Terpenylated coumarins as SIRT1 activators isolated from ailanthus altissima

Trong Tuan Dao, Tien Lam Tran, Jayeon Kim, Phi Hung Nguyen, Eun Hee Lee, Junsoo Park, Ik Soon Jang, Won Keun Oh

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Four new terpenylated coumarins (1-4) were isolated from the stem bark of Ailanthus altissima by bioactivity-guided fractionation using an in vitro SIRT1 deacetylation assay. Their structures were identified as (2′R,3′R)- 7-(2′,3′-dihydroxy-3′,7′-dimethylocta-6′-enyloxy) -6,8-dimethoxycoumarin (1), 6,8-dimethoxy-7-(3′,7′-dimethylocta- 2′,6′-dienyloxy)coumarin (2), (2′R,3′R,6′R)-7- (2′,3′-dihydroxy-6′,7′-epoxy-3′, 7′-dimethyloctaoxy)-6,8-dimethoxycoumarin (3), and (2′R,3′R, 4′S,5′S)-6,8-dimethoxy-7-(3′,7′-dimethyl-4′, 5′-epoxy-2′-hydroxyocta-6′-enyloxy)coumarin (4). Compounds 1-4 strongly enhanced SIRT1 activity in an in vitro SIRT1-NAD/NADH assay and an in vivo SIRT1-p53 luciferase assay. These compounds also increased the NAD-to-NADH ratio in HEK293 cells. The present results suggest that terpenylated coumarins from A. altissima have a direct stimulatory effect on SIRT1 deacetylation activity and may serve as lead molecules for the treatment of some age-related disorders.

Original languageEnglish
Pages (from-to)1332-1338
Number of pages7
JournalJournal of Natural Products
Volume75
Issue number7
DOIs
Publication statusPublished - 2012 Jul 27

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Ailanthus
Coumarins
NAD
Assays
HEK293 Cells
Fractionation
Bioactivity
Luciferases
Molecules

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Dao, T. T., Tran, T. L., Kim, J., Nguyen, P. H., Lee, E. H., Park, J., ... Oh, W. K. (2012). Terpenylated coumarins as SIRT1 activators isolated from ailanthus altissima. Journal of Natural Products, 75(7), 1332-1338. https://doi.org/10.1021/np300258u
Dao, Trong Tuan ; Tran, Tien Lam ; Kim, Jayeon ; Nguyen, Phi Hung ; Lee, Eun Hee ; Park, Junsoo ; Jang, Ik Soon ; Oh, Won Keun. / Terpenylated coumarins as SIRT1 activators isolated from ailanthus altissima. In: Journal of Natural Products. 2012 ; Vol. 75, No. 7. pp. 1332-1338.
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abstract = "Four new terpenylated coumarins (1-4) were isolated from the stem bark of Ailanthus altissima by bioactivity-guided fractionation using an in vitro SIRT1 deacetylation assay. Their structures were identified as (2′R,3′R)- 7-(2′,3′-dihydroxy-3′,7′-dimethylocta-6′-enyloxy) -6,8-dimethoxycoumarin (1), 6,8-dimethoxy-7-(3′,7′-dimethylocta- 2′,6′-dienyloxy)coumarin (2), (2′R,3′R,6′R)-7- (2′,3′-dihydroxy-6′,7′-epoxy-3′, 7′-dimethyloctaoxy)-6,8-dimethoxycoumarin (3), and (2′R,3′R, 4′S,5′S)-6,8-dimethoxy-7-(3′,7′-dimethyl-4′, 5′-epoxy-2′-hydroxyocta-6′-enyloxy)coumarin (4). Compounds 1-4 strongly enhanced SIRT1 activity in an in vitro SIRT1-NAD/NADH assay and an in vivo SIRT1-p53 luciferase assay. These compounds also increased the NAD-to-NADH ratio in HEK293 cells. The present results suggest that terpenylated coumarins from A. altissima have a direct stimulatory effect on SIRT1 deacetylation activity and may serve as lead molecules for the treatment of some age-related disorders.",
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Dao, TT, Tran, TL, Kim, J, Nguyen, PH, Lee, EH, Park, J, Jang, IS & Oh, WK 2012, 'Terpenylated coumarins as SIRT1 activators isolated from ailanthus altissima', Journal of Natural Products, vol. 75, no. 7, pp. 1332-1338. https://doi.org/10.1021/np300258u

Terpenylated coumarins as SIRT1 activators isolated from ailanthus altissima. / Dao, Trong Tuan; Tran, Tien Lam; Kim, Jayeon; Nguyen, Phi Hung; Lee, Eun Hee; Park, Junsoo; Jang, Ik Soon; Oh, Won Keun.

In: Journal of Natural Products, Vol. 75, No. 7, 27.07.2012, p. 1332-1338.

Research output: Contribution to journalArticle

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AU - Dao, Trong Tuan

AU - Tran, Tien Lam

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AU - Park, Junsoo

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AU - Oh, Won Keun

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