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I Chemical Constituents from Rhodomyrtus Tomentosa Chemical Constituents from Rhodomyrtus tomentosa (Aiton) Hassk. and Antibacterial Activity Asadhawut Hiranrat A Thesis Submitted in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in Organic Chemistry Prince of Songkla University 2010 Copyright of Prince of Songkla University i Thesis Title Chemical Constituents from Rhodomyrtus tomentosa (Aiton) Hassk. and Antibacterial Activity Author Mr. Asadhawut Hiranrat Major Program Organic Chemistry Major Advisor: Examining Committee: .…………………………………...………… ………………………………..…Chairperson (Assoc. Prof. Dr. Wilawan Mahabusarakam) (Assoc. Prof. Dr. Kan Chantrapromma) ……………………………………………… Co-advisor: (Assoc. Prof. Dr. Wilawan Mahabusarakam) ………………………………………………. ……………………………………………… (Assoc. Prof. Chanita Ponglimanont) (Assoc. Prof. Chanita Ponglimanont) ……………………………………………… (Assoc. Prof. Dr. Chatchanok Karalai) The Graduate School, Prince of Songkla University, has approved this thesis as a partial fulfillment of the requirements for the Doctor of Philosophy degree in Organic Chemistry. ……………………….…………….….. (Prof. Dr. Amornrat Phongdara) Dean of Graduate School ii ชื่อวิทยานิพนธ องคประกอบทางเคมีจากโทะและฤทธิ์ตานแบคทีเรีย ผูเขียน นายอัษฎาวุธ หิรัญรัตน สาขาวิชา เคมีอินทรีย ปการศึกษา 2553 บทคัดยอ โทะ (Rhodomyrtus tomentosa) เปนพืชในวงศชมพู (Myrtaceae) สวนสกัดหยาบไดคลอโร มีเทนและอะซิโตนจากใบโทะมีฤทธิ์ในการยับยั้งการเจริญของแบคทีเรีย Staphylococcus aureus ATCC 25923 และ methicillin-resistant S. aureus (MRSA) NRPC R01 ดวยคาความเขมขนต่ําสุด (MIC) 31.25 และ 62.5 g/mL ตามลําดับ การศึกษาองคประกอบทางเคมีของใบ ตนและผลโทะเพื่อ หาสารที่แสดงฤทธิ์ในการยับยั้งการเจริญของเชื้อแบคทีเรีย แยกสารองคประกอบได 41 สาร เปน สารกลุมเอซิลฟลอโรกลูซินอล (acylphloroglucinols) จํานวน 11 สาร คือ rhodomyrtosone A (ART2), rhodomyrtosone H (ART3), rhodomyrtosone C (ART4), rhodomyrtone (ART6), endoperoxide G3 (ART8), rhodomyrtosone B (ART9), rhodomyrtosone D (ART11), rhodomyrtosone E (ART18), rhodomyrtosone G (ART19), rhodomyrtosone F (ART20) และ rhodomyrtosone I (ART38) สารกลุมฟลาโวนอยด (flavonoids) จํานวน 4 สาร คือ combretol (ART7), 3,4',5',7-tetra-O-methylmyricetin (ART13), 3,3',5',7-tetra-O-methylmyricetin (ART16) และ 3,3',4',5'-tetra-O-methylmyricetin (ART17) สารกลุมเทอพีนอยด (terpenoids) จํานวน 7 สาร คือ (6R,7E,9S)-9-hydroxy-4,7-megastigmadien-3-one (ART12), loliolide (ART14), 3-O-E- coumaroylmaslinic acid (ART22), 3-O-Z-coumaroylmaslinic acid (ART23), 3-O-E-coumaroyl oleanolic acid (ART32), arjunolic acid (ART34) และ oleanolic acid (ART39) สารกลุม สเตียรอยด (steroids) จํานวน 3 สาร คือ -sitosterol (ART5), -sitosterol glucopyranoside (ART24) และ stigmast-4-en-3-one (ART37) อนุพันธของกรดแอลลาจิก (ellagic acid derivatives) จํานวน 3 สาร คือ 3,3',4-tri-O-methylellagic acid (ART10), 4-O-[-D-glucopyranosyl- iii tetraacetate]-3,3',4'-tri-O-methylellagic acid (ART28) และ 3-O-methylellagic acid 4-O-- rhamnopyranoside (ART41) อนุพันธของกรดฟลาเวลลาจิก (flavellagic acid derivatives) จํานวน 2 สาร คือ 3',4'-dioxymethylene-3,4-di-O-methylflavellagic acid (ART25) และ 3,4,3',4'-tetra-O- methylflavellagic acid (ART31) สารกลุมอนุพันธเบนซีน (benzenoids) จํานวน 6 สาร คือ -tocopherol (ART1), trans-triacontyl-4-hydroxy-3-methoxycinnamate (AR21), trans-triacontyl- 4-hydroxycinnamate (ART30), 4-hydroxy-3-methoxybenzoic acid (ART35), gallic acid (ART36) และ methyl gallate (ART40) อนุพันธลิกแนน (lignans) จํานวน 1 สาร คือ 9,9'-O-diferuloyl-(-)-secoisolariciresinol (ART33) อนุพันธของบิวไทโรแลคโทน (butyrolactone derivatives) จํานวน 1 สาร คือ (3aS*,6aR*)-3a-(hydroxymethyl)-2,2-dimethyldihydro-furo[3,4-d] [1,3]dioxol-4(3aH)-one (ART15) และน้ําตาล จํานวน 3 สาร คือ -D-glucopyranoside penta- acetate (ART26), -D-glucopyranoside penta-acetate (ART27) และ sucrose octa-acetate (ART29) สาร 11 สาร คือ ART2, ART3, ART4, ART9, ART11, ART15, ART18, ART19, ART20, ART31 และ ART38 เปนสารที่ยังไมมีรายงานการวิจัย โครงสรางของสารประกอบเหลานี้ วิเคราะหดวยขอมูลทางสเปกโทรสโกป UV IR NMR และ MS นอกจากนี้ยังไดเปรียบเทียบขอมูล ทางสเปกโทรสโกปกับสารที่มีรายงานการวิจัยแลว การทดสอบฤทธิ์ของสารกลุมเอซิลฟลอโรกลูซินอล (ART2, ART4, ART6, ART9, ART11, ART18, ART19 และ ART20) ในการตานเชื้อแบคทีเรีย S. aureus, MRSA และ Streptococcus pyogenes DMST 101 พบวา rhodomyrtone (ART6) และ rhodomyrtosone B (ART9) สามารถยับยั้งการเจริญของเชื้อทั้งสามสายพันธุ ดวยคาความเขมขนต่ําสุด (MIC) 0.39, 6.25 g/mL 0.39, 12.5 g/mL และ 0.39, 3.125 g/mL ตามลําดับ นอกจากนี้ยังพบวา rhodomyrtosone G (ART19) ยับยั้งการเจริญของ S. aureus และ MRSA ดวยคาความเขมขนต่ําสุด (MIC) 1.56g/mL และ rhodomyrtosone D (ART11) ยับยั้งการเจริญของ S. pyogenes ดวยคา ความเขมขนต่ําสุด (MIC) 12.5 g/mL iv HO O O R2 OH O O H O HO R1 ART1 ART2 : R1 = H, R2 = isovaleryl ART3 : R1 = isovaleryl, R2 = H O O O O O O OH O RO ART5 : R = H ART4 ART24 : R = --D-glucose R2 R3 R2 O O OH R1 O OCH3 R1 OCH3 O R3 OH OH O ART6 : R = isovaleryl, R = H, R = isobutyl 1 2 3 ART7 : R1 = R2 = R3 = OCH3 ART9 : R1 = H, R2 = isovaleryl, R3 = isobutyl ART13 : R1 = R3 = OCH3, R2 = OH ART19 : R1 = 2-methylbutyryl, R2 = H, R3 = isobutyl ART16 : R1 = R2 = OCH3, R3 = OH ART38 : R1 = isovaleryl, R2 = H, R3 = phenyl ART17 : R1 = OH, R2 = R3 = OCH3 OH O O O O O O O H O ART8 O O ART11 O R1 OR ART10 : R1 = R2 = H, R3 = R4 = CH3 O 2 ART25 : R1 = OH, R2 = CH3, R3, R4 = -CH2- R3O OCH3 ART28 : R1 = H, R2 = --D-glucose tetra-acetate, R3 = R4 = CH3 O ART31 : R1 = OH, R2 = R3 = R4 = CH3 R4O : R = R = R = H, R = --D-rhamnose O ART41 1 3 4 2 v OH HO O O O O OH O O O ART12 ART14 ART15 O R O ART21 : R = OCH 28 3 ART30 : R = H HO O O O O O O O OH O OH H H O O O O O O O O ART18 ART20 ART22 : R1 = trans-coumaroyl, R2 = OH, R3 = H ART23 : R1 = cis-coumaroyl, R2 = OH, R3 = H CO H 2 : R = trans-coumaroyl, R = R = H R2 ART32 1 2 3 ART34 : R1 = H, R2 = R3 = OH : R = R = R = H R1O ART39 1 2 3 R3 AcO AcO OAc OAc OAc O O O O AcO AcO AcO O AcO AcO OAc AcO OAc OAc OAc OAc OAc OAc ART26 ART27 ART29 vi O R1 OR3 HO R2 ART35 : R1 = OCH3, R2 = R3 = H ART36 : R = R = OH, R = H 1 2 3 O ART40 : R1 = R2 = OH, R3 = CH3 ART37 O OCH O 3 H CO 3 OH OH HO O OCH3 O OCH3 OH ART33 vii Thesis Title Chemical Constituents from Rhodomyrtus tomentosa (Aiton) Hassk. and Antibacterial Activity Author Mr. Asadhawut Hiranrat Major Program Organic Chemistry Academic Year 2010 ABSTRACT Rhodomyrtus tomentosa (Aiton) Hassk. is a flowering plant belonging to the family Myrtaceae. The preliminary study has revealed that the crude CH2Cl2 and Me2CO extracts from its leaves exhibited strong antibacterial activities against Stephylococcus aureus ATCC 25923 and methicillin-resistant S. aureus NRPC R01 (MRSA) with MIC values of 31.25 and 62.5g/mL, respectively. Investigation of the chemical constituents from the leaves, stems and fruits of R. tomentosa yielded forty one compounds. They were determined to be eleven acylphloroglucinols: rhodomyrtosone A (ART2), rhodomyrtosone H (ART3), rhodomyrtosone C (ART4), rhodomyrtone (ART6), endoperoxide G3 (ART8), rhodomyrtosone B (ART9), rhodomyrtosone D (ART11), rhodomyrtosone E (ART18), rhodomyrtosone G (ART19), rhodomyrtosone F (ART20) and rhodomyrtosone I (ART38), four flavonoids: combretol (ART7), 3,4',5',7-tetra-O-methylmyricetin (ART13), 3,3',5',7- tetra-O-methylmyricetin (ART16) and 3,3',4',5'-tetra-O-methylmyricetin (ART17), seven terpenoids: (6R,7E,9S)-9-hydroxy-4,7-megastigmadien-3-one (ART12), loliolide (ART14), 3-O-E-coumaroylmaslinic acid (ART22), 3-O-Z-coumaroyl- maslinic acid (ART23), 3-O-E-coumaroyloleanolic acid (ART32), arjunolic acid (ART34) and oleanolic acid (ART39), three steroids: -sitosterol (ART5), -sitosterol glucopyranoside (ART24) and stigmast-4-en-3-one (ART37), three ellagic acid derivatives: 3,3',4-tri-O-methylellagic acid (ART10), 4-O-[-D-glucopyranosyl- tetraacetate]-3,3',4'-tri-O-methylellagic acid (ART28) and 3-O-methyl- ellagic acid 4-O-- rhamnopyranoside (ART41), two flavellagic acid derivatives: 3',4'-dioxymethylene- viii 3,4-di-O-methyl-flavellagic acid (ART25) and 3,4,3',4'-tetra-O-methylflavellagic acid (ART31), six benzenoids: -tocopherol (ART1), trans-triacontyl-4-hydroxy-3- methoxycinnamate (AR21), trans-triacontyl-4-hydroxy-cinnamate (ART30), 4-hydroxy- 3-methoxy-benzoic acid (ART35), gallic acid (ART36) and methyl gallate (ART40), one lignan: 9,9'-O-diferuloyl-(-)-secoisolariciresinol (ART33), one butyrolactone derivative: (3aS*,6aR*)-3a-(hydroxymethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3] dioxol-4(3aH)-one (ART15) and three sugars: -D-glucopyranoside penta-acetate (ART26), -D-glucopyranoside penta-acetate (ART27) and sucrose octa-acetate (ART29). Eleven compounds: ART2, ART3, ART4, ART9, ART11, ART15, ART18, ART19, ART20, ART31 and ART38 were newly found compounds. Their structures were elucidated on the basis of spectroscopic analyses including UV, IR, NMR, MS and by comparison of their spectroscopic data with those reported in the literature. Some of the isolated acylphloroglucinol compounds (ART2, ART4, ART6, ART9, ART11, ART18, ART19 and ART20) were also evaluated for their antibacterial activity against three types of Gram-positive bacteria, S. aureus, MRSA and Streptococcus pyogenes DMST 101. It was found that rhodomyrtone (ART6) and rhodomyrtosone B (ART9) showed good activity to inhibit the growth of S. aureus, MRSA and S. pyogenes with MIC values of 0.39, 6.25 g/mL, 0.39, 12.5 g/mL, and 0.39, 3.125 g/mL, respectively. In addition, rhodomyrtosone G (ART19) inhibited the growth of both S. aureus and MRSA with the MIC value of 1.56g/mL while rhodomyrtosone D (ART11) further showed the inhibitory activity against S. pyogenes with the MIC value of 12.5g/mL. Interestingly, rhodomyrtone (ART6) exhibited the activity more than the standard,
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