ABSTRACT
Tillandsia L. genus comprises 649 species, with different uses at different times. T. usneoides L. uses are reported since the late- archaic and pre-Columbian cultures. In XIX-XX centuries, T. usneoides was used in some manufactured products, as polish and packing fruit. Tillandsia has a favorable reputation as medicine: for leucorrhea, rheumatism, ulcers, hemorrhoid treatment, as an anti-diabetic remedy, emetic, analgesic, purgative, contraceptive, antispasmodic and diuretic. Tillandsia chemical composition includes cycloartane triterpenes and hydroxy-flavonoids, which are present in at least 24 species. Several extracts and compounds from Tillandsia spp. have been reported with pharmacological actions, as anti-neoplasia, hypolipidemic, antifungal, anti-HSV-1, hypoglycemic and microbicide. This review communicates the economic importance, ethnobotany, chemistry composition and biological activities of the Tillandsia genus, and analyze its biological and economic perspective. Tillandsia genus has cultural, economic and pharmacological relevance, with a high potential in many essential aspects of the modern society.
El geÌnero Tillandsia L. comprende 649 especies, con diferentes usos en diferentes eÌpocas. T. usneoides L. se han reportado desde el arcaÌico tardiÌo hasta las culturas precolombinas. En los siglos XIX-XX, T. usneoides se usoÌ en productos manufacturados: como abrasivo y embalaje de fruta. Como medicina tradicional, el geÌnero Tillandsia se reporta para leucorrea, reumatismo, uÌlceras, hemorroides, remedio antidiabeÌtico, emeÌtico, analgeÌsico, purgante, anticonceptivo, antiespasmoÌdico y diureÌtico. Su composicioÌn quiÌmica incluye triterpenos de tipo ciclo-artano e hidroxi-flavonoides, presentes en al menos 24 especies. Los extractos y compuestos del geÌnero Tillandsia se han reportado con propiedades antineoplaÌsicas, hipolipideÌmicas, antifuÌngicas, anti-HSV-1, hipoglucemiantes y microbicidas. Esta revisioÌn comunica la importancia econoÌmica, etnobotaÌnica, composicioÌn quiÌmica y las actividades bioloÌgicas del geÌnero Tillandsia, y analiza su perspectiva bioloÌgica y potencial econoÌmica. Tillandsia tiene importancia cultural, econoÌmica y farmacoloÌgica, con gran potencial en muchos aspectos esenciales de la sociedad moderna.
Subject(s)
Plants, Medicinal/chemistry , Plant Extracts/chemistry , Ethnobotany , Tillandsia/chemistry , Triterpenes/analysis , Plant Extracts/pharmacology , Bromeliaceae/chemistryABSTRACT
The genus Actaea plants are widely distributed in China, and the cycloartane triterpenoids are the characteristic constituents of this genus. They are divided into types of cimigenol, hydroshengmanol, shengmanol, cimiacerogenin, acteol, 16, 23-diketo, foetidonol, dahurinol, etc. Cycloartane triterpenoids show many biological activities, such as cytotoxicity, anti-osteoporosis, antiviral, anti-inflammatory, anti-nucleoside transport, neuroprotective, anti-oxidant, antibacterial activities. The present paper reviewed the distribution of the plant resources of Actaea, chemical structures and biological activities of cycloartane triterpenoids, aiming to provide a reference for the further research in the future.
Subject(s)
Actaea , Chemistry , China , Phytochemicals , Chemistry , Pharmacology , Triterpenes , Chemistry , PharmacologyABSTRACT
Aim To investigate the antitumor effects of cimigenol ( KY17 ) , a novel cycloartane triterpenoid from Cimicifuga , in human colon cancer cells (HCT116).Methods MTT assay was used to deter-mine the effect of KY17 on the proliferation of mouse embryonic fibroblasts ( MEF) and human colon cancer HCT116 cell line.Flow cytometry was employed to de-tect the effect of KY17 on HCT116 cell cycle.Fluores-cence microscopy and flow cytometry were used to ana-lyze the apoptosis .Western blot was used to detect the expression of apoptotic protein (PARP).q-PCR ana-lyzed the expression of miRNA-34a.Results The IC50 of KY17 in MEF and HCT116 cells was 27.28 μmol· L-1 and 9.31μmol· L-1 , respectively.KY17 induced HCT116 cell cycle arrest in G2/M phase and the apoptotic protein PARP cleavage . In addition, KY17 up-regulated the expression of p 53 protein and miRNA-34a.Conclusions KY17 inhibits the prolifera-tion and the cell cycle is arrested in G 2/M, inducing the apoptosis of HCT116 cells. The mechanism is probably related to miRNA-34a up-regulation and p53 activation .
ABSTRACT
In the present study, one new cycloartane triterpenoid, named cycloccidentalic acid C (1) and its glucoside, cycloccidentaliside VI (2) were isolated from the whole plant of Cassia occidentalis. Their structures were elucidated by a combinational analyses of 1D and 2D NMR data and HRMS. Compound 2 showed modest anti-HIV-1 activity with EC value of 1.44 μmol·L and TI (Therapeutic Index) value of 15.59.
Subject(s)
Humans , Anti-HIV Agents , Pharmacology , Cell Line, Tumor , Cell Survival , Glucosides , Chemistry , Pharmacology , Toxicity , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Extracts , Chemistry , Pharmacology , Toxicity , Senna Plant , Chemistry , Triterpenes , Chemistry , Pharmacology , ToxicityABSTRACT
Medicinal plants in Cimicifuga L. contain triterpenoid glycosides, phenolic acids, chromones and other ingredients, showed biological activities of antitumor, anti-inflammatory, antiviral, anti-nucleoside transport, anti-osteoporosis, anti-oxidant, antidepression, etc, and have been used in the treatment of perimenopausal syndrome. This paper reviews the advances in studies on chemical constituents cimicifuga, focuses on the research progress of biological activities and clinical applications to provide a reference for further development of medicinal plants in Cimicifuga L.
ABSTRACT
Secocycloartanes are a class of triterpenoids with novel structures showing anti-HIV and antitumor activities. This review summarized the structures, bioactivities and plant distribution of secocycloartane triterpenoids reported from plants but Schisandraceae in recent years to provide a basis for further study of this type of compound and the discovery of new drugs.
ABSTRACT
Objective: To study the chemical constituents in the whole plant of Pteris deltodon. Methods: Nine compounds were isolated from 95% ethanol extract in the whole plant of P. deltodon and purified by silica gel chromatography, Sephadex LH-20, and pre-HPLC, and their structures were identified on the basis of spectroscopic data and literatures. Results: Nine compounds were isolated and elucidated as β-sitosteol (1), (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (2), ent-kaur-16-ene-2β,15α-diol (3), cycloart-23-en-3β,25-diol (4), cycloart-25-en-3β,24-diol (5), emodin (6), 1,7-dihydroxyxanthone (7), ursolic acid (8), and ergosterol (9). Conclusion: All the compounds are for the first time isolated from P. deltodon; Compound 4 and 5 are cycloartanes first isolated from genus Pteris L.
ABSTRACT
The Phytochemical study of Methanol/dichloromethane extract of root of Leplaea mayombenis led to the isolation and identification four limonoids: (8S,9R,10R,11S,13R,17R)-6,11-dihydroxy-14,15-epoxy-4,4,8,10,13-pentamethyl-17-(2-oxo-2,5-dihydrofuran-3-yl-)-11,12,13,15,16,17-hexahydro-4H-cyclopent[α] phenanthrene-3,7(8H,9H,10H,14H)-dione (1), (8S,9R,10R,11S,13R,17R)-6,11-dihydroxy-14,15-epoxy-4,4,8,10,13-pentamethyl -17-(23-methoxy-2-oxo-2,5-dihydrofuran-3-yl-)-11,12,13,15,16,17-hexahydro-4H-cyclopent [α] phenanthrene 3,7(8H,9H,10H,14H)-dione (2), (8S,9R,10R,11S,13R,17R)-6,11-dihydroxy-14,15-epoxy-17- ((s)-2-hydroxy-5-oxo-2,5-dihydrofurano-3-yl)-4,4,8,10,13-pentamethy-l,10,11,12,13,15,16,17-octahydro-4H-cyclopent [α] phenanthrene-3,7(8H,9H,10H,14H)-dione (3), 8S,9R,10R,11S,13R,17R)-1,6,11-trihydroxy-14,15-epoxy-17- [((2s)-2-hydroxy-5-oxo-2,5-dihydrofurano-3-yl)]-4,4,8,10,13-pentamethyl-l,10,11,12,13,15,16,17-octahydro-4H-cyclopent[α]phenanthrene-3,7(8H,9H,10H,14H)-dione (4), one cycloartane : 9,10-cyclopropyl-(3S,5R,8R,13R,14S,17R))-4,4,13,14,17-pentamethyl-l7-((2R,5S,6R)-5,6,7-trihydroxy-6-methylheptan-2-yl)-hexadecahydro-1H-cyclopentane[α]phenanthrèn-3-ol (5) and three steroids: β-sitosterol (6), stigmasterol (7) and stigmasterol 3-O-β-D-glucopyranoside (8). Their structures were elucidated on the basis of spectroscopic analysis and by comparison of their spectral data with those reported in the literature. To the best of our knowledge, all these compounds were isolated for the first time from the Leplaea mayombensis. The antimicrobial studies showed that isolated compounds exhibit antimicrobial activity with inhibition zone diameters varying from 0.00 ± 0.00 to 29.00 ± 0.00 mm on both bacteria and fungi. 9,10-cyclopropyl-(3S,5R,8R,13R,14S,17R) )-4,4,13,14,17-pentamethyl-l7-((2R,5S,6R)-5,6,7-trihydroxy-6-methylheptan-2-yl)-hexadecahydro-1 H-cyclopentane[α] phenanthrèn-3-ol (5) was the most active against Escherichia coli (28.00±0.00 mm), Pseudomonas sp (27.00±0.00 mm), Lactobacillus acidophilus (29.00±0.00 mm), Streptococcus pneumonia (23.00±0.00 mm) and Serratia entomophili (29.00±0.00 mm), C. albicans (12±0.00 mm), and T. viridae (13±0.00 mm) The results from this study support the conclusion that L. mayombensis contain many classes of antimicrobial compounds and therefore justify their traditional usage in the treatment of infectious diseases.
ABSTRACT
Aim: The role of Kinases in cancer onset and progression has made kinases a target for the control of some cancers. Recent discoveries that kinases are most effectively inhibited by small molecules have also resulted in an increased search for small molecule kinase inhibitors. Cycloartanes are small molecules found in many medicinal plants including the Jamaican Ball Moss (Tillandsia recurvata). Recent studies on T. recurvata have demonstrated that it possesses anticancer activity. Cycloartane-3,24,25- triol, an analog of a cycloartane identified in Ball moss was also shown to have inhibitory activity against MRCKα kinase. This study was as such set up to determine the MRCKα/β kinase inhibition activity of other cycloartanes in Ball Moss and their analogs. MRCKα/β kinases has been identified as an important kinase implicated in cancer onset and progression and as such a potential drug target. Methodology: Kinase inhibition activity of 6 cycloartanes was investigated using the ligand-kinase binding assay. The WST-1 reagent assay was also used to determine the antiproliferation activity of the cycloartanes against some prostate and breast cancer cell lines. Results: Cycloart-23-ene-3,25-diol (1), Cycloartane-3,24,25-triol (2), Cycloart-25-ene- 3,24-diol (3), 3,23-Dioxo-9,19-cyclolanost-24-en-26-oic acid (4), 24,25- Dihydroxycycloartan-3-one (5) inhibited the MRCKα kinase with Kd of 0.21 μM, 0.25μM, 0.36 μM, 3.0 μM and 2.1 μM respectively. Hydroxycycloart-23-en-3-one,25, (6) showed no inhibition against the MRCKα kinase. Compounds 1, 3, 4, 5 inhibited the MRCKβ kinase with Kd of 4.7 μM, 1.10 μM, 3.2 μM and 9.8 μM, respectively. Three of the six cycloartanes exhibited antiproliferation activity against two prostate and breast cancer cell lines each. Conclusion: Cycloart-23-ene-3,25-diol (1) showed the most promising activity against the MRCKα/β kinase out of the 6 cycloartanes screened demonstrating an interesting structure activity relationship profile when compared with the other molecules. Cycloart- 23-ene-3,25-diol (1) deserves further studies to determine its in vivo activity as well.
ABSTRACT
AIM@#To study the 9, 19-cycloartane triterpenes from the roots of Cimicifuga foetida.@*METHOD@#Chromatographic separations by silica gel, C18 reversed phase silica gel, and high-performance liquid chromatography (HPLC) were used. All of the structures were elucidated on the basis of spectroscopic analysis and chemical methods.@*RESULTS@#Five 9, 19-cycloartane triterpenes, (3β, 12β, 15α, 24R)-12, 2'-diacetoxy-24, 25-epoxy-15-hydroxy-16, 23-dione-3-O-α-L-arabinopyranoside (1), actein (2), 23-epi-26-deoxyactein (3), asiaticoside B (4), and 12β-hydroxycimigenol (5) were isolated from the roots of Cimicifuga foetida.@*CONCLUSION@#Compound 1 is a new triterpene with two acetoxy groups at C-2' and C-12.
Subject(s)
Cimicifuga , Chemistry , Drugs, Chinese Herbal , Chemistry , Molecular Structure , Plant Roots , Chemistry , Triterpenes , ChemistryABSTRACT
The hepatoprotective activity of the ethanol extract of Astragalus kahiricus (Fabaceae) roots against ethanol-induced liver apoptosis was evaluated and it showed very promising hepatoprotective actions through different mechanisms. The extract counteracted the ethanol-induced liver enzymes leakage and glutathione depletion. In addition, it demonstrated anti-apoptotic effects against caspase-3 activation and DNA fragmentation that were confirmed by liver histopathological examination. Moreover, the phytochemical study of this extract led to the isolation of four cycloartane-type triterpenes identified as astrasieversianin II (1), astramembrannin II (2), astrasieversianin XIV (3), and cycloastragenol (4). The structures of these isolates were established by HRESI-MS and 1D and 2D NMR experiments. The antimicrobial, antimalarial, and cytotoxic activities of the isolates were further evaluated, but none of them showed any activity.
Subject(s)
Animals , Female , Humans , Rats , Apoptosis , Astragalus Plant , Chemistry , Caspase 3 , Metabolism , Chemical and Drug Induced Liver Injury , Drug Therapy , Genetics , DNA Fragmentation , Ethanol , Toxicity , Liver , Cell Biology , Plant Extracts , Plant Roots , Chemistry , Protective Agents , Rats, Sprague-DawleyABSTRACT
The biological activitites of Dikamaliartane-A, a cycloartane isolated from gum resin Dikamali of Gardenia gummifera/Gardenia lucida was screened for some pharmacological actions. The study was carried out using albino mice (20-25gr). It reduced locomotor activity and potentiated pentobarbitone-induced sleeping time in mice indicating Central Nervous System depressant activity. It protected mice from strychnine and electro shock–induced convulsions indicating that it has anti-convulsant activity. All these activities were statistically significant. The LD50 (Lethal Dose) was carried out in mice according to Organization for Environmental Cooperation and Development (OECD) Guidelines 423. The LD50 was tested in three mices for each dose with doses from 5mg/kg, 50mg/kg, 300mg/kg and 2000mg/kg. The LD50 was found to be 500mg/kg.
ABSTRACT
Object To isolate and identify the chemical constituents from the rhizome of Cimicifuga dahurica (Turcz ) Maxim Methods The different chromatographic techniques were used to isolate ten constituents, and the spectral methods, such as IR, MS, 1HNMR, 13 CNMR and 2DNMR, were used to identify the structures Results Their structures were identified as cimigenol (Ⅰ), 24 epi 7, 8 didehydrocimigenol 3 O ? D xylopyranoside (Ⅱ), 7, 8 didehydrocimigenol 3 O ? D xylopyranoside (Ⅲ), 25 O acetyl 7, 8 didehydrocimigenol 3 O ? D xylopyranoside (Ⅳ), 3 arabinosyl 24 O acetylhydroshengmanol 15 glucoside (Ⅴ), isoferulic acid (Ⅵ), (E) 3 (3′ methyl 2′ butenylidene) 2 indolinone (Ⅶ), sucrose (Ⅷ), ? sitosterol (Ⅸ) and stigmastenol 3 O ? D glucopyranoside (Ⅹ), respectively Conclusion Compounds Ⅱ Ⅳ, Ⅹ are isolated for the first time from the title plant