Chemical Composition and Antimicrobial Activity of the Essential Oil from the Edible Aromatic Plant Aristolochia delavayi

The essential oil obtained by hydrodistillation from the aerial parts of Aristolochia delavayi Franch. (Aristolochiaceae), a unique edible aromatic plant consumed by the Nakhi (Naxi) people in Yunnan, China, was investigated using GC/MS analysis. In total, 95 components, representing more than 95% of the oil composition, were identified, and the main constituents found were (E)‐dec‐2‐enal (52.0%), (E)‐dodec‐2‐enal (6.8%), dodecanal (3.35%), heptanal (2.88%), and decanal (2.63%). The essential oil showed strong inhibitory activity (96% reduction) of the production of bacterial volatile sulfide compounds (VSC) by Klebsiella pneumoniae, an effect that was comparable with that of the reference compound citral (91% reduction). Moreover, the antimicrobial activity of the essential oil and the isolated major compound against eight bacterial and six fungal strains were evaluated. The essential oil showed significant antibacterial activity against Providencia stuartii and Escherichia coli, with minimal inhibitory concentrations (MIC) ranging from 3.9 to 62.5 μg/ml. The oil also showed strong inhibitory activity against the fungal strains Trichophyton ajelloi, Trichophyton terrestre, Candida glabrata, Candida guilliermondii, and Cryptococcus neoformans, with MIC values ranging from 3.9 to 31.25 μg/ml, while (E)‐dec‐2‐enal presented a lower antifungal activity than the essential oil.     

Synthesis of trans-4-Amino-1-hydroxy-2-methyl-2-butene from Isoprene

A novel synthetic pathway to trans-4-amino-1-hydroxy-2-methyl-2-butene (7), a useful synthetic intermediate of zeatin, is presented here. On selective monophthalimide formation, the trans-1, 4-dibromo-2-methyl-2-butene (10) prepared from isoprene (1) predominantly gives trans-1-bromo-2-methyl-4-phthalimido-2-butene (11). The compound (11) is converted to 7 via trans-1-acetoxy-2-methyl-4-phthalimido-2-butene (6). The overall yield of 7 from 1 is 33.6%. Base-catalyzed hydrolysis of 11 also gives 7 directly. Zeatin can be prepared by the condensation of 7 with 6-chloropurine.     

Microbial Allyl Rearrangement and Resolution of Acetates of Unsaturated Cyclic Terpene Alchols by Pseudomonas sp. NOF-5 Strain

Microbial hydrolysis of the acetates of unsaturated cyclic terpene alcohols by Pseudomonas sp. NOF-5 isolated from soil was investigated. (±)-trans-Carveyl acetate ((±)-trans-3) was enantio-selectively hydrolyzed with NOF-5 strain to give ( – )-trans-carveol (( – )-trans-2 of 86.6% optical purity). However, the hydrolysis of (±)-cis-3 was less enantioselective, while (±)-piperitylacetate ((±)-6, a cis and trans mixture) was hydrolyzed to give the ( – )-trans- and ( – )-cis-piperitols (( – )- trans-5 and ( – )-cis-5) in a poor optical yield. In this case, other tert-alcohols, ( + )-trans- and ( – )- ds-2-p-menthen-1-ols ((±)-trans-7 and ( – )-cis-7), were also produced. Furthermore, microbial and enzymic allyl rearrangements of ( + )-trans-6 and ( – )-trans-verbenylacetate (( – )-trans-11) were studied. Biological treatment of (+)-trans-6 and ( – )-trans-11 with NOF-5 or its esterase gave (+)-trans- and (-)-cis-1 and ( + )-cis-3-pinen-2-ol (( + )-cis-12), respectively.     

Simultaneous analysis of tramadol, O-desmethyltramadol, and N-desmethyltramadol enantiomers in rat plasma by high-performance liquid chromatography-tandem mass spectrometry: application to pharmacokinetics

Tramadol (T) is available as a racemic mixture of (+)‐trans‐T and (−)‐trans‐T. The main metabolic pathways are O‐demethylation and N‐demethylation, producing trans‐O‐desmethyltramadol ( M1 ) and trans‐N‐desmethyltramadol ( M2 ) enantiomers, respectively. The analgesic effect of T is related to the opioid activity of (+)‐trans‐T and (+)‐ M1 and to the monoaminergic action of (+/−)‐trans‐T. This is the first study using tandem mass spectrometry as a detection system for the simultaneous analysis of trans‐T, M1 , and M2 enantiomers. The analytes were resolved on a Chiralpak® AD column using hexane:ethanol (95.5:4.5, v/v) plus 0.1% diethylamine as the mobile phase. The quantitation limits were 0.5 ng/ml for trans‐T and M1 and 0.1 ng/ml for M2 . The method developed and validated here was applied to a pharmacokinetic study in rats. Male Wistar rats (n = 6 at each time point) received a single oral dose of 20 mg/kg racemic trans‐T. Blood samples were collected up to 12 h after drug administration. The kinetic disposition of trans‐T and M2 was enantioselective (AUC_(+)/(−) ratio = 4.16 and 6.36, respectively). The direction and extent of enantioselectivity in the pharmacokinetics of trans‐T and M2 in rats were comparable to data previously reported for healthy volunteers, suggesting that rats are a suitable model for enantioselective studies of trans‐T pharmacokinetics. Chirality, 2011. © 2010 Wiley‐Liss, Inc.     

Electroantennogram and behavioral responses of Cotesia plutellae to plant volatiles

Plant volatiles have been demonstrated to play an important role in regulating the behavior of Cotesia plutellae, a major larval parasitoid of the diamondback moth (DBM), Plutella xylostella, but little is currently known about the function of each volatile and their mixtures. We selected 13 volatiles of the DBM host plant, a cruciferous vegetable, to study the electroantennogram (EAG) and behavioral responses of C. plutellae. EAG responses to each of the compounds generally increased with concentration. Strong EAG responses were to 100 μL/mL of trans‐2‐hexenal, benzaldehyde, nonanal and cis‐3‐hexenol, and 10 μL/mL of trans‐2‐hexenal and benzaldehyde with the strongest response provoked by trans‐2‐hexenal at 100 μL/mL. In the Y‐tube olfactometer, C. plutellae, was significantly attracted by 1 μL/mL of trans‐2‐hexenal and benzaldehyde. β‐caryophyllene, cis‐3‐hexenol or trans‐2‐hexenal significantly attracted C. plutellae at 10 μL/mL, while nonanal, benzyl alcohol, cis‐3‐hexenol or benzyl cyanide at 100 μL/mL significantly attracted C. plutellae. Trans‐2‐hexenal significantly repelled C. plutellae at 100 μL/mL. EAG of C. plutellae showed strong responses to all mixtures made of five various compounds with mixtures 3 (trans‐2‐hexenal, benzaldehyde, nonanal, cis‐3‐hexenol, benzyl cyanide, farnesene, eucalyptol) and 4 (trans‐2‐hexenal, benzaldehyde, benzyl alcohol, (R)‐(+)‐limonene, β‐ionone, farnesene, eucalyptol) significantly attracting C. plutellae. These findings demonstrate that the behavior of C. plutellae can be affected either by individual compounds or mixtures of plant volatiles, suggesting a potential of using plant volatiles to improve the efficiency of this parasitoid for biocontrol of P. xylostella.     

Metabolic Implications of Dietary Trans‐fatty Acids

Dietary trans‐fatty acids are associated with increased risk of cardiovascular disease and have been implicated in the incidence of obesity and type 2 diabetes mellitus (T2DM). It is established that high‐fat saturated diets, relative to low‐fat diets, induce adiposity and whole‐body insulin resistance. Here, we test the hypothesis that markers of an obese, prediabetic state (fatty liver, visceral fat accumulation, insulin resistance) are also worsened with provision of a low‐fat diet containing elaidic acid (18:1t), the predominant trans‐fatty acid isomer found in the human food supply. Male 8‐week‐old Sprague–Dawley rats were fed a 10% trans‐fatty acid enriched (LF‐trans) diet for 8 weeks. At baseline, 3 and 6 weeks, in vivo magnetic resonance spectroscopy (¹H‐MR) assessed intramyocellular lipid (IMCL) and intrahepatic lipid (IHL) content. Euglycemic–hyperinsulinemic clamps (week 8) determined whole‐body and tissue‐specific insulin sensitivity followed by high‐resolution ex vivo ¹H‐NMR to assess tissue biochemistry. Rats fed the LF‐trans diet were in positive energy balance, largely explained by increased energy intake, and showed significantly increased visceral fat and liver lipid accumulation relative to the low‐fat control diet. Net glycogen synthesis was also increased in the LF‐trans group. A reduction in glucose disposal, independent of IMCL accumulation was observed in rats fed the LF‐trans diet, whereas in rats fed a 45% saturated fat (HF‐sat) diet, impaired glucose disposal corresponded to increased IMCL_TA. Neither diet induced an increase in IMCL_soleus. These findings imply that trans‐fatty acids may alter nutrient handling in liver, adipose tissue, and skeletal muscle and that the mechanism by which trans‐fatty acids induce insulin resistance differs from diets enriched with saturated fats.     

Conjugated linoleic acid decreases prostaglandin synthesis in bovine luteal cells in vitro

Feeding conjugated linoleic acids (CLA) improves reproductive performance in dairy cows; however, the molecular mechanisms by which CLA improves reproduction are not understood. The effect of the CLA isomers, trans‐10, cis‐12 CLA and cis‐9, trans‐11 CLA on synthesis of progesterone, PGE₂, and PGF_2α, in bovine luteal cells was determined in this study. Luteal cells from three cows were cultured in medium containing 0 or 0.1 µM of trans‐10, cis‐12 CLA and cis‐9, trans‐11 CLA in varying ratios in the presence and absence of 1 µM of forskolin. Prostaglandin and progesterone concentrations were not altered by CLA isomer and ratio. Luteal cells cultured in the presence of CLA had lower PGF_2α concentrations (62.6 ± 13.4 pg/ml vs. 55.7 ± 12.2 pg/ml; P = 0.005) and, in the absence of forskolin, lower PGE₂ concentrations (65.3 ± 15.1 pg/ml vs. 32.4 ± 14.1 pg/ml; P = 0.002) in culture media, while progesterone concentrations were not altered (P = 0.63). Relative steady‐state mRNA amounts of COX‐2 (1.7‐fold decrease; P = 0.002), PGE synthase (1.5‐fold decrease; P = 0.03) and 3β‐hydroxysteroid dehydrogenase (1.6‐fold decrease; P = 0.0003) were lower in CLA‐treated cultures, but CLA did not significantly alter mRNA amounts of PGE₂ 9‐keto‐reductase, StAR, and cytochrome P450 side chain cleavage enzyme. In conclusion, a potential mechanism exists by which trans‐10, cis‐12 CLA and cis‐9, trans‐11 CLA may improve reproductive performance in dairy cows, by suppressing PGF_2α synthesis in luteal cells via attenuation of COX‐2 gene expression. Mol. Reprod. Dev. 78:328–336, 2011. © 2011 Wiley‐Liss, Inc.     

Resveratrol derivative,trans‐3,5,4′‐trimethoxystilbene,exerts antiangiogenic and vascular‐disrupting effects in zebrafish through the downregulation of VEGFR2 and cell‐cycle modulation

Angiogenesis plays an important role in the development of neoplastic diseases such as cancer. Resveratrol and its derivatives exert antiangiogenic effects, but the mechanisms of their actions remain unclear. The aim of this study was to evaluate the antiangiogenic activity of resveratrol and its derivative trans‐3,5,4′‐trimethoxystilbene in vitro using human umbilical vein endothelial cells (HUVECs) and in vivo using transgenic zebrafish, and to clarify their mechanisms of action in zebrafish by gene expression analysis of the vascular endothelial growth factor (VEGF) receptor (VEGFR2/KDR) and cell‐cycle analysis. trans‐3,5,4′‐Trimethoxystilbene showed significantly more potent antiangiogenic activity than that of resveratrol in both assays. In zebrafish, trans‐3,5,4′‐trimethoxystilbene caused intersegmental vessel regression and downregulated VEGFR2 mRNA expression. Trans‐3,5,4′‐trimethoxystilbene also induced G2/M cell‐cycle arrest, most specifically in endothelial cells of zebrafish embryos. We propose that the antiangiogenic and vascular‐targeting activities of trans‐3,5,4′‐trimethoxystilbene result from the downregulation of VEGFR2 expression and cell‐cycle arrest at G2/M phase. J. Cell. Biochem. 109: 339–346, 2010. © 2009 Wiley‐Liss, Inc.     

领春木枝叶化学成分的研究

为了研究领春木(Euptelea pleiospermum Hook.f.et Thoms)的化学成分,利用各种柱色谱及高压液相色谱等方法进行分离和纯化,根据理化性质和光谱数据分析鉴定了9个化合物。他们分别为:白桦脂酸(1);齐墩果酸(2);N-反式对羟基肉桂酰基-对羟基苯乙胺(3);N-反式阿魏酰酪胺(4);N-顺式阿魏酰酪胺(5);丁香脂素(6);N-顺式阿魏酰-3-甲氧基酪胺(7);N-反式阿魏酰-3-甲氧基酪胺(8);3-羟基-30-去甲基-20-酮基-28-羽扇豆酸(9)。所有化合物均为首次从领春木中分离得到。     

Total Synthesis of ( + )-Methyl Phaseates

( ± )-Methyl phaseates were synthesized from ( ± )-4-(6′-acetoxymethyl-2 ′,6′-dimethyl-1′-cyclohexen-1′-y1)-but-3-en-2-one (20), which was prepared from a useful terpenoid building block, ( ± )-2-hydroxymethyl-2,6-dimethyl-1-cyclohexanone (11a and 11b). Photooxidation of the cyclohexadiene intermediate (22), followed by alkaline hydrolysis and methylation, gave four stereoisomers of ( ± )-methyl phaseates: (2Z,4E)-cis form (2), (2E,4E)-cis form (24), (2Z,4E)-trans form (25) and (2E,4E)-trans form (26).     

Ruthenium(III) dimethyl sulfoxide pyridinehydroxamic acid complexes as potential antimetastatic agents: synthesis,characterisation and in vitro pharmacological evaluation

Reaction of 3-pyridinehydroxamic acid and 4-pyridinehydroxamic acid (3-pyha and 4-pyha) with either [NBu₄][RuCl₄(dmso-S)₂] or [(dmso)₂H][RuCl₄(dmso-S)₂] (dmso is dimethyl sulfoxide) in acetone afforded three new ruthenium(III) dimethyl sulfoxide pyridinehydroxamic acid complexes: [NBu₄][trans-RuCl₄(dmso-S)(4-pyha)]·CH₃COCH₃ (1), [3-pyhaH][trans-RuCl₄(dmso-S)(3-pyha)] (2) and [4-pyhaH][trans-RuCl₄(dmso-S)(4-pyha)] (3). The solid-state structure of [NBu₄][trans-RuCl₄(dmso-S)(4-pyha)]·CH₃COCH₃ (1) was determined by X-ray crystallography. 2 and 3 were pharmacologically evaluated for their in vitro cytotoxicity, their ability to inhibit cell invasion and their gelatinase activity. 2 and 3 were devoid of cytotoxicity against the cell lines tested. 2 inhibited invasion of the highly invasive MDA-MB-231 cells to a much greater extent than 3. Contrary to expectations, neither 2 nor 3 had any inhibitory effect on matrix metalloproteinase (MMP) production and/or activity and in fact 3 was found to enhance the production and/or activity of both MMP-2 and MMP-9.     

Structural and reactivity studies on the ternary system guanine/methionine/trans-[PtCl2(NH3)L] (L=NH3, quinoline): implications for the mechanism of action of nonclassical trans-platinum antitumor complexes

 The present model study explores the chemistry of methionine complexes and ternary methionine-guanine adducts formed by trans-[PtCl₂(NH₃)₂] (1) and antitumor trans-[PtCl₂(NH₃)quinoline] (2) using 1D (¹H, ¹⁹⁵Pt) and 2D NMR spectroscopy. Compound 2 was substitution inert in reactions with N-acetyl-lmethionine [AcMet(H)]. Reactions of trans-[PtCl(NO₃)(NH₃)quinoline] (5) ("monoactivated" 2) with AcMetH in water and acetone at various stoichiometries point to Pt(II)-S binding that requires prior activation of the Pt-Cl bond by labile oxygen donors. Trans-[PtCl{AcMet(H)-S}(NH₃)quinoline](NO₃) (6) and trans-[Pt{AcMet(H)-S}₂(NH₃)quinoline](NO₃)₂ (7) were isolated from these mixtures. At high [Cl^–], AcMet(H) is displaced from 7, giving 6. Frozen stereodynamics in 6 at the thioether-S and slow rotation about the Pt-N_quinoline bond result in four spectroscopically distinguishable diastereomers. ¹H NMR spectra of 7 show faster exchange dynamics due to mutual trans-labilization of the sulfur donors. Substitution of chloride in trans-[PtCl(9-EtGua)(NH₃)L]NO₃ (L=NH₃, 3; L=quinoline, 4; 9-EtGua=9-ethylguanine, which mimics the first DNA binding step of 1 and 2) by methionine-sulfur proceeded ca. 2.5 times slower for the quinoline compound. Both reactions, in turn, proved to be ca. 4 times faster than binding of a second nucleobase under analogous conditions. From the resulting mixtures the ternary adducts trans-[Pt(AcMet-S)(9-EtGua-N7)(NH₃)L](NO₃, Cl) (L=NH₃, 8; L=quinoline, 9) were isolated. A species analogous to 9 formed in a rapid reaction between 6 and 5′-guanosine monophosphate (5′-GMP). From NMR data an AMBER-based solution structure of the resulting adduct, trans-[Pt(AcMet-S)(5′-GMP-N7)(NH₃)quinoline] (10), was derived. The unusual reactivity along the N7-Pt-S axis in 8–10 resulted in partial release of both 9-EtGua and AcMet at high [Cl^–]. Possible consequences of the kinetic and structural effects (e.g., trans effect of sulfur, steric demand of quinoline) observed in these systems with respect to the (trans)formation of potential biological cross-links are discussed. Received: 25 May 1998 / Accepted: 6 August 1998     

Essential‐Oil Composition of the Needles Collected from Natural Populations of Macedonian Pine (Pinus peuce Griseb.) from the Scardo‐Pindic Mountain System

The needle‐terpene profiles of two natural Pinus peuce populations from the Scardo‐Pindic mountain system (Mt. O?ljak and Mt. Pelister) were analyzed. Among the 90 detected compounds, 87 were identified. The dominant constituents were α‐pinene (45.5%), germacrene D (11.1%), β‐pinene (10.8%), and camphene (10.3%). The following eight additional components were found to be present in medium‐to‐high amounts (0.5–10%): bornyl acetate (5.0%), β‐phellandrene (3.4%), β‐caryophyllene (2.9%), β‐myrcene (0.9%), germacrene D‐4‐ol (0.9%), tricyclene (0.7%), (E)‐hex‐2‐enal (0.7%), and bicyclogermacrene (0.6%). Although the general needle‐terpene profiles of the populations from Mt. O?ljak and Mt. Pelister were found to be similar to those of the populations from Zeletin, Sjekirica, and Mokra Gora (Dinaric Alps), principle component analysis (PCA) of eight terpenes (α‐pinene, β‐myrcene, α‐terpinolene, bornyl acetate, α‐terpinyl acetate, β‐caryophyllene, trans‐β‐farnesene, and germacrene D) in 139 tree samples suggested a divergence between the two population groups, i.e., the samples from the Scardo‐Pindic mountain system and those from the Dinaric Alps. Genetic analysis of the β‐pinene content demonstrated a partial divergence between the two geographical groups. The profiles of both population groups differed from those published for populations from the Balkan‐Rhodope mountains system (literature results), which were characterized by high contents of bornyl acetate and citronellol (Greek populations) or δ‐car‐3‐ene (Bulgarian populations).     

Enzyme mediated resolution of alcohols

Summary The racemic cis and trans isomers 1a and 1b of 2-(4-methoxybenzyl)-1-cyclohexanol were subjects of an enzyme mediated resolution via esterification in organic solvents, in which the chiral esters 2a and 2b of the corresponding alcohols 4a and 4b, and the chiral alcohols 3a and 3b were obtained. The chemical yield and enantioselectivity of this enzymatic reaction have been found to depend mainly on (a) the structure of the substrate (cis or trans), (b) temperature, (c) the nature of the enzyme selected, and (d) the nature of the solvent.     

HOPS prevents the disassembly of trans‐SNARE complexes by Sec17p/Sec18p during membrane fusion

SNARE‐dependent membrane fusion requires the disassembly of cis‐SNARE complexes (formed by SNAREs anchored to one membrane) followed by the assembly of trans‐SNARE complexes (SNAREs anchored to two apposed membranes). Although SNARE complex disassembly and assembly might be thought to be opposing reactions, the proteins promoting disassembly (Sec17p/Sec18p) and assembly (the HOPS complex) work synergistically to support fusion. We now report that trans‐SNARE complexes formed during vacuole fusion are largely associated with Sec17p. Using a reconstituted proteoliposome fusion system, we show that trans‐SNARE complex, like cis‐SNARE complex, is sensitive to Sec17p/Sec18p mediated disassembly. Strikingly, HOPS inhibits the disassembly of SNARE complexes in the trans‐, but not in the cis‐, configuration. This selective HOPS preservation of trans‐SNARE complexes requires HOPS:SNARE recognition and is lost when the apposed bilayers are dissolved in Triton X‐100; it is also observed during fusion of isolated vacuoles. HOPS thus directs the Sec17p/Sec18p chaperone system to maximize functional trans‐SNARE complex for membrane fusion, a new role of tethering factors during membrane traffic.     

Second bioluminescence‐activating component in the luminous fungus Mycena chlorophos

Mycena chlorophos is an oxygen‐dependent bioluminescent fungus. The mechanisms underlying its light emission are unknown. A component that increased the bioluminescence intensity of the immature living gills of M. chlorophos was isolated from mature M. chlorophos gills and chemically characterized. The bioluminescence‐activating component was found to be trans‐3,4‐dihydroxycinnamic acid and its bioluminescence activation was highly structure‐specific. ¹³C‐ and ¹⁸O‐labelling studies using the immature living gills showed that trans‐3,4‐dihydroxycinnamic acid was synthesized from trans‐4‐hydroxycinnamic acid in the gills by hydroxylation with molecular oxygen as well as by the general metabolism, and trans‐3,4‐dihydroxycinnamic acid did not produce hispidin (detection‐limit concentration: 10 pmol/1 g wet gill). Addition of 0.01 mM hispidin to the immature living gills generated no bioluminescence activation. These results suggested that the prompt bioluminescence activation resulting from addition of trans‐3,4‐dihydroxycinnamic acid could not be attributed to the generation of hispidin. Copyright © 2016 John Wiley & Sons, Ltd.     

Polypyrimidine tract‐binding protein is required for the repression of gene expression by all‐trans retinoic acid

All‐trans retinoic acid is a key regulator of early development. High concentrations of retinoic acid interfere with differentiation and migration of neural crest cells. Here we report that a dinucleotide repeat in the cis‐element of Snail2 (previously known as Slug) gene plays a role in repression by all‐trans retinoic acid. We analyzed the cis‐acting regulatory regions of the Xenopus Snail2 gene, whose expression is repressed by all‐trans retinoic acid. The analysis identified a TG/CA repeat as a necessary element for the repression. By performing a yeast one‐hybrid screen, we found that a polypyrimidine tract‐binding protein (PTB), which is known to be a regulator of the alternative splicing of pre‐messenger RNA, binds to the TG/CA repeat. Overexpression and knockdown experiments for PTB in HEK293 cells and Xenopus embryos indicated that PTB is required for repression by retinoic acid. The green fluorescent protein‐PTB fusion protein was localized in the nucleus of 293T cells. In situ hybridization for PTB in Xenopus embryos showed that PTB is expressed at the regions including neural crest at the early stages. Our results indicate that PTB plays a role in the repression of gene expression by retinoic acid through binding to the TG/CA repeats.     

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

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/Et₂O 1 : 2 (v/v) and B: CH₂Cl₂) 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.