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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H32O7
Molecular Weight 372.4532
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BYZANTIONOSIDE B

SMILES

C[C@H](CC[C@H]1C(C)=CC(=O)CC1(C)C)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O

InChI

InChIKey=NYLNHNDMNOPWAZ-ZLEFDVGRSA-N
InChI=1S/C19H32O7/c1-10-7-12(21)8-19(3,4)13(10)6-5-11(2)25-18-17(24)16(23)15(22)14(9-20)26-18/h7,11,13-18,20,22-24H,5-6,8-9H2,1-4H3/t11-,13+,14-,15-,16+,17-,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H32O7
Molecular Weight 372.4532
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24785825

Byzantionoside B was isolated from the aerial parts of Stachys byzantina as the C-9 epimer of blumenol C glucoside. Byzantionoside B showed osteogenic activity by increasing alkaline phosphatase activity and calcium contents to regulate differentiation and mineralization in human osteoblast cells.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
New megastigmane glycoside and aromadendrane derivative from the aerial part of Piper elongatum.
2002 Oct
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Byzantionoside B significantly increased alkaline phosphatase activity in human osteoblast cells when used at a concentration of 100 μM and also increased the calcium contents of the mineralized matrix. At the same concentration. Byzantionoside B upregulated the mRNA expression of osteopontin, bone morphogenetic protein-2, and runt-related transcription factor 2 in human osteoblast cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:08:54 UTC 2023
Edited
by admin
on Sat Dec 16 11:08:54 UTC 2023
Record UNII
6C3V404S0G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BYZANTIONOSIDE B
Common Name English
(6R,9R)-9-HYDROXYMEGASTIGMAN-4-EN-3-ONE 9-O-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
(+)-BYZANTIONOSIDE B
Common Name English
BLUMENOL C GLUCOSIDE
Common Name English
2-CYCLOHEXEN-1-ONE, 4-((3R)-3-(.BETA.-D-GLUCOPYRANOSYLOXY)BUTYL)-3,5,5-TRIMETHYL-, (4R)-
Systematic Name English
BLUMENOL C .BETA.-D-GLUCOPYRANOSIDE
Common Name English
Code System Code Type Description
PUBCHEM
14135395
Created by admin on Sat Dec 16 11:08:54 UTC 2023 , Edited by admin on Sat Dec 16 11:08:54 UTC 2023
PRIMARY
CAS
135820-80-3
Created by admin on Sat Dec 16 11:08:54 UTC 2023 , Edited by admin on Sat Dec 16 11:08:54 UTC 2023
PRIMARY
FDA UNII
6C3V404S0G
Created by admin on Sat Dec 16 11:08:54 UTC 2023 , Edited by admin on Sat Dec 16 11:08:54 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Compound was extracted from the dried leaves of N. tabacum (3.5 kg) with 90% EtOH at room temperature and partitioned between EtOAc and H2O.