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Phytochemicaland Biowgical Studies on Goniothalamus Malayanus

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Phytochemicaland Biowgical Studies on Goniothalamus Malayanus PHYTOCHEMICALAND BIOWGICAL STUDIES ON GONIOTHALAMUS MALAYANUS Hamdan Bin Asfiar Bachelor of Science with Honours QIC 861 (Resource Chemistry) 8198 2005 2005 Pusat Khidmat Makiumat Akade UNIVERS1TI MALAYSIA SARAWA 94 ()() Kola Samarahan P.KHIDMA TMAKLUMATAKADEMIK UIIMAS 1111111111111111111111111 1000127066 PHYTOCHEMICAL AND BIOLOGICAL STUDIES ON GONIOTHALAMUS MALAYANUS HAMDAN BIN ASFIAR This project is submitted in partial fulfillment of the requirements for the degree of Bachelor of Science with Honours (Resource Chemistry) Faculty of Resource Science and Technology UNIVERSITI MALAYSIA SARAWAK 2005 DECLARATION No portion of the work referred to in this dissertation has been submitted in support or nn application for another degree of qualification of this or any other university or institution of higher learning. Hamdan bin Asfia r Program of Resource Chemistry Faculty of Resource Science and Technology Univcrsiti Malaysia Sarawak II ,..... ACKNOWLEDGEMENTS Firstly, to the God , for His Humanity and Power to His creatures to let me finished this tinal year project. Then , I would like to express my highest gratitude to my respective supervisor, Assoc. Prof. Dr. Fasihuddin Ahmad tor all invaluable guidance and suppOli in the fulfillment of thi s tinal year project and to all lectures for their precious information. This special acknO\",ledg~mcnt also goes to everyone who always giving me inspirations and hopes l:specially for the laboratory assistants for the help while working in the laboratory and to my fellow frit:nd s who always giving me information related to my project. Not forget, to my loving family who always praying for my success upon their prayer and support. III TABLE OF CONTENTS DECLARATION II ACKNOWLEDGEMENTS III TABLE OF CONTENTS IV ABSTRACT VI ABSTRAK VI CHAPTER 1: INTRODUCTION CHAPTER 2: LITERATURE REVIEW 3 CHAPTER 3: MATERIALS AND METHODS 8 3.1. Plant materials 8 3.2. General 8 3.3. Extraction 9 3.4. Isolation and purification 9 3.5. Structural determination II 3.6. Bioassay II 3.6.1. Brine shrimp toxicity test II 3.6.2. Antifungal toxicity test 12 CHAPTER 4: RESULTS AND DISCUSSION 13 4.1. Extraction, isolation and purification of G. 111l11uy anlls sample 13 4.2. Structural determination of isolated compounds 16 4.3. Brine shrimp toxicity test 17 IV 404. Antifungal toxicity test 20 CHAPTER 5: CONCLUSIONS AND RECOMMENDATIONS 24 REFERENCES 25 APPENDICES v Phytochemical and biological studies on Goniothalamus malayanus Hamdan bin Asfiar Resource Chemistry Faculty of Resource Science and Technology Universiti Malaysia Sarawak ABSTRACT Phytochemical and biological studies have been carried out on the stem bark of COlliol/wlUlIIIlS IIll1lc~\ ·( lI1l1s. In the study, extraction has been carried out using three different rypes of <;olvents; hexane, et hyl acetate and ethanol, followed by thlctionation and puri tication. Ethyl acetate crude ('xtract was subjected to Tl,C analysis and yielded 4 spots with Rr values of' 0.75. 0.81. 0.87 and 0.91 in dichlowmethane-ethyl acetate-acetone (4 :2: I) solvent system. For column chromatography, 19 combined Ira tions were obtained. Fraction GCO I was subJected to PTLC analysis ami resulted 3 compounds namely GCOI (i), GCOI (ii) and GCOI (iii) ',.\ith Rr values 01'0.77, 0.90 and 0.93. Compound GCOI (iii) was the most pure compound than GCOI (ii) and GCOI (iii) with the highest peak at retention time or '2_.799 min, Brine shrimp toxicity test performed on crude extracts and lI'actions revealed that crude extracts and ti'actions have low toxicity on Arlemia salina except for fraction GCO I which gave LC -II value of 100 pg/mL.. All the crude extracts also showed moderate toxicity against fungus PI'CI/OP0I'IIS spp. and .\"chi=ophyllunI comrnllne. Keywo rds: (JOl1iolhu/omlls ll1u/oYUI1US, phytochemical studies, column chromatography, thin layer chromatography, biological activity. ABSTRAK Kldial/ ,lilokill1i(/ d(/II hi%gi Iclah dija/ankon ke alas kulil hal({ng GrJlliolha/al11l1.1 I/w/am/ll/s. PmsL's /II!IIgl'kslrakulI ((:/ali Ji/akukan d(!llg011 lI1enggltnukUI1 3 j(!l1is edaml yang ha/uil/all iailll heksw/(J, eli/ lIsdal dun dallo/ diikuli dellgall proses pemfi'oksia/1 dall penll/enal1. Anu/isis KLN I(!/uh dilukllkul1 ke (flus rksll'lIk klislIr eli/ uselal dun --I lilik dmgull lIilaj R( {). 75. O.SI. 0.87 dan 0.91 £la/am sis/em p(!/al'lll Jik/oromelal1£1-c/i/ uselal-useIO// (4:2: I) telah dipero/ehi. Km/7/ulogr(!fi IlIrlIS Ie/ah Jnl!l71herikall ga/?lIngal1 /9 paksi. Frob-i CCr)f lelah dillji dengan sis/em KLNP meng/wsi/kun 3 kOI11/)()J1f! 1I dUll di/alle/aka" sehugui (J( 'f) I (i). C( '() / Oi) dOli ceo I (iii) dellgol/ jiJk(or pl:'lIu/llmUII 0. 77. a.l)() dUll U 93 lIl£lsillg-lJ1asingn,l'u. Sl!hulia/1 CCO I (i) ({datah sehalian YOllri paling fltll!n herhanJing (J( '0 I (ii) dUll (iC() / (iii) dl!ngan pUl1cok lerlinggi pm/a ni/oi jJellahonon 22.7W. Ujian keloksikall diia/ullk({1/ ke ulav eks/rak k(/sa/' dall .!i-aksi lIIell1l11jllkkan ke(oksikun .l'Ul1g renda/i ler/wdap Arleflliu .w/il1({ keel/u/i ./i'aksi (j( 'O J yal1g melllherikan LC,<II eae/a k(!pekalal1 I()() ,ug/tnL. K(!sel1ll/a ekslmk kuso/' jl/ga 1/1('//llIlil/kkulI kl.'/ok.\ ik£ll1yong sederhallalerhudap ku/al PI'CIIO[JOrtiS spp. and Sc/tiz()[Jhv//ul/1 COl1l1l1une. I\,I/a k1l116: (jolliol/1l1/0111I1S I//alavunlIS, kajial'l filakimia. kromalogl' !II III/,u.I'. kroll1ologro/i /api.IUlI l7iJlis. ;"i/i hi% gi. VI CHAPTER 1 INTRODUCTION GoniOfhlJ/alllus is the second largest genus of Annonaceae and comprises I 15 species of , hrubs and trees growing in Asia cspecially South-East Asia and many of them arc used in the t{ II,. medicine in sevcral countries (Surivct and Yatele. 1999). More than 150 taxa have becn desc ribcd in Gonioflw/lJn1us; about 120 species and 10 subspecies are currently recognized (Mat Sallch. 1993). Members orthe genus are widely used in traditionalmcdicinalpractices in Asia. Many novel and clinically bioactive compounds have been isolated from Gonioflia/lIl11us species (Mat Salleh. 1993). They are widely employed in traditional medicine. alone or as part of herbal mixtures. as post-partum protective remedies for women after delivery, abortifacients and insects' repellcnts (Seidel el a/., 2000). In Malaysia, a decoction of the roots is used for treating colds and likewise a steam bath IS Llsed for treating fevers. For example, Goniotha/an1l1s n1a/ayanlls is used as ab0l1iracient. treatment atter delivery, to cure headache, fever, diarrhea, measles and rheumatism (Mat Salleh and Ahmad, 1989 ; Latiff. 1991). A decoction of Goniofha/an1us l11ac;rophyllus roots is taken orally to stOp early prcgnancy and as protective drugs after childbirth (Wiart. 2000). (ioniofha/amlls n1a/ayalllls and Goniolha/amus scorlechinii are believed to be effective as agents of abortion or contraception (Mat Salleh, 1993). Goniotha/an1l1s curfisii is one of the most popular concoctions for the treatment of stomachaches (Mat Salleh, 1993). Plant parts from some species of this genus have been used traditionally as insecticides. The smoke from the barks can be used to repel mosquitoes, snakes and other wild animals. ror e .Imple. the bark of (joniotha/ol11l1s macrophyllus is used to repel mosquitoes (Secoy and Sm ith. J983 ; Morton, 1987). The fragrance associated with the stems of Gvnio/halamus, c pecially GOl7io/halamlls vell//inus is said to keep away bad spirits and dangerous wild animals 'uch as snakes, elephants or tigers (Mat Salleh, 1993). Most of the Gonio/halamlls are concentrated in Borneo with high percentage of endemics. Borneo has a remarkable representation of the richness and diversity of the genus (Mat Salleh. 19(3). A total of 30 species, including new species, of the genus are recogn,ized from Borneo. Twenty four species are local endemics and 10 species from Borneo are known from very few localities. This shows that most of the Gonio/halumus species are locally evolved in Borneo. Some of the Gvnio/hulamus species are Goniv/haLamus m alayan us, Goniv/haLaml/s Kigunlells. GOl1io/halamLis uvaroides. Gonio/haiamlls do/ichvcarpus, Gvnio/huiwl1us jt,,\'(:icl1luntus. Gonio/halamus tomcn/OSlIS, Goniv/haial1111S lapis. Goniothalall1l1s macroph.vllus. (ionio/halal11l1s s/el/ope/aILls, Goniothalamus c1emensii and Gvniv/haiamus montanus. The objectives of this project are to isolate, purify and characterize biological active compounds frol11 GOl1io/halamus malayanus and to perform toxicities studies on brine shrimp, Ar/emill salina and fungus, Pycnopol'1ls spp. and SchizophvLLum CO/11/1l/.l/1 e. 2 ,.... r CHAPTER 2 LITERATURE REVIEW (joniofhuIUf11I1S maluyantls Hook f. & Thoms is a small tree of about 5-10 m tall with smooth bark gro\Vs mostly in the swampy areas (Mat Salleh, 1993). The distribution of GOl1io/halamlls sp cies is endemic throughout Malaysia. The di stribution of Gonio/ha/amus spp. ill Malaysia is sho\\n in Table I. Table 1: Distribution of (Jol1iolhalamlls spp. in Malaysia (Mat Salleh. 1993). Species Locations - U curtisii Kelantan, Perak, Selangor (j. IIl/1hmSlIS Peninsular (j. giJl,un/el1s Peninsular, Sarawak (j. Ina/ayanus Peninsular except Perl is & Malacca, Sarawak, Sabah Ci. rid/e.vi Peninsular, Sarawak, Sabah (i. Inacrophylllls Peninsu'lar except Perl is, Sarawak, Sabah (i. IIvamides Kedah, Perak, Pahang, Sarawak, Sabah G. tapis Penang, Perak, Johor, Sarawak U. undersonii Sarawak 0 . horneensis Sarawak 0. sindairianlls Sarawak (i. ve/1I1inus Sarawak, Sabah ( i. / asciculu/lls Sarawak 3 vemiolha/amus spp. are widely used in traditional medicine in Malaysia. For example. (ioniolhala177l1s gigal1leus is used for the treatment after giving birth (Wiart. 2001). The uses of some other 'pecies of Goniolha/all1us in traditional medicine are given in Table 2.
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