Isolation of Kaempferia angustifolia rosc., Alpinia conchigera griff. and Curcuma mangga val. and Van zijp. phytochemicals and their bioactivities

Zingiberaceae is one of the most important herbaceous families found in tropical forests. In this research, Kaempferia angustifolia Rosc. (Kunci pepet), Alpinia conchigera Griff. (lengkuas ranting) and Curcuma mangga Val. & Van Zijp. (mango turmeric) were selected for phytochemical and bio-activ...

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Main Author:	Tang, Sook Wah
Format:	Thesis
Language:	English English
Published:	2011
Subjects:	Zingiberaceae Alpinia Curcuma
Online Access:	http://psasir.upm.edu.my/id/eprint/26770/1/FS%202011%2084R.pdf
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id	my-upm-ir.26770
record_format	uketd_dc
institution	Universiti Putra Malaysia
collection	PSAS Institutional Repository
language	English English
topic	Zingiberaceae Alpinia Curcuma
spellingShingle	Zingiberaceae Alpinia Curcuma Tang, Sook Wah Isolation of Kaempferia angustifolia rosc., Alpinia conchigera griff. and Curcuma mangga val. and Van zijp. phytochemicals and their bioactivities
description	Zingiberaceae is one of the most important herbaceous families found in tropical forests. In this research, Kaempferia angustifolia Rosc. (Kunci pepet), Alpinia conchigera Griff. (lengkuas ranting) and Curcuma mangga Val. & Van Zijp. (mango turmeric) were selected for phytochemical and bio-activity studies. Several classes of chemical constituents have been isolated and characterized spectroscopically. This included cyclohexane epoxides, chalcones, terpenes, phenylpropanoids and diarylheptanoids. From Kaempferia angustifolia, crotepoxide (29), boesenboxide (30), 2'-hydroxy-4,4',6'-trimethoxychalcone (31), zeylenol (28), 6-methylzeylenol (32), abiet-8(14)- enepenta-6,7,9,11,13-ol (kaempfolienol) (84), (24S)-24-methyl-lanosta-9(11),25-dien-3β-ol (80), pipoxide (25) were isolated besides β-sitosterol (82) and its glycoside (83). Similarly, β-sitosterol-3-O-β-D-glucopyranoside (83) was also obtained from the rhizomes of Alpinia conchigera along with p hydroxycinnamaldehyde (55), 1’-acetoxychavicol acetate (33) and trans-p-coumaryl diacetate (53). Furthermore, β-sitosterol (82), curcumin (59), demethoxycurcumin (60) and 12,17-epoxy-3β,17-dihydroxylabda-13-en-16,15-olide (curcumangganol)(94) were yielded from the Curcuma mangga extract. The structure of zeylenol (28)was modified by using chemical reactions to give zeylenol diacetate (89), zeylenol triacetate (90) and zeylenol epoxide (91) derivatives. p-Hydroxycinnamaldehyde (55)was also derivatized to p-methoxycinnamaldehyde (92) and pacetoxycinnamaldehyde (93). 5S,6S,7S,9S,10S,11R,13S-Abiet-8(14)-enepenta-6,7,9,11,13-ol (Kaempfolienol) (84)and epimeric 12,17-epoxy-3β,17-dihydroxylabda-13-en-16,15-olide (curcumangganol I and II) (94) were isolated as new compounds. The stereostructure of compound 84 was determined on the basis of its single crystal X-ray crystallography. Compounds 80, 83 and (+)-25 were firstly described from the respective species. Structures of all the isolated phytochemicals and structurallymodified compounds were elucidated by using various spectroscopic methods [infrared (IR), mass spectrometry (MS) and nuclear magnetic resonance (NMR)] and by comparison with the previous literature. Crude extracts, isolated constituents and derivatives were subjected to cytotoxic screening against four cancer cell lines (HL-60, HT-29, MCF-7 and HeLa) as well as antimicrobial testing. Crude extracts of Kaempferia angustifolia were not active in the cytotoxic assays, with IC50 values more than 30 μg/mL. Isolated phytochemicals from this species exhibited different degrees of inhibitions against the cancer cell lines tested, with 2’-hydroxy-4,4’,6’-trimethoxychalcone (31) and (24S)-24-methyl lanosta-9(11),25-dien-3β-ol (80) demonstrating the most prominent cytotoxic activities (IC50 < 8 μg/mL) against certain cell lines. As for Alpinia conchigera, nonpolar and semi-polar extracts showed strong cytotoxic properties against human promyelocytic leukaemia (HL-60), human breast cancer (MCF-7) and human cervical cancer (HeLa) cell lines. 1’-Acetoxychavicol acetate (33) and phydroxycinnamaldehyde (55) displayed a broad spectrum of anticancer effects against the tested cell lines. In addition, the chloroform extract of Curcuma mangga and isolated compounds 59, 60 and 94 also exhibited potent cytotoxic activities in the study. In antimicrobial screening test, extracts and constituents of Kaempferia angustifolia were not active. On the other hand, the crude hexane, chloroform and ethyl acetate extracts of Alpinia conchigera were strongly active against Salmonella choleraesuis in the antimicrobial assay. In antifungal screening test, hexane and ethyl acetate extracts of Alpinia conchigera showed slight inhibition on Saccharomyces cerevisiae. 4- Hydroxycinnamaldehyde (55) showed a remarkable activity in the antimicrobialtesting with a diameter of inhibition zone > 20 mm. The chloroform-soluble fraction of Curcuma mangga and demethoxycurcumin (60) showed negative results in the antimicrobial and antifungal screenings but curcumangganol (94) from the extract demonstrated a moderate inhibitory activity towards Bacillus subtilis (B29).
format	Thesis
qualification_level	Doctorate
author	Tang, Sook Wah
author_facet	Tang, Sook Wah
author_sort	Tang, Sook Wah
title	Isolation of Kaempferia angustifolia rosc., Alpinia conchigera griff. and Curcuma mangga val. and Van zijp. phytochemicals and their bioactivities
title_short	Isolation of Kaempferia angustifolia rosc., Alpinia conchigera griff. and Curcuma mangga val. and Van zijp. phytochemicals and their bioactivities
title_full	Isolation of Kaempferia angustifolia rosc., Alpinia conchigera griff. and Curcuma mangga val. and Van zijp. phytochemicals and their bioactivities
title_fullStr	Isolation of Kaempferia angustifolia rosc., Alpinia conchigera griff. and Curcuma mangga val. and Van zijp. phytochemicals and their bioactivities
title_full_unstemmed	Isolation of Kaempferia angustifolia rosc., Alpinia conchigera griff. and Curcuma mangga val. and Van zijp. phytochemicals and their bioactivities
title_sort	isolation of kaempferia angustifolia rosc., alpinia conchigera griff. and curcuma mangga val. and van zijp. phytochemicals and their bioactivities
granting_institution	Universiti Putra Malaysia
granting_department	Faculty of Science
publishDate	2011
url	http://psasir.upm.edu.my/id/eprint/26770/1/FS%202011%2084R.pdf
_version_	1747811559994818560
spelling	my-upm-ir.267702022-01-26T05:35:34Z Isolation of Kaempferia angustifolia rosc., Alpinia conchigera griff. and Curcuma mangga val. and Van zijp. phytochemicals and their bioactivities 2011-04 Tang, Sook Wah Zingiberaceae is one of the most important herbaceous families found in tropical forests. In this research, Kaempferia angustifolia Rosc. (Kunci pepet), Alpinia conchigera Griff. (lengkuas ranting) and Curcuma mangga Val. & Van Zijp. (mango turmeric) were selected for phytochemical and bio-activity studies. Several classes of chemical constituents have been isolated and characterized spectroscopically. This included cyclohexane epoxides, chalcones, terpenes, phenylpropanoids and diarylheptanoids. From Kaempferia angustifolia, crotepoxide (29), boesenboxide (30), 2'-hydroxy-4,4',6'-trimethoxychalcone (31), zeylenol (28), 6-methylzeylenol (32), abiet-8(14)- enepenta-6,7,9,11,13-ol (kaempfolienol) (84), (24S)-24-methyl-lanosta-9(11),25-dien-3β-ol (80), pipoxide (25) were isolated besides β-sitosterol (82) and its glycoside (83). Similarly, β-sitosterol-3-O-β-D-glucopyranoside (83) was also obtained from the rhizomes of Alpinia conchigera along with p hydroxycinnamaldehyde (55), 1’-acetoxychavicol acetate (33) and trans-p-coumaryl diacetate (53). Furthermore, β-sitosterol (82), curcumin (59), demethoxycurcumin (60) and 12,17-epoxy-3β,17-dihydroxylabda-13-en-16,15-olide (curcumangganol)(94) were yielded from the Curcuma mangga extract. The structure of zeylenol (28)was modified by using chemical reactions to give zeylenol diacetate (89), zeylenol triacetate (90) and zeylenol epoxide (91) derivatives. p-Hydroxycinnamaldehyde (55)was also derivatized to p-methoxycinnamaldehyde (92) and pacetoxycinnamaldehyde (93). 5S,6S,7S,9S,10S,11R,13S-Abiet-8(14)-enepenta-6,7,9,11,13-ol (Kaempfolienol) (84)and epimeric 12,17-epoxy-3β,17-dihydroxylabda-13-en-16,15-olide (curcumangganol I and II) (94) were isolated as new compounds. The stereostructure of compound 84 was determined on the basis of its single crystal X-ray crystallography. Compounds 80, 83 and (+)-25 were firstly described from the respective species. Structures of all the isolated phytochemicals and structurallymodified compounds were elucidated by using various spectroscopic methods [infrared (IR), mass spectrometry (MS) and nuclear magnetic resonance (NMR)] and by comparison with the previous literature. Crude extracts, isolated constituents and derivatives were subjected to cytotoxic screening against four cancer cell lines (HL-60, HT-29, MCF-7 and HeLa) as well as antimicrobial testing. Crude extracts of Kaempferia angustifolia were not active in the cytotoxic assays, with IC50 values more than 30 μg/mL. Isolated phytochemicals from this species exhibited different degrees of inhibitions against the cancer cell lines tested, with 2’-hydroxy-4,4’,6’-trimethoxychalcone (31) and (24S)-24-methyl lanosta-9(11),25-dien-3β-ol (80) demonstrating the most prominent cytotoxic activities (IC50 < 8 μg/mL) against certain cell lines. As for Alpinia conchigera, nonpolar and semi-polar extracts showed strong cytotoxic properties against human promyelocytic leukaemia (HL-60), human breast cancer (MCF-7) and human cervical cancer (HeLa) cell lines. 1’-Acetoxychavicol acetate (33) and phydroxycinnamaldehyde (55) displayed a broad spectrum of anticancer effects against the tested cell lines. In addition, the chloroform extract of Curcuma mangga and isolated compounds 59, 60 and 94 also exhibited potent cytotoxic activities in the study. In antimicrobial screening test, extracts and constituents of Kaempferia angustifolia were not active. On the other hand, the crude hexane, chloroform and ethyl acetate extracts of Alpinia conchigera were strongly active against Salmonella choleraesuis in the antimicrobial assay. In antifungal screening test, hexane and ethyl acetate extracts of Alpinia conchigera showed slight inhibition on Saccharomyces cerevisiae. 4- Hydroxycinnamaldehyde (55) showed a remarkable activity in the antimicrobialtesting with a diameter of inhibition zone > 20 mm. The chloroform-soluble fraction of Curcuma mangga and demethoxycurcumin (60) showed negative results in the antimicrobial and antifungal screenings but curcumangganol (94) from the extract demonstrated a moderate inhibitory activity towards Bacillus subtilis (B29). Zingiberaceae Alpinia Curcuma 2011-04 Thesis http://psasir.upm.edu.my/id/eprint/26770/ http://psasir.upm.edu.my/id/eprint/26770/1/FS%202011%2084R.pdf application/pdf en public doctoral Universiti Putra Malaysia Zingiberaceae Alpinia Curcuma Faculty of Science English

Isolation of Kaempferia angustifolia rosc., Alpinia conchigera griff. and Curcuma mangga val. and Van zijp. phytochemicals and their bioactivities

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