Chemistry and medicinal properties of the Bakul (Mimusops elengi Linn): A review

India is one of the world's biodiversity hotspots and reports confirm that a great variety of fruiting trees are indigenous to this region of the world. Mimusops elengi Linn (family Sapotaceae) commonly known as Bakul is one such tree native to the Western Ghat region of the peninsular India. However, today this tree is also found growing in other parts of the tropical and subtropical regions of the world. The tree is of religious importance to the Hindus and finds mention in various mythological texts. The stem, barks, leaves and fruits are used in various Ayurvedic and folk medications to treat various ailments. In the prehistoric days the ripe fruits were an important source of diet but today no one knows of its dietary use as it is seldom used. Studies suggest the tree contains medicinally-important chemicals, particularly the triterpenes and alkaloids. Preclinical studies in the past five years have shown that the extracts prepared from Bakul possess antibacterial, antifungal, anticariogenic, free radical scavenging, antihyperglycemic, antineoplastic, gastroprotective, antinociceptive and diuretic effects, thus lending pharmacological support to the tree's ethnomedicinal uses in Ayurveda. In this review for the first time attempt is made at addressing the chemical constituents, medicinal uses and validated pharmacological observations of Bakul.     

Phytochemistry, traditional uses and pharmacology of Eugenia jambolana Lam. (black plum): A review

Eugenia jambolana Lam. (syn. Syzigium cumini (L.) SKEELS; S. jambolana DC; Family: Myrtaceae), commonly known as black plum or Jamun is a plant native to India. Annually the trees produce oblong or ellipsoid fruits (berries). They are green when raw and purplish black when fully ripe. The ripe fruits are sweetish sour to taste and are used to prepare health drinks, squashes, juices, jellies and wine. Studies have shown that the berries contain carbohydrates, minerals and the pharmacologically active phytochemicals like flavonoids, terpenes, and anthocyanins. Jamun is a plant with known ethnomedicinal uses. Before the discovery of insulin, Jamun was useful in the treatment of diabetes and is an integral part in the various alternative systems of medicine. Scientific studies have shown that the various extracts of Jamun possess a range of pharmacological properties such as antibacterial, antifungal, antiviral, anti-genotoxic, anti-inflammatory, anti-ulcerogenic, cardioprotective, anti-allergic, anticancer, chemopreventive, radioprotective, free radical scavenging, antioxidant, hepatoprotective, anti-diarrheal, hypoglycemic and antidiabetic effects. The present paper reviews these aspects and also addresses the lacunas in the existing knowledge.     

Phytochemistry and medicinal uses of the bael fruit (Aegle marmelos Correa): A concise review

Aegle marmelos, a plant indigenous to India has been used by the inhabitants of the Indian subcontinent for over 5000 years. The leaves, bark, roots, fruits and seeds are used extensively in the Indian traditional system of medicine the Ayurveda and in various folk medicine to treat myriad ailments. Bael fruits are of dietary use and the fruit pulp is used to prepare delicacies like murabba, puddings and juice. Bael fruits are also used in the treatment of chronic diarrhea, dysentery, and peptic ulcers, as a laxative and to recuperate from respiratory affections in various folk medicines. Scientific studies have validated many of the ethnomedicinal uses and reports indicate that the fruit possesses broad range of therapeutic effects that includes free radical scavenging, antioxidant, inhibition of lipid peroxidation, antibacterial, antiviral, anti-diarrheal, gastroprotective, anti-ulcerative colitis, hepatoprotective, anti-diabetic, cardioprotective and radioprotective effects. For the first time, this review critically assesses the nutritional values, phytochemistry and preclinical pharmacological properties of the bael fruit. Attempts are also made at emphasizing the dietary and pharmaceutical potential of bael fruit that has been largely underutilized and neglected.     

Phytochemistry, nutritional and pharmacological properties of Artocarpus heterophyllus Lam (jackfruit): A review

Artocarpus heterophyllus Lam, commonly known as the jackfruit tree and belonging to the family Moraceae, is an exotic tree originally native to the Western Ghats of India. The fruits are of dietary use and are an important source of carbohydrate, protein, fat, minerals and vitamins. The heart wood is a very durable timber and is used in the preparation of furniture. The bark, roots, leaves, and fruit are attributed with diverse medicinal properties and are used in the various traditional and folk systems of medicine to treat a range of ailments. Preclinical studies have shown that jackfruit possesses antioxidant, anti-inflammatory, antibacterial, anticariogenic, antifungal, antineoplastic, hypoglycemic, wound healing effects and causes a transient decrease in the sexual activity. Clinical studies have also shown that the decoction of the leaves possesses hypoglycemic effects in both healthy individuals and non-insulin-dependent diabetic patients. Phytochemical studies have shown that jackfruit contains useful compounds like the flavonoids, sterols and prenylflavones which may have been responsible for the various pharmacological properties. The present paper reviews the nutritional value, culinary uses, the phytochemical compounds, traditional usage and validated pharmacological properties of jackfruit.     

The antioxidant properties of the cherimoya (Annona cherimola) fruit

Annona cherimola is an exotic fruit from the genus Annona, native to the Andean highlands in western South America. The cherimoya skin, flesh and juice were isolated and analyzed for antioxidant content using the oxygen radical absorbance capacity (ORAC) assay. The juice showed the highest antioxidant activity, while the flesh exhibited the lowest. The cherimoya skin, flesh and juice extracts were also incubated with Raji (Burkitt's Lymphoma) and HT-29 (colon cancer) cell lines, and the antioxidant uptake of cells was measured. Both cell lines, when subjected to cherimoya juice, showed the highest antioxidant uptake. The cells were then exposed to AAPH, a radical initiator, to simulate the conditions of cells under oxidative stress, and then subjected to cherimoya skin, flesh and juice extracts. Both cell lines absorbed more antioxidants after being pre-exposed to AAPH, indicating that cells under stress have the ability to import antioxidants.     

Diallyl sulfides: Selective inhibitors of family X DNA polymerases from garlic (Allium sativum L.)

Diallyl sulfides, organosulfur compounds isolated from garlic (Allium sativum L.), selectively inhibit the activities of mammalian family X DNA polymerases (pols), such as pol β, pol λ and terminal deoxynucleotidyl transferase (TdT), in vitro. The purified fraction (i.e., Sample-A) consisted of diallyl trisulfide, diallyl tetrasulfide and diallyl pentasulfide (molecular ratio: 5.3:3:1). Commercially purchased diallyl sulfides also inhibited the activities of family X pols, and the order of their effect was as follows: Sample-A > diallyl trisulfide > diallyl disulfide > diallyl monosulfide, suggesting that the number of sulfur atoms in the compounds might play an important structural role in enzyme inhibition. The suppression of human cancer cell (promyelocytic leukaemia cell line, HL-60) growth had the same tendency as the inhibition of pol X family among the compounds. Diallyl sulfides were suggested to bind to the pol β-like region of family X pols.     

A review of botanical characteristics, phytochemistry, clinical relevance in efficacy and safety of Lycium barbarum fruit (Goji)

Lycium barbarum has been used as a traditional Chinese medicine (TCM) to nourish liver and kidney, and brighten the eye. The fruits are dried or freshly squeezed for their juice and concentrated for beverages. Among various constituents, a group of polysaccharides (LBP) with a Glycan-O-Ser glycopeptide structure has been most researched and considered to be important for the efficacy of L. barbarum. Studies indicate effects of L. barbarum on aging, neuroprotection, general well-being, fatigue/endurance, metabolism/energy expenditure, glucose control in diabetics, glaucoma, anti-oxidant properties, immunomodulation, anti-tumor activity and cytoprotection. In addition to TCM, L. barbarum can be sold as a dietary supplement or classified as a food based upon the long and safe traditional usage. This review is to provide background and updated information of chemical constituents and efficacies with safety including a new direction for research and current regulatory situation of L. barbarum.     

Isolation and evaluation of the antioxidant activity of phenolic constituents of the Garcinia brasiliensis epicarp

A new glycosylated biflavonone, morelloflavone-4′″-O-β-d-glycosyl, and the known compounds 1,3,6,7-tetrahydroxyxanthone, morelloflavone (fukugetin) and morelloflavone-7″-O-β-d-glycosyl (fukugeside) were isolated from the epicarp of Garcinia brasiliensis collected in Brazil. The structures of these compounds were established using ¹H and ¹³C NMR, COSY, gHMQC and gHMBC spectroscopy. The compounds exhibited antioxidant activity. The greatest potency was displayed by morelloflavone (2), with IC₅₀ = 49.5 mM against DPPH and absorbance of 0.583 at 400 μg/mL for the reduction of Fe³⁺. The weakest potency was displayed by 1,3,6,7-tetrahydroxyxanthone (1), with IC₅₀ = 148 mM against DPPH and absorbance of 0.194 at 400 μg/mL for the reduction of Fe³⁺.     

Elucidation of the flavonoid and furocoumarin composition and radical-scavenging activity of green and ripe chinotto (Citrus myrtifolia Raf.) fruit tissues,leaves and seeds

Citrus myrtifolia Raf. (chinotto) flavedo, albedo and carpel membranes from green and ripe fruits, as well as seeds and leaves, were investigated for the first time for their flavonoid and furocoumarin composition. Twenty-three unique compounds distributed in the different fruit/plant parts were identified and quantified. All samples analysed contained flavanone O-glycosides, flavone C- and O-glycosides and furocoumarins; flavedos and albedos also contained significant amounts of polymethoxyflavones. Flavedo and albedo extracts were found to be richest in flavonoids and furocoumarins, containing up to 1.95 g/kg fresh weight. Flavedo, albedo and carpel membranes from ripe fruits were found to be richer than the corresponding tissues from unripe fruits. The remarkable radical-scavenging activity of all the extracts was tested by DPPH^•, ABTS^•+ and FRAP methods, revealing that (i) they were particularly efficient in quenching ABTS^•+ radical cations (up to 9.8 mM Trolox equivalents), and (ii) flavedo and albedo extracts, on average, showed the highest antioxidant capacity.     

Purification and characterization of an antioxidant protein (∼16 kDa) from Terminalia chebula fruit

Terminalia chebula fruit is used as folk medicine in India and Southeast Asia. An antioxidant protein was isolated by bioassay guided fractionation of T.chebula fruit by homogenizing in the citrate phosphate buffer. The isolated protein (TCP-III) obtained from fruit was purified by gel chromatography and preparative HPLC, showed apparent molecular weight of 16 kDa by SDS-PAGE and MALDI-TOF/MS analyses. Amino acid sequence obtained by LC-MS^E analysis showed homology with the predicted protein fragments of Populus trichocarpa, putative uncharacterized protein fragments from Oryza sativa and with fragments of 17 kDa thylakoid lumenal protein from Spinacia oleracea. TCP-III exhibited significant radical scavenging in DPPH, NO, H₂O₂ and ABTS assays. In addition, TCP-III inhibited oxidation of linoleic acid in β-carotene bleaching assay, reduced ferric ions and chelated ferrous ions. The present finding demonstrates uniquely, for the first time, characterization of an antioxidant protein from T. chebula fruit.     

Cytotoxic effects of geranyl flavonoid derivatives from the fruit of Artocarpus communis in SK-Hep-1 human hepatocellular carcinoma cells

Breadfruit (Artocarpus communis) is cultivated in tropical and subtropical regions as a traditional starch crop. This study investigated the cytotoxic activity of geranyl flavonoid derivatives isolated from the fruit of A. communis. Two new geranyl flavonoid derivatives, arcommunol A and arcommunol B, together with four known compounds, were isolated from the fruit of A. communis. The effects of these compounds on the viability of HepG2, Hep3B, PLC5 and SK-Hep-1 cells were investigated. Arcommunol A showed the highest inhibitory activity with 2.05 μM IC₅₀ in SK-Hep-1 cells. Treatment with arcommunol A changed the ratio of expression levels of pro- and anti-apoptotic Bcl-2 family members and subsequently induced the activation of apoptosis-inducing factor, apoptotic protease activating factor-1, caspase-9 and caspase-3, which may result in a cleavage of poly(ADP-ribose) polymerase. These findings provide critical information regarding the chemopreventive potential of arcommunol A from the fruit of A. communis.     

Selected primary and secondary metabolites in fresh persimmon (Diospyros kaki Thunb.): A review of analytical methods and current knowledge of fruit composition and health benefits

Diospyros kaki Thunb. (Ebenaceae) is a widely cultivated tree species in some countries of Asia, while in other continents persimmons are mostly considered “exotic” fruits. Peculiar characteristics of this species are a complex sex expression, parthenocarpy and fruit astringency at harvest time, associated with a different composition in polymerized flavan-3-ols. Analytical methods for determining sugars, vitamin C, carotenoids and polyphenols in persimmons were critically reviewed in order to evaluate the overall significance of literature results; the nutritional and nutraceutical properties, together with the health benefits of both astringent and non astringent cultivars, were also overviewed. To these aims, the available literature from the last twenty years and the most important formerly published papers were investigated using SciFinder^®, Elsevier SciVerse, AGRIS, and PubMed search engines. Persimmons resulted rich in sugars (about 12.5 g/100 g FW), being fructose, glucose and sucrose the major components, and in total vitamin C, for which 100-150 g of fresh persimmon supplies the recommended daily amount. Astringent varieties supply higher amounts of sugars than nonastringent ones; conversely, higher concentrations of total vitamin C were found in nonastringent cultivars. The main carotenoid components are ??-cryptoxantin (193 ??g/100 g FW), ??,??-carotene (113 ??g/100 g FW) and ??,??-carotene (30 ??g/100 g FW). Persimmons are also a good source of polyphenolic compounds such as p-coumaric acid, catechin, epicatechin, epigallo catechin, and condensed proanthocyanidins. This chemical composition, together with in vivo and in vitro studies, suggests a relevant role of persimmon in the protection against free radicals and in the prevention of some human diseases.     

A phenolic antioxidant from the Pacific oyster (Crassostrea gigas) inhibits oxidation of cultured human hepatocytes mediated by diphenyl-1-pyrenylphosphine

3,5-Dihydroxy-4-methoxybenzyl alcohol (DHMBA), an antioxidant isolated from the Pacific oyster (Crassostrea gigas), was studied in a cell-based fluorometric antioxidant assay using human hepatocyte-derived cells (C3A) and diphenyl-1-pyrenylphosphine (DPPP) as a fluorescent probe. In comparison with two hydrophilic antioxidants, DHMBA showed the stronger inhibition of DPPP-mediated fluorescence than chlorogenic acid and l-ascorbic acid: at a concentration of 320 μM of DPPP, the inhibition was 26.4 ± 2.6%, 11.1 ± 1.2%, and 0 ± 2.0% for DHMBA, chlorogenic acid, and l-ascorbic acid, respectively (mean ± SD, n = 4). Their relative oxygen radical absorbance capacities (ORAC) were dissociated with their cell-based antioxidant activities: 1.47 ± 0.40, 4.57 ± 0.30, and 0.53 ± 0.13 μmol TE/μmol for DHMBA, chlorogenic acid, and l-ascorbic acid, respectively (mean ± SD, n = 4). The amphiphilicity of DHMBA was better than chlorogenic acid and l-ascorbic acid might underlie this dissociation. Since the C3A cells are human hepatoma-derived cells, DHMBA might be useful in the prevention and treatment of liver diseases by involving an oxidation process.     

Evaluation of the antioxidant and antiproliferative activities of extracted saponins and flavonols from germinated black beans (Phaseolus vulgaris L.)

Flavonoids and saponins from common beans have been widely studied due to their bioactivity. This research evaluated the effect of germination of black beans (Phaseolus vulgaris L.) on the antioxidant capacity and antiproliferative activity against cancer cell lines of saponins and flavonoids extracted from seed coats, cotyledons and sprouts. Principal component analysis was performed to achieve punctual associations between the black bean saponins and flavonoids concentrations to the antioxidant capacity and the antiproliferative activities. Total phenolic content and antioxidant capacity of extracts were higher when obtained from seed coats, mainly from the 3rd germination day. The extracts obtained from seed coats after 3 and 5 germination days inhibited all cancer cell lines proliferation with no cytotoxicity against control cells. Genistein was related with the activity against mammary cancer cells but flavonols and group B saponins were more related with hepatic and colon cancers. Non-glycosilated flavonols were related with antioxidant capacity.     

Isolation,characterization and antioxidant capacity assessment of the bioactive compounds derived from Hypoxis rooperi corm extract (African potato)

The rhizome of the plant Hypoxis rooperi (“African potato”) is known for its traditional and ethnomedical uses in the treatment of benign prostatic hyperplasia and other diseases. We have characterized an extract derived from H. rooperi, isolated its major bioactive compound, hypoxoside, and obtained its aglycone, rooperol, by enzymatic digestion. Absorption, fluorescence emission and bidimensional NMR complete spectral data of these compounds were obtained. The antioxidant capacity of both compounds was fully analyzed through the thiobarbituric acid reactive substances (TBARS) and Trolox equivalent antioxidant capacity (TEAC) assays, and it was compared to catechins and olive biophenolics. Both compounds showed a strong antioxidant capacity, although rooperol exhibited a higher antioxidant activity against lipid peroxidation which correlated to its strong affinity for phospholipid membranes as derived from its extremely high lipid/water partition coefficient (K_p = 3.4 × 10⁴). The study of the lipophilic (EtOH) and hydrophilic (water) TEAC values revealed that more hydrophobic compounds, had greater lipophilic TEAC values than hydrophilic ones, probably indicating that lipophilic TEAC assay may be more reliable for these compounds. The H. rooperi extract also showed higher antioxidant efficacy compared to other strong antioxidant herbal extracts, such as olive leaf or green tea. Moreover, neither evidence of acute oral toxicity nor adverse effects were observed when the H. rooperi commercial extract containing 45% hypoxoside was used at a dosage of 2000 mg/kg. The results obtained in this work may contribute to understanding the biological activity described for these dicatechols and the African potato extract for food and cosmetic applications.     

Physical, chemical and technological characteristics of Solanum lycocarpum A. St. - HILL (Solanaceae) fruit flour and starch

Fruit of wolf (Solanum lycocarpum A. St. - HILL), found in Brazilian cerrado, has been used in the initial ripening stage as flour and/or starch in popular medicine due to its hypoglycemiant action. The aim of this work was to study the occurrence of phytochemical compounds, physical, chemical and technological characteristics of fruit of wolf flour and starch in the initial ripening stage. Flour and starch were extracted using known popularly and experimental methods (with sodium bisulfite) and chemical composition and technological characteristics were analyzed. The results were comparatively assessed by Tukey's test (p < 0.05). The recommendation for use was the extraction of flour and starch products by previously removing peels and seeds of fruit of wolf. The most relevant finding in this study is the high content of fibers in flour (23 g/100 g) and high content of resistant starch (32 g/100 g) in the fraction of starch extracted from fruit of wolf, which can explain their use as hypoglycemic agent.     

Metabolic profile and biological activities of Lavandula pedunculata subsp. lusitanica (Chaytor) Franco: Studies on the essential oil and polar extracts

We investigated the metabolic profile and biological activities of the essential oil and polar extracts of Lavandula pedunculata subsp. lusitanica (Chaytor) Franco collected in south Portugal. Gas chromatography–mass spectrometry (GC–MS) analysis revealed that oxygen-containing monoterpenes was the principal group of compounds identified in the essential oil. Camphor (40.6%) and fenchone (38.0%) were found as the major constituents. High-performance liquid chromatography with diode array detection (HPLC–DAD) analysis allowed the identification of hydroxycinnamic acids (3-O-caffeoylquinic, 4-O-caffeoylquinic, 5-O-caffeoylquinic and rosmarinic acids) and flavones (luteolin and apigenin) in the polar extracts, with rosmarinic acid being the main compound in most of them. The bioactive compounds from L. pedunculata polar extracts were the most efficient free-radical scavengers, Fe²⁺ chelators and inhibitors of malondialdehyde production, while the essential oil was the most active against acetylcholinesterase. Our results reveal that the subspecies of L. pedunculata studied is a potential source of active metabolites with a positive effect on human health.     

Açaí (Euterpe oleraceae) ‘BRS Pará’: A tropical fruit source of antioxidant dietary fiber and high antioxidant capacity oil

This article reports a study of the concentrations of dietary fiber (DF) and antioxidant capacity in fruits (pulp and oil) of a new açaí (Euterpe oleraceae) cultivar—‘BRS-Pará’, with a view to determine the possibility of using it as a source of antioxidants in functional foods or dietary supplements. Results show that ‘BRS-Pará’ açaí fruits has a high content of DF (71% dry matter) and oil (20.82%) as well as a high antioxidant capacity in both defatted matter and oil. ‘BRS-Pará’ Açaí fruits can be considered as an excellent source of antioxidant dietary fiber. Antioxidant capacity of açaí ‘BRS-Pará’ oil by DPPH assay was higher (EC₅₀ = 646.3 g/g DPPH) than extra virgin olive oil (EC₅₀ = 2057.27 g/g DPPH). These features provide açaí ‘BRS-Pará’ fruits with considerable potential for nutritional and health applications.     

Mycosporine-like amino acid composition of the edible red alga, Palmaria palmata (dulse) harvested from the west and east coasts of Grand Manan Island,New Brunswick

The oxygen radical absorbance capacity (ORAC), antiproliferative activities and mycosporine-like amino acid (MAA) profiles of methanol extracts from two grades of dulse harvested from locations varying in UV-exposure (west vs east coasts of Grand Manan Island, NB) were determined in the present study. MAAs confirmed by LC/MS in both grades 1 (low-UV) and 2 (high-UV) dulse were palythine, shinorine, asterina-330, palythinol and porphyra-334; usujirene was present only in grade 2 dulse. ORAC values of grade 1 and 2 dulse extracts were 36.42 and 38.78 μmol Trolox/g extract. B16-F1 murine skin melanoma cell proliferation was inhibited (p < .05) by 68.5% and 91.9% by grade 1 and 2 dulse extracts at 6.0 mg/mL. The antiproliferative efficacy of grade 2 dulse was greater (p < .05) than grade 1 from 0.375 to 6.0 mg/mL. MAA differences between the grade 1 and 2 dulse extracts likely influenced the antiproliferative efficacies, despite the similar ORAC values.     

Identification and quantification by LC–MS/MS of a new precursor of 3-mercaptohexan-1-ol (3MH) using stable isotope dilution assay: Elements for understanding the 3MH production in wine

The isotopically labelled S-3-(hexan-1-ol)-glutathione d₂/d₃ (G3MHd₂/d₃) was synthesized with a strategy based on acid-labile protecting groups. The natural analogue of this compound could be a precursor of 3-mercaptohexanol, a varietal thiol reminiscent of grape fruit, released during alcoholic fermentation. In a first time, deuterated glutathione conjugate was used to perform identification and quantification by stable isotope dilution assay of G3MH in musts from several varieties: Sauvignon, Riesling and Gewurztraminer.