Vestolide,a guaianolide from vicoa vestita

A new sesquiterpene lactone, vestolide, of the guaiane series was isolated from the aerial parts of Vicoa vestita. Its structure was established on the basis of chemical and spectral evidence.     

A guaianolide and other constituents from Lychnophora species

A new guaianolide, 11 β,13-dihydroeremanthine, together with a caryophyllene derivative and pentacyclic triterpenes, has been isolated from Lychnophora species.     

A guaianolide alloside and other constituents from Picris kamtschatica

From Picris kamtschatica two new guaianolide glycosides, including a beta-allopyranosyl analogue of ixerin F, were isolated, in addition to ten known sesquiterpene lactones and six phenolic compounds. This is the first time a sesquiterpene lactone alloside has been described from plants. The compounds were characterized based on mass, 1D and 2D NMR spectral data.     

3-oxa-guaianolides from Achillea millefolium

Aerial parts of Achillea millefolium (Mongolian origin yielded besides desacetylmatricarin two sesquiterpene lactones of a new 3-oxa-guaianolide type, 8-acetyl egelolide and 8- angeloyl egelolide.     

Terpenoids from Achillea distans Waldst. & Kit. ex Willed

The flower heads of Achillea distans afforded nine new sesquiterpene lactones (one glaucolide, six guaianolides and two dimeric lactones) in addition to 18 known terpenoids. The structures and stereochemistry of the new compounds were elucidated by spectroscopic methods. The stereochemistry of 11,13-dihydroezomontanin was revised.     

A guaianolide from Magnolia grandiflora

The leaves of Magnolia grandiflora afforded in addition to costunolide diepoxide and parthenolide a guaianolide named magnograndiolide.     

Achillea ligustica: composition and antimicrobial activity of essential oils from the leaves, flowers and some pure constituents

The composition of the essential oils obtained from the leaves and the flowers of Achillea ligustica (Asteraceae) growing in Sicily has been studied. The main constituents of the leaves were 4-terpineol (19.3%), carvone (8.9%), γ-terpinene (7.2%) and β-phellandrene (6.8%). 4-terpineol (12.0%), carvone (10.0%), and β-phellandrene (5.4%), along with linalool (20.4%) and cedrol (4.3%) were detected in the flower’s oil. Furthermore, the antimicrobial activity of the essential oils and of some of the main constituents were assayed on bacteria and fungi. In memory of Prof. Ivano Morelli (1940–2005)     

A guaianolide from Guevaria sodiroi

A new guaianolide has been isolated from Guevaria sodiroi. It has been assigned the trivial name guevariolide and its structure elucidated.     

Structure and absolute stereochemistry of vanillosmin,a guaianolide from Vanillosmopsis erythropappa

The structure and absolute stereochemistry of vanillosmin were established by chemical and spectral evidence and by comparison with O-acetyl-isophoto-α-santonic lactone and tetrahydroartabsin “C”.     

A Eudesmanolide and a guaianolide from Cyathocline purpurea

Two new sesquiterpene lactones, the eudesmanolide, isoivangustin, and the guaianolide, 6α-hydroxy-4(14),10(15)-guaianadien-8α,12-olide, have been isolated from Cyathocline purpurea.     

A new ecdysteroid and other constituents from two Dioscorea species

Phytochemical investigation of the rhizome of Dioscorea dumetorum has led to the isolation by several chromatographic steps on normal and reversed phase silica gel of a new ecdysteroid, (20R)-5β,11α,20-trihydroxyecdysone (1), and two known ecdysteroids, ajugasterone C (2) and herkesterone (3). Their structures were determined by spectroscopic methods including 1D- and 2D-NMR (COSY, TOCSY, HSQC and HMBC). This is the first report on the occurrence of phytoecdysteroids in the Dioscoreaceae family. These compounds were devoid of antifungal activity against three Candida species (Candida albicans, Candida glabrata and Candida tropicalis, MIC > 200 μg/ml).     

Achillinin A,a Cytotoxic Guaianolide from the Flower of Yarrow,Achillea millefolium

Achillinin A (2β,3β-epoxy-1α,4β,10α-trihydroxyguai-11(13)-en-12,6α-olide, 1), a new guaianolide isolated from the flower of Achillea millefolium, exhibited potential antiproliferative activity to A549, RERF-LC-kj and QG-90 cells with 50% inhibitory concentration (IC₅₀) values of 5.8, 10 and 0.31 μM, respectively.     

In vitro estrogenic activity of Achillea millefolium L.

Isolation and biological characterization of pure compounds was used to identify and characterize estrogenic activity and estrogen receptors (ER) preference in chemical components of Achillea millefolium. This medicinal plant is used in folk medicine as an emmenagogue. In vitro assay, based on recombinant MCF-7 cells, showed estrogenic activity in a crude extract of the aerial parts of A. millefolium. After fractionation of the crude extract with increasing polar solvents, estrogenic activity was found in the methanol/water fraction. Nine compounds were isolated and characterized by HR-MS spectra and 1D- and 2D-NMR techniques. In particular, dihydrodehydrodiconiferyl alcohol 9-O-beta-D-glucopyranoside - a glycosyl-neolignan - was isolated for the first time from the genus Achillea in addition to six flavone derivatives, apigenin, apigenin-7-O-beta-D-glucopyranoside, luteolin, luteolin-7-O-beta-D-glucopyranoside, luteolin-4'-O-beta-D-glucopyranoside, rutin, and two caffeic acid derivatives, 3,5-dicaffeoylquinic acid and chlorogenic acid. Apigenin and luteolin, the most important estrogenic compounds among those tested, were studied for their ability to activate alpha or beta estrogen receptors (ERalpha, ERbeta) using transiently transfected cells. Our results suggest that isolation and biological characterization of estrogenic compounds in traditionally used medicinal plants could be a first step in better assessing further (e.g. in vivo) tests of nutraceutical and pharmacological strategies based on phytoestrogens.     

Three germacranolides and other constituents from Eremanthus species

The re-investigation of Eremanthus glomerulatus afforded three new germacranolides and a guaianolide, while from E. mollis two known furanoheliangolides and a new phenylpropanol derivative were isolated. The germacranolides most probably are precursors of the widespread glaucolides. The structures were elucidated by spectroscopic methods. The chemotaxonomic situation is discussed briefly.     

Sesquiterpene lactones and other constituents from Schistostephium species

From four Schistostephium species, in addition to known compounds, 43 new ones were isolated, three isocomene, two bisabolene, two eudesmane, two allo-himachalene and two nerolidol derivatives, two sesquiterpenes with a new carbon skeleton derived from isocomene, nine eudesmanolides, 20 6,12- and 8,12-germacranolides respectively, and a prostaglandin-like acid. The structures were elucidated by spectroscopic methods, especially high field ¹H NMR and some chemical transformations. The stereochemistry of some 8,12-germacranolides was established by partial synthesis which required revision of the previous assignments of the configuration of inunolide, its 4,5- and 1,10-epoxide, vernudifloride, simsiolide, 6-hydroxy-1,10-epoxyinunolide and perhaps also of tanachin. The chemotaxonomic situation is discussed briefly.     

Sesquiterpene lactones and other constituents from Stevia jorullensis

A chemical study of the aerial parts of Stevia jorullensis was carried out as a contribution to the knowledge of the chemistry of the genus Stevia. In this investigation the sesquiterpene lactones 11β,13-dihydrocostunolide (1), 11,13-dihydroreynosin (4), and 1β-hydroxycolartin (5) were isolated for the first time in the genus. Additionally, chlorogenic acid (8), the steroidal compounds β-sitosterol (2), stigmasterol (3), β-sitosteryl glucopyranoside (6), and stigmasteryl glucopyranoside (7) were also isolated. This is the third report of the presence of a 11,13-dihydrogermacranolide and the second of 11,13-dihydroeudesmanolides in the genus Stevia.     

Cytotoxic constituents of Achillea clavennae from Montenegro

Examination of the aerial parts of Achillea clavennae afforded eight guaianolides (1-8), three bisabolenes (9-11), four flavonols (12-15), sesamin (lignan) and isofraxidin (coumarin). The structures of the new compounds (2, 4, 5, 7 and 10) were determined by spectroscopic methods. The antiproliferative action of 2, 8, 9 and 12 were tested to HeLa, K562 and Fem-X human cancer cell lines. Guaianolides 2 (9alpha-acetoxyartecanin) and 8 (apressin) showed significant cytotoxic effects to all tested lines and inducumenone (9) exhibited a moderate activity. The most active was flavonol centaureidin (12), already known as cytotoxic compound.