Identification of new pyrrole alkaloids from the fruits of Lycium chinense

Ui Joung Youn; Joo Yun Lee; Yun Seo Kil; Ah Reum Han; Chong Hak Chae; Shi Yong Ryu; Eun Kyoung Seo

doi:10.1007/s12272-015-0695-3

Identification of new pyrrole alkaloids from the fruits of Lycium chinense

Ui Joung Youn, Joo Yun Lee, Yun Seo Kil, Ah Reum Han, Chong Hak Chae, Shi Yong Ryu, Eun Kyoung Seo

Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

Three new minor pyrrole alkaloids, 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid (1), (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-1-methoxy-1-oxobutanoic acid (2), and methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (3) were isolated from the fruits of Lycium chinense Miller (Solanaceae), along with the known compound, methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(phenyl)propanoate (4). The structures of 1-4 were elucidated by analysis of their 1D- and 2D-NMR and HRMS data. The absolute configurations of 2-4, possessing a stereogenic center in each structure, were determined by comparison of their experimental electronic circular dichroism (ECD) with those of calculated ECD values.

Original language	English
Pages (from-to)	321-327
Number of pages	7
Journal	Archives of Pharmacal Research
Volume	39
Issue number	3
DOIs	https://doi.org/10.1007/s12272-015-0695-3
State	Published - Mar 2016

Keywords

Absolute configuration
ECD
Lycium chinense
Pyrrole alkaloid
Solanaceae

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title = "Identification of new pyrrole alkaloids from the fruits of Lycium chinense",

abstract = "Three new minor pyrrole alkaloids, 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid (1), (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-1-methoxy-1-oxobutanoic acid (2), and methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (3) were isolated from the fruits of Lycium chinense Miller (Solanaceae), along with the known compound, methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(phenyl)propanoate (4). The structures of 1-4 were elucidated by analysis of their 1D- and 2D-NMR and HRMS data. The absolute configurations of 2-4, possessing a stereogenic center in each structure, were determined by comparison of their experimental electronic circular dichroism (ECD) with those of calculated ECD values.",

keywords = "Absolute configuration, ECD, Lycium chinense, Pyrrole alkaloid, Solanaceae",

author = "Youn, {Ui Joung} and Lee, {Joo Yun} and Kil, {Yun Seo} and Han, {Ah Reum} and Chae, {Chong Hak} and Ryu, {Shi Yong} and Seo, {Eun Kyoung}",

note = "Funding Information: This paper (Youn UJ) was supported by [RP-Grant 2010 of Ewha Womans University]. Publisher Copyright: {\textcopyright} The Pharmaceutical Society of Korea 2015.",

year = "2016",

month = mar,

doi = "10.1007/s12272-015-0695-3",

language = "English",

volume = "39",

pages = "321--327",

journal = "Archives of Pharmacal Research",

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publisher = "Pharmaceutical Society of Korea",

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}

TY - JOUR

T1 - Identification of new pyrrole alkaloids from the fruits of Lycium chinense

AU - Youn, Ui Joung

AU - Lee, Joo Yun

AU - Kil, Yun Seo

AU - Han, Ah Reum

AU - Chae, Chong Hak

AU - Ryu, Shi Yong

AU - Seo, Eun Kyoung

N1 - Funding Information: This paper (Youn UJ) was supported by [RP-Grant 2010 of Ewha Womans University]. Publisher Copyright: © The Pharmaceutical Society of Korea 2015.

PY - 2016/3

Y1 - 2016/3

N2 - Three new minor pyrrole alkaloids, 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid (1), (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-1-methoxy-1-oxobutanoic acid (2), and methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (3) were isolated from the fruits of Lycium chinense Miller (Solanaceae), along with the known compound, methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(phenyl)propanoate (4). The structures of 1-4 were elucidated by analysis of their 1D- and 2D-NMR and HRMS data. The absolute configurations of 2-4, possessing a stereogenic center in each structure, were determined by comparison of their experimental electronic circular dichroism (ECD) with those of calculated ECD values.

AB - Three new minor pyrrole alkaloids, 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid (1), (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-1-methoxy-1-oxobutanoic acid (2), and methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (3) were isolated from the fruits of Lycium chinense Miller (Solanaceae), along with the known compound, methyl (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(phenyl)propanoate (4). The structures of 1-4 were elucidated by analysis of their 1D- and 2D-NMR and HRMS data. The absolute configurations of 2-4, possessing a stereogenic center in each structure, were determined by comparison of their experimental electronic circular dichroism (ECD) with those of calculated ECD values.

KW - Absolute configuration

KW - ECD

KW - Lycium chinense

KW - Pyrrole alkaloid

KW - Solanaceae

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JO - Archives of Pharmacal Research

JF - Archives of Pharmacal Research

IS - 3

ER -

Identification of new pyrrole alkaloids from the fruits of Lycium chinense

Abstract

Keywords

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