Furanoflavonoid glycosides from Pongamia pinnata fruits

Pongamia pinnata fruits afforded three new furanoflavonoid glucosides, pongamosides A-C (1-3), and a new flavonol glucoside, pongamoside D (4). The structures of these compounds were established on the basis of spectroscopic studies. This is the first time that furanoflavone glucosides have been found as naturally occurring compounds.     

Pongamone A-E, five flavonoids from the stems of a mangrove plant, Pongamia pinnata

Chemical investigation of stems of the mangrove plant, Pongamia pinnata, resulted in isolation and characterization of five structurally unusual flavonoids pongamones A-E, along with 16 known flavonoid metabolites. Their structures were determined on the basis of spectroscopic analyses and by comparison of their spectroscopic data with those of related compounds reported in the literature. Pongamones A-E were assayed against DHBV RCs DNAP and HIV-1 RT in vitro. A possible biogenetic pathway of the isolated compounds is also proposed.     

Microwave assisted alkali-catalyzed transesterification of Pongamia pinnata seed oil for biodiesel production

In this study, microwave assisted transesterification of Pongamia pinnata seed oil was carried out for the production of biodiesel. The experiments were carried out using methanol and two alkali catalysts i.e., sodium hydroxide (NaOH) and potassium hydroxide (KOH). The experiments were carried out at 6:1 alcohol/oil molar ratio and 60 °C reaction temperature. The effect of catalyst concentration and reaction time on the yield and quality of biodiesel was studied. The result of the study suggested that 0.5% sodium hydroxide and 1.0% potassium hydroxide catalyst concentration were optimum for biodiesel production from P. pinnata oil under microwave heating. There was a significant reduction in reaction time for microwave induced transesterification as compared to conventional heating.     

In Vitro Screening of Anti-lice Activity of Pongamia pinnata Leaves

Growing patterns of pediculocidal drug resistance towards head louse laid the foundation for research in exploring novel anti-lice agents from medicinal plants. In the present study, various extracts of Pongamia pinnata leaves were tested against the head louse Pediculus humanus capitis. A filter paper diffusion method was conducted for determining the potential pediculocidal and ovicidal activity of chloroform, petroleum ether, methanol, and water extracts of P. pinnata leaves. The findings revealed that petroleum ether extracts possess excellent anti-lice activity with values ranging between 50.3% and 100% where as chloroform and methanol extracts showed moderate pediculocidal effects. The chloroform and methanol extracts were also successful in inhibiting nymph emergence and the petroleum ether extract was the most effective with a complete inhibition of emergence. Water extract was devoid of both pediculocidal and ovicidal activities. All the results were well comparable with benzoyl benzoate (25% w/v). These results showed the prospect of using P. pinnata leave extracts against P. humanus capitis in difficult situations of emergence of resistance to synthetic anti-lice agents.     

Iridoids from Kigelia pinnata DC. fruits

From the fruits of Kigelia pinnata DC., a new furanone derivative formulated as 3-(2'-hydroxyethyl)-5-(2"-hydroxypropyl)-dihydrofuran-2(3H)-one (1), and four new iridoids named; 7-hydroxy viteoid II (2), 7-hydroxy eucommic acid (3), 7-hydroxy-10-deoxyeucommiol (4) and 10-deoxyeucommiol (5) have been isolated together with seven known iridoids, jiofuran (6), jioglutolide (7), 1-dehydroxy-3,4-dihydroaucubigenin (8), des-p-hydroxybenzoyl kisasagenol B (9), ajugol (10), verminoside (11) and 6-trans-caffeoyl ajugol (12). The structures of the isolated compounds were characterized by different spectroscopic methods.     

Macrocyclic diarylheptanoids from Garuga pinnata

Three macrocyclic diarylheptanoids, 6'-hydroxygaruganin V (1), 9'-desmethylgarugamblin I (2) and 1,9'-didesmethylgaruganin III (3) were isolated from the petroleum ether and dichloromethane extracts of the stem bark of Garuga pinnata. The structures of these compounds were established by extensive spectroscopic studies, including high field NMR and MS measurements.     

Antimycobacterial flavonoids from Derris indica

Flavonoids (1-4), together with ten known compounds (5-14) were isolated from the stems and roots of the mangrove plant Derris indica. Their chemical structures were elucidated by analysis of their spectroscopic data. All compounds except compounds 2 and 6 exhibited antimycobacterial activity with minimum inhibitory concentrations (MIC) between 6.25 and 200 microg/mL.     

Efficacy of karanjin and phorbol ester fraction against termites (Odontotermes obesus)

The non-edible oil seeds of Jatropha curcas (physic nut) and Pongamia pinnata (karanja) contain some toxic components (phorbol esters in J. curcas and karanjin in P. pinnata), which may be used as biopesticides. In this study, the active components of J. curcas and P. pinnata oil were extracted and their efficacy against the termites Odontotermes obesus (Rambur), was tested. The phorbol ester fraction of J. curcas and karanjin of P. pinnata oil were found to be effective against termites. A mortality rate of 100% was achieved in 6 h with karanjin and in 12 h with phorbol ester fraction. The LC₅₀ levels of karanjin and phorbol esters fractions were 0.038 and 0.071 g ml⁻¹, respectively, after 24 h at a 95% (0.05) confidence limit.     

Seed abortion in Pongamia pinnata (Fabaceae)

In Pongamia pinnata only one of the two ovules develops into a seed in most of the pods. Since pollen was not found to be limiting and reduced fertilization could not completely explain the observed frequency of seed abortion, it implied an effect of postfertilization factors. Aqueous extracts of developing seeds and maternal tissue (placenta) did not influence abortion in vitro, suggesting that abortion may not be mediated by a chemical. Experimental uptake of ¹⁴C sucrose in vitro indicated that both the stigmatic and the peduncular seed have similar inherent capacities of drawing resources, but the peduncular seed is deprived of resources in the presence of the stigmatic seed. This deprivation of the peduncular seed could be offset by supplying an excess of hormones leading to the subsequent formation of two seeds in a pod. The prevalence of single-seeded pods in P. pinnata seems therefore to be a result of competition between the two seeds for maternal resources. The evolutionary significance of single-seeded pods in P. pinnata is discussed with respect to possible dispersal advantage enjoyed by such pods.     

Pongamia pinnata influences the circadian variations of liver marker enzymes in hyperammonemic rats

In this study, the influences of Pongamia pinnata, an indigenous medicinal plant used in Ayurvedic and traditional Medicine in India, on the circadian variations of liver marker enzymes in ammonium chloride (AC) induced hyperammonemic rats were studied. Experimental rats (160 - 180 g) were divided into control, AC (daily i.p. injection of AC (100 mg kg^-1 body weight)) treated, AC + P. pinnata ethanolic leaf extract (PPEt) (300 mg kg^-1 body weight) treated and PPEt treated groups. Temporal characteristics (acrophase, amplitude and mesor) of liver marker enzymes; alkaline phosphatase (ALP), aspartate and alanine transaminases (ALT and AST) and γ-glutamyl transferase (GGT) were analyzed. Elevated liver marker enzymes (increased mesor and delayed acrophase of AST, ALT, ALP and GGT) were found in hyperammonemic rats. Administration of PPEt significantly alters these changes. Variations in acrophase, amplitude and r values were also found in control and experimental rats. The detectable circadian rhythms of hepatic marker enzymes and their alterations during AC/PPEt treatments, in the present study, deserve further investigation for the diagnosis and for the therapeutic efficacy of hyperammonemia.     

The antileishmanial activity assessment of unusual flavonoids from Kalanchoe pinnata

The importance of flavonoids for the antileishmanial activity of Kalanchoe pinnata was previously demonstrated by the isolation of quercitrin, a potent antileishmanial flavonoid. In the present study, the aqueous leaf extract from the medicinal plant K. pinnata (Crassulaceae) afforded a kaempferol di-glycoside, named kapinnatoside, identified as kaempferol 3-O-alpha-L-arabinopyranosyl (1-->2) alpha-L-rhamnopyranoside (1). In addition, two unusual flavonol and flavone glycosides already reported, quercetin 3-O-alpha-L-arabinopyranosyl (1-->2) alpha-L-rhamnopyranoside (2) and 4',5-dihydroxy-3',8-dimethoxyflavone 7-O-beta-D-glucopyranoside (3), have been isolated. Their structures were determined via analyses of mono and bi-dimensional (1)H and (13)C NMR spectroscopic experiments and HR-MALDI mass spectra. Because of its restricted occurrence and its abundance in K. pinnata, flavonoid (2) may be a chemical marker for this plant species of high therapeutic potential. The three flavonoids were tested separately against Leishmania amazonenis amastigotes in comparison with quercitrin, quercetin and afzelin. The quercetin aglycone - type structure, as well as a rhamnosyl unit linked at C-3, seem to be important for antileishmanial activity.     

Cytotoxic triterpenoid saponins acylated with monoterpenic acids from fruits of Gleditsia caspica Desf.

Four bisdesmosidic triterpenoid saponins named caspicaosides A-D, were isolated from the fruits of Gleditsia caspica Desf. Their structures were determined by NMR spectroscopy including HOHAHA, ¹H-¹H COSY, ROE, HMQC, HMBC experiments and HRFAB-MS as well as acid hydrolysis. The four 3,28-O-bisdesmosidic triterpenoid saponins comprised echinocystic acid as the aglycone and common oligosaccharide moieties at C3 and C28. The saccharide moiety at C-3 was identified as β-d-xylopyranosyl-(1 → 2)-α-l-arabinopyranosyl-(1 → 6)-β-d-glucopyranosyl while that at C-28 was determined as β-d-xylopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-[α-l-rhamnopyranosyl-(1 → 6)-]β-d-glucopyranosyl. The pentasaccharide moiety linked to C-28 was acylated with monoterpenic acid and or monoterpene-arabinoside moieties at C-2 or C-2 and C-3 of the terminal rhamnose unit. The isolated saponins were assayed for their in vitro cytotoxicities against the three human tumor cell lines HepG2, A549 and HT29 using MTT method. The results showed that caspicaosides B and C bearing two and three monoterpene units, respectively, exhibited significant cytotoxic activities against the used cell lines with IC₅₀ values 1.5-6.5 μM. Caspicaosides A and D with one monoterpene unit exhibited significant cytotoxic activities on HepG2 cell line with IC₅₀ values equal to 4.5 and 5.4 μM, respectively, and IC₅₀ values >10 μM against the other two cell lines. The number of monoterpene units seems to play a main role in determining the activity.     

Systematic characterisation and seed oil analysis in candidate plus trees of biodiesel plant, Pongamia pinnata

Candidate plus trees (CPTs) of Pongamia pinnata , a potential biodiesel plant occurring across 10 locations in North Guwahati, were identified based on morphological markers (vegetative and reproductive) using combined analysis over locations. Identified CPTs were then multiplied using seed propagation technique in a nursery bed. The performance of the candidate trees with respect to seed and pod traits, the two most important characters with regard to oil, were evaluated using CROPSTAT software for inferring potential genotypes that can be included in programmes aimed at genetic improvement of the species. Total oil content from the seeds of plus trees was also analysed using solvent extraction procedure at their boiling points. Hexane extraction yielded maximum oil content from seeds (33%) compared with petroleum ether (30%). When the seed to solvent ratio varied, no significant difference was noticed on the total oil yield for an individual tree, although the recovery of solvent and the time taken for oil extraction were significantly reduced at higher ratios of solvent used.     

Inflorescence and floral development of Dahlstedtia species (Leguminosae: Papilionoideae: Millettieae)

Inflorescence and floral development of two tropical legume trees, Dahlstedtia pinnata and Dahlstedtia pentaphylla, occurring in the Atlantic Forest of south-eastern and southern Brazil, were investigated and compared with other papilionoids. Few studies have been made of floral development in tribe Millettieae, and this paper is intended to fill that gap in our knowledge. Dahlstedtia species have an unusual inflorescence type among legumes, the pseudoraceme, which comprises axillary units of three or more flowers, each with a subtending bract. Each flower exhibits a pair of opposite bracteoles. The order of flower initiation is acropetal; inception of the floral organs is as follows: sepals (5), petals (5), carpel (1) plus outer stamens (5) and finally inner stamens (5). Organ initiation in sepal, petal and inner stamen whorls is unidirectional; the carpel cleft is adaxial. The vexillum originates from a tubular-shaped primordium in mid-development and is larger than other petals at maturity, covering the keels. The filament tube develops later after initiation of inner-stamen primordia. Floral development in Dahlstedtia is almost always similar to other papilionoids, especially species of Phaseoleae and Sophoreae. But one important difference is the precocious ovule initiation (open carpel with ovules) in Dahlstedtia, the third citation of this phenomenon for papilionoids. No suppression, organ loss or anomalies occur in the order of primordia initiation or structure. Infra-generic differences in the first stages of ontogeny are rare; however, different species of Dahlstedtia are distinguished by the differing distribution pattern of secretory cavities in the flower.     

Micropropagation of <Emphasis Type="Italic">Pongamia pinnata</Emphasis> through enhanced axillary branching

A complete protocol is presented for the first time for the micropropagation of Pongamia pinnata, a biofuel tree, using cotyledonary nodes derived from axenic seedlings. Multiple shoots were induced in vitro from nodal segments through forced axillary branching. Murashige and Skoog (MS) medium supplemented with 7.5 μM benzylaminopurine (BAP) induced up to 6.8 shoots per node with an average shoot length of 0.67 cm in 12 d. Incorporation of 2.5 μM gibberellic acid (GA₃) in the medium during the first subculture after establishment and initiation of shoot buds significantly improved the shoot elongation. Single use of GA₃ during the first subculture eliminated the need for prolonged culturing on BAP medium. Further use of GA₃ in the medium was not useful. Shoot culture was established for at least two subcultures without loss of vigor by repeatedly subculturing the original cotyledonary node on shoot multiplication medium followed by shoot elongation medium after each harvest of the newly formed shoots. Thus, from a single cotyledonary node, about 16–18 shoots were obtained in 60 d. Shoots formed in vitro were rooted on full-strength MS medium supplemented with 1.0 μM indole butyric acid (IBA). Plantlets were successfully acclimated, established in soil, and transferred to the nursery.     

Toxicity degradation of waste soil from a chlor-alkali factory byAzolla pinnata Lam

Cultures ofAzolla pinnata Lam., grown in various mixtures of soil plus industrial waste from a chlor-alkali factory for 30 to 60 days, resulted in the addition of significant amounts of nitrogen and organic carbon to the growing medium. A considerable decrease in the alkaline pH of the waste/soil was also recorded. On transplantation of rice seedlings into the waste/soil mixtures, after 60 days of Azolla culture it was observed that the rice survived and continued to grow in mixtures containing 30% waste whereas, in control conditions, seedlings failed to survive in above 15% waste/soil combinations.     

钒钛磁铁尾矿土壤中水黄皮根瘤菌铁耐受性与钝化能力研究

铁是好氧微生物生长所必需的元素,而铁污染土壤环境中的根瘤菌是否对高浓度铁具有耐受性和钝化能力尚不清楚。以攀枝花钒钛磁铁尾矿土壤作为基质进行水黄皮共生根瘤菌捕获实验,获得水黄皮共生根瘤并从中分离纯化出根瘤菌39株。通过Fe~(2+)/Fe~(3+)耐受性和钝化能力测试筛选出耐受性和钝化能力均强的优势菌株PZHS20、PZHS90、PZHS87,其对Fe~(2+)的最大耐受质量浓度为1 600 mg/L,其中PZHS20在200 mg/L Fe~(2+)溶液中钝化效率最大,为73.54%;PZHS90对Fe~(3+)的最大耐受质量浓度为1 600 mg/L,而PZHS20和PZHS87对Fe~(3+)的最大耐受质量浓度为1 800 mg/L,其在200 mg/L Fe~(3+)溶液中钝化效率分别为84.25%和81.95%。16S rRNA基因系统进化分析将PZHS20鉴定为苍白杆菌(Ochrobactrum),将PZHS90和PZHS87鉴定为慢生根瘤菌(Bradyrhizobium)。研究结果表明,钒钛磁铁尾矿土壤中的水黄皮根瘤菌具有不同程度的Fe~(2+)/Fe~(3+)耐受性和钝化能力,筛选出的优势菌株为进一步利用水黄皮-根瘤菌联合修复高浓度铁污染土壤提供可利用的菌株资源。     

Flavonol tetraglycosides from fruits of Styphnolobium japonicum (Leguminosae) and the authentication of Fructus Sophorae and Flos Sophorae

The dried fruits and seeds of Styphnolobium japonicum (L.) Schott (syn. Sophora japonica L.) are used in traditional Chinese medicine and known as Fructus Sophorae or Huai Jiao. The major flavonoids in these fruits and seeds were studied by LC-MS and other spectroscopic techniques to aid the chemical authentication of Fructus Sophorae. Among the flavonoids were two previously unreported kaempferol glycosides: kaempferol 3-O-β-glucopyranosyl(1 → 2)-β-galactopyranoside-7-O-α-rhamnopyranoside and kaempferol 3-O-β-xylopyranosyl(1 → 3)-α-rhamnopyranosyl(1 → 6)[β-glucopyranosyl(1 → 2)]-β-glucopyranoside, the structures of which were determined by NMR. Two further tetraglycosides were identified for the first time in S. japonicum as kaempferol 3-O-β-glucopyranosyl(1 → 2)[α-rhamnopyranosyl(1 → 6)]-β-glucopyranoside-7-O-α-rhamnopyranoside and kaempferol 3-O-β-glucopyranosyl(1 → 2)[α-rhamnopyranosyl(1 → 6)]-β-galactopyranoside-7-O-α-rhamnopyranoside; the latter was the main flavonoid in mature seeds. The chromatographic profiles of 27 recorded flavonoids were relatively consistent among fruits of similar ages collected from five trees of S. japonicum, and those of maturing unripe and ripe fruits were similar to a market sample of Fructus Sophorae, and thus provide useful markers for authentication of this herbal ingredient. The flower buds (Huai Mi) and flowers (Huai Hua) of S. japonicum (collectively Flos Sophorae) contained rutin as the main flavonoid and lacked the flavone glycosides that were present in flower buds and flowers of Sophora flavescens Ait., reported to be occasional substitutes for Flos Sophorae. The single major flavonoid in fruits of S. flavescens was determined as 3′-hydroxydaidzein.     

In vitro anticancer activity of Spondias pinnata bark on human lung and breast carcinoma

Spondias pinnata, a commonly distributed tree in India, previously proven for various pharmacological properties and also reported for efficient anti-oxidant, free radical scavenging and iron chelating activity, continuing this, the present study is aimed to investigate the role of 70 % methanolic extract of S. pinnata bark (SPME) in promoting apoptosis in human lung adenocarcinoma cell line (A549) and human breast adenocarcinoma cell line (MCF-7). These two malignant cell lines and a normal cell line were treated with increasing concentrations of SPME and cell viability is calculated. SPME showed significant cytotoxicity to both A549 and MCF-7 cells with an IC₅₀ value of 147.84 ± 3.74 and 149.34 ± 13.30 μg/ml, respectively, whereas, comparatively no cytotoxicity was found in normal human lung fibroblast cell line (WI-38): IC₅₀ 932.38 ± 84.44 μg/ml. Flow cytometric analysis and confocal microscopic studies confirmed that SPME is able to induce apoptosis in both malignant cell lines. Furthermore, immunoblot result proposed the pathway of apoptosis induction by increasing Bax/Bcl-2 ratio in both cell types, which results in the activation of the caspase-cascade and ultimately leads to the cleavage of Poly adeno ribose polymerase. For the first time this study proved the anticancer potential of SPME against human lung and breast cancer by inducing apoptosis through the modulation of Bcl-2 family proteins. This might take S. pinnata in light to investigate it for further development as therapeutic anticancer source.