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

Department of Pharmaceutical Sciences

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

24 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

Bibliographical note

Funding Information:
This paper (Youn UJ) was supported by [RP-Grant 2010 of Ewha Womans University].

Publisher Copyright:
© The Pharmaceutical Society of Korea 2015.

Keywords

Absolute configuration
ECD
Lycium chinense
Pyrrole alkaloid
Solanaceae

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10.1007/s12272-015-0695-3

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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",

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

language = "English",

volume = "39",

pages = "321--327",

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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

UR - https://www.scopus.com/pages/publications/84949973439

U2 - 10.1007/s12272-015-0695-3

DO - 10.1007/s12272-015-0695-3

M3 - Article

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AN - SCOPUS:84949973439

SN - 0253-6269

VL - 39

SP - 321

EP - 327

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

Bibliographical note

Keywords

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