Lupeyl Acetate Research Articles

GC-MS/MS and 1H-NMR analysis of endemic Campanula baskilensis Behçet leaf fractions

In this research, 1H-NMR and CG-MS/MS spectrophotometric techniques were used to elucidate the chemical profile of leaf fractions of Campanula baskilensis Behçet. A column chromatography system was used for the fractionation of the crude extract. Fifteen separate fractions were obtained throughout the fractionation procedure. Thirty-nine molecules were identified using both spectrometry techniques. Thirty-one compounds of these molecules were identified, and eight compounds were listed as unknown. For lupeyl acetate, it was determined as 77.80% in Fr6-2, 63.21% in Fr3-3, 43.81% in Fr4-3, and for 1-octadecene, it was determined as 36.23% in Fr3-2 and 32.14% in Fr4-1. Additionally, levels of 34.88% for hexadecanoic acid and 34.05% for borneol were recorded at Fr8. It is also noteworthy that, as an unknown molecule, Fr3-4 is formed at a rate of 97.28%. Molecular structures such as hexadecanoic acid (methyl palmitate), benzoic acid, eicosanoic acid, limonene, borneol, and hentriacontanol were supported by 1H-NMR analysis. Understanding the chemical constituents of C. baskilensis plant will provide opportunities to suggest broader research in the future. The identified molecules can be the subject of isolation and further original models for various in-vitro and in-silico bioassays or effective drug development and application.

Ethnobotanical and Phytochemical Study of Bayur (<i>Pterospermum javanicum</i> Jungh.) on Sasak Tribe around Mount Rinjani National Park, West Lombok as a Conservation Effort

Pterospermum javanicum Jungh. (Bayur) is a species belongs to the Pterospermum genera (Malvaceae). Several species of Pterospermum had been reported for their ethnobotanical usage, but the studies about ethnobotany information of Bayur and its secondary metabolite compounds were still limited which have been published. This study aimed to observe the ethnobotanical usage of Bayur and to examine the phytochemical contents of the acetone extract of Bayur flower from West Lombok. The ethnobotany information of Bayur was obtained through interviews with local people and more information on the ethnobotanical records of P. javanicum (Bayur) was conducted by reviewing the scientific literature. The chemical compounds of Bayur flower were analysed by the GC-MS method. The results revealed that Bayur was used by the Sasak community around Gunung Rinjani National Park West Lombok for various purposes, such as traditional medicines, beverages, rigging, and building material. The phytochemical analysis showed that the acetone extract of Bayur flower from West Lombok contained 38 identified chemical components, representing 93.78% of the total compounds. The major contents of them were Lupeyl acetate (10.68%), p-n-Amylphenol (8.16%), Lauric acid (7.31%), N-(Methyl-d2)- Aniline (5,82%), and Pentanal (5.07%). This report was the first publication about the phytochemical contents of Bayur flower. It is expected that this study gives further information on the potentials of Bayur, especially about its secondary metabolite to support and prove the truth of the cultural concept of society in utilizing Bayur as a medicinal plant.

Phytochemical study on the flower of Alstonia macrophylla Wall. ex G.Don (Apocynaceae) from Sumbawa Island, Indonesia

Alstonia macrophylla Wall. ex G.Don is a native plant to South East Asia, belonging to Alstonia genus. This species has been reported to have numerous natural chemical compound which perfom multiple pharmacological and biological activities. The aim of this study was to investigated the phytochemical properties of the acetone extract of the flower of lstonia macrophylla Wall. ex G.Don. This is very interesting because phytochemical properties of its flower had been never reported yet. Alstonia macrophylla was harvested from the Natural Forest of Punik, Batu Dulang Village, Batulanteh Subdistrict, Sumbawa Regency, West Nusa Tenggara, Indonesia on Mei 2015. Acetone flower extract of A. macrophylla was analyzed with a GC-MS method to determine the chemical components. Result of GC–MS chromatogram revealed that there were 30 identified components in this extract. The major compounds were Cycloartenol acetate (17.11 %); 5H-1-Pyrindine (12.44 %); Lupeyl acetate (10.12%); Oleic acid (6.08 %); Benzenesulfonic acid, 4-hydroxy- (4.25 %); p-n-Amylphenol (4.23 %); and 4-Methylindole (4.22 %). Here, We reported the first study of phytochemical properties of A. macrophylla. This study help to understand further detail the potential of bioactive compound of A. macrophylla.

Constituintes químicos de Vernonia scorpioides (Lam) Pers. (Asteraceae)

CHEMICAL CONSTITUENTS OF Vernonia scorpioides (Lam) Pers. (Asteraceae). The chemical investigation of hexane and ethanol extracts from the aerial parts of Vernonia scorpioides resulted in the isolation and characterization of a new polyacetylene lactone, rel-4-dihydro-4β-hydroxy-5a-octa-2,4,6-triynyl-furan-2-(5H)-one, along with the new ethyl 3,4-dihydroxy-6,8,10-triynyldodecanoate, and seven known compounds: taraxasteryl acetate, lupeyl acetate, lupeol, lupenone, β-sitosterol, stigmasterol and luteolin. The structure of all compounds was determined by spectrometric techniques (HR-ESI-MS, 1H and 13C NMR and IV) and comparison with published spectral data.

Triterpenes from the flowers of Gochnatia polymorpha subsp. floccosa

Phytochemical study of the flowers of Gochnatia polymorpha subsp. floccosa, Asteraceae, yielded eleven known triterpenes identified as lupeol, lupeyl acetate, lupeyl palmitate, taraxasterol, taraxasteryl acetate, pseudotaraxasterol, pseudotaraxasterol acetate, α-amyrin, α-amyryl palmitate, β-amyrin and β-amyryl palmitate, along with sitosterol, stigmasterol, palmitic and stearic acids. These compounds are been reported for the first time in the species. The compounds were identified by analysis of NMR spectra (1H, 13C and DEPT), GC-MS and comparison with literature data. Previous work have reported the isolation of triterpenes, diterpenes, sesquiterpenes, flavonoids, coumarins and phenolic compounds from aerial parts and roots from G. polymorpha.

Occurrence and Sources of Triterpenoid Methyl Ethers and Acetates in Sediments of the Cross-River System, Southeast Nigeria

Pentacyclic triterpenol methyl ethers (PTMEs), germanicol methyl ether (miliacin), 3-methoxyfern-9(11)-ene (arundoin), β-amyrin methyl ether (iso-sawamilletin), and 3-methoxytaraxer-14-ene (sawamilletin or crusgallin) were characterized in surface sediments of the Cross-River system using gas chromatography-mass spectrometry (GC-MS). Triterpenol esters (mainly α- and β-amyrinyl acetates and hexanoates, and lupeyl acetate and hexanoate) were also found. These distinct compounds are useful for assessing diagenesis that can occur during river transport of organic detritus. Poaceae, mainly Gramineae and Elaeis guineensis higher plant species, are proposed as primary sources for the PTMEs and esters in the sediments. PTMEs are biomarkers of specific higher plant subspecies, while the triterpenol esters are indicators of early diagenetic alteration of higher plant detritus.

Constituintes químicos de Vernonia chalybaea mart.

The chemical investigation of the hexane and ethanol extracts from aerial parts of Vernonia chalybaea conducted to the isolation and characterization of a new aliphatic tetrahydroxyl ether, along with a series of known compounds such as 4 α,10 α-epoxyaromadendrane, friedelin, taraxasteryl acetate, pseudotaraxasteryl acetate, lupeyl acetate, lupeol, α-amiryn, β-amiryn, β-sitosterol, stigmasterol, 2,3-dimethyl-1,2,3-tri-hydroxybuthanol, angophorol, angophorol-7-O-glucoside, angophorol-7-O-rutinoside, 3,7-dimethoxy-5,3',4'-trihydroxyflavone and acacetin. The structures of all compounds were determined by spectroscopic analysis and comparison with published spectral data.

New Lupane Triterpenoids from Solidago canadensis that Inhibit the Lyase Activity of DNA Polymerase β.

Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase beta, resulted in the isolation of the four new lupane triterpenoids 1-4 and the seven known compounds lupeol, lupeyl acetate, ursolic acid, cycloartenol, cycloartenyl palmitate, alpha-amyrin acetate, and stigmasterol. The structures of the new compounds were established as 3beta-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene (1), 3beta-(3-ketohexadecanoyloxy)-lup-20(29)-ene (2), 3beta-(3R-acetoxyhexadecanoyloxy)-29-nor-lupan-20-one (3), and 3beta-(3-hetohexadecanoyloxy)-29-nor-lupan-20-one (4), respectively, on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical modification studies. All 11 compounds were inhibitory to the lyase activity of DNA polymerase beta.

New lupane triterpenoids from Solidago canadensis that inhibit the lyase activity of DNA polymerase β

Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase β, resulted in the isolation of the four new lupane triterpenoids 1–4 and the seven known compounds lupeol, lupeyl acetate, ursolic acid, cycloartenol, cycloartenyl palmitate, α-amyrin acetate, and stigmasterol. The structures of the new compounds were established as 3β-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene (1), 3β-(3-ketohexadecanoyloxy)-lup-20(29)-ene (2), 3β-(3R-acetoxyhexadecanoyloxy)-29-nor-lupan-20-one (3), and 3β-(3-hetohexadecanoyloxy)-29-nor-lupan-20-one (4), respectively, on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical modification studies. All 11 compounds were inhibitory to the lyase activity of DNA polymerase β.

New Cytotoxic Terpenoids from the Wood of Vepris punctata from the Madagascar Rainforest

Continuation of the chemical examination of the cytotoxic constituents of the wood of Vepris punctata resulted in the isolation of the two new terpenoids 1 and 2 and eight known compounds, glechomanolide (3), isogermafurenolide, (E,E)-germacra-1(10),4,7(11)-triene, alpha-amyrin, lupeol, lupeyl acetate, taraxerol, and 3-epi-taraxerol, in addition to the alkaloids reported reported previously. The structures of the two new compounds were established on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical modifications. All the isolated compounds were tested against the A2780 human ovarian cancer cell line; the four sequiterpenoids showed moderate cytotoxic activity, while the six triterpenoids were inactive.

Sesquiterpene lactones and other chemical constituents of Mikania hoehnei R.

Phytochemical study of Mikania hoehnei yielded lupeyl acetate, stigmasterol, b-sitosterol, campesterol, b-sitosteryl glucopyranoside, stigmasteryl glucopyranoside, benzil 2,6-dimethoxybenzoate, luteolin, kaempferol and two sesquiterpene lactones: dehydrocostuslactone and 8b-hydroxyzaluzanin D. IR, ¹H and 13C NMR and MS spectroscopic analyses and comparisons with previously reported data were used for the identification of these compounds.

New cytotoxic lupane triterpenoids from the twigs of Coussarea paniculata.

Bioassay-guided fractionation of a CH(2)Cl(2)-MeOH extract of the twigs of Coussarea paniculata using a yeast-based assay for potential DNA-damaging agents resulted in the isolation of three new lupane triterpenoids, 1-3, in addition to eight known triterpenoids, lupeol (4), lupeyl acetate (5), betulin (6), betulinic acid (7), 3-epi-betulinic acid (8), 3-epi-betulinaldehyde (9), oleanolic acid (10), and ursolic acid (11). The structures of the new compounds were established as lup-20(29)-en-3beta,25-diol (1), lup-20(29)-en-11alpha-ol-25,3beta-lactone (2), and 3-deoxybetulonic acid (3), on the basis of extensive 1D and 2D NMR spectroscopic data interpretation and chemical conversion.

Two new triterpene esters from the twigs of Brachylaena ramiflora from the Madagascar rainforest.

Bioassay-guided fractionation of a CH(2)Cl(2)/MeOH extract of the small twigs of Brachylaena ramiflora var. ramiflora resulted in the isolation of the two new triterpene esters 1 and 2 and five known triterpenoids, alpha-amyrin palmitate (3), beta-amyrin palmitate (4), beta-amyrin acetate (5), lupeyl acetate (6), and lupeol (7). The structures of the two new compounds were established as kairatenyl palmitate (1) and hopenyl palmitate (2) on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical conversions. All the isolated compounds showed weak cytotoxicity against the A2780 human ovarian cancer cell line.

A dithiophene from Aphyllocladus denticulatus

A new dithiophene, aphyllocladine, lupeonone, lupeol and apigenin were isolated and identified from Aphyllocladus denticulatus. Lupeyl acetate and lupeol were isolated from Urmenetea atacamensis.

Epicuticular wax constituents of North American and European Euphorbia esula biotypes

The epicuticular leaf wax of four North American and one Austrian Euphorbia esula biotypes was examined as a potential source of chemotaxonomic information relative to intraspecies classification. Analysis (GC and GC/MS) shows general similarity of wax constituent character among all biotypes but differences in specific component yields between the North American and Austrian biotypes. Distinctive variation in occurrence of five triterpenes (α- and β-amyrin, δ-amyrenone, 24-methylenecycloartenol and lupeyl acetate) was observed between the North American and Austrian biotypes.

Eudesmanolides and ent-pimaranes from Liatris laevigata

Liatris laevigata gave five new closely related 1β-hydroxy-8β-tigloxyeudesman-6α,12-olides as well as lupeol, lupeyl acetate and the new diterpenes ent-8,15 R-epoxy-3-oxopimara-12α,16-diol, ent-8,15 R-epoxypimara-3β,12α,16-triol and its 15 S epimer.

Caryophyllene derivatives and a heliangolide from Lychnophora species

The investigation of three Lychnophora species afforded three new caryophyllenic acids and a new heliangolide closely related to 15-desoxygoyazensiolide. All three species contain lupeol, lupeyl acetate and eremanthine. The chemotaxonomic situation is discussed briefly.

β–Amyrin Acetate and Lupeyl Acetate from Marsdenia erecta

β–Amyrin Acetate and Lupeyl Acetate from Marsdenia erecta

The triterpenes of ouricuri wax

AbstractOuricuri was contains lupeyl acetate (3.9%), taraxerone (1.3%), lupenone (1.2%), simiarenol (0.09%), and taraxeryl acetate (0.03%). The triterpenes can be readily isolated from the wax by hexane extraction. Gas liquid chromatographic analysis shows that lupeyl acetate is the principal single component of the wax.

The occurrence of 11,12-dehydroursolic lactone acetate in Eucalyptus waxes

��� 11,12-Dehydroursolic lactone acetate, previously reported as a reduction product of 11-ketoursolic acid, has been isolated from several Eucalyptus waxes. The waxes from Acacia iteaphylla F. Muell. and Acacia suaveolens Willd. contain lupeyl acetate, and wax from Echeveria secunda Booth ex Lindl. contains β-amyrenyl acetate.