Chemical Analysis of the Essential Oil from Siparuna echinata (Kunth) A. DC. (Siparunaceae) of Ecuador and Isolation of the Rare Terpenoid Sipaucin A

Abstract

The phytochemical research on the species Siparuna echinata, collected in the Province of Loja (Ecuador), led to the isolation of a rare sesquiterpenoid, called Sipaucin A. The structure was confirmed by nuclear magnetic resonance (NMR) and mass spectrometry (MS). Furthermore, the essential oil of the fruits was obtained by hydrodistillation and analyzed by gas chromatography, coupled to mass spectrometry (GC-MS) and flame ionization detector (GC-FID). Twenty-seven compounds were identified in a polydimethylsiloxane column (DB-5ms) and nineteen in a polyethylene glycol column (HP-INNOWax). Major compounds were α-pinene (24.3%, 20.3%), β-pinene (21.7%, 22.7%), β-myrcene (11.3%, 14.8%), limonene (10.0%, 11.3%), cis-ocimene (8.5%, 8.1%), and trans-ocimene (8.9%, 8.4%). In addition to the chemical analysis, the essential oil was submitted to enantioselective analysis of two major chiral monotherpenes, determining an enantiomeric excess of 100.0% for (+)-α-pinene and 6.7% for (+)-β-pinene.

Chemical and Enantioselective Analysis of the Leaf Essential Oil from Piper coruscans Kunth (Piperaceae), a Costal and Amazonian Native Species of Ecuador

“…Among the natural products the authors are interested in, we can cite essential oils (EOs) [ 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]. According to the European Pharmacopeia, an EO is an “odorous product, usually of complex composition, obtained from a botanically defined plant raw material by steam distillation, dry distillation, or a suitable mechanical process without heating.…”

Soil and Leaf Nutrients Drivers on the Chemical Composition of the Essential Oil of Siparuna muricata (Ruiz & Pav.) A. DC. from Ecuador

“…We also observe that the nutrient content of the soil and the plant, as well as the chemical composition of the essential oil, are strongly influenced by the sampling location. Other studies found α-pinene (24.3%), β-pinene (21.7%) and myrcene (11.3%) in Siparuna echinate (Khunt) as major compounds [ 7 ], following these patterns, germacrene D (23.2% and α-pinene (7.0) were found to be major compounds in S. macrotepala [ 32 ]. A study of S. schimpffii Diels, which is used as an analgesic by the Shuar people of the Ecuadorian Amazon, specifically in the province of Morona Santiago, representative components were: germacrene D (35.34%), bicyclogermacrene (8.73%), γ-muurulene (7.04%), germacrene B (6.36%) and trans-cadina-1 (2), 4-diene (5.16%), which was similar with the chemical composition from our study, with the exception of germacrene D [ 33 ].…”

“…In this context, several studies shown that the Siparunaceae family has great economic, medicinal and phytochemical importance [ 6 , 7 ]. The fruits and leaves of certain species are used as traditional medicines of South and Central America to treat fever, cough, gastrointestinal diseases and rheumatism, and also this species is used as timber [ 8 ].…”

“…Currently the most studies focus only on phytochemical analysis of Siparuna species [ 7 , 27 , 28 , 29 , 30 , 31 ] for instance, a phytochemical study in Siparuna muricata [ 9 ]. However, there is little information about the influences of soil and leaf chemical elements in relation to the composition of the essential oils.…”

The Flower Essential Oil of Dalea mutisii Kunth (Fabaceae) from Ecuador: Chemical, Enantioselective, and Olfactometric Analyses

“…Among natural products, a special interest exists in essential oils (EOs) [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ], whose main property is their aroma. In fact, they are defined in the European Pharmacopoeia as “odorous products, usually of complex composition, obtained from a botanically defined plant raw material by steam distillation, dry distillation, or a suitable mechanical process without heating.…”