Ten compounds, including two new alkaloidal glycosides
1 and
2, one new natural tetrahydronorharmine
4, four known
β-carbolines
3,
5–
7, two known proanthocyanidines
8 and
9, and one new disaccharide
...14 were isolated and identified from aqueous extract of
Banisteriopsis caapi. Extracts and their constituents were evaluated for MAO inhibitory and antioxidant activities.
Parkinson's disease is a neurological disorder mostly effecting the elder population of the world. Currently there is no definitive treatment or cure for this disease. Therefore, in this study the composition and constituents of the aqueous extract of
Banisteriopsis caapi for monoamine oxidases (MAO) inhibitory and antioxidant activities were assessed, which are relevant to the prevention of neurological disorders, including Parkinsonism.
The aqueous extract of
Banisteriopsis caapi stems was standardized and then fractionated using reversed-phase (RP) chromatography. Pure compounds were isolated either by reversed-phase (RP) chromatography or centrifugal preparative TLC, using a Chromatotron
®. Structure elucidation was carried out by 1D and 2D NMR, Mass, IR and Circular Dichroism spectroscopy and chemical derivatization. Chemical profiling of the extract was carried out with RP-HPLC. The inhibitory activity of MAO-A, MAO-B, acetylcholinesterase, butyrylcholinesterase and catechol-
O-methyl transferase enzymes, as well as antioxidant and cytotoxic activities of both
Banisteriopsis caapi extract and isolated compounds was evaluated.
An examination of the aqueous extracts of
Banisteriopsis caapi cultivar Da Vine yielded two new alkaloidal glycosides, named banistenoside A (
1) and banistenoside B (
2), containing “azepino1,2-atetrahydro-
β-carboline” unique carbon framework. One additional new natural tetrahydronorharmine (
4), four known
β-carbolines harmol (
3), tetrahydroharmine (
5), harmaline (
6) and harmine (
7), two known proanthocyanidines (−)-epicatechin (
8) and (−)-procyanidin B2 (
9), and a new disaccharide
β-
d-fructofuranosyl-(2
→
5)-fructopyranose (
14) together with known sacharose (
15) and
β-
d-glucose (
16) were also isolated. In addition, the acetates of
1,
2,
8,
9,
14 and
15 (compounds
10–
13,
17,
18) were also prepared. Harmaline (
6) and harmine (
7) showed potent
in vitro inhibitory activity against recombinant human brain monoamine oxidase (MAO)-A and -B enzymes (IC
50 2.5 and 2.0
nM, and 25 and 20
μM, respectively), and (−)-epicatechin (
8) and (−)-procyanidin B2 (
9) showed potent antioxidant and moderate MAO-B inhibitory activities (IC
50
<
0.13 and 0.57
μg/mL, and 65 and 35
μM). HPLC analysis revealed that most of the dominant chemical and bioactive markers (
1,
2,
5,
7–
9) were present in high concentrations in dried bark of large branch. Analysis of regular/commercial
Banisteriopsis caapi dried stems showed a similar qualitative HPLC pattern, but relatively low content of dominant markers
1,
2,
7, and
9, which led to decreased MAO inhibitory and antioxidant potency.
Collectively, these results give additional basis to the existing claim of
Banisteriopsis caapi stem extract for the treatment of Parkinsonism, including other neurodegenerative disorders.
HPLC was employed to profile the alkaloidal and non-alkaloidal components of the aqueous extract of
B. caapi. The extracts were simultaneously tested
in vitro for inhibition of human MAO-A and ...antioxidant activity in order to correlate phytochemical composition of the extracts and bioactivities.
Banisteriopsis caapi, a woody vine from the Amazonian basin, is popularly known as an ingredient of a sacred drink ayahuasca, widely used throughout the Amazon as a medicinal tea for healing and spiritual exploration. The usefulness of
Banisteriopsis caapi has been established for alleviating symptoms of neurological disorders including Parkinson's disease.
Primary objective of this study was to develop the process for preparing standardized extracts of
Banisteriopsis caapi to achieve high potency for inhibition of human monoamine oxidases (MAO) and antioxidant properties. The aqueous extracts prepared from different parts of the plant collected from different geographical locations and seasons were analyzed by HPLC for principal bioactive markers. The extracts were simultaneously tested
in vitro for inhibition of human MAOs and antioxidant activity for analysis of correlation between phytochemical composition of the extracts and bioactivities.
Reversed-phase HPLC with photodiode array detection was employed to profile the alkaloidal and non-alkaloidal components of the aqueous extract of
Banisteriopsis caapi. The
Banisteriopsis caapi extracts and standardized compositions were tested
in vitro for inhibition of recombinant preparations of human MAO-A and MAO-B.
In vitro cell-based assays were employed for evaluation of antioxidant property and mammalian cell cytotoxicity of these preparations.
Among the different aerial parts, leaves, stems/large branches and stem bark of
Banisteriopsis caapi, HPLC analysis revealed that most of the dominant chemical and bioactive markers (1, 2, 5, 7–9) were present in high concentrations in dried bark of large branch. A library of HPLC chromatograms has also been generated as a tool for fingerprinting and authentication of the studied
Banisteriopsis caapi species. The correlation between potency of MAO inhibition and antioxidant activity with the content of the main active constituents of the aqueous
Banisteriopsis caapi extracts and standardized compositions was established. Phytochemical analysis of regular/commercial
Banisteriopsis caapi dried stems, obtained from different sources, showed a similar qualitative HPLC profile, but relatively low content of dominant markers 1, 2, 7, and 9, which led to decreased MAO inhibitory and antioxidant potency compared to
Banisteriopsis caapi Da Vine.
The ethnopharmacological use of bark of matured stem/large branch of
Banisteriopsis caapi as well as whole matured stem is supported by the results obtained in this investigation. Among various constituents of
Banisteriopsis caapi, harmine (7), harmaline (6) and tetrahydroharmine (5) are responsible for MAO-A inhibition, while two major proanthocyanidines, epicatechin (8) and procyanidine B2 (9) produce antioxidant effects. The compounds 1–9 can serve as reliable markers for identification and standardization of
Banisteriopsis caapi aerial parts, collected in different seasons and/or from different geographical regions.
Hoodia gordonii, a succulent plant growing in African arid regions, is used as a botanical dietary supplement for weight loss. The increasing concerns on the quality and safety of Hoodia products ...call for the needs of more science-based information, as well as objective and efficient tools for inspection. In the present study, NMR fingerprinting and multivariate analysis techniques were applied for the identification, discrimination, and quality analysis of Hoodia plant materials and commercial products. Four Hoodia species, namely H. gordonii (five authenticated samples), H. currorii (one authenticated sample), H. parviflora (three authenticated samples), and H. rushii (one authenticated sample), were investigated; the chemicals and characteristic spectral signals that made most contributions for their differentiations were revealed. With the aid of NMR fingerprint analysis, ten Hoodia products sold on the dietary supplement market were assessed for their chemical composition and quality. The study demonstrated that the NMR fingerprinting approach could be a promising and efficient tool for the authentication of botanicals.
A new potent antiinfective and antiparasitic 2,3-dihydro-1H-indolizinium chloride (1) was isolated from Prosopis glandulosa var. glandulosa. Three additional new (2−4) and one known (5) indolizidines ...were also isolated, and the dihydrochloride salts of 1−3 (compounds 6, 7, and 8) were prepared. Structures were determined by 1D and 2D NMR and mass spectra. Compound 1 showed potent in vitro antifungal activity against Cryptococcus neoformans and Aspergillus fumigatus (IC50 values = 0.4 and 3.0 μg/mL, respectively) and antibacterial activity against methicillin-resistant Staphylococcus aureus and Mycobacterium intracellulare (IC50 values of 0.35 and 0.9 μg/mL, respectively). The remarkable in vitro fungicidal activity of 1−4 against C. neoformans (MFCs = 0.63−1.25 μg/mL) and 2, 3, and 5 against A. fumigatus (MFCs = 0.63−2.5 μg/mL) were similar to amphotericin B, but >2−4-fold more potent than 6−8. Prosopilosidine (1) showed potent in vivo activity at 0.0625 mg/kg/day/ip for 5 days in a murine model of cryptococcosis by eliminating ∼76% of C. neoformans infection from brain tissue compared to ∼83% with amphotericin B at 1.5 mg/kg/day. Compounds 1 and 4 exhibited potent activity and high selectivity index (SI) values against chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum, with IC50 values of 39 and 95 ng/mL and 42 and 120 ng/mL, respectively (chloroquine, IC50 = 17 and 140 ng/mL). Prosopilosine (1) also showed in vivo antimalarial activity, with an ED50 value of ∼2 mg/kg/day/ip against Plasmodium berghei-infected mice after 3 days of treatment.
24(
R)-Ethylcholest-6-ene-5α-ol-3-
O-β-
d-glucopyranoside (
1), along with 11 known compounds (
2–
12) including aporphine alkaloids, diterpenes, a steroid glycoside and a flavonoid glycoside were ...isolated from the leaves of
Nelumbo nucifera and evaluated for their antifungal, antimalarial and for cytotoxic activities. Antifungal activity was observed for (
R)-roemerine (
3) and antimalarial activity for (
R)-roemerine (
3) and
N-methylasimilobine (
5). Position C-1 and C-2 of aporphine alkaloids is crucial for antimalarial activity.
▪
From the leaves of
Nelumbo nucifera (an aquatic plant), one new compound, 24(
R)-ethylcholest-6-ene-5α-ol-3-
O-β-
d-glucopyranoside (
1), along with 11 known metabolites (
2–
12), were isolated and identified by spectroscopic methods including 1D- and 2D NMR. Antifungal activity for (
R)-roemerine (
3) (IC
50/MIC
=
4.5/10
μg/mL against
Candida albicans) and antimalarial activity for (
R)-roemerine (
3) and
N-methylasimilobine (
5) (IC
50
=
0.2 and 4.8
μg/mL for the D6 clone, respectively, and 0.4 and 4.8
μg/mL for the W2 clone, respectively) was observed. None of the compounds were cytotoxic to Vero cells up to a concentration of 23.8
μg/mL. NMR data for 10-eicosanol (
7) and 7,11,15-trimethyl-2-hexadecanone (
10) are presented for the first time. An analysis of the structure–activity relationship shows that the substituents in position C-1 and C-2 of aporphine alkaloids are crucial for the antimalarial activity.
Stephania tetrandra
S. Moore (Hang Fang Ji) is used in traditional Chinese medicine as a diuretic, an antiphlogistic, and an antirheumatic. The name “fang ji” is applied to at least four different ...genera of plants, including
Aristolochia fangchi
Y. C. Wu ex L. D. Chow and S. M. Hwang,
Cocculus orbiculatus
(L.) DC.,
Stephania tetrandra
S. Moore, and
Sinomenium acutum
Rehder and E. H. Wilson. Due to similarity in the use of their common names,
Stephania tetrandra
S. Moore is often confused with
Aristolochia fangchi
Y. C. Wu ex L. D. Chow and S. M. Hwang, which has potentially dangerous consequences. To aid rapid and easy differentiation between the roots of these four species, so as to avoid possible contamination, detailed macroscopic and microscopic observations were made using stereo-and light-microscopy. The powdered samples were further analyzed using HPLC.
Aim To carry out (1) a floristic survey of endemic flowering plants of the Western Ghats occurring in Goa, (2) identify their habitat preference and diversity of life-form type, (3) observe flowering ...phenology of the endemics and (4) to correlate factors that affect their phenological pattern. Location Goa state is located between 15°48' N and 14°53'54'' N and 74°20'13'' E and 73°40'33'' E, in the northern part of the Western Ghats, India. Method A list of endemic plants from the study area was prepared using available floristic works and checklists of endemic plants of India. Based on preliminary field observations carried out in the study area, major habitats such as plateaus, moist deciduous forests, semi-evergreen forests, evergreen forests and mangroves were identified for the subsequent intensive survey of endemics. Voucher specimens for all the endemic species were collected, processed using conventional herbarium techniques and deposited in the Herbarium, Department of Botany, Goa University. Species were identified using local and regional floras and their identity was confirmed at various herbaria along the Western Ghats. Data on their life-form types, habitat and phenology was recorded in the field. Phenological observations were made every fortnight. A computerized data base was generated incorporating details on their life-form type, phenology and habitat. Results A floristic survey of endemic plants of the Western Ghats in Goa resulted in the collection of 113 endemic species. Life-form analysis reveals that herbaceous endemics are the most dominant followed by trees, shrubs and climbers. Plateaus in the study area harbour the largest number of endemic species, especially herbs. Endemic trees are distributed in the semi-evergreen and evergreen forests. Endemic species in the study area show different peak and lean seasons of flowering depending on their life-form type, habitat and ecological factors like temperature and rainfall/moisture content in the soil. Main conclusions The plateaus in the northern part of the Western Ghats are unique, being species rich with herbaceous endemics. These ephemerals are closely associated with the rainfall patterns thus; any change of moisture regime over the long-term will have an impact on the distribution of these endemics.
A high-performance liquid chromatographic (HPLC) method with ultraviolet absorption detection was developed to determine the presence of anthraquinones, polydatin, and resveratrol in Polygonum ...multiflorum Thunb. as well as other medicinal Polygonum species, viz., P. cuspidatum, P. oriental, P. aviculare, and P. vulgare, as well as commercial products that claim to contain P. multiflorum. The best results were obtained with a Phenomenex Gemini C18 column using gradient mobile phase composed of water (0.1% acetic acid) and acetonitrile (0.1% acetic acid). Elution was at a flow rate of 1.0 mL/min. The detection wavelength was 280 nm for anthraquinones and 320 nm for polydatin and resveratrol. The main anthraquinones identified were emodin and physcion. The HPLC pattern of P. multiflorum was also compared with 5 other species of Polygonum. The method was validated for precision, repeatability, and accuracy. The relative standard deviation was between 0.9 and 1.6%. The method was sensitive, quick, and accurate for determination of anthraquinones, polydatin, and resveratrol in 6 different species of Polygonum and can be used for quality control of P. multiflorum. The commercial samples and the 6 Polygonum species were compared microscopically, and a detailed description is provided for P. multiflorum.
Ephedra sinica Stapf or Ma Huang has been used in traditional Chinese medicine for over 5000 years as a bronchodilating and stimulatory agent. In the West, it is popularly used in dietary supplements ...for weight loss and to enhance athletic performance. Adverse events have been reported following consumption of dietary supplements containing ephedrine alkaloids. There are about 50 known species of Ephedra. The ratio of ephedrine to other alkaloids varies from species to species; all North American species lack alkaloids. The method commonly used in the dietary supplement industry for botanical authentication is to analyze the product for the presence of chemical markers known to be present in the specific herb. However, this method does not ensure that the product contains authentic herb, especially if it has been spiked with chemical marker compounds. In the trade and raw drug market, Ephedra is available in the form of stem cuttings or powders, without any vouchers, thus making identification of the species difficult. Using light microscopy, we can detect the presence of Ephedra herb, even in powder form, and identify within certain limits its geographical origin. Identification of Chinese and North American species of Ephedra has been made easier by developing a key using leaf and internode length as key identification characters.
This article outlines the development of a simple and specific analytical method for the quantitative determination of eight coumarin constituents from the methanolic extract of the roots of Angelica ...gigas. The coumarin constituents present in the roots of Angelica gigas were separated using an acetonitrile (0.1 % acetic acid)-water (0.1 % acetic acid)-reagent alcohol gradient solvent system at a flow rate of 1.0 mL per minute. The HPLC separation was performed using a Phenomenex C12 reversed phase column with detection at 328 nm. The method was successfully used to study the percentage compositions of eight coumarins present in various Angelica species procured from S. Korea. Additionally, this manuscript provides a detailed microscopic account for the authentication of Angelica gigas and compared it with other Angelica species. The microscopic evaluation of plant tissue samples plays a vital role in botanical authentication. The combination of these two methodologies will provide additional tools for the evaluation of various Angelica species.
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