Steroidal sapogenins from leaves of Agaveae species

The steroidal sapogenins yielded by the leaves of 34 species and 1 cultivar of Agave, 1 species of Beschorneria, 1 species of Doryanthes and 3 species of Furcraea have been studied. Steroidal sapogenins were found in extracts of most of the species examined. Smilagenin, sarsasapogenin, diosgenin, yamogenin, tigogenin, neotigogenin, gloriogenin, gentrogenin, hecogenin, sisalagenin, 9-dehydrohecogenin and gitogenin were detected. Gloriogenin was found only in A. ghiesbrechtii, yamogenin in A. horrida and A. rigidissima, neo-tigogenin in A. horrida and A. toneliana and gitogenin in A. filifera, F. cabua, F. gigantea and F. selloa cv marginata. The highest yield of smilagenin was obtained from both A. haynaldii and A. rigidissima, of sarsasapogenin from A. attenuata, of diosgenin from A. ellemeetiana, of tigogenin from A. haynaldii and of hecogenin from F. cabua.     

Steroidal sapogenins. LVIII. Steroidal sapogenins from the Joshua tree

The Joshua tree,Yucca brevifolia, is distributed over parts of Arizona, California, Nevada, and Utah. A study of its steroidal sapogenins showed that the leaves contain practically none; the wood, small amounts of smilagenin; the seeds high amounts of hecogenin and tigogenin.     

Sapogenins of Yucca glauca seeds

From the seeds of Yucca glauca Nutt., sarsasapogenin. markogenin. tigogenin. neo-tigogenin. neo-gitogenin, hecogenin and gloriogenin have been isolated and identified. Sarsasapogenin was the predominant sapogenin. Markogenin and gloriogenin have not been reported in leaves, roots or rhizomes of this species before. Small amounts of a sapogenin believed to be either diosgenin or yamogenin were also detected.     

Saponins in Tribulus terrestris – Chemistry and Bioactivity

Tribulus terrestris is a valuable herb known for its application in the folk medicine in many parts of the world. Furostanol and spirostanol saponins of tigogenin, neotigogenin, gitogenin, neogitogenin, hecogenin, neohecogenin, diosgenin, chlorogenin, ruscogenin and sarsasapogenin type are frequently found in this plant. Four sulphated saponins of tigogenin and diosgenin type are also isolated. Extracts and steroidal saponins have been found to possess various pharmacological activities. Preparations based on the saponin fraction of T. terrestris are used for treatment of infertility and libido disorders in men and women, as well as for treatment of cardiac diseases. Food supplements containing T. terrestris extracts are on sale in USA and Europe with claim of a general stimulating action. In this review the steroidal saponins found in T. terrestris are presented, covering the literature up to 2004. The data reveal clear difference in the saponin composition of samples from this plant species collected from different geographical regions. A comprehensive account on the biological activity of extracts and individual saponins is also included.     

Sapogenins of Yucca glauca seed pods

From the fruiting pods of Yucca glauca Nutt. devoid of seeds the following sapogenins have been isolated and identified: neo-tigogenin, hecogenin, gitogenin, manogenin, Δ⁹-manogenin and sarsasapogenin. A small amount of a material believed to be Δ²-desoxysarsasapogenin was also isolated and is apparently an artifact arising from the hydrolysis and extraction procedure. Manogenin and Δ⁹-manogenin have not been previously detected in Y. glauca, and Δ⁹-manogenin has not been reported in any Yucca species.     

A quantitative gas-liquid chromatographic method for the estimation of hecogenin and tigogenin in the leaves, juice and sapogenin concentrates of Agave sisalana

A gas-liquid chromatographic method has been devised for the routine estimation of the hecogenin [3beta-hydroxy-(25R)-5beta-spirostan-12-one] and tigogenin [ (25R)-5beta-spirostan-3beta-ol] contents of Agave sisalana leaf and juice samples and of the crude sapogenin concentrates known as "coffee grounds". Because of partial degradation of the sapogenins in the GLC system it was found necessary to acetylate the compounds prior to their estimation. In East African samples the tigogenin proportion of the total sapogenin content is usually about 10%. At this level, the 95% inverse tolerance limits on predicted tigogenin weights are approximately +/- 7%.     

蒺藜甾体皂甙元化学成分研究

从蒺藜(Tribulus terrestris)的氯仿部位分离得到8个已知的甾体皂甙元类化合物,运用光谱分析方法鉴定分别为：tigogenin(1),hecogenin(2),pregna 4,16 diene-3,12,20-trione(3),hecogenin acetate(4),25(R)-spirostan-4-ene-3,12-dione(5),25(R)-spirostan-3,12-dione(6),25(R)-spirostan-3,6,12-trione(7),gitogenin(8)。其中化合物3,5,6为首次从该植物中分得。     

Production of sapogenins (stigmasterol and hecogenin) from genetically transformed hairy root cultures of <Emphasis Type="Italic">Chlorophytum borivilianum</Emphasis> (Safed musli)

Chlorophytum borivilianum belonging to the family Liliaceae, is distributed in the pantropical regions of India and South Africa. The sapogenins (stigmasterol and hecogenin) of C. borivilianum are well known for their appetizing and aphrodisiac properties. The present study involves enhancing the sapogenin content in C. borivilianum by genetic transformations with Agrobacterium rhizogenes strains (MTCC 2364 and 532, PRT Gus). A maximum transformation frequency of 98% was obtained with Agrobacterium rhizogenes MTCC 2364 strain with rhizome explants after a co-cultivation period of 48 h. Two potential rhizoclones (2364a and 2364b) were selected for the production of stigmasterol and hecogenin. The maximum production of stigmasterol (83.952?±?0.01 mg/g) was seen in 2364b rhizoclone, whereas, the highest accumulation of hecogenin (81.52?±?0.02 mg/g) was observed in 2364a rhizoclone. The C. borivilianum hairy root cultures obtained in this study provide a continuous and sustainable production of stigmasterol and hecogenin on a commercial scale.     

Effect of chemical mutagens on steroidal sapogenins in Trigonella species

A two- to four-fold increase in the steroidal sapogenins (diosgenin and tigogenin) was observed in the plants and seeds obtained from seeds of T. corniculata and T. foenum-graecum treated with low concentrations of chemical mutagens (EMS, MMS and NaN₃). However, a decrease in their levels was recorded at high concentrations of the mutagens.     

Steroid sapogenins from Tristagma uniflorum

From bulbs of Tristagma uniflorum the known sapogenins tigogenin, neotigogenin and (20S,22R,25S)-5α-spirostan-3β,25-diol, as well as the new (20S,22R,25R)-5α-spirostan-3β,25-diol, (20S,22S,25S)-5α-furostan-22,25-epoxy-3β,26-diol and (20S,22S,25R) -5α-furostan-22,25-epoxy-3β,26-diol, were isolated and characterized by spectroscopic (IR, ¹H NMR, ¹³C NMR, MS) methods.     

Investigations on the content of steroidal alkaloids and sapogenins withinSolanum sect.Solanum ( = sect.Morella) (Solanaceae)

Plant material of 55 strains from 32 species ofSolanum sect.Solanum ( = sect.Morella) has been investigated for the content of steroidal alkaloids and sapogenins. The leaf-extracts of all species contain diosgenin resp. tigogenin or both together in considerable amount. On the contrary the characteristic steroidal alkaloid solasodine was absent in these samples. For 29 species the presence of steroidal sapogenins has been proved for the first time. In unripe fruits, however, solasodine could be detected in most of the species examined. New occurences of solasodine are reported for seven further species. These chemical results may contribute to a better comprehension of the difficult genusSolanum.—Ontogenetic studies on different organs ofS. atriplicifolium show the relationship between accumulation of steroidal compounds and plant maturity.     

16β-Hydroxycholestanol als biogenetische vorstufe der steroidsapogenine

It has been shown that 5,6-³H,16β-hydroxycholestanol is used in the biogenesis of the steroid sapogenins, tigogenin and gitogenin, by plants of Digitalis lanata but not for the formation of tomatidine by Solanum lycopersicum.     

Bioactive polar natural compounds from garlic and onions

Bioactive natural compounds from garlic and onions have been the focus of researches for decades, firstly due to their pharmacological effects, and secondly due to their defence properties against plant diseases. In fact, garlic and onion, belonging to Allium genus, are among the oldest food plants known since ancient times and used as ingredient of many recipes and for therapeutic properties. These plants are well known to produce bioactive apolar sulphur compounds but less is known about their polar natural compounds, such as phenols, sapogenins and saponins, that are more stable to cooking, So, we continued our work on the discovery of polar bioactive metabolites from Allium with the isolation of a number of sapogenins and saponins from the wild onion species Allium elburzense, Allium hirtifolium, Allium atroviolaceum, and Allium minutiflorum, and, more recently, from the cultivated white onion, Allium cepa, and garlic, Allium sativum. In particular, the sapogenins and saponins isolated from A. elburzense and A. hirtifolium, named elburzensosides and hirtifoliosides respectively, exhibited significant antispasmodic properties. In addition, the saponins named minutosides isolated from A. minutiflorum showed promising antimicrobial activity. More recently the phytochemical analysis of A. cepa and A. sativum has been undertaken and afforded the characterization of saponins, phenols and N-cynnamic amides which showed significant antifungal activity.     

Activities of arginine and ornithine decarboxylases in various plant species

In extracts from the youngest leaves of Avena sativa, Hordeum vulgare, Zea Mays, Pisum sativum, Phaseolus vulgaris, Lactuca sativa, and four pyrrolizidine alkaloid-bearing species of Heliotropium, the activities of ornithine decarboxylase, close to V_max, ranged between traces and 1.5 nanomoles per hour per gram fresh weight when based on putrescine formed during incubation with labeled ornithine. The arginine decarboxylase activities in the same extracts ranged between 8 and 8000 nanomoles per hour per gram fresh weight being lowest in the borages and highest in oat and barley. α-Difluoromethylornithine and α-difluoromethylarginine inhibited ornithine and arginine decarboxylases, respectively, in all species. Agmatine, putrescine, spermidine, and spermine were found in all, diaminopropane in eight, and cadaverine in three species.

No correlation was observed between arginine or ornithine decarboxylase level and the levels of total polyamines. The in vitro decarboxylase activities found in the borages cannot explain the high accumulation of putrescine-derived pyrrolizidines in their youngest leaves if the pyrrolizidines are produced in situ from arginine and/or ornithine as precursors; other possibilities are discussed.

In assays of ornithine decarboxylase, an interference of decarboxylation not due to this enzyme was observed in extracts from all species. In arginine decarboxylase assays, the interfering decarboxylation as well as the interference of arginase were apparent in two species. Addition of aminoguanidine was needed to suppress oxidative degradation of putrescine and agmatine during incubation of extracts from pea, bean, lettuce, Heliotropium angiospermum, and Heliotropium indicum.

     

3,4-Seco-spirostane sapogenins with cytotoxic activity from Allium umbilicatum boiss

Two new sapogenins, named seco-umbilicagenins A and B (1 and 2), possessing a new chemical structure based on a 3,4-seco-spirostane skeleton, were isolated from Allium umbilicatum Boiss. The chemical structures of seco-umbilicagenins A and B were established through a combination of extensive spectroscopic analysis, mainly nuclear magnetic resonance spectroscopy and mass spectrometry, and chemical methods as (2S,25R)-2,5α,6β-trihydroxy-3,4-seco-spirosta-3,4-dioic acid (1) and (2S,25R)-2,4,5α-trihydroxy-6-oxo-3,4-seco-spirostan-3-oic acid (2). Interestingly, the isolated compounds exhibited cytotoxic activity on J-774, murine monocyte/macrophage, and WEHI-164, murine fibrosarcoma, cell lines. To the best of our knowledge this is the first time that 3,4-seco-spirostane sapogenins are isolated from natural sources, being this skeleton obtained by synthetic modification of intact sapogenins.     

Subspecies boundaries and recent evolution history of the common pheasant (Phasianus colchicus) across China

The mitochondrial DNA (mtDNA) control region of two hundreds and thirty-six common pheasants (belonging to fourteen subspecies collected at twenty-eight localities) was used to investigate the subspecies status of Phasianus colchicus. Eighty-nine variable sites defined one hundred and thirty-nine haplotypes. Phylogenetic analysis of haplotypes revealed that P. c. shawii, P. c. mongolicus and P. c. suehschanensis were monophyletic. P. c. shawii and P. c. mongolicus were isolated by the Taklimakan, the Bardain, the Jaran and the Gurbantonggut Deserts where the two subspecies evolved independently. P. c. suehschanensis was isolated by the forest and mountains in the Sichuan Basin where it evolved independently. Further eleven subspecies were identified and split into the western and eastern groups. The divergence occurred in the late Pleistocene when the arid, semi-arid and monsoon regions formed, and it was induced by the isolation from the Qinling and Taihang Mountains. Fst-values decreased from 0.543 (for twenty-eight populations) to 0.541 (for fourteen subspecies). In light of these results, we suggest that the currently recognized subspecies do not reflect the evolutionary history of the common pheasant.     

Natural urease inhibitors from Aloe vera resin and Lycium shawii and their structural-activity relationship and molecular docking study

Bio-assay guided fractionation of the methanolic extract of Aloe vera resin and Lycium shawii stem successively afforded twenty three compounds; fourteen (1–14) from A. vera and nine (15–23) from L. shawii. All these compounds were characterized by 1D and 2D NMR spectroscopic techniques viz., ¹H, ¹³C, DEPT, HSQC, HMBC, and COSY, and NEOSY, ESI-MS and compared with the reported literature. These compounds were assessed for their potential as urease inhibitors targeted in peptic ulcer. Among crude extracts and fractions of A. vera resin, n-butanol fraction (23.5 ± 1.7 μg·mL⁻¹) showed the most potent urease inhibition followed by methanol (30.9 ± 0.3 μg/mL) and ethyl acetate (31.7 ± 0.5 μg·mL⁻¹). In case of L. shawii, ethyl acetate fraction exhibited the highest urease activity (41.0 ± 1.4 μg/mL) trailed by dichloromethane (55.2 ± 1.5 μg/mL) fraction. Among the isolates, compounds 7, 11 and 23 were found to be excellent urease inhibitors with IC₅₀ values of 14.5 ± 0.90 µM, (16.7 ± 0.16 µM) and 14.0 ± 0.8 µM, respectively. To the best of our knowledge, this is the first report on the urease enzyme inhibitory activity of the said compounds excluding compound 18. In addition, the urease activity of different fractions of L. shawii stem was also reported for the first time. The molecular docking studies showed that all the active compounds well accommodate in the active site of the urease enzyme by interacting with key amino acids.     

Seasonal variation in antimicrobial and phytochemical properties of frequently used medicinal bulbous plants from South Africa

The growing popularity of traditional medicine and the unrestricted collection of medicinal plants from the wild have put many of the slow growing bulbous plant species at the risk of over-exploitation and extinction in South Africa. This study was aimed at comparing the phytochemical composition and biological (antibacterial and anticandidal) activities of bulb and leaf extracts of Tulbaghia violacea, Hypoxis hemerocallidea, Drimia robusta and Merwilla plumbea between spring, summer, autumn and winter seasons, with the view of promoting the use of leaves, as a conservation strategy. Antibacterial and anticandidal activities of petroleum ether (PE), dichloromethane (DCM), 80% ethanol and water extracts of bulbs and leaves were tested against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae bacteria and the fungus Candida albicans using the microdilution bioassay. Spectrophotometric methods were used to evaluate saponin and phenolic compositions for the four seasons. Leaf and bulb extracts exhibited comparable anticandidal activity (MIC < 1 mg/ml) in all the plant species in all seasons. Only ethanol and water extracts of H. hemerocallidea corms (autumn and winter) showed correspondingly good fungicidal activity amongst the bulbs tested. Antibacterial activity was fairly comparable between bulbs and leaves with at least one extract of each plant species showing some good MIC values in most of the seasons. The best antimicrobial activities were recorded in winter and autumn seasons, with MIC values as low as 0.2 mg/ml in the DCM bulb extracts of T. violacea (winter) against K. pneumoniae and S. aureus. The amounts of total phenolic compounds in all plant samples were generally higher in spring compared to the other seasons. Condensed tannin, gallotannin and flavonoid levels, depending on the sample, were either higher in spring or winter except for H. hemerocallidea (corm) which had higher gallotannin levels in autumn. Total saponin levels were higher in winter in all plant samples. Although variation was observed in the phytochemical concentrations between the bulbs and leaves of each plant species, their antimicrobial activities were fairly comparable. Leaves may be used as substitutes for bulbs in the treatment of bacterial and fungal ailments.     

Biosynthesis and desaturation of prokaryotic galactolipids in leaves and isolated chloroplasts from spinach

Mono- and digalactosyldiacylglycerol (MGDG and DGDG) were isolated from the leaves of sixteen 16:3 plants. In all of these plant species, the sn-2 position of MGDG was more enriched in C₁₆ fatty acids than sn-2 of DGDG. The molar ratios of prokaryotic MGDG to prokaryotic DGDG ranged from 4 to 10. This suggests that 16:3 plants synthesize more prokaryotic MGDG than prokaryotic DGDG. In the 16:3 plant Spinacia oleracea L. (spinach), the formation of prokaryotic galactolipids was studied both in vivo and in vitro. In intact spinach leaves as well as in chloroplasts isolated from these leaves, radioactivity from [1-¹⁴C]acetate accumulated 10 times faster in MGDG than in DGDG. After 2 hours of incorporation, most labeled galactolipids from leaves and all labeled galactolipids from isolated chloroplasts were in the prokaryotic configuration. Both in vivo and in vitro, the desaturation of labeled palmitate and oleate to trienoic fatty acids was higher in MGDG than in DGDG. In leaves, palmitate at the sn-2 position was desaturated in MGDG but not in DGDG. In isolated chloroplasts, palmitate at sn-2 similarly was desaturated only in MGDG, but palmitate and oleate at the sn-1 position were desaturated in MGDG as well as in DGDG. Apparently, palmitate desaturase reacts with sn-1 palmitate in either galactolipid, but does not react with the sn-2 fatty acid of DGDG. These results demonstrate that isolated spinach chloroplasts can synthesize and desaturate prokaryotic MGDG and DGDG. The finally accumulating molecular species, MGDG(18:3/16:3) and DGDG(18:3/16:0), are made by the chloroplasts in proportions similar to those found in leaves.