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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H20O3
Molecular Weight 248.3175
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REYNOSIN

SMILES

[H][C@@]12CC[C@@]3(C)[C@H](O)CCC(=C)[C@]3([H])[C@@]1([H])OC(=O)C2=C

InChI

InChIKey=FKBUODICGDOIGB-PFFFPCNUSA-N
InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h10-13,16H,1-2,4-7H2,3H3/t10-,11+,12+,13-,15-/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H20O3
Molecular Weight 248.3175
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
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/10985075 | https://www.ncbi.nlm.nih.gov/pubmed/27180996 | https://www.ncbi.nlm.nih.gov/pubmed/16142632

Reynosin is a sesquiterpene lactone isolated from roots of Saussrurea lappa, Tsoongiodendron odorum, Manglietiastrum sinicum, Ambrosia confertiflora and other plants. Reynosin showed inhibition of platelet aggregation induced by AA, by ADP, or by PAF, inhibition of nitric oxide production in lipopolysaccharide (LPS)-activated murine macrophages, dose-dependent inhibition on CINC-1 induction in LPS-stimulated NRK-52E cells. Reynosin demonstrated bactericidal activity agains clinical strains of Mycobacterium tuberculosis.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Reynosin from Sassurea lappa as inhibitor on CINC-1 induction in LPS-stimulated NRK-52E cells.
1998 Jun
Antimycobacterial evaluation of germacranolides.
1998 Sep
Chemical constituents of two Chinese Magnoliaceae plants, Tsoongiodendron odorum and Manglietiastrum sinicum, and their inhibition of platelet aggregation.
2000 Aug
Antimycobacterial plant terpenoids.
2001 Nov
New sesquiterpene lactones from Laurus nobilis leaves as inhibitors of nitric oxide production.
2005 Aug
Reynosin and santamarine: two sesquiterpene lactones from Ambrosia confertiflora with bactericidal activity against clinical strains of Mycobacterium tuberculosis.
2016 Nov
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
To evaluate the anti-mycobacterial activity, the redox microplate Alamar BlueVR assay was performed. The assay was performed on 96-well polystyrene flat bottom plates with low evaporation cover lids. First, 200 uL of sterile distilled water was added to the perimetral wells and 100 uL of Middlebrook 7H9 broth supplemented with OADC was added to the remaining wells. The working solutions of compounds (512 lg/mL) were distributed into the first well of each row, from which a 2-fold dilution series was made using the following three wells. The final concentrations in-test ranged from 128 to 16 ug/mL. Then, 100 uL of the Mtb inoculum was added. Rifampin was used (15–9.15*10^-4 ug/mL) as a control. Simultaneously, a 1:100 dilution prepared from the bacterial inoculum (representing the growth of 1% of the bacterial population) and a growth control were included. As negative controls, 200 lL of culture medium alone and 200 lL of the maximum tested concentration of the compounds (without bacteria) were used. The plates were incubated at 37 C. After 5 d of incubation, 50 lL of a fresh Alamar Blue-10% Tween 80 mixture (1:1) was added to each control well. The microplate was sealed with parafilm and reincubated for 24 h at 37 C. If the negative controls remained blue and the positive controls turned pink, the reagent mixture was added to all of the wells in the microplate. The microplates were resealed with parafilm and incubated for an additional 48 h; then, the colors of all wells were recorded. Finally, the visual MICs were defined as the lowest compound or antibiotic concentration at which no color change in the indicator was evident.
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:13:18 GMT 2023
Edited
by admin
on Fri Dec 15 20:13:18 GMT 2023
Record UNII
N26569L9V4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REYNOSIN
Common Name English
REYNOSIN, (+)-
Common Name English
NAPHTHO(1,2-B)FURAN-2(3H)-ONE, DECAHYDRO-6-HYDROXY-5A-METHYL-3,9-BIS(METHYLENE)-, (3AS-(3A.ALPHA.,5A.BETA.,6.BETA.,9A.ALPHA.,9B.BETA.))-
Common Name English
NSC-155623
Code English
EUDESMA-4(14),11(13)-DIEN-12-OIC ACID, 1.BETA.,6.ALPHA.-DIHYDROXY-, .GAMMA.-LACTONE
Common Name English
NAPHTHO(1,2-B)FURAN-2(3H)-ONE, DECAHYDRO-6-HYDROXY-5A-METHYL-3,9-BIS(METHYLENE)-, (3AS,5AR,6R,9AS,9BS)-
Common Name English
REINOSIN
Common Name English
(+)-REYNOSIN
Common Name English
Code System Code Type Description
PUBCHEM
482788
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY
CHEBI
540787
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID80950973
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY
NSC
155623
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY
FDA UNII
N26569L9V4
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY
CAS
28254-53-7
Created by admin on Fri Dec 15 20:13:18 GMT 2023 , Edited by admin on Fri Dec 15 20:13:18 GMT 2023
PRIMARY