ABSTRACT
Daphmacrimines A-K (1-11) were isolated from the leaves and stems of Daphniphyllum macropodum Miq. Their structures and stereochemistries were determined by extensive techniques, including HRESIMS, NMR, ECD, IR, and single-crystal X-ray crystallography. Daphmacrimines A-D (1-4) are unprecedented Daphniphyllum alkaloids with a 2-oxazolidinone ring. Daphmacrimine I (9) contains a nitrile group, which is relatively rare in naturally occurring alkaloids. The abilities of daphmacrimines A-D and daphmacrimines G-K to enhance lysosomal biogenesis were evaluated through LysoTracker Red staining. Daphmacrimine K (11) can induce lysosomal biogenesis and promote autophagic flux.
Subject(s)
Alkaloids , Daphniphyllum , Alkaloids/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Molecular Structure , Daphniphyllum/chemistry , Plant Leaves/chemistry , Humans , Crystallography, X-Ray , Lysosomes/drug effects , Lysosomes/metabolism , Plant Stems/chemistry , Molecular ConformationABSTRACT
Two polycyclic polyprenylated acylphloroglucinols, garcimulins A and B ((±)-1 and 2), including a pair of enantiomers with the unique caged tetracyclo[5.4.1.1(1,5).0(9,13)]tridecane skeleton were isolated from Garcinia multiflora. Their structures and absolute configurations were determined by extensive analysis of spectroscopic data and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 exhibited cytotoxic activities against five human cancer cell lines in vitro (IC50 3.42-13.23 µM). The acidification of lysosomes in HeLa cell was obviously affected by compound 2.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Garcinia/chemistry , Phloroglucinol/analogs & derivatives , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Drug Screening Assays, Antitumor , HL-60 Cells , HeLa Cells , Humans , Lysosomes/drug effects , Molecular Structure , Phloroglucinol/chemistry , Phloroglucinol/isolation & purification , Phloroglucinol/pharmacology , StereoisomerismABSTRACT
The title compound, C(15)H(14)O(3), has been obtained from the reaction of 2,4-dihy-droxy-acetophenone, potassium carbonate and benzyl bromide. The remaining hy-droxy group is involved in an intra-molecular O-Hâ¯O hydrogen bond. In the crystal, inter-molecular C-Hâ¯O contacts occur.