Flueggea Virosa Research Articles

High-performance thin-layer chromatography based concurrent estimation of biomarkers ent-phyllanthidine and rutin in the dried aerial parts of Flueggea virosa

The biomarkers are needed to be defined for standardization purposes so that safe and effective herbal formulations can be catered to the society. There is an urgent need for statistical support of herbal drugs because most of the herbal products are still used in the non-standardized form. This study is based on the development of a simple and sensitive RP-HPTLC method for concurrent estimation of two biomarkers ent-phyllanthidine and rutin in the methanol extract of aerial parts of Flueggea virosa. The developed method was found to be simple, economic and sensitive. Separation and quantification were performed with acetonitrile: water (4:6V/V) used as the mobile phase on glass-backed RP-HPTLC plate. Detection of absorption maxima and quantification was done at 310nm of UV region. The developed chromatographic system was found to give a sharp band for ent-phyllanthidine and rutin at Rf 0.73±0.01 and 0.68±0.01, respectively. The linearity ranges for ent-phyllanthidine, and rutin were found to be 200–1600ngband−1 and 100–1400ngband−1, respectively, with correlation coefficients (r2 values) of 0.998 and 0.997, respectively. The percentage of ent-phyllanthidine and rutin was found to be 9.121±0.02% and 1.018±0.04% (w/w), respectively. The resolution of bands and separation of constituents in FVME exhibited the perfect optimization of the developed method. The validation statistics supports the proposed method for standardizing crude drugs as well as formulations of a natural product containing ent-phyllanthidine and rutin.

Chemical Constituents from Flueggea virosa and the Structural Revision of Dehydrochebulic Acid Trimethyl Ester.

In an attempt to study the chemical constituents from the twigs and leaves of Flueggea virosa, a new terpenoid, 9(10→20)-abeo-ent-podocarpane, 3β,10α-dihydroxy-12-methoxy-13- methyl-9(10→20)-abeo-ent-podocarpa-6,8,11,13-tetraene (1), as well as five known compounds were characterized. Their structures were elucidated on the basis of spectroscopic analysis. In addition, the structure of dehydrochebulic acid trimethyl ester was revised as (2S,3R)-4E-dehydrochebulic acid trimethyl ester based on a single-crystal X-ray diffraction study. The in vitro anti-hepatitis C virus (anti-HCV) activity and cytotoxicity against Huh7.5 cells for the isolated compounds were evaluated.

ChemInform Abstract: 13‐Methyl‐3,4‐seco‐ent‐podocarpanes, Rare C18‐Diterpenoids from the Roots of Flueggea virosa.

Abstract[14 compounds]

Norsecurinamines A and B, two norsecurinine-derived alkaloid dimers from the fruits of Flueggea virosa

The phytochemical investigation on the fruits of Flueggea virosa resulted in the discovery of two new norsecurinine-derived alkaloid dimers, norsecurinamines A and B (1 and 2). Compound 1 is the first hetero-dimeric alkaloid possessing norsecurinine and donaxaridine units, and 2 represents the first example of NH-linked dimeric Securinega alkaloid. Their structures and absolute configuration were elucidated on the basis of extensive spectroscopic analysis as well as single-crystal X-ray diffraction method. A plausible biogenetic pathway of 1 was also proposed.

ChemInform Abstract: Flueggethers B—D, Securinega Alkaloids with Rare Oligomerizing Pattern from Flueggea virosa.

Three new Securinega alkaloids, flueggethers B and C (1 and 2) as dimers and flueggether D (3) as a trimer, were isolated from the twigs and leaves of a Chinese herb, Flueggea virosa. Their structures were characterized by spectroscopic means and NMR comparison with known analogues. Among all Securinega alkaloid oligomers reported to date, alkaloids 1 and 2 are rare examples linked via an ether bond, while 3 represents the first member with a mixed oligomerizing pattern incorporating both oxygen bridge and carbon–carbon linkage. An in vitro anti-HIV bioassay revealed moderate activity for 3.

Terpenoids from Flueggea virosa and their anti-hepatitis C virus activity

Phytochemical study of the methanolic root extract of Flueggea virosa allowed for the characterization of 18 non-alkaloid terpenoids. Their structures have skeletons composed of six rearranged ent-podocarpanes, 11 ent-podocarpanes, and a 3,4-seco-30-nor-friedelane. These were characterized based on 2D NMR, IR, UV, and MS spectroscopic analysis and their absolute configurations were determined by single-crystal X-ray studies, as well as by 1H NMR spectroscopic analysis for the corresponding chiral derivatives. The isolates were evaluated for therapeutic potential against hepatitis C virus (HCV) infection to human hepatoma Huh7.5 cells.

ChemInform Abstract: New Securinega Alkaloids with anti‐HIV Activity from Flueggea virosa.

AbstractNine novel Securinega alkaloids are isolated including flueggenines as monomers (I) and dimers (II), and new trimers such as (III), named fluevirosines.

Flueggethers B–D, Securinega alkaloids with rare oligomerizing pattern from Flueggea virosa

Three new Securinega alkaloids, flueggethers B and C (1 and 2) as dimers and flueggether D (3) as a trimer, were isolated from the twigs and leaves of a Chinese herb, Flueggea virosa. Their structures were characterized by spectroscopic means and NMR comparison with known analogues. Among all Securinega alkaloid oligomers reported to date, alkaloids 1 and 2 are rare examples linked via an ether bond, while 3 represents the first member with a mixed oligomerizing pattern incorporating both oxygen bridge and carbon–carbon linkage. An in vitro anti-HIV bioassay revealed moderate activity for 3.

13-Methyl-3,4-seco-ent-podocarpanes, rare C18-diterpenoids from the roots of Flueggea virosa

13-Methyl-3,4-seco-ent-podocarpanes from F. virosa were characterized. Their structures were elucidated by extensive spectroscopic analysis. Compound 8 exhibited significant anti-HCV activity with a therapeutic index of 100.5.

Flueggether A and Virosinine A, Anti-HIV Alkaloids from Flueggea virosa.

Two new alkaloids, flueggether A (1) and virosinine A (2), were isolated from a Chinese medicinal plant, Flueggea virosa. Their structures were assigned via spectroscopic methods with the absolute configurations of 1 and 2 being established by X-ray diffraction analysis and calculated electronic circular dichroism data, respectively. Compound 1 represents the first example with an ether bridge of Securinega alkaloid oligomers, and 2 bears a new heterocyclic backbone. Both alkaloids showed mild in vitro anti-HIV activity.

Antiplasmodial potential of traditional antimalarial phytotherapy remedies used by the Kwale community of the Kenyan Coast

Ethnopharmacological relevanceIn Kenya, 22 million people are at risk of malaria, 70% of them are in rural areas and most of these people use traditional plant based medicines to treat malaria. The aim of the study was to escalate documentation, from an earlier study of medicinal plants, traditionally used to treat malaria by the Digo community of Kwale County, taking cognizance of their pharmacological information by evaluating their antiplasmodial efficacies. Materials and methodsThe study was carried out in Kwale County at Shimba Hills Game Reserve and adjoining part of Kinango. Traditional health practitioners (THP) were interviewed with a standard questionnaire to obtain information on medicinal plants traditionally used for management of malaria. Group interviews were also held among THPs and members of the community. The plant samples collected were tested for antiplasmodial activity against chloroquine sensitive (D6) and resistant (W2) Plasmodium falciparum using the ability of extracts, prepared from the plant species, to inhibit the incorporation of [G-3H] hypoxanthine into the malaria parasites. ResultsFifty seven (57) species in forty eight (48) genera and thirty (30) families were documented and evaluated for in vitro antiplasmodial activity. Apocynaceae, Euphorbiaceae, and Rubiaceae families had each about 12% of the plant species reported as antimalarial remedy and represented the species that are most commonly used. Twelve species (21.1%) showed antiplasmodial efficacy of IC50<5µg/ml and these were Boscia salicifolia, Cissampelos mucronata, Clerodendrum myricoides, Commiphora schimperi, Flueggea virosa, Maytenus undata, Maytenus senegalensis, Maytenus putterlickioides, Vernonia amygdalina, Warburgia stuhlmannii, Zanthoxylum chalybeum and Tabernaemontana pachysiphon. ConclusionsThese results seem to indicate that ethnopharmacological inquiry used in search for new herbal remedies as predictive and could form the basis of an ethnopharmacopoeia and search for new active principles. This is the first report on traditional use of T. pachysiphon for malaria and its antiplasmodial activity.

Simultaneous quantification of biomarkers bergenin and menisdaurin in the methanol extract of aerial parts of Flueggea virosa by validated HPTLC densitometric method.

A simple, sensitive high-performance thin-layer chromatography (HPTLC) method was developed for the simultaneous quantification of biomarker bergenin and menisdaurin in the methanol extracts of aerial parts of Flueggea virosa (FVME). Chromatography was performed on glass-backed silica gel 60F254 HPTLC plates using dichloromethane: methanol as mobile phase. Scanning and quantification was done at UV absorption maxima of 260 nm. The system was found to give compact spot for bergenin and menisdaurin at Rf = 0.29 ± 0.01 and 0.16 ± 0.01, respectively. The linearity ranges for bergenin and menisdaurin were found to be the same (100-800 ng/spot) with correlation coefficients (R(2) values) of 0.997 and 0.999, respectively. The limit of detection for bergenin and menisdaurin was found to be 27 and 36.2 ng/band, respectively, while the limit of quantification was found to be 81 and 108 ng/band, respectively. Intra- and interday precisions (n = 6) for bergenin and menisdaurin were found to be 1.41-1.71 and 1.65-1.87%, and 1.68-1.89 and 1.75-1.93%, respectively. The percent recoveries were found to be 98.7-99.4 and 99.5-99.9%, respectively, for bergenin and menisdaurin. The percentage of bergenin and menisdaurin was found to be 15.25 and 4.22% (w/w), respectively, in FVME. The developed method permitted the simultaneous quantification of bergenin and menisdaurin and showed good resolution and separation from other constituents of extract; hence, the method can be used to standardize herbal formulations as well as bulk drugs for bergenin and menisdaurin.

A stability-indicating assay of biomarker bergenin in the aerial parts ofFlueggea virosaby a validated high-performance thin-layer chromatographic-densitometric method

A simple, sensitive, and stability-indicating thin-layer chromatographic (TLC)-densitometric method was developed for the assay of biomarker bergenin in the methanol extract of aerial parts of Flueggea virosa (FVME). Chromatography was performed on glass-backed silica gel 60 F254 high-performance thin-layer chromatographic (HPTLC) plates with dichloromethane-methanol (8.5:1.5, v/v) as the mobile phase. Scanning and quantification were done at 220 nm. The system was found to give compact spot for bergenin at RF = 0.29 ± 0.01. The linear regression analysis data for the calibration plots showed good linear relationship with r2 = 0.998 with respect to area in the concentration range of 100–800 ng. The regression equation of bergenin was found to be Y = 8.708X + 51.017. The limit of detection (LOD) and limit of quantification (LOQ) for bergenin were found to be 17.5 and 53 ng band−1, respectively. The percentage of bergenin was found to be 15.5% w/w in the FVME. Bergenin was subjected to acid and alkali hydro...

New Securinega alkaloids with anti-HIV activity from Flueggea virosa

A series of Securinega alkaloid hybrids and oligomers with anti-HIV activity were isolated and identified from Flueggea virosa.

Chemical and Biological Study of Flueggea virosa Native to Saudi Arabia

Flueggea virosa (Roxb. ex Willd.) Royle (Phyllanthaceae), also known as Chinese waterberry, is a shrub up to 4 m high growing wild in tropical Africa, Middle East, tropical Asia, Japan, Australia, and Polynesia and can also be grown domestically. It has many recorded uses in Chinese herbal medicine. The plant has been used for the treatment of fever, malaria, sexual dysfunction, pain, diabetes, epilepsy, snakebite, venereal disease, rheumatism, arrhythmia, rash, diarrhea, pneumonia, cough, hepatitis, and HIV-related illness, and as a contraceptive [1, 2]. The methanol and water extracts of the plant have been reported to possess a number of biological activities such as antiplasmodial, trypanocidal, and antiarrhythmic [3, 4]. Previous phytochemical studies of F. virosa showed the presence of triterpenoids [2], tannins, flavonoids, saponins [5, 7], resins, glycosides, glycerin carbohydrates, anthraquines, steroids [5], alkaloids [6, 8], cardiac glycosides [5, 6], and anthraquinones [6]. In our phytochemical investigation of this plant [9], a total of 14 compounds were isolated from the ethanolic extract of the aerial parts of F. virosa, collected from the Southern part of Saudi Arabia, in June 2000. The plant (air-dried crushed aerial parts, 1 kg) was macerated with 95% EtOH at room temperature overnight (1 L each 3). The dried crude EtOH extract (40 g) was dissolved in 0.1 N HCl (1 L; pH 1) and partitioned with n-hexane and n-BuOH (500 mL 3) successively. The n-BuOH fraction was subjected to flash column chromatography (CC) over silica gel to afford bergenin [white crystals, mp 236–238 C (1, 10 g)], menisdaurin [brown solid, mp 172–173 C (2, 1 g)] and amiroside [brown solid, mp 176–178 C (3, 25 mg)] [9, 10]. The defatted aqueous acidic fraction was basified with NH4OH (pH 11) and partitioned with EtOAc. The EtOAc fraction (3 g) was subjected to flash chromatography on silica gel with further purification using reverse phase CC over C-18 silica gel (MeCN–H2O, 9:1) to afford ent-phyllanthidine [yellow white crystals, mp 158–160 C (4, 30 mg)] [11], securinine [white powder, mp 140–142 C (5, 8 mg)], securinol [white powder, mp 136–137 C (6, 6 mg)], viroallosecurinine [dark yellow solid, mp 130–132 C (7, 40 mg)] [12], flavonoid rutin [yellow solid, mp 194–195 C (8, 40 mg)] [13], gallocatechin (9) and epi-gallocatechin [white solid, mp 188–190 C] (10, mixture, 12 mg) [14], 2,2 ,5,5 -tetrahydroxybiphenyl [white solid, mp 144–145 C (11, 12 mg)], ethylmanopyranoside [white solid, mp 154–156 C (12, 132 mg)], ethyl glucopyranoside [white powder, mp 163–164 C (13, 9 mg)] [9], and the triterpene precursor squalene [oil (14, 20 mg)] [15]. The identity of all the isolated compounds was confirmed by direct comparison with authentic samples, as well as their physical and spectral data (UV, IR, NMR and MS) with those published in the literature. This is the first report of the cyanogenetic glucosides menisdaurin (2) and amiroside (3) isolated from the genus Flueggea, as well as from the plant family Phyllanthaceae. They were previously reported from Ilex aquifolium and Guazuma ulmifolia [16].

Effect of air pollution on the foliar morphology of some species in the family Euphorbiaceae in southwestern Nigeria

Morphological studies of the leaves of ten species in the family Euphorbiaceae collected from three different locations with different pollution levels in Southwestern Nigeria were carried out in order to establish the effect of air pollution on these species. The study was carried out in both dry and wet seasons. Climatic data and pollutants concentration levels of the study sites were determined. Leaf area of all the species was measured using an established nondestructive method while petiole length was determined using metric ruler. The result showed that most species showed significant reductions (p&lt;0.05) in the leaf area and petiole length across the three locations and this reduction is from rural to sub-urban to urban areas. Among all the species that showed reductions in leaf area, Alchornea cordifolia showed the highest response while Euphorbia hyssopifolia, E. hirta and Croton lobatus do not show clear reductions. Similar significant reductions were recorded for petiole length with the highest impact recorded in Manihot esculenta while species like E. hyssopifolia, E. hirta, C. lobatus and Flueggea virosa were not significantly reduced. This study showed that plants generally respond to air pollution with reduction in foliar morphology and the response is species specific.Keywords: Pollution, leaf morphology, Euphorbiaceae, leaf area, petiole length

Anti-HIV Securinega alkaloid oligomers from Flueggea virosa

An MS guided fractionation of the alkaloidal constituents of Flueggea virosa has yielded nine new Securinega alkaloid oligomers, fluevirosinines B–J (1–9). The absolute structures of these oligomers have been characterized on the basis of spectroscopic data and biogenetic consideration. Fluevirosinines B–E (1–4) are four tetramers with new connecting sequences or new oligomerizing patterns, and fluevirosinines G–J (6–9) represent the first examples of pentamers of the Securinega alkaloid family. Among these alkaloids, fluevirosinine B (1) showed the best anti-HIV activity with an EC50 value of 14.1±1.2 μM.

Fluevirines A–D, four new securinega-type alkaloids from Flueggea virosa

Four new securinega-type alkaloids, fluevirines A–D (1–4), along with ten known ones, were isolated from the twigs and leaves of Flueggea virosa. The structures of the new ones were elucidated by means of spectroscopic methods, and their absolute configurations were assigned by CD spectra. Among them, fluevirine A (1) was a novel C,C-linked dimeric indolizidine alkaloid and showed weak antimicrobial activity against Staphylococcus aureus.

First report of Masseeëlla capparis in Australia

The rust fungus Masseeëlla capparis is reported for the first time in Australia on Flueggea virosa (Phyllanthaceae). This is the first species of Masseeëlla found in Australia. The rust is described and illustrated from Australian specimens. A discussion on species of Masseeëlla is provided. A reconstructed phylogeny with the Large Subunit region of ribosomal DNA indicated that Masseeëlla has an affinity with the Phakopsoraceae.

Anti-Hepatitis C Virus Dinorditerpenes from the Roots of Flueggea virosa

Along with four known terpenoids (1-4), eight new dinorditerpenes (5-12) were isolated and identified from the roots of Flueggea virosa. The absolute configurations of 4-6 were determined by the Mosher's method, and that of 5 was confirmed by single-crystal X-ray diffraction analysis. Using the hepatitis C virus cell culture infection system, compounds 1, 3, 11, and 12 exhibited significant anti-HCV activity with EC50 values of 5.6, 5.0, 7.5, and 6.6 μM, respectively. Compounds 11 and 12 were nontoxic toward the tested Huh7.5 cell lines.