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Flavonostilbenes Isolated from the Stems of Rhamnoneuron balansae as Potential SIRT1 Activators
The cumulative effects of cell damage result in aging, which gradually decreases human function in various aspects and leads to multiple age-related chronic diseases. To overcome the adverse effects of aging, silent mating type information regulation 2 homologue (SIRT1) activators are promising bioa...
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Published in: | Journal of natural products (Washington, D.C.) D.C.), 2022-01, Vol.85 (1), p.70-82 |
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container_title | Journal of natural products (Washington, D.C.) |
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creator | Cho, Hyo-Moon Zhang, Mi Park, Eun-Jin Lee, Ba-Wool Park, Yeon-Joo Kim, Hyun-Woo Pham, Ha-Thanh-Tung Chin, Young-Won Oh, Won-Keun |
description | The cumulative effects of cell damage result in aging, which gradually decreases human function in various aspects and leads to multiple age-related chronic diseases. To overcome the adverse effects of aging, silent mating type information regulation 2 homologue (SIRT1) activators are promising bioactive compounds that mimic calorie restriction to improve quality of life and prevent aging. In this study, 11 new flavonostilbenes (1–11) and three known compounds (12–14) were purified from stems of Rhamnoneuron balansae. The structures of the new compounds were determined using extensive data from spectroscopic methods, including NMR and HRESIMS. Their absolute configurations were deduced by ECD calculations with coupling constant analysis. All of the isolated new compounds (1–11) were evaluated for their effects on SIRT1 deacetylase activity, the NAD+/NADH ratio, and the AMP-activated protein kinase activation level in cell-based assays. The results showed that rhamnoneuronal D (1) exhibits promising biological activity in several in vitro models related to SIRT1 and suggest it is a potential natural-product-based antiaging agent. |
doi_str_mv | 10.1021/acs.jnatprod.1c00689 |
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To overcome the adverse effects of aging, silent mating type information regulation 2 homologue (SIRT1) activators are promising bioactive compounds that mimic calorie restriction to improve quality of life and prevent aging. In this study, 11 new flavonostilbenes (1–11) and three known compounds (12–14) were purified from stems of Rhamnoneuron balansae. The structures of the new compounds were determined using extensive data from spectroscopic methods, including NMR and HRESIMS. Their absolute configurations were deduced by ECD calculations with coupling constant analysis. All of the isolated new compounds (1–11) were evaluated for their effects on SIRT1 deacetylase activity, the NAD+/NADH ratio, and the AMP-activated protein kinase activation level in cell-based assays. 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The results showed that rhamnoneuronal D (1) exhibits promising biological activity in several in vitro models related to SIRT1 and suggest it is a potential natural-product-based antiaging agent.</description><subject>Adenylate Kinase - metabolism</subject><subject>Animals</subject><subject>Carbon-13 Magnetic Resonance Spectroscopy</subject><subject>Enzyme Activation</subject><subject>Humans</subject><subject>NAD - metabolism</subject><subject>Plant Stems - chemistry</subject><subject>Proton Magnetic Resonance Spectroscopy</subject><subject>Sirtuin 1 - drug effects</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Stilbenes - isolation & purification</subject><subject>Stilbenes - pharmacology</subject><subject>Thymelaeaceae - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LxDAQhoMoun78A5EcvXSdSZq0PYr4sSAouveQzU6x0iaapIL_3uquHj3N5XnfmXkYO0WYIwi8sC7NX73NbzGs5-gAdN3ssBkqAYUGoXbZDFDLQta6PGCHKb0CgIRG7bMDqaAEiWrGzE1vP4IPKXf9ijwlvkiht5nWvI1h4PmF-HOmIfHQ8qcXO_jgaYzB85XtrU-WuE38MWTyubM9f148LZFfutx92BxiOmZ7re0TnWznEVveXC-v7or7h9vF1eV9YWVZ56LRNVU1VFphuRIKVVNj1ZStrVQtKimcqEvtlKywbBtcCyAkQc6BqqpWgjxi55vaycb7SCmboUuO-ulECmMyQgsEbLDRE1puUBdDSpFa8xa7wcZPg2C-zZrJrPk1a7Zmp9jZdsO4Gmj9F_pVOQGwAX7iYYx--vf_zi_Wy4ds</recordid><startdate>20220128</startdate><enddate>20220128</enddate><creator>Cho, Hyo-Moon</creator><creator>Zhang, Mi</creator><creator>Park, Eun-Jin</creator><creator>Lee, Ba-Wool</creator><creator>Park, Yeon-Joo</creator><creator>Kim, Hyun-Woo</creator><creator>Pham, Ha-Thanh-Tung</creator><creator>Chin, Young-Won</creator><creator>Oh, Won-Keun</creator><general>American Chemical Society and American Society of Pharmacognosy</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3447-8726</orcidid><orcidid>https://orcid.org/0000-0002-4944-5145</orcidid><orcidid>https://orcid.org/0000-0003-0761-3064</orcidid><orcidid>https://orcid.org/0000-0003-2473-8360</orcidid></search><sort><creationdate>20220128</creationdate><title>Flavonostilbenes Isolated from the Stems of Rhamnoneuron balansae as Potential SIRT1 Activators</title><author>Cho, Hyo-Moon ; Zhang, Mi ; Park, Eun-Jin ; Lee, Ba-Wool ; Park, Yeon-Joo ; Kim, Hyun-Woo ; Pham, Ha-Thanh-Tung ; Chin, Young-Won ; Oh, Won-Keun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-968e78076514b2515981794fa7582732c2846c53714f91d20e1e2ecc0577f303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Adenylate Kinase - metabolism</topic><topic>Animals</topic><topic>Carbon-13 Magnetic Resonance Spectroscopy</topic><topic>Enzyme Activation</topic><topic>Humans</topic><topic>NAD - metabolism</topic><topic>Plant Stems - chemistry</topic><topic>Proton Magnetic Resonance Spectroscopy</topic><topic>Sirtuin 1 - drug effects</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Stilbenes - isolation & purification</topic><topic>Stilbenes - pharmacology</topic><topic>Thymelaeaceae - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cho, Hyo-Moon</creatorcontrib><creatorcontrib>Zhang, Mi</creatorcontrib><creatorcontrib>Park, Eun-Jin</creatorcontrib><creatorcontrib>Lee, Ba-Wool</creatorcontrib><creatorcontrib>Park, Yeon-Joo</creatorcontrib><creatorcontrib>Kim, Hyun-Woo</creatorcontrib><creatorcontrib>Pham, Ha-Thanh-Tung</creatorcontrib><creatorcontrib>Chin, Young-Won</creatorcontrib><creatorcontrib>Oh, Won-Keun</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cho, Hyo-Moon</au><au>Zhang, Mi</au><au>Park, Eun-Jin</au><au>Lee, Ba-Wool</au><au>Park, Yeon-Joo</au><au>Kim, Hyun-Woo</au><au>Pham, Ha-Thanh-Tung</au><au>Chin, Young-Won</au><au>Oh, Won-Keun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Flavonostilbenes Isolated from the Stems of Rhamnoneuron balansae as Potential SIRT1 Activators</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. 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subjects | Adenylate Kinase - metabolism Animals Carbon-13 Magnetic Resonance Spectroscopy Enzyme Activation Humans NAD - metabolism Plant Stems - chemistry Proton Magnetic Resonance Spectroscopy Sirtuin 1 - drug effects Spectrometry, Mass, Electrospray Ionization Stilbenes - isolation & purification Stilbenes - pharmacology Thymelaeaceae - chemistry |
title | Flavonostilbenes Isolated from the Stems of Rhamnoneuron balansae as Potential SIRT1 Activators |
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