Alkaloids from the roots of Zanthoxylum nitidum and their antiviral and antifungal effects

Five alkaloids, 5,6-dihydro-6-methoxynitidine (1), dictamnine (2), gamma-fagarine (3), skimmianine (4), and 5-methoxydictamnine (5), were isolated from the roots of Zanthoxylum nitidum. Their structures and configurations were elucidated by spectroscopic methods and X-ray analysis. Compounds 1, 4, and 5 showed in vitro antiviral effect against hepatitis B virus, and compounds 2, 3, and 5 demonstrated marked antimitotic and antifungal activity.     

Pyrrolizidine alkaloids from Senecio longilobus and Senecio glabellus

TLC, capillary GC, packed column and capillary GC-MS, and¹H NMR were used to characterize pyrrolizidine alkaloids fromSenecio longilobus andS.glabellus.S.glabellus contained senecionine and integerrimine, andS.longilobus contained senecionine, integerrimine, seneciphylline and retrorsine, all present predominantly asN-oxides. Alkaloid content varied greatly in collections ofS.longilobus. This is the first report of integerrimine in these plants.     

Furanoeremophilanes from Senecio smithii

The investigation of Senecio smithii afforded 17 furanoeremophilanes, six of them being isolated for the first time. Furthermore, two new bisabolon     

New sesquiterpenes from Senecio oxyodontus

The South African plant, Senecio oxyodontus, contained in addition to known compounds several new sesquiterpenes, which were all of the bisabolene type. The structures were elucidated by spectroscopic methods and some chemical transformations. The constituents were closely related to those from one other South African Senecio species and in contrast to most Senecio species which contain very different structural types, mainly of the furanoeremophilanes type.     

Cacalol derivatives from Senecio lydenburgensis

An investigation of Senecio lydenburgensis afforded eight new cacalol and cacalohastin derivatives. Their structures were deduced from the molecular formulae and ¹H NMR spectra.     

New norsesquiterpenes from Senecio digitalifolius

The South African Senecio digitalifolius contain besides several known furanoeremophilanes three new norsesquiterpenes all related to bisabolene. The structures are elucidated by spectroscopic methods.     

An eremophilanolide from Senecio rosmarinus

The aerial parts of Senecio rosmarinus afforded, in addition to the already known compounds, a new sesquiterpenic lactone, 1-oxo-10βH-eremophila-7(11)-en-8α,12 olide. The structure was established by spectral studies in which 2D-NMR spectroscopy played an essential role.     

Sesquiterpenes from three Senecio species

Three succulent Senecio species afforded, in addition to known compounds, two further bisabolene derivatives, a norsesquiterpene and a diol related to β-caryophyllene alcohol, which, however, has a different stereochemistry. Structures were elucidated by spectroscopic methods and some chemical transformations. The chemotaxonomic relevance of the results is discussed briefly.     

Notonipetrone-like sesquiterpenes from Senecio Kleinia

Five new notonipetrone-like sesquiterpenes have been isolated from the roots of Senecio kleinia and their structures elucidated.     

Sandaracopimarene derivatives from Senecio subrubriflorus

Several new sandaracopimarene derivatives were isolated from Senecio subrubriflorus. A triphenyl acetate of shikimic acid and a 4, 7-oxide of bisabolene were also present. The structures were elucidated by high field ¹H NMR spectroscopy. The chemistry of this species differs considerably from that of other Senecio species.     

Two sesquiterpenes from Senecio species

The investigation of further Senecio species gave, in addition to known compounds, two new sesquiterpenes, an eremophilane and a eudesmane derivative.     

Eremophilane derivatives from Senecio species

The investigation of two further Senecio species afforded two new furanoeremophilanes, four eremophilanolides and a new hydroxyeremophilane. The structures of two furanoeremophilane, isolated before, have been revised.     

Biochemical properties of Streptococcus macedonicus strains isolated from Greek Kasseri cheese

A total of 32 Streptococcus macedonicus strains, isolated from Greek Kasseri cheese, were screened for biochemical properties of technological importance in milk fermentation processing, such as acid production, proteolytic and lipolytic activity, citrate metabolism, exopolysaccharide production, antimicrobial activity and biogenic amines production. All strains were found to be moderate acidifiers in milk. Only four strains could hydrolyse milk casein, while 11 strains showed lipolytic activity against tributyrin. Using amino acid derivatives of 4-nitroaniline as substrates, the highest peptidase activities were determined against phenylalanine- and glycine-proline-4-nitroanilide. Using fatty acid derivatives of 4-nitrophenol, it was shown that all strains exhibited esterase activities up to caprylate, with highest values against butyrate and caproate. Only one showed activity up to palmitate; this was also the most active strain against tributyrin. Five of the 32 strains could metabolize citrate but none of them produced exopolysaccharides. Nine strains displayed antimicrobial activity towards Clostridium tyrobutyricum, while no antimicrobial activity was detected against Listeria innocua and Propionibacterium freudenreichii subsp. shermanii. Finally, none was able to decarboxylize ornithine, histidine or lysine, and only four strains produced tyramine from tyrosine.     

Acetophenones and terpenoids from Senecio Gallicus

Six new compounds isolated from the aerial part of Senecio gallicus were: 7,11,15-trimethyl-3-methylene hexadecan-1,2-diol diacetate; 7,11,15-trimethyl-3-methylenehexadecan-1,2-diol; 3,5-bis(3-methyl-2-butenyl)-4-acetoxyacetophenone; 3-(2-hydroxy-3-methyl-3-butenyl)-5-(3-methyl-2-butenyl)4-hydroxacetophenone; 3-(2,3-dihydroxy-3-methyl-butyl)-5-(3-methyl-2-butenyl)-4-hydroxyacetophenone and 1,10-epoxy-8α-hydroxy eremophilenolide.     

Two New Furanoeremophilanes from Senecio santelisis

From an Argentine collection of Senecio santelisis Phil ., the new furanoeremophilanoids, (10βH)‐6β‐acetoxy‐1α‐hydroxyfuranoeremophilan‐9‐one ( 1 ) and (10βH)‐1α‐hydroxy‐6β‐(propanoyloxy)furanoeremophilan‐9‐one ( 2 ), together with the known (10αH)‐6β‐acetoxy‐1α‐hydroxyfuranoeremophilan‐9‐one ( 3 ), (10αH)‐1α,6β‐diacetoxyfuranoeremophilan‐9‐one ( 4 ), and (10αH)‐1α‐hydroxy‐6β‐(propanoyloxy)furanoeremophilan‐9‐one ( 5 ) were isolated. Their structures and relative configurations were established on the basis of spectroscopic analysis. CHCl₃ Extract and pure compounds were evaluated for their antifungal activity. Compound 5 exhibited remarkable mycelial growth inhibition against B. cinerea with an IC₅₀ value of 21.4 μg/ml.