Dec2015/Jan 2016 Time: 2 hours

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1 UNIVERSITI MALAYA UNIVERSITY F MALAYA PEPERIKSAAN IJAZA SARJANA MUDA SAINS EXAMINATIN FR TE DEGREE F BACELR F SCIENCE PEPERIKSAAN IJAZA SARJANA MUDA SAINS DENGAN PENDIDIKAN EXAMINATIN FR TE DEGREE F BACELR F SCIENCE WIT EDUCATIN SESI AKADEMIK 2015/2016 : SEMESTER 1 ACADEMIC SESSIN 2015/2016 : SEMESTER 1 SCES3324 : KIMIA SEBATIAN SEMULAJADI NATURAL PRDUCT CEMISTRY Dis 2015/Jan 2016 Masa: 2 jam Dec2015/Jan 2016 Time: 2 hours ARAAN KEPADA CALN: INSTRUCTINS T CANDIDATES: Jawab SEMUA soalan Answer ALL question Untuk Soalan 1, sila jawab di kertas jawapan dan Lampiran I - VI. For Question 1, please answer in the answer script and Attachments I - VI. Sila kepilkan Lampiran I VI bersama-sama dengan skrip jawapan anda. Please attach Attachments I VI together with your answer script. (Kertas soalan ini mengandungi 5 soalan dalam 8 halaman yang dicetak) (This question paper consists of 5 questions on 8 printed pages)

2 1. Kamu dibekalkan dengan satu set data NMR ( 1, 13 C, CSY, SQC, and MBC) yang sepadan dengan salah satu sebatian di atas (Lampiran I VI). Berdasarkan spektrum yang dibekalkan (Lampiran I VI), tentukan sebatian (A atau B) yang sepadan dengan data spektrum yang disediakan. Jelaskan jawapan anda. Sebagai sebahagian daripada jawapan anda, anda dikehendaki menandakan setiap puncak dalam spektrum NMR 1 dan 13 C (Lampiran I dan II). Sila kepilkan semua spektrum-spektrum ini (Lampiran I VI) bersama-sama dengan kertas jawapan anda. (Spektrum CSY, SQC, dan MBC di Lampiran III VI dibekalkan untuk membantu anda dalam proses penandaan puncak.) You are provided with a set of NMR data ( 1, 13 C, CSY, SQC, and MBC), which corresponds to one of the above compounds (Attachments I VI). Based on the spectra provided in Attachments I VI, determine which of the two compounds (A or B) corresponds to the spectral data provided. Explain your answer. As part of your answer, you are required to assign each peak in the 1 and 13 C NMR spectra (Attachments I and II). Please attach all spectra (Attachments I VI), together with your answer script. (The CSY, SQC, and MBC spectra in Attachments III VI are provided to assist you in the assignment.) (30 markah/marks) 2. (a) Tulis nota ringkas tentang peranan sebatian semulajadi dalam penemuan ubat-ubatan. Write short notes about the role of natural products in drug discovery. (b) (i) Berikan definisi bagi alkaloida. Provide the definition of alkaloid. (6 markah/marks) (ii) Gariskan satu kaedah pengekstrakan alkaloida daripada satu sample tumbuhan. utline an extraction method of alkaloids from a plant sample. 2/8

3 (iii) Berikan 2 (dua) kaedah pengesanan alkaloida dalam ekstrak mentah. Provide 2 (TW) detection methods of alkaloids in a crude extract. (8 markah/marks) (c) Kelaskan setiap sebatian-sebatian yang berikut (C G) mengikut kelas sebatian semulajadi (cth., terpena, alkaloida, dsb.). Classify the following compounds (C G) according to the class of natural product to which they belong (e.g., terpenes, alkaloids, etc.). (6 markah/marks) 3. (a) (i) Takrifkan metabolit primer dan sekunder. Define the primary and secondary metabolites. applikasi (ii) (3 markah/marks) Jelaskan kepentingan bahan semulajadi dalam perasa dan makanan Explain the importance of natural products in flavoring and food applications. (3 markah/marks) 3/8

4 (iii) Berikan contoh-contoh bagi aktiviti biologi asid hidroksi cinnamik (CAs) dalam rajah (1) Provide examples of the biological activity of hydroxy cinnamic acids (CAs) in figure (1). (3 markah/marks) R 4 R 3 R 2 R 1 C o-coumaric acid, R1 = m-coumaric acid, R 2 = p-coumaric acid, R 3 = Caffeic acid, R 2 = R 3 = Ferulic acid, R 2 = C 3 ; R 3 = Cinnamic acid, R 1 = R 2 = R 3 = R 4 = Sinapic acid, R 2 = R 4 = C 3 ; R 3 = Chlorogenic acid Rajah 1 Figure 1 Figure (1) (b) Jelaskan dan lengkapkan jalan bioisintetik seperti yang ditunjukkan dalam rajah (2) berikut: Describe and complete the following biosynthetic pathway shown in figure (2): Rajah 2 Figure 2 (6 markah/marks) 4/8

5 4. (a) Tuliskan mekanisme pengkupelan oksidatif fenolik dalam rajah (3) dan berikan nama kelas bagi metabolit sekunder tersebut. Draw the oxidative phenolic coupling mechanism in figure (3) and provide the names of the secondary metabolites classes. single electon oxidation E dimerization NADP 3 C 3 C NADP F 3 C Rajah 3 Figure 3 (3) 3 C C 3 C 3 (11 markah/marks) 5/8

6 (b) Berikan Reagan-reagan (G,, I, J) bagi langkah dalam rajah (4) berikut: Provide the reagents (G,, I, J) for the following pathway in figure (4): G Stigmasterol N I J Rajah 4 Figure (4) 4 progesterone (4 markah/marks) 5. (a) Lengkapkan persamaan bagi langkah yang ditunjukkan dalam rajah (5). Complete the equations of the enclosed pathway in figure (5). -C C C P 2 C + K L Shikimate M N N 2 P Rajah 5 Figure 5 (5) (10 markah/marks) 6/8

7 (b) Lengkapkan tindak balas dalam rajah (6) berikut: Complete the following reaction in figure (6): acetoactylcoa Q Claisen condensation SCoA Aldol condensation ydrolysis R SCoA NADP C SCoA C NADP S Rajah 6 Figure 6 (4 markah/marks) 7/8

8 (c) Berikan struktur kimia bagi sebatian-sebatian (T, U, V, W) berikut dan Reagan (a) dalam rajah (7): Give the chemical structures for the following compounds ( T, U, V, W, ) and the reagent (a) in figure (7): i. Ac 2 ii. Br 2 T Cholesterol Cholesteryl acetate dibromide Ac Cr 3 U i. Zn/Ac ii. hydrolysis Ac i. Ac 2 ii. Na Br Br CPh V a ppenaure oxid. hydrolysis K W Testosterone Rajah 7 Figure (7) 7 (6 markah/marks) TAMAT END 8/8