Fragrant Volatile Sesquiterpenoids Isolated from the Essential Oil of Laggera pterodonta by Using Olfactory‐Guided Fractionation

Abstract

Chemical composition of the essential oil from Laggera pterodonta (Compositae) was inverstigated. GC/MS Analyses led to the identification of 68 components, representing more than 96% of the total oil. By focusing on the woody note fraction of the essential oil, one new bisabolane‐type sesquiterpenoid, bisabola‐2,7(14),11‐trien‐10‐ol (1), together with ten known compounds, bisabolol oxide B (2), ylangenol (3), copaborneol (4), guai‐11‐en‐10‐ol (5), spathulenol (6), aromadendran‐10‐ol (7), caryophyllenol (8), 5α,7α‐eudesm‐11(13)‐en‐4α‐ol (9), γ‐costic acid (10), and eudesma‐4(15),11(13)‐diene‐12,5β‐olide (11), were isolated by using olfactory‐guided fractionation. The structures of the eleven compounds were determined by NMR and MS analyses. All the volatile compounds reported here were isolated for the first time from this plant. On the basis of preliminary odor assessment, the odor of the woody‐note fractions of the essential oil was assumed to be due to these isolated sesquiterpenoids.

Composition and Intraspecific Chemical Variability of Leaf Essential Oil of Laggera pterodonta from Côte d'Ivoire

“…This concluded the clear difference between the chemical compositions of L. pterodonta leaf oil from Côte d'Ivoire and those from Cameroon and Benin. Otherwise, Ivoirian L. pterodonta leaf oils differed drastically from oils of Nigeria and China …”

“…The composition of a Beninese L. pterodonta leaf oil sample resembled that of Group II, while the Cameroonian leaf oil differed by the occurrence of γ ‐eudesmol and epi ‐ α ‐bisabolol beside 2,5‐dimethoxy‐ p ‐cymene . Finally, Ivoirian L. pterodonta leaf oil differed drastically from oils of Nigeria and China …”

“…Others displayed the association of dimethoxydurene with triacontane and caryophyllene oxide (aerial part, Nigeria) or dimethoxydurene with 4‐methylenebicyclo[3.1.0]hexane and caryophyllene (leaves, China) . Various L. pterodonta aerial part oil samples from China contained mainly sesquiterpenes or sesquiterpenes accompanied by monoterpenes or by a phenylpropanoid: isoeugenol, δ ‐selinene and α ‐humulene, 1,8‐cineole, β ‐eudesmol, β ‐selinene, γ ‐eudesmol, β ‐caryophyllene, δ ‐terpineol, β ‐pinene, α ‐humulene, δ ‐terpineol . Similarly, a leaf oil sample from Cameroun was dominated by γ ‐eudesmol, α ‐bisabolol, juniper camphor .…”

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

“…[90] Compound 12 has been isolatedf rom many plant species. [73,80,82,[89][90][91][92][93][94][95][96][97][98][99][100][101][102] Neointermedeol (13)w as first reported from the grass Bothriochloa intermedia,w ith an opticalr otation of [a] D 25 = + 7.5, [103,104] while the material isolatedl ater from Panax ginseng exhibited an egative optical rotation( [ a] D 22 = À4.8, c 3.45, CHCl 3 ). [84] To resolve the situation (À)-13 was dehydrated with POCl 3 in pyridine,y ielding( + +)-6 and thus securing the absolute configuration of 13 (Scheme 10 C).…”

Purification of Houttuynia cordata Thunb. Essential Oil Using Macroporous Resin Followed by Microemulsion Encapsulation to Improve Its Safety and Antiviral Activity

“…However, to our knowledge, there is no study reported on purification of essential oil from H. cordata . Generally, liquid–liquid extraction [ 18 ], fractionation [ 19 ], and silica gel column chromatography [ 20 ] are used for purification of natural products. Unfortunately, these extraction procedures are inefficient, costly, time and solvent consuming, and labor intensive [ 21 ].…”