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1.0 LAPORAN PROJEK SARJANA MUDA

Laporan projek Sarjana Muda adalah laporan penyelidikan yang ditulis oleh pelajar untuk

memenuhi sebahagian syarat penganugerahan Ijazah Sarjana Muda. Setiap laporan projek mesti

ditulis mengikut format yang telah ditetapkan sebagaimana yang diterangkan dalam makalah ini.

1.1 Panjang Laporan Projek Sarjana Muda

Panjang minimum laporan adalah 40 muka surat dan maksimanya tidak melebihi 100 muka

surat. Had maksimum ini tidak termasuk lampiran, jadual, gambar rajah dan lain-lain ilustrasi. Penulis

yang laporan projeknya melebihi had ini, hendaklah memohon kebenaran daripada Penyelia serta

Penyelaras Projek Sarjana Muda Jabatan masing-masing. Pembahagian jumlah muka surat untuk

setiap bab dalam laporan projek adalah sebagaimana dalam Jadual 1.1 berikut.

Jadual 1.1: Pembahagian Jumlah Muka Surat Untuk Setiap Bab

Perkara Minimum Maksimum

Bab 1 (Pengenalan) 5 20

Bab 2 (Kajian Literatur) 15 30

Bab 3 (Kaedah)

Bab 4 (Hasil dan Perbincangan)

5

10

20

20

Bab 5 (Kesimpulan dan Cadangan) 2 5

Rujukan 3 5

1.2 Penaipan Teks

Laporan projek mestilah ditaip selang satu setengah baris di atas kertas putih saiz A4

(210mm x 297mm) yang bermutu tinggi dan berat minimum 80 g. Bagaimanapun, bab, sub-bab,

tajuk, jadual, rujukan dan lampiran ditaip pada selang satu baris.

Had sempadan teks untuk setiap muka surat hendaklah ditetapkan dan selaras. Had

sempadan kiri ialah 4.0 cm (untuk tujuan penjilidan) sementara had sempadan atas, kanan dan bawah

ditetapkan pada 2.5 cm. Ini boleh diselaraskan melalui “Page Setup” (Microsoft Word). Huruf-huruf

condong dan bersambung (contohnya tulisan italic atau Gothic) dan yang kecil (contohnya tulisan

Mikron) tidak boleh digunakan untuk keseluruhan teks kecuali pada perkataan tertentu, rajah dan

jadual. Saiz (tinggi) huruf yang digunakan dalam teks hendaklah tidak kurang daripada 2.0 mm bagi

huruf besar dan 1.5 mm bagi huruf kecil.

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Taipan teks dengan pencetak titik matriks (dot matrix) tidak boleh digunakan kecuali dengan

pencetak titik matriks berkualiti tinggi (letter quality). Simbol yang tidak dapat ditaipkan hendaklah

ditulis dengan pen yang menggunakan dakwat hitam (Indian inks). Saiz font bagi teks ialah 12.

2.0 FORMAT PENULISAN LAPORAN PROJEK

Format penulisan dan kandungan laporan projek disusun mengikut urutan sebagaimana

dalam Jadual 2.1 berikut.

Jadual 2.1: Format Penulisan dan Kandungan Laporan Projek

Perkara Status Contoh

Lampiran Catatan

Muka Depan Kulit

wajib

1

-

Tetulang Buku Laporan Projek wajib 2

Muka Kosong wajib - -

Borang Pengesahan Status Tesis

wajib 3 tidak bernombor

Halaman Tajuk wajib 4 tidak bernombor tetapi dikira sebagai (i)

Halaman Pengesahan Penyelia wajib 5 bernombor Roman kecil

Halaman Pengakuan wajib 6 bernombor Roman kecil

Halaman Dedikasi pilihan 7 bernombor Roman kecil

Halaman Penghargaan pilihan 8 bernombor Roman kecil

Abstrak wajib 9 bernombor Roman kecil

Abstract (dlm. Bahasa Inggeris) wajib 10 bernombor Roman kecil

Kandungan wajib 11 dan 12 bernombor Roman kecil

Daftar Singkatan/Simbol/Istilah wajib 13 bernombor Roman kecil

Senarai Jadual wajib 14 bernombor Roman kecil

Senarai Rajah wajib 15 bernombor Roman kecil

Senarai Lampiran wajib (jika ada lampiran)

- bernombor Roman kecil

Teks wajib 16,17, 18, 19, 20 dan 21

bernombor Arab bersambungan dengan teks

Rujukan wajib 22 bernombor Arab bersambungan dengan teks

Lampiran pilihan 23, 24, 25 bernombor Arab bersambung dengan teks

Muka Kosong wajib -

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2.1 Kulit Depan dan Tetulang Buku Laporan Projek Sarjana Muda

Setiap salinan laporan projek hendaklah bermutu tinggi dan dibukukan dengan kulit jenis

“buckram” berwarna hijau terusi (warna untuk Fakulti Sains bagi Laporan Projek Sarjana Muda).

Pada muka depan kulit mestilah dicetak dengan bertulisan emas huruf besar cerai (bold) sebagaimana

susunan berikut:

Tajuk Laporan Projek Sarjana Muda

Nama penulis/pengarang

Nama penuh universiti dan tahun Ijazah dianugerahkan

(sila lihat contoh di Lampiran 1)

Pada tetulang buku Laporan Projek pula mesti ditulis perkara berikut:

Nama penuh Ijazah

Nama penulis/pengarang

Tahun Ijazah dianugerahkan dan UTM

(sila lihat contoh di Lampiran 2)

2.2 Muka Kosong

Setiap buku Laporan Projek hendaklah mengandungi satu helaian kosong di helaian pertama

dan terakhir.

2.3 Borang Pengesahan Status Tesis

Borang pengesahan status tesis hendaklah diisi dengan lengkap. Borang ini boleh diperolehi

dari Perpustakaan Sultanah Zanariah. Sila lihat contoh di Lampiran 3. Hanya laporan projek yang

mendapat gred A dan A+ akan diserahkan kepada perpustakaan sebagai bahan rujukan.

2.4 Halaman Judul

Halaman judul hendaklah mengandungi perkara-perkara berikut dan dalam tertib yang

disenaraikan.

Tajuk lengkap Laporan Projek Sarjana Muda

Nama penulis/pengarang

Ijazah yang mana Laporan Projek disyaratkan

Nama Fakulti dan nama penuh Universiti

Tahun ijazah dianugerahkan

(Sila lihat contoh di Lampiran 4)

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2.5 Halaman Pengesahan Penyelia

Contoh pengesahan adalah di Lampiran 5. Nama penyelia hendaklah ditaip di bawah

garisan tandatangan.

2.6 Halaman Pengakuan

Halaman ini mengandungi pengakuan tentang keaslian projek penyelidikan. Ia hendaklah

ditandatangani oleh penulis. Contoh pengakuan adalah pada Lampiran 6.

2.7 Halaman Dedikasi

Pelajar dibenarkan untuk menyatakan dedikasi kepada seseorang atau beberapa orang

dengan kata-kata yang tidak keterlaluan pada satu muka surat sahaja. Contoh dedikasi adalah pada

Lampiran 7.

2.8 Halaman Penghargaan

Penghargaan ialah ruangan bagi pelajar-pelajar memberikan penghargaan kepada pihak

tertentu. Penghargaan (jika ada) hendaklah ditulis dengan ringkas dalam satu muka surat sahaja.

Contoh penghargaan diberikan dalam Lampiran 8.

2.9 Abstrak

Abstrak hendalah ditulis dalam bahasa Melayu dan diikuti oleh terjemahannya dalam bahasa

Inggeris (Abstract) di muka surat yang berikutnya (sebaliknya bagi laporan projek yang ditulis dalam

bahasa Inggeris). Abstrak hendaklah ditulis tidak melebihi satu muka surat dan ditaip dengan langkau

satu setengah baris. Abstrak ini menjelaskan secara ringkas tentang bidang kajian, kaedah

penyelidikan, perbahasan utama tentang kajian dan singkatan keputusan yang telah dicapai. Contoh

abstrak adalah sebagaimana dalam Lampiran 9 dan 10.

2.10 Kandungan

Senarai kandungan hendaklah diletak selepas abstrak bahasa Inggeris pada halaman yang

baru. Senarai kandungan ini menyenaraikan secara berturutan dengan nombor muka surat kesemua

bahagian atau sub bahagian laporan projek, kecuali bahagian sebelum abstrak. Contoh senarai

kandungan diberikan dalam Lampiran 11 dan 12.

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2.11 Daftar Singkatan/Simbol/Istilah

Senarai ini menyenaraikan simbol atau singkatan atau tatanama atau istilah yang terdapat

dalam laporan projek. Contoh halaman ini ditunjukkan dalam Lampiran 13.

2.12 Senarai Jadual

Senarai jadual ini mengandungi semua tajuk jadual yang dimuatkan dalam laporan projek

berserta dengan nombor muka surat di mana ia boleh didapati. Contoh halaman ini boleh didapati di

Lampiran 14.

2.13 Senarai Rajah

Senarai rajah merupakan halaman yang mengandungi senarai fotograf, lukisan, graf, carta

dan peta. Nombor muka surat semua bahan illustrasi hendaklah dicatatkan. Contoh disertakan di

Lampiran 15.

2.14 Senarai Lampiran

Pada halaman ini, disenaraikan semua lampiran yang dimuatkan dalam teks. Sesuatu

penulisan tidak semestinya mengandungi senarai lampiran. Data kajian, jadual, contoh soal selidik,

peta gambar dan sebagainya yang terlalu panjang untuk dimuatkan ke dalam teks atau yang tidak

diperlukan secara langsung dalam perbincangan dalam teks, boleh disertakan sebagai lampiran.

3.0 TEKS UTAMA

Teks utama terdiri daripada:-

Pendahuluan (Bab 1)

Kajian Literatur (Bab 2)

Kaedah (Bab 3)

Hasil dan Perbincangan (Bab 4)

Kesimpulan dan Cadangan (Bab 5)

Rujukan

Lampiran

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4.0 BAB DAN KANDUNGAN

Laporan projek hendaklah ditulis dalam format bab, bahagian dan kalau perlu sub bahagian

yang sesuai. Setiap bab dinomborkan dengan huruf besar nombor Roman contohnya Bab I, Bab II,

Bab III dan seterusnya, atau dengan nombor contohnya Bab 1, Bab 2, Bab 3 dan seterusnya. Setiap

bab hendaklah diberikan tajuk. Jika cara ini yang dipilih, setiap bab mestilah mempunyai tajuk (supaya

seragam).

Tajuk bab hendaklah dituliskan empat (4) baris daripada nombor bab dan disusun

perkataannya supaya terletak di tengah-tengah barisan. Jika tajuk bab itu panjang dan melebihi satu

baris, aturkan perkataan-perkataannya dalam bentuk meruncing ke bawah.

Pecahan bab atau tajuk-tajuk kecil di sesuatu bab hendaklah diberikan nombor contohnya

1.1, 2.5, 3.1, 3.2.2 dan sebagainya. Struktur dan penomboran bahagian dalam teks boleh disusun

mengikut urutan tahap sub-tajuk dan tidak melebihi empat lapisan sebagaimana berikut.

BAB 1 Tahap pertama (Tajuk Bab)

1.1 Tahap kedua (sub-tajuk)

1.1.1 Tahap ketiga (sub-sub-tajuk)

Perenggan pertama, mestilah dimulakan 1.27 cm daripada jidar kiri dan empat (4) baris

daripada tajuk bab. Jangan mulakan perenggan baru pada baris akhir muka surat. Sebagai contoh

lihat Lampiran 16 dan 17.

4.1 Penomboran Muka Surat

Nomborkan muka surat mengikut urutan. Nombor muka surat hendaklah ditulis di sudut atas

sebelah kanan, 1.25 cm dari tepi atas dan 2.5 cm dari tepi sebelah kanan digit terakhir nombor

berkenaan.

Penomboran muka surat hendaklah memenuhi syarat berikut:-

(i) Bahagian permulaan laporan projek, bermula dari halaman judul, hendaklah dinomborkan

dengan angka kecil Roman (i, ii, iii dsb.); bahagian teks dan selepasnya hendaklah

menggunakan angka arab (1, 2, 3 dan seterusnya).

(ii) Halaman pertama laporan projek ialah halaman tajuk, dianggap sebagai muka surat “i” tetapi

tidak ditaip.

(iii) Halaman pertama bahagian teks dianggap sebagai halaman “1” tetapi nombornya tidak

ditaip. Begitu juga bagi halaman pertama setiap permulaan Bahagian atau Bab seterusnya,

7

tidak ditulis nombor muka suratnya tetapi diambil kira bagi menomborkan muka surat

berikutnya.

4.2 Rajah, Ilustrasi, Graf dan Jadual

Setiap rajah, ilustrasi, graf dan jadual mestilah dinomborkan. Penomboran hendaklah

mengikut bab. Nombor rajah, ilustrasi atau graf serta tajuknya hendaklah ditaip pada bahagian bawah

rajah, ilustrasi atau graf dengan langkau satu baris. Nombor jadual dan tajuknya hendaklah ditaip pada

bahagian atas jadual dengan langkau satu baris. Jarak antara tajuk jadual dan tajuk rajah, ilustrasi

atau graf dengan jadual, rajah, ilustrasi atau graf hendaklah dengan langkau satu setengah baris.

Semua rajah dan jadual hendaklah disenaraikan di dalam halaman Senarai Rajah dan Senarai Jadual.

Rajah, gambar, graf atau jadual sebaik-baiknya diletakkan selepas sahaja ia dirujuk buat pertama

kalinya dalam teks (Lampiran 18, 19, 20 dan 21 ).

4.3 Rujukan

Nombor rujukan dengan saiz tulisan 12 (Font size 12) atau bibliografi di dalam teks mestilah

ditulis dalam bentuk [ ] dan susunan nombornya hendaklah berurutan. Nombor rujukan jika ditulis

selepas akhir ayat hendaklah dituliskan sebelum koma atau titik.

Semua rujukan yang disebut dan dipetik hendaklah disenaraikan selepas bab terakhir

(Lampiran 22). Senarai rujukan hendaklah ditulis mengikut format berikut.

Jurnal

Penulis (Tahun). Tajuk artikel. Tajuk Journal Jilid (Bil. Jika ada), Muka surat.

Contoh:

Fletcher, T.R. and Rosenfled, R.N. (1985). Determination of Boric Acid in Food. J. Am. Chem. Soc.

107, 2203-2212.

Hakim, E.H., Achmad, S.A., Juliawaty, L.D., Makmur, L., Syah, Y.M., Aimi, N., Kitajima, M., Takayama,

H., Ghisalberti, E.L. (2006). Prenylated flavonoids and related compounds of the Indonesian

Artocarpus (Moraceae). J. Nat. Med. 60,161-184.

Ngadjui, B.T., Abegaz, B.M., Dongo, E., Tamboue, H., Fogue, K. (1998). Geranylated and Prenylated

Flavonoids From The Twigs of Dorstenia mannii. Phytochemistry 48, 349-354.

Jamil, S., Sirat, H.M., Jantan, I., Aimi, N., Kitajima, M. (2005). Flavonoids from Artocarpus teysmanii

Miq. Malays. J. Sci. 24, 99-103.

8

Buku

Penulis (Tahun). Tajuk. Edisi (jika bukan edisi pertama). Tempat dicetak. Pencetak. Muka surat.

Contoh:

Theusen, G.J. and Fabrycky, W.J. (1984). Engineering Economy. 6th. Ed. Englewood Cliffs, New

Jersey: Prentice-Hall. 150-178.

Burkill, I.H. (1966). Dictionary of The Economic Products of The Malay Peninsula, Ministry of

Agriculture and Co-operatives, Kuala Lumpur, Malaysia. 1, 249-260.

Wade Jr., L.G. (2006). Organic Chemistry. 6th. Ed. New Jersey, USA: Prentice Hall. 189-278.

Artikel di dalam Buku

Penulis (Tahun). Tajuk artikel. Di dalam: Nama Pengarang Buku. Tajuk Buku, Tempat dicetak.

Pencetak. Muka surat.

Contoh:

Sukiman Sarmani (1987). Pencemaran Radioaktif. dlm. Ahmad Badri Mohamad, Perspektif

Persekitaran, Petaling Jaya: Fajar Bakti. 71-87.

Artikel Persidangan

Penulis (Tahun). Tajuk artikel. Nama Persidangan. Tarikh persidangan. Tempat dicetak. Pencetak.

Muka surat.

Contoh:

Sheta, A.F. and Jong, K.D. (1996). Parameter Estimation of Nonlinear Systems in Noisy Environments

Using Genetic Algorithms. Proceedings of the 1996 IEEE International Symposium on Intelligent

Control. September 15-18. Dearborn, Michigan: IEEE, 360 - 365.

Patent

Nama pencipta (Tahun). Tajuk Ciptaan (Nombor Patent).

Contoh:

Lindgren, A.E. (1988). Screen Room Air Inlet and Wave Guard. (U.S. Patent 6, 379, 457).

Prosiding

Nama penulis (Tahun). Tajuk artikel, Nama pengedit. Nama persidangan, Tempat Persidangan. Muka

surat.

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Contoh:

Prevost, M. and Bugarel, R. (1980). Several Physical Properties of Resin Concrete, in (Jones, E. et. al.

(ed.)). Proceedings of the International Seminar on Polymer Concrete. Stockholm. 85.

Tesis

Penulis (Tahun). Tajuk Tesis. Institusi: Penganugerahan Tesis.

Contoh:

Hanim Awab (1990). Analisis Bovina dan Porkina dalam Makanan Malaysia. Universiti Teknologi

Malaysia : Tesis Sarjana.

Nur Zulaikha Yusof (2008). Isolation and Applications of Red Pigments from Serratia marcescens.

Universiti Teknologi Malaysia: Bachelor of Science (Industrial Chemistry) Project Report.

Bahan rujukan yang diterima untuk penerbitan tetapi belum diterbitkan lagi.

Contoh:

Jones, A.R. (1996). Stereoselective Synthesis of Maytansine Synthon. J. Chem. Soc. Perkin Trans I. In

press.

Bahan rujukan yang telah dihantar untuk penerbitan tetapi belum diterima lagi.

Contoh:

Jones, A.R. (1995). Performance of Epoxy and Polyester Polymer Concrete. Angew. Chem. Submitted

for publication.

Bahan rujukan yang tidak diterbitkan

Contoh:

Hasnah Mohd Sirat. Pengasingan Sebatian Diterpena daripada Achasma. Tidak diterbitkan.

Perundangan

Nama Negara (Tahun). Tajuk perundangan. Nombor Perundangan.

Contoh:

Malaysia (1983). Perintah Monumen Lama dan Tapak Tanah Bersejarah. P.U.(A)41 1983.

Standard

Nama Standard (tahun). Tajuk Standard. Tempat dicetak, Nombor Standard.

10

Contoh:

British Standards Institution (1987). Tongued and Grooved Software Flooring. London, BS 1297.

Katalog Komersial

Nama Pengedar (Tahun). Tajuk. Tempat dicetak: Nota.

Contoh:

Howick Partitioning Ltd. (1984). Howick: Partitioning in Business. Redhill (U.K.): Trade Brochure.

Rujukan dari Internet

Walaupun internet menyediakan maklumat yang banyak, namun informasi dari internet tidak kekal dan

selalu dikemaskini mengikut masa tertentu. Oleh yang demikian, kenyataan serta fakta ini TIDAK

BOLEH menjadi sandaran rujukan. Internet hanya boleh digunakan untuk menjejaki sumber asal

(primer) rujukan.

4.4 Lampiran

Sesuatu penulisan tidak semestinya mengandungi lampiran. Sekiranya ada, lampiran perlu

dinomborkan dan diberi tajuk. Lampiran hendaklah ditulis selepas kandungan utama ataupun teks

utama. Lampiran boleh mengandungi bahan-bahan penyokong contohnya graf, spektrum, atau

kromatogram; senarai dokumen dan sebagainya. Bagi laporan projek yang mengandungi program

komputer, program berkaitan hendaklah disalin dan diletakkan dalam lampiran. Contoh lampiran

ditunjukkan dalam Lampiran 23.

5.0 PENYERAHAN LAPORAN PROJEK UNTUK PENILAIAN

Satu salinan laporan projek dalam bentuk „spiral bound‟ hendaklah disiapkan dan dihantar

MENGIKUT TARIKH yang ditetapkan oleh Jawatankuasa Projek Sarjana Muda. Salinan laporan

projek tersebut hendaklah ditandatangani oleh Penyelia terlebih dahulu SEBELUM diserahkan

kepada Ahli Jawatankuasa Projek Sarjana Muda Jabatan Kimia. Pemeriksa dalaman Jabatan akan

membuat penilaian dan markah penilaian akan diberi berdasarkan kepada laporan projek yang

diserahkan ini. Segala cadangan pembetulan oleh pemeriksa atau penilai hendaklah dipatuhi oleh

pelajar setelah berbincang dengan penyelia sebelum naskah laporan projek dijilid.

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5.1 Prosiding Projek Sarjana Muda

Setiap pelajar dikehendaki menyediakan prosiding sepanjang LIMA HINGGA SEPULUH (5-

10) muka surat dengan langkau satu baris dan menyerahkan sebanyak DUA (2) salinan dalam

bentuk „hard copy‟ kepada Ahli Jawatankuasa Projek Sarjana Muda Jabatan Kimia. Prosiding ini akan

diserahkan kepada dua orang penilai untuk dinilai dan dijadikan rujukan ketika pelajar membentang

projek di Simposium Projek Sarjana Muda Jabatan Kimia pada tarikh yang ditetapkan. Format

prosiding dan contoh ditunjukkan dalam Lampiran 24 dan 25.

6.0 PEMBUKUAN LAPORAN PROJEK

6.1 Bilangan Salinan

Pelajar perlu menyediakan TIGA (3) salinan laporan projek berjilid keras. Satu salinan

laporan projek berjilid keras tersebut hendaklah diserahkan MENGIKUT TARIKH DITETAPKAN

kepada Ahli Jawatankuasa Projek Sarjana Muda Jabatan Kimia sebagai syarat pelajar LULUS

Projek Sarjana Muda (SSU 3924). Satu salinan diserahkan kepada Penyelia dan satu salinan lagi

untuk simpanan pelajar. Kegagalan menyerahkan naskah laporan projek berjilid keras kepada Ahli

Jawatankuasa Projek Sarjana Muda Jabatan Kimia akan mengakibatkan pelajar mendapat keputusan

GAGAL.

6.2 Perbelanjaan

Perbelanjaan menaip, mencetak, menjilid dan lain-lain ditanggung sepenuhnya oleh pelajar.

12

SENARAI LAMPIRAN

LAMPIRAN TAJUK MUKA SURAT

1 Contoh Kulit Depan 13

2 Contoh Tetulang Naskah Laporan Projek 14

3 Borang Pengesahan Status Tesis 15

4 Contoh Halaman Judul 16

5 Halaman Pengesahan Penyelia 17

6 Halaman Pengakuan Pelajar 18

7 Contoh Halaman Dedikasi 19

8 Contoh Halaman Penghargaan 20

9 Contoh Abstrak 21

10 Contoh Abstract 22

11-12 Contoh Kandungan 23-24

13 Contoh Daftar Singkatan/Simbol/Istilah 25

14 Contoh Senarai Jadual 26

15 Contoh Senarai Rajah 27

16 Contoh Bab 28

17 Contoh Bahagian 29

18 Contoh Memasukkan Graf Dalam Teks 30

19 Contoh Memasukkan Gambar Dalam Teks 31

20 Contoh Jadual Dalam Teks 32

21 Contoh kedua Jadual Dalam Teks 33

22 Contoh Senarai Rujukan (mengikut sistem nombor) 34

23 Contoh Lampiran 1 35

24 Format Prosiding PSM 36

25 Contoh Prosiding PSM 2008 38

13

ISOLATION AND APPLICATIONS OF RED PIGMENTS FROM

Serratia marcescens

(TIMES NEW ROMAN, FONT SIZE 12, BOLD, CENTER)

NUR ZULAIKHA BINTI YUSOF (BOLD)

UNIVERSITI TEKNOLOGI MALAYSIA

2.5 cm

2.5 cm 4.0 cm

2.5 cm

2.5 cm

2.5 cm

Lampiran 1: Contoh Kulit Depan

14

Lebar ≤ 25 mm Lebar ≤ 25 mm

Lebar ≤ 25 mm Lebar ≤ 25 mm

N

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20 mm 20 mm

20 mm 20 mm

Font

Size 14

Lampiran 2: Contoh Tetulang Naskah Laporan

Projek

15

UNIVERSITI TEKNOLOGI MALAYSIA

NOTES : * If the thesis is CONFIDENTIAL or RESTRICTED, please attach with the letter

from the organisation with period and reasons for confidentiality or restriction.

DECLARATION OF THESIS / UNDERGRADUATE PROJECT PAPER AND COPYRIGHT

Author’s full name : NUR ZULAIKHA BINTI YUSOF

Date of birth : 22 MARCH 1986

Title : ISOLATION AND APPLICATIONS OF RED PIGMENTS FROM Serratia

marcescens

Academic Session: 2007/2008

I declare that this thesis is classified as :

CONFIDENTIAL (Contains confidential information under the Official

Secret Act 1972)*

RESTRICTED (Contains restricted information as specified by the

organisation where research was done)*

OPEN ACCESS I agree that my thesis to be published as online open

access (full text)

I acknowledged that Universiti Teknologi Malaysia reserves the right as follows :

1. The thesis is the property of Universiti Teknologi Malaysia.

2. The Library of Universiti Teknologi Malaysia has the right to make copies for the

purpose of research only.

3. The Library has the right to make copies of the thesis for academic exchange.

Certified by :

…………………………. ………………………………………….

SIGNATURE SIGNATURE OF SUPERVISOR

860322-46-5434 PROF. DR. WAN AZLINA AHMAD (NEW IC NO. /PASSPORT NO.) NAME OF SUPERVISOR

Date : APRIL 2008 Date : APRIL 2008

Lampiran 3: Borang Pengesahan Status Tesis

16

ISOLATION AND APPLICATIONS OF RED PIGMENTS FROM

Serratia marcescens

X

NUR ZULAIKHA BINTI YUSOF

X

A report submitted in partial fulfilment of the

requirements for the award of the degree of

Bachelor of Science (Industrial Chemistry)

Y

Faculty of Science

Universiti Teknologi Malaysia

Y

2008

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Lampiran 4: Contoh Halaman Judul

17

“I hereby declare that I have read this report and in my opinion this report is

sufficient in terms of scope and quality for the award of the degree of Bachelor of

Science (Industrial Chemistry)*”

Signature : ………………………………….

Name of Supervisor : ………………………………….

Date :………………………………….

* or Bachelor of Science (Chemistry)

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Lampiran 5: Contoh Pengesahan Penyelia

18

“I declare that this report entitled “Isolation and Applications of Red Pigments

from Serratia marcescens “is the result of my own research except as cited in the

references. The report has not been accepted for any degree and is not currently

submitted in candidature of any other degree.”

Signature : .............................................

Name : NUR ZULAIKHA BINTI YUSOF

Date : 30 APRIL 2008

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Lampiran 6: Halaman Pengakuan Pelajar

19

Sample of a dedication page

To my beloved mother and father

(tidak melebihi lima (5) baris,

Times New Roman, font 12, bold, spacing 1.5, Italic, center)

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Lampiran 7: Contoh Halaman Dedikasi

20

ACKNOWLEDGEMENT

4 line spacing

Special thanks go to my supervisor, Prof. Dr. Wan Azlina Ahmad, for her

help during the course of this research. Without her time and patience much of this

work could not have been accomplished. I have gained a lot of knowledge and

experience during doing this research.

I also would like to express my gratitude to PM. Dr. Farediah Ahmad and

PM. Mohd. Nazlan bin Mohd. Muhid for their guidance in FTIR analysis, as well as

PM Dr Wan Yunus and Nor Amalina Zulkifli from UiTM, Shah Alam for their

guiding and assistance in completion some part of this research.

A million thanks also go to Dr. Zainul Akmal Zakaria, all Biotech. Master

students, Biotech. research assistance and to my entire fellow friends for their

knowledge, encouragement and guidance throughout the research.

Last but not least, I wish to express my sincere appreciation to my beloved

family for their continuous support, advices and motivation for me to complete my

research .Thank you so much.

(Maksimum 1 muka surat sahaja)

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Lampiran 8: Contoh Halaman Penghargaan

21

ABSTRAK

4 line spacing

Terdapat trend peningkatan terhadap penggantian pewarna sintetik oleh

pigmen semulajadi kerana permintaan yang tinggi oleh pengguna untuk produk

semulajadi. Pengguna telah menyedari bahawa produk semulajadi adalah lebih

selamat dan mesra alam. Dalam kajian ini, pemencilan dan pengaplikasian pigmen

dari Serratia marcescens, telah dijalankan. Penghasilan pigmen merah oleh Serratia

marcescens telah dinilai di dalam pelbagai medium iaitu cecair sisa nenas, kaldu

nutrien, gula merah dan campuran cecair sisa nenas dan gula merah untuk mencari

medium terbaik untuk penghasilan pigmen. Selepas itu, pigmen bakteria telah

diekstrak menggunakan cara pendidihan dan pengekstrakan pelarut untuk

penggunaan seterusnya dalam pewarnaan fabrik (akrilik, kapas, poliester, poliester

mikroserat dan sutera), pembuatan kertas dan pembuatan lilin. Semua fabrik telah

diuji daya tahan warnanya terhadap basuhan, perpeluhan, cahaya dan

geseran/gosokan menggunakan kaedah piawai (MS ISO). Daripada keputusan kajian,

warna pigmen yang paling terang telah diperolehi apabila Serratia marcescens

dibiakkan di dalam 10% gula merah. Teknik pendidihan telah dipilih sebagai cara

pengekstrakan terbaik disebabkan oleh pengendaliannya yang mudah terutamanya

untuk aplikasi skala besar. Akrilik yang diwarnakan telah menunjukkan tahan warna

yang tinggi terhadap semua rawatan luaran berbanding kapas, poliester, poliester

mikroserat dan sutera. Semua fabrik kecuali kapas menunjukkan tahan warna yang

rendah terhadap cahaya tetapi dalam lingkungan yang agak baik untuk ujian tahan

warna yang lain. Pigmen dari Serratia marcescens telah berjaya diaplikasikan di

dalam pewarnaan fabrik dan pembuatan lilin.

(Maksimum 1 muka surat dalam 1 perenggan sahaja)

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Lampiran 9: Contoh Abstrak

22

ABSTRACT

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There has been an increasing trend towards replacement of synthetic

colorants by natural pigments because of the strong consumer demand for more

natural products. Consumers have realized that natural products are much safer and

environmental friendly. In this study, the isolation and applications of pigments from

Serratia marcescens, was carried out. The red pigments production by Serratia

marcescens were evaluated in various media namely liquid pineapple waste (LPW),

nutrient broth, brown sugar (BS) and mixtures of LPW-BS to find the best media for

pigments production. The bacterial pigments was then extracted using boiling and

solvent extraction method for further use in fabric (acrylic, cotton, polyester,

polyester microfibre and silk) dyeing, candle making and paper making. The fabrics

were tested for its colourfastness towards washing, perspiration, light and

rubbing/crocking using standard method (MS ISO). From results of the study, the

most intense pigment was obtained when Serratia marcescens was grown in 10%

BS. The boiling technique was chosen as the best extraction method due to its simple

handling especially for the large-scale applications. The dyed acrylic fabric displayed

the highest colourfastness to all the external treatments compared to cotton,

polyester, polyester microfiber and silk. All other fabrics except cotton displayed low

colourfastness against light but tolerable range for other colourfastness tests. The

pigments from Serratia marcescens was successfully applied for fabric dyeing and

candle making.

(maximum 1 paragraph in 1 page)

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Lampiran 10: Contoh Abstract

23

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TABLE OF CONTENTS

4 line spacing

CHAPTER TITLE PAGE

SUPERVISOR’S DECLARATION

AUTHOR’ DECLARATION

DEDICATION

ACKNOWLEDGEMENT

ABSTRACT

ABSTRAK

TABLE OF CONTENTS

LIST OF TABLES

LIST OF FIGURES

LIST OF ABBREVIATIONS

LIST OF APPENDICES

ii

iii

iv

v

vi

vii

viii

xi

xii

xiii

xiv

1

INTRODUCTION

1

1.1 Background of Study

1.2 Statement of Problem

1.3 Objective and Scope of Study

1.4 Significance of Study

1

2

2

2

2 LITERATURE REVIEW 4

2.1 Definition of Pigment

2.2 General Properties of Pigments

2.2.1 Principle Properties of Pigments

2.3 Classification of Pigments

4

5

5

6

2.4 Bacteria and Pigments 7

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Lampiran 11: Contoh Kandungan

24

3 EXPERIMENTAL

3.1 Materials 14

3.1.1 Bacteria 14

3.1.2 Growth Medium 15

3.1.2.1 Nutrient Broth 15

3.1.2.2 Nutrient Agar 16

4 RESULTS AND DISCUSSION 25

4.1 Growth Profile of Serratia marcescens 25

4.2 Factors Affecting the Production of

Pigments by Serratia marcescens 26

4.2.1 Effect of Temperature 26

4.2.2 Effect of Different Media 27

4.3 Characterizations of Pigments from Serratia

marcescens 27

4.3.1 FT-IR Spectroscopic Analysis 27

5 CONCLUSIONS AND SUGGESTIONS 42

REFERENCES 44

APPENDICES 50

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Lampiran 12: Contoh Kandungan

25

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LIST OF ABBREVIATIONS

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A - Acrylic

AATCC - American Association of Textile Chemists and Colorists

BS - Brown sugar

C - Cotton

DDW - Distilled deionized water

FT-IR - Fourier Transform Infrared

g - Gram

kPa - kiloPascal

L - Liter

LPW - Liquid pineapple waste

M - Molar

mg - Miligram

mL - Mililiter

N - Normality

NB - Nutrient broth

nm - Nanometer

OD - Optical density

PPD - Phenylenediamine

Pm - Polyester microfiber

rpm - Rotation per minute

RNA - Ribonucleic acid

rRNA - Ribosomal ribonucleic acid

S. marcescens - Serratia marcescens

(Nota: Daftar singkatan yang digunakan mestilah yang telah diiktiraf

penggunaannya di dalam penulisan makalah kimia dalam bahasa Inggeris. Tidak

perlu buat singkatan untuk bahan kimia dan unit yang lazim)

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Lampiran 13: Contoh Daftar Singkatan/Simbol/Istilah

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LIST OF TABLES

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TABLE NO. TITLE PAGE

4.1

4.2

4.3

4.4

4.5

4.6

4.7

3 line spacing

Dyeing performance of the pigment on the fabrics

The standard method and equipment used for the

testing of fabrics

The rating for change in colour (a) and staining of

fabrics (b)

The rating of fabrics for colourfastness to light

The rating for change in colour (a) and staining (b)

of the fabrics

The rating for staining of fabrics towards rubbing/

crocking

The stability of pigments on paper to fluorescent

lamp and sunlight

35

36

38

39

40

40

43

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Lampiran 14: Contoh Senarai Jadual

27

2.5 cm

LIST OF FIG URES

4 line spacing

FIGURE NO. TITLE PAGE

2.1

2.2

2.3

2.4

4.1

4.2

4.3

4.4

4.5

4.6

4.7

4.8

4.9

4.10

3 line spacing

The structure of prodigiosin

The structure of violecein

The structure of β-carotene

The structure of phycocyanin

Growth profile of S. marcescens

Culture of red bacteria in nutrient broth grown

at: (a) 25oC, (b) 30

oC and 37

oC

Colour intensity of pigments in different

media; (a) nutrient broth, (b) brown sugar 10%,

(c) brown sugar 1%, (d) liquid pineapple waste,

(e) control liquid pineapple waste, (f) control

brown sugar 10%, (g) control brown sugar 1%,

(h) control nutrient broth

Effect of time on pigments production

FT-IR spectrum of the pellets at different

times of bacterial growth

The stability of pigments at varying pH

UV/Vis absorption spectra of red pigments as

function of pH

Boling extraction method

Pigments extracted using petroleum ether

The UV/Vis spectrum for pigment extracted

using petroleum ether

9

9

10

10

25

27

27

28

29

30

31

32

32

33

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Lampiran 15: Contoh Senarai Rajah

28

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CHAPTER I

4x single spacing

INTRODUCTION

4x single spacing

1.1 Background of Study

2x single spacing

Synthetic colourants have been widely used in the industries for many years.

However, most of the synthetic colourants are toxic and some are potentially

carcinogenic if compared to natural pigments. The U.S. Food and Drug

Administration (USFDA) reported that 3 of 18 approved synthetic dyes caused

cancer in animals where 31,000 lbs of these dangerous dyes had already been

consumed by the U.S. public. Some of the examples for these carcinogenic

colourants are “Butter yellow" which was used for butter and olive oil, "light green

SF" for green peas, and thiourea used to prevent oranges from spoiling [1].

2x single spacing

As an alternative, the natural pigments were introduced to replace the

synthetic pigments due to their safety image, general health and numerous other

important properties [2].

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1.2 Statement of Problem

(Teks bermula di sini, 1.27 cm di jidar kiri dan bersambung ke jidar kiri bagi

baris kedua dan seterusnya serta “justify” kiri dan kanan. Taip menggunakan jarak

satu setengah baris dan perenggan berikutnya jarak teks dari jidar kiri 1.27 cm.)

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Lampiran 16: Contoh Bab

29

(Teks dari muka surat sebelum ini disambung di sini.)

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2.4 Bacteria and Pigments

2x single spacing

Microorganisms such as bacteria are important for many reasons, particularly

because they produce things that are of value to us [11]. One of the most important

product produce by bacteria is pigment. There are several examples of bacteria and

its pigment. Chromobacterium lividium, was rod-shaped, gram-negative, and

produced viscid colonies with abundant violet pigment on Tryptone glucose yeast

extract agar. The pigment appeared to be similar to that of other known species of

Chromobacterium and assisted in identification of the genus of the causative

organism [12].

2x single spacing

Recently, Alteromonas rubra was reported to produce new prodigiosin-like

pigments. Alteromonas rubra have three strains of red, antibiotic-producing marine

bacteria, which are commonly found in Mediterranean coastal waters during the

autumn months.

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2.4.1 Primary and Secondary Metabolites

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Pigments can be produced either as primary or secondary metabolites of

bacterial growth. Primary metabolite is one that is formed during the growth phase of

the microorganism. The products (pigments) were formed in parallel with growth

and the formations of products are not dependent on growth conditions (composition

of the medium). In addition, the production of pigments is not significantly

overproduced. The pigments are not essential for the growth and reproduction of

bacteria because the cell can still maintain normal growth rate after bleaching where

all the pigments have been removed [18]. An example of bacteria which produces

pigments as primary metabolites is Clavibacter agropyri [19].

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Lampiran 17: Contoh Bahagian

30

4.1 Growth Profile of S. Marcescens

2x single spacing

Figure 4.1 shows the growth profile of S. marcescens in NB. The normal

growth profile consisted of three phases; lag, log and stationary phase.

2x single spacing

Figure 4.1: Growth profile of S. marcescens (center)

2x single spacing

For this growth profile, lag phase was not visible as exponential growing

culture was used to inoculate the medium causing cells to commence growth

immediately. The log phase lasted for about 8 hours after inoculation into fresh

medium. After eight hours the growth was slow and the population reached the

stationary phase. This might be due to the depletion of nutrients present in the growth

medium [13].

Jika tajuk graf, rajah atau ilustrasi melebihi dua baris (spacing 1, justify kiri dan

kanan)

Figure 4.3: Colour intensity of pigments in different media; (a) nutrient broth, (b)

brown sugar 10%, (c) brown sugar 1%, (d) liquid pineapple waste, (e) control liquid

pineapple waste, (f) control brown sugar 10%, (g) control brown sugar 1%, (h)

control nutrient broth.

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0.2

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1

1.2

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1.8

0 5 10 15 20 25 30

Time (Hours)

Op

tic

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en

sit

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D 6

00

StationaryLog

Lampiran 18: Contoh Memasukkan Graf Dalam Teks

31

Figure 4.2: Culture of S. marcescens in nutrient broth grown at: (a) 25oC, (b) 30

oC

and 37oC.

4.2.2 Effect of Different Media

S. marcescens was grown in different media (NB, LPW 100%, BS 1% in

LPW, BS 10% in LPW, BS 1% in DDW and BS 10% in DDW) in order to select the

best medium for the pigments production. The production of red pigments differed

considerably, depending on the medium used.

(a) (b) (c) (d) (e) (f) (g) (h)

Figure 4.3: Colour intensity of pigments in different media; (a) nutrient broth, (b)

brown sugar 10%, (c) brown sugar 1%, (d) liquid pineapple waste, (e) control liquid

pineapple waste, (f) control brown sugar 10%, (g) control brown sugar 1%, (h)

control nutrient broth.

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Lampiran 19: Contoh Memasukkan Gambar Dalam Teks

32

4.5.1.1 Colourfastness Test

Colourfastness of a fabric refers to the ability of the fabric to maintain its

colour under several external conditions. These include colourfastness to crocking,

washing, perspiration, and light. The basic principle for colourfastness testing was to

compare the tested fabrics with the Gray Scale for change in colour and staining. The

AATCC (American Association of Textile Chemists and Colorists) ratings for

change in colour and staining ranged from 1-5 were used [29]. The standard method

and equipments used in testing of fabrics is shown in Table 4.2.

Table 4.2: The standard method and equipment used for the testing of fabrics

(tajuk jadual sebaris, center)

Fabric testing Standard Method Equipment

Colourfastness to MS ISO 105-C01-1996 Auto wash, colour

matching cabinet

i) Washing MS ISO 105-A05-2003 Change in colour

MS ISO 105-A04-2003 Staining

ii) Perspiration MS ISO 105-E04-1996 Perspirometer

MS ISO 105-A05-2003 Change in colour

MS ISO 105-A04-2003 Staining

iii) Light MS ISO 105-B02-2001 Light fastness tester

iv) Rubbing/Crocking MS ISO 105-X12-2001 Crockmeter

MS ISO 105-A04-2003 Staining

(Jika tajuk jadual panjang, tajuk ditulis mulai sebelah kiri, justify, langkau sebaris)

Jadual 3.9: Jadual peratus kandungan minyak dalam hampas buah kelapa sawit

yang ditentukan dengan kaedah gravimetri (langkau satu baris jika

panjang)

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Lampiran 20: Contoh Jadual Dalam Teks

33

Table 2.2: The 1

H-NMR and 13

C-NMR Data of Compounds (118) and 4-hydroxyl-

onchocarpin

Carbons Compound (118) 4-hydroxylonchocarpin [68]

13C

NMR

1H-NMR

13C

NMR

1H-NMR

1 127.5 - 127.4 -

2 131.9 7.74 (1H, d, J =8.6 Hz) 131.9 7.72 (1H, d, J = 8.6 Hz)

3 116.8 6.91 (1H, d, J =8.6 Hz) 116.8 6.89 (1H, d, J = 8.6 Hz)

4 160.4 - 160.3 -

5 116.8 6.91 (1H, d, J =8.6 Hz) 116.8 6.89 (1H, d, J = 8.6 Hz)

6 131.9 7.74 (1H, d, J =8.6 Hz) 131.9 7.72 (1H, d, J = 8.6 Hz)

118.1 7.75 (1H, d, J = 15.6

Hz)

117.9 7.73 (1H, d, J = 15.2 Hz)

145.6 7.84 (1H, d, J = 15.6

Hz)

145.6 7.82 (1H, d, J = 15.2 Hz)

C=O 193.2 - 193.2 -

1 109.9 - 109.8 -

2 161.2 14.05 (s, OH) 161.2 n.a

3 114.9 - 114.9 -

4 161.7 - 162.0 -

5 108.8 6.36 (1H, d, J = 8.9 Hz) 108.8 6.33 (1H, d, J = 8.9 Hz)

6 132.2 8.05 (1H, d, J = 8.9 Hz) 132.2 8.02 (1H, d, J = 8.9 Hz)

1 116.3 6.75 (1H, d, J =10.0 Hz) 116.3 6.67 (1H, d, J = 10.0 Hz)

2 129.2 5.71 (1H, d, J =10.0 Hz) 129.2 5.68 (1H, d, J = 10.0 Hz)

3 78.5 - 78.5 -

4 28.5 1.44 (6H, s)

28.5 1.48 (6H, s)

5 28.5 28.5

n.a - not available

Nota: Jadual mesti di’centerkan’. Saiz font di dalam jadual boleh dikecilkan

sehingga size 10. Pastikan data di dalam jadual berada ditengah-tengah baris.

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Lampiran 21: Contoh kedua Jadual Dalam Teks

34

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REFERENCES

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(1.27 cm)

1. Burkill, I.H. (1935). A Dictionary of the Economic Products of the Malay

Peninsula, Ministry of Agriculture and Cooperatives, Kuala Lumpur,

Malaysia, 123-140.

2. Wade Jr., L.G. (2006). Organic Chemistry. 6th.

Ed. New Jersey, USA:

Prentice Hall. 189-278.

3. Endud, S. and Wong, K.-L. (2007). Mesoporous Silica MCM-48 Molecular

Sieve Modified with SnCl2 in alkaline Medium for Selective Oxidation of

Alcohol, Microporous and Mesoporous Materials. 101, 256-263.

4. Sirat, H.M., Ahmad, F., Susanti, D. and Ali, R.M. (2007). Antioxidant and

Cytotoxic Flavonoids from the Flowers of Melastoma malabathricum L.

Food Chemistry. 103, 710-716.

5. Sukiman Sarmani (1987). Pencemaran Radioaktif. dlm. Ahmad Badri

Mohamad, Perspektif Persekitaran, Petaling Jaya: Fajar Bakti. 71-87.

6. Sheta, A.F. and Jong, K.D. (1996). Parameter Estimation of Nonlinear

Systems in Noisy Environments Using Genetic Algorithms. Proceedings of

the 1996 IEEE International Symposium on Intelligent Control. September

15-18. Dearborn, Michigan: IEEE, 360 - 365.

7. Tan Yan Peng (2001). Kajian Minyak Pati Ocimum basilicum dan Mentha

arvensis. Universiti Teknologi Malaysia: Tesis Ijazah Sarjana Muda.

8. Lindgren, A.E. (1988). Screen Room Air Inlet and Wave Guard. (U.S. Patent

6, 379, 457).

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Lampiran 22: Contoh Senarai Rujukan (mengikut sistem nombor)

35

Lam

pir

an 1

: S

pek

trum

In

fram

erah

Bag

i K

RG

1

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Lampiran 23: Contoh Lampiran 1

36

Final Year Project Proceeding, Session 2011/2012

Department of Chemistry, Faculty of Science, UTM (Times New Roman, Font 11, Italic)

PHYTOCHEMICALS FROM THE LEAVES OF ARTOCARPUS

SP. (Times New Roman, Font 14, Bold, ALL CAPS) (Enter)

(Enter)

Nur Azlin Othman and Shajarahtunnur Jamil (Times New Roman, Font 11, Bold)

Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, 81310 Johor

Bahru. (Times New Roman, Font 11, Italic)

(Enter)

Abstract (Times New Roman, Font 11, Bold)

(Enter)

Chemical investigation of the extracts from the leaves of Artocarpus sp. furnished six known

compounds, carpachromene (1), cycloartocarpesin (2), norartocarpetin (3), 2′-hydroxy-

4,4′,6′-trimethoxychalcone (4), friedelin (5) and lupeol (6). The structures of these

compounds were determined on the basis of spectroscopic data and also comparison with

data reported in the literature. Compounds (1), (2), (3) and (6) exhibited cytotoxic activity

against MCF-7 human cancer cell. (Not more than 200 words, 1 paragraph, Times New

Roman, Font 11).

(Enter)

Keywords: Artocarpus, Moraceae, flavone, chalcone, cytotoxic (Not more than 5 keywords,

Times New Roman, Font 11)

(Enter)

(Enter) Introduction (Times New Roman, Font 11, Bold) (Enter)

Artocarpus is the most encountered genus, representatives of the Moraceae which distributed

over tropical and tropical regions. The genus Artocarpus consists of approximately 50

species, which are indigenous to the region of Southeast Asia [1]. However, the greatest

diversity is in Indonesia, Malaysia, and the Philippines. In Malaysia, there are 9 genera and

137 species, mostly are tropical from lowlands to mountain forests. Artocarpus species is

noted as an abundant source of flavonoids, a class compounds which has chemistry and

biological activity properties attraction including antimicrobial activity, antioxidant activity,

antiplatelet activity, anti-inflammatory activity and cytotoxic activity against various cell

lines [2-3]. (Enter)

Artocarpus fulvicortex is one of Malaysian rare Artocarpus species. This plant is

locally known as „keledang tampang gajah‟. It is medium-sized tree with orange brown or

reddish brown bark [4]. Within the scope of continuation search for bioactive compounds

from natural plants, the leaves of A. fulvicortex were further investigated. In this paper, we

report the isolation and structural elucidation of six known compounds (1-6). In addition, all

the compounds were evaluated for their cytotoxic activity against TE-1, A549, MCF-7,

C33A, and CaCO2 cells. (Times New Roman, Font 11, justify)

(Enter)

(Enter)

Experimental (Times New Roman, Font 11, Bold) (Enter)

Vacuum liquid chromatography (VLC) and gravity column chromatography were carried out

by using Merck silica gel 60 (230-400 mesh) and Merck silica gel 60 (70-230 mesh)

respectively. Thin layer chromatography (TLC) was performed on 0.20 mm precoated silica

gel aluminium sheets (Merck Kieselgel 60 F254). Spots were visualized by UV light (254 nm

and 365 nm) and sprayed with vanillin sulphuric acid reagent. Melting points were measured

by using melting point apparatus equipped with microscope, Leica Gallen III and were

uncorrected. The 1H NMR and

13C NMR (400 MHz and 100 MHz) spectra were recorded on

a Bruker Avance 400 spectrometer. Residual solvents were used as an internal standard.

Lampiran 24: Contoh Prosiding PSM

37

Infrared spectra were recorded on Perkin-Elmer series 1600 spectrophotometer as thin

film

(NaCl windows) for liquid samples or KBr pellet for solid samples. Gas chromatography

(GC) analysis was carried out on Hewlett Packard HP6890. GC-MS analysis was equipped

with Wiley Library Software.(Times New Roman, Font 11, justify) (Enter) (Enter)

(1) (2) (3)

(4) (5) (6) (Enter) (Enter) Plant Material (Times New Roman, Font 11, Bold, Italic) (Enter) Leaves of Artocarpus sp.with voucher number HTBP 962 were collected from Hutan Simpan Pelagak, Terengganu in September 2007. (Times New Roman, Font 11, justify) (Enter) Extraction and Isolation (Times New Roman, Font 11, Bold, Italic) (Enter)

The dried leaves of Artocarpus sp. (1.5 kg) was ground and sequentially extracted using

petroleum ether, CH2Cl2, EtOAc, and MeOH (4L each) at room temperature for 48 hours.

The extracts were filtered and extractions were repeated twice by adding fresh solvents. The

extracts were concentrated by using rotary evaporator to give viscous dark green sticky of

PE crude extract (16.1 g), CH2Cl2 crude extract (18.0 g), EtOAc crude extract (17.9 g) and

MeOH crude extract (78.5 g). A portion of MeOH crude of the leaves (50.0 g) was further

suspended in water, and then partitioned with dichloromethane (AFLMD) and ethyl acetate

(AFLME). The AFLMD crude extract (1.0 g) was chromatographed over Si gel (60 g),

eluting with n-hexane-EtOAc (9:1) to give 1 (15.3 mg). A portion of CH2Cl2 crude extract of

the leaves (12 g) was subjected to Si gel VLC (250 g) and eluted with n-hexane, n-hexane-

EtOAc, EtOAc, EtOAc-MeOH and MeOH in order of increasing the polarity gave seven

major fractions. Fraction 6 (2.8 g) was subjected to Si gel column chromatography (70 g)

and eluted by n-hexane-EtOAc (4:1) to afford (1) (99.2 mg). The EtOAc extract of the leaves

(10 g) was subjected to Si gel VLC (280 g) and eluted under gradient conditions with

increasing amounts of EtOAc in n-hexane to give twenty fractions. Fractions with a similar

pattern on TLC were combined to give seven major fractions. Fraction 3 (0.9 g) was further

purified by Si gel column chromatography (50 g) and eluted with n-hexane-EtOAc (4:1) to

give (2) (21.2 mg). The AFLME (1.0 g) was also subjected to Si gel column chromatography

(50 g) and eluted by n-hexane-EtOAc (7:3) to afford (3) (13.6 mg). The PE extract (15.0 g)

was fractionated by Si gel VLC (280 g) and eluted with n-hexane, n-hexane-Et2O, Et2O-

EtOAc, EtOAc, EtOAc-MeOH and MeOH in order of increasing the polarity to afford

twenty five fractions. The fractions with similar pattern of TLC profile were combined to

give six major fractions. Recrystallization of fraction 1 using Et2O gave compound (4)

O O

OH O

OH

12

13 11

10

9

67

88a

54a 4

3

21'

2'

3'

4'

5'

6'

O O

OH O

OH

12

13 11

10

9

67

88a

54a 4

3

21' 3'

4'

5'

6'

OH2'

O

OH O

OH

67

88a

54a 4

3

21' 3'

4'

5'

6'

OH2'

HO

MeO OMe

OMe

OOH

3'

23

4

5

6

14'

5'6'

1'2'

O

H

HO

38

(115.8 mg). Fraction 4 (3.1 g) was purified by Si gel column chromatography (150 g) using

n-hexane-EtOAc (9:1) as an eluent, to yield (5) (9.3 mg) and (6) (23.6 mg). (Times New

Roman, Font 11, justify) (Enter) (Enter) Results and Discussion (Times New Roman, Font 11, Bold) (Enter)

Sequential cold extraction of powdered leaves of Artocarpus (1.5 kg) at room temperature by

using different polarity of organic solvents for 48 hours each, afforded dark green sticky of

PE crude extract (16.1 g, 1.1%), dark green sticky of CH2Cl2 crude extract (18.0 g, 1.2%),

dark green sticky of EtOAc crude extract (17.9 g, 1.2%), and brown gum of MeOH crude

extract (78.5 g, 4.2%). The MeOH extract was further suspended in water, then partitioned

with CH2Cl2 and EtOAc to yield CH2Cl2-soluble extract (AFLMD) (1.1 g, 1.4%) and

EtOAc-soluble extract (AFLME) (1.2 g, 1.5%). (Enter)

Compound (1) was obtained from the CH2Cl2 crude extract as pale yellow needles

(99.2 mg, 0.55%) with m.p. 236-238ºC, lit. 239-241ºC [5]. The TLC analysis with vanillin

sulphuric acid spraying reagent revealed a yellow spot suggesting a flavonoid. The IR

spectrum of compound (1) showed the presence of hydroxyl group at 3446 cm-1

, chelated

carbonyl group at 1656 cm-1

, C=C aromatic ring at 1615 cm-1

, and C-O stretching at 1297

cm-1

respectively. The UV spectrum displayed maximum absorptions at 236, 306, and 343

nm in MeOH, which was typical for a flavone derivative. The bathochromic shift induced by

NaOMe indicated the occurrence of free hydroxyl group at C-4' in ring B. While, after the

addition of AlCl3, the bathochromic shift of band II still occured, thus suggested the presence

of hydroxyl group at C-5 [6]. Analysis of the 1H NMR spectrum revealed the characteristic

signals of 2,2-dimethylchromene group. It was represented by a singlet signal integrated for

six protons at δ 1.49 corresponding to two methyl groups, H-12 and H-13, together with two

doublets at δ 6.68 and δ 5.78 (J = 10.0 Hz each) for the pyran olefinic protons, H-9 and H-10

respectively. Two doublets which formed an AA′BB′ spin system were also observed at δ

7.97 and δ 7.05 (2H each, J = 8.8 Hz) for the aromatic protons in the ring B. The isolated

protons appeared as singlets at δ 6.67 and δ 6.49 corresponding to H-3 and H-8 respectively.

A singlet signal resonated at downfield region δ 13.44 was assigned for chelating hydroxyl

group at C-5. The correlations between these protons can be observed in the 1H-

1H COSY

spectrum (Appendix 4). The signal at δ 7.97 (H-2′/H-6′) was coupled with the signal at δ

7.05 (H-3′/H-5′). Similarly, signal at δ 6.68 (H-9) was coupled with the signal at δ 5.78 (H-

10).

(continue.....) (Times New Roman, Font 11, justified) (Enter) (Enter)

Conclusion (Times New Roman, Font 11, Bold) (Enter) The sentences start here…..(Times New Roman, Font 11, justify) (Enter) (Enter)

References (Times New Roman, Font 11, Bold) (Enter)

1. Fabricant, D. S. and Farnsworth, N. R. (2001). The Value of Plants Used in

Traditional Medicine for Drug Discovery. Environmental Health Perspectives, 109:

69-75.

2. Newman, D. J., Cragg, G. M., Snader, K. M. (2000). The influence of Natural

Products upon Drug Discovery. Nat. Prod. Rep., 17, 215-234.

3. Mohammad, S. (2006). Anticancer Agents from Medicinal Plants. Bangladesh J.

Pharmacol., 1, 35-41.

4. Burkill, I. H. (1966). A Dictionary of the Economic Products of the Malay

Peninsula. Ministry of Agriculture and Cooperatives: Kuala Lumpur, 1-356.

5. Pecchio, M., Solis, P. N., Perez, J. L. L., Vasquez, Y., Rodriguez, N., Olmedo, D.,

Correa, M., Feliciano, A. S., Gupta, M. P. (2006). Cytotoxic and Antimicrobial

Benzophenones from the Leaves of Tovomita longifolia. J. Nat. Prod., 69, 410-413.

39

6. Hakim, E.H., Achmad, S.A., Juliawaty, L.D., Makmur, L., Syah, Y.M., Aimi, N.,

Kitajima, M., Takayama, H., Ghisalberti, E.L. (2006). Prenylated flavonoids and

related compounds of the Indonesian Artocarpus (Moraceae). J. Nat. Med. 60,161-

184.

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Department of Chemistry

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