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Chemical constituents of the fruits of Artocarpus altilis
... Artocarpus consists about 50 species, this genus is widely distributed in tropical and subtropical regions, including Indonesia [2]. The bark, leaves, seeds, fruits and roots of some species are reported have medicinal properties and used for the treatment of diseases such as diarrhea, fever, cirrhosis, hypertension, inflammation, malaria, ulcers, sores and for tapeworm infections [3,4,5] One of the species of Artocarpus which is an endemic plant in Indonesia is Artocarpus kemando Miq. can produce many prenylated flavonoid compound by means of isolation and some compounds obtained show interesting biological activity [6,7,8]. ...
... The modified results were recrystallized with ether/hexane solvent to produce 6.6 mg yellow crystal. Expressed as compound (2) and analyzed by determining the melting point and TLC with three eluent systems. The success of the esterification was determined using UV-Vis and IR spectroscopy. ...
... Maximum peak at λmax 279 nm is a typical absorption of flavones in band II that shows the characteristics of benzoyl chromophore. UV-Vis spectrum of compound (2) in the MeOH solvent obtained λmax: 280 and 300 nm The maximum absorption in the ultraviolet region at λmax 300 nm represents the spectrum in band I and the maximum absorption at λmax 280 nm is the spectrum in band II. Based on this data it can be seen (2) has decreased wavelength (hypsochromic effect) when compared to compound (1) by 21 nm. ...
Artocarpus kemando Miq. is a species from the family Moraceae in Indonesia known as the Pudau plant. The purpose of this study is to isolate, characterize, modify and test the antibacterial activity of artocarpin compounds isolated from pudding plants. Stages of research include sample preparation, extraction, isolation, and purification of compounds using chromatographic techniques (TLC, VLC, and CC), characterization of compounds using spectroscopy. The isolated compound was obtained as a yellow crystal with a melting point of 185-187 °C. Based on the results of spectroscopic analysis, showed that the prenylated flavonoids had been successfully isolated, artocarpin in an amount of 35.2 mg. Modification of artocarpin with acetic anhydride produces artocarpin acetate as a yellow crystal. Artocarpin and modified compounds showed antibacterial activity against Bacillus subtilis and Escherichia coli.
... Breadfruit leaves contain flavonoids of 8-geranyl-4,5,7-trihydroxyflavone which serves as antidiabetic (Amarasinghe et al., 2008). Ethanol, ethyl acetate, and butanol contained in breadfruit leaves extract have the ability to inhibit an a-glucosidase enzyme (Badrie and Broomes, 2010). ...
... The composition in using breadfruit leaves affects the antioxidant capacity produced because breadfruit leaves contain antioxidants, such as flavonoids and phenols (Amarasinghe et al., 2008). The result of the phytochemical test shows that the ethanol extract of breadfruit leaves contains flavonoid, polyphenols, saponins, alkaloids, and tannins (Sairam, S. et al, 2013). ...
... Existem aproximadamente 50 espécies de plantas do gênero Artocarpus, família Moraceae, distribuídas principalmente na Ásia tropical, apresentando-se como uma excelente fonte de flavonoides (WANG et al., 2007;AMARASINGHE et al., 2008). A espécie Artocarpus altilis (Parkinson) Fosberg é uma árvore nativa da Indonésia, amplamente cultivada, de longa vida, com uma altura de até 25 metros, produzindo frutos sazonais ao longo de um período de 4 a 6 meses na forma cilíndrica e podendo pesar de 1 a 3 kg, produzindo cerca de 200 a 400 kg ou mais de frutos por ano. ...
... A espécie Artocarpus altilis (Parkinson) Fosberg é uma árvore nativa da Indonésia, amplamente cultivada, de longa vida, com uma altura de até 25 metros, produzindo frutos sazonais ao longo de um período de 4 a 6 meses na forma cilíndrica e podendo pesar de 1 a 3 kg, produzindo cerca de 200 a 400 kg ou mais de frutos por ano. Suas folhas foram tradicionalmente utilizadas para o tratamento de cirrose hepática, hipertensão e diabetes (WANG et al., 2007;AMARASINGHE et al., 2008;LATCHOUMIA et al., 2014). ...
p>A espécie Artocarpus altilis produz frutos popularmente conhecidos como fruta-pão. São climatéricos e contribuem com quantidades consideráveis de energia e fornecer os principais nutrientes da dieta. Podem ser consumidos cozidos, fritos ou torrados e em processos tecnológicos tendo potencial para ser empregados em biscoitos e comercializados como farinha. Na literatura são poucos os trabalhos que relatem as características desses frutos, principalmente da região Nordeste. Desta forma, objetivou-se avaliar a biometria e as características físico-químicas da fruta-pão coletada no município de Santa Rita, Paraíba, Brasil. Foram selecionados 30 frutos firmes em 3 estádios de maturação, com pedúnculo, casca verde e amarelada, látex presente e livres de lesões. Os frutos apresentaram em média diâmetro externo transversal e diâmetro externo longitudinal de 15,98 (± 0,12) e 13,11 (± 0,13) cm, respectivamente, bem como massa média de 1,52 (± 0,06) Kg e firmeza de 66,80 (± 1,13) N. Quanto a composição centesimal apresentou valores de umidade, cinzas, proteína, lipídeos e carboidrato de 68,76% (± 0,02), 0,61% (± 0,01), 1,73 ± (0,00), 0,55% (± 0,01) e 28,35%, respectivamente, valor energético 125,27 Kcal, teor de amido de 24,68% (± 0,39), °Brix 2,01 (± 0,01), pH 6,4 (±0,01), fenólicos 0,023% (± 0,02) de ácido tânico e Aw 0,993 (± 0,00). De acordo com os resultados das físico-químicas, os frutos estudados apresentaram grande potencial para serem explorados comercialmente pela indústria de alimentos.
Biometrics and physical-chemical characteristics of breadfruit ( Artocarpus altilis )
Abstract: The species Artocarpus altilis produces fruits popularly known as breadfruit. They are climacteric and contribute considerable amounts of energy and provide the main nutrients in the diet. They can be consumed cooked, fried or roasted and in technological processes having potential to be used in cookies and marketed as flour. In the literature, there are few studies that report the characteristics of these fruits, mainly in the Northeast region. In this way, the objective was to evaluate the biometry and the physicochemical characteristics of the breadfruit collected in the municipality of Santa Rita, Paraíba, Brazil. 30 firm fruits were selected in 3 maturation stages, with peduncle, green and yellow peel, and latex present and free of lesions. The fruits had a mean transversal external diameter and a longitudinal external diameter of 15,98 (± 0,12) and 13,11 (± 0,13) cm, respectively, as well as a mean mass of 1,52 (± 0,06) Kg and firmness of 66,80 (± 1,13) N. The centesimal composition presented values of moisture, ashes, protein, lipids and carbohydrate of 68,76% (± 0,02), 0,61% (± 0,01) , 1,73 (0,00), 0,55% (± 0,01) and 28,35%, respectively, energy value 125,27 Kcal, starch content of 24,68% (± 0,39) , 39), Brix 2,01 (± 0,01), pH 6,4 (± 0,01), phenolics 0,023% (± 0,02) tannic acid and Aw 0,993 (± 0,00). According to the physicochemical results, the fruits studied presented great potential to be commercially exploited by the food industry.</pre
... Artocarpus altilis (Parkinson) Fosberg (Moraceae) is a tree of moderate size and is widely cultivated in tropics as staple crop, animal feed, and construction material. Its leaves have been used traditionally for the treatment of liver cirrhosis, hypertension, and diabetes [8,9]. Pharmacological studies report the presence of flavonoids, [10,11] triterpenoids [12], and prenylflavonoids [8] in A. altilis and some flavonoids have shown anti-inflammatory activities [13] and also inhibit 5-lipoxygenase of cultured mastocytoma cells [14]. ...
... Its leaves have been used traditionally for the treatment of liver cirrhosis, hypertension, and diabetes [8,9]. Pharmacological studies report the presence of flavonoids, [10,11] triterpenoids [12], and prenylflavonoids [8] in A. altilis and some flavonoids have shown anti-inflammatory activities [13] and also inhibit 5-lipoxygenase of cultured mastocytoma cells [14]. The traditional usage of leaf to treat hypertension [15] and diabetes [16,17] has been proven scientifically. ...
This study was designed to elucidate the acute toxicity of Artocarpus altilis leaf and bark extracts. In acute toxicity study, no mortality or any toxic reaction was recorded in any group after 14 days of administering the extracts (2000 mg Kg(-1) BW). The extracts (ALA, ABA, ALM, and ABM) did not cause any behavioural or physical changes in experimental rats. There was no significant (P ≤ 0.05) difference in the biochemical parameters analysed between the groups. Slight elevation in activities of AST and ALT in extract treated groups was observed, but this did not exert any deleterious effect on the normal metabolism which was supported by the histopathology of liver. Histopathological studies showed no remarkable changes after 14 days of oral administration of ALA, ABA, ALM, and ABM extracts. The study contributes to establishing the nontoxic quality parameters of Artocarpus altilis leaf and bark parts and the results suggest the safety of the extracts in therapeutic uses.
... The stem and root barks were used in Indonesian traditional medicine to treat trouble digestion, diarrhea, dysentery, and toothache [1]. Previous investigations indicated that prenylated flavonoids were characteristic constituents for A. altilis [2][3][4][5][6]. This paper deals with the isolation and structure elucidation of a new prenylated aurone, artocarpaurone (1) from A. altilis along with two prenylated chalcones, three prenylated flavanones, and three triterpenes ( Figure 1). ...
... The known compounds were characterized as 1- [5,9], 3bacetoxycycloart-25-ene-24-one (7) [10,11], 3b-acetoxycycloart-25-methoxy-23-ene (8) [12], and 3b-acetoxy-urs-12-ene-11-one (9) [13], by detailed analyses of their NMR and ESI-MS data and comparison of them with reported values. Compounds 7 and 8 were previously isolated from the acetylated fractions of Euphorbia broteri [10] and Tillandsia usneoides [12], respectively. ...
Phytochemical study of the methanol extract of Artocarpus altilis resulted in the isolation of a new prenylated aurone, artocarpaurone (1), together with eight known compounds including two prenylated chalcones (2 and 3), three prenylated flavanones (4-6), and three triterpenes (7-9). The structure of 1 was elucidated as 6-hydroxy-2-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-ylmethylene]-3(2H)-benzofuranone by spectroscopic methods including 1D and 2D NMR spectra and FT-ICR-MS. Compound 1 showed moderate nitric oxide radical scavenging activity, whereas 2 and 3 had moderate 2,2-diphenyl-1-picrylhydrazyl radical scavenging effect, compared with the positive control (+)-catechin.
... A. altilis has been reported to contain non-flavonoid phenolic substituents such as moracin M and oxyresveratrol with a potent antioxidant activity 22 . The water extract with the lowest radical scavenging activity demonstrated the highest flavonoid content, whereas the ethyl acetate extract with superior radical scavenging activity demonstrated the lowest flavonoid content. ...
Free radicals are ions, molecules or atoms with unpaired electrons that are highly unstable and reactive against other molecules. Free radicals contributed in the development of various human disorders. In this study, we investigated the possible new sources of natural radical scavengers which could provide antioxidant mechanisms to protect against the negative effects of free radicals. Radical scavenger activity of water, ethanol and ethyl acetate extracts of A. altilis extracts were evaluated by the radical DPPH scavenging test. All extracts demonstrated radical scavenger activity in which the ethyl acetate extract demonstrated the strongest activity as a radical DPPH scavenger. As A. altilis leaves contains various phenol and flavonoid compounds, the content of phenol and flavonoid compounds were determined by colorimetric techniques using the Folin-Ciocalteu assay and AlCl3 reagent, respectively. Our investigation revealed that the ethyl acetate extract showed the highest activity (IC50: 66.52 ± 0.70 µg/mL) compared to the ethanol (IC50: 88.08 ± 5.54 µg/mL) and water (IC50: 399.85 ± 9.48 µg/mL) extracts. The ethyl acetate extract also contains the highest amount of phenol contents (6.47 ± 0.11 % gallic acid equivalent) compared to the ethanol and water extracts (5.78 ± 0.14 % and 1.02 ± 0.15, respectively). Interestingly, the total flavonoid content of the ethyl acetate extract is the lowest (0.22 ± 0.02 % quercetin equivalent) among the others (0.33 ± 0.01 % and 0.50 ± 0.01 % for ethanol and water extract, respectively). We found a strong correlation between the radical scavenger activity with the total phenol content of the extracts but not with the total flavonoid contents. This study indicated that A. altilis leaves represents a promising new source of natural antioxidants
... However, our screening failed to detect terpenoids in C. ovatum nut. The negative results for A. altilis and G. binucao also did not agree with previous reports(Amarasinghe et al. 2008; Ragasa et al. 2014b).Saponins are a group of amphipathic molecules that contain a glycoside moiety and a triterpene or steroid moiety. They may serve as antifeedants against animals and protection against pathogens such as microbes and fungi(Hussain et al. 2019). ...
Nine Philippine indigenous fruits were screened for phytochemical constituents and assessed for total phenolics and antioxidant and antibacterial activities. Qualitative tests revealed the presence of alkaloids in Canarium ovatum, cardiac glycosides in Ficus pseudopalma and C. ovatum, and terpenoids in Antidesma bunius and C. ovatum. Total phenolics were highest in Garcinia binucao and Mangifera altissima with 758 and 694 mg gallic acid equivalent (GAE) / 100 g fresh matter (FM), respectively. The DPPH radical scavenging activities ranged from 82-516 mg ascorbic acid equivalent antioxidant activity (AEAC) /100 g FM, with M. altissima having the highest value and followed by Rubus rosifolius (513 mg AEAC / 100 g FM). Ferric reducing activities were highest for M. altissima and G. binucao with 111 mg and 121 mg ascorbic acid equivalents (AAE) / 100 g FM, respectively. Phenolic and flavonoid contents were strongly and positively correlated (P < 0.05). Moreover, phenolic contents may have significant contributions to the observed radical scavenging and ferric reducing activities based on their strong positive correlations (P < 0.05). For the antibacterial activities, extracts from Citrus hystrix and R. rosifolius were the most effective against Escherichia coli (MIC 80 = 1.70 mg GAE/mL), while the F. pseudopalma extract was the most effective against Staphylococcus aureus (MIC 80 = 0.56 mg GAE / mL). Present results showed that the selected indigenous fruits could be valuable sources of phytochemicals, such as phenolics and flavonoids, with potential antioxidant and antibacterial activities.
... However, our screening failed to detect terpenoids in C. ovatum nut. The negative results for A. altilis, and G. binucao, also did not agree with previous reports(Amarasinghe et al. 2008; Ragasa et al. 2014b).Saponins are a group of amphipathic molecules that contain a glycoside moiety and a triterpene or steroid moiety. They may serve as antifeedants against animals and protection against pathogens such as microbes and fungi(Hussain et al. 2019). ...
Nine Philippine indigenous fruits were screened for phytochemical constituents and assessed for total phenolics and antioxidant and antibacterial activities. Qualitative tests revealed the presence of alkaloids in Canarium ovatum, cardiac glycosides in Ficus pseudopalma and C. ovatum, and terpenoids in Antidesma bunius and C. ovatum. Total phenolics were highest in Garcinia binucao and Mangifera altissima with 758 and 694 mg gallic acid equivalent (GAE) / 100 g fresh matter (FM), respectively. The DPPH radical scavenging activities ranged from 82-516 mg ascorbic acid equivalent antioxidant activity (AEAC) /100 g FM, with M. altissima having the highest value and followed by Rubus rosifolius (513 mg AEAC / 100 g FM). Ferric reducing activities were highest for M. altissima and G. binucao with 111 mg and 121 mg ascorbic acid equivalents (AAE) / 100 g FM, respectively. Phenolic and flavonoid contents were strongly and positively correlated (P < 0.05). Moreover, phenolic contents may have significant contributions to the observed radical scavenging and ferric reducing activities based on their strong positive correlations (P < 0.05). For the antibacterial activities, extracts from Citrus hystrix and R. rosifolius were the most effective against Escherichia coli (MIC 80 = 1.70 mg GAE/mL), while the F. pseudopalma extract was the most effective against Staphylococcus aureus (MIC 80 = 0.56 mg GAE / mL). Present results showed that the selected indigenous fruits could be valuable sources of phytochemicals, such as phenolics and flavonoids, with potential antioxidant and antibacterial activities.
... The presence of sterols in African mango seeds support the research reported by Amarasinghe et al (2008). This was corroborated by De Stafani et al (2000) who in a controlled case-study experiment showed the consumption of plant sterols to be inversely proportional to the occurrence of stomach cancer. ...
African mango (Irvingia gabonensis) belongs to the Irvingiaceae family of plants, it has a long history both as a
food and medicine. This study was carried out to analyze the phytochemicals of seed extract as well as to evaluate
its acute oral toxicity (LD50). A total of thirteen rats were used for the acute toxicity study and was done in two
phases; in phase I, nine rats were divided into three groups of three rats each and were orally administered with
10, 100 and 1000mg/kg body weight of the extract. The rats were observed for mortality and general behavior for
24hrs. In phase II, four rats were administered with the extract at higher doses of 1500, 2500, 3500 and 5000mg/kg
respectively and were observed for mortality and other signs of toxicity for 24hrs. The results of the qualitative
phytochemical analysis revealed the presence of alkaloids, flavonoids, glycoside, saponin, tannins, resins and
reducing sugar with the absence of coumarin, while quantitative analysis shows that the extract is rich in
glycosides, followed by flavonoids, followed by alkaloids, followed by saponin, and lastly tannin A and tannin B.
Acute toxicity revealed that the extract was practically nontoxic with oral LD50 greater than 5000mg/kg body
weight. In conclusion, these results showed that the extract is rich in phytochemicals and was found to be relatively
safe at administered doses.
Keywords: acute toxicity; Irvingia gabonensis; phytochemical analysis and seed extract.
... The presence of sterols in African mango seeds support the research reported by Amarasinghe et al (2008). This was corroborated by De Stafani et al (2000) who in a controlled case-study experiment showed the consumption of plant sterols to be inversely proportional to the occurrence of stomach cancer. ...
... The presence of sterols in African mango seeds support the research reported by Amarasinghe et al (2008). This was corroborated by De Stafani et al (2000) who in a controlled case-study experiment showed the consumption of plant sterols to be inversely proportional to the occurrence of stomach cancer. ...
African mango (Irvingia gabonensis) belongs to the Irvingiaceae family of plants, it has a long history both as a food and medicine. This study was carried out to analyze the phytochemicals of seed extract as well as to evaluate its acute oral toxicity (LD50). A total of thirteen rats were used for the acute toxicity study and was done in two phases; in phase I, nine rats were divided into three groups of three rats each and were orally administered with 10, 100 and 1000mg/kg body weight of the extract. The rats were observed for mortality and general behavior for 24hrs. In phase II, four rats were administered with the extract at higher doses of 1500, 2500, 3500 and 5000mg/kg respectively and were observed for mortality and other signs of toxicity for 24hrs. The results of the qualitative phytochemical analysis revealed the presence of alkaloids, flavonoids, glycoside, saponin, tannins, resins and reducing sugar with the absence of coumarin, while quantitative analysis shows that the extract is rich in glycosides, followed by flavonoids, followed by alkaloids, followed by saponin, and lastly tannin A and tannin B. Acute toxicity revealed that the extract was practically nontoxic with oral LD50 greater than 5000mg/kg body weight. In conclusion, these results showed that the extract is rich in phytochemicals and was found to be relatively safe at administered doses.
... Several studies on the phytochemical test showed that the breadfruit leaves contain flavonoids, phenols, saponins and tannins (Baba et al., 2016). Its flavonoid compounds were also noted as strong anti-diabetes (Amarasinghe et al., 2008). Gustina and Anica (2012) reported the extract of ethanol, ethyl acetate, and butanol obtained from breadfruit leaves extract has the ability to inhibit the enzyme a-glucosidase. ...
Efforts to lower blood sugar levels for diabetes mellitus patients can take by consuming a popular functional drinks which has been added by herbal ingredients such as breadfruit leaves. The aim of this research is to observe the effect of addition three-types of sweetener (aspartame, acesulfam k, and sorbitol) in different ratio (50%: 25%: 25%, 25%: 50%: 25%, 25%: 25%: 50%) to the antioxidant capacity and glucose level of functional drinks made from breadfruit leaves, as well as its number of calories and variety sensory tests (sour taste, sweetness and texture). The experimental design used a Completely Randomized Design with three replications. This study also employs 35 panellists to produce organoleptic quality data in two repetitions. All collected data were then analyzed using ANOVA test followed by DMRT test. Results showed that the highest antioxidant capacity was obtained by ratio 25%: 25%: 50% of aspartame, acesulfam k, and sorbitol with IC50 value of 64,717 ppm. Meanwhile the lowest glucose level was resulted by ratio 50%: 25%: 25% of aspartame, acesulfam k, and sorbitol in value of 25.53 g/100g. The highest number of calorie was produced by ratio 25%: 25%: 50% of aspartame, acesulfam k, and sorbitol with a value of 126.44 cal. / 100gr. Whereas, the most preferred formulas of breadfruit drink formulas are found in ratio 25%: 25%: 50% of aspartame, acesulfam k, and sorbitol.
... The breadfruit is a great food, acting as an intestinal regulator (Latchoumia, 2014). It can be used as anti-inflammatory, anti-diabetic, anti-bacterial and estrogen regulation (Somashekhar et al 2013) and also as antioxidant (Amarasinghe et al. 2008). ...
The breadfruit tree (Artocarpus altilis) is an exotic species found in tropical regions of the world, serving the cultivation of small farmers. This study aimed to evaluate the variability of breadfruit, genotypes located in four districts of the Recôncavo Baiano region (Cruz das Almas, Governador Mangabeira, São Felipe and Sapeaçu) through a characterization of the fruits. Were identified and georeferenced 32 genotypes. For each genotype, eight fruits were collected, which were evaluated for: fruit weight, length and diameter of the fruit pulp thickness, pulp yield length and diameter of the floral axis, weight of the pulp, the shaft and the shell. The pulps were homogenized for physical-chemical and chemical analysis (pH, titratable acidity, the total sugar, reducing sugar and non-reducing sugar, ashes, starch and protein). The data were submitted to descriptive statistical analysis and multivariate cluster analysis. The results showed variability among genotypes, with the formation of four main groups of genetic dissimilarity. Multivariate analysis was efficient to discriminate genotype CA5 and CA9 as the most divergent. The characteristics that contribute most to the formation of groups were full starch and yield of pulp.
... Artocarpus plant belongs to Moraceae family. It consists of about 50 species distributed over tropical forest of the world [1][2]. Artocarpus are known for their edible fruits such as Artocarpus heterophyllus (jackfruit), Artocarpus altilis (breadfruit) and Artocarpus integer (cempedak). ...
Six known compounds identified as 4',5-dihydroxy-6,7-(2,2-dimethylpyrano)-2'-methoxy-8-γ,γ-dimethylallyflavone (1), cudraflavone A (2), artocarpin (3), cycloartobiloxanthone (4), artonin E (5) and oxyresveratrol (6) were isolated from the stem barks of Artocapus scortechinii King. Another four compounds namely macakurzin C (7), flemichapparin A (8), luteolin (9) and apigenin (10) were isolated from the leaves. Structures of all pure compounds were elucidated spectroscopically using 1D NMR (¹H,¹³C, DEPT), 2D NMR (COSY, HMQC, HMBC), MS and FTIR, as well as by comparison with literature data. All isolated compounds were evaluated for their antioxidant capacities using 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) and ferric reducing antioxidant potential (FRAP) assays. Luteolin (9) showed the best ability to act as DPPH free radical scavenger with IC50 value of 9.51 µM. Luteolin (9) also exhibited the strongest scavenger and potent ferric ion reducer compared to other isolated compounds in the ABTS and FRAP assays with IC50 value of 124.4µM and 4.07 ± 0.180 mM FRAP equivalent respectively.
... The presence of sterols as observed in African mango (pulp; seeds) and breadfruit is in accordance with a report by Amarasinghe et al. (2008). It was not detected in soursop contrary to a report by Adewole and Ojewole (2008) and also not detected in sweetsop. ...
The antioxidant activity, total phenols content and phytochemical constituents of edible portions of four underutilised tropical fruits; Irvingia gabonensis (African mango), Artocarpus altilis (breadfruit), Annona muricata (soursop) and Annona squamosa (sweetsop) were determined. Extracts of fruit samples were screened for selected phytochemicals using standard methods whereas the total phenols content and antioxidant activity (by free radical scavenging action) was determined by the Folin-Ciocalteu method and DPPH assay, respectively. The antioxidant activities were high with values ranging from 63% inhibition (breadfruit) to 78% inhibition (African mango pulp). African mango seeds had the highest total phenols content (20.96 mg GAE /100g). Tannins, triterpenoids, saponins, sterols, cardiac glycosides, flavanoids and coumarins were detected in most of the fruit extracts. The study revealed that these underutilised tropical fruits have considerable free radical scavenging (antioxidant) activity and an array of phytochemicals necessary to significantly impact health of consumers.
... The presence of sterols as observed in African mango (pulp; seeds) and breadfruit is in accordance with a report by Amarasinghe et al. (2008). It was not detected in soursop contrary to a report by Adewole and Ojewole (2008) as well as not detected in sweetsop. ...
The surge in chronic diseases has necessitated the global call for increased consumption of diverse fruits and vegetables resulting in the need to study the potential health beneficial constituents of the underutilised. This research was aimed at assessing the dietary fibre fractions, proximate composition, antioxidant activity and phytochemical constituents of edible portions of four underutilised fruits viz., African mango (seeds and pulp), breadfruit (pulp), soursop (pulp) and sweetsop (pulp). Their total phenolic and ascorbic acid (vitamin C) contents were also determined. Samples for all determinations except proximate analysis were freeze-dried and stored: Some under refrigeration conditions for dietary fibre analysis, and the rest at - 20 oC. Proximate and phytochemical analysis was done by standard methods. The antioxidant activity and phenolics were determined by spectroscopy using 2, 2-diphenyl-1-picrylhydrazyl radical scavenging and the Folin-Ciocalteu protocol, respectively. The ascorbic acid content was determined by titrimetry and an enzymatic-gravimetric method employed for the dietary fibre determinations. Proximate values (% mean) ranged from 2.63±0.11 to 6.71±0.07; 2.44±0.07 to 4.00±0.03 and 2.60±0.41 to 13.90±0.58 for protein, ash and fat respectively. Generally, tannins, triterpenoids, saponins, sterols, cardiac glycosides, flavanoids and coumarins were detected. Antioxidant activity of the samples ranged from 63% (breadfruit) to 78% (African mango pulp) and the highest phenolic content was recorded in African mango seeds. Total dietary fibre contents ranged from 11.50 (soursop) to 22.70 (African mango pulp) g/100g while ascorbic acid contents of the fruit mesocarps ranged from 20.32 (sweetsop) to 62.52 (soursop) mg/100g. There were non-significant correlations (P < 0.05) between the phenolics, ascorbic acid contents and antioxidant activities. The study suggests significant composition of health beneficial constituents - dietary fibre, vitamin C and presence of an array of phytochemicals - as well as fairly high antioxidant activities of the stated fruits. Thus, the need to exploit them in seeking optimum health of the populace.
... Steppogenin (S) is a natural flavanone with strong tyrosinase inhibitory activity and is widely distributed in Moraceae plants, such as Artocarpus heterophyllus, Cudrania tricuspidata, A. xanthocarpus, A. altilis, Morus nigra, M. alba, and M. lhou (Amarasinghe, Jayasinghe, Hara, & Fujimoto, 2008;Jeong et al., 2009;Jin et al., 2015;Lim, Jin, Woo, Lee, & Kim, 2013;Zheng, Cheng, To, Li, & Wang, 2008;Zheng, Tan, Chen, & Wang, 2013;Zheng et al., 2010). However, its poor solubility in aqueous systems greatly limits its application as an anti-browning agent for food products. ...
Oil-in-water microemulsions (O/W MEs) allow the preparation of insoluble compounds into liquid. In this study, we prepared O/W MEs to improve the solubility and stability of steppogenin (S) in aqueous liquid, and studied their ability to inhibit fresh apple juice browning. The ME technique greatly increased steppogenin solubility up to 3000-fold higher than that in water. All SMEs demonstrated good stability after acceleration and long-term storage. In particular, 0.01% SME was associated with dramatic inhibition of fresh apple juice browning after 24 h at room temperature and 7 days at 4 °C, and its antibrowning effects were further improved when combined with 0.05% ascorbic acid. On the other hand, simultaneous encapsulation of steppogenin with vitamin E or butylated hydroxytoluene into ME did not greatly improve SME antibrowning effects. Taken together, these results suggested that steppogenin might serve as a potential antibrowning agent to preserve fresh apple juice.
... Out of 43 volatile compounds identified in breadfruit boiled for 10 min, the main component was ethyl acetate (38%). From the methanol and ethyl acetate fruit extracts of A. altilis, arylbenzofuran of moracin M; stilbenes of oxyresveratrol and artoindonesianin F; flavonoids of norartocarpanone, norartocarpetin and isoartocarpesin; triterpenes of 3β-acetoxyolean-12-en-11-one and cycloartenyl acetate; and sterols of sitosterol β-D-glucopyranoside and sitosterol have been isolated (Amarasinghe et al., 2008). ...
Artocarpus altilis (breadfruit) and Pandanus tectorius (screw pine) are two cultural icons of Oceania. Fruits of both species are rich in carbohydrates, and contain proteins, vitamins and minerals. Endowed with triterpenes, flavonoids, stilbenes, arylbenzofurans and sterols as chemical constituents, fruits of A. altilis possess antioxidant, antimicrobial, anticancer and anti-hyperglycemic properties. With phenolic compounds such as flavonoids and caffeoylquinic acids, fruits of P. tectorius possess antioxidant, antibacterial, anti-diabetic, a-glucosidase inhibitory and antidiarrheal properties. In comparison, more bioactivities have been reported in other plant parts such as leaves, bark, wood and root of these two species. Nevertheless, the scientific evidence is convincing that the regular consumption of fruits of A. altilis and P. tectorius by the islanders of the Pacific does have both nutritive and medicinal values.
... Artocarpus plant belongs to Moraceae family. It consists of about 50 species distributed over tropical forest of the world [1][2]. Artocarpus are known for their edible fruits such as Artocarpus heterophyllus (jackfruit), Artocarpus altilis (breadfruit) and Artocarpus integer (cempedak). ...
The antioxidant activities of extracts (n-hexane, dichloromethane, ethyl acetate and methanol) from the leaves and stem barks of Artocarpus scortechinii were evaluated using various biochemical assays. The quantification of the Total Antioxidant Capacity was measured using ferric reducing antioxidant potential (FRAP) and 2,2'-azino-bis(3-ethyl-benzothiazoline-6-sulphonic acid) (ABTS) assays. While, the qualitative of The Total Phenolic Content (TPC) was determined via standard gallic acid calibration graph which was expressed as mg gallic acid equivalent (GAE)/g of dry weight (dw) using Folin Ciocalteau’s reagent. Among all the extracts tested, the methanolic extract of the stem barks showed the highest phenolic content with TPC value of 136.84 mg GAE/g dry weight (dw). FRAP results were expressed as mM equivalent to FeSO4.7H2O by calculating from the standard FeSO4.7H2O calibration graph. The ethyl acetate extract of the stem barks showed the most significant reducing potential in the range between 0.27-2.47 mM FRAP. ABTS+’ radical scavenging capacity showed that the ethyl acetate extract of the stem barks had the highest scavenging capacity at concentration 1.0 mM with percentage of 90.9%.
... There are several bioactivities for this plant which had been identified, i.e. antioxidant, antimalaria, antiviral, anti-platelet aggregation and cytotoxic activity for several cell lines [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. The leaves were rich of phenolic compounds including flavonoids, stilbenoids and arylbenzofurans [7][8][9][10][11][12][13][21][22][23]. More than fifty compounds had been identified and the group of flavonoid was known as the major constituent from the leaves [7,[9][10][11]14]. ...
Objective: Artocarpus altilis or Sukun is one kind of herbal medicine that is usually used by Indonesian people. It is widely known that the flavonoid derivative of A.altilis, one of its major bioactive constituent, has a broad range of pharmacological activity such as antioxidant, antibacterial, anti-inflamantory, antidiabetic and many others. In this study we investigated the bioactive constituent and influence of ethanol concentration, time and temperature on the antioxidant and antibacterial activity of A.altilis leaves in order to find appropriate and effective condition for its extraction. Methods: A.altilis leaves were extracted with different ethanol concentration (50, 60 and 70% v/v), time (1, 2, 3, 4 and 24 h) and temperature (70 ° C and room temperature). Influence of different extraction processes was analyzed on antioxidant capacity, antibacterial activity, total phenolic and total flavonoid content. Isolation of bioactive compound was performed by column chromatography method and structure was elucidated by 1H and 13C FT-NMR (Fourier Transform-Nuclear Magnetic Resonance) spectra. Results: Concentration of 70% v/v ethanol, 70 ° C and 1 h extraction process were found to be the most appropriate condition for extraction of A.altilis leaves in order to obtain bioactive components which gave both antioxidant and antibacterial activity against E.coli while yield of total flavonoid and phenolic content of extract should not less than 1.9 and 1.8% w/w, respectively. Structure elucidation of isolated compound identified that prenylated flavonoid, i.e. 1-(2,4-dihydroxyphenyl)-3-(8-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-5-yl)propa-1-one is one of its important bioactive constituent. Conclusion: Use of ethanol concentration, temperature and time influenced the yield of total phenolic and flavonoid content and bioactivity of A.altilis extract. It is recommended to heat the extraction process to 70 ° C in order to obtain both optimal antioxidant and antibacterial activity from ethanol extract of A.altilis leaves.
... Basically Artocarpus species consists of phenolic compounds which include flavonoids, stilbenoids, arylbenzofurons and Jacalin, a lectin. Over 130 compounds are identified in various organs of the tree of Artocarpus altilis, more than 70 of which derived from the phenylpropanoid pathway (Amarasinghe et al., 2007). Leaves of Artocarpus altilis contain tannins, phenolics, glycosides, saponins, steroids, terpenoids and anthraquinones. ...
Objective: This research was aimed to investigate the pharmacognostical, phytochemical and total phenolic content of Artocarpus altilis(Parkinson) Fosberg leaves. Method: Macroscopy, microscopy, physicochemical, phytochemical analysis and thin layer chromatography of Artocarpus altilis leaves were carried out. Folin-Coicalteau method was used to determine the total phenolic content. Results: Morphological study showed that the leaves were alternate or irregular, ovate and finger-like shaped with an average of 30.21cm in length and 24.25cm in width. Microscopy on leaves and powder showed the presence of anomocytic stomata, trichomes, xylem, starch grains, lignin, and calcium oxalate crystals. Phytochemical test showed the presence of mucilage, flavonoid, steroid, tannin and phenolic compound and anthraquinone glycosides. Physicochemical analysis showed 11.64% of loss on drying, 9% of total ash value; and water soluble extractive value of 21.32% as highest. Total phenolic content was found to be 26.22 mg GAE/g. Conclusion: From this study, it can be concluded that the ethanolic extracts of Artocarpus altilis leaves possess modest amount of phenolic compounds in the leaves of this plant.
... Over 130 compounds are identified in various organs of the tree of A. altilis, more than 70 of which derived from the phenylpropanoid pathway, including a number of prenylated dihydrochalcones [16][17][18][19][20][21][22][23][24][25], prenylated flavonoids [21][22][23][25][26][27][28][29][30][31][32], and prenylated aurones [25,33] together with some triterpenoids and phenolic compounds [34][35][36][37] (Figs. 1-4). ...
Human pancreatic cancer cell lines have remarkable tolerance to nutrition starvation, which enables them to survive under a tumor microenvironment. A novel antiausterity strategy in anticancer drug discovery led to the discovery of agents that preferentially inhibit the survival of cancer cells under low nutrient conditions. Artocarpus altilis (Family: Moraceae) is commonly referred to as breadfruit, traditionally for the treatment of many diseases. Many prenylated flavonoid and prenylated chalocones together with their cancer cell cytotoxicity were reported from this plant. This chapter briefly summarizes the constituents, biosynthesis, cytotoxicity, and antiausterity activity on PANC-1 human pancreatic cancer cell line of A. altilis.
... The presence of sterols as observed in African mango (pulp; seeds) and breadfruit is in accordance with a report by Amarasinghe et al. (2008). It was not detected in soursop contrary to a report by Adewole and Ojewole (2008) and also not detected in sweetsop. ...
The antioxidant activity, total phenols content and phytochemical constituents of edible portions of four underutilised tropical fruits; Irvingia gabonensis (African mango), Artocarpus altilis (breadfruit), Annona muricata (soursop) and Annona squamosa (sweetsop) were determined. Extracts of fruit samples were screened for selected phytochemicals using standard methods whereas the total phenols content and antioxidant activity (by free radical scavenging action) was determined by the Folin-Ciocalteu method and DPPH assay, respectively. The antioxidant activities were high with values ranging from 63% inhibition (breadfruit) to 78% inhibition (African mango pulp). African mango seeds had the highest total phenols content (20.96 mg GAE /100g). Tannins, triterpenoids, saponins, sterols, cardiac glycosides, flavanoids and coumarins were detected in most of the fruit extracts. The study revealed that these underutilised tropical fruits have considerable free radical scavenging (antioxidant) activity and an array of phytochemicals necessary to significantly impact health of consumers.
... It also contains phenolic compounds such as stilbenes, chalcones and flavones. 10 The leaves of selected plant are illustrated in Figure 1. ...
Objective: This research was aimed to investigate the antioxidant activity of Artocarpus altilis (Parkinson) Fosberg leaves. Materials and Methods: 2,2 diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and thiobarbituric acid (TBA) methods were used to determine the antioxidant activity with ascorbic acid as a reference. Results: Total phenolic content was found to be 26.22 mg gallic acid equivalents/g. In DPPH assay, the maximum free radical scavenging activity of the extract was found to be 70.59%. The TBA method also supported the antioxidant potential of the plant extract. Conclusion: From this detailed study, it can be concluded that the ethanolic extracts of A. altilis leaves possess moderate antioxidant property. It may be due to the presence of a modest amount of phenolic compounds in the leaves of this plant. Hence, the ethanolic extract of this plant may not act as first-line antioxidant defense but may be used as supportive antioxidant agent.
... The structures of the compounds isolated from Aframomum arundinaceum were established using spectroscopic analysis, especially, NMR spectra in conjunction with 2D experiments, COSY, HMQC, HMBC, and direct comparison with published information and with authentic specimens obtained in our research group for some cases. The compounds isolated from the fruits of A. arundinaceum ( Figure 1) [32] and kaempferol-3,7,4'-trimethylether C 18 H 16 O 6 (9; m/z 328.0; 157-158°C) [33]. The cytotoxicity of compounds 1-9 as well as the crude extracts was determined towards drug sensitive and resistant cancer cell lines. ...
Background
The search for natural products as potential cytotoxic agents has yielded promising candidates. However multidrug resistance (MDR) is still a major hurdle for patients receiving chemotherapy. In the present study, we evaluated the cytotoxicity of the methanol extracts of four dietary Aframomum plant species (A. arundinaceum, A. alboviolaceum, A. kayserianum and A. polyanthum) against nine sensitive and MDR cancer cell lines. We have also identified the bioactive constituents of A. arundinaceum.
Methods
The cytotoxicity of the methanol extracts of the above plants was determined using a resazurin reduction assay. Chromatographic techniques were used to isolate the constituents of A. arundinaceum.
Results
A preliminary experiment on leukemia CCRF-CEM cells at 40 μg/mL showed that the extracts from A. kayserianum and A. alboviolaceum as well as the isolated compounds namely compounds aframodial (1), 8(17),12-labdadien-15,16-dial (2), galanolactone (3), 1-p-menthene-3,6-diol (6) and 1,4-dimethoxybenzene (7) were less active, inducing more than 50% growth of this cell line contrary to A. polyanthum and A. arundinaceum extracts, galanals A (4) and B (5), naringenin (8) and kaempferol-3,7,4’-trimethylether (9). The IC50 values below or around 30 μg/mL were recorded with A. arundinaceum extract against eight of the nine tested cancer cell lines. This extract as well as compound 8 displayed IC50 values below 40 μg/mL towards the nine tested cancer cell lines whilst A. polyanthum extract, compounds 4, 5 and 9 showed selective activities. Collateral sensitivity (hypersensitivity) was observed with A. arundinaceum extract towards leukemia CEM/ADR5000 cells and glioblastoma U87MG.ΔEGFR compared to their respective sensitive counterparts CEM/CEM and U87MG.
Conclusion
The results of this study provide evidence of the cytotoxicity selected Aframomum species as well as a baseline information for the potential use of Aframomum arundinaceum in the fight against drug sensitive and otherwise drug-resistant cancers.
... The structures of the compounds isolated from Aframomum arundinaceum were established using spectroscopic analysis, especially, NMR spectra in conjunction with 2D experiments, COSY, HMQC, HMBC, and direct comparison with published information and with authentic specimens obtained in our research group for some cases. The compounds isolated from the fruits of A. arundinaceum ( Figure 1) [32] and kaempferol-3,7,4'-trimethylether C 18 H 16 O 6 (9; m/z 328.0; 157-158°C) [33]. The cytotoxicity of compounds 1-9 as well as the crude extracts was determined towards drug sensitive and resistant cancer cell lines. ...
A new clerodane diterpene derivative named crotonoligaketone was obtained from the stem bark of Croton oligandrum along with eight known compounds including crotonadiol, imbricatadiol, crotonzambefuran B, 7-acetoxytrachiloban-18-oic acid, 3-O-acetylaleuritolic acid, lupeol, beta-sitosterol, and stigmasterol. The structures of the isolated compounds were established on the basis of their spectral data and by comparison with those reported in the literature.
... The genus Artocarpus from the Moraceae family, which consists of approximately 50 species, is widely distributed in the tropical and subtropical regions, including Indonesia (Amarasinghe, Jayasinghe, Hara, & Fujimoto, 2008;Wang, Xu, Lin, Pan, & Zheng, 2007). Extensive phytochemical studies on the Artocarpus species have demonstrated that plants from this genus are rich in many classes of secondary metabolites including triterpenes, stilbenes and arylbenzofurans (Hakim et al., 2006;Jayasinghe, Samarakoon, Kumarihamy, Hara, & Fujimoto, 2008). ...
A new furanodihydrobenzoxanthone, artomandin (1), together with three other flavonoid derivatives, artoindonesianin C, artonol B, and artochamin A, as well as β-sitosterol were isolated from the stem bark of Artocarpus kemando. The structures of these compounds were determined on the basis of spectral evidence. All of these compounds displayed inhibition effects to a very susceptible degree in cancer cell line tests. Compound 1 also exhibited significant antioxidant capacity in the free radical 1,1-diphenyl-2-picrylhydrazyl tests.
Coronavirus Disease 2019 (COVID-19) caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is a global health threat. Traditional herbals and dietary plants with medicinal values have a long antiviral history and, thus, are extensively studied in COVID-19 therapeutics development. Breadfruit (Artocarpus altilis) is a food crop with rich nutrient composition. This study screened selected breadfruit prenylated flavonoids for their potential inhibitory activities against the SARS-CoV family receptors using molecular docking and molecular dynamics (MD) simulation. The A. altilis prenylated flavonoids were selected as target ligands (artocarpin, artoindonesianin V, artonin M, cudraflavone A and cycloartobiloxanthone) and molecular targets from the SARS-CoV family were designated as receptors. Molecular docking was applied with the Lamarckian Genetic algorithm to measure the receptor-ligand orientation using AutoDock Vina software. The structural interactions of the receptor-ligand complexes were visualised using the Biovia Discovery Studio 4.5. Under all possible receptor-ligand combinations, the complexes’ minimum binding affinities (MBA) ranged from -5.5 to -9.1 kcal/mol and held by hydrophobic interactions, hydrogen bonds and electrostatic attractions. Receptor-ligand complexes with the least MBA (<-6.0 kcal/mol) along with strong structural interactions were validated by MD simulation using the GROMACS software. The 5RE4-artocarpin and 5RE4-artoindonesianin V showed the highest hydrophobic interactions at MBA=-6.6 kcal/mol and -6.4 kcal/mol, respectively. The trajectory analysis of 5RE4-artocarpin and 5RE4-artoindonesianin V complexes was fairly stable throughout a 50 ns MD simulation run. The findings conclude that artocarpin and artoindonesianin V are good potential SARS-CoV family receptor inhibitors.
Artocarpus altilis is a species whose fruit possesses important nutritional characteristics; this fruit has a major advantage in the agri-food sector and can provide a varied range of food products. The objective of the study is to provide information on the physicochemical, technological, physiological and genetic characteristics of the breadfruit by means of a bibliographic synthesis in order to obtain an overview of possible uses of this species in Benin. The study made it possible to note the existence of several varieties of the species of which the two morphotypes currently registered in Benin are locally referred to as "Azintin" and "Bèléfututin" in Wémènou; The denomination of the species by local populations varies from one region to another. The breadfruit usually grows on deep, fertile, well-drained soils. The fruit contains carbohydrates, proteins, lipids, celluloses, minerals, vitamins C, A, B1 and B2. It thus constitutes a solution in the fight against malnutrition and a great asset for the assurance of food safety and security. The food use of the tree in Benin is the preparation of the fruit in the baked, fried or associated form with banana plantain to obtain the fufu, a product similar to crushed yam.
The stem bark of Artocarpus kemando furnished 24-methylenecycloartenyl acetate (fatty acyl ester) (1) together with cycloartobiloxanthone (2). Compound 1 was obtained for the first time from this species. The structures of both compounds were determined using NMR and MS analysis. A cytotoxic study showed that the crude extract of the stem bark of Artocarpus kemando was significantly active against the HL-60 (Human promyelocytic leukemia cell) and IRM-32 (Human neuroblastoma cell) cell lines. This is the first report on the cytotoxic activity of Artocarpus kemando.
The breadfruit is believed to be native to a vast area extending from the Indo-Malayan Archipelago the Philippines and the Moluccas through New Guinea to Western Micronesia. At least two species (A. camansi and A. mariannensis) and at least two different events (vegetative propagation coupled with human selection in Melanesia and Polynesia, and introgressive hybridization in Micronesia) were involved in the origins of breadfruit (Zerega et al. 2005). Most Melanesian and Polynesian cultivars appear to have arisen over generations of vegetative propagation and selection from A. camansi. In contrast, most Micronesian breadfruit cultivars appear to be the result of hybridization between A. camansi-derived breadfruit and A. mariannensis. Breadfruit widely planted in tropical Asia and has became a popular staple food crop and abundantly planted in garden areas, mature fallow forests, village tree groves, and in home gardens on both high islands and atolls throughout Melanesia, Polynesia, and Micronesia.
The Food and Agriculture Organization recently reported that the number undernourished people has reached a record high of 1.02 billion, most prevalent in the tropics. Breadfruit, Artocarpus altilis (Parkinson) Fosberg, is an underutilized Oceanic staple crop long recognized for its potential to alleviate hunger in tropical climates. Breadfruit can be grown sustainably with minimal agricultural inputs and can be multicropped with high value cash crops such as coffee, pepper, or vanilla. A great diversity of cultivars with varying nutritional and agronomic characteristics exists, yet few cultivars are widely cultivated. Recent developments in micropropagation have made possible large scale propagation and dissemination but to fully utilize this resource, a deeper understanding of the nutritional characteristics, and the development of new products and markets are needed. This review will highlight and describe the state of our current knowledge and the potential for breadfruit as a sustainable crop to provide new foods for Western markets and food security for the growing global population.
Medicinal plants are known to posses therapeutic properties and have been used since ancient times to treat various human diseases/disorders effectively. In the present study, the effect of Artocarpus altilis leaves (AL), bark (AB), and fruit (AF) on glucose hydrolyzing enzymes α-amylase, α-glucosidase, sucrase, and effect on glucose uptake by yeast cells was investigated. Inhibition of all three enzymes by the cold and hot aqueous extracts of AB was the highest followed by AL and AF. AL and AB in powder form increased the activity of α-glucosidase. The highest glucose uptake by yeast cells was by AL followed by AB and AF. The enhancement of glucose uptake was dependent on both the sample and glucose concentration. The results suggest that the possible mode of action of A. altilis as hypoglycemic agent is by inhibiting carbohydrate metabolizing enzymes and by facilitating the glucose diffusion through cell membrane, hence can be effectively utilized as therapeutic agents in the management of type II diabetes.
Dried heartwood powder of Maclura pomifera, Moraceae, was extracted with acetone. Silica gel column chromatography (CC) of the crude extract yielded 2',3',4',5'-tetrahydroxystilbene (oxyresveratrol).
Two isoprenylated 2-arylbenzofurans, artoindonesianins X and Y (1-2), together with seven known flavonoids, have been isolated from the roots and tree bark of Artocarpus fretessi. Their structures were established on the basis of spectral analysis. Compounds 1 and 2 showed moderate activity against the brine shrimp Artemia salina.
The essential oil of black cumin seeds, Nigella sativa L., was tested for a possible antioxidant activity. A rapid evaluation for antioxidants, using two TLC screening methods, showed that thymoquinone and the components carvacrol, t-anethole and 4-terpineol demonstrated respectable radical scavenging property. These four constituents and the essential oil possessed variable antioxidant activity when tested in the diphenylpicrylhydracyl assay for non-specific hydrogen atom or electron donating activity. They were also effective ·OH radical scavenging agents in the assay for non-enzymatic lipid peroxidation in liposomes and the deoxyribose degradation assay.
A new flavonone, a new prenylflavone, a novel phenolic compound, heterophylol, reported in a previous paper, and nine known flavonoids have been isolated from the root of Artocarpus heterophyllus. The two new flavonoids have been characterized as 5,2′-dihydroxy-7,4′-dimethyoxyflavanone and 8-(γ,γ-dimethylallyl)-5,2′,4′-trihydroxy-7-methoxyflavone, respectively.
Three new prenylated flavones, artelastin, artelastochromene and artelasticin, along with the known artocarpesin, were isolated from the wood of Artocarpus elasticus. Structures were elucidated by spectroscopic techniques.
The Department of Medicinal Chemistry and Molecular Pharmacology's laboratory has adopted four “bench top” bioassays which do not require higher animals to screen and direct the fractionation of botanical extracts in drug discovery efforts. These are: 1. The brine shrimp lethality test (BST) (a general bioassay), 2. The inhibition of crown gall tumors on discs of potato tubers (an antitumor bioassay), 3. The inhibition of frond proliferation in duckweed (a bioassay for herbicides and plant growth stimulants), and 4. The yellow fever mosquito larvae lethality test (a bioassay for pesticides). The materials and procedures for those bioassays will be briefly described. The authors' results in applying these simple methods in the discovery of Annonaceous acetogenins will be presented to illustrate their successful use. The BST is especially suggested as an inexpensive, simple, and rapid means of standardization of bioactivity in heterogeneous botanical products.
Several species of the genus Artocarpus (Moraceae) have been investigated in our laboratories during the last decade. Over 60 phenolic constituents have been discovered and characterized, including 27 new compounds from 13 Indonesian taxa of Artocarpus, namely A. champeden, A. lanceifolius, A. teysmanii, A. scortechinii, A. rotunda, A. maingayi, A. kemando, A. bracteata, A. altilis, A. fretessi, A. gomezianus, A. reticulatus and A. glaucus. The principal and the most pronounced features of these phenolic constituents are the assembly of an isoprenyl substituent at C-3 of a flavone skeleton by closure of an ether bridge or a carbon–carbon linkage with the B ring of the skeleton, which may further rearrange into xanthone to produce various classes of natural products. The structures of the new and unusual natural products are presented. Many of the metabolites also exhibit cytotoxic effect against murine leukemia P388 cells.
From the stem ofCudrania tricuspidata, β-sitosterol, β-sitosterol glucoside, arthocarpesin, norarthocarpetin, and 5-O-methyl genistein were isolated and characterized
by spectral data.
A simple bioautographic techniqud according to WELTZIEN', and modified by
DEISHUI JZEN~ for detection of fungitoxic substances has been in use for many years
in this laborattiry. Chromatograms on Whatman No. 3MM paper are develpped with
propanol-water (85: 15) and after drying are sprayed with a conidial suspension of
Glomerella cingzclata. After incubation, clearly visible inhibition zones indicate the
preserice of. fungitoxic compounds. Chromatography thus permits not only the detection
sf fungitoxic substances per se, but also makes the study of the conversion
reactions and of decomposition of such compounds possible.
The inhibitory effects of methanol extracts of heartwood of 23 Papua New Guinean wood species on tyrosinase activity were examined. The extract of Artocarpus incisus showed the strongest tyrosinase inhibitory activity which was equivalent to kojic acid. The extract apparently inhibited melanin biosynthesis of both cultured B16 melanoma cells without any cytotoxicity and in the back of a brown guinea pig without skin irritation. Thus, the potentiality of the extracts of heartwood of A. incisus both as material of a useful skin whitening agent and as a remedy for disturbances in pigmentation is evident. Tyrosinase inhibitory activity-guided fractionation led to the isolation of seven active compounds including a new compound which has been characterized as 6-(3"-methyl-1"-butenyl)-5,7,2',4'-tetrahydroxyflavone, named isoartocarpesin. Other active compounds were (+)-dihydromorin, chlorophorin, (+)-norartocarpanone, 4-prenyloxyresveratrol, artocarbene, and artocarpesin, These compounds are probably responsible for the melanin biosynthesis inhibitory effects.
The methanol extract of heartwood of Artocarpus incisus showed potent 5 alpha-reductase inhibitory activity. We investigated the 5 alpha-reductase inhibitory effects of nine compounds isolated from A. incisus. Chlorophorin (IC50 = 37 microM) and artocarpin (IC50 = 85 microM) showed more potent inhibitory effects than did alpha-linolenic acid, which is known as a naturally occurring potent inhibitor. Structure-activity investigations suggested that the presence of an isoprene substituent (prenyl and geranyl) would enhance 5 alpha-reductase inhibitory effects.
Eight compounds including, phenyl-beta-naphthylamine (1), isocyclomorusin (2), cycloartocarpin (3), artocarpin (4), norartocarpetin (5), cudraflavone C (6), albanin A (7), and resveratrol (8) were isolated from the roots of Artocarpus gomezianus. Compounds 5 and 8 exhibited potent tyrosinase inhibitory activity. The 1H- and 13C-NMR properties of 1, 3 and 8 were extensively studied.
Antimalarial activity-guided study of the aerial parts of Artocarpus integer led to the isolation of the prenylated stilbene, trans-4-(3-methyl-E-but-1-enyl)-3,5,2',4'-tetrahydroxystilbene with an EC50 of 1.7 micrograms/ml against Plasmodium falciparum in culture. The known stilbenes, trans-4-isopentenyl-3,5,2',4'-tetrahydroxystilbene and 4-methoxy-2,2-dimethyl-6-(2-(2,4-dihydroxy)phenyl-trans-ethenyl)chromene , were also isolated. Structures of these compounds were deduced on the basis of their spectral data.
The essential oil of black cumin seeds, Nigella sativa L., was tested for a possible antioxidant activity. A rapid evaluation for antioxidants, using two TLC screening methods, showed that thymoquinone and the components carvacrol, t-anethole and 4-terpineol demonstrated respectable radical scavenging property. These four constituents and the essential oil possessed variable antioxidant activity when tested in the diphenylpicrylhydracyl assay for non-specific hydrogen atom or electron donating activity. They were also effective.OH radical scavenging agents in the assay for non-enzymatic lipid peroxidation in liposomes and the deoxyribose degradation assay. GC-MS analysis of the essential oil obtained from six different samples of Nigella sativa seeds and from a commercial fixed oil showed that the qualitative composition of the volatile compounds was almost identical. Differences were mainly restricted to the quantitative composition.
Two new benzofuran derivatives, macrourins A (1) and B (2), together with two known stilbene derivatives, were isolated from the barks of Morus macroura Miq. Their structures were elucidated by means of spectroscopic evidence.
Fractionation of an ethyl acetate-soluble extract of the bark of Artocarpus dadah has led to the isolation of three new prenylated stilbenoid derivatives, 3-(gamma,gamma-dimethylallyl)resveratrol (1), 5-(gamma,gamma-dimethylallyl)oxyresveratrol (2), 3-(2,3-dihydroxy-3-methylbutyl)resveratrol (3), and a new benzofuran derivative, 3-(gamma,gamma-dimethylpropenyl)moracin M (4), along with six known compounds, oxyresveratrol, (+)-catechin, afzelechin-3-O-alpha-L-rhamnopyranoside, (-)-epiafzelechin, dihydromorin, and epiafzelechin-(4beta-->8)-epicatechin. From an ethyl acetate-soluble extract of the twigs of the same plant were isolated compound 4 and two new neolignan derivatives, dadahols A (5) and B (6), as well as 10 known compounds, oxyresveratrol, (+)-catechin, afzelechin-3-O-alpha-L-rhamnopyranoside, resveratrol, steppogenin, moracin M, isogemichalcone B, gemichalcone B, norartocarpetin, and engeletin. The structures of compounds 1-6 were determined using spectroscopic and chemical methods. Isolates were evaluated for their inhibitory effects against both cyclooxygenase-1 (COX-1) and -2 (COX-2) and in a mouse mammary organ culture assay.
A MeOH/CH(2)Cl(2) extract of the bud covers of Artocarpus altilis collected in Micronesia showed activity in a cathepsin K inhibition assay. In addition to the three known flavonoids isolated from the bud covers of this species, two new compounds have been identified whose structures were determined on the basis of spectral data. These compounds include a dimeric dihydrochalcone, cycloaltilisin 6 (2), and a new prenylated flavone, cycloaltilisin 7 (3). Novel compounds 2 and 3 have IC(50) values of 98 and 840 nM, respectively, in cathepsin inhibition.
Antifungal activity-guided fractionation of the n-butanol extract from the methanol extract of the stem bark of Artocarpus nobilis furnished two stilbene derivatives (E)-4-isopentenyl-3,5,2',4'-tetrahydroxystilbene and (E)-4-(3-methyl-E-but-1-enyl)-3,5,2',4'-tetrahydroxystilbene. Both compounds showed strong antifungal activity against Cladosporium cladosporioides and high radical scavenging activity towards the DPPH radical in TLC bio-autography method.
From the leaves of Millettia erythrocalyx, a new flavone named 3',5'-dimethoxy-[2",3": 7,8]-furanoflavone and three known compounds were isolated. Assays for anti-herpes simplex virus activity (HSV-1 and HSV-2) were performed on 24 phenolic compounds obtained from M. erythrocalyx and Artocarpus lakoocha. It was found that the flavones ovalifolin, pongol methyl ether and millettocalyxin A, and the stilbene oxyresveratrol possessed moderate activity against both types of HSV. In addition, oxyresveratrol was evaluated for potential anti-HIV activity against a wild-type human immunodeficiency virus type 1 (HIV-1/LAI) isolate and was found to be a modest inhibitor of HIV (EC50 28.2 microM), showing no toxicity in PBM, CEM and Vero cells at 100 microM. The heartwood of A. lakoocha, which contains a large amount of oxyresveratrol, could be considered as a source of starting material for the development of new natural product-based anti-HSV and anti-HIV agents.
Phytochemical investigation of roots and rhizomes of Veratrum taliense yielded a new and six known steroidal alkaloids as well as a new and one reported stilbene derivative. By a combination of spectral methods (IR, MS, (1)H- and (13)C-NMR, COSY, HMQC, HMBC, and NOESY), the structure of the new alkaloid was established as 15-angeloylgermine while the known ones were identified as 15-(2-methylbutyroyl)germine, jervine, 3-veratroylzygadenine, germine, veramiline 3- O-(beta- D-glucopyranoside and stenophylline B-3- O-beta- D-glucopyranoside. The new stilbenoid, named veraphenol, was determined to be 2-(3',5'-dihydroxyphenyl)-6-hydroxybenzofuran, and the known one was shown to be resveratrol. The IN VITRO enzyme assay indicated that 3-veratroylzygadenine and resveratrol are inhibitors of xanthine oxidase. The enzyme inhibitory action of resveratrol, the most active compound found so far in V. TALIENSE, is dose-dependent with the IC (50) value at 30 microM (the IC (50) value of allopurinolused as a positive control in the study is 10 microM).
Five geranyl dihydrochalcones, 1-(2,4-dihydroxyphenyl)-3-{4-hydroxy-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo[b,d]pyran-5-yl}-1-propanone (2), 1-(2,4-dihydroxyphenyl)-3-[3,4-dihydro-3,8-dihydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone (4), 1-(2,4-dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(3,4-epoxy-4-methyl-1-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone (5), 1-(2,4-dihydroxyphenyl)-3-[8-hydroxy-2-methyl-2-(4-hydroxy-4-methyl-2-pentenyl)-2H-1-benzopyran-5-yl]-1-propanone (8), and 2-[6-hydroxy-3,7-dimethylocta-2(E),7-dienyl]-2',3,4,4'-tetrahydroxydihydrochalcone (9), along with four known geranyl flavonoids (1, 3, 6, 7), were isolated from the leaves of Artocarpus altilis. Their structures were established by spectroscopic means and by comparison with the literature values. Compounds 2, 4, and 9 exhibited moderate cytotoxicity against SPC-A-1, SW-480, and SMMC-7721 human cancer cells.
- C Boonlaksiri
- W Oonanant
- P Kongsaeree
- P Kittakoop
- M Tanticharoen
- Y Thebtaranonth
- M Burtis
- F Bucar
- N Djapic
- Z Djarmati
- S Filip
- R M Jankov
- E H Hakim
- S A Achmad
- L D Juliawaty
- L Makmur
- Y M Syah
- N Aimi
- M Kitajima
- H Takayama
- E L Ghisalberti
Boonlaksiri, C., Oonanant, W., Kongsaeree, P., Kittakoop, P., Tanticharoen, M., Thebtaranonth, Y., 2000. Phytochemistry 54, 415.
Burtis, M., Bucar, F., 2000. Phytother. Res. 14, 323.
Djapic, N., Djarmati, Z., Filip, S., Jankov, R.M., 2003. J. Serb. Chem. Soc. 68, 235.
Hakim, E.H., Achmad, S.A., Juliawaty, L.D., Makmur, L., Syah, Y.M., Aimi, N., Kitajima, M., Takayama, H., Ghisalberti, E.L., 2006. J. Nat. Med.
60, 161.
- A L Homans
- A Fuchs
Homans, A.L., Fuchs, A., 1970. J. Chromatogr. 51, 327.
- U L B Jayasinghe
- S Puvanendran
- N Hara
- Y Fujimoto
Jayasinghe, U.L.B., Puvanendran, S., Hara, N., Fujimoto, Y., 2004. Nat. Prod. Res. 18, 571.
- A Kijjoa
- H M Cidade
- M M M Pinto
- M J T G Gonzalez
- C Anantachoke
- T E Gedris
- W Herz
- K Likhitwitayawuid
- B Sritularak
- W De-Eknamkul
Kijjoa, A., Cidade, H.M., Pinto, M.M.M., Gonzalez, M.J.T.G., Anantachoke, C., Gedris, T.E., Herz, W., 1996. Phytochemistry 43, 691.
Likhitwitayawuid, K., Sritularak, B., De-Eknamkul, W., 2000. Planta Med. 66, 275.
- K Likhitwitayawuid
- B Sritularak
- K Benchanak
- V Lipipun
- J Mathew
- R F Schinazi
- C.-N Lin
- C.-M Lu
- P.-L Huang
Likhitwitayawuid, K., Sritularak, B., Benchanak, K., Lipipun, V., Mathew, J., Schinazi, R.F., 2005. Nat. Prod. Res. 19, 177.
Lin, C.-N., Lu, C.-M., Huang, P.-L., 1995. Phytochemistry 39, 1447.
- J L Mclaughlin
- M S Rogers
- J E Anderson
McLaughlin, J.L., Rogers, M.S., Anderson, J.E., 1998. Drug Inf. J. 32, 513.
- C Boonlaksiri
- W Oonanant
- P Kongsaeree
- P Kittakoop
- M Tanticharoen
- Y Thebtaranonth
- M Burtis
- F Bucar
- N Djapic
- Z Djarmati
- S Filip
- R M Jankov
Boonlaksiri, C., Oonanant, W., Kongsaeree, P., Kittakoop, P., Tanticharoen, M., Thebtaranonth, Y., 2000. Phytochemistry 54, 415.
Burtis, M., Bucar, F., 2000. Phytother. Res. 14, 323.
Djapic, N., Djarmati, Z., Filip, S., Jankov, R.M., 2003. J. Serb. Chem. Soc. 68, 235.
- E H Hakim
- S A Achmad
- L D Juliawaty
- L Makmur
- Y M Syah
- N Aimi
- M Kitajima
- H Takayama
- E L Ghisalberti
Hakim, E.H., Achmad, S.A., Juliawaty, L.D., Makmur, L., Syah, Y.M., Aimi, N., Kitajima, M., Takayama, H., Ghisalberti, E.L., 2006. J. Nat. Med.
60, 161.
- B.-N Su
- M Cuendet
- M E Hawthorne
- L B S Kardono
- S Riswan
- H H S Fong
- R G Mehta
- J M Pezzuto
- A D Kinghorn
Su, B.-N., Cuendet, M., Hawthorne, M.E., Kardono, L.B.S., Riswan, S., Fong, H.H.S., Mehta, R.G., Pezzuto, J.M., Kinghorn, A.D., 2002. J. Nat.
Prod. 65, 163.