Chemical Composition, Antioxidant and Cytotoxicity Activities of Leaves, Bark, Twigs and Oleo-Resin of Dipterocarpus alatus
Abstract
:1. Introduction
2. Results and Discussion
2.1. Extraction and Phytochemical Analysis
2.2. Chemical Constituents of D. alatus Extracts
2.3. Cytotoxic Activity
2.4. Antioxidant Activities and Total Phenolic Contents
3. Materials and Methods
3.1. Plant Materials
3.2. Sample Preparation
3.3. Phytochemical Test
3.4. Antioxidant Activity
3.4.1. DPPH Radical Scavenging
3.4.2. ABTS Radical Scavenging
3.4.3. Ferric Reducing Antioxidant Power (FRAP)
3.4.4. Total Phenolic Content (TPC)
3.5. Cell Culture
3.6. Cytotoxic Activity
3.7. Gas Chromatography–Mass Spectrometry (GC-MS) Analysis
3.8. Statistical Analysis
4. Conclusion
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of Dipterocarpus alatus extracts are available from the authors. |
Part of Plant | Chemical Group | ||||
---|---|---|---|---|---|
Alkaloid | Steroid | Tannin | Xanthone | Reducing Sugar | |
Leaves | − | − | + | − | + |
Bark | + | + | + | + | + |
Twigs | − | + | + | − | + |
Oleo-resin | − | + | − | − | − |
Compound | Retention Time | Compound Name | Molecular Weight | Molecular Formula | % (Peak area) | Fragmentation Pattern m/z (Decreasing Order of Abundance) |
---|---|---|---|---|---|---|
1 | 23.48 | δ-Elemene | 204 | C15H24 | 0.08 | 121(100), 93, 136, 107, 79, 41, 161, 55, 67, 189, 204 |
2 | 24.05 | α-Cubebene | 204 | C15H24 | 0.03 | 105(100), 119, 161, 91, 81, 41, 55, 204, 133 |
3 | 25.25 | α-Copeane | 204 | C15H24 | 0.35 | 119(100), 105, 161, 93, 81, 41, 55, 133, 204, 65 |
4 | 25.98 | β-Elemene | 204 | C15H24 | 0.78 | 93(100), 81, 68, 107, 41, 55, 121, 147, 133, 161, 189, 175, 204 |
5 | 26.87 | α-Gurjunene | 204 | C15H24 | 30.31 | 105(100), 119, 161, 204, 189, 91, 133, 41, 147, 81, 55, 67 |
6 | 27.10 | β-Caryophyllene | 204 | C15H24 | 3.14 | 93(100), 69, 41, 133, 105, 79, 55, 119, 147, 161, 189, 175, 204 |
7 | 27.63 | (−)-Isoledene | 204 | C15H24 | 13.69 | 161(100), 105, 119, 91, 41, 133, 189, 147, 69, 69, 55, 204 |
8 | 28.26 | α-Humulene | 204 | C15H24 | 0.94 | 93(100), 80, 121, 41, 147, 107, 67, 55, 204, 136 |
9 | 28.55 | Alloaromadendrene | 204 | C15H24 | 3.28 | 91(100), 41, 105, 161, 133, 79, 119, 65, 55, 147, 204, 189 |
10 | 28.94 | γ-Gurjunene | 204 | C15H24 | 3.14 | 107(100), 81, 161, 91, 121, 41, 55, 133, 67, 189, 147, 204, 175 |
11 | 29.65 | Viridiflorene | 204 | C15H24 | 0.61 | 107(100), 93, 41, 119, 81, 133, 55, 161, 189, 67, 147, 204, 175 |
12 | 29.96 | β-Vatirenene | 202 | C15H22 | 0.12 | 145(100), 105, 131, 91, 202, 120, 159, 187, 41, 77, 55, 67, 173 |
13 | 30.37 | Selina-3,7(11)-diene | 204 | C15H24 | 0.52 | 122(100), 161, 107, 91, 81, 41, 55, 67, 133, 204, 189, 147 |
14 | 31.65 | Calarene epoxide | 220 | C15H24O | 0.04 | 41(100), 65, 93, 109, 119, 82, 135, 161, 185, 145, 177, 205, 220 |
15 | 31.85 | Palustrol | 222 | C15H26O | 0.13 | 122(100), 111, 81, 93, 41, 67, 161, 147, 189, 204, 133, 175, 222 |
16 | 32.17 | Spathulenol | 220 | C15H24O | 1.11 | 43(100), 91, 119, 41, 105, 205, 79, 159, 69, 131, 147, 187, 177, 220 |
17 | 32.30 | (−)-Caryophyllene oxide | 220 | C15H24O | 0.75 | 41(100), 79, 93, 69, 109, 121, 131, 161, 187, 177 202, 220 |
18 | 33.88 | α-Cadinol | 222 | C15H26O | 0.08 | 95(100), 43, 121, 161, 109, 204, 71, 58, 41, 179, 222 |
19 | 61.78 | Otochilone | 424 | C30H48O | 0.17 | 409(100), 65, 109, 257, 95, 55, 41, 311, 81, 149, 119, 271, 245, 297, 231, 173, 161, 204, 187, 424 |
20 | 62.68 | Lupenone | 424 | C30H48O | 0.38 | 95(100), 109, 205, 81, 55, 121, 69, 135, 149, 189, 41, 161, 175, 424, 128, 313, 245, 355 |
Samples | IC50 (µg/mL) | |||||
---|---|---|---|---|---|---|
Vero | HCT116 | SK-LU-1 | SK-MEL-2 | SiHa | U937 | |
Leaves | >500 c | >500 d | >500 d | >500 c | >500 d | 91.3 ± 6.2 b |
Bark | >500 c | >500 d | 273.0 ± 18.3 b | >500 c | 197.8 ± 15.5 c | 106.1 ± 7.8 c |
Twigs | >500 c | 440.6 ± 28.7 c | > 500 d | >500 c | >500 d | 128.9 ± 2.5 d |
Oleo-resin | 88.7 ± 4.1 a | 340.3 ± 21.1 b | 336.6 ± 6.7 c | 215.2 ± 10.9 b | 59.6 ± 1.7 b | 63.3 ± 2.1 a |
Melphalan | 215.6 ± 3.7 b | 179.6 ± 12.2 a | 56.9 ± 0.3 a | 20.2 ± 2.1 a | 27.1 ± 0.8 a | 228.4 ± 8.8 e |
Samples | Selective Index (SI) * | ||||
---|---|---|---|---|---|
HCT116 | SK-LU-1 | SK-MEL-2 | SiHa | U937 | |
Leaves | 1.0 | 1.0 | 1.0 | 1.0 | >5.5 |
Bark | 1.0 | >1.8 | 1.0 | >2.5 | >4.7 |
Twigs | >1.1 | 1.0 | 1.0 | 1.0 | >3.9 |
Oleo-resin | 0.3 | 0.3 | 0.4 | 1.5 | 1.4 |
Melphalan | 1.2 | 3.8 | 10.7 | 8.0 | 0.9 |
Samples | Antioxidant Capacity | Total Phenolic Content (mg GAE/g DW) | ||
---|---|---|---|---|
DPPH IC50 (µg/mL) | ABTS IC50 (µg/mL) | FRAP (mmole/100 g DW) | ||
Leaves | 26.76 ± 0.25 d | 13.56 ± 0.09 c | 124.80 ± 0.19 c | 308.60 ± 4.32 b |
Bark | 5.76 ± 0.19 b | 9.37 ± 0.03 a | 300.67 ± 2.93 b | 366.43 ± 11.52 a |
Twigs | 16.53 ± 0.61 c | 15.46 ± 0.02 d | 102.79 ± 1.01 d | 128.29 ± 3.89 c |
Oleo-resin | >1000 e | >1000 e | 21.02 ± 0.19 e | 15.14 ± 0.62 d |
Trolox | 3.93 ± 0.02 a | 10.20 ± 0.10 b | 771.70 ± 11.37 a | - |
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Yongram, C.; Sungthong, B.; Puthongking, P.; Weerapreeyakul, N. Chemical Composition, Antioxidant and Cytotoxicity Activities of Leaves, Bark, Twigs and Oleo-Resin of Dipterocarpus alatus. Molecules 2019, 24, 3083. https://doi.org/10.3390/molecules24173083
Yongram C, Sungthong B, Puthongking P, Weerapreeyakul N. Chemical Composition, Antioxidant and Cytotoxicity Activities of Leaves, Bark, Twigs and Oleo-Resin of Dipterocarpus alatus. Molecules. 2019; 24(17):3083. https://doi.org/10.3390/molecules24173083
Chicago/Turabian StyleYongram, Chawalit, Bunleu Sungthong, Ploenthip Puthongking, and Natthida Weerapreeyakul. 2019. "Chemical Composition, Antioxidant and Cytotoxicity Activities of Leaves, Bark, Twigs and Oleo-Resin of Dipterocarpus alatus" Molecules 24, no. 17: 3083. https://doi.org/10.3390/molecules24173083