H1059K9GIN
Created by
admin on Sat Dec 16 11:23:23 GMT 2023 , Edited by admin on Sat Dec 16 11:23:23 GMT 2023
|
PRIMARY | |||
|
DTXSID601030258
Created by
admin on Sat Dec 16 11:23:23 GMT 2023 , Edited by admin on Sat Dec 16 11:23:23 GMT 2023
|
PRIMARY | |||
|
Cinnamtannin B1
Created by
admin on Sat Dec 16 11:23:23 GMT 2023 , Edited by admin on Sat Dec 16 11:23:23 GMT 2023
|
PRIMARY | |||
|
88082-60-4
Created by
admin on Sat Dec 16 11:23:23 GMT 2023 , Edited by admin on Sat Dec 16 11:23:23 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
|