Field response of the northern spruce bark beetle Ips duplicatus (Sahlberg) (Coleoptera: Curculionidae,Scolytinae) to different combinations of synthetic pheromone with (−)‐α‐pinene and (+)‐limonene

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Abundance of volatile organic compounds in white ash phloem and emerald ash borer larval frass does not attract Tetrastichus planipennisi in a Y‐tube olfactometer

Many natural enemies employ plant‐ and/or herbivore‐derived signals for host/prey location. The larval parasitoid Tetrastichus planipennisi Yang (Hymenoptera: Eulophidae) is 1 of 3 biocontrol agents currently being released in an effort to control the emerald ash borer (EAB), Agrilus planipennis Fairmaire (Coloeptera: Burprestidae) in North America. To enhance its efficiency, allelochemicals that attract it need to be assessed. In this study, ash phloem volatile organic compounds (VOCs) of black, green, and white ash, and EAB larval frass were compared. Foraging behavior of T. planipennisi females in response to VOCs of white ash or frass from EAB larvae feeding on white ash phloem was tested using a Y‐tube olfactometer. Results indicated that the 3 ash species had similar VOC profiles. EAB larval frass generally contained greater levels of VOCs than phloem. Factor analysis indicated that the 11 VOCs could be broadly divided into 2 groups, with α‐bisabolol, β‐caryophyllene, (E)‐2‐hexenal, (Z)‐3‐hexenal, limonene, methyl benzoate, methyl indole‐3‐acetic acid, methyl jasmonate, methyl salicylate as the first group and the rest (i.e., methyl linoleate and methyl linolenate) as a second. Abundance of VOCs in white ash phloem tissue and frass, nevertheless, did not attract T. planipennisi females. The concealed feeding of EAB larvae might explain the selection for detectable and reliable virbrational signals, instead of undetectable and relatively unreliable VOC cues from phloem and frass, in short‐range foraging by T. planipennisi. Alternatively, it is possible that T. planipennisi is not amenable to the Y‐tube olfactometer assay employed.     

Electrophysiological and laboratory behavioral responses of a leaf beetle pest of elm,Ambrostoma quadriimpressum,to selected plant volatiles and essential oils

The leaf beetle Ambrostoma quadriimpressum Motschulsky (Coleoptera: Chrysomelidae) is distributed in China, Siberia, and elsewhere in northeastern Asia. This pest feeds only on buds and leaves of elm trees (Ulmaceae) and inhibits elm trees sprouting, increasing the risk of damage and destruction by other pests. We investigated selected plant compounds that could be used for the development of semiochemical‐based push‐pull methods for the control of this elm pest. Electroantennogram (EAG), Y‐tube olfactometer, and wind tunnel bioassays were conducted to test the electrophysiological and behavioral response of A. quadriimpressum to nine individual volatiles and five essential oils. Individual volatiles and essential oils were selected based on their activity against insects in previous studies. The individual volatiles and essential oils were dissolved in dichloromethane and adsorbed by filter paper. Using a pipette, odor stimuli were delivered as 0.5‐s puffs of air into a continuously humidified air stream in the odor delivery tube at 400 ml per min. Ambrostoma quadriimpressum adults display strong EAG responses to l mol l^?1 isoeugenol, (1R)‐(+)‐α‐pinene, 1% pepper oil (derived from the pericarp of Piper chinense Miq.), and peppermint oil [derived from the aerial parts of Mentha haplocalyx (Briq.)] compared to the control. In behavioral assays conducted using a Y‐tube olfactometer and a wind tunnel, adult beetles were attracted by (1R)‐(+)‐α‐pinene but repelled by 0.1% pepper oil. The results provide a basis for the development of a ‘push‐pull’ strategy to manage A. quadriimpressum.     

Orientation of colonized sand flies Phlebotomus papatasi,P. duboscqi,and Lutzomyia longipalpis (Diptera: Psychodidae) to diverse honeys using a 3‐chamber in‐line olfactometer

A 3‐chamber in‐line olfactometer designed for use with sand flies is described and tested as a high‐throughput method to screen honeys for attractiveness to Phlebotomus papatasi (four geographic isolates), P. duboscqi (two geographic isolates), and Lutzomyia longipalpis maintained in colonies at the Walter Reed Army Institute of Research. A diversity of unifloral honey odors were evaluated as a proxy for the natural floral odors that sand flies may use in orientation to floral sugar sources in the field. In the 3‐chamber in‐line olfactometer, the choice modules come directly off both sides of the release area instead of angling away as in the Y‐tube olfactometer. Of the 25 honeys tested, five had a significant attraction for one or more of the sand fly isolates tested. This olfactometer and high‐throughput method has utility for evaluating a diversity of natural materials with unknown complex odor blends that can then be down‐selected for further evaluation in wind tunnels and/or field scenarios.     

Chemical Composition of the Essential Oils from Different Morphological Parts of Pinus cembra L.

The essential oils from needles, twigs, bark, wood, and cones of Pinus cembra were analyzed by GC‐FID, GC/MS, and ¹H‐NMR spectroscopy. More than 130 compounds were identified. The oils differed in the quantitative composition. The principal components of the oil from twigs with needles were α‐pinene (36.3%), limonene (22.7%) and β‐phellandrene (12.0%). The needle oil was dominated by α‐pinene (48.4%), whereas in the oil from bark and in the oil from twigs without needles there were limonene (36.2% and 33.6%, resp.) and β‐phellandrene (18.8% and 17.1%, resp.). The main constituents of the wood oil as well as cone oil were α‐pinene (35.2% and 39.0%, resp.) and β‐pinene (10.4% and 18.9%, resp.). The wood oil and the cone oil contained large amounts of oxygenated diterpenes in comparison with needle, twig, and bark oils.     

Enhanced diastereoselective synthesis of t‐Butyl 6‐cyano‐(3R,5R)‐dihydroxyhexanoate by using aldo‐keto reductase and glucose dehydrogenase co‐producing engineered Escherichia coli

t‐Butyl 6‐cyano‐(3R,5R)‐dihydroxyhexanoate ((3R,5R)‐ 2 ) is a key chiral diol precursor of atorvastatin calcium (Lipitor®). We have constructed a Kluyveromyces lactis aldo‐keto reductase mutant KlAKR‐Y295W/W296L (KlAKRm) by rational design in previous research, which displayed high activity and excellent diastereoselectivity (de_p > 99.5%) toward t‐butyl 6‐cyano‐(5R)‐hydroxy‐3‐oxohexanoate ((5R)‐ 1 ). To realize in situ cofactor regeneration, a robust KlAKRm and Exiguobacterium sibiricum glucose dehydrogenase (EsGDH) co‐producer E. coli BL 21(DE3) pETDuet‐esgdh (MCS1)/pET‐28b (+)‐klakrm was constructed in this work. Under the optimized conditions, AKR and GDH activities of E. coli BL 21(DE3) pETDuet‐esgdh (MCS1)/pET‐28b (+)‐klakrm peaked at 249.9 U/g DCW (dry cellular weight) and 29100 U/g DCW, respectively. It completely converted (5R)‐ 1 at substrate loading size of up to 60.0 g/L (5R)‐ 1 in the absence of exogenous NADH, which was one‐fifth higher than that of the separately prepared KlAKRm and EsGDH under the same conditions. In this manner, a biocatalytic process for (3R,5R)‐ 2 with productivity of 243.2 kg/m³ d was developed. Compared with the combination of separate expressed KlAKRm with EsGDH, co‐expression of KlAKRm and EsGDH has the advantages of alleviating cell cultivation burden and elevating substrate load. © 2017 American Institute of Chemical Engineers Biotechnol. Prog., 33:1235–1242, 2017     

Effects of plant volatiles on electrophysiological and behavioral responses of Cryptorrhynchus lapathi

Electroantennogram (EAG), Y‐tube olfactometer, and wind tunnel bioassays were conducted to test the electrophysiological and behavioral responses of Cryptorrhynchus lapathi L. (Coleoptera: Curculionidae) to six individual volatiles and seven essential oils (compounded volatiles). The aim of this study was to select effective plant compounds that can be used in the development of semiochemical‐based push–pull methods for the control of this harmful insect. Male and female C. lapathi displayed strong EAG responses to linoleic acid, α‐pinene, (Z)‐3‐hexen‐1‐ol, geraniol, turpentine oil, and salicylaldehyde. Y‐tube olfactometer assays indicated that salicylaldehyde and α‐pinene elicited strong repellent effects on female C. lapathi. Linoleic acid and (Z)‐3‐hexen‐1‐ol showed greater luring effects on male and female C. lapathi compared with the control. Turpentine oil was stronger repellent, and geraniol showed stronger luring effects on male C. lapathi than the control. Wind tunnel assays with both male and female C. lapathi indicated that salicylaldehyde, α‐pinene, and turpentine oil elicited repellent effects compared with the control. Linoleic acid, (Z)‐3‐hexen‐1‐ol, and geraniol were stronger lures of both male and female C. lapathi than the control. These results provide a basis for the further development of C. lapathi luring and repellent agents.     

Effects of learning experience on behaviour of the generalist parasitoid Sclerodermus pupariae to novel hosts

Massicus raddei Blessig (Coleoptera: Cerambycidae), also referred to as the oak long‐horned beetle (OLB), is a non‐natural host for the generalist parasitoid Sclerodermus pupariae Yang et Yao (Hymenoptera: Bethylidae). To determine whether this generalist parasitoid might be a suitable agent for the control of OLB, the adaptive learning experience of adult female parasitoids to OLB larvae was investigated in the laboratory. A Y‐tube olfactometer bioassay was used to examine the effects of adaptive learning experience on the foraging ability of parasitoids for OLB larvae. The results indicated that parasitoids were significantly attracted by the volatiles of ash bark, Fraxinus velutina, with emerald ash borer (EAB), Agrilus planipennis Fairmaire (Coleoptera: Buprestidae) larvae and larval frass, after exposure to ash bark mixed with EAB larval frass (learning condition A). In contrast, after exposure to oak bark, Quercus liaotungensis, mixed with OLB larval frass (learning condition C), parasitoids showed significant preference for the volatiles of oak bark with OLB larvae and larval frass. On the basis of the results of no‐choice tests, we found that parasitoids exposed to learning condition C had greater paralysis efficiency and higher OLB larvae parasitism rates than those exposed to learning condition A or no experience. Furthermore, parasitoids fed on OLB larvae in learning condition C had significantly greater paralysis efficiency and higher OLB larvae parasitism rates than other parasitoids tested. Parasitoids fed on EAB larvae in learning condition A had the lowest paralysis efficiency and OLB larvae parasitism rates among the parasitoids tested. These findings suggested that adaptive learning significantly enhanced the ability of a generalist parasitoid to utilize a novel host. This may provide a new approach to controlling non‐natural hosts using generalist parasitoids.     

Characterization of monoterpene biotransformation in two pseudomonads

Aims: To study the metabolic profile of Pseudomonas rhodesiae and Pseudomonas fluorescens in water–organic solvent systems using terpene substrates for both growth and biotransformation processes and to determine the aerobic or anaerobic status of these degradation pathways. Materials and Methods: Substrates from pinene (α‐pinene, α‐pinene oxide, β‐pinene, β‐pinene oxide, turpentine) and limonene (limonene, limonene‐1,2‐oxide, orange peel oil) families were tested. For the bioconversion, the terpene‐grown biomass was concentrated and used either as whole cells or as a crude enzymatic extract. Conclusion: Pseudomonas rhodesiae was the most suitable biocatalyst for the production of isonovalal from α‐pinene oxide and did not metabolize limonene. Pseudomonas fluorescens was a more versatile micro‐organism and metabolized limonene in two different ways. The first (anaerobic, cofactor‐independent, noninducible) allowed limonene elimination by synthesizing α‐terpineol. The second (aerobic, cofactor‐dependent) involved limonene‐1,2‐oxide as an intermediate for energy production through a β‐oxidation process. Significance and Impact of the Study: Enzymatic isomerization of β‐ to α‐pinene was described for the first time for both strains. Alpha‐terpineol production by P. fluorescens was very efficient and appeared as a promising alternative for the commercial production of this bioflavour.     

Examination of the active secondary structure of the peptide 101.10, an allosteric modulator of the interleukin‐1 receptor,by positional scanning using β‐amino γ‐lactams

The relationship between the conformation and biological activity of the peptide allosteric modulator of the interleukin‐1 receptor 101.10 (D ‐Arg‐D ‐Tyr‐D ‐Thr‐D ‐Val‐D ‐Glu‐D ‐Leu‐D ‐Ala‐NH₂) has been studied using (R)‐ and (S)‐Bgl residues. Twelve Bgl peptides were synthesized using (R)‐ and (S)‐cyclic sulfamidate reagents derived from L ‐ and D ‐aspartic acid in an optimized Fmoc‐compatible protocol for efficient lactam installment onto the supported peptide resin. Examination of these (R)‐ and (S)‐Bgl 101.10 analogs for their potential to inhibit IL‐1β‐induced thymocyte cell proliferation using a novel fluorescence assay revealed that certain analogs exhibited retained and improved potency relative to the parent peptide 101.10. In light of previous reports that Bgl residues may stabilize type II′β‐turn‐like conformations in peptides, CD spectroscopy was performed on selected compounds to identify secondary structure necessary for peptide biological activity. Results indicate that the presence of a fold about the central residues of the parent peptide may be important for activity. Copyright © 2011 European Peptide Society and John Wiley & Sons, Ltd.     

The Asymmetry of (−)α‐Pinene as Revealed from its Raman Optical Activity Spectrum

An algorithm is employed to retrieve the differential bond polarizabilities of the C‐C bonds from the Raman optical activity (ROA) spectrum of (?)α‐pinene. (?)α‐pinene possesses two asymmetric centers (carbon atoms) and a local mirror symmetry. These differential bond polarizabilities show the characteristics of the asymmetry around the asymmetric carbons with respect to the mirror reflection. This analysis is accompanied along with the ROA mode signatures and the calculated β(G ')² and β(A)²which show the ROA coupling mechanisms involving the electric/magnetic dipoles and the electric dipole/quadrupole, respectively. Chirality 25:600–605, 2013. © 2013 Wiley Periodicals, Inc.     

松墨天牛成虫对幼虫虫粪挥发性物质的触角电位反应及林间驱避试验

为了研制松墨天牛Monochamus alternatus Hope驱避剂,本文利用触角电位技术和田间试验的方法研究了松墨天牛雌雄成虫对幼虫虫粪挥发性物质的触角电位反应及幼虫虫粪己烷提取物、合成化合物混合物的林间驱避作用。结果表明：α-蒎烯、β-蒎烯、3-蒈烯、柠檬烯和长叶烯均能引起松墨天牛雌雄成虫一定的触角电生理反应,而4-甲基-2,6-二叔丁基苯酚不能引起松墨天牛雌雄成虫的触角电生理反应。林间驱避试验结果说明,幼虫虫粪的己烷提取物处理过的树干上的刻槽数明显少于对照树干上的刻槽数,二者具有极显著差异;有合成化合物的混合物存在的诱捕器诱捕到的雌虫数（平均值3.80±1.02）与对照诱捕到的雌虫数（平均值16.80±1.16）差异极显著。结果显示α-蒎烯、β-蒎烯、3-蒈烯、柠檬烯、长叶烯和4-甲基-2,6-二叔丁基苯酚的混合物对松墨天牛雌虫具有驱避作用,有望开发出一类新的驱避剂。     

Synthesis of enantiomers of exo‐2‐norbornyl‐N‐n‐butylcarbamate and endo‐2‐norbornyl‐N‐n‐butylcarbamate for stereoselective inhibition of acetylcholinesterase

The acetylcholinesterase inhibition by enantiomers of exo‐ and endo‐2‐norbornyl‐N‐n‐butylcarbamates shows high stereoselelectivity. For the acetylcholinesterase inhibitions by (R)‐(+)‐ and (S)‐(?)‐exo‐2‐norbornyl‐N‐n‐butylcarbamates, the R‐enantiomer is more potent than the S‐enantiomer. But, for the acetylcholinesterase inhibitions by (R)‐(+)‐ and (S)‐(?)‐endo‐2‐norbornyl‐N‐n‐butylcarbamates, the S‐enantiomer is more potent than the R‐enantiomer. Optically pure (R)‐(+)‐exo‐, (S)‐(?)‐exo‐, (R)‐(+)‐endo‐, and (S)‐(?)‐endo‐2‐norbornyl‐N‐n‐butylcarbamates are synthesized from condensations of optically pure (R)‐(+)‐exo‐, (S)‐(?)‐exo‐, (R)‐(+)‐endo‐, and (S)‐(?)‐endo‐2‐norborneols with n‐butyl isocyanate, respectively. Optically pure norborneols are obtained from kinetic resolutions of their racemic esters by lipase catalysis in organic solvent. Chirality 2010. © 2009 Wiley‐Liss, Inc.     

Resolution of 1‐n‐Butyl‐3‐Methyl‐3‐Phospholene 1‐Oxide With TADDOL Derivatives and Calcium Salts of O,O'‐Dibenzoyl‐(2R,3R)‐ or O,O'‐di‐p‐Toluoyl‐(2R,3R)‐tartaric Acid

The resolution methods applying (?)‐(4R,5R)‐4,5‐bis(diphenylhydroxymethyl)‐2,2‐dimethyldioxolane (“TADDOL”), (?)‐(2R,3R)‐α,α,α',α'‐tetraphenyl‐1,4‐dioxaspiro[4.5]decan‐2,3‐dimethanol (“spiro‐TADDOL”), as well as the acidic and neutral Ca²⁺ salts of (?)‐O,O'‐dibenzoyl‐ and (?)‐O,O'‐di‐p‐toluoyl‐(2R,3R)‐tartaric acid were extended for the preparation of 1‐n‐butyl‐3‐methyl‐3‐phospholene 1‐oxide in optically active form. In one case, the intermediate diastereomeric complex could be identified by single‐crystal X‐ray analysis. The absolute P‐configuration of the enantiomers of the phospholene oxide was also determined by comparing the experimentally obtained and calculated CD spectra. Chirality 26:174–182, 2014. © 2014 Wiley Periodicals, Inc.     

The social wasp Polybia fastidiosuscula Saussure (Hymenoptera: Vespidae) uses herbivore‐induced maize plant volatiles to locate its prey

Social wasps in the Polybia genus are important for use as pest‐control agents in agricultural systems. The objective of this study was to investigate the behavioural responses of Polybia fastidiosuscula Saussure (Hymenoptera: Vespidae) to volatiles from maize, both constitutive volatiles and those induced by the herbivory of Spodoptera frugiperda (JE Smith) (Lepidoptera: Noctuidae). To assess the behavioural response of P. fastidiosuscula to S. frugiperda larvae, undamaged plants, S. frugiperda‐damaged plants, mechanically damaged plants, mechanically damaged plants plus regurgitant from larvae and extracts from various treatments, bioassays were conducted in a Y‐olfactometer. In addition, the volatiles from plants subjected to different treatments were collected via aeration, and they were quantified and identified. The wasps showed a greater preference for plants with damage induced either by larval feeding or by being mechanically damaged plus regurgitant than for undamaged plants or either larvae alone or mechanically damaged plants. Wasps were more attracted to extracts from plants + S. frugiperda larvae and to an extract from mechanically damaged plants + the regurgitant of larvae compared to hexane. The primary compounds induced by herbivory for 5–6 h after the beginning of the damage or regurgitant treatment were identified as α‐pinene, β‐myrcene, (Z)‐3‐hexenyl acetate, limonene, (E)‐ocimene, linalool, DMNT, (E)‐β‐farnesene, TMTT and indole. The results presented here show that the social wasp P. fastidiosuscula uses herbivore‐induced plant volatiles from maize to locate its prey.     

Olfactory cues used in host‐habitat location and host location by the parasitoid Cotesia urabae

There is a growing body of evidence that many hymenopteran parasitoids make use of olfaction as the primary mechanism to detect and locate hosts. In this study, a series of bioassays was conducted to investigate the orientation behaviour of the gum leaf skeletonizer larval parasitoid Cotesia urabae Austin & Allen (Hymenoptera: Braconidae) in both Y‐tube and four‐arm olfactometers. In a Y‐tube olfactometer, male C. urabae were attracted only to virgin conspecific females. Host‐plant leaves, damaged leaves, host larvae, and host larvae feeding on leaves were highly attractive to female C. urabae, whereas host frass and conspecific males were not. The multiple‐comparison bioassay conducted in a four‐arm olfactometer clearly indicates that C. urabae females were significantly more attracted to the host Uraba lugens Walker (Lepidoptera: Nolidae) larvae feeding on Eucalyptus fastigata H Deane & Maiden (Myrtaceae) leaves than to any other of the odour sources tested. The results of this study show that C. urabae individuals responded to chemical cues specific to the host plant and target host insect, and support hypotheses that unreliable cues are not utilized for host location by specific natural enemies.     

Electroantennogram responses of a parasitic wasp, Microplitis croceipes, to host-related volatile and anthropogenic compounds

The parasitic wasp Microplitis croceipes (Cresson) (Hymenoptera: Braconidae) showed its own characteristic electroantennogram (EAG) response profiles to 13 host‐related (cis‐3‐hexenol, α‐pinene (R)‐(+)‐limonene (S)‐(–)‐limonene, trans‐β‐ocimene (±)‐linalool, (–)‐trans‐caryophyllene, α‐humulene, nerolidol, trans‐nerolidol, cis‐nerolidol, methyl jasmonate and indole) and four anthropogenic (2‐diisopropylaminoethanol, 2,2′‐thiodiethanol, 2‐methyl‐5‐nitroaniline and cyclohexanone) volatile compounds. These profiles were similar between males and females except for 2‐diisopropylaminoethanol, which elicited significantly larger EAG responses in males. Among the compounds tested, cis‐3‐hexenol, linalool and cyclohexanone elicited the largest EAG responses. EAG responses were not influenced by the age of wasps between 1 and 13 days after emergence. EAG responses were dose‐dependent, and highly EAG‐active compounds elicited significant EAG responses with less than 10 μg of the compounds at source. Quantification of compounds released from an odour cartridge indicates that release rate is highly dependent on the chemical nature of stimuli, showing up to 10 000‐fold differences in the amount released between different compounds when the same amount was loaded in the odour cartridge. Wasps having undergone a behavioural training regime to be attracted to either cyclohexanone or methyl jasmonate did not show any differences in EAG responses from those of untrained wasps.     

Chemical Variability of Cleistopholis patens (Benth.) Engl. et Diels Leaf Oil from Ivory Coast

The chemical composition of 48 leaf oil samples isolated from individual plants of Cleistopholis patens (Benth .) Engl. et Diels harvested in four Ivoirian forests was investigated by GC‐FID (determination of retention indices), GC/MS, and ¹³C‐NMR analyses. The main components identified were β‐pinene (traces–59.1%), sabinene (traces–54.2%), (E)‐β‐caryophyllene (0.3–39.3%), linalool (0.1–38.5%), (E)‐β‐ocimene (0.1–33.2%), germacrene D (0.0–33.1%), α‐pinene (0.1–32.3%), and germacrene B (0–21.2%). The 48 oil compositions were submitted to hierarchical clustering and principal components analyses, which allowed the distinction of three groups within the oil samples. The oil composition of the major group (Group I, 33 samples) was dominated by (E)‐β‐caryophyllene and linalool. The oils of Group II (eight samples) contained mainly β‐pinene and α‐pinene, while those of Group III (seven samples) were dominated by sabinene, limonene, and β‐phellandrene. Moreover, the compositions of the Ivoirian C. patens leaf oils differed from those of Nigerian and Cameroonian origins.     

Optically Active α‐Phenylethylamine as Efficient Organocatalyst in the Solvent‐free Reactions Between 2,3‐Butanedione and Conjugated Nitroolefins

(R)‐(+) and (S)‐(?)‐1‐phenylethylamine have been shown to promote highly diastereoselective and complementary enantioselective formal [3 + 2]carbocyclization reactions between 2,3‐butanedione and conjugated nitroalkenes with formation of enantiomerically rich 2‐hydroxy‐3‐nitrocyclopentanone derivatives. The reactions were carried out both in solvent and under solvent‐free conditions. The absolute configurations of the products were assigned by X‐ray and circular dichroism spectra analyses. Chirality 24:1005–1012, 2012. © 2012 Wiley Periodicals, Inc.     

Determination of the enantiomeric purity of the selective dopamine transporter inhibitor (+)‐R,R‐4‐(2‐benzhydryloxyethyl)‐1‐(4‐fluorobenzyl)piperidin‐3‐ol

(+)‐R ,R ‐D‐84 ((+)‐R ,R ‐4‐(2‐benzhydryloxyethyl)‐1‐(4‐fluorobenzyl)piperidin‐3‐ol) is a promising pharmacological tool for the dopamine transporter (DAT), due to its high affinity and selectivity for this target. In this study, an analytical method to ascertain the enantiomeric purity of this compound was established. For this purpose, a high‐performance liquid chromatographic (HPLC) method, based on a cellulose derived chiral stationary phase (CSP) was developed. The method was characterized concerning its specificity, linearity, and range. It was shown that the method is suitable to determine an enantiomeric excess of up to 99.8%. With only a few adjustments, this analytical CSP‐HPLC method is also well suited to separate (+)‐R ,R ‐D‐84 from its enantiomer in a semipreparative scale.