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Honokiol dimers and magnolol derivatives with new carbon skeletons from the roots of Magnolia officinalis and their inhibitory effects on superoxide anion generation and elastase release.

Shih HC, Hwang TL, Chen HC, Kuo PC, Lee EJ, Lee KH, Wu TS - PLoS ONE (2013)

Bottom Line: Two honokiol dimers, houpulins A and B (1 and 2), and two magnolol derivatives, houpulins C and D (3 and 4), were isolated and characterized from an ethanol extract obtained from the roots of Magnolia officinalis.These four oligomers possess new carbon skeletons postulated to be biosynthesized from the coupling of three or four C6-C3 subunits.In addition, the new oligomers were evaluated for inhibition of superoxide anion generation and elastase release, and houpulin B (2) was identified as a new anti-inflammatory lead compound.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, National Cheng Kung University, Tainan, Taiwan.

ABSTRACT
Two honokiol dimers, houpulins A and B (1 and 2), and two magnolol derivatives, houpulins C and D (3 and 4), were isolated and characterized from an ethanol extract obtained from the roots of Magnolia officinalis. The chemical structures were determined based on spectroscopic and physicochemical analyses, which included 1D and 2D NMR, as well as mass spectrometry data. These four oligomers possess new carbon skeletons postulated to be biosynthesized from the coupling of three or four C6-C3 subunits. In addition, the new oligomers were evaluated for inhibition of superoxide anion generation and elastase release, and houpulin B (2) was identified as a new anti-inflammatory lead compound.

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Related in: MedlinePlus

Plausible biosynthetic pathway to 1 and 2.
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pone-0059502-g002: Plausible biosynthetic pathway to 1 and 2.

Mentions: Figure 2 depicts our proposed biogenetic pathway to compounds 1 and 2, with the compounds being derived by bimolecular coupling between two honokiol radical derivatives. Because the radical intermediate would be more stable if the radical was located at the ortho-position to the hydroxy group, the major honokiol radical intermediates are 5 and 6, and the resultant coupling products are compounds 1 and 2, which exhibit the new carbon skeletons characterized in the present work.


Honokiol dimers and magnolol derivatives with new carbon skeletons from the roots of Magnolia officinalis and their inhibitory effects on superoxide anion generation and elastase release.

Shih HC, Hwang TL, Chen HC, Kuo PC, Lee EJ, Lee KH, Wu TS - PLoS ONE (2013)

Plausible biosynthetic pathway to 1 and 2.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3646836&req=5

pone-0059502-g002: Plausible biosynthetic pathway to 1 and 2.
Mentions: Figure 2 depicts our proposed biogenetic pathway to compounds 1 and 2, with the compounds being derived by bimolecular coupling between two honokiol radical derivatives. Because the radical intermediate would be more stable if the radical was located at the ortho-position to the hydroxy group, the major honokiol radical intermediates are 5 and 6, and the resultant coupling products are compounds 1 and 2, which exhibit the new carbon skeletons characterized in the present work.

Bottom Line: Two honokiol dimers, houpulins A and B (1 and 2), and two magnolol derivatives, houpulins C and D (3 and 4), were isolated and characterized from an ethanol extract obtained from the roots of Magnolia officinalis.These four oligomers possess new carbon skeletons postulated to be biosynthesized from the coupling of three or four C6-C3 subunits.In addition, the new oligomers were evaluated for inhibition of superoxide anion generation and elastase release, and houpulin B (2) was identified as a new anti-inflammatory lead compound.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, National Cheng Kung University, Tainan, Taiwan.

ABSTRACT
Two honokiol dimers, houpulins A and B (1 and 2), and two magnolol derivatives, houpulins C and D (3 and 4), were isolated and characterized from an ethanol extract obtained from the roots of Magnolia officinalis. The chemical structures were determined based on spectroscopic and physicochemical analyses, which included 1D and 2D NMR, as well as mass spectrometry data. These four oligomers possess new carbon skeletons postulated to be biosynthesized from the coupling of three or four C6-C3 subunits. In addition, the new oligomers were evaluated for inhibition of superoxide anion generation and elastase release, and houpulin B (2) was identified as a new anti-inflammatory lead compound.

Show MeSH
Related in: MedlinePlus