Novel sesterterpenes from Leucosceptrum canum of nepalese origin.

Org Lett

H. E. J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan.

Published: November 2004

Two novel sesterterpenoids, leucosesterterpenone (1) and leucosesterlactone (2), with novel skeleta were isolated from the hexane extract of the medicinal plant, Leucosceptrum canum. Their structures were established by the analysis of NMR data and the single-crystal X-ray diffraction of compound 1. Compounds 1 and 2 were found to exhibit activity against prolylendopeptidase (PEP).

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol040040yDOI Listing

Publication Analysis

Top Keywords

leucosceptrum canum
8
novel sesterterpenes
4
sesterterpenes leucosceptrum
4
canum nepalese
4
nepalese origin
4
origin novel
4
novel sesterterpenoids
4
sesterterpenoids leucosesterterpenone
4
leucosesterterpenone leucosesterlactone
4
leucosesterlactone novel
4

Similar Publications

Immunosuppressive leucosceptrane-type sesterterpenoids with antipodal cyclopentenones isolated from Leucosceptrum canum.

Phytochemistry

January 2025

State Key Laboratory of Southwestern Chinese Medicine Resources, and Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137, PR China; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, PR China. Electronic address:

Ten undescribed leucosceptrane-type sesterterpenoids with antipodal cyclopentenone moieties were isolated from the leaves of Leucosceptrum canum. Their structures including absolute configurations were elucidated by comprehensive spectroscopic analyses (including 1D and 2D NMR, and HRMS) and ECD calculations. In vitro immunosuppressive effects of these sesterterpenoids against the proliferation of T cells and the secretion of cytokine IFN-γ were evaluated.

View Article and Find Full Text PDF

Leucosceptrane sesterterpenoids from Tibetan Leucosceptrum canum and their immunosuppressive activity.

Fitoterapia

October 2024

State Key Laboratory of Southwestern Chinese Medicine Resources, and Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, PR China; Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China. Electronic address:

Phytochemical investigation on the leaves of Tibetan Leucosceptrum canum, a Chinese medicinal herb, led to the isolation of seven new leucosceptrane sesterterpenoids (1-7) and five known analogs (8-12). Comprehensive spectroscopic analysis (including 1D and 2D NMR, and HRMS), quantum chemistry computations, and single crystal X-ray crystallographic analysis were applied to elucidate their structures. Compounds 1-3 and 6 were the first examples of the leucosceptrane sesterterpenoids with rare C-2 oxidation.

View Article and Find Full Text PDF

Immunosuppressive leucosesterterpane and penta-nor-leucosesterterpane sesterterpenoids from Leucosceptrum canum.

Phytochemistry

September 2024

Key Laboratory of Phytochemistry and Natural Medicines, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, PR China; State Key Laboratory of Southwestern Chinese Medicine Resources, and Innovative Institute of Chinese Medicine and Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137, PR China. Electronic address:

Five undescribed leucosesterterpane sesterterpenoids, leucosceptrines A-E, two undescribed penta-nor-leucosesterterpane (C) sesterterpenoids, nor-leucosceptrines A and B, and three known analogues, were obtained from the aerial parts of Leucosceptrum canum of Chinese origin. Leucosceptrines A-C are the first examples of leucosesterterpane-type sesterterpenoids with unclosed dihydropyran rings and reverse configurations at chiral centers C-4 and/or C-12. Nor-leucosceptrines A and B possesses an unusual penta-nor-leucosesterterpane skeleton.

View Article and Find Full Text PDF

Unusual immunosuppressive pyridine-containing - (c), - (c) and - (c) sesterterpenoids from Tibetan .

Org Biomol Chem

April 2024

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.

An unusual pyridine-containing sesterterpenoid, leucosceptrodine (1), and five new -leucosceptrane sesterterpenoids, including - (C, 2), - (C, 3) and - (C, 4-6) skeletons, were isolated from the leaves of Tibetan . Their structures including their absolute configurations were determined by extensive spectroscopic analyses and quantum chemical calculations. A single crystal of one epimer (5) was crystallized from a pair of inseparable epimers, and its structure including its absolute configuration was determined by X-ray crystallographic analysis.

View Article and Find Full Text PDF

Generation, degradation mechanism, and toxicity evaluation of pigmented compounds in Leucosceptrum canum nectar.

Food Chem

July 2024

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China. Electronic address:

Leucosceptrum canum nectar (LCN) emerges as a novel food resource, distinguished by its unique dark brown hue. This study delves into the composition and toxicity assessment of novel pigments within LCN. Through liquid chromatography-tandem mass spectrometry (LC-MS/MS) and chemical synthesis, seventeen 2,5-di-(N-(-)-prolyl)-para-benzoquinone (DPBQ) analogs in LCN were identified.

View Article and Find Full Text PDF

Want 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!