Bioorganic Diversity of Rare Coriandrum sativum L. Honey: Unusual Chromatographic Profiles Containing Derivatives of Linalool/Oxygenated Methoxybenzene

Abstract

The compounds responsible for highly individual aroma profile of Coriandrum sativum L. honey were isolated by headspace solid-phase microextraction (HS-SPME; used fibers: A: polydimethylsiloxane (PDMS)/divinylbenzene (DVB) and B: divinylbenzene/carboxen/polydimethylsiloxane), as well as ultrasonic solvent extraction (USE; used solvents: A: pentane/Et2 O 1 : 2 (v/v) and B: CH2 Cl2 ) and analyzed by gas chromatography (GC) and mass spectrometry (MS). Unusual chromatographic profiles were obtained containing derivatives of linalool/oxygenated methoxybenzene. trans-Linalool oxide (11.1%; 14.6%) dominated in the headspace, followed by other linalool derivatives (such as cis/trans-anhydrolinalool oxide (5.0%; 5.9%), isomers of lilac aldehyde/alcohol (14.9%; 13.8%) or p-menth-1-en-9-al (15.6%; 18.5%)), octanal, and several low-molecular-weight esters. The major compounds in the solvent extracts were oxygenated methoxybenzene derivatives such as 3,4,5-trimethoxybenzyl alcohol (26.3%; 24.7%), methyl syringate (23.8%; 11.7%), and 3,4-dimethoxybenzyl alcohol (5.6%; 13.9%). Another group of abundant compounds in the extracts were derivatives of linalool (e.g., (E)/(Z)-2,6-dimethylocta-2,7-diene-1,6-diol (17.8%; 16.1%)). Among the compounds identified, cis/trans-anhydrolinalool oxides and 3,4,5-trimethoxybenzyl alcohol can be useful as chemical markers of coriander honey.

Screening of Polish Fir Honeydew Honey Using GC/MS, HPLC‐DAD, and Physical‐Chemical Parameters: Benzene Derivatives and Terpenes as Chemical Markers

“…Similarly, linalool derivatives have been found in various honey types, e.g ., from sour cherry, willow, or coriander and therefore, these compounds can serve only as non‐specific markers of FHH. In FHH, the total percentage of linalool derivatives in the headspace was high and ranged from 19.2% to 49.0%, ( A ; 16.3 – 48.4%, B ) and was similar or slightly lower than found in cherry (50.4 – 69.1%), willow (46.1%), and coriander (58.7 – 62.3%) honeys . However, the honey profiles differed in the distribution of specific linalool derivatives.…”

“…In FHH, linalool oxides and hotrienol were major compounds (see above), and in sour cherry honey, lilac aldehydes predominated (46.0 – 50.6%) . In willow and coriander nectar honeys, the distribution of derivatives was more balanced and lilac aldehydes accounted for 17.8% and 11.7 – 12.3%, respectively . The latter, in contrast to the other honeys, contained also a relevant amount of p ‐menth‐1‐en‐9‐al isomers (up to 18.5%) .…”

“…In willow and coriander nectar honeys, the distribution of derivatives was more balanced and lilac aldehydes accounted for 17.8% and 11.7 – 12.3%, respectively . The latter, in contrast to the other honeys, contained also a relevant amount of p ‐menth‐1‐en‐9‐al isomers (up to 18.5%) . Other identified compounds such as α ‐terpineol and borneol are more relevant regarding the source traceability, since those compounds are present in fir essential oil and could also be generated by transformation from related, more abundant components such as pinene, limonene, or bornyl acetate present in fir .…”

Biomedical Activity and Related Volatile Compounds of Thai Honeys from 3 Different Honeybee Species

“…Furthermore, aldehyde VOCs produce floral scent, esters produce fruity odours, and monoterpenes produce spicy, woody, and medicinal aroma. The common honey VOCs such as benzene acetaldehyde (Shimoda and others ; Serra Bonvehí and Ventura Coll ; Alissandrakis and others ; Baroni and others ; Castro‐Vázquez and others ); cis ‐linalool oxide (Jerković and others ; Aronne and others ); trans ‐linalool oxide (Castro‐Vázquez and others ; Soria and others ; Wolski and others ; Jerković and others ; Jerković and others ; Stanimirova and others ; Jerković and others ; Aronne and others ); 2,5‐furan dicarboxaldehyde (Wolski and others ); and benzeneethanol (D'arcy and others ; Piasenzotto and others ; Wolski and others ; Viuda‐Martos and others ) were detected in wild honey in higher amount especially cis ‐linalool oxide (Guyot and others ; Ampuero and others ; de la Fuente and others ; Montenegro and others ). This may support the fact that every wild honey sample gives stronger odour than coffee honey.…”

Flavonoids enantiomer distribution in different parts of goldenrod (Solidago virgaurea L.), lucerne (Medicago sativa L.) and phacelia (Phacelia tanacetifolia Benth.)

“…The mentioned flavanones have never been determined in phacelia. Only one study contains references to this plant in the context of the determination of the aforementioned flavanones in honey, and this study was focused on another plant species Coriandrum sativum L.; the botanical origin of the honey sample was confirmed by pollen analysis, and phacelia was found to be the honey additive …”