Cancer chemopreventive agents from Bruguiera gymnorrhiza ‪(L.)‬ Savigny flowers

สารป้องกันมะเร็งจากพังกาหัวสุมดอกแดง

Name: Sudarat Homhual

LCSH: Bruguiera gymnorrhiza

MeSH: Antineoplastic Agents, Phytogenic

MeSH: Luciferases

MeSH: Prostaglandin-Endoperoxide Synthase

Abstract: Studies on cancer chemopreventive activities were carried out on the flowers of Bruguiera gymnorrhiza (L.) Savigny. The powdered flowers were successively extracted with petroleum ether, chloroform, ethyl acetate and methanol. These extracts were tested for cancer chemopreventive activity including inhibition of cyclooxygenase (COX) both in COX-1 and COX-2, luciferase activity by activation of antioxidant-reponse element (ARE) and inhibition of nuclear factor kappa B (NF
B). Crude chloroform extract was shown to inhibit COX-1 with IC50 value of 2.98 μg/ml. All extracts were found to be inactive in COX-2 inhibition. Petroleum ether and ethyl acetate extracts exhibited activation of ARE with EC50 values of 0.71 and 12.9 μg/ml, respectively. Chloroform and methanol extracts were inactive. Three extracts of petroleum ether, chloroform and ethyl acetate demonstrated inhibition of NF
B with IC50 values of 19.7, 0.03 and 1.85 μg/ml, respectively. Because of their biological activities, chloroform and petroleum ether extracts were submitted for further separation. The petroleum ether extract was separated using column chromatography to afford six compounds of K1, K2, K8, K10, K11 and K12. The structures of compounds K2, K1 and K8 were determined on the basis of physical and spectroscopic data to be novel dammarane triterpenoids; 1,20(S)-dihydroxydammar-24(25)-ene-3
-O-stearate, 11,20(S)- dihydroxydammar-24(25)-ene-3
-O-stearate and 1
,20(S)-dihydroxy-25-hydroperoxydammar -23(24)-ene-3
-O-stearate, and given the trivial names, bruguierin A, bruguierin B and bruguierin C, respectively. Compounds K10, K11 and K12 have been identified as taraxerone, nonacosane and heptacosane, respectively. The investigation of chloroform extract has led to six compounds: K3, K7, K9, K4, K5 and K6. The structure elucidation indicated that compounds K3, K7 and K9 were cyclic 4-hydroxy-dithiosulfonate. Compound K3 was assigned to be 1,1-dioxo-16-[1,2]dithiolan-4-ol, a novel cyclic dithiosulfonate and given the trivial name, bruguiesulfurol. Compounds K7, K9, K5, K4 and K6 were identified by comparing them with previous reports as brugierol, isobrugierol, triacontanol, daucosterol and daucosterol 6-O-palmitate, respectively. Compounds K2 and K7 demonstrated inhibition of COX-2 with IC50 values of 6.6 and 6.1 μM, respectively. Compounds K2, K7 and K9 were found to inhibit NF
B with IC50 values of 7.8, 85.0 and 14.5 μM, respectively. Compounds K1, K2, K3, K7, K8 and K9 exhibited activation of ARE with EC50 values of 13.3, 9.5, 56.7, 3.5, 17.9 and 1.8 μM, respectively. Compounds K7, K9 and K10 also showed the inhibition of TPA-induced ornithine decarboxylase (ODC) activity and induction of quinone reductase (QR) activity. Compounds K9 and K10 inhibited ODC, with an IC50 values of 43.5, 47.2 μM, respectively whereas K10 exhibited induction of QR with induction ratio (IR) 1.1

Mahidol University

Address: NAKHON PATHOM

Email: liwww@mahidol.ac.th

Name: Nuntavan Bunyapraphatsara

Role: Thesis Advisors

Created: 2006

Modified: 2553-06-15

Issued: 2010-06-01

วิทยานิพนธ์/Thesis

application/pdf

ISBN: 9740471161

CallNumber: TH S943ca 2006

eng

DegreeName: Doctor of Philosophy

Level: Doctoral Degree

Descipline: Pharmaceutical Chemistry and Phytochemistry

Grantor: Mahidol University

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