Pentacyclic triterpene triols from calendula officinalis flowers

From the flowers of Calendula officinalis five pentacyclic triterpene trihydroxyalcohols were isolated and identified as: olean-12-ene-3β,16β,28-triol, lup-20(29)ene-3β,16β,28-triol, tarax-20-ene-3β,16β,22α-triol, tarax-20-ene-3β,16β,30-triol and ursa-12-ene 3β,16β,21-triol, by chromatographic and spectroscopic means.     

Steroids from the roots of Asparagus officinalis and their cytotoxic activity

One new (Sarsasapogenin O) and seven known steroids were isolated from the roots of Asparagus officinalis L. Their structures were elucidated on the basis of spectroscopic analysis, including various 2D-NMR techniques, hydrolysis,and by comparison of spectral data of known compounds. These compounds together with nine steroids which were previously isolated from this plant, were tested for cytotoxic activity. Among them, eight compounds displayed significant cytotoxicities against human A2780, HO-8910, Eca-109, MGC-803, CNE, LTEP-a-2, KB and mouse L1210 tumor cells.     

Aromatic monoterpenes from Lavandula gibsonii

Three aromatic monoterpenes, not reported previously as natural products, together with ursolic acid, were isolated from Lavandula gibsonii. They were characterized as 3-hydroxy-α,α,4-trimethyl benzyl alcohol, 3-hydroxy- α,α,4-trimethyl benzyl methyl ether and 3-hydroxy-α,4-dimethyl styrene.     

Different kinds of male flowers in the dioecious plant Asparagus of officinalis L.

Summary In the dioecious plant Asparagus officinalis L. the female plants bear flowers that are all strictly of the same type, with well-developed pistils and collapsed and consistently sterile rudiments of anthers, while male plants, on the contrary, show a great variety of vestigial female organs, from small, rudimentary ovaries with no style and stigma, up to pistils provided with a rather long style that is often enlarged in a stigma. In our investigations, we used homozygous male and female doubled haploid plants obtained from in vitro anther culture, the all-male F₁ progeny and male individuals from subsequent backcrosses. The results showed that: (1) the character length of the style is genetically inherited and involves at least two genes, the influence of the environment being quite negligible; (2) in male pistils provided with style and stigmatic papillae, the pollination and growth of the pollen tubes up to the ovules do actually occur as a rule, the only barrier to fertilization being the absence of normal embryo sacs inside the ovules; (3) the character length of the style is a very reliable marker of the trend towards hermaphroditism in Asparagus, since a correlation always exist between length of the style, size of the ovary, tendency to self-pollination, vascularization and rate of development of the ovules inside the male ovaries. On the whole, most of our observations, together with the high inbreeding depression observed when occasional andromonoecious plants are selfed, are consistent with the hypothesis of the origin of dioecy in Asparagus from hermaphroditism via the gynodioecy pathway.     

Necrodane monoterpenoids from Lavandula luisieri

Four new irregular monoterpenoids were identified in the essential oil of Lavandula luisieri (Rozeira) Riv. Mart., a Labiatae endemic to the Iberian Peninsula. By means of spectroscopic and chemical methods, they were characterised as 3,5-dimethylene-1,4,4-trimethylcyclopentene, 5-methylene-2,3,4,4-tetramethylcyclopent-2-enone, 3,4,5,5-tetramethylcyclopenta-1,3-dienecarboxaldehyde and 3,4,5,5-tetramethylcyclopenta-1,3-dienecarboxylic acid. L. luisieri essential oil and extract showed a good activity against Candida albicans and gram positive bacteria: Staphylococcus aureus, S. epidermidis and S. pyogenes.     

2-N-Phenylaminonaphthalene from Lavandula vera

The aerial parts of Lavandula vera afforded a new natural aromatic substance, which was identified as 2-N-phenylaminonaphthalene.     

Indole alkoloids from Nauclea officinalis with weak antimalarial activity

Five indole alkaloids (naucleofficines A-E) were isolated from the stems (with bark) of Nauclea officinalis: (E)-2-(1-beta-d-glucopyranosyloxybut-2-en-2-yl)-3-(hydroxymethyl)-6,7-dihydro-indolo[2,3-a]quinolizin-4(12H)-one (1), (E)-1-propenyl-12-beta-d-glucopyranosyloxy-2,7,8-trihydro-indolo[2,3-a]pyran[3,4-g]quinolizin-4,5(13H)-dione (2), (E)-2-(1-hydroxybut-2-en-2-yl)-11-beta-d-glucopyranosyloxy-6,7-dihydro-indolo[2,3-a]quinolizin-4(12H)-one (3), (E)-1-propenyl-4-hydroxy-2,4a,7,8,13b,14,14a-hepthydro-(4alpha,4abeta,13balpha,14abeta)indolo[2,3-a]pyran[3,4-g]quinolizin-5(13H)-one (4) and 1-(1-hydroxyethyl)-10-hydroxy-7,8-dihydro-indolo[2,3-a]pirydine[3,4-g]quinolizin-5(13H)-one (10-hydroxyangustoline) (5), together with two known compounds, naucleidinal (6) and angustoline (7). All of the structures of the seven compounds above were elucidated by spectroscopic methods including use of 1D- and 2D-NMR spectroscopic analyses. Compounds 2 and 3 are rare examples of monoterpene indole alkaloids with a glucopyranosyloxy group attached to position C-12. In vitro activity screening of the above seven compounds showed weak to moderate inhibitory activity against Plasmodium falciparum.     

Senescence regulation by alcohols in cut flowers of Calendula officinalis L.

This study was conducted to investigate the effect of alcohols viz., ethanol, methanol and n-butanol at different concentrations not only on the vase life of Calendula officinalis L. cut flowers but also to record changes in metabolites like starch content and amount of sugars, and activities of α-amylase, and antioxidant enzymes like peroxidase and superoxide dismutase as well as lipid peroxidation. Ethanol as holding solution significantly increased the vase life as compared to other treatments or the control. n-Butanol shortened vase life and caused the flower stem to fold, whereas ethanol and methanol individually delayed drying up and petals dried slowly from their tips. Significant increments in solution uptake, moisture content and flower diameter were noticed with 2 % ethanol followed by 2 % methanol. Cut scapes having 2 % ethanol exhibited maximum amount of starch and considerably lower amount of reducing and non-reducing sugars. This treatment not only brings down the specific activities of α-amylase and peroxidase but also decreases the process of lipid peroxidation. Effectiveness of methanol (2 %) is evident just after ethanol application (2 %). Lowest concentrations of ethanol and methanol also show relatively higher level of SOD activity in cut flowers of Calendula officinalis.     

Subcellular distribution of free and ester-bound triterpene triols in Calendula officinalis flowers

In cellular subfractions obtained from Calendula officinalis ligulate flowers, the contents of individual free and ester-bound triterpene triols, as well as fatty acid components of the ester form, were determined. It was shown that triterpene triols are localized only in the chromoplast fraction, almost exclusively in a free form and in a very small amount as monoesters. The compositions of fatty acids esterifying triols were similar to those esterifying diols in chromoplasts.     

Phytochemicals from the genus Lavandula: a review

Phytochemistry Reviews - The genus Lavandula occurs naturally in the Mediterranean basin and its species are a rich source of phytochemicals. Species of this genus have attracted great interest,...     

Intracellular localization of metabolism of lupeol and its palmitate in Calendula officinalis flowers

In the non-fractionated flowers and in the chromoplast and extra-chromoplast fractions obtained from Calendula officinalis flowers the incorporation of radioactivity after incubation with [3-³H]lupeol and [3-³H]lupeyl[¹⁴C]palmitate were determined. It was shown that both precursors were metabolized. Monol esters are the main precursors of diol 3-monoesters, whereas free monols are hydroxylated to the diols and triols. The shape and course of the dynamic curves suggest that the process of hydroxylation of free monols, free diols and monol esters is situated only inside chromoplasts. On the other hand the hydrolysis of monol esters and esterification of free monols proceeds both outside and inside the chromoplasts.     

Structural characterization and anti-fatigue activity of polysaccharides from the roots of Morinda officinalis

Three polysaccharides MP-1, MP-2, and MP-3 were isolated from hot water extract of Chinese medicine Morinda officinalis through 95% ethanol precipitation and gel-filtration chromatography (DEAE-Sepharose CL-6B column and Sephadex G-75 or G-100 column). MP-1 was identified as an inulin-type fructan with simple linear (2 → 1)-linked structure. Both MP-2 and MP-3 were acidic polysaccharides which consisted predominantly of galacturonic acid, arabinose and galactose. Partial structure characterization of MP-3 was carried out by partial acid hydrolysis and periodate oxidation. The total polysaccharides of the herb were tested in mice weight-loaded swimming model and were found to have anti-fatigue activity.     

Water-soluble polysaccharides from Salvia officinalis L. possessing immunomodulatory activity

A water-soluble polysaccharide complex (A) composed of galactose (17.9%), 3-O-methyl-galactose (3.0%), glucose (15.5%), mannose (8.3%), arabinose (30.4%), xylose (7.6%), fucose (2.6%), rhamnose (6.7%), and uronic acids (8.0%) has been isolated from the aerial parts of sage (Salvia officinalis L.) by cold water extraction. It showed a broad molecular-mass distribution pattern (Mw approximately 2000-93,000) with a predominance of polymers with Mw< 10,000. Ion-exchange chromatography of A afforded six polymeric fractions (A1-A6) in which arabinogalactans associated with galacturonan and/or rhamnogalacturonan backbones prevail. Sage polysaccharides were examined for their immunomodulatory activity in the comitogenic thymocyte test which is interpreted as being an in vitro correlate of adjuvant activity. The acidic polysaccharide fractions A2, A3 and A4 exhibited the highest mitogenic and comitogenic activities of all fractions tested, and relatively high SI(comit)/SI(mit) ratios approximately 3 indicate potential adjuvant properties of these polysaccharides.     

Antiprotease and antimetastatic activity of ursolic acid isolated from Salvia officinalis

Proteases play a regulatory role in a variety of pathologies including cancer, pancreatitis, thromboembolic disorders, viral infections and many others. One of the possible strategies how to combat with these pathologies seems to be the use of low molecular inhibitors. Natural products were evaluated in the in vitro antiprotease assay on serine proteases (trypsin, thrombin and urokinase) and on the cysteine protease cathepsin B. We found interesting results for beta-ursolic acid isolated from Salvia officinalis, which significantly inhibited all tested proteases in vitro in the micromolar range. beta-Ursolic acid showed the strongest inhibition activity to urokinase (IC50 = 12 microM) and cathepsin B (IC50 = 10 microM) as proteases included in tumour invasion and metastasis indicated possible anticancer effectivity. Therefore, we tested the ability of beta-ursolic acid at doses of 50, 75 and 100 mg/kg given i.p. to inhibit lung colonization of beta16 mouse melanoma cells in vivo. We found, that beta-ursolic acid significantly decreased the number of B16 colonies in the lungs of mice at the dose 50 mg/kg (p < 0.05).     

Essential oils from micropropagated plants of Lavandula viridis

The essential oils of Lavandula viridis were analysed by GC and GC-MS. Comparisons were made between three types of plant material from the same clone: field-grown plant, in vitro shoot cultures and micropropagated plants of the same clone. The most common components usually found in lavender oils were present in the oil samples analysed and more than 45 constituents were identified, representing more than 80% of the essential oil. The essential oils analysed consisted mainly of monoterpenes (75.4-76.3%), where oxygenated and hydrocarbons identified ranged from 41.8 to 57.3% and 18.1 to 34.2%, respectively. The major components found were 1.8-cineole (18.2-25.1%), camphor (9.1-15.7%), alpha-pinene (8.8-14.1%), borneol (4.1-4.8%), beta-pinene (1.2-5.6%), delta 3-carene (1.0-6.5%) and alpha-terpineol (0.8-4.2%). The monoterpene fraction of the in vitro shoot cultures showed different relative amounts of hydrocarbons and oxygenated components in relation to the parent plant and to micropropagated plants. In the sesquiterpene hydrocarbon fraction of the oil samples analysed (6.1-8.2%), 7-epi-alpha-selinene (1.6-4.8%) was the most important component and the oxygenated sesquiterpenes were found in small amounts (1.1-1.7%). The essential oils from field-grown plants of L. viridis, when compared with those obtained from in vitro shoot cultures or micropropagated plants of the same clone, demonstrated that the same major components were found without significant compositional variations.