A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect

<i<Stevia rebaudiana</i< (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natu...
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Autor*in:	Heesun Kang [verfasserIn] Dahae Lee [verfasserIn] Ki Sung Kang [verfasserIn] Ki Hyun Kim [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2022

Schlagwörter:	Asteraceae labdane-type diterpene insulin secretion

Übergeordnetes Werk:	In: Biomedicines - MDPI AG, 2014, 10(2022), 4, p 839
Übergeordnetes Werk:	volume:10 ; year:2022 ; number:4, p 839

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/biomedicines10040839

Katalog-ID:	DOAJ032248105

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allfields	10.3390/biomedicines10040839 doi (DE-627)DOAJ032248105 (DE-599)DOAJ6c5acf47219147d29307936e6d250cd0 DE-627 ger DE-627 rakwb eng QH301-705.5 Heesun Kang verfasserin aut A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Stevia rebaudiana</i< (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natural products, phytochemical investigation of the ethanolic extract of <i<S. rebaudiana</i< leaves led to the isolation of one new labdane-type diterpene, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), and nine known terpenoids, including six diterpenes (<b<2</b<–<b<6</b< and <b<10</b<), two monoterpenes (<b<7</b< and <b<8</b<), and one triterpene (<b<9</b<). The structure of the new compound <b<1</b< was elucidated via analysis of one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry data, and its absolute configuration was established using electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + probability analysis. The isolated compounds <b<1</b<–<b<10</b< were evaluated for their effects on glucose-stimulated insulin secretion in the INS-1 rat pancreatic β-cell line. The new compound <b<1</b<, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane, stimulated glucose-stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. Thus, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), an active compound derived from <i<S. rebaudiana</i< leaves, can be used as a potential therapeutic agent to prevent type 2 diabetes. <i<Stevia rebaudiana</i< Asteraceae labdane-type diterpene insulin secretion Biology (General) Dahae Lee verfasserin aut Ki Sung Kang verfasserin aut Ki Hyun Kim verfasserin aut In Biomedicines MDPI AG, 2014 10(2022), 4, p 839 (DE-627)750370483 (DE-600)2720867-9 22279059 nnns volume:10 year:2022 number:4, p 839 https://doi.org/10.3390/biomedicines10040839 kostenfrei https://doaj.org/article/6c5acf47219147d29307936e6d250cd0 kostenfrei https://www.mdpi.com/2227-9059/10/4/839 kostenfrei https://doaj.org/toc/2227-9059 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2022 4, p 839
spelling	10.3390/biomedicines10040839 doi (DE-627)DOAJ032248105 (DE-599)DOAJ6c5acf47219147d29307936e6d250cd0 DE-627 ger DE-627 rakwb eng QH301-705.5 Heesun Kang verfasserin aut A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Stevia rebaudiana</i< (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natural products, phytochemical investigation of the ethanolic extract of <i<S. rebaudiana</i< leaves led to the isolation of one new labdane-type diterpene, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), and nine known terpenoids, including six diterpenes (<b<2</b<–<b<6</b< and <b<10</b<), two monoterpenes (<b<7</b< and <b<8</b<), and one triterpene (<b<9</b<). The structure of the new compound <b<1</b< was elucidated via analysis of one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry data, and its absolute configuration was established using electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + probability analysis. The isolated compounds <b<1</b<–<b<10</b< were evaluated for their effects on glucose-stimulated insulin secretion in the INS-1 rat pancreatic β-cell line. The new compound <b<1</b<, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane, stimulated glucose-stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. Thus, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), an active compound derived from <i<S. rebaudiana</i< leaves, can be used as a potential therapeutic agent to prevent type 2 diabetes. <i<Stevia rebaudiana</i< Asteraceae labdane-type diterpene insulin secretion Biology (General) Dahae Lee verfasserin aut Ki Sung Kang verfasserin aut Ki Hyun Kim verfasserin aut In Biomedicines MDPI AG, 2014 10(2022), 4, p 839 (DE-627)750370483 (DE-600)2720867-9 22279059 nnns volume:10 year:2022 number:4, p 839 https://doi.org/10.3390/biomedicines10040839 kostenfrei https://doaj.org/article/6c5acf47219147d29307936e6d250cd0 kostenfrei https://www.mdpi.com/2227-9059/10/4/839 kostenfrei https://doaj.org/toc/2227-9059 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2022 4, p 839
allfields_unstemmed	10.3390/biomedicines10040839 doi (DE-627)DOAJ032248105 (DE-599)DOAJ6c5acf47219147d29307936e6d250cd0 DE-627 ger DE-627 rakwb eng QH301-705.5 Heesun Kang verfasserin aut A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Stevia rebaudiana</i< (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natural products, phytochemical investigation of the ethanolic extract of <i<S. rebaudiana</i< leaves led to the isolation of one new labdane-type diterpene, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), and nine known terpenoids, including six diterpenes (<b<2</b<–<b<6</b< and <b<10</b<), two monoterpenes (<b<7</b< and <b<8</b<), and one triterpene (<b<9</b<). The structure of the new compound <b<1</b< was elucidated via analysis of one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry data, and its absolute configuration was established using electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + probability analysis. The isolated compounds <b<1</b<–<b<10</b< were evaluated for their effects on glucose-stimulated insulin secretion in the INS-1 rat pancreatic β-cell line. The new compound <b<1</b<, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane, stimulated glucose-stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. Thus, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), an active compound derived from <i<S. rebaudiana</i< leaves, can be used as a potential therapeutic agent to prevent type 2 diabetes. <i<Stevia rebaudiana</i< Asteraceae labdane-type diterpene insulin secretion Biology (General) Dahae Lee verfasserin aut Ki Sung Kang verfasserin aut Ki Hyun Kim verfasserin aut In Biomedicines MDPI AG, 2014 10(2022), 4, p 839 (DE-627)750370483 (DE-600)2720867-9 22279059 nnns volume:10 year:2022 number:4, p 839 https://doi.org/10.3390/biomedicines10040839 kostenfrei https://doaj.org/article/6c5acf47219147d29307936e6d250cd0 kostenfrei https://www.mdpi.com/2227-9059/10/4/839 kostenfrei https://doaj.org/toc/2227-9059 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2022 4, p 839
allfieldsGer	10.3390/biomedicines10040839 doi (DE-627)DOAJ032248105 (DE-599)DOAJ6c5acf47219147d29307936e6d250cd0 DE-627 ger DE-627 rakwb eng QH301-705.5 Heesun Kang verfasserin aut A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Stevia rebaudiana</i< (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natural products, phytochemical investigation of the ethanolic extract of <i<S. rebaudiana</i< leaves led to the isolation of one new labdane-type diterpene, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), and nine known terpenoids, including six diterpenes (<b<2</b<–<b<6</b< and <b<10</b<), two monoterpenes (<b<7</b< and <b<8</b<), and one triterpene (<b<9</b<). The structure of the new compound <b<1</b< was elucidated via analysis of one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry data, and its absolute configuration was established using electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + probability analysis. The isolated compounds <b<1</b<–<b<10</b< were evaluated for their effects on glucose-stimulated insulin secretion in the INS-1 rat pancreatic β-cell line. The new compound <b<1</b<, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane, stimulated glucose-stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. Thus, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), an active compound derived from <i<S. rebaudiana</i< leaves, can be used as a potential therapeutic agent to prevent type 2 diabetes. <i<Stevia rebaudiana</i< Asteraceae labdane-type diterpene insulin secretion Biology (General) Dahae Lee verfasserin aut Ki Sung Kang verfasserin aut Ki Hyun Kim verfasserin aut In Biomedicines MDPI AG, 2014 10(2022), 4, p 839 (DE-627)750370483 (DE-600)2720867-9 22279059 nnns volume:10 year:2022 number:4, p 839 https://doi.org/10.3390/biomedicines10040839 kostenfrei https://doaj.org/article/6c5acf47219147d29307936e6d250cd0 kostenfrei https://www.mdpi.com/2227-9059/10/4/839 kostenfrei https://doaj.org/toc/2227-9059 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2022 4, p 839
allfieldsSound	10.3390/biomedicines10040839 doi (DE-627)DOAJ032248105 (DE-599)DOAJ6c5acf47219147d29307936e6d250cd0 DE-627 ger DE-627 rakwb eng QH301-705.5 Heesun Kang verfasserin aut A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect 2022 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier <i<Stevia rebaudiana</i< (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natural products, phytochemical investigation of the ethanolic extract of <i<S. rebaudiana</i< leaves led to the isolation of one new labdane-type diterpene, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), and nine known terpenoids, including six diterpenes (<b<2</b<–<b<6</b< and <b<10</b<), two monoterpenes (<b<7</b< and <b<8</b<), and one triterpene (<b<9</b<). The structure of the new compound <b<1</b< was elucidated via analysis of one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry data, and its absolute configuration was established using electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + probability analysis. The isolated compounds <b<1</b<–<b<10</b< were evaluated for their effects on glucose-stimulated insulin secretion in the INS-1 rat pancreatic β-cell line. The new compound <b<1</b<, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane, stimulated glucose-stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. Thus, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), an active compound derived from <i<S. rebaudiana</i< leaves, can be used as a potential therapeutic agent to prevent type 2 diabetes. <i<Stevia rebaudiana</i< Asteraceae labdane-type diterpene insulin secretion Biology (General) Dahae Lee verfasserin aut Ki Sung Kang verfasserin aut Ki Hyun Kim verfasserin aut In Biomedicines MDPI AG, 2014 10(2022), 4, p 839 (DE-627)750370483 (DE-600)2720867-9 22279059 nnns volume:10 year:2022 number:4, p 839 https://doi.org/10.3390/biomedicines10040839 kostenfrei https://doaj.org/article/6c5acf47219147d29307936e6d250cd0 kostenfrei https://www.mdpi.com/2227-9059/10/4/839 kostenfrei https://doaj.org/toc/2227-9059 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 10 2022 4, p 839
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source	In Biomedicines 10(2022), 4, p 839 volume:10 year:2022 number:4, p 839
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spellingShingle	Heesun Kang misc QH301-705.5 misc <i<Stevia rebaudiana</i< misc Asteraceae misc labdane-type diterpene misc insulin secretion misc Biology (General) A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect
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topic_title	QH301-705.5 A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect <i<Stevia rebaudiana</i< Asteraceae labdane-type diterpene insulin secretion
topic	misc QH301-705.5 misc <i<Stevia rebaudiana</i< misc Asteraceae misc labdane-type diterpene misc insulin secretion misc Biology (General)
topic_unstemmed	misc QH301-705.5 misc <i<Stevia rebaudiana</i< misc Asteraceae misc labdane-type diterpene misc insulin secretion misc Biology (General)
topic_browse	misc QH301-705.5 misc <i<Stevia rebaudiana</i< misc Asteraceae misc labdane-type diterpene misc insulin secretion misc Biology (General)
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title	A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect
ctrlnum	(DE-627)DOAJ032248105 (DE-599)DOAJ6c5acf47219147d29307936e6d250cd0
title_full	A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect
author_sort	Heesun Kang
journal	Biomedicines
journalStr	Biomedicines
callnumber-first-code	Q
lang_code	eng
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publishDateSort	2022
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author_browse	Heesun Kang Dahae Lee Ki Sung Kang Ki Hyun Kim
container_volume	10
class	QH301-705.5
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author-letter	Heesun Kang
doi_str_mv	10.3390/biomedicines10040839
author2-role	verfasserin
title_sort	new labdane-type diterpene, 6-<i<o</i<-acetyl-(12<i<r</i<)-epiblumdane, from <i<stevia rebaudiana</i< leaves with insulin secretion effect
callnumber	QH301-705.5
title_auth	A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect
abstract	<i<Stevia rebaudiana</i< (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natural products, phytochemical investigation of the ethanolic extract of <i<S. rebaudiana</i< leaves led to the isolation of one new labdane-type diterpene, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), and nine known terpenoids, including six diterpenes (<b<2</b<–<b<6</b< and <b<10</b<), two monoterpenes (<b<7</b< and <b<8</b<), and one triterpene (<b<9</b<). The structure of the new compound <b<1</b< was elucidated via analysis of one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry data, and its absolute configuration was established using electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + probability analysis. The isolated compounds <b<1</b<–<b<10</b< were evaluated for their effects on glucose-stimulated insulin secretion in the INS-1 rat pancreatic β-cell line. The new compound <b<1</b<, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane, stimulated glucose-stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. Thus, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), an active compound derived from <i<S. rebaudiana</i< leaves, can be used as a potential therapeutic agent to prevent type 2 diabetes.
abstractGer	<i<Stevia rebaudiana</i< (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natural products, phytochemical investigation of the ethanolic extract of <i<S. rebaudiana</i< leaves led to the isolation of one new labdane-type diterpene, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), and nine known terpenoids, including six diterpenes (<b<2</b<–<b<6</b< and <b<10</b<), two monoterpenes (<b<7</b< and <b<8</b<), and one triterpene (<b<9</b<). The structure of the new compound <b<1</b< was elucidated via analysis of one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry data, and its absolute configuration was established using electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + probability analysis. The isolated compounds <b<1</b<–<b<10</b< were evaluated for their effects on glucose-stimulated insulin secretion in the INS-1 rat pancreatic β-cell line. The new compound <b<1</b<, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane, stimulated glucose-stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. Thus, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), an active compound derived from <i<S. rebaudiana</i< leaves, can be used as a potential therapeutic agent to prevent type 2 diabetes.
abstract_unstemmed	<i<Stevia rebaudiana</i< (Asteraceae), commonly known as candyleaf, sweetleaf, or sugarleaf, is a branched bushy shrub whose leaves are used as a natural sweetener owing to the high content of sweet diterpenes. As part of our ongoing work to identify structurally novel and bioactive natural products, phytochemical investigation of the ethanolic extract of <i<S. rebaudiana</i< leaves led to the isolation of one new labdane-type diterpene, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), and nine known terpenoids, including six diterpenes (<b<2</b<–<b<6</b< and <b<10</b<), two monoterpenes (<b<7</b< and <b<8</b<), and one triterpene (<b<9</b<). The structure of the new compound <b<1</b< was elucidated via analysis of one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry data, and its absolute configuration was established using electronic circular dichroism (ECD) calculations and gauge-including atomic orbital NMR chemical shift calculations, followed by DP4 + probability analysis. The isolated compounds <b<1</b<–<b<10</b< were evaluated for their effects on glucose-stimulated insulin secretion in the INS-1 rat pancreatic β-cell line. The new compound <b<1</b<, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane, stimulated glucose-stimulated insulin secretion in INS-1 pancreatic β-cells without inducing cytotoxicity. Thus, 6-<i<O</i<-acetyl-(12<i<R</i<)-epiblumdane (<b<1</b<), an active compound derived from <i<S. rebaudiana</i< leaves, can be used as a potential therapeutic agent to prevent type 2 diabetes.
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container_issue	4, p 839
title_short	A New Labdane-Type Diterpene, 6-<i<O</i<-Acetyl-(12<i<R</i<)-epiblumdane, from <i<Stevia rebaudiana</i< Leaves with Insulin Secretion Effect
url	https://doi.org/10.3390/biomedicines10040839 https://doaj.org/article/6c5acf47219147d29307936e6d250cd0 https://www.mdpi.com/2227-9059/10/4/839 https://doaj.org/toc/2227-9059
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author2	Dahae Lee Ki Sung Kang Ki Hyun Kim
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up_date	2024-07-04T00:31:15.783Z
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