C-seco triterpenoids are widely bioactive class of natural products with high structural complexity and diversity. The preparative isolation of these molecules with high purity is greatly desirable, although restricted due to the complexity of natural extracts. In this article we have demonstrated a Medium Pressure Liquid Chromatography (MPLC) based protocol for the isolation of eight major C-seco triterpenoids of salannin skeleton from Neem (Azadirachta indica) oil. Successive application of normal phase pre-packed silica-gel columns for the fractionation followed by reverse phase in automated MPLC system expedited the process and furnished highly pure metabolites. Furthermore, eight isolated triterpenoids along with five semi-synthesized derivatives were characterized using ultra performance liquid chromatography-electrospray ionization-quadrupole/orbitrap-MS/MS spectrometry as a rapid and sensitive identification technique. The structure-fragment relationships were established on the basis of plausible mechanistic pathway for the generation of daughter ions. The MS/MS spectral information of the triterpenoids was further utilized for the identification of studied molecules in the complex extract of stem and bark tissues from Neem.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.chroma.2014.09.006 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Computational Binding Study Hints at Ecdysone 20-Mono-Oxygenase as the Hitherto Unknown Target for Ring C-Seco Limonoid-Type Insecticides.
Molecules
April 2024
Laboratorio de Simulaciones Moleculares Computacionales, Facultad de Ciencias Químicas Benemérita, Universidad Autónoma de Puebla, Prol. 24 Sur, Puebla 72570, Mexico.
The insecticidal property of ring C-seco limonoids has been discovered empirically and the target protein identified, but, to date, the molecular mechanism of action has not been described at the atomic scale. We elucidate on computational grounds whether nine C-seco limonoids present sufficiently high affinity to bind specifically with the putative target enzyme of the insects (ecdysone 20-monooxygenase). To this end, 3D models of ligands and the receptor target were generated and their interaction energies estimated by docking simulations.
View Article and Find Full Text PDFLimonoids from the roots of Melia azedarach and their anti-inflammatory activity.
Phytochemistry
December 2023
State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences, University of Macau, Macao, PR China. Electronic address:
Twelve undescribed limonoids, meliazedarines J-U (1-12), along with a known one, were isolated from the roots of Melia azedarach. Their structures were elucidated by extensive spectroscopic investigations, X-ray diffraction analyses, and ECD calculations. Compounds 1-8 were identified as ring intact limonoids, while compounds 9-12 were established as ring C-seco ones.
View Article and Find Full Text PDFInsecticidal Triterpenes in Meliaceae: Plant Species, Molecules, and Activities: Part II (, ).
Int J Mol Sci
May 2022
Key Laboratory of Natural Pesticides and Chemical Biology, Ministry of Education, South China Agricultural University, Guangzhou 510642, China.
Plant-originated triterpenes are important insecticidal molecules. Research on the insecticidal activity of molecules from Meliaceae plants has always been a hotspot due to the molecules from this family showing a variety of insecticidal activities with diverse mechanisms of action. In this paper, we discussed 116 triterpenoid molecules with insecticidal activity from 22 plant species of five genera (, , , , and ) in Meliaceae.
View Article and Find Full Text PDFAnti-inflammatory role demonstrated both in vitro and in vivo models using nonsteroidal tetranortriterpenoid, Nimbin (N1) and its analogs (N2 and N3) that alleviate the domestication of alternative medicine.
Cell Biol Int
May 2022
Department of Biotechnology, College of Science and Humanities, SRM Institute of Science and Technology, Chennai, Tamil Nadu, India.
Human health may benefit from the study of natural compounds and phytoconstituents that can protect from inflammation. We investigated Nimbin (N1), a member of the ring C Seco-tetranortriterpenoids family, and its semi-natural analog deacetyl Nimbin namely N2 and N3 for their anti-inflammatory properties. As key findings, N1, N2, and N3 were able to improve wound healing by cell proliferation in a period of 24 h and were able to reduce the reactive oxygen species (ROS) production in Madin-Darby Canine Kidney cells which were screened using dichloro-dihydro fluorescein diacetate (DCF-DA) staining.
View Article and Find Full Text PDFLimonoids with Diverse Oxidation Patterns of C-12 Indicating a Complete Ring C- Biogenetic Pathway from .
J Nat Prod
August 2021
Jiangsu Key Laboratory of Bioactive Natural Product Research, State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, People's Republic of China.
Munrolins A-Q (-), 17 new ring C- limonoids with diverse oxidative patterns of C-12, together with nine known analogues (-), were isolated from the CHCl extract of . The planar structures were elucidated by a combination of 1D and 2D NMR and HR-MS analyses, while the absolute configurations were confirmed by ECD calculations and single-crystal X-ray diffraction. Munrolins A () and B () were first identified as ring C- limonoids with a 12,13-ether bridge moiety.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!