New Synthetic Routes to Biologically Interesting Geranylated Acetophenones from Melicope Semecarpifolia and Their Unnatural Prenylated and Farnesylated Derivatives

Xia, Likai; Narasimhulu, M.; Li, Xin; Shim, Jae‐Jin; Lee, Yong Rok

doi:10.5012/bkcs.2010.31.03.664

Cited by 8 publications

(1 citation statement)

References 29 publications

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“…This compound was givedn the trivial name heliteretifoline. To the best of our knowledge and according to the SciFinder database, compound 1 was only described once as synthetic product but has not been isolated before from a natural source [13]. Isoxanthohumol ( 2 ) and isoglabranin ( 4 ) were isolated previously from H. polycladum [14].…”

Section: Resultsmentioning

confidence: 99%

Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium

et al. 2015

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Ten flavonoid-related structures viz. heliteretifolin (1), isoxanthohumol (2), 2',4',6'-trihydroxy-3'-prenylchalcone (3), isoglabranin (4), glabranin (5), 7-methoxy-isoglabranin (6), quercetin (7), 4'-methoxyquercetin (8), 4'-methoxykaempferol (9) and mosloflavone (10) were isolated from a H. teretifolium methanolic extract and identified. One of them (compound 1) is reported for the first time from a natural source, while compounds 6, 8–10 were isolated for the first time from the genus Helichrysum. The total extract of H. teretifolium showed potent antioxidant activity. When tested for total antioxidant capacity compound 3 possesses moderate biological activity compared to 2, which displayed some of the highest TEAC values (4529.01 ± 2.44; 4170.66 ± 6.72) µM TE/g, respectively. Compounds 7 and 8 demonstrated the highest inhibitory activities on Fe2+-induced lipid peroxidation (IC50 = 2.931; 6.449 µg/mL); tyrosinase (8.092; 27.573) and elastase (43.342; 86.548). Additionally, the total antioxidant capacities measured as FRAP (4816.31 ± 7.42; 3584.17 ± 0.54) µM AAE/g, and ORAC for hydroxyl radical (7.265 ± 0.71; 6.779 ± 3.40) × 106 and peroxyl radical (17.836 ± 2.90; 12.545 ± 5.07) × 103 µM TE/g were also observed for compounds 7 and 8, respectively. In conclusion, H. teretifolium total extract represents a rich source of bioactive constituents with potent antioxidant and moderate anti-tyrosinase and anti-elastase activities that can help to avert accumulation of free radicals in the body, and could therefore be good candidates for the prevention and/or treatment of skin-related conditions, such as aging. This is the first scientific report on the chemical and biological profile of H. teretifolium.

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Section: Resultsmentioning

confidence: 99%

Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium

et al. 2015

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ChemInform Abstract: New Synthetic Routes to Biologically Interesting Geranylated Acetophenones from Melicope Semecarpifolia and Their Unnatural Prenylated and Farnesylated Derivatives.

Xia

Narasimhulu

et al. 2010

ChemInform

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Rottlerin: Structure Modifications and KCNQ1/KCNE1 Ion Channel Activity

et al. 2020

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The slow delayed rectifier potassium current (IKs) is formed by the KCNQ1 (Kv7.1) channel, an ion channel of four α‐subunits that modulates KCNE1 β‐subunits. IKs is central to the repolarization of the cardiac action potential. Loss of function mutation reducing ventricular cardiac IKs cause the long‐QT syndrome (LQTS), a disorder that predisposes patients to arrhythmia and sudden death. Current therapy for LQTS is inadequate. Rottlerin, a natural product of the kamala tree, activates IKs and has the potential to provide a new strategy for rational drug therapy. In this study, we show that simple modifications such as penta‐acetylation or penta‐methylation of rottlerin blunts activation activity. Total synthesis was used to prepare side‐chain‐modified derivatives that slowed down KCNQ1/KCNE1 channel deactivation to different degrees. A binding hypothesis of rottlerin is provided that opens the way to improved IKs activators as novel therapeutics for the treatment of LQTS.

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New Synthetic Routes to Biologically Interesting Geranylated Acetophenones from Melicope Semecarpifolia and Their Unnatural Prenylated and Farnesylated Derivatives

Cited by 8 publications

References 29 publications

Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium

Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium

ChemInform Abstract: New Synthetic Routes to Biologically Interesting Geranylated Acetophenones from Melicope Semecarpifolia and Their Unnatural Prenylated and Farnesylated Derivatives.

Rottlerin: Structure Modifications and KCNQ1/KCNE1 Ion Channel Activity

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