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Phytochemical and Biological Activity Studies of Hedyotis Herbacea, Hedyotis Diffusa and Roots of Garcinia Atroviridis

A new anthraquinone, 2-hydroxymethyl-10-hydroxy-1, 4-anthraquinone (9) was isolated from the dried aerial part of Hedyotis herbacea (Rubiaceae) together with five other known compounds, 1,4-dihydroxy-2-hydroxymethylantbraquinone (10), 2,3-dimethoxy-9-hydroxy-l,4-anthraquinone (11), 1,4-dihydroxy-2,3...

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Main Author: Permana, Dharma
Format: Thesis
Language:English
Published: 2002
Online Access:http://ethesis.upm.edu.my/id/eprint/3230/1/FSAS_2002_18_F.pdf
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spelling oai:ethesis.upm.edu.my:3230 http://ethesis.upm.edu.my/id/eprint/3230/ Phytochemical and Biological Activity Studies of Hedyotis Herbacea, Hedyotis Diffusa and Roots of Garcinia Atroviridis Permana, Dharma A new anthraquinone, 2-hydroxymethyl-10-hydroxy-1, 4-anthraquinone (9) was isolated from the dried aerial part of Hedyotis herbacea (Rubiaceae) together with five other known compounds, 1,4-dihydroxy-2-hydroxymethylantbraquinone (10), 2,3-dimethoxy-9-hydroxy-l,4-anthraquinone (11), 1,4-dihydroxy-2,3- dimethoxylanthraquinone (12), kaempferol 3-0-rutinose (13) and arbutin (14). Extraction and isolation of the constituents from Hedyotis diffusa has yielded three compounds, quercetin 3-0-glucose (15), quercetin 3-0-rutinose (16) and asperuloside (17). Three new prenylated compounds, the depsidone atrovirisidone (24), the benzoquinone atrovirinone (25) and the hydro quinone 4-methyldihydroatrovirinone (26), along with three known compounds, 14-cis-docosenoic acid (27), morelloflavone (28) and fukugiside (29) have been isolated from the ethyl acetate fraction of the methanol crude extract of the dried roots of Garcinia atroviridis. In the biological activity assay, quercetin 3-0-glucose (15), quercetin 3-0- rutinose (16), atrovirisidone (24), morelloflavone (28) and fukugiside (29) were found to have stronger antioxidant activity than vitamin E. 2-hydroxymethyl-lOhydroxy- l,4-anthraquinone (9) and quercetin 3-0-rutinose (16) showed strong toxic activity in the brine shrimp lethality assay with a 50 % lethal concentration of 9.7 µg/mL and 23. 4 µg/mL, respectively. Atrovirisidone (24) and atrovirinone (25) were very effective against the microbe Bacillus subtilis (mutant type) and Bacillus subtilis (wild type) (MID 10 Ilg/disc for both). Quercetin 3-0-glucose (15), quercetin 3-0-rutinose (16), 4-methyl-dihydroatrovirinone (26), morelloflavone (28) and fukugiside (29) showed weak activity compared to atrovirisidone (24) and atrovirinone (25) but it is still significantly active (MID 100 µg/disc for all compounds). Only atrovirisidone (24) exhibited cytotoxic activity towards HeLa cells at IC₅₀ 15 µg/mL that was comparable to the standards doxorubicin (IC₅₀ 11 µg/mL) and colchicine (IC₅₀ 21 µg/mL). 2002-01 Thesis NonPeerReviewed application/pdf en http://ethesis.upm.edu.my/id/eprint/3230/1/FSAS_2002_18_F.pdf Permana, Dharma (2002) Phytochemical and Biological Activity Studies of Hedyotis Herbacea, Hedyotis Diffusa and Roots of Garcinia Atroviridis. PhD thesis, Universiti Putra Malaysia. (FSAS 2002 18).
institution UPM eTHESES
collection UPM eTHESES
language English
description A new anthraquinone, 2-hydroxymethyl-10-hydroxy-1, 4-anthraquinone (9) was isolated from the dried aerial part of Hedyotis herbacea (Rubiaceae) together with five other known compounds, 1,4-dihydroxy-2-hydroxymethylantbraquinone (10), 2,3-dimethoxy-9-hydroxy-l,4-anthraquinone (11), 1,4-dihydroxy-2,3- dimethoxylanthraquinone (12), kaempferol 3-0-rutinose (13) and arbutin (14). Extraction and isolation of the constituents from Hedyotis diffusa has yielded three compounds, quercetin 3-0-glucose (15), quercetin 3-0-rutinose (16) and asperuloside (17). Three new prenylated compounds, the depsidone atrovirisidone (24), the benzoquinone atrovirinone (25) and the hydro quinone 4-methyldihydroatrovirinone (26), along with three known compounds, 14-cis-docosenoic acid (27), morelloflavone (28) and fukugiside (29) have been isolated from the ethyl acetate fraction of the methanol crude extract of the dried roots of Garcinia atroviridis. In the biological activity assay, quercetin 3-0-glucose (15), quercetin 3-0- rutinose (16), atrovirisidone (24), morelloflavone (28) and fukugiside (29) were found to have stronger antioxidant activity than vitamin E. 2-hydroxymethyl-lOhydroxy- l,4-anthraquinone (9) and quercetin 3-0-rutinose (16) showed strong toxic activity in the brine shrimp lethality assay with a 50 % lethal concentration of 9.7 µg/mL and 23. 4 µg/mL, respectively. Atrovirisidone (24) and atrovirinone (25) were very effective against the microbe Bacillus subtilis (mutant type) and Bacillus subtilis (wild type) (MID 10 Ilg/disc for both). Quercetin 3-0-glucose (15), quercetin 3-0-rutinose (16), 4-methyl-dihydroatrovirinone (26), morelloflavone (28) and fukugiside (29) showed weak activity compared to atrovirisidone (24) and atrovirinone (25) but it is still significantly active (MID 100 µg/disc for all compounds). Only atrovirisidone (24) exhibited cytotoxic activity towards HeLa cells at IC₅₀ 15 µg/mL that was comparable to the standards doxorubicin (IC₅₀ 11 µg/mL) and colchicine (IC₅₀ 21 µg/mL).
format Thesis
author Permana, Dharma
spellingShingle Permana, Dharma
Phytochemical and Biological Activity Studies of Hedyotis Herbacea, Hedyotis Diffusa and Roots of Garcinia Atroviridis
author_facet Permana, Dharma
author_sort Permana, Dharma
title Phytochemical and Biological Activity Studies of Hedyotis Herbacea, Hedyotis Diffusa and Roots of Garcinia Atroviridis
title_short Phytochemical and Biological Activity Studies of Hedyotis Herbacea, Hedyotis Diffusa and Roots of Garcinia Atroviridis
title_full Phytochemical and Biological Activity Studies of Hedyotis Herbacea, Hedyotis Diffusa and Roots of Garcinia Atroviridis
title_fullStr Phytochemical and Biological Activity Studies of Hedyotis Herbacea, Hedyotis Diffusa and Roots of Garcinia Atroviridis
title_full_unstemmed Phytochemical and Biological Activity Studies of Hedyotis Herbacea, Hedyotis Diffusa and Roots of Garcinia Atroviridis
title_sort phytochemical and biological activity studies of hedyotis herbacea, hedyotis diffusa and roots of garcinia atroviridis
publishDate 2002
url http://ethesis.upm.edu.my/id/eprint/3230/1/FSAS_2002_18_F.pdf
_version_ 1819310346300555264
score 13.4562235

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