<Emphasis Type="Italic">E</Emphasis>-2-Ethylhexenal, <Emphasis Type="Italic">E</Emphasis>-2-Ethyl-2-Hexenol,Mellein, and 4-Hydroxymellein in <Emphasis Type="Italic">Camponotus</Emphasis> Species from Brunei

E-2-ethyl-2-hexen-1-ol (1), mellein (4), and 4-hydroxymellein (5) were identified as the major volatile compounds in the head and/or thorax of Camponotus quadrisectus. Neither 1 nor 5 have been previously detected in insects. Also identified were small amounts of m-cresol (2) and 6-methyl salicylic acid (3). E-2-ethylhexenal (6) and small amounts of 3 were identified in heads of Camponotus irritibilis from Kuala Belalong, Brunei. Compounds 2–4 occur in other Bornean camponotines with hypertrophied mandibular glands, and 4 is widespread in the tribe. The possibility of semiochemical parsimony (multiple functions) for these mandibular gland compounds is reviewed in the context of existing data on mandibular gland products of other camponotines, reported biological activities of the compounds, and secondary loss of metapleural glands in this ant group.     

Identification of Novel Acetylenic Alcohols and a New Dihydrothiopyranone from the Tropical Sponge <Emphasis Type="Italic">Reniochalina</Emphasis> sp.

Two new acetylenic alcohols (1–2) and a new dihydrothiopyranone (3) were isolated from the tropical sponge Reniochalina sp. Their structures were determined by spectroscopic and chemical methods to be (3R)-hydroxyoctatriacont-(4E)-en-1-yne (1), 5-hydroxyheptatriacont-(3Z)-en-1-yne (2) and 2-hexadecyl-2,3-dihydrothiopyran-4-one (3). The acetylenic alcohol (1) exhibited significant growth inhibitory effect against human tumor cell lines.     

Two Novel Ceramides with a Phytosphingolipid and a Tertiary Amide Structure from <Emphasis Type="Italic">Zephyranthes candida</Emphasis>

Two novel ceramides, Candidamide A (1) with a phytosphingolipid structure, and Candidamide B (2) with a tertiary amide structure, together with 12 known compounds (3–14) have been isolated from the bulbs of Zephyranthes candida, The structures of 1 and 2 have been elucidated to be 1,3,5,6-tetrahydroxy-2-(2′-hydroxytetracosanoyl amino)-8-(E)-octadecadiene (1) and (2S,3S,4R,8E,2′R)-2-[N-(2′-hydroxyoctadecanoyl)-N-(1′′,2′′-dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol (2) on the basis of spectroscopic evidence including IR, MS, NMR (¹H-NMR, ¹³C-NMR, DEPT, ¹H–¹H COSY, HSQC, HMBC). The known compounds were identified as (2S)-3′,7-dihydroxy-4′-methoxyflavan (3), (2S)-4′-hydroxy-7-methoxyflavan (4), (2S)-4′,7-dihydroxyflavan (5), 7-hydroxy-3′, 4′-methylenedioxyflavan (6), ambrettolide (7), β-sitostero1 (8), β-daucosterin (9), rutin (10), pancratistatin (11), lycorine (12), haemanthidine (13), and haemanthamine (14). In the antimicrobial assay, candidamide A (1) and candidamide B (2) displayed moderate activities against bacteria Staphylococcus aureus and Escherichia coli, and fungi Aspergillus niger, Candida albicans and Trichophyton rubrum.     

Male-Produced Aggregation Pheromones of the Cerambycid Beetles <Emphasis Type="Italic">Xylotrechus colonus</Emphasis> and <Emphasis Type="Italic">Sarosesthes fulminans</Emphasis>

Adults of both sexes of the cerambycid beetles Xylotrechus colonus (F.) and Sarosesthes fulminans (F.) were attracted to odors produced by male conspecifics in olfactometer bioassays. Analyses of headspace volatiles from adults revealed that male X. colonus produced a blend of (R)- and (S)-3-hydroxyhexan-2-one and (2 S,3 S)- and (2R,3R)-2,3-hexanediol, whereas male S. fulminans produced (R)-3-hydroxyhexan-2-one and (2 S,3R)-2,3-hexanediol. All of these compounds were absent in the headspace of females. Two field bioassays were conducted to confirm the biological activity of the synthesized pheromones: (1) enantiomerically enriched pheromone components were tested singly and in species-specific blends and (2) four-component mixture of racemic 3-hydroxyhexan-2-one plus racemic 2-hydroxyhexan-3-one and the four-component blend of the stereoisomers of 2,3-hexanediols were tested separately and as a combined eight-component blend. In these experiments, adult male and female X. colonus were captured in greatest numbers in traps baited with the reconstructed blend of components produced by males, although significant numbers were also captured in traps baited with (R)-3-hydroxyhexan-2-one alone or in blends with other compounds. Too few adult S. fulminans were captured for a statistical comparison among treatments, but all were caught in traps baited with lures containing (R)-3-hydroxyhexan-2-one. In addition to these two species, adults of two other species of cerambycid beetles, for which pheromones had previously been identified, were caught: Neoclytus a. acuminatus (F.) and its congener Neoclytus m. mucronatus (F.). Cross-attraction of beetles to pheromone blends of other species, and to individual pheromone components that are shared by two or more sympatric species, may facilitate location of larval hosts by species that compete for the same host species.     

Isolation of Three Diterpenoid Acids from Sunflowers,as Oviposition Stimulants for the Banded Sunflower Moth, <Emphasis Type="Italic">Cochylis hospes</Emphasis>

The banded sunflower moth (BSFM), Cochylis hospes Walshingham (Lepidoptera: Cochylidae) is a specialist insect, the larvae of which feed on sunflowers, Helianthus spp., and a few other species of Compositae. It is one of the most important pests of sunflower in the USA. Previous work on H. annuus, the cultivated sunflower, revealed two diterpenoids that function as oviposition stimulants for female BSFM, and that other, more polar compounds also stimulated oviposition. Using a bioassay-guided approach, we isolated three additional diterpenoids, grandifloric acid (1), 15β-hydroxy-ent-trachyloban-19-oic acid (2), and 17-hydroxy-16α-ent-kauran-19-oic acid (3), from polar fractions of pre-bloom sunflower head extracts. In laboratory bioassays, purified natural samples of each of these compounds stimulated oviposition by female BSFM. Structure–activity relationships of the five diterpenoids known to stimulate oviposition by female BSFM are discussed.     

New ceramides from <Emphasis Type="Italic">Rantherium suaveolens</Emphasis>

A mixture of five new ceramides was isolated from the aerial parts of Rantherium suaveolens and characterized by spectroscopic and chemical methods. Their structures were elucidated by spectroscopic and chemical methods as (2S, 3S, 4R, 2′R, 14E)-2-(2′-hydroxydocosanoylamino)-14-octadecene-1,3,4-triol (1), (2S,3S,4R,2′R, 14F)-2-(2′-hydroxytricosanoylamino)-14-octadecene-1,3,4-triol (2), (2S,3S,4R,2′R,14F)-2-(2′-hydroxytetracosanoylamino)-14-octadecene-1,3,4-triol (3), (2S,3S,4R,2′R,14E)-2-(2′-hydroxypentacosanoylamino)-14-octadecene-1,3,4-triol (4), and (2S,3S,4R,2′R,14E)-2-(2′-hydroxyhexacosanoylamino)-14-octadecene-1,3,4-triol (5).     

New cerebrosides from the basidiomycete <Emphasis Type="Italic">Cortinarius tenuipes</Emphasis>

Five cerebrosides (1–5), including three new ones named cortenuamide A (1), cortenuamide B (2), and cortenuamide C (3), were isolated from the fruiting bodies of the basid-iomycete Cortinarius tenuipes. The structures of those compounds were elucidated as (4E,8E)-N-d-2′-hydroxytetracosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (1), (4E,8E)-N-d-2′-hydroxytricosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8 sphingadienine (2), (4E, 8E)-N-d-2′-hydroxydocosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (3), (4E, 8E)-N-d-2′-hydroxyoctadecanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (4), and (4E, 8E)-N-d-2′-hydroxypalmitoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (5) by spectral and chemical methods.     

Identification of Sex Pheromone Components of the Hessian Fly, <Emphasis Type="Italic">Mayetiola destructor</Emphasis>

Coupled gas chromatographic (GC)–electroantennographic detection (EAD) analyses of ovipositor extract of calling Hessian fly, Mayetiola destructor, females revealed that seven compounds elicited responses from male antennae. Four of the compounds—(2S)-tridec-2-yl acetate, (2S,10Z)-10-tridecen-2-yl acetate, (2S,10E)-10-tridecen-2-yl acetate, and (2S,10E)-10-tridecen-2-ol—were identified previously in female extracts. Two new EAD-active compounds, (2S,8Z,10E)-8,10-tridecadien-2-yl acetate and (2S,8E,10E)-8,10-tridecadien-2-yl acetate, were identified by GC–mass spectroscopy (MS) and the use of synthetic reference samples. In a Y-tube bioassay, a five-component blend (1 ng (2S)-tridec-2-yl acetate, 10 ng (2S,10E)-10-tridecen-2-yl acetate, 1 ng (2S,10E)-10-tridecen-2-ol, 1 ng (2S,8Z,10E)-8,10-tridecadien-2-yl acetate, and 1 ng (2S,8E,10E)-8,10-tridecadien-2-yl acetate) was as attractive to male Hessian flies as a similar amount of female extract (with respect to the main compound, (2S,10E)-10-tridecen-2-yl acetate). The five-component blend was more attractive to male flies than a three-component blend lacking the two dienes. Furthermore, the five-component blend was more attractive than a blend with the same compounds but that contained one tenth the concentration of (2S,8E,10E)-8,10-tridecadien-2-yl acetate (more accurately mimicking the ratios found in female extract). This suggests that the ratios emitted by females might deviate from those in gland extracts. In a field-trapping experiment, the five-component blend applied to polyethylene cap dispensers in a 100:10 μg ratio between the main component and each of the other blend components attracted a significant number of male Hessian flies. Also, a small-plot field test demonstrated the attractiveness of the five-component blend to male Hessian flies and suggests that this pheromone blend may be useful for monitoring and predicting Hessian fly outbreaks in agricultural systems.     

Chemistry of <Emphasis Type="Italic">Glossodoris</Emphasis> Nudibranchs: Specific Occurrence of 12-Keto Scalaranes

With the aim of establishing whether the oxidation of the tricyclic carbon skeleton of scalaradial (1) is specific to Glossodoris mollusks, the chemical investigation of specimens of Glossodoris pallida from two distinct geographical areas (China and Guam) and of Glossodoris vespa and Glossodoris averni from Eastern Australia was performed. 12-Deacetoxy-12-oxo-scalaradial (4), recently reported from another Glossodoris nudibranch, was the main metabolite of G. pallida from China, G. vespa, and G. averni. A series of scalarane compounds 3 and 5–11, including the unprecedented 12,16-deacetoxy-12-oxo-scalarafuran 5, was isolated from the mollusks. Interestingly, a population of G. pallida from Guam displayed a different scalarane pattern that was characterized by scalaradial (1), deacetyl scalaradial (2), and deoxoscalarin (3), thus confirming previous reports. The specific occurrence of 12-keto-derivatives in some nudibranchs of the genus Glossodoris is discussed.     

Two New Monogalactosyl Diacylglycerols from Brown Alga <Emphasis Type="Italic">Sargassum thunbergii</Emphasis>

Two new monogalactosyl diacylglycerols (MGDGs) along with two known glycolipids were isolated from the moderate polar fraction of the methanolic extract of the brown alga Sargassum thunbergii by using reversed silica flash chromatography. Two new MGDGs were identified as (2S)-1-O-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-β-d-galactopyranosyl-sn-glycerol (1) and (2S)-1-O-(9Z,12Z,15Z-octadecatrienoyl)-2-O-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-3-O-β-d-galactopyranosyl-sn-glycerol (2) by FAB tandem mass spectrometry, NMR techniques, and specific enzyme-catalyzed hydrolysis of the sn-1 fatty acyl linkage. The regiochemical attachment of the acyl chains in the glycerol moiety was established by 2D NMR correlations and confirmed by enzymatic hydrolysis.     

New glyceroglycolipid and ceramide from <Emphasis Type="Italic">Premna microphylla</Emphasis>

Iwo new compounds (1,2) were isolated from the ethanolic extract of the leaves of Premna microphylla, together with five known compounds. The structures of compounds 1 and 2 were elucidated as (2S,3S,4R,11E)-2-[(2R)-2-hydroxytetracosanoylamino]-11-octadecene-1,3,4-triol (1) and 1-O(9Z,12Z, 15Z-octadecatrienoyl)-3-O-[β-d-galactopyranosyl-(1→6)-O-β-d-galactopyranosyl-(1→6)-α-d-galactopyranosyl] glycerol (2) by means of spectroscopic and chemical methods.     

New Sphingolipids with a Previously Unreported 9-Methyl-C<Subscript>20</Subscript>-sphingosine Moiety from a Marine Algous Endophytic Fungus <Emphasis Type="Italic">Aspergillus niger</Emphasis> EN-13

Asperamides A (1) and B (2), a sphingolipid and their corresponding glycosphingolipid possessing a hitherto unreported 9-methyl-C₂₀-sphingosine moiety, were characterized from the culture extract of Aspergillus niger EN-13, an endophytic fungus isolated from marine brown alga Colpomenia sinuosa. The structures were elucidated by spectroscopic and chemical methods as (2S,2′R,3R,3′E,4E,8E)-N-(2′-hydroxy-3′-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (1) and 1-O-β-d-glucopyranosyl-(2S,2′R,3R,3′E,4E,8E)-N-(2′-hydroxy-3′-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (2). In the antifungal assay, asperamide A (1) displayed moderate activity against Candida albicans.     

Attraction of New Zealand Flower Thrips, <Emphasis Type="Italic">Thrips obscuratus</Emphasis>, to <Emphasis Type="Italic">cis</Emphasis>-Jasmone,a Volatile Identified from Japanese Honeysuckle Flowers

This work was undertaken to identify floral compound(s) produced by honeysuckle flowers, Lonicera japonica (Thunberg), that mediate the attraction of New Zealand flower thrips Thrips obscuratus (Crawford). Volatiles were collected during the day and night and analyzed by gas chromatography–mass spectrometry (GC-MS) to determine their emission over these two periods. Nine compounds were identified in the headspace; the main compound was linalool, and the other compounds were germacrene D, E,E-alpha-farnesene, nerolidol, cis-jasmone, cis-3-hexenyl acetate, hexyl acetate, cis-hexenyl tiglate, and indole. There was a quantitative difference between day and night volatiles, with cis-3-hexenyl acetate, hexyl acetate, cis-hexenyl tiglate, and cis-jasmone emitted in higher amounts during the day compared to the night. When the compounds were tested individually in field trapping experiments, only cis-jasmone attracted New Zealand flower thrips in a significant number. In another field trapping experiment, cis-jasmone caught similar numbers of New Zealand flower thrips compared to a floral blend formulated to mimic the ratios of the compounds emitted during the day, while catch with the night-emitted floral blend was not significantly different from the control. Subsequently, two field trapping experiments were conducted to determine the optimal attraction dose for cis-jasmone, a range of 1–100 mg loaded onto a red rubber stopper was tested, and the highest catches were in traps baited with 100 mg loading. A higher range of 100–1000 mg loaded into polyethylene vials was tested, and the highest catch was in traps baited with 500 mg. In another experiment aimed at comparing the attraction efficacy of cis-jasmone with the two other known thrips attractants (ethyl nicotinate and p-anisaldehyde), ethyl nicotinate showed the highest trap catch followed by cis-jasmone. A smaller number of Thrips tabaci (Lindeman) was attracted to traps baited with cis-jasmone. These results suggest that cis-jasmone might act as a kairomone that mediates the attraction of New Zealand flower thrips to the flowers of the Japanese honeysuckle.     

Phytotoxic and Antifungal Compounds from Two <Emphasis Type="Italic">Apiaceae</Emphasis> Species, <Emphasis Type="Italic">Lomatium californicum</Emphasis> and <Emphasis Type="Italic">Ligusticum hultenii</Emphasis>, Rich Sources of Z-ligustilide and Apiol,Respectively

The seeds of two Apiaceae species, Ligusticum hultenii and Lomatium californicum, were investigated. Preliminary bioassays indicated that methylene chloride extracts of seeds of both species contained selective phytotoxic activity against monocots and antifungal activity against Colletotrichum fragariae. Active constituents were isolated by bioassay-guided fractionation, and the structures were elucidated by NMR and GC-MS as apiol and Z-ligustilide, isolated from L. hultenii and L. californicum, respectively. Apiol and Z-ligustilide had I₅₀ values of about 80 and 600 μM, respectively, for inhibition of the growth of Lemna paucicostata. The methylene chloride (CH₂Cl₂) extracts of the seeds and the isolated and purified compounds were tested against the 2-methylisoborneol-producing cyanobacterium (blue-green alga) Oscillatoria perornata, and the green alga Selenastrum capricornutum. The CH₂Cl₂ extracts of both Apiaceae species and apiol were weakly toxic to both species of phytoplankton, while Z-ligustilide was toxic to both with a lowest complete inhibitory concentration (LCIC) of 53 μM. Seeds of L. californicum and L. hultenii were found to be rich sources of Z-ligustilide (97 mg/g of dry seed) and apiol (40 mg/g of dry seed), respectively.     

A new glucoceramide from the watermelon begonia, <Emphasis Type="Italic">Pellionia repens</Emphasis>

A new glucoceramide named pellioniareside (1) was isolated from the aqueous ethanolic extract of whole plants of Pellionia repens, together with lupeol (2), uracil (3), (22E,20S,24R)-5α,8α-epidioxyergosta-6,22-dien-3-β-ol (4), and daucosterol (5). The structure and relative configurations of pellioniareside were identified as (2S,3S,4R,6E,8E)-1-O-β-d-glucopyranosyl-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-octadecanetriol-6,8-diene by analysis of spectral data and by chemical evidence.     

Pecipamide,a New Sphingosine Derivative from the Cultures of <Emphasis Type="Italic">Polyporus picipes</Emphasis> (Basidiomycetes)

A new C₁₈-ceramide congener named pecipamide (1), together with the known ergosta-4,6,8(14),22-tetraen-3-one (2), was isolated from the solid fermentations of the basidiomycetous fungus Polyporus picipes. The structure of the new metabolite was established as (2′R,2S,3R)-N-2′-hydroxyheptadecanoyl-2-amino-octadecane-1,3-diol on the basis of spectroscopic data, including 1D- and 2D- nuclear magnetic resonance spectroscopy (NMR) experiments, as well as by means of mass spectrometric measurements (MS).     

Role of (3<Emphasis Type="Italic">Z</Emphasis>,6<Emphasis Type="Italic">Z</Emphasis>,8<Emphasis Type="Italic">E</Emphasis>)-Dodecatrien-1-ol in Trail Following,Feeding, and Mating Behavior of <Emphasis Type="Italic">Reticulitermes hesperus</Emphasis>

Trail pheromones mediate communication among western subterranean termites, Reticulitermes hesperus Banks. Repetitive passages of ≥28 termites were required to establish a pheromone trail and trails needed to be reinforced because they lasted <48 hr. The minimal threshold concentration for inducing responses from termite workers and secondary reproductives was between 0.01 and 0.1 fg/cm of (3Z,6Z,8E)-dodecatrien-1-ol (henceforth, dodecatrienol). Workers showed optimal trail-following behavior to dodecatrienol at a concentration of 10 fg/cm. Trails with concentrations >10 pg/cm were repellent to workers. Workers did not detect pheromone gradients, responding equally to increasing or decreasing gradients of dodecatrienol, and termite workers were not able to differentiate between different concentrations of dodecatrienol. Termites preferred dodecatrienol trails to 2-phenoxyethanol trails. Antennae played a key role in trail pheromone perception. Dodecatrienol acted as an arrestant for worker termites (10 fg/cm²) and male alates (5 ng/cm²), whereas sternal gland extracts from females attracted male alates. Workers and alates, upon contact with filter paper disks treated with higher doses (10 fg/cm² and 5 ng/cm², respectively) of dodecatrienol, were highly excited (increased antennation and palpation) and repeatedly returned to the treated disks. Dodecatrienol did not act as a phagostimulant when offered on a paper towel disk. Reticulitermes hesperus is highly responsive to dodecatrienol, and it may play an important role in orientation of workers and alates.     

Synthesis and Properties of 1,1-bis{[3-(<Emphasis Type="Italic">N</Emphasis>,<Emphasis Type="Italic">N</Emphasis>-Dimethylamino)propyl]amido}alkane-di-<Emphasis Type="Italic">N</Emphasis>-oxides

A homologous series of new surface-active 1,1-bis{[3-(N,N-dimethylamino)propyl]amido}alkane-di-N-oxides were synthesized in the reaction of an appropriate diethyl 2-alkylmalonate with N,N-dimethylamino-1,3-propanediamine followed by oxidation with aqueous hydrogen peroxide. The adsorption isotherms of their aqueous solutions were measured and evaluated to obtain adsorption parameters: critical micelle concentration (CMC), surface excess concentration (Γ_CMC), equilibrium surface tension at the CMC (γ_CMC), cross-sectional area of the adsorbed surfactant molecule (A _CMC), efficiency of surface adsorption (pC₂₀), standard free energies of adsorption (ΔG°_ads), and micellization (ΔG°_CMC). All investigated di-amidoamines and di-N-oxides were practically non-toxic to selected bacteria and yeasts. These compounds are readily biodegradable in the Closed Bottle Test inoculated with activated sludge. Surface and biological properties showed that this group of N-oxide-type compounds has high surface activity and fulfills requirements for environmental acceptance.

(2<Emphasis Type="Italic">S</Emphasis>,8<Emphasis Type="Italic">Z</Emphasis>)-2-Butyroxy-8-heptadecene: Major Component of the Sex Pheromone of Chrysanthemum Gall Midge, <Emphasis Type="Italic">Rhopalomyia longicauda</Emphasis>

The sex pheromone of the chrysanthemum gall midge, Rhopalomyia longicauda (Diptera: Cecidomyiidae), the most important insect pest in commercial plantations of chrysanthemum, Dendranthema morifolium (Ramat.) Tzvel., in China, was identified, synthesized, and field-tested. Volatile chemicals from virgin females and males were collected on Porapak in China and sent to the United Kingdom for analysis. Coupled gas chromatographic–electroantennographic detection (GC-EAG) analysis of volatile collections from females revealed two compounds that elicited responses from antennae of males. These compounds were not present in collections from males. The major EAG-active compound was identified as 2-butyroxy-8-heptadecene by gas chromatographic (GC) retention indices, mass spectra, in both electron impact and chemical ionization modes, hydrogenation, epoxidation, and derivatization with dimethyldisulfide. The lesser EAG-active compound was identified as the corresponding alcohol. The ratio of butyrate to alcohol in the collections was 1:0.26. Racemic (Z)-8-heptadecen-2-ol and the corresponding butyrate ester were synthesized from (Z)-7-hexadecenyl acetate, and the synthetic compounds found to have identical GC retention indices and mass spectra to those of the natural, female-specific components. Analysis of the volatile collections on an enantioselective cyclodextrin GC column showed the natural pheromone contained (2S,8Z)-2-butyroxy-8-heptadecene. Field tests showed that rubber septa containing racemic (Z)-2-butyroxy-8-heptadecene were attractive to R. longicauda males. The (naturally occurring) S-enantiomer was equally as attractive as the racemate, while the R-enantiomer was not attractive to males, and did not inhibit the activity of the S-enantiomer. The attractiveness of the butyrate was significantly reduced by the presence of even small amounts of the corresponding alcohol.     

Novel ceramides and a new glucoceramide from the roots of <Emphasis Type="Italic">Incarvillea arguta</Emphasis>

Novel ceramides, rel-(3S,4S,5S)-3-[(2R)-2-hydroxycosanoyl-hexacosanoylamino]-4-hydroxy-5-[(4Z)-tetradecane-4-ene]-2,3,4,5-tetrahydrofuran (1a-g), and a new glucoceramide, 1-O-β-d-glucopyranosyl-(2S,3S,4R,8E)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-octodecanetriol-8-ene (2) were isolated from the aqueous ethanolic extract of the roots of Incarvillea arguta, together with eight known compounds: β-sitosterol (3), oleanolic acid (4), ursolic acid (5), piperin (6), maslinic acid (7), β-sitosterol 6′-O-acyl-β-d-glucopyranoside (8), 8-epideoxyloganic acid (9), and plantarenaloside (10). Their structures were elucidated on the basis of spectral data including IR, MS, NMR [¹H NMR, ¹³C NMR (distortionless enhancement by polarization transfer), ¹H−¹H COSY, heteronuclear multiplequantum coherence, and heteronuclear multiple-bond coherence correlations]. The relative configurations were established by nuclear Overhauser effect spectroscopy experiments and by comparison of the NMR spectral data and coupling constants with those already reported in the literature.