A new cyclohexadecane derivative from Trixis vauthieri DC (Asteraceae)

The dichloromethane-methanol extract from the fresh leaves of Trixis vauthieri DC (Asteraceae) afforded trixol, a new cyclohexadecane derivative. The structural elucidation of this new compound, with a novel skeleton, was based on NMR studies of the natural product nd its derivatives.     

A new ent-clerodane diterpenoid from Crassocephalum bauchiense Huch. (Asteraceae)

A phytochemical investigation of the whole plant of Crassocephalum bauchiense Huch. resulted in the isolation of a new clerodane diterpenoid, ent-2β,18,19-trihydroxycleroda-3,13-dien-16,15-olide (1), together with two known flavonoids 3′,5-dihydroxy-4′,5′,6,7,8-pentamethoxyflavone (2) and 4′,5-dihydroxy-3′,5′,6,7,8-pentamethoxyflavone (3). The compounds were tested against the chloroquine-sensitive 3D7 strain of Plasmodium falciparum. Compound 2 showed weak activity (IC₅₀ = 10.1 g/mL) whilst compounds 1 and 3 were inactive. The structures of the compounds were elucidated by using detailed spectral analyses, especially ¹H and ¹³C NMR, ¹H–¹H COSY, NOESY, HMBC and HR-ESI-MS.     

Sesquiterpene lactones from Crepis cameroonica (Asteraceae)

In addition to one known compound, 3beta,8alpha-dihydroxyguaian-4(15),10(14),11(13)-trien-6,12 olide (8-desacylcynaropicrin) (3), two new sesquiterpene lactones have been isolated from the aerial parts of Crepis cameroonica. By means of spectroscopic analysis, the structures and relative configurations of the new compounds were established as 3beta,9beta-dihydroxyguaian-4(15),10(14),11(13)-trien-6,12 olide (1) and 8alpha-hydroxy-4alpha(13),11beta(15)-tetrahydrozaluzanin C (2). The in vitro antimicrobial spectrum of pure compounds and crude extracts are also reported.     

Bioactive compounds from Iostephane heterophylla (Asteraceae)

The novel bisabolene sesquiterpenes 3-6, were isolated from Iostephane heterophylla, using bioguided fractionation. The new compounds were determined to be (12R/12S)-12,13-epoxy-xanthorrhizols (3,4) and (12R/12S)-12,13-dihydro-12,13-dihydroxy-xanthorrizols (5,6) and their structures were characterized by analysis of spectroscopic data and by chemical correlation from xanthorrhizol (2). The stereochemistry at C-12 of 5 was deduced using the modified Mosher experiment. Some of the isolated compounds elicited activity against gram positive and gram negative bacteria, levadura and dermatophytes.     

Chemical composition of the essential oil from Pulicaria vulgaris var. graeca (Sch.-Bip.) Fiori (Asteraceae) growing wild in Sicily and its antimicrobial activity

In this study the chemical composition of the essential oil from aerial parts of Pulicaria vulgaris var. graeca (Sch.-Bip.) Fiori collected in Sicily was evaluated by GC and GC–MS. The main components of P. vulgaris var. graeca oil were hexadecanoic acid (21.7%), β-caryophyllene (14.3%) and geranyl propionate (8.2%). The comparison with other studied oils of genus Pulicaria is discussed. Antibacterial activity against several bacteria, including some ones infesting historical art craft, was also determined.     

Hautriwaic Acid from Pulicaria salviifolia

A diterpene acid was isolated from the aerial part of Pulicaria salviifolia. Spectral data and chemical transformations identify it as hautriwaic acid.     

An unusual sesquiterpenoid from Hypochaeris achyrophorus (Asteraceae)

The novel sesquiterpenoid 8alpha-hydroxyhypoglabric acid (1) was isolated from a methanolic extract of whole plants of Hypochaeris achyrophorus L. The compound was isolated by silica gel column chromatography (CC), repeated Sephadex LH-20 CC, and semi-preparative RP-HPLC. Structure elucidation was accomplished by high resolution mass spectrometry and by 1D- and 2D-NMR spectroscopy. The chemosystematic significance of the new compound is discussed in the context of sesquiterpenoids from other members of the Hypochaeridinae and in the light of recent molecular data on the phylogeny of this group.     

A new acylated flavonol from the aerial parts of Asteriscus maritimus (L.) Less (Asteraceae)

Phytochemical investigation of the flowering aerial parts of Asteriscus maritimus (L.) Less (Asteraceae) led to the isolation of a new compound: patuletin 7-O-β-D-[(2″′S) 6″(3″′-hydroxy-2″′-methyl-propanoyl)] glucopyranoside, together with five known metabolites; β-sitosterol 2, chlorogenic acid 3, P-hydroxy -methylbenzoate 4, luteolin 5 and protocatechuic acid 6. The structures of the isolated compounds were determined by comprehensive analyses of its 1D and 2D NMR, HRMS and compared with previously known analogues. The ethanolic extract of the flowering aerial parts of A. maritimus was found to be safe (LD₅₀ = 4.6 mg/kg) and possess significant antioxidant and anti-inflammatory activities and this was in accordance with its high phenolic content (107.36 ± 0.051 mg GAE/g extract).     

A bis-bithiophene from Tridax procumbens L. (Asteraceae)

The ethyl acetate soluble part of hexane extract of Tridax procumbens yielded a new bis-bithiophene named tridbisbithiophene along with four known terpenoids: taraxasteryl acetate, beta-amyrenone, lupeol and oleanolic acid, which have never been reported so far from Tridax procumbens. The structures of all the isolated constituents were elucidated with the aid of 1D-NMR spectroscopy whereas, the structure of new constituent tridbisbithiophene was confirmed via COSY and HMBC interactions.     

Chemical composition of the essential oil from Carramboa littlei (Asteraceae)

The essential oil from the leaves of Carramboa littlei Aristeg. was isolated by hydrodistillation yielding 0.09%, w/v. The chemical composition was determined by GC-FID and GC-MS. Sixteen components were identified by comparison of their mass spectra with Wiley and NIST library data. The major constituents of the oil were germacrene-D (50.0%), bicyclogermacrene (4.8%) and ent-kaur-16-en-19-al (21.8%).     

Glebionis coronaria (L.) Cass. ex Spach (Asteraceae)- a new fabric dye with potential antibacterial properties

The paper elucidates first ever report on Glebionis coronaria (L.) Cass. ex Spach as a new dyeing agent with high antibacterial activity. Glebionis coronaria (L.) Cass. ex Spach which is also known as Garland/Crown Daisy belonging to the flowering plant family Asteraceae has been identified as a new precursor/candidate to produce highly efficient natural textile dye and a potential antibacterial agent. Natural dye from garland daisy was extracted from the dried petals using DCM and MeOH solvent system. Change in mordants yielded 12 different shades of colours. Spectroscopic analysis of these extracts revealed the presence of carotenoids and flavonoids pigments and hence giving varied shades of yellow, greenish yellow colours (Code No. is assigned to each colour). Alum and stannous chloride have been found to give bright colours while ferrous sulphate gave dark shades of colour. Antibacterial activity of the extracts was studied against non-pathogenic bacteria's, Staphylococcus aureus (Gram-positive bacteria) and for the first time for Aeromonas sp. (Gram-negative bacteria). Two different concentrations of 10 ​mg/ml DCM and methanol extracts using methanol as solvent were tested. Both DCM and methanol extracts have shown inhibition in Aeromonas sp. while only DCM extract was inhibiting S. aureus. The flower extracts has not been evaluated till date for its dyeing properties with different mordants along with their bactericidal activity. Therefore, our present work was to extract natural dye from the flowers of Glebionis Coronaria (L.) Cass. ex Spach. and to do a detailed study.     

Artalbic acid, a sesquiterpene with an unusual skeleton from Artemisia alba (Asteraceae) from Sicily

From the aerial parts of Artemisia alba (Asteraceae) artalbic acid (1), a sesquiterpene with an unusual skeleton, was isolated. Its structure was elucidated on the basis of extensive proton, ¹³C and two-dimensional NMR experiments, as well as by transformation in its methyl ester derivative.     

Flavonoid pulicarpin from Pulicaria salviifolia and its hypolipidemic activity

The new compound 3,6-dihydroxy-3,4,5,7-tetramethoxyflavone has been isolated from the epigeal part ofPulcaria salviifolia Bunge and has been called pulicarin. Its structure has been established on the basis of physicochemical and spectral parameters (UV, IR, and mass spectra and PMR). Its hypolipidemic activity has been studied.Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, Nos. 3, 4, pp. 328–330, May–August, 1992.     

N-cyanomethylnorboldine: a new aporphine isolated from Alseodaphne perakensis (Lauraceae)

A phytochemical study of the bark of Alseodaphne perakensis has yielded three aporphine alkaloids: the new compound N-cyanomethylnorboldine (1), and the two known alkaloids N-methyllaurotetanine (2) and norboldine (3). The isolation was achieved by chromatographic techniques and the structural elucidation was performed via spectral methods, notably 1D- and 2D-NMR, UV, IR, and HRFABMS. The vasorelaxation activity of compound 1 has been studied.     

Leptocarposide: a new triterpenoid glycoside from Ludwigia leptocarpa (Onagraceae)

A new triterpenoid bidesmoside (leptocarposide) possessing an acyl group in their glycosidic moiety (1), together with the known luteolin‐8‐C‐glucoside (2) and 1‐O‐β‐d ‐glucopyranosyl‐(2S,3R,8E)‐2‐[(2′R)‐2‐hydroxypalmitoylamino]‐8‐octadecen‐1,3‐diol (3) was isolated from the n‐butanol‐soluble fraction of whole plant of Ludwigia leptocarpa (Nutt) Hara (Onagraceae). Structure of compound 1 has been assigned on the basis of spectroscopic data (¹H and ¹³C NMR, ¹H‐¹H COSY, HSQC, HMBC, and ROESY), mass spectrometry, and by comparison with the literature. This compound was further screened for its potential antioxidant properties by using the radical scavenging assay model 2,2‐diphenyl‐1‐picrylhydrazyl and reveals non‐potent antioxidant activities, while compound 2 shows SC₅₀ of 0,038 mM. Copyright © 2013 John Wiley & Sons, Ltd.     

Terpenoids and related compounds from plants of the family Compositae (Asteraceae)

This review will summarize the authors' studies on the structures of terpenoids and related compounds from plants of the family Compositae (Asteraceae). Eighty three new compounds have been obtained and characterized from seven species of the plants, namely, Erigeron annuus (L.) Pers., Erigeron philadelphicus L., Erigeron sumatrensis Retz, Ligularia dentata Hara, Ligularia stenocephala Matsum. et Koidz., Petasites japonicus Maxim. and Tussilago farfara L.     

一个新的藏药臭蚤草二萜苷

从藏药臭蚤草的95%甲醇提取物中分离得到了2个二萜苷类化合物,采用IR,MS,1H NMR,13C NMR,ESI及HR-ESI等方法鉴定其结构分别为2-0-(2-0-Isovaler-β-D-glucopyranosyl)atraetyligenin(1)和2-O-[2-O-Isovaleryl-3-β-D-apio...     

A Benzofuranoid and Two Clerodane Diterpenoids from Pulicaria wightiana

Methyl 5‐formyl‐1‐benzofuran‐6‐carboxylate ( 1 ) and the two clerodane diterpenes, methyl 6‐oxocleroda‐3,13‐dien‐15,16‐olid‐18‐oate ( 2 ) and 2β‐(2‐methylbutanoyl)cleroda‐3,13‐dien‐15,16‐olid‐18‐oic acid ( 3 ), together with 15 known compounds, were isolated from the aerial parts of Pulicaria wightiana. The structures of the new compounds 1, 2 , and 3 were established by spectroscopic (mainly 1D‐ and 2D‐NMR) methods.