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- Title
New Pyrrole Alkaloids with Bulky N-Alkyl Side Chains Containing Stereogenic Centers from Lycium chinense.
- Authors
Joung Youn, Ui; Kil, Yun-Seo; Nam, Joo-Won; Jin Lee, Yoo; Kim, Jinwoong; Lee, Dongho; Lee, Je-Hyun; Seo, Eun-Kyoung
- Abstract
Four new pyrrole alkaloids, methyl 2-[2-formyl-5-(methoxymethyl)-1 H-pyrrol-1-yl]propanoate ( 1), methyl 2-[2-formyl-5-(methoxymethyl)-1 H-pyrrol-1-yl]-3-(4-hydroxyphenyl)propanoate ( 2), dimethyl 2-[2-formyl-5-(methoxymethyl)-1 H-pyrrol-1-yl]butanedioate ( 3), and dimethyl 2-[2-formyl-5-(methoxymethyl)-1 H-pyrrol-1-yl]pentanedioate ( 4), were isolated from the AcOEt extract of the fruits of Lycium chinense Miller (Solanaceae). The stereogenic center C(2) in the bulky N-alkyl side chain in each of 1- 4 seems to hold the H-atoms of nearby CH2 groups, CH2(7′) and CH2(3) (if R≠H), leading to two different chemical shifts in the 1H-NMR spectrum due to their diastereotopic characteristics. In the 1H-NMR data of each of 2- 4, the enhancement of HC(2) signal was inhibited by the R group, probably due to steric hindrance, and its chemical shift was influenced by the anisotropy effect. The structures of 1- 4 were elucidated by analysis of various spectroscopic data, including 1D- and 2D-NMR.
- Subjects
PYRROLES; LYCIUM chinense; ALKALOIDS; ALKYL compounds; HYDROGEN atom
- Publication
Helvetica Chimica Acta, 2013, Vol 96, Issue 8, p1482
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201200608