Highly conjugated norditerpenoid and pyrroloquinoline alkaloids with potent PTP1B inhibitory activity from Nigella glandulifera

Qi-Bin Chen; Xue-Lei Xin; Yi Yang; Shoei-Sheng Lee; H A Aisa

doi:10.1021/np4009078

Highly conjugated norditerpenoid and pyrroloquinoline alkaloids with potent PTP1B inhibitory activity from Nigella glandulifera

J Nat Prod. 2014 Apr 25;77(4):807-12. doi: 10.1021/np4009078. Epub 2014 Mar 4.

Authors

Qi-Bin Chen¹, Xue-Lei Xin, Yi Yang, Shoei-Sheng Lee, H A Aisa

Affiliation

¹ The Key Laboratory of Plant Resources and Chemistry of Arid Zone and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences , Urumqi 830011, People's Republic of China.

PMID: 24593120
DOI: 10.1021/np4009078

Abstract

Three norditerpenoid alkaloids, nigelladines A-C (1-3), and one pyrroloquinoline alkaloid, nigellaquinomine (4), all possessing new skeletons with highly conjugated systems, were isolated from Nigella glandulifera. The 8aS-configuration for 1 and 2 was determined by comparison of the experimental and calculated electronic circular dichroism spectra. These alkaloids exhibited potent protein tyrosine phosphatase 1B (PTP1B) inhibitory activity but are devoid of cytotoxicity against the A431 cell line at 100 μM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification*
Alkaloids / pharmacology*
Circular Dichroism
Diterpenes / chemistry
Diterpenes / isolation & purification*
Diterpenes / pharmacology*
Drug Screening Assays, Antitumor
Molecular Structure
Nigella / chemistry*
Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
Pyrroles
Quinolines

Substances

Alkaloids
Diterpenes
Pyrroles
Quinolines
nigelladine A
nigelladine B
nigelladine C
pyrroloquinoline
PTPN1 protein, human
Protein Tyrosine Phosphatase, Non-Receptor Type 1