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A Pair of Enantiomeric Bis- seco-abietane Diterpenoids from Cryptomeria fortunei
- Source :
- Journal of natural products. 81(12)
- Publication Year :
- 2018
-
Abstract
- (±)-Cryptomeriolide, a pair of racemic bis- seco-abietane diterpenoids, were isolated from the bark of Cryptomeria fortunei. The separation of enantiomers was achieved by using chiral stationary phase HPLC. Their structures including the absolute configuration and conformations in solution and solid state were determined by extensive analysis of spectroscopic data, single-crystal X-ray diffraction, and comparison of calculated and experimental electronic circular dichroism data. A bioinspired one-pot enantiomeric synthesis of 1a and 1b was accomplished via a readily made intermediate orthoquinone from sugiol. All compounds including the synthetic intermediates were assayed for their cytotoxic activities on human cancer cell lines HL-60, A549, and SGC7901.
- Subjects :
- Circular dichroism
Stereochemistry
Cryptomeria
Solid-state
Pharmaceutical Science
HL-60 Cells
Crystallography, X-Ray
01 natural sciences
High-performance liquid chromatography
Analytical Chemistry
chemistry.chemical_compound
Természettudományok
Isomerism
Drug Discovery
Molecule
Humans
Kémiai tudományok
Chromatography, High Pressure Liquid
Abietane
Pharmacology
biology
Molecular Structure
010405 organic chemistry
Organic Chemistry
Absolute configuration
biology.organism_classification
Antineoplastic Agents, Phytogenic
0104 chemical sciences
010404 medicinal & biomolecular chemistry
Complementary and alternative medicine
chemistry
Abietanes
Plant Bark
Molecular Medicine
Enantiomer
Drug Screening Assays, Antitumor
Subjects
Details
- ISSN :
- 15206025
- Volume :
- 81
- Issue :
- 12
- Database :
- OpenAIRE
- Journal :
- Journal of natural products
- Accession number :
- edsair.doi.dedup.....56ed8df1c82b43cf4798a9841286122f