Wulf Schultze

Azaphilones: a class of fungal metabolites with diverse biological activities

This review presents an overview of azaphilones isolated from different species of fungi, detailing their chemical structures and biological activities as covered in the recent literature. Over 170 different azaphilone compounds occur in fungi belonging to 23 genera from 13 families: these azaphilones can be classified into ten different structural groups. Numerous azaphilone structures have been described, particularly from members of the Trichocomaceae and Xylariaceae families. Azaphilones exhibit a wide range of interesting biological activities, such as antimicrobial, antifungal, antiviral, antioxidant, cytotoxic, nematicidal and anti-inflammatory activities. Many of these effects may be explained by the reactions of azaphilones with amino groups, such as those found in amino acids, proteins and nucleic acids, resulting in the formation of vinylogous γ-pyridones.

Chemical Analysis and Biological Activity of the Essential Oils of Two Endemic Soqotri Commiphora Species

The barks of two endemic Commiphora species namely, Commiphora ornifolia (Balf.f.) Gillett and Commiphora parvifolia Engl., were collected from Soqotra Island in Yemen and their essential oils were obtained by hydrodistillation. The chemical composition of both oils was investigated by GC and GC-MS. Moreover, the essential oils were evaluated for their antimicrobial activity against two Gram-positive bacteria, two Gram-negative bacteria and one yeast species by using a broth micro-dilution assay for minimum inhibitory concentrations (MIC) and for their antioxidant activity by measuring the DPPH radical scavenging activity. A total of 45 constituents of C. ornifolia (85.6%) and 44 constituents of C. parvifolia (87.1%) were identified. The oil of C. ornifolia was characterized by a high content of oxygenated monoterpenes (56.3%), of which camphor (27.3%), α-fenchol (15.5%), fenchone (4.4%) and borneol (2.9%) were identified as the main components. High contents of oxygenated sesquiterpenes (36.1%) and aliphatic acids (22.8%) were found in C. parvifolia oil, in which caryophyllene oxide (14.2%), β-eudesmol (7.7%), bulnesol (5.7%), T-cadinol (3.7%) and hexadecanoic acid (18.4%) predominated. The results of the antimicrobial assay showed that both oils exhibited moderate to high antibacterial activity especially against Gram-positive bacteria. C. ornifolia oil was the most active. In addition, the DPPH-radical scavenging assay exhibited only weak antioxidant activities for both oils at the high concentration tested.

Über die Alkaloidzusammensetzung der oberirdischen Teile von Laburnum watereri (Kirchn.) Dipp.

Summary The alkaloid composition of the overground parts (leaves, petioles, stems, flowers, fruits and seeds) of Laburnum watereri (hybrid of Laburnum alpinum × L. anagyroides ) and its seasonal changes (from march to november) have been studied by different chromatographic (TLC, capillary GC) and spectroscopic (GC/MS, HRMS, 1 H-NMR, 13 C-NMR, IR, UV) methods. Seeds only contain cytisine. Besides cytisine, traces of methylcytisine and ammodendrine 12 further alkaloids could be identified in the fruits, among which β-isosparteine, 14e-hydroxysparteine and epi-baptifoline have been found for the first time in the genus Laburnum . Following the seasonal changes of the alkaloid composition of the fruits, an increase of epibaptifoline and ammodendrine was established during ripening, while the content of the main compound cytisine strongly declined. The highest total amount of alkaloids (with 80 to 90% cytisine) was found in the buds in the spring. During the further development of the leaves, the cystine content decreases and a methylation of this alkaloid begins. In summer the alkaloid concentration reaches the lowest level. In the course of July epi-baptifoline (erroneously reported as methylcytisine in literature) increases and becomes the main alkaloid for the following 6 months.

The Composition of the Essential Oils of Chaerophyllum hirsutum L.

ABSTRACT Comparison of the essential oils from different plant parts of Chaerophyllum hirsutum L. shows, that the qualitative composition of the oils of the above-ground parts is very similar, however, the percentage of individual components differs significantly. Among the monoterpene hydro-carbons β-pinene is the main constituent of the fruit oil where it is present in about 25%. In the stem and leaf oils, sabinene can be found in 58.2% and 25.9%, respectively. The important oxygenated terpenoids with distinctly different proportions are acorenone-B and a new sesquiterpene lactone with a guaiane skeleton. Acorenone-B occurs in the fruit oil up to 18%, in the leaf oil up to 9% and only in traces in the stem oil. The sesquiterpene lactone shows a similar distribution with about 4% in the fruit and leaf oils and very small amounts in the stem oil. The root oil of Chaerophyllum hirsutum exhibits a different qualitative pattern. The main constituents of this oil are common monoterpene hydrocarbons (94%) and ...

Composition of the Essential Oils of Ligusticum mutellina (L.) Crantz (Apiaceae)

ABSTRACT The volatile constituents of fruit, herb and underground parts of Ligusticum mutellina (L.) Crantz were studied by GC and GC/MS. The oils showed a different composition with the main class of compounds being phenylpropanoids with 57.6% (fruit), 49.5% (herb) and 30.2% (rhizome/roots). The major constituents are myristicin (35.1%) and apiole (17.4%) in the fruit oil, myristcin (39.3%) and α-phellandrene (23.4%) in the herb oil and myristicin (26.8%) and (Z)-ligustilide (19.1%) in the oil of the underground parts. Phthalides (23.9%) are characteristic compounds of the root/rhizome oil and could not be detected in the aerial parts of this plant.

Essential Oil of Haplophyllum linifolium (L.) G. Don fil. (Rutaceae)

Abstract The essential oils from the fruits and the aerial parts of Haplophyllum linifolium harvested in 1994 and 1997 were isolated by hydrodistillation, fractionated by dry column chromatography, and analyzed by GC and GC/MS. The GC of the fruits exhibited 68 peaks from which 50 substances were structurally identified by MS and RI-values, which correspond to 98.8% and 98.2% of the oils, respectively. The main components of these oils were β-phellandrene (25.5% and 35.5%) and β-pinene (23.7% and 21.2%), but the more interesting characteristic is the presence of 4.6% and 2.9% bornyl formate, respectively, a compound rarely found in essential oils. The oil of the aerial parts of the plant exhibited a very similar oil composition differing only in the percentual proportions. β-Phellandrene and β-pinene were the dominating constituents of the herb oils representing 42.6% (30.4%) and 19.8% (22.4%), respectively. Bornyl formate amounted to 2.5% in 1994 and 4.0% in 1997.

Composition of the Essential Oil of the Underground Parts of Geum montanum L. (Rosaceae)

ABSTRACT The constituents of the essential oil of the underground parts of Geum montanum L. were investigated by GC and GC/MS. Seventy-two compounds could be identified with (Z)-ligustilide (14.9%), α-phellandrene (8.5%) and dill apiole (7.7%) as main components. The occurrence of some phthalides and 2-penten-l-yl-l, 3-cyclohexadiene is noteworthy, since they are untypical compounds in essential oils of Rosaceae.

The Essential Root Oil of Peucedanum lancifolium Lange and Chemotaxonomic Implications

Abstract The composition of the essential root oil of Peucedanum lancifolium Lange (A piaceae), growing in the Atlantic coast regions of France, North-West Spain und Portugal was investigated by chromatographic and spectroscopic methods. Forty five terpenoids, many of them of already known structure, and several aliphatic esters have been identified. Besides the main constituent, the irregular sesquiterpene alcohol trans-sesquilavandulol, representing 53.37% of the total oil, some hitherto unknown sesquiterpenoids with an irregular carbon skeleton were found. The possible chemotaxonomic value of the essential oil com position with regard to the close botanical relationship of Peucedanum lancifolium Lange and Peucedanum palustre (L .) M oench is briefly discussed. With the exception of these two species, trans-sesquilavandulol was not found in any other member of the genus Peucedanum.

Flüchtige Inhaltsstoffe in pflanzlichen Zellkulturen — eine Übersicht

Summary The occurrence of volatile compounds in plant cell cultures has been reviewed, not including cultures of microorganisms and biotransformation studies. Volatiles of all types of cell cultures (liquid and solid medium; organized and unoganized growth, regenerated plantlets) have been considered. No studies on volatiles of cell cultures from algae and lichen could be found; only 4 were reported from the bryophytes and pteridophytes. The majority of investigations dealing with this subject has been performed on cell cultures, which derived from plants of the families of the Rutaceae, Apiaceae, Asteraceae and Lamiaceae .

Untersuchungen an Kalluskulturen von Melissa officinalis L., II Über wasserdampfflüchtige Diterpenkohlenwasserstoffe in nicht differenzierten Oberflächenkulturen / Investigations on Callus Cultures of Melissa officinalis L., II Votile Diterpene Hydrocarbons in Not Differentiated Static Cultures

Dehydroabietane and an other diterpene hydrocarbon, being still unidentified, were found in the steam distillates of callus cultures of Melissa officinalis. The relative proportions of these two diterpenes changed considerably during the course of a cultivation passage. With advancing age of the cells they shifted gradually towards dehydroabietane. Cultures being exposed to continuous light showed the same composition of their steam distillates as cultures which were raised in the dark.