Semisynthesis and Biological Evaluation of Ganodermanontriol and Its Stereoisomeric Triols
ABSTRACT The first synthesis of ganodermanontriol, a bioactive lanostane triterpene from the medicinal mushroom Ganoderma lucidum, has been achieved in 15.3% yield over nine steps, along with its three stereoisomeric triols and ganoderol A. The key steps leading to this family of isomers involve the reconstruction of the trisubstituted alkene by stereoselective and chemoselective phosphonate reactions and the formation of the unusual Δ7,9(11)-diene core by the mild acidic opening of a lanosterone-derived epoxide. Ganodermanontriol showed promising activity on the inhibition and proliferation of breast cancer cells. The effect of ganodermanontriol and its isomers on cell proliferation was assayed; IC50 values of 5.8 and 9.7 μM on breast cancer cell lines MCF-7 and MDA-MB-231, respectively, were found for ganodermanontriol.
SourceAvailable from: kai-long ji[Show abstract] [Hide abstract]
ABSTRACT: Nine new cedrelone limonoids, namely, walsuranolide B (1), 11β-hydroxy-23-O-methylwalsuranolide (2), yunnanolide A (3), yunnanol A (4), 11β-hydroxyisowalsuranolide (5), 11β-hydroxy-1,2-dihydroisowalsuranolide (6), 1α,11β-dihydroxy-1,2-dihydroisowalsuranolide (7), 11β-hydroxy-1α-methoxy-1,2-dihydroisowalsuranolide (8), and yunnanolide B (9), together with a new cycloartane triterpenoid, (24S*,25R*)-cycloartane-3β,24,25,26-tetrol (10), were isolated from the leaves and twigs of Walsura yunnanensis. Their structures were elucidated on the basis of spectroscopic analysis and by comparison with literature data. Compounds 3 and 5 exhibited potent cytotoxicity against five human tumor cell lines with IC50 values in the range 2.2-4.2 μM.Journal of Natural Products 07/2014; 77(8). DOI:10.1021/np400976p · 3.95 Impact Factor
[Show abstract] [Hide abstract]
ABSTRACT: Nine lanostanoids, together with nine known ones, were isolated from the ethyl acetate extract of the fruiting bodies of the mushroom Haddowia longipes. Their structures were elucidated as 11-oxo-ganoderiol D, lanosta-8-en-7,11-dioxo-3β-acetyloxy-24,25,26-trihydroxy, lanosta-8-en-7-oxo-3β-acetyloxy-11β,24,25,26-tetrahydroxy, lanosta-7,9(11)-dien-3β-acetyloxy-24,25,26-trihydroxy, lanosta-7,9(11)-dien-3β-acetyloxy-24,26-dihydroxy-25-methoxy, 11-oxo-lucidadiol, 11β-hydroxy-lucidadiol, lucidone H and lanosta-7,9(11),24E-trien-3β-acetyloxy-26,27-dihydroxy by analysing their 1D/2D NMR and MS spectra. In addition, bioassays of inhibitory activity against acetylcholinesterase (AChE) of all compounds showed that thirteen compounds possessed inhibitory activity against AChE with the percentage inhibition ranging from 10.3% to 42.1% when tested at 100 μM.Phytochemistry 01/2015; DOI:10.1016/j.phytochem.2014.12.012 · 3.35 Impact Factor
[Show abstract] [Hide abstract]
ABSTRACT: Fourteen lanostane triterpenoids were identified from Ganoderma hainanense.•X-ray single crystal diffraction analysis determined the 25S configuration in ganoderma acids from G. hainanense.•One of the triterpenoids has a 29-norlanostane structure.Phytochemistry 10/2014; DOI:10.1016/j.phytochem.2014.10.009 · 3.35 Impact Factor