Linderatin

Linderatin

Identifiers
IUPAC name 3-Phenyl-1-[2,4,6-trihydroxy-3-(3-methyl-6-propan-2-ylcyclohex-2-en-1-yl)phenyl]propan-1-one
PubChem CID	353260
ChemSpider	10258971
Chemical and physical data
Formula	C25H30O4
Molar mass	394.511 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(C(CC1)C(C)C)C2=C(C(=C(C=C2O)O)C(=O)CCC3=CC=CC=C3)O
InChI InChI=1S/C25H30O4/c1-15(2)18-11-9-16(3)13-19(18)23-21(27)14-22(28)24(25(23)29)20(26)12-10-17-7-5-4-6-8-17/h4-8,13-15,18-19,27-29H,9-12H2,1-3H3 Key:GHISAUFWVUOBIR-UHFFFAOYSA-N

Linderatin is a naturally occurring meroterpene compound first isolated from the leaves of Lindera umbellata , a plant known for its aromatic and medicinal properties within the Lauraceae family. ^{[1] [2] [3] [4]}

Structurally, linderatin is classified as a dihydrochalcone derivative, featuring a unique combination of phenolic and terpenoid elements. ^{[1] [5]} The compound has also been identified in other plant species, such as Piper aduncum, and is notable for its rarity among naturally occurring phytochemicals. While Linderatin is closely related to cannabidiol (CBD) in structure, it is not considered a phytocannabinoid, and its biological activities are still under investigation. ^[2] Synthetic routes for Linderatin have been developed, further enabling the exploration of its potential pharmacological applications, including reported cytotoxic activity against certain cancer cell lines. ^[5]

Synthesis

The Hoesch reaction between hydrocinnamonitrile (2-phenylethylcyanide; 1) with phloroglucinol (2) gives 3-phenylpropanoyl-phloroglucinol (3). Treatment with menthadiene (alpha-phellandrene; 4) completes the synthesis of linderatin (5). ^{[6] [7]}

See also

• Cannabidiol
• Flopropione

References

1. "Linderatin". PubMed. U.S. National Library of Medicine.
2. Morales P, Reggio PH, Jagerovic N (2017). "An Overview on Medicinal Chemistry of Synthetic and Natural Derivatives of Cannabidiol". Frontiers in Pharmacology. 8 422. doi: 10.3389/fphar.2017.00422 . PMC   5487438 . PMID   28701957.
3. Ichino K, Tanaka H, Ito K (November 1988). "ChemInform Abstract: Two Novel Flavonoids from the Leaves of Lindera umbellata var. lancea and L. umbellata". ChemInform. 19 (44) chin.198844339. doi:10.1002/chin.198844339.
4. Tanaka H, Ichino K, Ito K (1984). "A novel dihydrochalcone, linderatin from Lindera umbellata var. lancea". Chemical and Pharmaceutical Bulletin. 32 (9): 3747–3750. doi: 10.1248/cpb.32.3747 .
5. Crombie L, Crombie WM, Firth DF (1988). "Terpenylations using (R)-(–)-α-phellandrene. Synthesis of the (3 S, 4 R)-8, 9-dihydro-o-and-p-cannabidiols, their iso-THC's, and the natural dihydrochalcone (3 S, 4 R)-(+)-linderatin". Journal of the Chemical Society, Perkin Transactions 1 (5): 1251–1253. doi:10.1039/P19880001251.
6. Mustafa K, Kjaergaard HG, Perry NB, Weavers RT (August 2003). "Hydrogen-bonded rotamers of 2′,4′,6′-trihydroxy-3′-formyldihydrochalcone, an intermediate in the synthesis of a dihydrochalcone from Leptospermum recurvum". Tetrahedron. 59 (32): 6113–6120. doi:10.1016/S0040-4020(03)00940-2.
7. Crombie L, Crombie WM, Firth DF (1988). "Terpenylations using (R)-(–)-α-phellandrene. Synthesis of the (3S,4R)-8,9-dihydro-o- and -p-cannabidiols, their iso-THC's, and the natural dihydrochalcone (3S,4R)-(+)-linderatin". J. Chem. Soc., Perkin Trans. 1 (5): 1251–1253. doi:10.1039/P19880001251.