Bio-Guided Isolation of Prospective Bioactive Constituents from Roots of Clausena indica (Dalzell) Oliv
Abstract
:1. Introduction
2. Results and Discussion
2.1. Isolation, Identification, and Confirmation of Bioactive Compounds from Clausena Indica Roots
2.2. Biological Activities of Clausena Indica
2.3. Dentatin, Nordentatin and Clausine K Contents in Clausena indica Roots’ Extract
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Materials
3.3. Sample Preparation, Extraction and Isolation
3.4. Biological Assays
3.4.1. Antioxidant Activities
3.4.2. α-Amylase Inhibitory Assay
3.4.3. Elastase and Tyrosinase Inhibitory Assay
3.5. Identification and Confirmation of Isolated Compounds and other Phytochemical Constituents
3.6. Quantification of Dentatin, Nordentatin and Clausine K contents by HPLC-UV/VIS
3.7. Statistical Analyses
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds dentatin, nordentatin, and clausine K are available from the authors. |
Dentatin | Nordentatin | Clausine K | ||||
---|---|---|---|---|---|---|
Chemical formula | C20H22O4 | C19H20O4 | C15H13NO4 | |||
Molecular weight | 326.39 g/mol | 313.36 g/mol | 271.26 g/mol | |||
Temperature | 173(2) K | 173(2) K | 173(2) K | |||
Wavelength | 0.71073 Å | 0.71073 Å | 0.71073 Å | |||
Crystal size | 0.020 × 0.170 × 0.200 mm | 0.080 × 0.130 × 0.250 mm | 0.090 × 0.090 × 0.130 mm | |||
Crystal habit | clear pale-yellow plate | clear light-yellow block | clear yellow block | |||
Crystal system | triclinic | monoclinic | monoclinic | |||
Space group | P -1 | P 1 21/n 1 | P 1 21/n 1 | |||
Unit cell dimensions | a = 9.330(8) Å | α = 102.188(9)° | a = 11.685(10) Å | α = 90° | a = 7.032(4) Å | α = 90° |
b = 9.472(8) Å | β = 105.805(9)° | b = 10.832(9) Å | β = 94.009(9)° | b = 14.522(9) Å | β = 99.276(7)° | |
c = 10.380(9) Å | γ = 90.679(9)° | c = 12.596(10) Å | γ = 90° | c = 12.660(8) Å | γ = 90° | |
Volume | 860.4(12) Å3 | 1590.(2) Å3 | 1275.9(13) Å3 | |||
Z | 2 | 4 | 4 | |||
Density (calculated) | 1.260 g/cm3 | 1.309 g/cm3 | 1.412 g/cm3 | |||
Absorption coefficient | 0.087 mm−1 | 0.091 mm−1 | 0.104 mm−1 | |||
F(000) | 348 | 668 | 568 |
No. | Identified Compounds | RT (min) | MW (g/mol) | Peak Area in Extracts (%) | ||||||
---|---|---|---|---|---|---|---|---|---|---|
MRT | MRE | Re1 | Re2 | Re3 | Re4 | Re5 | ||||
1 | Palmitic acid | 17.05 | 256 | - | - | < | 13.04 | - | - | - |
2 | Seselin | 18.27 | 228 | 7.0 | 8.5 | 12.4 | 2.4 | - | - | 2.9 |
3 | l-5-propylthiomethylhydantoin | 19.49 | 188 | 1.3 | 1.2 | - | - | - | - | 1.2 |
4 | Braylin | 19.55 | 258 | 9.9 | 11.4 | 13.7 | 6.1 | - | - | - |
5 | UC1 | 20.24 | 230 | < | < | - | - | 58.7 | 26.1 | - |
6 | Anisocoumarin B | 20.36 | 246 | - | - | - | - | - | 14.1 | - |
7 | UC2 | 20.85 | 244 | - | < | - | < | 2.1 | < | 2.3 |
8 | Nordentatin | 20.94 | 312 | 5.1 | 5.7 | - | < | 10.9 | 2.1 | 2.9 |
9 | UC3 | 21.08 | 297 | < | < | - | - | 2.8 | - | - |
10 | Clausine K | 21.25 | 271 | - | < | - | - | - | - | 15.0 |
11 | Dentatin | 21.48 | 326 | 70.6 | 68.0 | 61.7 | 10.7 | - | - | - |
12 | CA1 | 21.85 | 227 | - | < | - | - | - | 2.8 | - |
13 | CA2 | 23.29 | 293 | 1.9 | 2.3 | 3.5 | - | - | - | - |
14 | CA3 | 23.34 | 241 | - | - | - | 10.0 | - | - | - |
15 | CA4 | 24.85 | 279 | - | - | - | 1.9 | 1.1 | 11.2 | - |
16 | CA5 | 24.92 | 285 | - | < | - | - | 5.7 | - | - |
17 | 7-Hydroxyheptaphylline | 25.80 | 295 | - | - | - | - | - | 9.2 | - |
18 | Clionasterol | 28.41 | 414 | - | - | - | 10.2 | - | - | - |
Sample | DPPH Assay IC50 (µg/mL) | ABTS Assay IC50 (µg/mL) | β-Carotene Assay LPI (%) |
---|---|---|---|
MRT | 273.8 ± 9.6 e | 277.5 ± 3.1 f | 73.5 ± 1.4 bc |
MRE | 172.4 ± 1.2 d | 156.0 ± 1.3 d | 82.8 ± 1.1 a |
Dentatin | ne | ne | 37.9 ± 0.8 f |
Nordentatin | 49.2 ± 0.5 b | 69.9 ± 1.1 b | 69.8 ± 0.4 cd |
Clausine K | 2197.8 ± 53.3 f | 5264.0 ± 164.0 g | 60.6 ± 1.1 e |
Re1 | ne | ne | 67.7 ± 0.4 d |
Re2 | 283.5 ± 7.0 e | 188.5 ± 3.6 e | 73.7 ± 0.1 bc |
Re3 | 88.1 ± 3.2 c | 149.4 ± 3.2 d | 76.4 ± 0.7 b |
Re4 | 32.4 ± 0.3 ab | 38.5 ± 0.8 a | 76.1 ± 0.5 b |
Re5 | 90.9 ± 2.5 c | 151.8 ± 2.4 d | 81.2 ± 0.8 a |
BHT | 16.0 ± 0.2 a | 82.8 ± 1.1 c | 82.7 ± 0.3 a |
Sample | α-Amylase Inhibition IC50 (µg/mL) | Elastase Inhibition at 10 mg/mL (%) | Tyrosinase Inhibition IC50 (µg/mL) |
---|---|---|---|
MRT | 1383.3 ± 14.3 d | - | - |
MRE | 1004.6 ± 8.9 c | - | - |
Dentatin | - | - | - |
Nordentatin | - | 41.9 ± 0.8 a | - |
Clausine K | - | 21.9 ± 0.8 b | 179.5 ± 1.7 a |
Re1 | - | - | - |
Re2 | 573.8 ± 14.3 b | - | ne |
Re3 | - | - | 1798.0 ± 20.3 c |
Re4 | - | - | 243.8 ± 2.7 a |
Re5 | - | - | 2897.3 ± 25.0 d |
Control | |||
Acarbose | 39.6 ± 1.4 a | nd | nd |
Oleanolic acid (IC50) | nd | 0.3 ± 0.0 | nd |
Myricetin | nd | nd | 735.6 ± 7.2 b |
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Quan, N.V.; Xuan, T.D.; Anh, L.H.; Tran, H.-D. Bio-Guided Isolation of Prospective Bioactive Constituents from Roots of Clausena indica (Dalzell) Oliv. Molecules 2019, 24, 4442. https://doi.org/10.3390/molecules24244442
Quan NV, Xuan TD, Anh LH, Tran H-D. Bio-Guided Isolation of Prospective Bioactive Constituents from Roots of Clausena indica (Dalzell) Oliv. Molecules. 2019; 24(24):4442. https://doi.org/10.3390/molecules24244442
Chicago/Turabian StyleQuan, Nguyen Van, Tran Dang Xuan, La Hoang Anh, and Hoang-Dung Tran. 2019. "Bio-Guided Isolation of Prospective Bioactive Constituents from Roots of Clausena indica (Dalzell) Oliv" Molecules 24, no. 24: 4442. https://doi.org/10.3390/molecules24244442