ABSTRACT
To enrich the bioactive cycloartane triterpenoid glycoside named actein and find out more cytotoxic cycloartane triterpenes, a phytochemical study of Cimicifuga foetida was conducted. 113 g (0.17%) actein was purified by recrystallization while eight cycloartane-type triterpenes (1-8) were isolated from the mother liquid. The chemical structures of new compounds (1-4) were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses. Moreover, new compounds showed moderate and broad-spectrum cytotoxicity against 5 human cancer cell lines with IC50 values ranging from 4.02 to 15.80 µM.
ABSTRACT
Five new aromatic compounds, designed as lucidumins A-D (1-4) and lucidimine E (9), along with seven known aromatic compounds (5-8, 10-12) were isolated from Ganoderma lucidum. Their structures were determined by spectroscopic method. Bioactive evaluation showed that compounds 2-4 and 6-10 displayed remarkable neuroprotective activities against corticosterone-induced PC12 cell damage, with the cell viability ranging from 69.99% to 126.00%; and compounds 1-4, 9 and 10 exhibited significant anti-inflammatory activities against LPS-induced nitric oxide (NO) production in RAW264.7 macrophages, with IC50 values ranging from 4.68 to 15.49⯵M. In particular, compound 10 showed remarkable neuroprotection with EC50 value of 2.49⯱â¯0.12⯵M, and potent anti-inflammation with IC50 value of 4.68⯱â¯0.09⯵M.
Subject(s)
Anti-Inflammatory Agents/pharmacology , Ganoderma/chemistry , Neuroprotective Agents/pharmacology , Animals , Cell Survival , China , Fruiting Bodies, Fungal/chemistry , Mice , Molecular Structure , Nitric Oxide/metabolism , PC12 Cells , RAW 264.7 Cells , RatsABSTRACT
One new 15,16-seco-cycloartane triterpene (1: ), three new cycloartane triterpene glycosides (2: -4: ), and five known compounds (5: -9: ) were isolated from the aerial parts of Actaea heracleifolia. The chemical structures of these compounds were determined on the basis of NMR analysis, HRTOF-ESIMS data, and other spectroscopic methods. Selected compounds were evaluated for their cytotoxicity against human tumor cell lines (HL-60, SMMC-7721, A549, MCF-7, and SW480) in vitro. Compounds 3: and 4: showed weak activity against the HL-60, A-549, and MCF-7 cell lines with IC50 values ranging from 21.34 to 36.98 µM.
Subject(s)
Actaea/chemistry , Antineoplastic Agents/chemistry , Triterpenes/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Humans , Magnetic Resonance Spectroscopy , Plant Leaves/chemistry , Plant Stems/chemistry , Triterpenes/isolation & purificationABSTRACT
A new alkaloid, (E)-3-(3-methyl-1-oxo-2-butenyl)-6-methoxy-1 H -indole (1), along with two known ones, was isolated from the aerial parts of Cimicifuga heracleifolia. The structure of 1 was elucidated on the basis of extensive spectroscopic data analysis. The structures of known compounds were determined by comparison with the literature data.
Subject(s)
Alkaloids , Cimicifuga , Indole Alkaloids , Molecular StructureABSTRACT
Seven unprecedented high molecular weight hybrids of cycloartane triterpenoid saponins and chromone glycosides, namely, Cimitriteromone A-G (1-7), and three known biogenetic precursors (8-10) were isolated from the rhizomes of Cimicifuga foetida by using the HPLC-UV/MS method. The structures of the new compounds were determined by NMR analysis and HRESIMS data. The absolute configurations of sugar moieties were established by a chemical method. The new compounds 2 and 4 showed antiproliferative activities against Taxol-resistant human lung cancer A-549/Taxol with IC50 values of 15.73 ± 0.59 and 24.21 ± 0.61 µM, respectively, while the positive control groups cisplatin and Taxol gave IC50 values of 25.80 ± 1.15 and 0.60 ± 0.09 µM. Notably, compound 4 showed comparable cytotoxicity to the positive control, cisplatin, whereas the corresponding biogenetic precursors compounds 8 and 10 were inactive (IC50 > 40 µM).
Subject(s)
Chromones/chemistry , Cimicifuga/chemistry , Rhizome/chemistry , Triterpenes/chemistry , Models, Molecular , Molecular ConformationABSTRACT
Two new cycloartane triterpenes, cimyunnin E (1), containing a unique oxaspiro[4.4]nonanedione moiety based on rings D and E, together with cimicifine B (2), a 25,26,27-trinortriterpene featuring a pyridine ring E, were purified from the fruits of Cimicifuga yunnanensis. Their structures were elucidated by spectroscopic methods and ECD (electronic circular dichroism calculations). Compounds 1 and 2 showed significant acetylcholinesterase (AChE) inhibition with IC50 values of 1.58 and 3.87 µM, respectively. In addition, they noticeably enhanced the neurite outgrowth of nerve growth factor (NGF) mediated PC12 cells at a concentration of 10 µM.