(+)-LARICIRESINOL
(+)-LARICIRESINOL Basic information
- Product Name:
- (+)-LARICIRESINOL
- Synonyms:
-
- (2S)-2α-(3-Methoxy-4-hydroxyphenyl)-4β-(3-methoxy-4-hydroxybenzyl)tetrahydrofuran-3β-methanol
- (2S)-Tetrahydro-2α-(4-hydroxy-3-methoxyphenyl)-4β-[(4-hydroxy-3-methoxyphenyl)methyl]-3β-furanmethanol
- 2-Methoxy-4-[[(2S)-tetrahydro-2α-(3-methoxy-4-hydroxyphenyl)-3β-(hydroxymethyl)furan-4β-yl]methyl]phenol
- 2α-(4-Hydroxy-3-methoxyphenyl)-3β-(hydroxymethyl)-4β-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran
- Laricericinol
- Nsc329247
- Lariciresil
- (+)-LARICIRESINOL
- CAS:
- 27003-73-2
- MF:
- C20H24O6
- MW:
- 360.4
- Product Categories:
-
- Miscellaneous Natural Products
- Mol File:
- 27003-73-2.mol
(+)-LARICIRESINOL Chemical Properties
- Melting point:
- 167-168 °C
- Boiling point:
- 568.4±50.0 °C(Predicted)
- Density
- 1.261±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Powder
- pka
- 9.91±0.35(Predicted)
- color
- White to off-white
- BRN
- 4560057
- InChI
- InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m0/s1
- InChIKey
- MHXCIKYXNYCMHY-AUSJPIAWSA-N
- SMILES
- O1C[C@H](CC2=CC=C(O)C(OC)=C2)[C@H](CO)[C@H]1C1=CC=C(O)C(OC)=C1
- LogP
- 1.640 (est)
(+)-LARICIRESINOL Usage And Synthesis
Uses
(+)-Lariciresinol is used in biological studies as an anti-tumor-initiating effects of phenolic compounds isolated from the bark of Picea jezoensis var. jezoensis to evaluate the pharmacological activity.
Definition
ChEBI: (+)-lariciresinol is a lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). It has a role as an antifungal agent and a plant metabolite. It is a member of oxolanes, a member of phenols, a lignan, a primary alcohol and an aromatic ether. It is an enantiomer of a (-)-lariciresinol.
Biological Activity
Lariciresinol is a potent dietary antioxidant and a radical scavenger by potentially chelating catalytic Fe2+ ions. It exerts antimicrobial effects against foodborne pathogens S. aureus and E. coli O157:H7. Lariciresinol is an effective anticancer agent th at inhibits cell proliferation and induces apoptosis in human HepG2 cells in vitro. It also displays anti-inflammatory and anti-diabetic effects in vitro and in vivo studies respectively.
in vivo
Lariciresinol (10 mg/kg, p.o., 3 weeks) displays anti-diabetic activity in Streptozotocin (HY-13753)-treated diabetic mice[6].
Lariciresinol (10-30 mg/kg, i.p., 28 days) inhibits complete Freund's adjuvant-induced arthritis in rats by regulating TGF-β and NF-κB pathways[7].
Lariciresinol (3-15 mg/kg body weight, p.o., daily, 9 weeks (tumor bearing rats); 20-100 ppm, diet, p.o., 5 weeks (E2-maintained ovariectomized athymic mice bearing orthotopic MCF-7 tumors)) inhibits tumor growth and tumor angiogenesis in mammary tumor bearing rats and E2-maintained ovariectomized athymic mice bearing orthotopic MCF-7 tumors[8].
| Animal Model: | Streptozotocin (HY-13753)-treated diabetic mice[6] |
| Dosage: | 10 mg/kg |
| Administration: | Oral gavage (p.o.), 3 weeks |
| Result: | Decreased blood glucose levels and increased insulin levels. Improved pancreatic islet size, increased GLUT4 expression. Enhanced insulin signaling in skeletal muscle. |
target
VEGFR | Antifection
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