Cardiobutanolide,a styryllactone from Goniothalamus cardiopetalus

A styryllactone namely cardiobutanolide was isolated from the stem bark of Goniothalamus cardiopetalus together with four known styryllactones goniothalamin, goniodiol, goniofufurone, goniofupyrone and known acetogenins squamocin and an epimeric mixture of goniodonin and 34-epi-goniodonin. The structure of the new compound was elucidated on the basis of 1D and 2D NMR experiments and mass spectroscopic techniques.     

Alkaloids and styryllactones from the leaves of Goniothalamus tamirensis

Three new compounds, goniotamirine (1), goniotamiric acid (2), and 3,5-demethoxypiperolide (3) were isolated from the leaves of Goniothalamus tamirensis (Annonaceae), together with sixteen known compounds, (?)-N-nornuciferine (4), (?)-norisocorydine (5), (?)-isocorydine (6), (?)-3-hydroxynornuceferine (7), (?)-O-methylisopiline (8), (?)-anonaine (9), (?)-roemerine (10), (?)-roemeroline (11), (?)-boldine (12), glaunine (13), liriodenine (14), 9-deoxygoniopypyrone (15), 8-epi-9-deoxygoniopypyrone (16), 8-epi-9-deoxygoniopypyrone acetate (17), goniodiol (18) and goniothalamin (19). The structures were established from spectral analysis, including mass spectrometry and 2D-NMR. The absolute configuration of 1 was determined from analysis of its MTPA amide derivatives. The cytotoxicity of all isolates was evaluated against KB cells. Only compound 4 (N-nornuciferine) showed a moderate activity with an IC₅₀ value of 12 μg/mL.     

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).     

Bioactive oleanolic acid saponins and other constituents from the roots of Viguiera decurrens

The bisdesmoside oleanolic acid saponin, 3-0-(methyl-beta-D-glucuronopyranosiduronoate)-28-0-beta-D-glucopyranosyl-oleanolate along with nine known compounds (two diterpenic acids, one chromene, three triterpenes, one steroidal glycoside, and two monodesmoside oleanolic acid saponins), were obtained from Viguiera decurrens roots. The chemical structure of the bisdesmoside oleanolic saponin was determined by chemical and NMR spectral evidence. A mixture of monodesmoside saponins displayed cytotoxic activity against P388 and COLON cell lines (ED50= 2.3 and 3.6 microg/ml, respectively). Two of the known compounds showed insecticidal activity against the Mexican bean beetle larvae (Epilachna varivestis).     

A new triterpenoid and other constituents from Lepidogrammitis drymoglossoides

Phytochemical investigation of a Chinese fern Lepidogrammitis drymoglossoides led to the isolation of five compounds, including one triterpenoid, two lignans and two glycosides. Their structures were determined to be filic-3-ene-28-oic acid (1), (−)-syringaresinol-4-O-beta-d-glucopyranoside (2), lyoniresinol (3), 4-O-beta-d-glucopyranosyl caffeic acid (4) and n-butyl-O-beta-d-fructopyranoside (5) on the basis of mass and NMR spectra and chemical and physical properties. Filic-3-ene-28-oic acid (1) is a new triterpenoid, while compounds 2–5 were isolated from the genus Lepidogrammitis for the first time. Chemotaxonomic significance of this investigation is summarized.     

Antiplasmodial activity of naphthoquinones and one anthraquinone from Stereospermum kunthianum

Six new partheniol metabolites were isolated from the biotransformation reaction with Mucor circinelloides ATCC 15242. These metabolites are: humula-1(10), 4, 7-trien-6alpha-ol 2, maali-3-en-8alpha-ol 3, aromadendrane-4alpha, 8alpha, 10alpha-triol 4, maaliane-4alpha, 8alpha, 9alpha-triol 5, maaliane-5alpha, 8alpha, 9alpha-triol 6, 5(9), 6-tricyclohumulane-4alpha, 8alpha, 10alpha-triol 7. The structural assignments of these metabolites were made possible by different spectroscopic means.     

Diarylheptanoids,flavonoids and other constituents from two neotropical Renealmia species (Zingiberaceae)

Phytochemical investigations of the neotropical ginger species Renealmia alpinia and Renealmia cernua led to the isolation of two hitherto unknown diarylheptanoids, named renealpin (1) and renecernin (2). Furthermore, five known diarylheptanoids (3–7), one chalcone (9), two flavonoids (10, 11) and [2]-gingerol (8) were isolated. The organ specific accumulation patterns and chemosystematic significance of these compounds are discussed.     

Flavonoids,megastigmanes and other constituents from Ardisia incarnata

Phytochemical investigation of the leaves and twigs of Ardisia incarnata Pit. (syn. Ardisia hanceana Mez, Primulaceae) led to the isolation of one bicyclic monoterpene (1), five phenolic compounds (2–5, 8), two megastigmanes (6–7) and one glyceroglycolipid (9). Their structures were established based on analysis of their spectroscopic data and comparison with literature. The compounds 1 and 6–9, isolated for the first time from Ardisia genus, may constitute chemomarkers of A. incarnata within Primulaceae family. Moreover, the flavonoid fingerprint may also be of chemotaxonomic significance.     

Horsfieldin,a lignan and other constituents from Horsfieldia iryaghedhi

A new lignan, horsfieldin [2-(3-hydroxy-4-methoxyphenyl)-6-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo(3,3,0)octane], d-asarinin, (?)-dihydrocubebin, dodecanoylphloroglucinol, myristic acid, trimyristin and sitosterol have been isolated and characterized from the hot methanol extract of Horsfieldia iryaghedhi seeds. The absolute configuration of the lignans and the chemotaxonomic significance of their occurrence is discussed.     

Heliangolides and other constituents from Bejaranoa semistriata

The investigation of Bejaranoa semistriata, a new genus in the tribe Eupatorieae, afforded in addition to known compounds a new furanoheliangolide, two epimeric 1-keto-heliangolides, two germacranolides, two nerolidol derivatives and a geranylnerol derivative. The structures were elucidated by spectroscopic methods and a few chemical transformations.     

Volatile constituents from cauliflower and other crucifers

Vapour emanating from intact turnip and radish plants contained small amounts of only one component, probably hexenyl acetate, distinguishable from background vapours. From disrupted leaf tissues of cauliflower, turnip, radish and wallflower at 30°, the predominant vapour component was cis-hex-3-enyl acetate, whereas allyl isothiocyanate was the chief component from Brassica juncea. Other minor components were also identified. Apart from isothiocyanates, the only sulphur-containing component identified from these crucifers was dimethyl disulphide which was detected only from cauliflower, particularly in vapour from disrupted curd tissue.     

Terpenoids and other constituents from Euphorbia bupleuroides

The phytochemical investigation of the roots of Euphorbia bupleuroides Desf. (Euphorbiaceae) yielded three new compounds named 4,20-dideoxy(4α)phorbol-12-benzoate-13-isobutyrate (1), 25-hydroperoxycycloart-3β-ol (2), and 3β,7β-dihydroxy-4α,14α-dimethyl-8β,9β-epoxy-5α-ergosta-24(28)-ene (3), together with 17 known compounds 4–20. Their structures were established from analysis of 1D (¹H, ¹³C and DEPT) and 2D NMR (COSY, HSQC, HMBC and NOESY) data, and of mass spectrometry (HRESIMS), and by comparison with literature data.     

Bis-iridoids and other constituents from Scabiosa semipapposa

Six undescribed bis-iridoids named Semipapposiridoids A–F (1–6) together with seventeen known compounds were obtained from the roots and aerial parts of Scabiosa semipapposa Salzm. ex DC. Among the known compounds, three lignans were isolated for the first time in Scabiosa species, whereas the other known constituents including iridoids, phenol glycosides and flavonoids were previously isolated from Scabiosa sp. Their structures were assigned on the basis of extensive 1D- and 2D NMR experiments (¹H, ¹³C, COSY, TOCSY, NOESY, HSQC, HMBC), mass spectrometry HR-ESI-MS and by comparison of their spectral data with those of literature values. To the best of our knowledge, this should be the first report on the bis-iridoids content of this plant; furthermore, the fact that the plant is rich in mono-and bis-iridoids will support chemotaxonomy of the genus. The total phenolic and flavonoid contents of the 80% MeOH extracts and fractions were evaluated, with their antioxidant activities using three different methods, namely DPPH, ABTS and CUPRAC. Most of the fractions showed a moderate to good antioxidant activity compared to the standards BHA and BHT.     

Eudesmanolides and other constituents from Dimerostemma asperatum

The investigation of Dimerostemma asperatum afforded four new eudesmanolides, two unusual acetylenic esters and two diterpene lactones related to g