Dark-centred umbels in Apiaceae: diversity, development and evolution.

The wild carrot (Daucus carota) is famous for its dark flowers in the umbel centre. Several studies have been conducted to figure out their functional significance, but the evolution of the dark centre remains an enigma. In the present paper, we consider all known apioid species with dark-centred umbels to get a deeper understanding of their biology and evolution. Based on herbaria studies, literature and field work, we reconstructed the distribution area of 10 species (7 genera, 6 clades) of Apiaceae-Apioideae. To recognize homology of the dark structures, developmental studies were conducted in Artedia squamata and Echiophora trichophylla Field studies included architecture, flower morph distribution (andromonoecy) and flowering sequence within the plants, abundancy and behaviour of umbel visitors and preliminary manipulation experiments (removal/adding of dark structures). The dark structures are not homologous to each other. In the Daucus alliance, central flowers or umbellets are conspicuous, whereas in other species dark brush-like (A. squamata) or club-shaped structures (Dicyclophora persica, Echinophora trichophylla, Tordylium aegyptiacum, T. cappadocicum) develop from a naked receptacle. Species are andromonoecious, have a modular architecture and flower in multicyclic protandrous sequence. Among the many umbel visitors, beetles were the most abundant group. Only visitors found on umbels in both flowering phases were recognized as possible pollinators. Manipulation experiments indicated that the dark structures influence the behaviour of some, but not all umbel visitors. In Echinophora trichophylla, a massive gall infection was observed. It is evident that the dark structures evolved several times in parallel. The brush- and club-shaped structures are interpreted as the results of mutations affecting umbel development. Dark umbel centres are most likely stabilized by selection due to their general adaptive function. Their appearance in an area known as a hotspot of beetle pollination gives rise to the assumption that they may act as beetle marks.

Astrodaucus persicus as a new source of bioinsectisides against malaria vector, Anopheles stephensi.

OBJECTIVE: To determine the larvicidal activities of petroleum ether, chloroform, ethyl acetate and methanol fractions of roots and fruits extracts of Astrodaucus persicus from Apiaceae family against malaria vector, Anopheles stephensi (An. stephensi). METHODS: Twenty five third instar larvae of An. stephensi were exposed to various concentrations (10-160 g/L) of fractions and were assayed according to World Health Organization protocol. The larval mortality was calculated after 24 h treatment. RESULTS: Among tested fractions, the highest larvicidal efficacy was observed from ethyl acetate fraction of fruits extract with 50% and 90% mortality values (LC50 and LC90) of 34.49 g/L and 108.61 g/L, respectively. Chloroform fraction of fruits extract was the second larvicidal sample with LC50 of 45.11 g/L and LC90 of 139.36 g/L. Petroleum ether fractions of fruits and roots and methanol fraction of fruits showed moderate toxicity against An. stephensi. CONCLUSIONS: Astrodaucus persicus is a potential source of valuable and natural larvicidal compounds against malaria vector, An. stephensi and can be used in mosquitoes control programs as an alternative to synthetic insecticides.

Phytochemical and Antioxidant Investigation of the Aerial Parts of Dorema glabrum Fisch. & C.A. Mey.

Dorema glabrum Fisch. & C.A. Mey. (Apiaceae) is a monocarpic perennial plant distributed in southern Caucasus. In Azerbaijan Republic folk medicine, the gum-resin of this species is used as a diuretic and anti-diarrheal agent. It is also traditionally used for the treatment of bronchitis and catarrh. In the present study, chemical constituents of the essential oil and extract of D. glabrum aerial parts were investigated and their free radical scavenging potentials were assessed. GC-MS and GC-FID analyses of the plant essential oil resulted in identifying twenty compounds, out of which elemicin (38.6%) and myristicin (14.3%) were main compounds. Seven compounds including daucosterol (1), chlorogenic acid (2), a mixture of cynarin (3) and 3,5-di-O-caffeoylquinic acid (4), isorhamnetin-3-O-ß-D-glucopyranoside (5), isoquercetin (6) and astragalin (7) were also isolated from the ethyl acetate and methanol fractions of D. glabrum aerial parts using different chromatographic methods on silica gel (normal and reversed-phase) and sephadex LH20. Structures of the isolated compounds were elucidated using UV and (1)H, (13)C-NMR spectrain comparison with those reported in respective published data. Antioxidant activities of the crude extract, fractions and isolated compounds were evaluated using DPPH free radical scavenging assay method. Among the fractions, methanol fraction (IC50=53.3 ±4.7µg mL(-1)) and among the isolated compounds, caffeoylquinic acid derivatives exhibited the highest free radical scavenging activity (IC50= 2.2-2.6 µg mL(-1)).

Presence of phthalate derivatives in the essential oils of a medicinal plant Achillea tenuifolia.

BACKGROUND: Phthalate, esters of phthalic acid, are mainly applied as plasticizers and cause several human health and environment hazards. The essential oils of Achillea species have attracted a great concern, since several biological activities have been reported from varieties of these medicinal species. On the other side, due to the problems regarding the waste disposal in developing countries, phthalate derivatives can easily release from waste disposal to the water and soil resulting in probable absorption and accumulation by medicinal and dietary plants. As a matter of fact, although the toxicity of phthalate derivatives in human is well-known, food crops and medicinal plants have been exposing to phthalates that can be detected in their extracts and essential oils. Achillea tenuifolia (Compositea) is one of these herbaceous plants with traditional applications which widely growing in Iran. FINDING: The plant root was subjected to hydro-distillation for 4 h using Clevenger type apparatus to obtain its essential oil before and after acid treatment. Both of the hydro-distilled essential oils were analysed by GC-MS method resulted in recognition of their constituent. Phthalate contamination as (1, 2-benzenedicarboxylic acid, bis (2-methylpropyl) ester (5.4%) and phthalic acid (4.5%), were identified in the first and second extracted oils, respectively. CONCLUSION: As a warning, due to the potential role of phthalates to cause reproductive toxicity, disturb of endocrine system and causing cancers, medicinal plants have to be considered through quality control for detection of these compounds.

Quantification of verbascoside in medicinal species of Phlomis and their genetic relationships.

BACKGROUND: The genus Phlomis (Lamiaceae) is introduced by its valuable medicinal species, of which 17 species are growing wildly and ten of them are exclusively endemic of Iran. The main phytochemical characteristic of this genus is presence of iridoid glycosides including ipolamide, auroside, lamiide and also phenylethanoids such as verbascoside (acetoside) found in Lamiales order.Due to the broad range of biological and pharmacological activities of verbascoside and lack of any report on quantification of this compound within Iranian species of Phlomis, we conducted a research to achieve two main goals, finding a genetic biodiversity by RAPD (Randomly Amplified Polymorphic DNA), as well as detecting and quantifying verbascoside in nine species of Phlomis growing wildly in Iran. RESULTS: The results showed that various samples of P.olivieri possess different genetic distances from each other. Also, various species of P.olivieri display close relationships to P.anisodonta and P. persica. Phytoanalysis of Phlomis species by means of TLC scanner using verbascoside as a phytochemical marker showed that the highest concentration of verbascoside was found in P. anisodonta, however, P. bruguieri and P. olivieri (from Mazandaran) were in the second and third places. Interestingly, the lowest concentration of verbascoside was detected in P. olivieri (from Azerbayjan), exhibiting the effect of various growing areas and conditions on the measured levels of this compound. CONCLUSIONS: verbascoside can be found in various species of Iranian Phlomis, of which P. anisodonta, P. bruguieri and P. olivieri might be the best choices. In addition, although the concentration of verbascoside in these plants may be affected by the growing areas and conditions, there are a good agreement between genetic relations and verbascoside levels.

Alpha-amylase inhibitory activity and phytochemical study of Zhumeria majdae Rech. f. and Wendelbo.

BACKGROUND: Zhumeria majdae (Lamiaceae) is an endemic species growing in the South parts of Iran especially Hormozgan province. The plant is so-called Mohrekhosh locally and widely used for medicinal purposes including stomachache and dysmenorrhea. OBJECTIVE: In order to separation and identification of the main flavonoid glycosides of the plant (aerial parts including leaves, stems, flowers, and fruits were used) and evaluation of its alpha-amylase inhibitory (AAI) activity, methanolic extract was prepared and fractionated to botanolic portion. MATERIALS AND METHODS: Isolation of the main compounds of the butanol extract of the plant have been performed using different column chromatography methods such as high-performance liquid chromatography (C18 column) and Sephadex LH-20 as well. The isolated compounds were identified by Hydrogen-1 nuclear magnetic resonance and Carbon-13 nuclear magnetic resonance spectra and comparison with those reported in previous literature. Moreover, inhibitory activity of the butanolic extract of the plant against alpha-amylase enzyme was examined in different concentrations (15-30 mg/mL), where acarbose used as a positive control. RESULTS: Three flavonoid glycosides: Linarin (1), hispidulin-7-O-(4-O-acetyl-rutinoside) (2), hispidulin-7-O-rutinoside (3) were successfully identified in the extract. The activity of alpha amylase enzyme was dose-dependently suppressed by the butanol extract. The extract exhibited the highest inhibition at 30 mg/mL toward enzyme (77.9 ± 2.1%), while acarbose inhibited the enzyme at 20 mg/mL by 73.9 ± 1.9%. The inhibitory concentrations of 50% for the extract and acarbose were calculated at 24.5 ± 2.1 and 6.6 ± 3.1 mg/mL, respectively. CONCLUSION: Z. majdae contains glycosylated flavones and could be a good candidate for anti-diabetic evaluations in animal and clinical trials due to possessing AAI activity.

Flavones and Flavone Glycosides from Salvia macrosiphon Boiss.

Salvia genus, which is generally called Maryam-Goli in the Persian language, belongs to Lamiaceae family and comprises 58 species in Iran. Four flavonoids plus a steroid compound were isolated from the ethyl acetate and methanol extracts of the aerial parts of Salvia macrosiphon Boiss, using different chromatographic methods on the silica gel and sephadex LH20. The structures of the isolated compounds were determined to be apigenin-7, 4'-dimethyl ether (1), ß-sitosterol (2), salvigenin (3) apigenin-7-O-glucoside (4) and luteolin-7-O-glucoside (5) using the (1)H, (13)C-NMR and MS spectra in comparison with those reported in the literature.

Flavones and rosmarinic acid from Salvia limbata.

The genus Salvia (Lamiaceae) contains more than 50 shrub species in Iran, and Salvia limbata C.A. Meyer grows widely in the north and central parts of the country. Six flavones and rosmarinic acid were isolated from the ethyl acetate and methanol extracts of the flowered aerial parts of S. limbata collected from Semnan province. The separation process was carried out using several chromatographic methods. Structural elucidation was based on NMR data, in comparison with those reported in the literature. The isolated compounds were identified as ladanein (1), salvigenin (2), luteolin 7-methyl ether (3), cirsiliol (4), eupatorin (5), luteolin 7-O-glucoside (6) and rosmarinic acid (7). Some of these flavonoids have been reported to show antibacterial and cytotoxic activities.