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Isolation and Identification of some Polar Compounds from Helichrysium Cyomsum

ISOLATION AND IDENTIFICATION OF SOME POLAR COMPOUNDS FROM

HELICHRYSIUM CYOMSUM

Background

Medicinal plant has provided the medical field with varies amount of new molecule.

The use of plant as medicine has being in practice since before 3000 B .C , since then medicinal plants has been documented by each country throughout history (Raskin & Ripoll 2004 ). The extended history of medicinal plant is a good indication that plant do possess the potential to provide large amount of new chemical entity to fight the outbreak of disease in the world.

Further evidence of its significance according to (Ashour, et al.

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, 2013) half of the best -selling pharmaceuticals in 1991 were either from natural products or derivative analogues.

Medicinal plant is preceded important in developing countries, for its primary health care, due to its acceptability culturally, compatibility with the human body but also its contains less side effect compared to the synthetics that are regarded as unsafe to human s and environment (Vinha , et al., 2012; Nag , et al., 2013; Popoola, et al., 2013) .

In South Africa, 70 -80% of the rural population consults traditional healers for the most illness on a regular basis. This is mostly due to due to it accessibility and affordability (Jager et al., 1996) . The combination of traditional and western medicine is becoming increasingly important (Meissner, 2004). Medicinal plants have curative properties due to the presence of important bioactive constituents (such as phenolics, flavonoids, alkaloids, tannins, and terpenoids) known as secondary metabolites that have a certain physiological action in the human body (Shaukat, e t al., 2013).

The isolation of plant metabolites started in the nineteenth century.

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At the beginning, structural elucidation of isolated compounds was limited by the technology available at that time, it was done by classical and exhaustive degradative methods and the structures emanated from such were confirmed through synthesis then followed by biological activity determinations.

Advancement of technology has made it possible for the structural classification of chemical compounds to be done with only a few milligrams of pure material using sophisticated instruments such as High -performance liquid chromatography (HPLC ), Nuclear magnetic resonance (NMR ) and High -resolution mass spectrometry ( HRM S) with many new compounds generated each year .

Some of these compounds are anti -malarial, anti -aging, anti -cancer , enzyme inhibitors and some are known to bind to specific receptors of pharmacological interest. However, there are some compounds isolated through chemically guided isolation that have prov ed to be bio logically active.

Problem statement

This study would investigate how to isolate some of the polar compounds in an extracted fraction of Helichrysium cymsum . The compound isolated would be identified using nuclear magnetic resonance .

Hypothesis

The NMR can be used to isolate and identify polar compound s form plant extract Helichrysium cymsum.

Assumption

There would be more than one pure polar compound identified and would have some medicinal properties.

Delimitation

Exploration of the isolated compound against any diseases. Conduct any comparative phytochemical and biological analyses on the isolated chemical constituents present in the Helichrysium species.

Literature Review

Asteraceae family

Asteraceae is the largest flowering family in the world, containing 23600 species allocated to 1620 genera and have an international distribution, but is especially diverse in the tropical and subtropical regions of southern Africa, the Mediterranean region, central Asia, south -western China, and Aust ralia (Funk, et al., 2009).

Although the vegetation can vary, it can be recognised in which numerous small flowers open first on the outside and only sometimes subtended by bracts. The anthers are fused and form a tube through which the style extends before the two stigmatic lobes separate and be come recurved, while the single -seeded fruit usually have a plumose pappus (Galbany -casals, et al., 2014).

The Asteraceae family is divided into 13 subfamilies (Panero, et al., 2014) of which the Asteroidea contains more than 70 % of the species currently recognised. Recent molecular studies discovered three main lineages within the Asteroideae that have been recognised at the super -tribe level (Robinson, 2004).

Helichrysium genus

Helichrysium is classified in the tribe Gnaphalieae , which is known to be the largest flowing plant . It currently contains 500 -600 species which are mainly found in Africa and Madagascar, but also in Europe, Asi a and Australia (Hilliard, 1983; Manning & Goldb att , 2012) . 240 -250 species occur in southern Africa of which approximately 70 -80 species are found in the uKhahlamba Drakensberg Mountains in KwaZulu – Natal and in the Eastern Cape region in South Africa. Due to massive morphological diversity the genus has been subdivided into 30 morphological groups based on the shape and the size of the flower heads (Hilliard 1983 ; Pooley 1998; Pooley 2003) .

South Africa Helichrysium species is associated with the treatment of infection of the skin, such as circumcised wounds and wound dressing (Loure ns, et al., 2008).

Helichrysium species has proven to contain secondary metabolites , like phenolic, ?- pyrone derivatives, and acetophenones derivatives (Lourens, et al., 2008), which give s them global acceptability due to the large application in the cosmetic and pharmaceutical fields acting as anti -inflammatory (Viegas, et al., 2014) , antibacterial and antioxidant agents (Kolayli, et al., 2010; Mari, et al., 2014; Rigano, et al., 2014).

Commercially drugs derived from this genus was used as a liver stimulant , diuretic. It can act as an anti -inflammatory, tissue re -generating property and treatment for some cardiovascular conditions (Kladar, et al., 2015).

Skin anti-ageing properties of Helichrysium species

Chemistry of metal -chelating ability of flavooids with copper (II) in tyrosinase has been studied with mild inhibitory activities demonstrated with compoun d H. Larix , H. acucatum, H. kraussii, H. oreophilum, H. cymosu m & H. bracteatum. Other prior activity of anti -tyrosinase data documented, were carried out using extracts obtained from plant materials. However, details of the mechanism of chelation between copper (II) and the chemical constituents of Helichrysium species remain untraceable in the Sci Finder database.

Antioxidant activities of Helichrysium genus

The antioxidants activities of this genus were directed towards fraction obtained from the crude plant materials. However, the compound responsible for this has only be documented in a few cases (Albayrak, et al., 2010 ).

A medicinal plant in the Mediterranean region was found to have good antioxidant activity using th e2,2 -diphenyl -1-picryl hydra zyl (DPPH ) assay with the Ion Chromatography 50 (IC 50) value 100 -fold higher than Trolox. It has an adequate amount of anti -aging properties due to its skin tissue regeneration ability and its alleviation of inflammation through its antioxidant properties, protecting the skin from the damaging effect of free radicals ( Orn ano, et al., 2015) .

H. Cymosum sp . cymosum

The main species (fig 1) is a shrub that usually grows up to 1m tall standing erect with thin greyish -white woolly branches densely covered wi th leaves. The upper surface of the leaf is covered in thin silvery grey, paper -like hairs. It has a bright yellow canary in flat -topped flo werheads . Each flowerhead is a cluster of 6 -20 flowers. The flowers generally have smooth tips, and a pappus of many bristles . H. cymos um subsp. cymos um has been recorded from the Cape point upward through the Eastern Cape and K ZN all along the coast.

Figure 1: A flowing shrub of H. cym sum sp. Cymsum

Three chemical constituents have been isolated from H. cymo sum subs p. Cymosum . Firstly, heli humulone (fig1 a), an oily phloroglucinol derivative with substantial antimicrobial activity. The other specie isolated is 5 -hydroxy -8-methoxy -7- prenyoxyflavanone (fig b). Lastly , a flavone derivative , helichromanochalcone (fig c) which was isolated from the roots ( Jakupovic et al. 1989 ; Van Vuuren et al. 2006)

This subspecies differs from H. cymosum so cy mo sum on that it has a narrower leaf and the branches are more densely clustered with its flowing head being smaller that that of H. cymosum sp. cymosum . It can be differentiated by its glabrous ovaries. It can be found in the Eastern Cape and K ZN. It only grows in areas that are higher than 1200m above sea level up to a maximum of 3170m (Hillard 1983; Pooley 1998).

This species is known to contain several flavonoid derivative compounds and a few terpene compounds (Bohlmann et al ., 1979) .

Figure 3: A flowing shrub of H. cymosum sp . clavum

Methodology

Plant collection

The Plant was collected at Hout bay Seaside Cape town South Africa. The study would only focus on an extracted fraction of the plant. It was prepared and stored at Cape Peninsula University of Technology (CPUT).

Column chromatography

A sub -fraction of plant extracted, was extracted by column chromatography using ethanol (mobile phase) which was performed in sephadex as the stationary phase, supported with glass column of different sizes.

Thin layer chromatography (TLC)

Visualization of TLC plates was done by observing the bands “spots” after development under UV at ?254 nm and ?366 nm using UV lamp followed by dipping into vanillin/sulphuric acid reagent.

Chemical profiles of the fractions were identified  based on the colour produced after viewing under UV and then spraying with the spray detecting reagent (vanillin/sulphuric).

Material and instrument

Extraction would take place at the CPUT laboratory with the use of column chromatography for extraction and nuclear magnetic resonance (NMR) to identify the isolated compound.

Schedule

The project is estimated to take at least three month of laboratory work. The practical aspect of it would be preformed at least once a week.

Budget

  • Column chromatography
  •  TLC plate
  • Ethanol
  • Methanol
  • Dich loromethane
  • Acetone
  • Rotary
  • Vanillin
  • Ultra -violet light
  • NMR

Reference

  • Albayrak, S., Aksoy, A., Sagdic, O. and Budak, U. (2010). Phenolic compounds and antioxidant and antimicrobial properties of Helichrysum species collected from eastern Anatolia, Turkey. Turkish Journal of Biology, 34(4), pp. 463 -473 .
  • Ashour, A., El -Sharkawy, S., Amer, M., Bar, A.F., Kondo, R. and Shimizu, K. (2013). Melanin biosynthesis inhibitory activity of compounds isolated from unused parts of Ammi visinaga. Journal of Cosmetics, Dermatological Sciences and Applications, 3, pp. 40 -43.
  • Bohlmann, F., Abraha m W -R., 1979. Neue diterpene aus Helichrysum acutatum . Phytochemistry 18, 1754 -1756.
  • Funk V.A., Susanna, A., Stuessy, T.F. and Robinson, H. (2009). Systematics, evolution and biogeography of the compositeae. International Association of Plant Taxonomy , Vienna.
  • Galbany -casals, M., Unwin, M., Garcia -Jacas, N., Smissen, R.D., Susanna, A. and Bayer, R.J. (2014). Phylogenetic relationship in Helichrysum (Compositae, Gnaphalieae) and related genera: Incongruence between nuclear and plastid phylogenies, biogeographic and morphological patterns, and implications for generic delimitations. Taxon, 63, pp. 608 -624 .
  • Hilliard, O. (1983). Asteraceae. In Leistner, O.A. flora of Southern Africa. Pretoria: Botanical Research Institute of South Africa .
  • J?ger, A.K., Hutchings, A ., and Van Staden, J. 1996. Screening of Zulu medicinal plants from prostaglandin -synthesis inhibitors. Journal of Ethnopharmacology 52, 95 – 100 .
  • Jakupovic, J., Kuhnke, J., Schuster, A., Metwally, M . A., Bohlmann, F., 1986. Phloroglucinol derivatives and other constituents from South African Helichrysum species . Phytochemistry 25, 1133 -1142.
  • Jakupovic, J., Pathak, V.P., Bohlmann, F., King, R.M. and Robinson, H. (1987 ). Obliquin derivatives and other constituents from Australian Helichrysum species. Phytochemistry , 26(3), pp . 803 -807 .
  • Kolayli, S., Sahin, H., Ulusoy, E. and Tarhan, O. (2010). Phenolic composition and antioxidant capacities of Helichrysum plicatum. Journal of Biology and Chemistry , 38(4), pp. 269 -276.
  • Mari, A., Napolitano, A., Masullo, M., Pizza, C. an d Piacente, S. (2014). Identification and quantitative determination of the polar constituents in Helicrysum italicum flowers and derived food supplements. Pharmaceutical and Biomedical Analysis , 96, pp. 249 -255.
  • Meissner, O. (2004). Editorial: The traditional healer as part of the primary health care team? South African Medical Journal, 94, pp. 901 -902.
  • Ornano, L., Venditti, A., Sanna, C., Balle ro, M., Maggi, F., Lupidi, G., Bramucci, M., Quassinti, L. and Bianco, A. (2015). Chemical composition and biological activity of the essential oil from Helichrysum microphyllum Cambess. ssp. tyrrhenicum Bacch., Brullo e Giusso growing in La Maddalena Arch ipelago, Sardinia. Journal of Oleo Science , 64(1), pp. 19 -26.
  • Panero, J.L., Freire, S.E., Espinar, L.A., Cr ozier, B.S., Barboza, G.E. and Cantero, J.J. (2014). Resolution of deep nodes yields an improved backbone phylogeny and new basal lineage to study early evolution of Asteraeae. Molecular Phylogenetics and Evolution , 80, pp. 43 -53.
  • Pooley, E. (199 8). A Field Guide to Wild Flowers: KwaZulu -Natal and the Eastern Region , Natal Flora Publication Trust.
  • Pooley, E., 2003. Mountain flowers: A field guide to the flora of the Drakensberg and Lesotho, 1st ed. The Flora Publications Trust . Durban, pp. 44, 102 -110, 146 -157, 222 – 225.
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  • Robinson, H. (2004). New supertribes Helianthodae and Senecionade, for the subfamily Asteroidae (Asteraceae). Phytologia, 86, pp. 116 -120.
  • Shaukat, K., Ghazala, H.R., Hina, Y., Rehana, P., Hina, A., Huma, S., Kaneez, F. an d Maryam, A. (2013). Medicinal importance of Holoptela integrifolia (Roxb.) Planch – its biological and pharmacological activities. Natural Products Chemistry & Research , 2(1), pp. 1 -4.
  • Van Vuuren, S. F., Viljoen, A. M., Van Zyl, R. L., Van Heerden, F . R., Ba?er, K. H.C., 2006. The antimicrobial, antimalarial and toxicity profiles of helihumulone, leaf essential oil and extracts of Helichrysum cymosum (L.) D. Don subsp. cymosum. South Africa Journal of Botany 72, 287 -290.
  • Viegas, D.A., Palmeira -de -Oliveira, A. and Salgueiro, L. (2014). Helichrysum italicum : From traditi onal use to scientific data. Journal of Ethnopharmacology , 151, pp. 54 -65.
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Isolation and Identification of some Polar Compounds from Helichrysium Cyomsum. (2019, Nov 19). Retrieved from http://studymoose.com/isolation-and-identification-of-some-polar-compounds-from-helichrysium-cyomsum-essay

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