No full-text available
To read the full-text of this research,
you can request a copy directly from the authors.
Prenylated flavanones from leaves of Macaranga pleiostemona
Abstract
From the dichloromethane extract of leaves of Macaranga pleiostemona, four antibacterial prenylated flavanones were isolated. Their structures were elucidated by analysis of their spectral data. One, macarangaflavanone A, is a new compound, the remaining three are previously reported natural products. Macarangaflavanone B is clearly shown not to be euchrestaflavanone A. Euchrestaflavanone A and lespedezaflavanone B are revealed to be identical natural products.
... Plants have long been reported as important sources of bioactive molecules [4]. Plants of the Macaranga genus of the Euphorbiaceae are commonly used by traditional healers for the treatment of various diseases such as swellings, cuts, sores, diarrhea, cough, stomach-ache, hypertension, boils, furuncles, and bruises [5][6][7][8]. Macaranga occidentalis (Müll.Arg.) Müll.Arg. is used in the western region of Cameroon to treat stomach wash for pregnant women. ...
... Previous pharmacological studies of the crude extracts, fractions, and isolated compounds of the Macaranga genus possess a wide range of biological activities including anticancer, antioxidant, anti-inflammatory, and antimicrobial activities [5]. Chemical investigations of plants of this genus indicate that they constitute a rich source of isoprenylated, geranylated, and farnesylated flavonoids and stilbenes [7,8], terpenoids [9], coumarins [10], ellagic acid derivatives, and tannins [11]. As part of our long-term research work on bioactive natural product medicinal plants [12,13], we examined the leaves of M. occidentalis growing in Cameroon. ...
Citation: Kamso, V.F.K.; Simo Fotso, C.C.; Kanko Mbekou, I.M.; Tousssie, B.T.; Ndjakou Lenta, B.; Boyom, F.F.; Sewald, N.; Frese, M.; Ngadjui, B.T.; Wabo Fotso, G. Chemical Constituents of Macaranga occidentalis, Antimicrobial and Chemophenetic Studies. Molecules 2022, 27, 8820.
... S. alba is a genus of the family Lythraceae which comprises of about several species. It is present in some parts of the world, which include Indonesia, some parts of Africa, Australia, South East Asia and the Pacific islands [16][17][18][19][20][21][22]. The S. alba includes mangroves whose ecosystems are very productive, both ecologically and economically, which are located between land and sea environments. ...
... S. alba mangrove plants are known to be in the form of shrubs or trees and grow in places with optimum sunlight, wind and high salinity. S. alba show several bioactivity, which include antioxidant, antimalaria, antimicrobes and antiinflammatory [15][16][17][18][19][20]. ...
Objective: Sonneratia alba leaves were used by the community for traditional medicine to cure muscle pain, back pain, antioxidants, rheumatism, malaria, wounds, tuberculosis (TB) and as a spermicide. S. alba leaves extract was easy to damage because of the light exposure, change of pH, weather and a long period of storage time. The problem can be solved by coating the extract with a microencapsulation technique. The purpose of this research was to formulate the microcapsules of S. alba leaves extract with solvent evaporation technique using Ethocel 10 cP and Eudragit E100 as a matrix. Methods: S. alba leaves were extracted using ethanol 96%. This extract was dried by a rotary evaporator. The microencapsulation process of S. alba leaves extract was done by solvent evaporation technique (O/W: oil in water). The formula of S. alba leaves extract microcapsules was designed into six formulas (Eudragit E100: EA1, EA2, EA3 and Ethocel 10 cP: EB1, EB2, EB3). Microcapsules of S. alba leaves extract were characterized for particle size in terms of surface morphology by scanning electron microscope (SEM) and encapsulation efficiency. Antioxidant activity of the formulation have been evaluated by DPPH method. Physical characterization on microparticles was performed by conducting entrapment efficiency and SEM picture. Results: In this research, the microparticles containing S. alba extract has been developed by using ethyl cellulose (Ethocel 10 cP) and eudragit (Eudragit E100) as the polymer matrix. The results showed that a high concentration of polymer (Ethocel 10 cP and Eudragit E100) used in microencapsulation resulted in better S. alba leaves extract microcapsules in terms of physical characteristics. Particle size of microcapsules containing S. alba leaves extract were in the range of 0.701 to 1.163 μm. Encapsulation efficiency (% EE) was categorized as poor because the value were ≤ 80% to which 74.386% (EB3) and 75.248% (EA1). SEM picture of EA1 (Eudragit E100) revealed that the surface of microcapsule were rough and porous. When Ethocel 10 cP was used as a polymer, a smoother surface and less visible pores of microcapsule were obtained. The antioxidant ability of S. alba leaves extract microcapsule showed that IC50 values were 53.26 ppm. Conclusion: It can be concluded that microcapsules of S. alba leaves extract can be prepared by solvent evaporation technique using Eudragit E100 and Ethocel 10 cP as polymer. S. alba leaves has potent antioxidant activity either as an extract or after being formulated into microcapsules.
... Phytochemical study on the hydroalcoholic extract of Caatinga green propolis M. tenuiflora resulted in the isolation of sixteen flavonoids, including eleven flavonols 1-11, four flavanones 12-15, and one prenylated flavanone 16 (Fig. 2). From their NMR evidence (Supplementary material) and comparison with literature, these compounds were identified as santin (1) (Bautista et al., 2011), ermanin (2) (Castillo et al., 2015), quercetin 3-methyl ether (3) (Hong et al., 2015), viscosine (4) (Bautista et al., 2011), axillarin (5) (Turan et al., 2020), isokaempferide (6) (Escobar et al., 2009), kaempferide (7) (Hayashi et al., 1999), tamarixetin (8) (Venditti et al., 2016), kumatakenin (9) (Castillo et al., 2015), penduletin (10) (Mohammed et al., 2021), quercetagetin 3,6, 7-trimethyl ether (11) (Saleh et al., 2020), sakuranetin (12) (Cruz et al., 2016), eriodictyol 5-O-methyl ether (13) (Li et al., 2011), 5, 4 ′ -dihydroxy-6,7-dimethoxyflavanone (14) (Fernandez et al., 1988), eriodictyol-7,3 ′ -methyl ether (15) (Boukaabache et al., 2015), and macarangaflavanone B (16) (Schutz et al., 1995). ...
... (Fabaceae) (Boukaabache et al., 2015). Macarangaflavanone B (16) is a prenylated flavanone found in several medicinal plants, including Macaranga pleiostemona (Euphorbiaceae), Schoenus nigricans (Cyperaceae), and Lotus creticus (Fabaceae) (Schutz et al., 1995). However, ermanin (2), axillarin (5), eriodictyol 5-O-methyl ether (13), and 5,4 ′ -dihydroxy-6,7-dimethoxyflavanone (14) were detected in the family Fabaceae for the first time. ...
The phytochemical study of the hydroethanolic extract of green propolis produced by Apis mellifera in the
Northeastern Brazilian Caatinga from Mimosa tenuiflora led to the isolation of sixteen flavonoids, including
eleven flavonols 1–11, four flavanones 12–15, and one prenylated flavanone 16. It is the first time they were
isolated from the green propolis of Caatinga M. tenuiflora. Flavonols 2–3, and 5–11, and flavanones 14–16 were
first isolated from the genus Mimosa, as well as ermanin (2), axillarin (5), eriodictyol 5-Omethyl ether (13), and 5,4′-dihydroxy-6,7-dimethoxyflavanone (14) have never been observed in the family Fabaceae related materials before. HPLC analysis of the hydroalcoholic extracts confirmed M. tenuiflora as the primary botanical source of Caatinga green propolis. Chemotaxonomic significance is discussed in detail.
... Phytochemical research of the alcoholic extract of M. tenuiflora green propolis led to the isolation of six compounds 1-6 ( Figure 1). Their NMR spectroscopic data (Figures S1-S12) match well with previous reports, including two flavones quercetin 3methyl ether (1) and 3,3'-O-dimethylquercetin (2), and four flavanones eriodictyol 5-O-methyl ether (3), 5,4'-dihydroxy-6,7dimethoxyflavanone (4), licoflavanone (5), and macarangaflavanone B (6). [6][7][8][9][10][11] From previous studies, propolis from Asian and European regions contained a significant concentration of flavonoids, while Brazilian propolis was only accompanied by terpenoids and prenylated coumaric acids. [12] Our current result can be seen as new evidence for the presence of flavonoids in Brazilian propolis. ...
Phytochemical study of green propolis alcohol extract of Brazilian Caatinga Mimosa tenuiflora (Willd.) Poir resulted in the separation of six flavonoids, including quercetin 3‐methyl ether (1) and 3,3′‐O‐dimethylquercetin (2), and four flavanones eriodictyol 5‐O‐methyl ether (3), 5,4′‐dihydroxy‐6,7‐dimethoxyflavanone (4), licoflavanone (5), and macarangaflavanone B (6). All these metabolites were first isolated from green propolis and the genus Mimosa. Metabolites 3–4 also established chemotaxonomic significance since they had never been observed in the bean family Fabaceae. Flavones 1–2 showed strong antioxidative activity against DPPH (1,1‐diphenyl‐2‐picryl hydrazyl) radicals with IC50 values of 12.40 and 16.23 μg/mL, respectively. All six isolates showed anti‐inflammatory effects against NO (nitric oxide) production in LPS (lipopolysaccharide)‐stimulated Raw 264.7 cells, in which the activity of flavone 1 was better than the standard dexamethasone (IC50 13.35 μg/mL). Flavonoids 1–3 also strongly controlled the growth of the Gram‐positive bacteria Bacillus subtilis ATCC 6051, and Staphylococcus aureus ATCC 29213 with MIC values of 32–64 μg/mL. Six isolated flavonoids exhibited strong or moderate mosquito larvicidal activity against Aedes aegypti and Ae. albopictus fourth instar larvae with the 24 h LC50 values of 29.62–55.89 μg/mL. By in silico approach, compound 1 was a non‐toxic agent with an LD50 value of 5000 mg/kg.
... Therefore, microencapsulation technology can be used for obtaining bioactive products with desirable characteristics. Microencapsulation techniques of bioactive natural products are widely used in the food, pharmaceutical and cosmetic industries [11][12][13][14][15]. Techniques for the incorporation of bioactive compound within polymer matrices have indicated a good alternative for the improvement of the functionality of medicinal [16][17][18][19][20][21][22]. ...
Objective: Casticin (Vitexicarpin) has shown immunoregulatory, antitumor, cytotoxicity, anti-inflammatory and analgesic properties. Application of the valuable bioactive compounds can be limited by their unpleasant taste, low bioavailability, volatilization of active compounds, sensitivity to the temperature, oxidation and UV light, as well as in vivo instability. The problem can be solved by coating the Casticin with a microencapsulation technique. The purpose of this research was to formulate the microcapsules of Casticin with solvent evaporation technique using Ethocel 10 cP. Methods: The microencapsulation process of Casticin was done by solvent evaporation technique (O/W: oil in water). The formula of Casticin microcapsules were designed into three formulas (Ethocel 10 cP: 10%, 15% and 20%). Microcapsules of Casticin were characterized for particle size, in terms of surface morphology by scanning electron microscope (SEM), encapsulation efficiency and release test. Results: In this research, the micoparticles containing Casticin has been developed by using ethyl cellulose (Ethocel 10 cP) as the polymer matrix. The results showed that high concentration of polymer (Ethocel 10 cP) used in microencapsulation resulted in better Casticin microcapsules in terms of physical characteristics. Particle size of microcapsules containing Casticin were in the range of 42.51 to 61.47 μm. Encapsulation efficiency (% EE) was categorized as good because the value were ≥ 80% to, which 91.57% to 96.24%. SEM picture of Casticin microcapsules revealed that the surface of microcapsule were a smooth surface and no pores of microcapsule were obtained. When Eudragit E100 used as a polymer, a rough and porous surface of microcapsule were obtained. Conclusion: It can be concluded that microcapsules of Casticin can be prepared by solvent evaporation method with a single emulsion system (O/W) using Ethocel 10 cP as polymer. Characterization of the microcapsules revealed that ethyl cellulose used on this method is applicable to produce microcapsules which stable in physical properties. A higher polymer concentration led to a more viscous solution, which delayed the polymer precipitation and resulted in a less porous polymer matrix with a slower drug release.
... Macaranga gigantea plants show several bioactivity which include antitumor, anticancer, antimalaria, antimicrobes, cyclooxygenase and antioxidant. [15][16][17][18][19][20] The plant is also known to have active phytochemicals constituents, especially on its leaves. 7,21 Solvent evaporation method has been widely and extensively used to prepare polymeric microparticles containing different drugs and in the development of modified release systems. ...
Introduction: The aim of this research was to formulate the microcapsules of Macaranga gigantea leaves extract with solvent evaporation method using Ethocel 10 cP and Eudragit E100 as matrix. Methods: M. gigantea leaves were extracted using ethanol 96%. This extract was dried by rotary evaporator. The microencapsulation process of M. gigantea leaves extract was conducted by solvent evaporation method (O/W: oil in water). The formula of M. gigantea leaves extract microcapsules were designed into six formulas (Eudragit E100: FA1, FA2, FA3 and Ethocel 10 cP: FB1, FB2, FB3). Microcapsules of M. gigantea leaves extract were characterized for particle size, in terms of surface morphology by scanning electron microscope (SEM) and encapsulation efficiency. Antioxidant activity of the formulation have been evaluated by DPPH method. Physical characterization on microparticles were performed by conducting entrapment efficiency and SEM picture. Results: In this research, the micoparticles containing M. gigantea extract has been developed by using ethyl cellulose (Ethocel 10 cP ) and eudragit (Eudragit E100) as polymer matrix. The results showed that high concentration of polymer (Ethocel 10 cP and Eudragit E100) used in microencapsulation resulted in better M. gigantea leaves extract microcapsules in terms of physical characteristics. Particle size of microcapsules containing M. gigantea leaves extract were in the range of 3.564 to 5.887 μm. Encapsulation efficiency (% EE) was categorized as good because the value were ≥ 80% to which 85.978% (FA3) and 88.992% (FB3). SEM picture of FA3 (Eudragit E100) revealed that the surface of microcapsule were rough and porous. When Ethocel 10 cP used as polymer, a smoother surface and less visible pores of microcapsule were obtained. The antioxidant ability of M. gigantea leaves extract microcapsule showed that IC50 values was 64.51 ppm. Conclusion: It can be concluded that microcapsules of M. gigantea leaves extract can be prepared by solvent evaporation method by using Eudragit E100 and Ethocel 10 cP as polymer matrix. M. gigantea leaves has potent antioxidant activity either as extract or after formulated into microcapsules.
... Present study indicated that ethanolic extract of M. gigantea leaves potent to be antimalarial agents. 18,19 The data was in line with previous investigation on this genus which showed that its crude extracts and compounds offered bioactivity including anticancer, 23,24 antioxidant, 25 antmicrobial, 26 anti-inflammatory 27 and other different types of biological activities. 28 In the acute toxicity study, a maximum dose of 21 g/kg to either male and female mice has been determined. ...
Introduction: This research main goal is to study the antiplasmodial activity of Macaranga gigantea leaf ethanolic extract and its major components on malaria parasites using ex vivo model. Methods: This study was conducted by extraction of M. gigantea leaves using ethanol and isolation of its major constituent. The extract and isolate were tested ex vivo on Balb-C mice’s blood after i.p. administration of Plasmodium berghei strain ANKA. Antiplasmodial activity was observed from mice blood treated by various concentration of either extract or isolate and the parasitaemia percentage were determined by calculating infected blood cell after 24 h of the treatment. It is expressed as decreased of parasitaemia levels and percent of inhibition. Qualitative analysis of active fraction were tested by HPLC method. Chemical structure of isolate were characterized by using UV, IR, ¹H-NMR, ¹³C-NMR and MS spectrophotometry. Results: Ex vivo antiplasmodial study gave the percent inhibition as much as 92.1; 85.7; 64.1; 41.5 and 21.7% at extract concentrations of 300, 100, 30, 10 and 3 μg/ mL respectively. The IC50 values of the extract was 27.1 µg/ml. With respect to the percent of inhibition, at the same concentration, the isolate showed activity as much as 70.2; 62.5; 39.1; 21.7 and 10.8%. The IC50 value of the isolate was 60.2 µg/ml. At the same concentration with extract and Isolate, Pyrimethamine as positive control gave percent inhibition of 94; 87.5; 44.8; 15.; and 12%, with IC50 of 31.4 µg/ml. The results showed that major constituent of M. gigantea leaves is flavonoid. HPLC analysis using a photo diode-array detector showed that the active fraction have same retention time with that of apigenin as standard. Based on instrumental analysis data and compared with literature, a flavonoid derivate known as apigenin can be said has been isolated. Conclusion: It can be concluded that either M. gigantea leaves extract or isolated active constituent known as apigenin have potent antiplasmodial property.
... A phytochemical review of the literatures indicates the genus Macaranga to be a rich source of the isoprenylated, geranylated and farnesylated flavonoids [14][15][16][17] and stilbenes. [17][18][19] Furthermore more classes of secondary metabolites like terpenes, 14,15,20 tannins, 21-23 coumarins 24,25 and other types of compounds [26][27][28] are known to be isolated from different species of the genus Macaranga. ...
Macaranga denticulata (Blume) Müll.Arg. (family Euphorbiaceae) is an evergreen tree and a
common pioneer species in moist open and secondary forest. It is commonly known as
Kharpa in Mizoram. Traditionally, the species of Macaranga are used in the treatment of
swelling, cuts, sores, boils and bruises. Preliminary phytochemical screening and evaluation of
in vitro antioxidant activity were carried out on the methanolic extract obtained from the bark
of M. denticulata. The presence of alkaloids, tannins, flavonoids, saponins, steroids and triterpenoids
was indicated by the tests conducted. The in vitro antioxidant activity was evaluated
using 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, reducing power and
hydrogen peroxide radical scavenging activity. Ascorbic acid and butylated hydroxytoluene
(BHT) were used as reference standards. The methanolic extract of the plant shows a strong
antioxidant activity comparable to that of the reference standards.
... A phytochemical review of the literatures indicates the genus Macaranga to be a rich source of the isoprenylated, geranylated and farnesylated flavonoids [14][15][16][17] and stilbenes. [17][18][19] Furthermore more classes of secondary metabolites like terpenes, 14,15,20 tannins, 21-23 coumarins 24,25 and other types of compounds [26][27][28] are known to be isolated from different species of the genus Macaranga. ...
... Macaranga pustulata King ex Hook, small trees or shrubs, are widely distributed in secondary forests, mountain slopes, and valleys in Tibet and Yunnan Provinces in China [7]. Several earlier phytochemical investigations of this genus plants lead to the isolation of diterpenoids [8][9][10][11], triterpenoids [10], flavonoids [2,[12][13][14][15][16][17][18], bergenins [19], and stilbenes [20][21][22]. As part of our ongoing search for novel or active chemical constituents from the Euphorbiaceae family plants, three new cembranoids (1−3), together with 5 known analogues (4−8), were isolated from the twigs of M. pustulata King ex Hook. ...
... Thioflavanones are one of the most important classes of the flavanoids that are found almost exclusively in plants. 1 Flavonoids have been reported to possess a broad range of biological activities such as anti-hypertensive, 2 anti-oxidant, 3 anti-malarial, 4 anti-HIV 5 anti-bacterial 6 anti-tumor, 7 and radio protective agents. 8 Some of the flavonoids have the ability to act as selective estrogen receptor modulators. ...
Thioflavanones are prevalent heterocyclic structural units in pharmaceutical and biologically active compound (Scheme1). In this paper, the synthesis of 2-phenylthiochroman-4-ones and 2-phenyl-4H-1-benzothiopyran-4-one labeled with carboxyl-14 is demonstrated.
... and -118.8 kJ/mol, respectively). Two diprenylated flavanones, euchrestaflavanone A from Macaranga pleiostemona [54] and flemiflavanone D from Flemingia stricta [55] showed notably strong docking with DENV NS2B-NS3 protease (Table 1). These compounds had shown antibacterial activity, but to our knowledge have not been screened for anti-dengue activity. ...
A virtual screening analysis of our library of phytochemical structures with dengue virus protein targets has been carried out using a molecular docking approach. A total of 2194 plant-derived secondary metabolites have been docked. This molecule set was comprised of 290 alkaloids (68 indole alkaloids, 153 isoquinoline alkaloids, 5 quinoline alkaloids, 13 piperidine alkaloids, 14 steroidal alkaloids, and 37 miscellaneous alkaloids), 678 terpenoids (47 monoterpenoids, 169 sesquiterpenoids, 265 diterpenoids, 81 steroids, and 96 triterpenoids), 20 aurones, 81 chalcones, 349 flavonoids, 120 isoflavonoids, 74 lignans, 58 stilbenoids, 169 miscellaneous polyphenolic compounds, 100 coumarins, 28 xanthones, 67 quinones, and 160 miscellaneous phytochemicals. Dengue virus protein targets examined included dengue virus protease (NS2B-NS3pro), helicase (NS3 helicase), methyltransferase (MTase), RNA-dependent RNA polymerase (RdRp), and the dengue virus envelope protein. Polyphenolic compounds, flavonoids, chalcones, and other phenolics were the most numerous of the strongly docking ligands for dengue virus protein targets.
... Compound 2 (20 mg) was purified from F4 by column chromathography with CHCl 3 , acetone and MeOH eluents to obtained a pure compound. Antioxidant activity [14]. Antioxidant analysis was conducted using "DPPH free scavenging activity" method with a slight modification. ...
Two flavonoid compounds, 5,7,3′,4′-tetrahydroxy-6-geranylflavonol (1) and kaempferol 7-O-β-glucose (2) have been isolated from the leaves of Macaranga hispida (Blume), Mull.Arg. Isolation and purification were conducted by chromatography methods and chemical structure characterization was carried out by spectroscopic methods. The 5,7,3′,4′-tetrahydrxyi-6-geranyl flavonol (1) and kaempferol 7-O-glucose (2) had moderate cytotoxic activity against murine leukemia P-388 cell lines with IC50 value of 0.22 and 101.5 μg/mL, respectively. The IC50 for antioxidant activities of (1) and (2) were 2.83 and 13.95 μg/mL, respectively. The LC50 of (1) and (2) from BSLT were 350 and >1000 μg/mL, respectively.
... There are more than 308 species of Macaranga, wide-spread from Africa and west region of Madagascar until tropical region of Asia, North Australia and east region of Pacific Islands (Blattner, 2001). Macaranga genus also known as a sources of terpenoid (Hui, 1971)] and phenolic (flavonoid) (Jang, 2002;Schutz, 1995;Sutthivaiyakit, 2002;Yoder, 2007) compounds which have biological activity as antioxidant (Phommart, 2005) and anticancer (cytotoxicity) (Yoder, 2007). Macarangin, a geranylated flavonoid compound is one of the flavonoid typical compounds contained in Macaranga genus, and have been isolated from M. vedeliana (Hnawia, 1990) and M. denticulate (Sutthivaiyakit, 2002). ...
Macaranga known locally as mahang-mahangan has uniquely ecological function, and also became a part of traditional medicine in Indonesia. Macaranga genus also known as a sources of terpenoid and phenolic (flavonoid) compounds which have biological activity as antioxidant and anticancer (cytotoxicity).There are few phytochemical investigations have been done on M. gigantifolia species. As a part of our continuing research of isolation anticancer compound from natural product, a geranylated flavonoid compound (macarangin) has been isolated from ethyl acetate fraction of Macaranga gigantifolia leaves using chromatography methods. The isolated compund (isolat MG) was elucidated to gain the chemical structure based on spectroscopic data (LC-MS and FT-NMR). Cytotoxicity test of this compound was tested against MCF 7 cell lines, showed that macarangin has a potential activity with IC 50 value 119.12μg/mL.
... Their radical scavenging ability is well reported in literature. The screening of F. exasperata fractions indicated they have activity against Gram-positive bacteria only (Table 4. Rhoca et al., 1995;Shutz et al., 1995 andVaughn, 1995). The isolated compounds' antibacterial activity was weak unlike the activity reported in literature for both quercetin and apigenin aglycones. ...
Background:
Ficus exasperata Vahl-Holl (Moraceae) leaves are used for infectious and inflammatory conditions in many West African Countries. However, there is need for more phytochemical studies to justify the ethnomedicinal uses of the plant.
Material and methods:
The crude 50% aqueous ethanolic extract of the leaves was partitioned successively between water and; n-hexane, ethyl acetate and n-butanol. The fractions were subjected to antimicrobial activity using agar diffusion test. n-Butanol fraction, which showed both antimicrobial and radical scavenging activities was subjected to repeated chromatographic fractionation on both silica and Sephadex LH-20 columns. Each stage of the purification was monitored by thin layer chromatographic diphenylpicryl hydrazyl autographic assay. Three compounds were isolated. The structures of the compounds were elucidated using spectroscopic methods, shift reagent studies, acid hydrolysis, and by comparison with literature data.
Results:
The compounds were identified as apigenin C-8 glucoside (1), isoquercitrin-6-O-4-hydroxybenzoate (2) and quercetin-3-O-β-rhamnoside (3). The solvent fractions and isolated compounds were found to inhibit the growth of Gram +ve organisms only.
Conclusion:
These flavonoid glycosides are being reported in this plant species for the first time. Their weak in vitro antimicrobial activity suggest the flavonoids may be acting as pro-drug. The radical scavenging activity of the compounds may justify some of the ethnomedicinal uses of the plant as free radicals are implicated in the aetiology of many inflammatory diseases.
... In recent year extensive studies have been conducted for the search of antibacterial properties in different species of plant. Organic extracts of various medicinal plants containing flavonoids have been reported to show antimicrobial activity [27][28][29][30][31][32][33] . The antibacterial activities of isofavonoids and flavonoids, and glycosides of luteolin and apigenin have also been reported 34 . ...
Bryophytes, a small group of lower plant phylogenetically placed between algae and the vascular plants comprise of hornworts, liverworts and mosses. They are the second largest group of land plants and extremely rich in a variety of biologically active compounds viz. terpenoids, phenols, glycosides and fatty acids. This small slow growing group of plants is stockroom of naturally occurring materials and have been investigated for the antimicrobial, antioxidant, anti-inflammatory, anti-venomous and anti-leukemic activity. In the recent years bryophytes has emerged as a potential biopharming tool for production of complex biopharmaceutiticals. Even though bryophytes could be used in medicine, the use of bryophytes for applied research with implications for human health is still not fully explored. Investigations are hindered commonly because of minute size and difficulties in identifying diverse species of bryophytes. In the present review we focused on therapeutic uses of bryophytes in detail that will widely open the door for the use of different bryophytes in plant biotechnology and to meet the demand of novel drug discovery.
... The structures of the known compounds were identified by comparison of their spectral data with literature values. [4][5][6][7] Schizolaenone A (1): yellow amorphous solid; [R]D +2.7° (c 0.44, MeOH); UV (MeOH) λmax (log ) 224 (2.25) nm, 293 (2.10) nm; IR νmax 2966,2920,2853,1633,1597,1447,1149,1085,1063,819 (2) 1 1 4′-O-methylbonannione A (3) 1 7 nymphaeol A (4) 5.5 bonannione A (5) 1 2 macarangaflavanone B (6) 1 6 bonanniol A (7) 2 5 ...
Bioassay-guided fractionation of an ethanol extract of a Madagascar collection of Schizolaena hystrix afforded three new flavanones, schizolaenone A (1), schizolaenone B (2), and 4'-O-methylbonannione A (3), as well as three known flavanones, nymphaeol A, bonannione A, and macarangaflavanone B, and the flavanol bonanniol A. The structures of compounds 1-3 were determined by various one- and two-dimensional NMR techniques. All of the isolates were tested for cytotoxicity against the A2780 human ovarian cancer cell line. Nymphaeol A (IC(50) = 5.5 microg/mL) exhibited the greatest cytotoxicity, while the other flavanones were found to be only weakly active.
Sulfated tungstate efficiently catalyzes the cyclodehydration of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones to flavones under solvent-free conditions. Utilization of conventional heating, simple reaction conditions, short reaction time, ease of product isolation and purification makes this manipulation very interesting from an economic and environmental perspective. Under these conditions, twelve examples were obtained with good yields (85-94%).
Macaranga merupakan salah satu genus terbesar dari famili Euphorbiaceae yang terdiri dari 300 spesies dengan nama lokal mahang-mahangan. Tumbuhan Macaranga tersebar luas di wilayah Afrika dan Madagaskar di bagian barat hingga ke wilayah tropis Asia, Australia utara dan kepulauan Pasifik. Di Indonesia tumbuhan Macaranga tersebar di beberapa daerah yaitu daerah Papua, Maluku, Sulawesi, Kalimantan, Sumatera, Bangka, dan Jawa. Kajian fitokimia beberapa spesies Macaranga menunjukan adanya kelompok senyawa fenolik yaitu turunan flavonoid dan stilben, serta turunan terpenoid. Senyawa turunan fenolik tersebut memiliki keunikan dari struktur molekulnya, yaitu adanya subtituen tambahan dari metabolit terpenoid yaitu prenil (C5), geranil (C10), farnesil (C15), dan geranilgeranil (C20). Pada penelitian ini telah dilakukan isolasi metabolit sekunder dari daun M. involucrata (Roxb.) Baill dengan metode maserasi menggunakan pelarut aseton, kemudian dilanjutkan pemisahan dan pemurnian dengan menggunakan kromatografi cair vakum dan kromatografi radial untuk mendapatkan senyawa murni. Penentuan struktur dilakukan berdasarkan analisis data spektrum NMR 1D (1H-NMR dan13C-NMR), NMR 2D (NOESY, TOCSY, HSQC, dan HMBC), dan spektrum massa (MS). Berdasarkan metodologi tersebut, dua senyawa turunan flavon yaitu 5,7,4’-trihidroksi-3’(3-metilbut-2-enil)-3-metoksiflavon (1) dan makarangin (2), telah berhasil diisolasi dari tumbuhan ini. Berdasarkan hasil penelitian tersebut menunjukan daun M. involucrata (Roxb.) Baill yang berasal dari Kabupaten Buton Tengah, Sulawesi Tenggara menghasilkan senyawa fenolik turunan flavonoid.
Kata kunci: Euphorbiaceae, Macaranga involucrata (Roxb.) Baill, flavon.
Macaranga is one of the largest genera of the family Euphorbiaceae comprising 300 species with local name “mahang-mahangan”. Macaranga is widespread in the region of Africa and the west of Madagascar to the tropical regions of Asia, northern Australia, and the Pacific islands. In Indonesia Macaranga spread in several areas: Papua, Maluku, Sulawesi, Kalimantan, Sumatra, Bangka, and Java. Phytochemical studies showed the presence of several phenolic compounds such as flavonoids and stilbene derivatives. The phenolic compounds have a unique molecular structure with the addition of some substituents such as prenyl (C5), geranyl (C10), farnesyl (C15), and geranylgeranyl (C20). This research has been conducted on the isolation of secondary metabolites from the leaves of M. involucrata (Roxb.) Baill by maceration method using acetone, followed by separation and purification by using liquid vacuum chromatography and radial chromatography to obtain pure compounds. Determination of the structure is based on data analysis of 1D NMR spectrum (1H-NMR and 13C-NMR), 2D NMR (1H-1HCOSY, NOESY, TOCSY, HSQC, and HMBC), and mass spectra (MS). Based on this methodology, two flavone derivatives 5,7,4'-trihydroxy-3'(3-methylbut-2-enyl)-3-methoxy flavone (1) and macarangin (2), have been isolated from this plant. Based on these results showed that leaf of M. involucrata (Roxb.) Baill from Central Buton, Southeast Sulawesi produces phenolic compounds from flavonoid derivatives.
Keywords: Euphorbiaceae, Macaranga involucrata (Roxb.) Baill, flavone.
Stilbene analogues have shown remarkable structural diversity constituting simple or tangled structures, which have attracted the synthetic as well as the medicinal chemistry communities. Schweinfurthins are a family of prenylated/geranylated/farnesylated stilbenes that are isolated from an African plant belonging to the Macaranga species. These compounds have displayed potency towards central nervous system, renal and breast cancer cell lines. Specifically, these compounds have been found to be potent and selective inhibitors of cell growth in the National Cancer Institute's 60 cell-line screen. In this review article, we described the isolation, synthesis, and biochemical properties of schweinfurthins.
This document is part of Subvolume D4 'Chemical Shifts and Coupling Constants for Carbon-13. Part 4: Natural Products' of Volume 35 'Nuclear Magnetic Resonance Data' of Landolt-Börnstein Group III: 'Condensed Matter'. It contains the chemical shifts, coupling constants, structural diagram and solvent of C25H28O5 Contained elements: C-H-O
This document is part of Subvolume D4 'Chemical Shifts and Coupling Constants for Carbon-13. Part 4: Natural Products' of Volume 35 'Nuclear Magnetic Resonance Data' of Landolt-Börnstein Group III: 'Condensed Matter'. It contains the chemical shifts, coupling constants, structural diagram and solvent of C25H28O5 Contained elements: C-H-O
This document is part of Subvolume D4 'Chemical Shifts and Coupling Constants for Carbon-13. Part 4: Natural Products' of Volume 35 'Nuclear Magnetic Resonance Data' of Landolt-Börnstein Group III: 'Condensed Matter'. It contains the chemical shifts, coupling constants, structural diagram and solvent of C25H28O5 Contained elements: C-H-O
Four novel prenylflavonols, macaranones A-D (1-4), were isolated from the leaves of Macaranga sampsonii. Their structures were elucidated on the basis of spectroscopic data. Macaranones C (3) and D (4) represent first two examples of flavonols having an unusual peltogynoid skeleton which is formed from a 2'-geranylflavonol by cyclization between 3-OH and C-1 '' of the 2'-geranyl substituent of the flavonol. Compounds 1-4 were evaluated for the cytotoxicity against several human cancer cell lines.
A simple and highly efficient approach for the synthesis of gamma-Benzopyranones and 3,4-Dihydropyrimidin- 2(1H)-ones/thiones using ammonium acetate as a promoter under thermal as well as microwave irradiation using solvent-free conditions has been demonstrated.
Objective: To study the chemical constituents in the roots of Flemingia macrophylla. Methods: To separate and purify compounds by column chromatography and TLC, and to determine their chemical structures by their physical characters and spectral data. Results: Eleven compounds were purified from the extraction in the roots of F. macrophylla, among them four are isoflavones, three are flavanones, and one is flavanol. They are genistein (I), orobol (II), 5, 7, 4′-trihydroxyisoflavone-7-O-β-D-glucopyranoside (III), 5, 7, 4′-trihydroxy-8, 3′-diprenylflavanone (IV), 5, 7, 4′-trihydroxy-6-prenylisoflavone (V), flemichin D (VI), lespedezaflavanone A(VII), ouratea-catechin (VIII), 3, 4, 5-trimethoxy-benzene-O-β-D-glucopyranoside (IX), stigmasterol-3-O-β-D-glucopyranoside (X), and stigmasterol (XI). Conclusion: Compounds III-V, and VII-XI are found from this plant for the first time. All the compounds are found from the roots of this plant for the first time. The active components, genistein and its isoflavone analogs, are main constituents in the roots of F. macrophylla.
2.3-Dihvdro-1-tosylquinolin-4(1H)-one derivatives, azaisoflavanones. have been synthesized efficiently via a gold-catalvzed annulation of 2-tosylaininobenzaldehyde and alkynes. This annulation offers the synthesis of a range of potentially bioactive molecules.
The genus Macaranga Thou. (Euphorbiaceae) comprises of about 300 species that are native mainly to the tropics of Africa, Asia, Australia and the Pacific regions. Plants of this genus have a long history of use in traditional medicine to treat cuts, swellings, boils, bruises and sores. Phytochemical work on this genus has reported over 190 secondary metabolites being isolated mainly from the leave extracts of different species of this genus. The isolated compounds included stilbenes, flavonoids, coumarins, terpenoids, tannins and other types of compounds. The crude extracts and isolated compounds showed a wide spectrum of pharmacological activities including anti-cancer, anti-inflammatory, anti-oxidant, anti-microbial and anti-plasmodial activities. The aim of this review is to coherently document the valuable but scattered reports on the phytochemistry and pharmacology of medicinal plants of the genus Macaranga collected from different parts of the global.
Key words: Macaranga species, Euphorbiaceae, phytochemistry, pharmacology.
Three dihydroflavonol derivatives, macarecurvatin A (1), macarecurvatin B (2), and 6,8-diisoprenylaromadendrin (3) have been isolated from the leaves of Macaranga recurvata. The structures of these compounds were determined based on UV, IR, HRESIMS, 1D and 2D NMR data. All of compound isolated were evaluated for their inhibitory effect on scavenging DPPH radical and their growth inhibition on MCF7, and tamoxifen-resistant MCF7 (MCF7/TAMR) breast cancer cell showed high antioxidant and high cytotoxic activities.
Flavonoids are well known as antibacterial agents against a wide range of pathogenic microorganism. With increasing prevalence of untreatable infections induced by antibiotic resistance bacteria, flavonoids have attracted much interest because of the potential to be substitutes for antibiotics. In this review, the structure-relationship of flavonoids as antibacterial agents is summarized, and the recent advancements on the antibacterial mechanisms of flavonoids are also discussed. It is concluded that hydroxyls at special sites on the aromatic rings of flavonoids improve the activity. However, the methylation of active hydroxyl groups generally decreases the activity. Besides, the lipopholicity of ring A is vital for the activity of chalcones. Hydrophobic substituents such as prenyl groups, alkylamino chains, alkyl chains, and nitrogen or oxygen containing heterocyclic moieties usually enhance the activity for all the flavonoids. The proposed antibacterial mechanisms of flavonoids are as follows: inhibition of nucleic acid synthesis, inhibition of cytoplasmic membrane function, inhibition of energy metabolism, inhibition of the attachment and biofilm formation, inhibition of the porin on the cell membrane, alteration of the membrane permeability, and attenuation of the pathogenicity.
An efficient and eco-friendly synthesis of flavones, promoted by naturally occurring acids, via cyclodehydration of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones using conventional and microwave heating under solvent-free condition is described.
This document is part of Subvolume C3 `Chemical Shifts and Coupling
Constants for Hydrogen-1. Part 3: Natural Products' of Volume 35
`Nuclear Magnetic Resonance (NMR) Data' of Landolt-Börnstein -
Group III Condensed Matter.
This document is part of Subvolume C3 `Chemical Shifts and Coupling
Constants for Hydrogen-1. Part 3: Natural Products' of Volume 35
`Nuclear Magnetic Resonance (NMR) Data' of Landolt-Börnstein -
Group III Condensed Matter.
This document is part of Subvolume C3 `Chemical Shifts and Coupling
Constants for Hydrogen-1. Part 3: Natural Products' of Volume 35
`Nuclear Magnetic Resonance (NMR) Data' of Landolt-Börnstein -
Group III Condensed Matter.
Two new prenylated flavanones, mundulea flavanones A and B, were isolated from the chloroform extract of stembark of Mundulea suberosa along with the previously reported compounds munetone, mundulone and mundulea lactone. Their structures were established by spectral data as 4′-hydroxyisoderricin and 7-methyl-4′-hydroxyglabranin
For Abstract see ChemInform Abstract in Full Text.
Two new prenylflavanones, tanariflavanones A (1), and B (2), and one known compound, (-)-nymphaeol-C (3), were isolated from the fallen leaves of Macaranga tanarius. Compounds 1 and 2 showed inhibition of radicle growth of lettuce seedlings at 200 ppm. Their structures were elucidated primarily by NMR, circular dichroism, and mass spectroscopic methods.
A new prenylated stilbene, mappain (1), was isolated from leaves of Macaranga mappa by bioassay-guided fractionation. The structure was established by application of spectroscopic methods. Mappain is cytotoxic but it appears to be a poor substrate for P-glycoprotein-mediated transport because it is equally potent and effective against the drug-sensitive SK-OV-3 and drug-resistant SKVLB-1 ovarian cancer cell lines, exhibiting an IC50 value of 1.3 muM in both cases.
The title compounds, 4'-0-geranylisoliquiritigenin and 4'-0-geranylnaringenin isolated from Millettia ferruginea and Borania coerulescens respectively, were first synthesized starting from geranyl bromide, 4-hydroxybenzaldehyde and O-hydroxy acetophenones by the condensation reaction and demethoxymethylation as key steps.
Gold-catalyzed reactions of C–H bonds, with a particular emphasis on C–C, C–O, and C–N bond formations, are reviewed.Figure optionsView in workspaceDownload full-size imageDownload as PowerPoint slide
An O-methylated analogue of macarangin (1) and denticulaflavonol (2) which possesses a diterpene substituent have been isolated along with other compounds from the leaves of Macaranga denticulata. Their detailed 1D and 2D spectral analysis are reported. The radical scavenging properties of compounds 3–5 were evaluated. Among the compounds tested, 4 showed a pronounced antioxidant activity (IC50 0.032±0.001mM).
Cyclization of a variety of chalcones to flavanones catalyzed by 1 mol% phosphomolybdic acid (PMA) supported on silica as a mild, efficient, and reusable catalyst was carried out in high yields. PMA-SiO2 is an efficient, inexpensive, and green catalyst which gave high conversion yields and could be recycled up to three times without significant loss in activity.
Graphical abstract
Bioassay-guided fractionation of an extract of leaves of Macaranga kurzii yielded four new compounds, a stilbene (furanokurzin, 1) and three flavonoids (macakurzin A-C, 2-4). Nine known compounds were also isolated (5-13). Their structures were determined by spectroscopic analyses including MS and 2D NMR. The isolates were all evaluated for acetylcholinesterase inhibitory activity. Compound 6 (trans-3,5-dimethoxystilbene) exhibited the greatest activity (IC(50) 9 μM). Cytotoxic evaluation against KB cells showed that compound 7 had an IC(50) of 4 μM, followed by 11 (IC(50) 10 μM) and 3 (IC(50) 13 μM).
Two new flavanones have been isolated from the root bark of Lespedeza davidii and their structures established as 6,8-di-γ,γ-dimethylallyl-4′-methyoxy-5,7,2′-trihydroxy-(2S)-flavanone and 8,3′-di-γ,γ-dimethylallyl-5,7,4′-trihydroxy-(2S)-flavanone on the basis of spectroscopic evidence.
A new flavanone, named euchrestalfavanone A (I), mp 145-147°C, C25H28O5, was isolated from the root of Euchresta japonica HOOK. f. ex REGEL (Leguminosae) together with l-maackiain, medicagol and trifolirhizin. The structure of I was established to be 6, 3'-di-γ, γ-dimethylallyl-5, 7, 4'-trihydroxyflavanone on the basis of chemical and spectral evidence.
C-6 or C-8 substituted flavanones were determined by methods of chemical and/or 1H-NMR spectral analysis. We report a very convenient method for determining the substituted position of these flavanones using 13C-1H long range coupling. In connection with this study, we revised some structures of flavanones using this technique.
Three new prenylflavanones, sophoraflavanones H, I and J, with resveratrol residues, were isolated from the roots of Sophora moorcroftiana (Leguminosae).The structures were determined by spectroscopic methods. Therefore, these were new types of natural products which, when combined with flavanones and stilbenes, were named flavonostilbenes.
The extract of Schoenus nigricans afforded, in addition to a known stilbene and a known prenylflavanone, four new stilbenes and two new prenylflavanones. The structures were elucidated on the basis of spectral data.
One flavanone, euchrestaflavanone A and four isoflavonoids (lupinalbin A–C, and a previously unreported 4′-methyl ether of wighteone) were isolated from Lotus creticus. The structures were elucidated by spectroscopy.
Flemiflavanone-D from Flemingia stricta is active in vitro against Staphylococcus aureus and Mycobacterium smegmatis. Reexamination and interpretation of its spectral properties required revision of its molecular formula to C25H28O6 and its structure to 2S-5,7,4′-trihydroxy-6-γ,γ-dimethylallyl-3′-γ,γ-dimethylallyl-oxidoflavan-4-one. The new structure was confirmed when reaction with chlorotrimethylsilane sodium iodide in acetonitrile deoxygenated and cyclized flemiflavanone-D to the known dicycloeuchrestaflavanone A. The absolute stereochemistry of flemiflavanone-D was established to be 2S by circular dichroism measurements.
The proton signal of the hydrogen-bonded hydroxyl group of the 6-isoprenoid substituted flavanone was shifted more downfield than that of 6-nonsubstituted flavanone. By comparison of the chemical shifts of the hydrogen-bonded hydroxyl groups of 8-(3″,3″-dimethylallyl)-5,7,3′,4′-tetrahydroxyflavanone (3) and its 6-isomer (4) isolated from Wyethia helenioides, the proposed structures 3 and 4 were reversed each other. Comparison of the chemical shift of the hydroxyl group is a facile method to discriminate the 6-isoprenoid substituted flavanone and the 6-nonsubstituted one.
Two-, three- and four-bond spin–spin coupling between 13C and hydrogen-bonded hydroxy-protons, identified by deuterium exchange, is shown to aid the assignment of 13C n.m.r. spectra in a series of 5-hydroxyflavones and flavonones.
The methanolic extract of the leaves of Macaranga vedeliana furnished a new flavonol, macarangin (6-[(E)-3″,8″-dimethyl-2″,7″-octadienyl]kaempferol).
Bioactivity-guided fractionation of a CH2Cl2 extract from the leaves of Piper aduncum afforded three new dihydrochalcones, piperaduncins A [3], B [4], and C [5], as well as two known dihydrochalcones, 2',6'-dihydroxy-4'-methoxydihydrochalcone [1] and 2',6',4-trihydroxy-4'-methoxydihydrochalcone [2] (asebogenin), together with sakuranetin, anodendroic acid methyl ester, and the carotenoid lutein. The structures of the isolates were elucidated by spectroscopic methods, mainly 1D- and 2D nmr spectroscopy. The proposed stereochemistry for compound 4 was deduced by NOESY spectroscopy and the corresponding energy minimum was established by molecular modelling calculations and translated into a 3D structure.