Two Enantiomeric Pairs of Meroterpenoids from Rhododendron capitatum

• Published in: Organic letters Vol. 17; no. 20; pp. 5040 - 5043
• Main Authors: Liao, Hai-Bing, Lei, Chun, Gao, Li-Xin, Li, Jing-Ya, Li, Jia, Hou, Ai-Jun
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.10.2015; Amer Chemical Soc
• Subjects: chemical reactions; chemical structure; Chemistry; Chemistry, Organic; Chromatography, High Pressure Liquid; Circular Dichroism; circular dichroism spectroscopy; Crystallography, X-Ray; Models, Molecular; Molecular Conformation; Molecular Structure; organic compounds; Physical Sciences; Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors; Rhododendron; Rhododendron - chemistry; Science & Technology; spectral analysis; Stereoisomerism; Terpenes - chemistry; Terpenes - isolation & purification; Terpenes - pharmacology; X-ray diffraction; ACID; PROTEIN; INHIBITOR; TYROSINE-PHOSPHATASE 1B; DERIVATIVES; CONSTITUENTS
• ISSN: 1523-7060; 1523-7052; 1523-7052
• DOI: 10.1021/acs.orglett.5b02515

Two enantiomeric pairs of meroterpenoids, (−)- and (+)-rhodonoids A (1a and 1b) and B (2a and 2b), were isolated unprecedentedly from partially racemic mixtures that naturally occurred in Rhododendron capitatum. Their structures were fully determined by spectroscopic data, X-ray crystallography, and electronic circular dichroism analysis. Compounds 1a and 1b are the first examples of meromonoterpenes featuring a unique 6/6/6/4 ring system. Compounds 2a and 2b showed PTP1B inhibitory activity.