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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26O5
Molecular Weight 346.4174
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROSMANOL

SMILES

[H][C@@]12[C@@H]3OC(=O)[C@@]1(CCCC2(C)C)C4=C(C=C(C(C)C)C(O)=C4O)[C@@H]3O

InChI

InChIKey=LCAZOMIGFDQMNC-FORWCCJISA-N
InChI=1S/C20H26O5/c1-9(2)10-8-11-12(15(23)13(10)21)20-7-5-6-19(3,4)17(20)16(14(11)22)25-18(20)24/h8-9,14,16-17,21-23H,5-7H2,1-4H3/t14-,16+,17-,20-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19711987 | https://www.ncbi.nlm.nih.gov/pubmed/25200369

Rosmanol is a natural polyphenol from the herb rosemary (Rosmarinus officinalis L.) with high antioxidant activity. Rosmanol markedly inhibited LPS-stimulated iNOS and COX-2 protein and gene expression, as well as the downstream products, NO and PGE2 in RAW 264.7 cells. Treatment with Rosmanol also reduced translocation of the nuclear factor-κB (NF-κB) subunits by prevention of the degradation and phosphorylation of inhibitor κB (IκB). Rosmanol exerted significant antinociceptive effects in both hot plate and tail immersion tests at the dose level of 10-100 mg/kg. The cellular and neural mechanisms underlying pain responses elicited involve interplay of a number of neurotransmitters and ion channel, and the central analgesic effects of Rosmanol were not antagonized by the opioid receptor antagonist naloxone. This indicates that the central analgesic effects of Rosmanol may be exerted via one or more of several proposed nonopioid mechanisms such as blockade of voltage-gated Na+ channels, activation of the noradrenergic inhibitory system, enhancement of GABAergic and/or serotonergic systems. The physiological and toxicological properties of this compound have not been evaluated in humans.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available

Originator

Sources: Khimiya Prirodnykh Soedinenii (1971), 7, (4), 416-20.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Swiss albino mice (25–30g) were treated with Rosmanol (50, 150 and 200 mg/kg).
Route of Administration: Intraperitoneal
Antimicrobial activity was determined against Gram-positive (Bacillus subtilis ATCC 6051, B. cereus ATCC 21772, Staphylococcus aureus ATCC 6538, S. epidermidis ATCC 14990, Enterococcus faecalis ATCC 29212, Mycobacterium smegmatis ATCC 19420) and Gram-negative (Escherichia coli ATCC 9637, Proteus mirabilis CECT 170, Pseudomonas aeruginosa AK 958, Salmonella sp CECT 4569) bacteria and the yeast Candida albicans CECT 1039. The bacteria cultures were developed in nutrient broth (NB) or brain heart infusion broth (for E. faecalis, and M. smegmatis containing 0.06% Tween 80), and the yeast was cultured in Sabouraud liquid medium at 37 C. All media were purchased from Oxoid. The minimal inhibitory concentration (MIC) was determined for each compound in triplicate, by the broth microdilution method The compounds (Rosmanol) were dissolved in DMSO, and wells with the same proportions of DMSO were used as controls and never exceeded 1% (v/v). The starting microorganism concentration was approximately (1-5) x 10^5 cfu/mL, and growth was monitored by measuring the increase in optical density at 550 nm (OD550) with a microplate reader (Multiskan Plus II). All wells with no visible growth after 24 h, except for M. smegmatis (48 h), in a rotatory shaker at 37 C were subcultured by transferring in duplicate (0.1 mL) to nutrient, brain heart infusion, or Sabouraud agar plates. After overnight incubation, colony counts were performed and the MIC was defined as the lowest concentration of compound at which growth was inhibited after 24 h of incubation.
Name Type Language
ROSMANOL
Common Name English
2H-10,4A-(EPOXYMETHANO)PHENANTHREN-12-ONE, 1,3,4,9,10,10A-HEXAHYDRO-5,6,9-TRIHYDROXY-1,1-DIMETHYL-7-(1-METHYLETHYL)-, (4AR-(4A.ALPHA.,9.BETA.,10.ALPHA.,10A.BETA.))-
Systematic Name English
2H-10,4A-(EPOXYMETHANO)PHENANTHREN-12-ONE, 1,3,4,9,10,10A-HEXAHYDRO-5,6,9-TRIHYDROXY-1,1-DIMETHYL-7-(1-METHYLETHYL)-, (4AR,9S,10S,10AS)-
Systematic Name English
Code System Code Type Description
CAS
80225-53-2
Created by admin on Sat Dec 16 09:29:42 GMT 2023 , Edited by admin on Sat Dec 16 09:29:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID80553423
Created by admin on Sat Dec 16 09:29:42 GMT 2023 , Edited by admin on Sat Dec 16 09:29:42 GMT 2023
PRIMARY
PUBCHEM
13966122
Created by admin on Sat Dec 16 09:29:42 GMT 2023 , Edited by admin on Sat Dec 16 09:29:42 GMT 2023
PRIMARY
CAS
33985-86-3
Created by admin on Sat Dec 16 09:29:42 GMT 2023 , Edited by admin on Sat Dec 16 09:29:42 GMT 2023
SUPERSEDED
FDA UNII
F25TV383OC
Created by admin on Sat Dec 16 09:29:42 GMT 2023 , Edited by admin on Sat Dec 16 09:29:42 GMT 2023
PRIMARY