Spirocyclopropane-type sesquiterpene hydrocarbons from Schinus terebinthifolius Raddi

• Published in: Phytochemistry (Oxford) Vol. 71; no. 11; pp. 1371 - 1374
• Main Authors: Richter, Rita, von Reuß, Stephan H., König, Wilfried A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.08.2010; Elsevier
• Subjects: Anacardiaceae; Anacardiaceae - chemistry; Biochemistry & Molecular Biology; Biological and medical sciences; chemical constituents of plants; Chemical constitution; chemical structure; essential oils; fruits (plant anatomy); Fundamental and applied biological sciences. Psychology; gas chromatography; Gas Chromatography-Mass Spectrometry; General pharmacology; Germany; invasive species; Life Sciences & Biomedicine; mass spectrometry; Medical sciences; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oils, Volatile - chemistry; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phytochemicals; Plant physiology and development; Plant Sciences; Schinus terebinthifolius; Science & Technology; Sesquiterpene hydrocarbons; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; sesquiterpenoids; Spirocyclopropane; Stereoisomerism; Terebanene; Terebinthane; Terebinthene; Teredenene; Germany; Spirocyclopropane; Terebinthane; Terebinthene; Sesquiterpene hydrocarbons; Terebanene; Teredenene; Schinus terebinthifolius; Anacardiaceae; PTAQUILOSIDE; BRACKEN FERN; GLUCOSIDE; Hydrocarbon; Pharmacognosy; Chemical structure; Medicinal plant; Dicotyledones; Sesquiterpenes; Angiospermae; Plant origin; Spermatophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2010.05.003

Three sesquiterpene hydrocarbons with a spirocyclopropane skeleton (terebinthane) have been isolated from the fruits of Schinus terebinthifolius. Their structures were determined by a combination of mass spectrometry, and one- and two-dimensional NMR techniques. The essential oil of Schinus terebinthifolius fruits was reinvestigated using GC and GC–MS techniques. Apart from several known compounds three sesquiterpene hydrocarbons with a carbon skeleton exhibiting the rare spiro(cyclopropane) moiety could be isolated by a combination of column chromatography and GLC. Structure assignments were carried out by NMR spectroscopy. These natural products are 9-spiro(cyclopropa)-4,4,8-trimethyl-2-methylenbicyclo[4.3.0]non-1(6)-ene (terebanene), 9-spiro(cyclopropa)-2,4,4,8-tetramethylbicyclo[4.3.0]nona-1,5-diene (teredenene), and (6 R∗,8 R∗)-9-spiro(cyclopropa)-2,4,4,8-tetramethylbicyclo[4.3.0]non-1-ene (terebinthene).