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Chemical Constituents of Cayratia trifolia
Abstract
The wide-ranging medicinal values of Cayratia trifolia (L.) Domin. are well-documented both in folk medicine and pharmacological studies. This study was conducted to investigate the chemical constituents of the dichloromethane extract of the air-dried leaves of C. trifolia. This led to the isolation of a mixture of β-sitosterol (1) and stigmasterol (2) in about 5:1 ratio, squalene (3) and lutein (4). The structures of 1-4 were identified by comparison of their 13C NMR data with those reported in the literature.
... [1][2][3][4][5] The leaves of C. trifolia contained β-sitosterol, stigmasterol, squalene and lutein. [6] The stem, leaves and roots possessde hydrocyanic acid and delphinidin. The seeds and fruits yielded cyanogenic compounds. ...
Cayratia trifolia (L.) Domin (family Vitaceae) is a deciduous,
glabrous, perennial, climbing shrub used to treat boilds, fractured
bones, dandruff, eczema, fever, food poisoning, lymphatic swellings
and muscular pain. Abies webbiana (Wall ex D. Don) Lindl. (family
Pinaceae) is a large, tall, evergreen, aromatic, coniferous tree; and its
leaves are used to treat cough, asthma, bronchitis, common cold, nasal
congestion, rhinitis, fever, gas, headache, malaria, neuralgia, phthisis,
rheumatism, catarrh of the bladder and excessive phlegm. This study
was planned to isolate phytoconstituents from these plant materials and
to characterize their structures. The leaves of C. trifolia afforded nhexadecanyl n-octadec-9, 12-dienoate (n- hexadecanyl linoleate, 1), nheptadecanyl n-octadec-9, 12- dienoate (n-heptadecanyl linoleate, 2),
n-docosanyl n-octadec-9, 12- dienoate ( n-docosanyl linoleate, 3), n-docosanyl n-octadec-9-
enoate (n-docosanyl oleate, 4), and n-tridecanyl n-octadec-9, 12-dienoate (n-tricosanyl
linoleate, 5). The leaves of Abies webbiana produced a new bicyclic sesquiterpenic
arabinoside characterized as bezzan-2,4-dien-15-oate 15α-D-arabinopyronoside (6). The
structures of isolated phytoconstituents were established on the basis of analysis of spectral
data and chemical means.
... Besides, aerial Part of this plant contains kaempferol, myricetin, quercetin, epifriedelanol and triterpenes. 8,11,12 ...
Introduction: Infection H. pylori causes inflammation through various pathways to induce proinflammatory cytokines such as IL-1, IL-6, IL-8, and TNF-α. The transcription factor NF-kB is a crucial regulator of the immune response and inflammation and regulates many cellular processes that are important in carcinogenesis, including transformation, proliferation, angiogenesis, and metastasis. Antiinflammatory plant C. trifolia L was shown to inhibit the activity of NF-B and several pro-inflammatory cytokine mediators. This study proved that the active compound from the plant's leaves, C. trifolia L has
potential as an inhibitor of NF-B and TNF-α.
Method: This study used a docking method with a grid box mimicking the bond between the receptor and the inhibitor control complex. Results: The bioactivity of Cayratria trifolia compounds as anti-inflammatory was shown in the inflammation parameters used, namely Interleukin 10 agonist, Interleukin agonist, Interleukin antagonist, Interleukin 6 antagonist, Interleukin 4 antagonist, Interleukin 2 agonist, Interleukin 1 antagonist, Interleukin 1b antagonist, Interleukin 10 antagonist, Interleukin 12 agonist, and Interleukin 1a antagonist. Interleukin 2 agonists showed the highest activity of all compounds. Piceid compounds showed high anti-inflammatory activity with interleukin 10 agonists, interleukin agonists, interleukin 6 antagonists, and interleukin 2 agonists. The compounds stilbenes, piceid, resveratrol, cyclopentadecane, and hentriacontane showed potency higher interleukin-6 inhibition than the other 22 compounds. These five compounds were continued for molecular docking analysis. The low bond energy is correlated with the number of bonds and the variety of interactions. The higher the number of bonds and the type of interaction, the lower the bond energy. The lower the bond energy, the stronger the interaction between the ligand and protein.
Conclusion: Based on the prediction of anti-inflammatory bioactivity, five potential compounds were identified, namely cyclopentadecane, resveratrol, stilbenes, piceid, and hentriacontane. The five compounds bind to NFkB on the active site of the binding site with DNA, and this inhibition causes DNA to be unable to restrain NFkB transcription factors, and transcription does not occur. This proves that the active compound from
the leaves of the plant C. trifolia L has potential as an inhibitor of NF-κB compounds. Inhibition of 6 compounds on TNF at the TNF receptor proves that the active compound from the leaves of the plant C. trifolia L has potential as a TNF-α inhibitor compound. The active ingredient Piceid exhibits predominant anti-inflammatory potential with lower binding energy and stronger interactions than other complexes.
Key words: H. Pylori, NFkB, TNF-α, C. trifolia L, In silico.
... Buah kersen dan daun lakum juga mengandungan squalen yang berpotensi mengatasi hiperlipidemia. Squalen dapat menghambat akumulasi lipid oleh sifat hipolipidemianya (Ragasa et al. 2014). Ekstrak dari keseluruhan tanaman lakum dapat memperbaiki gambaran histologi hati tikus yang diinduksi nitrobenzene pada keadaan nekrosis hati dan infiltrasi lipid di hati (Kumar et al. 2011),. ...
Daun lakum (Cayratia trifolia) dan buah kersen (Muntingia calabura) mengandung senyawa flavonoid, terpenoid, steroid dan kaya akan antioksidan. Beberapa senyawa antioksidan seperti squalene, nimbidin dan saponin berpotensi meningkatkan metabolisme HDL dalam tubuh sehingga dapat mengurangi timbunan lemak tubuh. Penelitian ini bertujuan untuk mengetahui perbedaan bobot badan dan bobot lemak abdominal tikus putih (Rattus norvegicus) strain wistar jantan hiperlipidemia setelah pemberian jus buah kersen dan ekstrak etanol daun lakum. Penelitian menggunakan Rancangan Acak Lengkap (RAL) yang teridiri atas 5 perlakuan dengan 4 kali ulangan, yaitu kelompok kontrol, kelompok pakan hiperlipid positif, kelompok pemberian pakan jus kersen, kelompok pemberian pakan ekstrak lakum dan kelompok pemberian simvastatin. Pakan hiperlipid diberikan selama enam minggu, dimulai dari tikus umur tiga bulan. Pengukuran variable bobot badan diukur tiap minggu dan bobot lemak abdominal di akhir penelitian. Data dianalisis dengan Analysis of Variance (ANOVA) yang dilanjutkan dengan Uji Duncan pada taraf kepercayaan 95%. Hasil penelitian menunjukan bahwa pemberian tambahan jus buah kersen dan ekstrak etanol daun lakum memberikan pengaruh yang signifikan pada bobot badan dan bobot lemak abdominal (p<0,05) Penelitian ini dapat disimpulkan bahwa pemberian jus buah kersen dan ekstrak etanol daun lakum pada tikus putih jantan hiperlipidemia tidak berpotensi menurunkan bobot badan, namun berpotensi menurunkan bobot lemak abdominal. Kata kunci : Cayratia trifolia, Muntingia calabura, antioksidan, bobot badan, bobot lemak abdominal
... Biji dan buahnya mengandung komponen sianogenik. Selain itu, aerial part dari tumbuhan ini memiliki kandungan kaempferol, mirisetin, kuersetin, epifriedelanol dan triterpen [26,27] (Gambar 1) ...
Galing (Cayratia trifolia L.) merupakan salah satu tumbuhan liar yang mayoritas terdapat di Asia Tenggara, termasuk Indonesia. Galing secara empiris telah banyak digunakan untuk mengobati berbagai macam penyakit. Hampir semua bagian dari tumbuhan galing dapat dimanfaatkan sebagai obat tradisional. Beberapa penelitian telah dilakukan untuk membuktikan aktivitas farmakologis dari tumbuhan galing. Oleh karena itu, tinjauan ini bertujuan untuk menyajikan informasi mengenai tumbuhan galing, baik secara biologi, fitokimia maupun aktivitas farmakologisnya.Kata kunci: Herbal, galing, Cayratia trifolia, obat tradisional, farmakologi
... Cayratia trifolia is commonly known as 'bush grape ', 'fox-grape', 'lakum' in Malaysia, 'kalit-kalit' in Philippines, 'galing-galing' in Indonesia, 'ta det' in Laos, 'thao kan khaao' in Vietnam and 'vualai' in Papua New Guinea (Gupta et al., 2012). Phytochemical investigation showed that the leaf of C. trifolia plants contained high levels of secondary metabolites such as kaempferol, myricetin, quercetin, triterpenes and epifriedelanol (Ragasa et al., 2014). The plant is widely used in traditional medicine for the treatment of wounding, anemia, stomachic diseases and diabetic. ...
By-products of the petroleum industry contaminate the environment, hence decreasing the soil fertility. However, in some contaminated areas, plants such as Cayratia trifolia continue to survive despite the harsh environment. Therefore in this study we aim to investigate the survival of C. trifolia at a petroleum refinery, PETRONAS Penapisan Melaka Sdn. Bhd (PPMSB). The main objective of this study was to identify and characterize candidate gene involved in the stress response. Differential display approach was performed on C. trifolia grown on soil and sludge, to identify up-regulated and down-regulated partial cDNAs. Out of 23 cDNAs checked, 18 genes were up-regulated genes while five were down-regulated. A partial gene (244 bp) represented by DEG7 fragment has a high similarity to the translocon. Blast2GO analyses was performed and showed DEG7 as a gene responsible for stress responses. A fragment of 1371 bp named as the CtSRG1 gene was succesfully amplified using the combination of RACE-PCR and degenerate PCR amplification. BlastN and BlastX analyses indicated that the CtSRG1 gene had higher similarity to translocon. CtSRG1 protein consists of Rieske and SRPBCC ligand-binding domains. The expression profile of CtSRG1 gene using qRT-PCR showed up-regulated expression when treated with Pb, NaCl and diesel but down-regulated with wounding treatment.
During this pandemic, people tend to consume herbal drinks to maintain endurance. One of the plants that people often use as a herbal drink is the lakum plant (cayratia folia). Lakum plants have various antioxidant and immunomodulatory activities. The main content of the lakum plant is flavonoids. The solvents most commonly used as solvents for lakum plant extracts are ethanol, water and methanol. In this study, primary data collection was carried out online, both in the form of national journals and international journals. The results obtained from several journals and other sources could determine
the immunomodulatory potential of vacuum plants. In this study, it was found that many of the benefits of these plants include anti-cancer, anti-inflammatory and others, of which a high level of antioxidant activity has an important role in each of the benefits of these plants.
A simple laboratory procedure for the isolation of pure cafestol and 16-O-methylcafestol together with β-sitosterol from coffee is disclosed. Cafestol and 16-O-methylcafestol have been exhaustively characterized through 1D and 2D 1H, 13C NMR, CD and X-ray diffraction. For the first time, the molecular structure of cafestol is reported and the assignment of the absolute configuration is unequivocally given by exploiting anomalous scattering of a brominated derivative.
Chemical investigation of the dichloromethane extracts of Cycas edentata led to the isolation of 9αH-isopimara-7,15-diene (1), β-sitosteryl fatty acid ester (2), and a mixture of β-sitosterol (3a) and stigmasterol (3b) from the bark; and 2 and a mixture of 3a and 3b from the sclerotesta. The structure of 1 was elucidated by extensive 1D and 2D NMR spectroscopy, while those of 2-3b were identified by comparison of their NMR data with those reported in the literature.
Chemical investigation of the dichloromethane extracts of Cycas edentata led to the isolation of 9αH-isopimara-7,15-diene (1), β-sitosteryl fatty acid ester (2), and a mixture of β-sitosterol (3a) and stigmasterol (3b) from the bark; and 2 and a mixture of 3a and 3b from the sclerotesta. The structure of 1 was elucidated by extensive 1D and 2D NMR spectroscopy, while those of 2-3b were identified by comparison of their NMR data with those reported in the literature.
Palm vitamin E, tocotrienols in particular, are known to exert great anti-cancer effects on a variety of cell types. In this study, the effects of palm vitamin E, carotenoids, squalene and coenzyme Q10 were studied on two human breast cancer cell lines. All compounds caused anti-proliferative effect in vitro but tocotrienols (compounds and isomers) were generally more potent. The results show that the anticancer effects of palm vitamin E were more pronounced when these were used on their own rather than in combination with other phytonutrients (carotenoids, squalene and coenzyme Q10). The palm phytonutrient complex, which contains all the tested phytonutrients did not appear to exert better antiproliferative effects compared to the individual compounds. Our results show that tocotrienols, as well as other phytonutrients (carotenoids, squalene and coenzyme Q10), have anti-proliferative effects on breast cancer cells but different and antagonistic mechanisms may be employed in combination.
Chemical investigation of the dichloromethane extracts of Coix lacryma-jobi afforded triglyceride (1) and β-sitosterol (2) from the grains; 1 and a mixture of 2 and stigmasterol (3) in a 4:3 ratio from the stems; and 1 and phytyl fatty acid ester (4) from the leaves. Their structures were identified by comparison of their 1H and/or 13C NMR data with those reported in the literature.
Objective
To assess the preliminary phytochemical constituents, free radical scavenging activities and HPTLC analysis of the whole plant of the ethanolic extract of Cayratia trifolia.Methods2, 2- diphenyl-1-picryl-hydrazyl, reducing power assay, superoxide radical scavenging, hydroxyl scavenging and nitric oxide scavenging assays were used in this study. The HPTLC analysis was also performed to confirm the presence of alkaloids and flavonoids in the ethanolic extract of Cayratia trifolia.ResultsThe preliminary phytochemical screening has shown the presence of alkaloid, flavonoids, tannins, saponins and phenolic compounds. The ethanolic extract of Cayratia trifolia possesses the free radical scavenging activities. The HPTLC analysis assessed that, the ethanolic extract of Cayratia trifolia has five alkaloid compounds and one flavonoid compounds.Conclusions
It is concluded that, the Cayratia trifolia contains natural source of antioxidants and the ethanolic extract of this plant possess a good free radical scavenging activity. In future, it can be used as a bioactive source of natural antioxidants and are potential natural resources for pharmacology of functional foods.
To investigate the mosquito larvicidal activity of Cayratia trifolia (L.) Domin (Vitaceae: Vitales) (C. trifolia) which is distributed in many parts of India with medicinal properties as vector control is facing threat due to the emergence of resistance to synthetic insecticides.
Young and mature leaves of C. trifolia were investigated for larvicidal activity against 3rd instars larvae of Culex quinquefasciatus in different seasons throughout the year. The active fractions were extracted using six different solvents in a non-polar to polar fashion viz petroleum-ether, benzene, chloroform: methanol (1:1 v/v), acetone, absolute alcohol and distilled water. Dose dependent mortality was recorded against each solvent extract. Determination of LD50 and LD90 were executed through log-probit analysis using the most bioactive fraction. The fluctuations in mortality were statistically co-related through ANOVA analyses concerning different seasons and types of leaves as random variables. Justification of larvicidal activity was established through student's t-test. Costing effects were evaluated on the non-target water fauna under laboratory conditions. Thin layer chromatographic techniques were performed for phytochemical analysis and categorization of chemical personality of the active fractions using the most effective solvent extract following standard methods.
Significant variations in mortality rate were noted with respect to the type of leaves (mature and senescence), concentration of leaf extract and between seasons. The water extract among all the solvent extracts was found to induce cent percent mortality at 50 mg/L in test mosquito species within 24 h with a LD50 and LD90 value of 10.70 mg/L and 27.64 mg/L respectively. No significant mortality was recorded in non-target water population. Chromatographic analyses of the water extract revealed the presence of steroids, triterpene glycosides, essential oil, phenolics and diterpenes as secondary phytochemicals.
Water extract of C. trifolia leaf promised as a cost effective and potent larvicidal agent against Culex quinquefasciatus.
The leaves of Broussonetia luzonicus afforded epitaraxerol (1), lupenone (2), squalene (3), β-carotene (4), vitamin K (5) and β-sitosterol (6), while the flowers yielded 2, 6, lupeol (7), betulin aldehyde fatty acid ester (8) and lupeol fatty acid ester (9). The compounds were isolated by silica gel chromatography and identified by NMR spectroscopy. Triterpenes 1, 2 and 8 were tested for cytotoxicity using the MTT assay. They did not exhibit cytotoxic effect against a human cancer cell line colon carcinoma (HCT 116). Results of the antimicrobial tests on 1, 2 and 8 indicated moderate antifungal activity against C. albicans and low antimicrobial activity against T. mentagrophytes, A. niger, S. aureus, E. coli, P. aeruginosa, and B. subtilis.
In a chemical study of taxonomically related Taxaceae plants of Yunnan Province, China, seven compounds, including a new amentoflavone biflavonoid, 2,3-dihydro-7,7' '-dimethoxyamentoflavone (1), were isolated from Amentotaxus yunnanensis, and 12 isolates were obtained from Torreya yunnanensis. From the latter plant, a new abietane diterpene, torreyayunnin (7), is reported for the first time. The known isolates from A. yunnanensis have been identified as sequoiaflavone (3), sotetsuflavone (4), 7,7' '-dimethoxyamentoflavone (5), lutein, beta-sitosterol, and sequoyitol. Amentoflavone (2), sotetsuflavone (4), sciadopitysin (6), 12-hydroxydehydroabietinol, meridinol, balanophonin, (+)-pinoresinol monomethyl ether, (+)-pinoresinol monomethyl ether glucoside, erythro-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[2-formyl-(E)-vinyl]-2- methoxyphenoxy]propane-1,3-diol, threo-1-(4-hydroxy-3-methoxyphenyl)-2- [4-[2-formyl-(E)-vinyl]-2-methoxyphenoxy] propane-1,3-diol, and (E)-2-butenedioic acid were identified as known isolates from T. yunnanensis. The presence of the amentoflavone biflavonoids (1, 3-5) in A. yunnanensis supports its placement in the Taxaceae. The occurrence of the biflavonoid sotetsuflavone (4) in both A. yunnanensis and T. yunnanensis suggests that these two genera are closely related. The identification and structural elucidation of these isolates were based on spectral data analysis including 1D and 2D NMR.
Objective
To evaluate the antiimplantation properties of the Pet ether extract of leaves of Cayratia trifolia Linn (C. trifolia) in rat by observing the implants after dosing the test extract.MaterialsPregnant females were separated and divided into thirteen groups each containing six animalsand were given Tween-80, 2% v/v. prepared extracts (PEECT) at the dose of 250 mg/kg and 500 mg/kg respectively. All the extracts and vehicle were administered orally to the animals once daily throughout 7 days of pregnancy. On 10th day of pregnancy, the animals were laparotomized under light ether anaesthesia and number of implants present in both the uterine horns was counted. Each pup was weighed and examined for gross defects.ResultAmong the two doses of PEECT, a dose of 500 mg/kg was found to be significant (P<0.01) and percentage inhibition of implantations in rats, at doses of 250 and 500 mg/kg, were found to be in PEECT 37.1, 56.7 respectively when compared with control. The highest activity was observed with the 500 mg/kg dose when the implantation were calculated about 10th day after the administration of the test extracts.Conclusions
It can be concluded from the study that the Petroleum ether extract of C. trifolia Linn. leaves have potent antiimplantation activity.
Plants have been used both in the prevention and cure of various diseases of humans and their pets. With the advent of human civilization, many systems of therapy have been developed primarily based on plants. Ayurveda, Homeopathy, Sidda, Unani, etc. are our traditional systems of medicines. The plant-based traditional medical systems continue to provide the primary health care to more than three-quarters of th e world's populace. In India, the use of plants for medicinal treatment dates back to 5000 years. It was officially recognized that 2500 plant species have medicinal value while over 6000 plants are estimated to be explored in traditional, folk and herbal medicine. An important prerequisite for proper utilization of raw materials of the country is the survey of its natural resources and the preparation of an inventory. It is necessary that we should have full knowledge regarding the occurrence, frequency, distribution and phenology of various plants for their proper utilization. The forests and arid regions of Rajasthan have great potentiality both from the economic and botanical points of view. This paper reviews the work done so far in the ethnobotany of Rajasthan.
An antitumour-promoting activity in two-stage carcinogenesis, is found in the methanol extract of the Carthami Flos (Carthamus tinctorius L.; Compositae), which is a traditional Chinese medicine and natural pigment of rouge additivies in certain Asian countries. From these active fractions, δ5- and δ7-sterol fractions were separated. The separation was examined for inhibitory activity against TPA-induced inflammatory ear oedema in mice. Stigmasterol (71% in the mixture) was the most abundant of 14 sterols identified in the δ5-sterol fraction. Schottenol (70% in the mixture) constituted the dominant sterol of the δ7-sterol fraction. Furthermore, stigmasterol markedly inhibited tumour promotion in two-stage carcinogenesis experiments.
Cancer remains as one of the most common cause of mortality worldwide. Cancer chemoprevention by natural products is well
accepted nowadays. Phytoserols are natural products, showing anticancer activity, besides other activities. The purpose of
this study was to examine the antitumor and antioxidant activity of stigmasterol, a phytosterol isolated from aerial parts
of Bacopa monnieri Linn. against Ehrlich Ascites Carcinoma (EAC) in swiss albino mice. The effect of stigmasterol on the growth of transplantable
murine tumor, life span of EAC bearing hosts, simultaneous alterations in the hematological profile, liver biochemical parameters
(lipid peroxidation, antioxidant enzymes) and histopthological studies of liver were examined. Stigmasterol decreased tumor
volume, packed cell volume and viable cell count, and increased mean survival time thereby increasing life span of EAC tumor
bearing mice. Hematological profile reverted to near normal levels in stigmasterol treated mice. Stigmasterol decreased the
levels of lipid peroxidation and increased the levels of glutathione, superoxide dismutase and catalase in the liver of EAC
bearing mice. Histopathological study of liver tissues showed that stigmasterol had significant protective effect against
EAC bearing mice, which corroborates the above findings. Lactate dehydrogenase (LDH) activity in ascitic fluid increased while
membrane microviscosity of the EAC cells decreased upon stigmasterol treatment indicating its effect in the membrane integrity
functions. The antitumor activity of stigmasterol might be mediated through the activation of protein phosphatase 2A by ceramide
causing apoptosis, as is shown by structurally similar phytosterol.
Keywords
Bacopa monnieri
–Stigmasterol–EAC–Antitumor effect