Yashabushidiol A

Two-Pot Synthesis of Chiral 1,3-syn-Diols through Asymmetric Organocatalytic Aldol and Wittig Reactions Followed by Domino Hemiacetal/Oxy-Michael Reactions.[Pubmed:29322570]

Chemistry. 2018 Apr 3;24(19):4909-4915.

A two-pot synthetic method to construct the chiral syn-1,3-diol unit has been developed from three aldehydes and either Wittig or Horner-Wadsworth-Emmons reagents. In the first pot, chiral delta-hydroxy alpha,beta-unsaturated ketones are synthesized with excellent enantioselectivity by the organocatalyst-mediated asymmetric direct aldol reaction of two different aldehydes, followed by either Wittig or Horner-Wadsworth-Emmons reactions. In the second pot, domino acetalization with an aldehyde and subsequent oxy-Michael reaction proceeds in the presence of NaClO4 and a catalytic amount of Bi(OTf)3 (OTf=trifluoromethanesulfonate) to provide the chiral 1,3-syn-diol derivative with excellent diastereoselectivity. Diospongin C and Yashabushidiol A have been synthesized efficiently by using the present method as a key step.

Interactions of Desmethoxyyangonin, a Secondary Metabolite from Renealmia alpinia, with Human Monoamine Oxidase-A and Oxidase-B.[Pubmed:29138643]

Evid Based Complement Alternat Med. 2017;2017:4018724.

Renealmia alpinia (Zingiberaceae), a medicinal plant of tropical rainforests, is used to treat snakebites and other injuries and also as a febrifuge, analgesic, antiemetic, antiulcer, and anticonvulsant. The dichloromethane extract of R. alpinia leaves showed potent inhibition of human monoamine oxidases- (MAOs-) A and B. Phytochemical studies yielded six known compounds, including pinostrobin 1, 4'-methyl ether sakuranetin 2, sakuranetin 3, pinostrobin chalcone 4, Yashabushidiol A 5, and desmethoxyyangonin 6. Compound 6 displayed about 30-fold higher affinity for MAO-B than MAO-A, with Ki values of 31 and 922 nM, respectively. Kinetic analysis of inhibition and equilibrium-dialysis dissociation assay of the enzyme-inhibitor complex showed reversible binding of desmethoxyyangonin 6 with MAO-A and MAO-B. The binding interactions of compound 6 in the active site of the MAO-A and MAO-B isoenzymes, investigated through molecular modeling algorithms, confirmed preferential binding of desmethoxyyangonin 6 with MAO-B compared to MAO-A. Selective reversible inhibitors of MAO-B, like desmethoxyyangonin 6, may have important therapeutic significance for the treatment of neurodegenerative disorders, such as Parkinson's disease and Alzheimer's disease.

Constituents of Fermented Male Flowers of Alnus sieboldiana (Betulaceae).[Pubmed:30549825]

Nat Prod Commun. 2017 Jan;12(1):57-58.

Fractionation of the ethyl acetate crude extract of the fermented male flowers of Alnus sieboldiana resulted in the isolation of two diaryiheptanoids and six flavonoids. Yashabushidiol A, yashabushidiol B and naringenin were known constituents of the male flowers of A. sieboldiana while kaenipferol, quercetin, pinocembrin dimethyl ether, 5,7-dimethoxy-3-hydroxyflavanone and 5,7-dimethoxy-3-hydroxyflavone were isolated for first time from the fermented mile flowers of A. sieboldiana. The isolated compounds were characterized using NMR and HRMS and compared with available literature. -.

Synthesis of yashabushidiol and its analogues and their cytotoxic activity against cancer cell lines.[Pubmed:19410455]

Bioorg Med Chem Lett. 2009 Jun 1;19(11):3125-7.

A total synthesis of yashabushidiol (1a), a linear diarylheptanoid having 1,3- diol system and its analogues has been achieved by alkynylation of 3-hydroxy-5-phenyl pentanal with substituted phenyl acetylenes. All the compounds have shown significant anti-proliferative activity on human leukemia (THP-1, U-937) and melanoma (A-375) cell lines. Compounds 2a and 2b were found to be most potent with an IC(50) of 12.82 microg/mL and 12.62 microg/mL, respectively, on THP-1 leukemia cell line.