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Phytochemicals of Custard Apple (Annona squamosa)

Phytochemicals of Custard Apple (Annona squamosa). Akshata Kulkarni * , Bianca Smith † , Priyanka Chaudhary * * Department of Horticultural Sciences, Texas A&M University, College Station, TX-77843 † Department of Food Science, Texas A&M University, College Station, TX-77843.

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Phytochemicals of Custard Apple (Annona squamosa)

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  1. Phytochemicals of Custard Apple (Annona squamosa) Akshata Kulkarni *, Bianca Smith†, Priyanka Chaudhary * *Department of Horticultural Sciences, Texas A&M University, College Station, TX-77843 †Department of Food Science, Texas A&M University, College Station, TX-77843 Etiology, Uses, Pre-harvest, Post-harvest, Health benefits and Bioavailability

  2. Outline • Introduction : species and varieties • Nutritional Content • Uses of fruit parts • Phytochemicals • Pre-harvest : Pollination, Temperature, Soil • Post-harvest : Storage, Ripening • Health Benefits • Conclusion

  3. Introduction • Annona squamosais commonly known as: sugar apple or sweetsop or custard apple • Semi-deciduous tropical shrub tree in the Annonaceae family. • Native of tropical America and West Indies Morton, J., Sugar Apple. In Fruits of warm climates, Apple, S., Ed. Miami, FL, 1987; pp 69 - 72.

  4. Distribution • Tropical South America, Tropical Africa, Asia, parts of North America and Australia. • Extensive cultivation in India • Southern Mexico • Queensland, Aus • Phillipines, • Brazil • China • Egypt • Israel • West Indies • Bahamas, Bermuda Janick, J.; Paull, R. E., The Encyclopedia of Fruit and Nuts. In The Encyclopedia of Fruit and Nuts, Janick, J.; Paull, R. E., Eds.

  5. Common Species • Genus Annona consists of ninety one species (GRIN Species Records of Annona, USDA, ARS) • Annonasquamosa – most widely grown and commercially cultivated

  6. Annonasquamosa 1990 2000 2006 1932 1980 1940 1960 1970 1950 1926 http://www.newcrops.uq.edu.au/listing/species_pages_A/Annona_squamosa.htm

  7. Commercial varieties • The most common varieties of sugar apple cultivated are: - Mammoth - Barbados - Balangar - African Pride - BeniMazar, Washington - British Guiana Morton, J., Sugar Apple. In Fruits of warm climates, Apple, S., Ed. Miami, FL, 1987; pp 69 - 72.

  8. Nutritional Content • Good source of : fiber, manganese, ascorbic acid, vitamin B6. Morton, J., Sugar Apple. In Fruits of warm climates, Apple, S., Ed. Miami, FL, 1987; pp 69 - 72.

  9. Useful parts of Annona • Fruit: High nutritive value - Table Fruit - Confectionary treats - Milk shakes • Leaves: Treat ulcers and wounds, Anticancer properties Chen, Y.; Chen, J. W.; Wang, Y.; Xu, S. S.; Li, X., Food Chem. 2012, 135, (3), 960-966.

  10. Uses of the bark and seeds Bark: - Tonic for dysentery - Alleviate tooth aches Seeds: - Anti-diabetic properties - Treats lice - May cause abortions Chen, Y.; Chen, J. W.; Wang, Y.; Xu, S. S.; Li, X., Food Chem. 2012, 135, (3), 960-966.

  11. Phytochemicals • Acetogenins • Different plant parts • Leaves • Bark • Seeds • Fruits

  12. AnnonaceousAcetogenins • Group of secondary metabolites found in plants of Annonaceae family (Esposti, et al. 1994) • Terminal γ-lactone subunit (either saturated or unsaturated) • One to three tetrahydrofuran rings (THF) • Long aliphatic region with other functional groups

  13. AnnonaceousAcetogenins • Potential anticancer agents (Hopp et al 1998). • Mechanism of action- inhibition of NADH ubiquinone oxido-reductase (complex I) in mitochondrial electron transport systems, and inhibition of NADH oxidase in the plasma membranes of tumour cells (Hopp et al 1998). • A number of cytotoxic acetogenins have been isolated from different parts of Annona plant. Hopp, D. C.; Alali, F. Q.; Gu, Z.-m.; McLaughlin, J. L., Bioorganic & Medicinal Chemistry 1998, 6, (5), 569-575.

  14. Phytochemicals in bark • Bullatalicin-acetogenin having two nonadjacent tetrahydrofuran rings, has been isolated from the bark of Annona. • Potent and selective cytotoxic activities for certain human tumor cell lines with ED50 values as low as 10m7 mcg/ml (Singh, et al. 2012). • Bullatacinone - white needle like structure, identical to other reported acetogenins (squamone, squamoneacetate) Bullatacinone

  15. Phytochemicals in seeds • Annosquamins : mono tetra hydrofuran annonaceous acetogenin. • Three new adjacent bis-THF ring acetogenins, (2,4-cis and trans)-squamolinone, (2,4-cis and trans)-9-oxo-asimicinone, bullacin B (Araya et al 2002). • Other Annonaceous acetogenins: 12,15-cis-squamostatin-A and bullatacin (Chen, Y. et al, 2012)

  16. Phytochemicals in Fruits • Phytochemicals: Ascorbic acid, polyphenols ,Anthocyanins, carotenoids, Tannins. ( D. R Singh et all) • Antioxidant activity

  17. Phytochemicals in Fruits

  18. Phytochemicals in Leaves • Muricoreacin and Murihexocin -significant cytotoxicities among six human tumor cell lines with selectivities to the prostate adenocarinoma PC-3 and pancreatic carcinoma PACA-2 cell lines • Two other new Annonaceous acetogenins- annomuricine and muricapentocin-selectivities to the pancreatic carcinoma (PACA-2) and colon adenocarcinoma (HT-29) cell lines.(Geum-soog Kim et al)

  19. Pre-harvest • Pollination • Temperature • Soil

  20. Pollination • Flowers – hermaphrodite, showing protogynous dichogamy • Low self pollination • Environmental factors • Wind pollination low • Beetles - Nitidulid beetle • Humidity > 70% • Temperature Thakur, D. R.; Singh, R. N., Indian J. Hortic. 1965, 22, 10-18.

  21. Temperature • Day / night temperature - vegetative flush, dry matter (George and Nissen, 1987) • Vegetative flush - flowering • High temperature tropical conditions are not favorable for increase in fruit set; subtropical regions more suitable George, A. P.; Nissen, R. J.,Scientia Horticulturae 1987, 31, 269-274.

  22. Soil • Soil moisture stress - moderate reduction in fruit set (George and Nissen, 1987) • Salinity - decreased mass accumulation and root growth (Passos, V. et al, 2005) • Older seedlings were more salt tolerant as compared younger seedlings (two weeks old) George, A. P.; Nissen, R. J.,Scientia Horticulturae 1987, 31, 269-274. Passos, V. et al., Biologia Plantarum 2005, 49, (2), 285-288.

  23. Post-harvest • Storage • Ripening

  24. Post- harvest : Storage • Above 25 ˚C: fruits are vulnerable to fungal attack • Below15˚C : chilling injury. • Optimal conditions for custard apple storage: 15 and 20 ˚C • Normal ripening occurs between 15-30° C Broughton, W. J.; Guat, T., ScientiaHorticulturae1979, 10, (1), 73-82.

  25. Post-harvest treatments • Enzymatic browning reaction catalyzed by polyphenoloxidase (PPO). • Control of enzymatic browning during processing and storage is important to preserve the quality of fruit pulp. • Heating of pulp in open pan beyond 55°C impairs pulp flavor and often results in developing bitterness and unpleasant repulsive off flavor in the pulp (Sastry. 1961).

  26. Treatments T1 - Steam heating at 83°C for 2 min pulp (with seed) + citric acid (4.87g) to maintain acidity 0.5% + packing in HDPE pouches. T2 - Steam heating at 83°C for 2 min pulp (without seed) +citric acid (4.87g) to maintain acidity 0.5% + packaging in HDPE pouches. T3 - Seed separation by scooping method + maintain ascorbic acid 2000 ppm + citric acid 4.87 g to maintain acidity 0.5% and packaging in HDPE pouches. Storage condition: C1 = -18°C, C2 = - 4°C. • Effect of storage of custard apple pulp at – 4 and –18° C temperature up to 70 days on scores for sensorial quality of pulp appearance, color, flavor, taste, texture and overall acceptability increases from 7.25 - 8.20, 7.3 - 8.0, 6.0 - 7.25, 6.0 - 7.25, 6.25 - 7.0, and 6.30 - 7.5, respectively. (From treatment 1 to 3) • The application of heat facilitates molecule damage of constituents (nutrients) of pulp by denaturation of protein, evaporation of volatile constituents, and gelatinization of starchy material. This may lead to the changes in sensorial characteristics of the pulp like increased viscosity, loss of flavor and taste and change in color.

  27. Ripening Study • Naturally and artificially (CaC2-treated) ripened sugar apple (AnnonasquamosaL.) fruit cultivars ‘Fai’ and ‘Nang’ were investigated for antioxidant contents and properties Fig. 1. Morphology of sugar apple fruits cultivars ‘Fai’ (left) and ‘Nang’ (right

  28. Fig. 2. Ascorbic acid content in ripened sugar apple fruits cultivars ‘Fai’ and ‘Nang’ Fig. 3. Phenolics content in ripened sugar apple fruits cultivars‘Fai’ and ‘Nang’

  29. Fig. 4. Flavonoid content in ripened sugar apple fruits cultivars ‘Fai’ and ‘Nang’ Fig. 5. Reducing power ability in ripened sugar apple fruits cultivars ‘Fai’ and ‘Nang’

  30. Fig. 6. Chelating ability in ripened sugar apple fruits cultivars ‘Fai’ and ‘Nang’ Fig. 7. DPPH radical scavenging ability in ripened sugar apple fruits cultivars ‘Fai’and ‘Nang’

  31. Results • Phenolics in ‘Nang’ sugar apple were slightly higher than ‘Fai’ fruit • Flavonoids from CaC2-treated fruits in both varieties were slightly lower than those of naturally ripened one • In case of reducing power, there was similar ability found in both • For ferrous ion chelating, this ability was very low (0.01-0.02%), whereas DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical scavenging ability was very high (83-92%). Noichinda1, S. et al. Acta Hort. 875, ISHS 2010

  32. Health Benefits • Acetogenins - diabetes, tumor, high antioxidant and antimicrobial properties.

  33. Anti tumor properties • Seed extract • 12,15-cis-squamostatin-A (1) and bullatacin (2) (Chen et al 2012). • Activity against four human tumor cell lines, especially for MCF-7(IC50. 0.25 mg/ml) and HepG2 (IC50. 0.36 mg/ml)cells in vitro. • Inhibited growth of H22 tumor cells in mice, maximum inhibitory rate of 69.55% by oral administration.

  34. Anti- diabetic Properties • Diabetes mellitus was induced with streptozotocin–nicotinamide. • Graded doses of the aqueous leaf extracts were then administered in drinking water to normal and experimental diabetic rats for 12 days. • Aqueous leaf extracts lowered the fasting plasma glucose levels, significantly decreased the levels of blood glucose and increased the levels of serum insulin.(Shirwaikar, A. et al, 2004).

  35. Recent studies on A. squamosa seeds • Recent studies suggest A. squamosaseeds to possess potent proapoptotic characteristics for several human tumor cells. • However, there could be certain types of tumor cells which show resistance towards A. squamosaseed extracts. • These studies also suggest A. squamosaseeds to be of significant potential in cancer therapy and therefore needs more detailed study (Pardhasaradhiet al 2005).

  36. Recent studies on A. squamosa leaves • Present investigations are made to reveal the involvement of a quercetin in the antidiabetic and antiperoxidative effects of Annona squamosa leaf extract. • Quercetin-3-O-glucoside (characterized by UV, IR, MS and NMR analyses) - examined for its potential to regulate alloxan-induced hyperglycemia and lipid peroxidation (LPO) in rats. (Sunanda Pandal et al)

  37. Conclusion • Different parts of Annonapossess various phytochemicals with a tremendous health benefits. • Not much studies are done on their bioavailability • Thus study based on their bioavailabiltiy and meta analysis could help in exploring this fruit for its anti tumor, anti cancer properties.

  38. Thank You Questions?

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