Henk Hendriks

Analytical aspects of phytotherapeutic valerian preparations

A high performance liquid chromatographic method combined with diode array detection is described by which the valerian constituents valtrate, isovaltrate, acevaltrate, didrovaltrate, isovaleroxyhydroxydidrovaltrate, valerenic acid, hydroxyvalerenic acid and acetoxyvalerenic acid, as well as the valepotriate decomposition products baldrinal and homobaldrinal, can be separated and identified simultaneously. Using this procedure, roots of Valeriana officinalis, which are used for the production of phytomedicines, were analysed. The influence of different ethanol:water mixtures, used as extraction liquid, on the composition of extracts of V. officinalis is reported. The analytical procedure was also applied to a number of valerian-containing phytomedicines available on the Dutch market. In order to study the stability of the valepotriates and the formation of their decomposition product(s), samples of freshly prepared valerian tinctures were analysed after being stored at 4, 20, and 36 degrees C for up to one month.

The essential oil of Tanacetum parthenium (L.) Schultz-Bip.

The composition of the essential oil of Tanacetum parthenium (L.) Schultz-Bip. (feverfew; Asteraceae) of various origins was investigated using GC and GC-MS. Camphor and chrysanthenyl acetate were the main constituents of the samples originating from England and The Netherlands. No infraspecific variation in the composition of the oil was found. Furthermore, the essential oil content and composition of Dutch feverfew during a vegetative period was studied. The young herb, before the formation of the stems, yielded a relatively high percentage of oil (0.53%, v/w), calculated on the dry weight. After a sharp decline at the beginning of the formation of the stems (0.30%, v/w), the percentage of the oil increased until full bloom (0.83%, v/w). During the development of the plant the percentage of camphor rose from 28% to 48%, whereas the amount of chrysanthenyl acetate decreased from 30% to 22%. In none of the oil samples investigated could the potentially toxic monoterpenes α- or β-thuojone be detected. This is important, because feverfew is used over long periods of time as a migraine prophylactic agent. The sesquiterpene lactone parthenolide is held responsible for this biological activity. In addition, chrysanthenyl acetate may display an analgesic effect by inhibiting the enzyme prostaglandin synthetase. Based on the results of our investigations and literature data, a number of recommendations are proposed with respect to the essential oil of T. parthenium.

Composition of the essential oil from roots and rhizomes of Valeriana wallichii DC.

The volatile constituents isolated from roots and rhizomes of Valeriana wallichii DC. ( = V. jatamansi Jones) were investigated by GC and GC–MS (EI and NICI) analysis. The plant material was obtained from different sources, namely from a local market in Kathmandu (Nepal), from plants grown in The Netherlands and in Germany, and from commercially available material from several German importers. The various roots and rhizomes yielded between 0.09 and 1.30% (v/w) essential oil on a dry weight basis. The main constituents of the oils from the plants grown in Europe were an unidentified sesquiterpene hydrocarbon, α-santalene, ar-curcumene and xanthorrhizol. In the oils from the Nepalese material and from the commercially available roots, except in one sample, patchouli alcohol was the main component.

Isolation and identification of valerenane sesquiterpenoids from Valeriana officinalis

Abstract Seven new valerenane sesquiterpenoids were isolated from a dichloromethane extract of Valeriana officinalis . The NMR, IR and mass spectral data of the isolated compounds, including the valerenic acids, are given in this paper.

Essential oil of two chemotypes of Mentha suaveolens during ontogenesis

Abstract The composition of the main constituents of the essential oil of two different chemotypes of Mentha suaveolens has been investigated during development. In the first chemotype (6) a definite increase of 1,2-epoxymen-thylacetate was observed, but piperitone oxide was always the main constituent. In the second chemotype (12) an increase of neo- and dihydrocarveol and their corresponding acetates was observed and dihydrocarvone was the main constituent. The results have been used to formulate a new biosynthetic scheme for the cyclic oxygenated monoterpenes found in essential oils of the genus Mentha .

Composition of the essential oils from underground parts of Valeriana officinalis L. s.l. and several closely related taxa

The volatile constituents from roots and rhizomes of Valeriana officinalis L. s.l. and of several closely related Valeriana taxa were investigated by GC and GCMS (EI and NICI) analysis. Seeds were obtained from different botanical gardens in Europe, and the plants investigated were grown in an experimental field in The Netherlands. In addition, commercially available plant material of Dutch origin was investigated. Four subspecies of the collective species V. officinalis were included in the study. The roots and rhizomes of 16 V. officinalis ssp. officinalis samples yielded 0.22-1.55% (v/w) essential oil on a dry weight basis. Oil components present in all samples were bornyl acetate (2-36%), myrtenyl acetate (trace-9%), nojigiku acetate (trace-0.8%), valerenic acid (0.3-3%), and one as yet unidentified tertiary sesquiterpene alcohol. The oil yield for the two samples of V. officinalis ssp. collina (Wallr.) Nyman was 0.78-0.85% (v/w). The main components were bornyl acetate (22-24%), myrtenyl acetate (6-8%), camphene (4-7%), kessane (3-6%), beta-eudesmol (4-5%) and a tertiary sesquiterpene alcohol (RI=1622) amounting to 20%, which was present in one sample only. For seven samples of V. officinalis ssp. sambucifolia (Mikan f.) Celak the yield of oil was 0.191.57% (v/w), with main components bornyl acetate (4-25%) and valerianol (3-34%). The only sample of V. repens Host. yielded 0.34% (v/w) oil, with bornyl acetate (13%), valerianol (19%) and kessane (8%) as the main components. Among the other (sub)species investigated in this study, the oil of V. celtica L. ssp. norica Vierh. contained bornyl acetate (22%) and patchouli alcohol (5%). Patchouli alcohol was also present in the oil of the two samples of V. phu L. together with gamma-patchoulene, patchoulyl acetate and a valerenal isomer (15-19%). Valeranone (16%) was the main constituent of the oil of V. exaltata Mikan. Bornyl acetate and valerianol were present in the essential oils of the other related valerian taxa studied

ALKALOIDS OF SOME EUROPEAN AND MACARONESIAN SEDOIDEAE AND SEMPERVIVOIDEAE (CRASSULACEAE)

Some 22 pyrrolidine and piperdine alkaloids were detected in the leafy parts of Sedum acre, S. aetnense, S. anglicum, S. brissemoreti, S. farinosum, S. fusiforme, S. lancerottense, S. melanantherum, and S. nudum. In addition to the alkaloids known from S. acre, 1-(2-pyrrolidyl)-propan-2-one and 2-monosubstituted piperidine alkaloids bearing butan-2-one, butan-2-ol, pentan-2-one and pentan-2-ol sidechains were identified. Phenylethylamine was isolated from the vegetative parts of S. album. In S. lydium, S. meyeri-johannis, and 16 species of S. series Rupestria, Aeonium, Greenovia, Jovibarba and Sempervivum no alkaloids could be detected. The results indicate a correlation between the presence of alkaloids and the major evolutionary trends in the European and Macaronesian Crassulaceae.

The composition of the essential oil in the leaves of Coleus aromaticus Bentham and their importance as a component of the species antiaphthosae Ph. Ned. Ed. V.

The leaves ofColeus aromaticus Bentham were used in the East Indian archipelago, mainly in cases of aphthous stomatitis. For this purpose the Dutch Pharmacopoeia Ed. v introduced the Species antiaphthosae withColeus leaves as an active component, because of their antiseptic qualities. Older research ascribed this activity to carvacrol and perhaps thymol. However, in more recent research in India eugenol and methyleugenol were also found to occur in this oil. Our investigations on original leaves from Java byGC-MS showed the absence of eugenol and methyleugenol, which leads us to the conclusion that on Java another chemotype occurs.

The origin of mentha — gracilis (Lamiaceae). II. essential oils

Essential oils were eamined in nine clones of Mentha arvensis, four clones of M. spicata, and 20 clones of M. gracilis. An F1 hybrid of M. arvensis M. spicata, selected on the basis of morphology and chromosome number, was matched with one clone of M. Gracilis. Genes for the inheritance of limonene, 1,8-cineole, linalool, isomenthone, carvone, and piperitenone oide were identified in one clone of M. arvensis and two clones of M. spicata. The range of essential oil compounds detected indicates that no one character can be used to identify M. gracilis, but the critical compounds of the oil of M. gracilis can be derived from crosses of M. arvensis M. spicata.ResumenDe Samenstelling van de vluchtige olie van negen klonen van Mentha arvensis, vier klonen van M. spicata en 20 klonen van M. gracilis werd onderzocht. Een F1 hybride van M. arvensis M. spicata, geselecteerd op basis van morphologische kenmerken en Chromosomen aantal, werd gekruist met een kloon van M. gracilis.De genen voor de overrevingvanlimoneen, 1,8-cineole, linalool, isomenthone, carvone en piperitenone oide werden geidentificeerd in een kloon van M. arvensis en in twee klonen van M. spicata. De reeks van verbindingen, die zijn aangetoond in de vluchtige olie wijst er op dat geen enkele verbinding kan worden gebruikt om M. gracilis te identificeren maar dat de kritische verbindingen in de olie van M. gracilis kunnen worden verkregen uit kruisingen van M. arvensis M. spicata.

Essential Oil Composition of Valeriana officinalis ssp. collina Cultivated in Bulgaria

Abstract The essential oils obtained from air-dried subterranean parts of Valeriana officinalis ssp. collina (Wallr.) Nyman (Valerianaceae), ‘Shipka,’ was analyzed by GC and GC/MS, and 62 components were identified. The oil yield, collected in plants grown in 1995 and 1998, was 0.42% (v/m) and 0.40% (v/m) respectively, related to the air-dried roots. Two new sesquiterpenes, (–)-pacifigorgia-l(6),10-diene and (–)-valerena-4,7(11)-diene were identified for the first time in both oils. Some major constituents were bornyl acetate (6.0%-7.3%), spathulenol (5.2%-4.1%), valeranone (12.0%-6.8%), valerenal (9.1%-8.5%), α-kessyl acetate (2.1%-6.2%) and (–)-valerena-4,7(11)-diene (7.2%-4.6%).