Hyoscyamine (HYO) and scopolamine (SCO) are tropane alkaloids acting as anticholinergic factors on the parasympathetic nervous system in humans and are produced by Solanaceous plants. Two strains of ...Agrobacterium rhizogenes, A4 and LBA9402, were used to infect Atropa acuminata Royle ex Miers and Atropa belladonna L. leaf explants. A. acuminata was inoculated either by direct infection or sonicated‐assisted A. rhizogenes‐mediated transformation (SAAT) was performed. A. belladonna was inoculated with the A4 strain using a direct method. The selected hairy root lines of both species were elicited with 50 mM methyl‐β‐cyclodextrin (β‐CD), 0.5 μM coronatine (Cor) or 50 mM β‐CD + 0.5 μM Cor on Day 14 of culture. The elicitor effect on growth and HYO and SCO content was analyzed after one (T1) and two (T2) weeks of treatment. In A. acuminata explants, the highest transformation percentage (T%) was obtained with strain A4 and the SAAT method (T%: 96.43). Cor significantly reduced the growth of A. acuminata hairy roots (fresh weight and dry weight DW: 2.52 and 0.3 g, respectively), whereas β‐CD increased their DW (0.4 g). Also, the combined β‐CD + Cor treatment had a positive significant effect on the DW of A. belladonna hairy roots (0.41 g). In A. acuminata hairy roots, the HYO level was lower under Cor treatment than in the control at both sampling times. In contrast, the SCO content was increased 10‐fold by Cor elicitation at T1 compared to the control (10.95 mg g−1 DW) and was also positively affected by β‐CD + Cor. In A. belladonna hairy roots, all the elicitors had a negative effect on both HYO and SCO production. This report is the first assessment of the effect of β‐CD and Cor elicitors on tropane alkaloid production.
Rationale
Gas chromatography–mass spectrometry (GC–MS) is the most frequently applied technique for analyzing Amaryllidaceae alkaloids in plant extracts. Having these compounds, known for their ...potent bioactivities, is a distinctive chemotaxonomic feature of the Amaryllidoideae subfamily (Amaryllidaceae). The Amaryllidaceae alkaloids of homolycorine type with a C3–C4 double bond generally show molecular and diagnostic ions at the high‐mass region with low intensity in the EIMS mode, leading to problematic identification in complex plant extracts.
Methods
Eleven standard homolycorine‐type alkaloids (isolated and identified by 1D and 2D nuclear magnetic resonance) were subjected to separation with GC and studied with electron impact mass spectrometry (EIMS) including single quadrupole (GC–EIMS), tandem (GC–EIMS/MS), and high‐resolution (GC–HR‐EIMS) detectors, as well as with chemical ionization mass spectrometry (GC–CIMS). Alkaloid fractions from two Hippeastrum species and Clivia miniata were subjected to GC–EIMS and GC–CIMS for alkaloid identification.
Results
GC–EIMS in combination with GC–CIMS provided significant structural information of homolycorine‐type alkaloids with C3–C4 double bond, facilitating their unambiguous identification. Based on the obtained typical fragmentation, other 11 homolycorine‐type compounds were identified in extracts from two Hippeastrum species by parallel GC–EIMS, GC–CIMS, and liquid chromatography–electrospray ionization time‐of‐flight mass spectrometry and in extracts from C. miniata by GC–EIMS.
Conclusions
GC–MS can be successfully applied for the identification of new and known homolycorine‐type alkaloids, among others within the Amaryllidoideae subfamily, as well as for chemotaxonomical and chemoecological studies.
The search for novel bioactive compounds and the identification of known ones in the plant kingdom are a challenge for the scientists working in different fields of plant science. In the recent ...years, mass spectrometry is the most frequently applied method for analysis of complex mixtures of plant metabolites. Twenty‐two alkaloids of different lycorine skeleton subtypes (with a Δ3,4 double bond, with a Δ4,11 double bond, with saturated rings C and D, and with aromatic ring C) were subjected to separation with gas chromatography and studied with electron impact mass spectrometry including single quadropole (GC‐EIMS), tandem mass (GC‐EIMS/MS) and high resolution mass (EI‐HRMS) detectors in order to determine their fragmentation pattern. The compounds showed excellent separation and specific MS fragmentation allowing structural determination. The GC–MS can be successfully applied for searching new and identification of known bioactive molecules, chemotaxonomical and chemoecological studies, among others, within the Amaryllidoideae subfamily.
The Libellus de Medicinalibus Indorum Herbis (Booklet of Indian Medicinal Plants) is the first book of medicinal plants written in the American continent. It was first published in 1939 as ‘An Aztec ...Herbal’. One of the depicted plants is Huetzcanixochitl (laughing flower) interpreted as Zephyranthes fosteri (Amaryllidaceae). No chemical or pharmacological studies are reported for this species; so, we decide to investigate it. The GC/MS of the bulbs and aerial parts extracts indicated that they contain Amaryllidaceae alkaloids, among them: lycorine, 3‐O‐acetylpowelline, and norlycoramine. An unknown major alkaloid was isolated and identified by 1H, 13C‐NMR and MS, as 3′‐demethoxy‐6‐epimesembranol (1). The methanolic extract, the alkaloid fraction, and compound 1 inhibited acetylcholinesterase in vitro. Mesembrine alkaloids are found in Sceletium species (Aizoaceae). Several are known as serotonin recapture inhibitors and have been proposed as potential antidepressant drugs. The presence of 1 suggests that Z. fosteri was probably used in pre‐Columbian times in Mexico as a ‘stimulant and euphoriant’, alike Sceletium tortuosum by several ethnic groups in South Africa.
The genus
Herb. is found in the Andes Region (South America), mainly in Peru, Ecuador, and Bolivia. These plants belong to the Amaryllidaceae family, specifically the Amaryllidoideae subfamily, which ...presents an exclusive group of alkaloids known as Amaryllidaceae alkaloids that show important structural diversity and pharmacological properties. It is possible to find some publications in the literature regarding the botanical aspects of
species, although there is little information available about their chemical and biological activities. The aim of this work was to obtain the alkaloid profile and the anti-cholinesterase activity of four different samples of
collected in South America:
sp.,
, and
. The alkaloid extract of each sample was analyzed by gas chromatography coupled with mass spectrometry (GC-MS), and their potential against the enzymes acetyl- and butyrylcholinesterase were evaluated. Thirteen alkaloids have been identified among these species, while six unidentified structures have also been detected in these plants. The alkaloid extract of the
samples showed the highest structural diversity as well as the best activity against AChE, which was likely due to the presence of the alkaloid sanguinine. The results suggest this genus as a possible interesting new source of Amaryllidaceae alkaloids, which could contribute to the development of new medicines.
Chagas disease, caused by the protozoan Trypanosoma cruzi, is a neglected disease that affects ~7 million people worldwide. Development of new drugs to treat the infection remains a priority since ...those currently available have frequent side effects and limited efficacy at the chronic stage. Natural products provide a pool of diversity structures to lead the chemical synthesis of novel molecules for this purpose. Herein we analyzed the anti-T. cruzi activity of nine alkaloids derived from plants of the family Amaryllidaceae.
The activity of each alkaloid was assessed by means of an anti-T. cruzi phenotypic assay. We further evaluated the compounds that inhibited parasite growth on two distinct cytotoxicity assays to discard those that were toxic to host cells and assure parasite selectivity.
We identified a single compound (hippeastrine) that was selectively active against the parasite yielding selectivity indexes of 12.7 and 35.2 against Vero and HepG2 cells, respectively. Moreover, it showed specific activity against the amastigote stage (IC
= 3.31 μM).
Results reported here suggest that natural products are an interesting source of new compounds for the development of drugs against Chagas disease.
•An LC–DAD–ESI-MS method has been developed to identify and quantify the phenolic composition of Dracocephamum kotschyi.•We report a nutraceutical with a high content of antioxidant methoxylated ...flavonoids.•Morphological variability among wild populations was correlated with flavonoid accumulation.
Dracocephalum kotschyi Boiss. (Lamiaceae) is an aromatic and perennial herb endemic to Iran with interesting pharmacological and biological properties. The flavonoids luteolin-7-O-glucoside, apigenin-7-O-glucoside (cosmosiin), luteolin 3′-O-β-d-glucuronide, luteolin, apigenin, cirsimaritin, isokaempferide, penduletin, xanthomicrol, calycopterin and the polyphenol rosmarinic acid were identified among 13 natural populations of the plant by ESI–MS, LC–DAD and LC–DAD–ESI-MS. The plant extracts containing the identified compounds showed significant antioxidant activity, which was correlated with the flavonoid content. Additionally, leaf and stem size and geographical variability among the studied populations were correlated with flavonoid accumulation. Canonical correlation analysis was used to find a relationship between plant dimensions and phytochemical composition, and the plants with the lowest growth indices were found to have the highest levels of methoxylated flavonoids.
Amaryllidaceae alkaloids are secondary metabolites with interesting medicinal properties. Almost every
species can synthesize them and constitute an excellent source for their isolation and study. ...Several Amaryllidaceae alkaloids have shown acetylcholinesterase inhibitory activities and are a promising tool for treating cholinergic disorders such as Alzheimer's disease (AD). Indeed, three of the four palliative treatments approved for AD are acetylcholinesterase (AChE) inhibitors and one of them, galanthamine, is an Amaryllidaceae alkaloid itself. This molecule is currently isolated from natural sources. However, its production is insufficient to supply the increasing demand for the active principle. Our main aim is to discover tools to improve galanthamine production and to prospect for potential new and more efficient drugs for AD treatment. Furthermore, we seek to broaden the knowledge of plants of the genus
from a chemotaxonomic perspective. Hence, in this study, we evaluate the alkaloid content through GC-MS and the AChE inhibitory activity of ten autumn-flowering
, which have been less studied than their spring-flowering counterparts. A total of thirty Amaryllidaceae alkaloids have been found, twenty-eight properly identified. Two
contained galanthamine, and seven were able to inhibit AChE.
Natural products play an important role in the development of new drugs. In this context, the Amaryllidaceae alkaloids have attracted considerable attention in view of their unique structural ...features and various biological activities. In this study, twenty-three alkaloids were identified from
by GC-MS and two new structures (augustine
-oxide and buphanisine
-oxide) were structurally elucidated by NMR. Anti-parasitic and cholinesterase (AChE and BuChE) inhibitory activities of six alkaloids isolated from this species, including the two new compounds, are described herein. None of the alkaloids isolated from
gave better results than the reference drugs, so it was possible to conclude that the
-oxide group does not increase their therapeutic potential.
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