Chemical and Antifungal Variability of Several Accessions of Azadirachta indica A. Juss. from Six Locations Across the Colombian Caribbean Coast: Identification of Antifungal Azadirone Limonoids
Abstract
:1. Introduction
2. Results and Discussion
2.1. Total Limonoid Contents and Antifungal Activity of A. indica-Derived Extracts
2.2. Chemical Variability through Metabolic Profiling of Crude Extracts of A. indica
2.3. Integration of Chemical and Antifungal Activity Datasets for Detecting Bioactives
2.4. Validation of the OPLS Model by Direct Identification of Bioactives after High Performance Liquid Chromatography (HPLC)-Based Microfractionation
3. Materials and Methods
3.1. Plant Collection
3.2. Preparation of Crude Ethanolic Extracts
3.3. Measurement of Total Limonoid Contents (TLiC)
3.4. Analysis of the Effect of A. indica Extracts on Viability and Germination of F. oxysporum conidia
3.5. Liquid Chromatography Coupled to Mass Spectrometry (LC-MS) Analysis and Peak Annotations
3.6. Microfractionation of Extract 37 (SA_L_1) by Analytical-Scale High Performance Liquid Chromatography (HPLC)
3.7. Purification and Identification of Most-Active Compounds from Extract 37 by Semipreparative-Scale HPLC
3.8. Statistical Analyses
4. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Appendix A
Location | Accession | Coordinates |
---|---|---|
San Pedro de la Sierra (SPS) | 1 | 10°53′6.31″ N 74° 6′28.44″ W |
2 | 10°53′40.66″ N 74° 5′56.10″ W | |
3 | 10°53′41.15″ N 74° 5′53.93″ W | |
4 | 10°53′20.87″ N 74° 6′16.43″ W | |
5 | 10°52′53.63″ N 74° 9′9.93″ W | |
Santa Ana (SA) | 1 | 9°19′19.10″ N 74°34′46.31″ W |
2 | 9°19′39.14″ N 74°34′48.64″ W | |
3 | 9°19′39.49″ N 74°34′47.71″ W | |
4 | 9°19′39.62″ N 74°34′47.48″ W | |
5 | 9°19′39.71″ N 74°34′47.29″ W | |
6 | 9°19′13.63″ N 74°34′23.03″ W | |
Riohacha (R) | 1 | 11°31′28.03″ N 72°54′7.55″ W |
2 | 11°31′27.97″ N 72°54′7.90″ W | |
3 | 11°31′28.84″ N 72°54′8.95″ W | |
4 | 11°31′30.62″ N 72°54′13.34″ W | |
5 | 11°31′30.18″ N 72°54′13.74″ W | |
6 | 11°31′29.21″ N 72°54′15.56″ W | |
7 | 11°31′29.97″ N 72°54′16.63″ W | |
8 | 11°31′29.68″ N 72°54′18.33″ W | |
9 | 11°31′26.78″ N 72°54′11.65″ W | |
Mompox (M) | 1 | 9°14′36.17″ N 74°25′37.73″ W |
2 | 9°14′36.06″ N 74°25′37.68″ W | |
3 | 9°14′28.10″ N 74°25′22.49″ W | |
4 | 9°14′29.11″ N 74°25′24.05″ W | |
5 | 9°14′17.76″ N 74°25′15.06″ W | |
Santa Marta (SM) | 1 | 11°13′26.45″ N 74°11′6.14″ W |
2 | 11°13′26.29″ N 74°11′6.63″ W | |
3 | 11°13′26.16″ N 74°11′5.90″ W | |
4 | 11°13′26.07″ N 74°11′6.15″ W | |
5 | 11°13′25.92″ N 74°11′6.57″ W | |
Montería (Mo) | 1 | 8°45′44.71″ N 75°52′39.16″ W |
2 | 8°45′50.04″ N 75°52′43.17″ W | |
3 | 8°45′50.12″ N 75°52′43.08″ W | |
4 | 8°45′50.20″ N 75°52′43.00″ W | |
5 | 8°45′50.27″ N 75°52′42.96″ W | |
6 | 8°45′5.16″ N 75°53′27.34″ W | |
7 | 8°45′5.34″ N 75°53′27.24″ W | |
8 | 8°45′3.99″ N 75°53′27.19″ W | |
9 | 8°45′3.98″ N 75°53′26.99″ W | |
10 | 8°45′6.67″ N 75°53′28.20″ W |
No | Extract a | TLiC b | No | Extract a | TLiC b | No | Extract a | TLiC b | No | Extract a | TLiC b |
---|---|---|---|---|---|---|---|---|---|---|---|
1 | SPS_L_1 | 13.5 ± 0.5 | 22 | R_F_4 | 25.7 ± 1.5 | 43 | SA_F_2 | 17.6 ± 2.9 | 64 | Mo_L_9 | 12.4 ± 0.7 |
2 | SPS_L_2 | 14.8 ± 0.8 | 23 | R_F_5 | 21.1 ± 2.1 | 44 | SA_F_4 | 15.1 ± 1.8 | 65 | Mo_L_10 | 11.4 ± 0.8 |
3 | SPS_L_3 | 16.0 ± 0.6 | 24 | R_F_6 | 25.5 ± 1.5 | 45 | SA_F_5 | 13.1 ± 1.5 | 66 | Mo_F_1 | 13.7 ± 3.8 |
4 | SPS_L_4 | 15.8 ± 0.3 | 25 | R_F_7 | 28.8 ± 2.4 | 46 | SA_F_6 | 17.0 ± 2.7 | 67 | Mo_F_2 | 15.6 ± 0.7 |
5 | SPS_L_5 | 15.0 ± 1.0 | 26 | R_F_8 | 21.3 ± 2.1 | 47 | SA_S_2 | 48.5 ± 1.7 | 68 | Mo_F_3 | 16.2 ± 0.9 |
6 | SPS_F_4 | 20.4 ± 0.3 | 27 | R_F_9 | 23 ± 1.1.8 | 48 | SA_S_4 | 24.9 ± 4.2 | 69 | Mo_F_4 | 15.2 ± 0.4 |
7 | SPS_F_5 | 20.6 ± 1.4 | 28 | R_S_1 | 42.8 ± 3.2 | 49 | SA_S_5 | 38.5 ± 9.4 | 70 | Mo_F_5 | 15.7 ± 0.4 |
8 | SPS_S_4 | 23.0 ± 0.4 | 29 | R_S_2 | 33.4 ± 1.3 | 50 | SA_S_6 | 42.5 ± 5.8 | 71 | Mo_F_6 | 15.1 ± 1.1 |
9 | SPS_S_5 | 24.3 ± 0.7 | 30 | R_S_3 | 43.6 ± 1.0 | 51 | M_L_1 | 19.2 ± 0.7 | 72 | Mo_F_7 | 17.6 ± 2.9 |
10 | R_L_1 | 17.9 ± 1.6 | 31 | R_S_4 | 34.2 ± 1.5 | 52 | M_L_2 | 10.5 ± 0.8 | 73 | Mo_S_1 | 13.9 ± 3.0 |
11 | R_L_2 | 14.7 ± 3.0 | 32 | R_S_5 | 34.7 ± 6.1 | 53 | M_L_3 | 12.2 ± 0.8 | 74 | Mo_S_2 | 17.9 ± 4.2 |
12 | R_L_3 | 13.2 ± 2.6 | 33 | R_S_6 | 31.3 ± 2.2 | 54 | M_L_4 | 13.1 ± 1.5 | 75 | Mo_S_3 | 16.1 ± 1.3 |
13 | R_L_4 | 14.4 ± 2.1 | 34 | R_S_7 | 42.4 ± 2.4 | 55 | M_L_5 | 14.6 ± 7.3 | 76 | Mo_S_4 | 15.5 ± 1.3 |
14 | R_L_5 | 17.1 ± 1.4 | 35 | R_S_8 | 40.6 ± 2.7 | 56 | Mo_L_1 | 13.7 ± 1.8 | 77 | Mo_S_5 | 14.6 ± 4.4 |
15 | R_L_6 | 14.8 ± 1.8 | 36 | R_S_9 | 43.9 ± 1.9 | 57 | Mo_L_2 | 13.4 ± 2.4 | 78 | Mo_S_6 | 19.6 ± 1.8 |
16 | R_L_7 | 13.7 ± 1.7 | 37 | SA_L_1 | 6.7 ± 0.5 | 58 | Mo_L_3 | 12.4 ± 1.0 | 79 | Mo_S_7 | 16.5 ± 1.4 |
17 | R_L_8 | 17.3 ± 0.5 | 38 | SA_L_2 | 4.5 ± 0.4 | 59 | Mo_L_4 | 15.0 ± 0.3 | 80 | SM_L_1 | 32.6 ± 2.4 |
18 | R_L_9 | 17.6 ± 0.7 | 39 | SA_L_3 | 7.4 ± 0.6 | 60 | Mo_L_5 | 12.5 ± 0.4 | 81 | SM_L_2 | 33.0 ± 2.3 |
19 | R_F_1 | 21.5 ± 1.0 | 40 | SA_L_4 | 8.7 ± 0.8 | 61 | Mo_L_6 | 13.1 ± 0.9 | 82 | SM_L_3 | 31.7 ± 1.0 |
20 | R_F_2 | 21.4 ± 1.2 | 41 | SA_L_5 | 7.6 ± 0.8 | 62 | Mo_L_7 | 8.2 ± 0.5 | 83 | SM_L_4 | 43.6 ± 4.3 |
21 | R_F_3 | 20.0 ± 1.1 | 42 | SA_L_6 | 8.8 ± 0.5 | 63 | Mo_L_8 | 12.9 ± 0.6 | 84 | SM_L_5 | 38.7 ± 2.2 |
No | Extract a | IC50 c | No | Extract a | IC50 c | No | Extract a | IC50 c | No | Extract a | IC50 c |
---|---|---|---|---|---|---|---|---|---|---|---|
1 | SPS_L_1 | 0.56 ± 0.04 | 22 | R_F_4 | 9.63 ± 0.58 | 43 | SA_F_2 | 3.53 ± 0.28 | 64 | Mo_L_9 | 0.39 ± 0.05 |
2 | SPS_L_2 | 1.56 ± 0.12 | 23 | R_F_5 | 19.8 ± 0.99 | 44 | SA_F_4 | 0.77 ± 0.03 | 65 | Mo_L_10 | 0.16 ± 0.01 |
3 | SPS_L_3 | 0.23 ± 0.02 | 24 | R_F_6 | 0.65 ± 0.03 | 45 | SA_F_5 | 0.13 ± 0.01 | 66 | Mo_F_1 | 44.8 ± 1.79 |
4 | SPS_L_4 | 0.12 ± 0.01 | 25 | R_F_7 | 0.54 ± 0.04 | 46 | SA_F_6 | 0.68 ± 0.05 | 67 | Mo_F_2 | 4.91 ± 0.39 |
5 | SPS_L_5 | 0.25 ± 0.03 | 26 | R_F_8 | 0.35 ± 0.04 | 47 | SA_S_2 | 2.78 ± 0.25 | 68 | Mo_F_3 | 37.1 ± 3.71 |
6 | SPS_F_4 | 2.72 ± 0.27 | 27 | R_F_9 | 0.74 ± 0.03 | 48 | SA_S_4 | 32.6 ± 3.26 | 69 | Mo_F_4 | 2.60 ± 0.16 |
7 | SPS_F_5 | 1.35 ± 0.08 | 28 | R_S_1 | 0.25 ± 0.02 | 49 | SA_S_5 | 6.44 ± 0.52 | 70 | Mo_F_5 | 33.4 ± 4.01 |
8 | SPS_S_4 | 0.28 ± 0.03 | 29 | R_S_2 | 0.22 ± 0.01 | 50 | SA_S_6 | 35.8 ± 2.15 | 71 | Mo_F_6 | 0.88 ± 0.04 |
9 | SPS_S_5 | 0.27 ± 0.03 | 30 | R_S_3 | 0.18 ± 0.01 | 51 | M_L_1 | 2.32 ± 0.09 | 72 | Mo_F_7 | 1.09 ± 0.12 |
10 | R_L_1 | 0.32 ± 0.02 | 31 | R_S_4 | 0.11 ± 0.01 | 52 | M_L_2 | 26.8 ± 2.14 | 73 | Mo_S_1 | 1.95 ± 0.14 |
11 | R_L_2 | 3.64 ± 0.44 | 32 | R_S_5 | 7.35 ± 0.29 | 53 | M_L_3 | 2.12 ± 0.08 | 74 | Mo_S_2 | 1.63 ± 0.15 |
12 | R_L_3 | 1.03 ± 0.10 | 33 | R_S_6 | 0.08 ± 0.01 | 54 | M_L_4 | 38.6 ± 2.32 | 75 | Mo_S_3 | 1.77 ± 0.09 |
13 | R_L_4 | 0.45 ± 0.05 | 34 | R_S_7 | 0.55 ± 0.06 | 55 | M_L_5 | 33.9 ± 3.39 | 76 | Mo_S_4 | 29.8 ± 2.68 |
14 | R_L_5 | 9.67 ± 0.77 | 35 | R_S_8 | 0.21 ± 0.02 | 56 | Mo_L_1 | 41.6 ± 3.74 | 77 | Mo_S_5 | 3.67 ± 0.18 |
15 | R_L_6 | 28.2 ± 2.5 | 36 | R_S_9 | 0.78 ± 0.05 | 57 | Mo_L_2 | 27.9 ± 1.40 | 78 | Mo_S_6 | 35.6 ± 4.27 |
16 | R_L_7 | 7.52 ± 0.83 | 37 | SA_L_1 | 0.14 ± 0.01 | 58 | Mo_L_3 | 3.12 ± 0.22 | 79 | Mo_S_7 | 0.88 ± 0.04 |
17 | R_L_8 | 0.41 ± 0.04 | 38 | SA_L_2 | 0.17 ± 0.02 | 59 | Mo_L_4 | 31.2 ± 3.74 | 80 | SM_L_1 | 2.56 ± 0.23 |
18 | R_L_9 | 0.53 ± 0.03 | 39 | SA_L_3 | 1.25 ± 0.08 | 60 | Mo_L_5 | 42.9 ± 5.15 | 81 | SM_L_2 | 38.7 ± 4.26 |
19 | R_F_1 | 18.8 ± 1.32 | 40 | SA_L_4 | 0.98 ± 0.11 | 61 | Mo_L_6 | 27.8 ± 1.95 | 82 | SM_L_3 | 2.36 ± 0.21 |
20 | R_F_2 | 3.37 ± 0.40 | 41 | SA_L_5 | 21.6 ± 1.30 | 62 | Mo_L_7 | 1.46 ± 0.13 | 83 | SM_L_4 | 1.25 ± 0.10 |
21 | R_F_3 | 8.74 ± 1.05 | 42 | SA_L_6 | 4.51 ± 0.18 | 63 | Mo_L_8 | 0.69 ± 0.08 | 84 | SM_L_5 | 3.54 ± 0.28 |
Leaves | Fruits | Seeds | |||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
No a | m/z [M+H]+ | tR (min) | MF b | Annotation | Error | No a | m/z [M+H]+ | tR (min) | MF b | Annotation | Error | No a | m/z [M+H]+ | tR (min) | MF b | Annotation | Error |
1 | 287.0563 | 18.2 | C15H11O6+ | luteolin | −2.79 | 1 | 249.1133 | 11.8 | C14H17O4+ | hydroxyfraxinellone | −2.79 | 1 | 587.2479 | 27.6 | C31H39O11+ | humilinolide D | 2.21 |
2 | 635.2712 | 18.9 | C32H43O13+ | azadirachtin M | −1.42 | 2 | 261.1137 | 8.1 | C15H17O4+ | azedararide | −1.42 | 2 | 527.3379 | 23.7 | C32H47O6+ | azadirachtol | −1.33 |
3 | 613.3021 | 13.7 | C34H45O10+ | ohchinolal | −1.47 | 3 | 233.1168 | 9.9 | C14H17O3+ | fraxinellone | −1.47 | 3 | 721.2716 | 29.5 | C35H45O16+ | azadirachtin A | −1.25 |
4 | 995.4837 | 18.5 | C50H75O20+ | NAc | 1.41 | 4 | 357.1325 | 16.4 | C20H21O6+ | flowerone | 1.41 | 4 | 523.3041 | 20.9 | C32H43O6+ | azadironol | 3.44 |
5 | 571.2919 | 19.9 | C32H43O9+ | swietenin E | −2.10 | 5 | 345.0986 | 10.4 | C18H17O7+ | eupatilin | −2.10 | 5 | 555.2963 | 17.6 | C32H43O8+ | meliacinol | −1.08 |
6 | 239.1081 | 14.5 | C16H15O2+ | methoxychalcone | −3.76 | 6 | 223.2069 | 21.9 | C15H27O+ | α-cadinol | −3.76 | 6 | 635.2711 | 18.9 | C32H43O13+ | azadirachtin M | −1.26 |
7 | 597.3069 | 24.8 | C34H45O9+ | salannin | −1.00 | 7 | 291.0851 | 5.81 | C15H15O6+ | catechin | −1.00 | 7 | 369.2049 | 26.1 | C23H29O4+ | nimbothalin | 4.33 |
8 | 999.5148 | 22.5 | C50H79O20+ | NAc | 1.60 | 8 | 557.2766 | 34.1 | C31H41O9+ | swietenin C | 1.60 | 8 | 499.3069 | 26.9 | C30H43O6+ | azadirolic acid | −2.00 |
9 | 223.2071 | 21.9 | C15H27O+ | α-cadinol | −4.48 | 9 | 527.3361 | 23.7 | C32H47O6+ | azadirachtol | −4.48 | 9 | 467.2421 | 34.8 | C28H35O6+ | azadiradionolide | 2.57 |
10 | 999.5171 | 21.3 | C50H79O20+ | NAc | −0.70 | 10 | 555.2971 | 17.6 | C32H43O8+ | meliacinol | −0.70 | 10 | 513.2859 | 37.4 | C30H41O7+ | salimuzzalin | −1.36 |
1 | 2 | 3 | 4 | 5 | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
No | Type | δC | δH, mult, J (Hz) | Type | δC | δH, mult, J (Hz) | Type | δC | δH, mult, J (Hz) | Type | δC | δH, mult, J (Hz) | Type | δC | δH, mult, J (Hz) |
C-1 | CH | 157.1 | 7.14, d, 10.2 | CH | 157.4 | 7.10, d, 9.8 | CH2 | 33.5 | 1.41–1.79, m | CH | 157.3 | 7.05, d, 10.2 | CH | 157.9 | 7.12, d, 10.3 |
C-2 | CH | 125.9 | 5.92, d, 10.2 | CH | 126.1 | 5.95, d, 9.8 | CH2 | 38.3 | 2.18-2.41, m | CH | 126.8 | 5.89, d, 10.2 | CH | 126.3 | 5.93, d, 10.3 |
C-3 | C | 206.1 | C | 205.9 | C | 209.7 | C | 204.1 | C | 205.7 | |||||
C-4 | C | 40.4 | C | 40.5 | C | 41.2 | C | 43.4 | C | 40.8 | |||||
C-5 | CH | 49.8 | 2.20, d, 11.5 | CH | 50.2 | 2.23, d, 11.8 | CH | 47.1 | 2.07, d, 11.0 | CH | 48.6 | 2.13, d, 11.31 | CH | 49.6 | 2.76, d, 12.2 |
C-6 | CH | 68.2 | 4.39, dd, 11.5, 2.4 | CH | 68.6 | 4.34, dd, 11.8, 2.5 | CH | 68.8 | 4.17, dd, 11.0, 3.1 | CH | 67.5 | 4.25, dd, 2.7, 11.1 | CH | 76.4 | 5.44, dd, 12.2, 2.6 |
C-7 | CH | 79.0 | 5.34, d, 2.4 | CH | 77.5 | 4.95, d, 2.7 | CH | 79.2 | 5.24, d, 3.1 | CH | 82.3 | 5.29, d, 2.7 | CH | 68.4 | 4.06, d, 2.6 |
C-8 | C | 45.4 | C | 42.7 | C | 43.5 | C | 45.6 | C | 45.2 | |||||
C-9 | CH | 37.3 | 2.15–2.28, m | CH | 39.3 | 2.50–2.67, m | CH | 34.3 | 2.60–2.75, m | CH | 38.6 | 2.22, dd, 14.1, 5.1 | CH | 37.3 | 2.31, d, 12.6, 6.4 |
C-10 | C | 43.4 | C | 41.7 | C | 38.5 | C | 42.1 | C | 43.0 | |||||
C-11 | CH2 | 16.6 | 1.95–2.04, m (Ha) 1.70–1.81, m (Hb) | CH2 | 16.4 | 1.90–2.02 m (Ha) 1.71–1.87, m (Hb) | CH2 | 16.5 | 1.40–1.89, m | CH2 | 16.5 | 2.35–2.50, m (Ha) 2.05–2.21, m (Hb) | CH2 | 16.3 | 2.21–2.38, m (Ha) 2.02–2.29, m (Hb) |
C-12 | CH2 | 32.5 | 1.84–1.92, m (Ha) 2.26–2.33, m (Hb) | CH2 | 29.1 | 1.71–1.87, m (Ha) 2.40–2.42, m (Hb) | CH2 | 31.7 | 1.44–1.89, m | CH2 | 32.9 | 2.38–2.48, m (Ha) 2.79–2.85, m (Hb) | CH2 | 33.5 | 2.02–2.29, m (Ha) 2.36–2.43, m (Hb) |
C-13 | C | 47.3 | C | 45.5 | C | 47.1 | C | 59.5 | C | 46.9 | |||||
C-14 | C | 158.6 | C | 73.0 | C | 158.6 | C | 193.4 | C | 158.5 | |||||
C-15 | CH | 119.4 | 5.45, dd, 2.7, 1.9 | CH | 57.3 | 3.48–3.55, m | CH | 119.7 | 5.35, m | CH | 123.9 | 5.75, s | CH | 119.0 | 5.56, dd, 3.5, 1.7 |
C-16 | CH2 | 34.2 | 1.68–1.75, m (Ha) 2.32–2.41, m (Hb) | CH2 | 32.2 | 1.59–1.65, m (Ha) 2.10–2.31, m (Hb) | CH2 | 33.1 | 1.44–1.89, m | C | 208.0 | CH2 | 34.5 | 1.95–2.01, m (Ha) 2.41, ddd, 14.4, 7.2, 3.5 (Hb) | |
C-17 | CH | 51.8 | 2.84, dd, 10.6, 7.1 | CH | 39.4 | 2.66, dd, 3.6, 2.9 | CH | 51.4 | CH | 56.4 | 3.20, dd, 8.1, 1.7 | CH | 51.6 | 2.44, dd, 7.2, 3.5 | |
C-18 | CH3 | 20.4 | 0.85, s | CH3 | 21.8 | 0.95, s | CH3 | 20.7 | 0.77, s | CH3 | 18.4 | 1.08, s | CH3 | 20.6 | 0.84, s |
C-19 | CH3 | 20.1 | 1.15, s | CH3 | 20.4 | 1.11, s | CH3 | 16.6 | 0.81, s | CH3 | 16.1 | 1.17, s | CH3 | 14.0 | 1.14, s |
C-20 | C | 124.3 | C | 123.8 | C | 124.5 | CH | 143.6 | 3.33, m | C | 124.5 | ||||
C-21 | CH | 142.8 | 7.25, dd, 1.7, 1.0 | CH | 142.8 | 7.36, dd, 1.6, 0.8 | CH | 142.6 | 7.35, m | C | 203.1 | 9.78, d, 7.5 | CH | 142.6 | 7.26, dd, 1.7, 0.8 |
C-22 | CH | 111.1 | 6.32, dd, 1.7, 1.0 | CH | 111.3 | 6.19, dd, 1.6, 0.8 | CH | 111.7 | 6.17, m | CH2 | 32.1 | 2.02-2.34, m | CH | 111.2 | 6.25, dd, 1.7, 0.8 |
C-23 | CH | 139.4 | 7.38, t, 1.7 | CH | 139.6 | 7.16, t, 1.6 | CH | 139.5 | 7.19, m | CH3 | 21.9 | 1.24, t, 8.2 | CH | 139.4 | 7.37, t, 1.7 |
C-28 | CH3 | 31.6 | 1.27, s | CH3 | 31.8 | 1.19, s | CH3 | 31.6 | 1.132, s | CH3 | 25.0 | 1.22, s | CH3 | 26.9 | 1.19, s |
C-29 | CH3 | 20.6 | 1.30, s | CH3 | 19.4 | 1.32, s | CH3 | 19.5 | 1.21, s | CH3 | 21.3 | 1.25, s | CH3 | 19.5 | 1.25, s |
C-30 | CH3 | 26.8 | 1.39, s | CH3 | 21.8 | 1.39, s | CH3 | 26.2 | 1.25, s | CH3 | 25.7 | 1.26, s | CH3 | 20.1 | 1.32, s |
COCH3 | C | 171.8 | C | 171.6 | C | 172.2 | C | 169.2 | C | 172.3 | |||||
COCH3 | CH3 | 21.1 | 2.05, s | CH3 | 21.4 | 2.13, s | CH3 | 21.5 | 2.01, s | CH3 | 19.7 | 1.95, s | CH3 | 21.5 | 2.00, s |
OCH3 | - | - | - | CH3 | 3.50, s | - |
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Location | Abb a | Colombian Caribbean Areas | A (m) b | Climate conditions | Samples | |||
---|---|---|---|---|---|---|---|---|
KGC c | T (˚C) d | RF (mm) e | N f | PP g | ||||
Riohacha | R | La Guajira Peninsula | 5 | Bsh | 28.3 | 588 | 9 | L,F,S |
San Pedro de la Sierra | SPS | The Sierra Nevada | 1378 | Am | 18.9 | 2721 | 5 | L,F,S |
Santa Ana | SA | Magdalena River | 25 | Aw | 24.0 | 1468 | 6 | L,F,S |
Santa Marta | SM | The Sierra Nevada | 9 | Bsh | 28.3 | 512 | 5 | L |
Mompox | M | Magdalena River | 16 | Aw | 27.5 | 1573 | 10 | L |
Montería | Mo | Sinú Belt | 20 | Aw | 27.4 | 1225 | 5 | L,F,S |
No a | m/z [M+H]+ | tR (min) | MF b | Annotation | Error |
---|---|---|---|---|---|
1 | 453.2649 | 14.1 | C28H37O6+ | hydroxyazadirone isomer 1 | −1.76 |
2 | 469.2585 | 19.4 | C28H37O13+ | epoxyhydroxyazadirone | 1.07 |
3 | 455.2791 | 20.5 | C28H39O10+ | dehydrohydroxyazadirone | 1.32 |
4 | 485.2915 | 25.3 | C29H41O20+ | didehydrooxohydroxyazadirone | −2.47 |
5 | 453.2632 | 28.8 | C28H37O9+ | hydroxyazadirone isomer 2 | 1.99 |
Compounds | 1 | 2 | 3 | 4 | 5 |
---|---|---|---|---|---|
IC50 a | 1.48 ± 0.11 | 6.42 ± 0.26 | 15.17 ± 0.22 | 4.57 ± 0.23 | 10.07 ± 0.31 |
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Álvarez-Caballero, J.M.; Coy-Barrera, E. Chemical and Antifungal Variability of Several Accessions of Azadirachta indica A. Juss. from Six Locations Across the Colombian Caribbean Coast: Identification of Antifungal Azadirone Limonoids. Plants 2019, 8, 555. https://doi.org/10.3390/plants8120555
Álvarez-Caballero JM, Coy-Barrera E. Chemical and Antifungal Variability of Several Accessions of Azadirachta indica A. Juss. from Six Locations Across the Colombian Caribbean Coast: Identification of Antifungal Azadirone Limonoids. Plants. 2019; 8(12):555. https://doi.org/10.3390/plants8120555
Chicago/Turabian StyleÁlvarez-Caballero, Juan Manuel, and Ericsson Coy-Barrera. 2019. "Chemical and Antifungal Variability of Several Accessions of Azadirachta indica A. Juss. from Six Locations Across the Colombian Caribbean Coast: Identification of Antifungal Azadirone Limonoids" Plants 8, no. 12: 555. https://doi.org/10.3390/plants8120555