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Phytoconstituents from Alpinia purpurata and their in vitro inhibitory activity against Mycobacterium tuberculosis.

Villaflores OB, Macabeo AP, Gehle D, Krohn K, Franzblau SG, Aguinaldo AM - Pharmacogn Mag (2010)

Bottom Line: Alpinia purpurata or red ginger was studied for its phytochemical constituents as part of our growing interest on Philippine Zingiberaceae plants that may exhibit antimycobacterial activity.The two latter metabolites were spectroscopically identified as kumatakenin (1), sitosteryl-3-O-6-palmitoyl-β-D-glucoside (2) and b-sitosteryl galactoside (3) using ultraviolet (UV), infrared (IR), electron impact mass spectrometer (EIMS) and nuclear magnetic resonance (NMR) experiments, and by comparison with literature data.This study demonstrates for the first time the isolation of these constituents from A. purpurata.

View Article: PubMed Central - PubMed

Affiliation: Phytochemistry Laboratory, Research Center for the Natural Sciences, Thomas Aquinas Research Complex, University of Santo Tomas, España, Manila 1008, Philippines.

ABSTRACT
Alpinia purpurata or red ginger was studied for its phytochemical constituents as part of our growing interest on Philippine Zingiberaceae plants that may exhibit antimycobacterial activity. The hexane and dichloromethane subextracts of the leaves were fractionated and purified using silica gel chromatography to afford a mixture of C(28)-C(32) fatty alcohols, a 3-methoxyflavone and two steroidal glycosides. The two latter metabolites were spectroscopically identified as kumatakenin (1), sitosteryl-3-O-6-palmitoyl-β-D-glucoside (2) and b-sitosteryl galactoside (3) using ultraviolet (UV), infrared (IR), electron impact mass spectrometer (EIMS) and nuclear magnetic resonance (NMR) experiments, and by comparison with literature data. This study demonstrates for the first time the isolation of these constituents from A. purpurata. In addition to the purported anti-inflammatory activity, its phytomedicinal potential to treat tuberculosis is also described.

No MeSH data available.


Related in: MedlinePlus

Key 1H-13C HMBC Correlations in 2
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Figure 0003: Key 1H-13C HMBC Correlations in 2

Mentions: Compound 2 was obtained as a white amorphous solid (8.4 mg). Thin layer chromatograms of the isolate sprayed with Liebermann-burchard and Molisch reagents[12] suggested a steroidal glycoside structure. The IR spectrum showed the presence of hydroxyl (3439 cm-1) and ester (1738 cm-1) functionalities. The molecular ion peak was not observed in the LR-EIMS spectrum. Instead, fragment ions corresponding to sitosterol (m/z414, C29H50O) and a palmitoxy group (m/z256, C16H31O2) were noted. Signals characteristic of sitosterol resonances, i.e., C-6 olefinic proton (δ 5.36), methyls associated with the cholestane skeleton (δ 0.69–0.79), glucose (δ 4.34–4.38) and a palmitoyl group (δ 0.84, 1.26, 2.34) were evident in the 500-MHz 1H NMR of 2. A total of 51 carbon atoms, i.e., 7 CH3, 25 aliphatic CH2, 7 aliphatic CH, 2 aliphatic quaternary C, 1 oxygenated CH2, 6 oxygenated CH and one each olefinic CH and C, were found in the 125 MHz 13C NMR spectrum. HMBC correlations, which were instrumental in finding the correct identity of 2 as sitosteryl-3-O-6-palmitoyl-β-d-glucoside, are shown in Figure 3. The NMR values of 2 are well in agreement with those reported for sitosteryl-3-O-6-palmitoyl-β-d-glucoside by Pei-Wu et al.,[19] Gomes et al.,[20] and Shaiq Ali et al.[21]


Phytoconstituents from Alpinia purpurata and their in vitro inhibitory activity against Mycobacterium tuberculosis.

Villaflores OB, Macabeo AP, Gehle D, Krohn K, Franzblau SG, Aguinaldo AM - Pharmacogn Mag (2010)

Key 1H-13C HMBC Correlations in 2
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2992151&req=5

Figure 0003: Key 1H-13C HMBC Correlations in 2
Mentions: Compound 2 was obtained as a white amorphous solid (8.4 mg). Thin layer chromatograms of the isolate sprayed with Liebermann-burchard and Molisch reagents[12] suggested a steroidal glycoside structure. The IR spectrum showed the presence of hydroxyl (3439 cm-1) and ester (1738 cm-1) functionalities. The molecular ion peak was not observed in the LR-EIMS spectrum. Instead, fragment ions corresponding to sitosterol (m/z414, C29H50O) and a palmitoxy group (m/z256, C16H31O2) were noted. Signals characteristic of sitosterol resonances, i.e., C-6 olefinic proton (δ 5.36), methyls associated with the cholestane skeleton (δ 0.69–0.79), glucose (δ 4.34–4.38) and a palmitoyl group (δ 0.84, 1.26, 2.34) were evident in the 500-MHz 1H NMR of 2. A total of 51 carbon atoms, i.e., 7 CH3, 25 aliphatic CH2, 7 aliphatic CH, 2 aliphatic quaternary C, 1 oxygenated CH2, 6 oxygenated CH and one each olefinic CH and C, were found in the 125 MHz 13C NMR spectrum. HMBC correlations, which were instrumental in finding the correct identity of 2 as sitosteryl-3-O-6-palmitoyl-β-d-glucoside, are shown in Figure 3. The NMR values of 2 are well in agreement with those reported for sitosteryl-3-O-6-palmitoyl-β-d-glucoside by Pei-Wu et al.,[19] Gomes et al.,[20] and Shaiq Ali et al.[21]

Bottom Line: Alpinia purpurata or red ginger was studied for its phytochemical constituents as part of our growing interest on Philippine Zingiberaceae plants that may exhibit antimycobacterial activity.The two latter metabolites were spectroscopically identified as kumatakenin (1), sitosteryl-3-O-6-palmitoyl-β-D-glucoside (2) and b-sitosteryl galactoside (3) using ultraviolet (UV), infrared (IR), electron impact mass spectrometer (EIMS) and nuclear magnetic resonance (NMR) experiments, and by comparison with literature data.This study demonstrates for the first time the isolation of these constituents from A. purpurata.

View Article: PubMed Central - PubMed

Affiliation: Phytochemistry Laboratory, Research Center for the Natural Sciences, Thomas Aquinas Research Complex, University of Santo Tomas, España, Manila 1008, Philippines.

ABSTRACT
Alpinia purpurata or red ginger was studied for its phytochemical constituents as part of our growing interest on Philippine Zingiberaceae plants that may exhibit antimycobacterial activity. The hexane and dichloromethane subextracts of the leaves were fractionated and purified using silica gel chromatography to afford a mixture of C(28)-C(32) fatty alcohols, a 3-methoxyflavone and two steroidal glycosides. The two latter metabolites were spectroscopically identified as kumatakenin (1), sitosteryl-3-O-6-palmitoyl-β-D-glucoside (2) and b-sitosteryl galactoside (3) using ultraviolet (UV), infrared (IR), electron impact mass spectrometer (EIMS) and nuclear magnetic resonance (NMR) experiments, and by comparison with literature data. This study demonstrates for the first time the isolation of these constituents from A. purpurata. In addition to the purported anti-inflammatory activity, its phytomedicinal potential to treat tuberculosis is also described.

No MeSH data available.


Related in: MedlinePlus