[structures: see text] Lancifodilactone F (1), possessing an unprecedented rearranged pentanortriterpenoid backbone derived from cycloartane, was isolated from the leaves and stems of Schisandra lancifolia (Rehd. et Wils) A. C. Smith. Its structure was established by comprehensive NMR and MS spectroscopic analysis, coupled with single-crystal X-ray experiment. Compound 1 exerted minimal cytotoxicity against C8166 cells (CC50 > 200 microg/mL) and showed anti-HIV activity with EC50 = 20.69 +/- 3.31 microg/mL and a selectivity index > 6.62.
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http://dx.doi.org/10.1021/ol0473187 | DOI Listing |
Org Lett
March 2018
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.
Ten schinortriterpenoids with biogenetically related lancischiartane scaffolds, including the first 3-norlancischiartane (1) with unusual configuration inversions occurring at C-1 and C-10, were isolated from Schisandra lancifolia. Unusual ECD curve patterns observed in 6-8 were confirmed to be caused by nondegenerate exciton coupling, suggesting that ECD spectrum empirical comparison should be used with caution in configuration determination. Additionally, structure revision of 2, originally proposed as arisanlactone A, was completed using NMR computation and X-ray diffraction analysis.
View Article and Find Full Text PDFNat Prod Commun
December 2015
Two new 18-norschiartane-type schinortriterpenoids, namely wuwezidilactones Q (1) and R (2) were isolated from the stems of Schisandra lancifolia. Their structures were determined on the basis of extensive spectroscopic analysis. The absolute configurations of the new compounds were further determined by ROESY and an empirical comparison of their experimental ECD spectra with literature.
View Article and Find Full Text PDFOrg Lett
January 2016
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.
Lancolide E (1) featuring a complex tetracyclo[5.4.0.
View Article and Find Full Text PDFOrg Lett
March 2014
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, Yunnan, P. R. China.
Six unique nortriterpenoids, lancifonins A-F (1-6), were isolated from Schisandra lancifolia. Their absolute configurations were determined by X-ray diffraction and ECD calculation. The conformational analysis of 1 was performed due to the unanticipated changes of Cotton effects in its ECD spectrum.
View Article and Find Full Text PDFOrg Lett
October 2013
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany , Chinese Academy of Sciences, Kunming 650201, Yunnan, P. R. China, Shanghai Institute of Materia Medica , Chinese Academy of Sciences, Shanghai 201203, P. R. China, and University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
A new class of highly oxygenated Schisandra nortriterpenoids, lancolides A-D (1-4), from Schisandra lancifolia, represents the first example of natural products that possess a tricyclo[6.3.0.
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