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Bioactivity and Chemical Investigations Of BIOACTIVITY AND CHEMICAL INVESTIGATIONS OF PERESKIA BLEO AND PERESKIA GRANDIFOLIA SIM KAE SHIN THESIS SUBMITTED IN FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY FACULTY OF SCIENCE UNIVERSITY OF MALAYA KUALA LUMPUR 2010 UNIVERSITI MALAYA ORIGINAL LITERARY WORK DECLARATTON Name of Candidate: (l.C/Passport No: Registration/llatric I'J o: Name of Degree: Title of Project Paper/Research ReporUDissefiationiThesis ("this Work"): ) ) Field of Study: I do solemnly and sincerely declare that: (1) I am the sole author/writer of this Work; (2) This Work is original; (3) Any use of any work in which copyright exists was done by way of fair dealing and for permitted purposes and any excerpt or extract from, or reference to or reproduction of any copyright work has been disclosed expressly and sufficiently and the title of the Work and its authorship have been acknowledged in this Work; (4) I do not have any actual knowledge nor do I ought reasonably to know that the making of this work constitutes an infringement of any copyright work; (5) I hereby assign all and every rights in the copyright to this Work to the University of Malaya ("UMjl), who henceforth shall be owner of the copyright in this Work and that any reproduction or use in any form or by any means whatsoever is prohibited without the written consent of UM having been first had and obtained; (6) I am fully aware that if in the course of making this Work I have infringed any copyright whether intentionally or otherwise, I may be subject to legal action or any other action as may be determined by UM. Candidate's Signature Date Subscribed and solemnly declared before, Witness's Signature Date Name: Designation: BIOACTIVITY AND CHEMICAL INVESTIGATIONS OF PERESKIA BLEO AND PERESKIA GRANDIFOLIA ABSTRACT Ethnopharmacological data has been one of the common useful criteria in drug discovery. Pereskia bleo and Pereskia grandifolia (Cactaceae), commonly known as ‘Jarum Tujuh Bilah’ in Malay and ‘Cak Sing Cam’ in Chinese have long been used as natural remedies in Malaysia. The experimental approach in the present study was based on bioassay-guided fractionation. The crude methanol and fractionated extracts of both Pereskia spp. were initially investigated for their biological activities such as antioxidant, antimicrobial and cytotoxic effect against five human cancer cell lines, namely nasopharyngeal epidermoid carcinoma cell line (KB), cervical carcinoma cell line (CasKi), colon carcinoma cell line (HCT 116), hormone-dependent breast carcinoma cell line (MCF7), lung carcinoma cell line (A549) and the non-cancer human fibroblast cell line (MRC-5) using in vitro cytotoxicity assay, in order to identify the bioactive extracts of both Pereskia spp. The hexane and ethyl acetate extracts of both Pereskia spp. generally showed stronger antioxidant activities than the other extracts. Ethyl acetate extracts of both Pereskia spp. also showed some mild antimicrobial activities against the tested bacteria. In the cytotoxicity assay, both Pereskia spp. exerted no damage to MRC-5 normal cells. The ethyl acetate extracts of both Pereskia spp. in general gave higher inhibition and stimulation values against various cancerous cell lines compared to other extracts. The cell deaths of the selected cancer cells elicited by the cytotoxic active extracts of both Pereskia spp. were found to be apoptotic in nature based on a clear indication of DNA fragmentation, which is a hallmark of apoptosis. In addition, the LUX RT-qPCR [real- ii time reverse transcriptase–polymerase chain reaction (RT-qPCR) using LUX (Light Upon eXtension) primers] analysis showed that apoptosis elicited by the cytotoxic extracts on selected cancer cells was mediated by p53, caspase-3 and c-myc activation in different expression levels. Methyl palmitate, methyl linoleate, methyl α-linolenate and phytol were identified from the hexane extract of Pereskia bleo by GCMS analysis whilst methyl palmitate, methyl linoleate, methyl α-linolenate and methyl stearate were identified from the hexane extract of Pereskia grandifolia. From the results of the biological screenings, it is observed that the ethyl acetate extracts generally have stronger biological activities than other extracts. Further chemical investigations were thus directed to the ethyl acetate extracts of both Pereskia spp. 2,4-Di-tert-butylphenol (1), α-tocopherol (2), phytol (3), ß-sitosterol (4), dihydroactinidiolide (5) and a mixture of sterols containing campesterol (6), stigmasterol (7) and β-sitosterol (4) were isolated from Pereskia bleo whilst 2,4-di-tert- butylphenol (1), α-tocopherol (2), ß-sitosterol (4) and mixture containing methyl palmitate (9), methyl oleate (10), methyl stearate (11) and 2,4-di-tert-butylphenol (1) were isolated from Pereskia grandifolia. It is interesting to note that 2,4-ditert- butylphenol (1), α-tocopherol (2) and ß-sitosterol (4) were isolated from the ethyl acetate extracts of both Pereskia spp. The cytotoxic activities of the isolated constituents were evaluated against the above human cell lines and further studies on their mode of action suggested that these activities are connected with induction of apoptosis. In addition, the toxicity of both Pereskia spp. was evaluated in vivo and were considered safe in acute oral toxicities in experimental mice. The screening of the iii locally grown Pereskia bleo and Pereskia grandifolia indicated the presence of alkaloids, but the concentration was very low. The findings of Pereskia bleo and Pereskia grandifolia in the present study provided scientific validation on the use of the leaves of both Pereskia spp. for the treatment of cancer. Further studies on the mutagenic and toxicity effect over a longer period of time involving detection of effects on vital organ functions should be carried out to ensure that the plants are safe for human consumption. iv KAJIAN BIOAKTIVITI DAN KIMIA PERESKIA BLEO DAN PERESKIA GRANDIFOLIA ABSTRAK Data etnofarmakologi merupakan salah satu kriteria umum yang berguna dalam penemuan sesuatu ubat tertentu. Pereskia bleo dan Pereskia grandifolia (Cactaceae) yang biasa dikenali sebagai ‘Jarum Tujuh Bilah’ di kalangan orang Melayu dan ‘Cak Sing Cam’ di kalangan orang Cina telah lama digunakan sebagai jamu semulajadi di Malaysia. Eksperimen dalam penyelidikan ini dijalankan berdasarkan pemfraksian berpanduan bioasei. Kajian awal bioaktiviti ekstrak mentah serta fraksi daripada kedua- dua spesies Pereskia, seperti kesan antioksidan, antimikrob dan kesitotosikan telah dikaji untuk mengenalpasti ekstrak bioaktif bagi kedua-dua spesies tersebut. Penyaringan aktiviti kesitotoksikan telah dijalankan menggunakan asei kesitotoksikan in vitro ke atas lima titisan sel karsinoma manusia, iaitu titisan sel karsinoma epidermoid nasofarinks (KB), titisan sel karsinoma serviks (CasKi), titisan sel karsinoma kolon (HCT 116), titisan sel karsinoma payu dara yang melibatkan hormon (MCF7), titisan sel karsinoma paru-paru (A549) serta titisan sel manusia bukan karsinoma (MRC-5). Ekstrak heksana dan etil asetat bagi kedua-dua spesies Pereskia secara umumnya menunjukkan aktiviti antioksidan yang lebih kuat daripada ekstrak lain. Ekstrak etil asetat bagi kedua-dua spesies Pereskia juga menunjukkan aktiviti antimikrob yang lemah pada bakteria yang dikaji. Bagi asei kesitotoksikan, ekstrak kedua-dua spesies Pereskia tidak aktif ke atas sel normal MRC-5. Ekstrak etil asetat kedua-dua spesies Pereskia secara umumnya menunjukkan nilai rintangan dan stimulasi yang lebih tinggi ke atas pelbagai titisan sel kanser berbanding dengan ekstrak v lain. Kematian kanser sel yang dirangsang oleh ekstrak aktif kedua-dua spesies Pereskia telah didapati mengaruh kematian sel secara apoptosis berdasarkan tanda fragmentasi DNA yang jelas. Fragmentasi DNA merupakan ciri utama apoptosis. Tambahan lagi, analisis LUX RT-qPCR [real-time reverse transcriptase–polymerase chain reaction (RT-qPCR) using LUX (Light Upon eXtension) primers] menunjukkan apoptosis yang dirangsang oleh ekstrak aktif ke atas sel kanser tertentu adalah menerusi pengaktifan p53, caspase-3 dan c-myc pada tahap ekspresi yang berbeza. Metil palmitat, metil linoleat, metil α-linolenat dan fitol telah dikenalpasti daripada ekstrak heksana Pereskia bleo melalui analisis GCMS manakala metil palmitat, metil linoleat, metil α-linolenat dan metil stearat telah dikenalpasti daripada ekstrak heksana Pereskia grandifolia. Daripada hasil penyaringan biologi, ekstrak etil asetat secara umumnya didapati mempunyai aktiviti biologi yang lebih kuat daripada ekstrak yang lain. Kajian kimia seterusnya ditumpukan kepada ekstrak etil asetat bagi kedua-dua spesies Pereskia. 2,4-Di-tert-butilfenol (1), α-tokoferol (2), fitol (3), ß-sitosterol (4), dihidroaktinidiolid (5) dan satu campuran sterol yang mengandungi kampesterol (6), stigmasterol (7) and β-sitosterol (4) telah dipisahkan dan dikenalpasti daripada Pereskia bleo sementara 2,4-di-tert-butilfenol (1), α-tokoferol (2), ß-sitosterol (4) dan satu campuran sebatian yang mengandungi metil palmitat (9), metil oleate (10), metil stearat (11) dan 2,4-di-tert-butilfenol (1) telah dipisahkan dan dikenalpasti daripada Pereskia grandifolia. Perlu diambil perhatian bahawa 2,4-di-tert-butilfenol (1), α-tokoferol (2) dan ß-sitosterol (4) wujud dalam ekstrak etil asetat kedua-dua spesies Pereskia. Kajian aktiviti kesitotosikan sebatian ke atas titisan sel kanser dan penyelidikan selanjutnya ke atas mod tindakan, mencadangkan aktiviti sitotosik sebatian adalah berkaitan dengan induksi apoptosis. vi Di samping
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