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Phytochemical studies of Gnetum Microcarpum, Gnetum Cuspidatum, Cynometra Cauliflora, Bouea oppositifolia and their biological activities / Nik Fatini Nik Azmin

In the present work, phytochemical and pharmacological studies were conducted on four species of plants from three different families. The studied plant samples were the air-dried lianas of two species from Gnetaceae family which are Gnetum microcarpum Blume and Gnetum cuspidatum Blume and the twigs...

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Main Author: Nik Azmin, Nik Fatini
Format: Thesis
Language:English
Published: 2018
Online Access:https://ir.uitm.edu.my/id/eprint/38003/1/38003.pdf
https://ir.uitm.edu.my/id/eprint/38003/
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spelling my.uitm.ir.380032023-01-26T08:50:53Z https://ir.uitm.edu.my/id/eprint/38003/ Phytochemical studies of Gnetum Microcarpum, Gnetum Cuspidatum, Cynometra Cauliflora, Bouea oppositifolia and their biological activities / Nik Fatini Nik Azmin Nik Azmin, Nik Fatini In the present work, phytochemical and pharmacological studies were conducted on four species of plants from three different families. The studied plant samples were the air-dried lianas of two species from Gnetaceae family which are Gnetum microcarpum Blume and Gnetum cuspidatum Blume and the twigs of Cynometra cauliflora Linn from the family of Fabacaeae and Bouea oppositifolia (Roxb.) Meisn from the family of Anacardiaceae. The aims of this study are to isolate the secondary metabolites from the plants, to propose biogenetic pathway of the new isolated compounds, to determine their DPPH scavenging, PGE2 inhibitory and cytotoxic activities and to study the Structure-Activity Relationship (SAR). The isolation process was done by conventional method of maceration, fractionation, separation and purification using several chromatographic techniques and structural elucidation was based on the spectroscopic data evidences and comparison with reported authentic data. Phytochemicals investigation on the lianas of the two Gnetum species yielded 11 known stilbenoid compounds; resveratrol (1), isorhapontigenin (3), gnetol (10), gnetifolin P (18), gnetofuran C (20), gnetucleistol C (21), cuspidan B (24), e-viniferin (31), parvifolol D (44), gnemonol M (48) and malaysianol D (388), two new compounds from G. microcarpum characterized as malaysianol E (25), malaysianol F (389) and one new compound from G. cuspidatum, namely malaysianol G (399). Phytochemicals investigation on C. cauliflora and B. oppositifolia gave 16 known flavonoid compounds; naringenin (263) and eriodictyol (262) were obtained from both species; flavone apigenin, acacetin, luteolin, luteolin 3',5 dimethyl ether, 3',4',7- trihydroxyflavone, 4',7-dihydroxyflavone (392-397) and 5,7-dihydroxychromone (391) from C. cauliflora; chalcone isoliquiritigenin (398), flavanone liquiritigenin and butin (399-400), flavanol taxifolin (260), fustin, garbanzol (401-402) and aurone sulfuretin (403) from B. oppositifolia. Both flavonoids and stilbenoids were derived from the combination of shikimate pathway and acetate pathway from a cinnamoyl- CoA starter unit and three molecule of malonyl-CoA extender unit to form intermediate polyketide. The enzyme stilbene synthase (STS) gave resveratrol which then undergo polymerization to produce larger stilbenoid, while chalcone synthase (CS) gave chalcone which then act as precursor for a vast range of flavonoid derivatives. In the DPPH assay, gnemonol M (48) and fustin (260) displayed good scavenging activity with IC50 of 30.07 and 23.93 uM, respectively, higher than that of standard trolox (IC50 83.22 uM). In the PGE2 inhibition assay, gnemonol M (48) and 4',7-dihydroxyflavone (397) exhibited significant activity with IC50 of 1.15 and 3.39 uM, respectively, comparable to the standard, indomethacin (IC50 1.29 uM). For cytotoxicity, all the tested compounds were found to be, either moderate, weak or not cytotoxic against HCT116 cancer cell line. In the SAR study of DPPH scavenging, the number of hydroxyl groups and the presence of an electron donating group are essential for stilbenoids, while the catechol moeity is in the top priority to exert flavonoids activity. Meanwhile, both type of compounds required the substituents which will contribute to their hydrophobicity and balance number of hydroxyl group in their structure in order to exert better PGE2 inhibitory activity. 2018 Thesis NonPeerReviewed text en https://ir.uitm.edu.my/id/eprint/38003/1/38003.pdf Phytochemical studies of Gnetum Microcarpum, Gnetum Cuspidatum, Cynometra Cauliflora, Bouea oppositifolia and their biological activities / Nik Fatini Nik Azmin. (2018) PhD thesis, thesis, Universiti Teknologi MARA (UiTM).
institution Universiti Teknologi Mara
building Tun Abdul Razak Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Teknologi Mara
content_source UiTM Institutional Repository
url_provider http://ir.uitm.edu.my/
language English
description In the present work, phytochemical and pharmacological studies were conducted on four species of plants from three different families. The studied plant samples were the air-dried lianas of two species from Gnetaceae family which are Gnetum microcarpum Blume and Gnetum cuspidatum Blume and the twigs of Cynometra cauliflora Linn from the family of Fabacaeae and Bouea oppositifolia (Roxb.) Meisn from the family of Anacardiaceae. The aims of this study are to isolate the secondary metabolites from the plants, to propose biogenetic pathway of the new isolated compounds, to determine their DPPH scavenging, PGE2 inhibitory and cytotoxic activities and to study the Structure-Activity Relationship (SAR). The isolation process was done by conventional method of maceration, fractionation, separation and purification using several chromatographic techniques and structural elucidation was based on the spectroscopic data evidences and comparison with reported authentic data. Phytochemicals investigation on the lianas of the two Gnetum species yielded 11 known stilbenoid compounds; resveratrol (1), isorhapontigenin (3), gnetol (10), gnetifolin P (18), gnetofuran C (20), gnetucleistol C (21), cuspidan B (24), e-viniferin (31), parvifolol D (44), gnemonol M (48) and malaysianol D (388), two new compounds from G. microcarpum characterized as malaysianol E (25), malaysianol F (389) and one new compound from G. cuspidatum, namely malaysianol G (399). Phytochemicals investigation on C. cauliflora and B. oppositifolia gave 16 known flavonoid compounds; naringenin (263) and eriodictyol (262) were obtained from both species; flavone apigenin, acacetin, luteolin, luteolin 3',5 dimethyl ether, 3',4',7- trihydroxyflavone, 4',7-dihydroxyflavone (392-397) and 5,7-dihydroxychromone (391) from C. cauliflora; chalcone isoliquiritigenin (398), flavanone liquiritigenin and butin (399-400), flavanol taxifolin (260), fustin, garbanzol (401-402) and aurone sulfuretin (403) from B. oppositifolia. Both flavonoids and stilbenoids were derived from the combination of shikimate pathway and acetate pathway from a cinnamoyl- CoA starter unit and three molecule of malonyl-CoA extender unit to form intermediate polyketide. The enzyme stilbene synthase (STS) gave resveratrol which then undergo polymerization to produce larger stilbenoid, while chalcone synthase (CS) gave chalcone which then act as precursor for a vast range of flavonoid derivatives. In the DPPH assay, gnemonol M (48) and fustin (260) displayed good scavenging activity with IC50 of 30.07 and 23.93 uM, respectively, higher than that of standard trolox (IC50 83.22 uM). In the PGE2 inhibition assay, gnemonol M (48) and 4',7-dihydroxyflavone (397) exhibited significant activity with IC50 of 1.15 and 3.39 uM, respectively, comparable to the standard, indomethacin (IC50 1.29 uM). For cytotoxicity, all the tested compounds were found to be, either moderate, weak or not cytotoxic against HCT116 cancer cell line. In the SAR study of DPPH scavenging, the number of hydroxyl groups and the presence of an electron donating group are essential for stilbenoids, while the catechol moeity is in the top priority to exert flavonoids activity. Meanwhile, both type of compounds required the substituents which will contribute to their hydrophobicity and balance number of hydroxyl group in their structure in order to exert better PGE2 inhibitory activity.
format Thesis
author Nik Azmin, Nik Fatini
spellingShingle Nik Azmin, Nik Fatini
Phytochemical studies of Gnetum Microcarpum, Gnetum Cuspidatum, Cynometra Cauliflora, Bouea oppositifolia and their biological activities / Nik Fatini Nik Azmin
author_facet Nik Azmin, Nik Fatini
author_sort Nik Azmin, Nik Fatini
title Phytochemical studies of Gnetum Microcarpum, Gnetum Cuspidatum, Cynometra Cauliflora, Bouea oppositifolia and their biological activities / Nik Fatini Nik Azmin
title_short Phytochemical studies of Gnetum Microcarpum, Gnetum Cuspidatum, Cynometra Cauliflora, Bouea oppositifolia and their biological activities / Nik Fatini Nik Azmin
title_full Phytochemical studies of Gnetum Microcarpum, Gnetum Cuspidatum, Cynometra Cauliflora, Bouea oppositifolia and their biological activities / Nik Fatini Nik Azmin
title_fullStr Phytochemical studies of Gnetum Microcarpum, Gnetum Cuspidatum, Cynometra Cauliflora, Bouea oppositifolia and their biological activities / Nik Fatini Nik Azmin
title_full_unstemmed Phytochemical studies of Gnetum Microcarpum, Gnetum Cuspidatum, Cynometra Cauliflora, Bouea oppositifolia and their biological activities / Nik Fatini Nik Azmin
title_sort phytochemical studies of gnetum microcarpum, gnetum cuspidatum, cynometra cauliflora, bouea oppositifolia and their biological activities / nik fatini nik azmin
publishDate 2018
url https://ir.uitm.edu.my/id/eprint/38003/1/38003.pdf
https://ir.uitm.edu.my/id/eprint/38003/
_version_ 1756687547325480960
score 13.211869

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