Does the Phytochemical Diversity of Wild Plants Like the Erythrophleum genus Correlate with Geographical Origin?
Abstract
:1. Introduction
- Cassaine-type diterpenoids with an ester amine arm (Figure 1B) result from esterification between the carboxylic group of a cassane-type tricyclic diterpene acid and the alcohol group of an aminoethanol (often N-methylethanolamine (CH3-NH-CH2-CH2-OH) or N,N-dimethylethanolamine ((CH3)2N-CH2-CH2-OH)) [26]. Ethanolamine can be formed by decarboxylation of a serine or by a transamination reaction (exchange of an amine group) between a glycoaldehyde and a glutamic acid [24,25].
2. Results
2.1. Metabolomics Analysis
2.2. Molecular Networks
2.2.1. Sub-Cluster A
2.2.2. Sub-Cluster B
2.2.3. Sub-Cluster C
2.2.4. Other Networks
2.3. Species-Specific Metabolite Features and Identification
3. Discussion
4. Materials and Methods
4.1. Field Sampling
4.2. Controlling the Identification and Origin of Samples
4.3. Metabolomics Analyses
4.3.1. Sample Preparation
4.3.2. LC-HRMS(/MS) Analysis
4.3.3. Metabolomics Data
4.3.4. Data Processing and Chemometrics on W4M
4.3.5. Statistical Analyses
4.3.6. Data Preprocessing with MZmine 2 and Molecular Network Analysis with MetGem
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Species | Population/ Country (*) | GPS Coordinates (Long/Lat) | Genetic Groups (**) | Block Abbreviation (Number of Individuals) | n |
---|---|---|---|---|---|
E. ivorense | Libreville/C | 9.3727/0.6187 | Ivo | A(5), B(6), C(7), D(5) | 23 |
E. suaveolens | Ouesso/RC | 16.4892/1.2926 | Ouesso-Sua (N) | A(4), 2B(1), C(2), D(3) | 10 |
UFA30/C | 13.9128/3.4287 | Sua (N) | A(1), B(2), C(1), D(4) | 8 | |
Lastourville & Mekambo/G | 12.952/−0.5345 & 13.9396/0.9618 | Sua (S) | C(1), D(2) | 3 |
Scaffold | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Number | Molecular Formula/RT (min) | m/z/δ (ppm) | R1 | R2 | R3 | R4 | R5 | R6 | Ref | More Abundant in: | Relative Abundance in Ouesso/ Sua */ ivo-Libr 1/ ivo-Libr 2 |
[A1] | C24H37NO5/16.97 | 420.2733/2.74 | H | COOCH3 | CH3 | H,H | O | OCH2CH2 NHCH3 | [17,32,33,34] | Sua * | 9/48/33/11 |
[A2] | C23H35NO5/16.75 | 406.2569/4.69 | H | COOCH3 | CH3 | H,H | O | NHCH2CH2OH/OCH2CH2NH2 | NEW | Sua * | 21/71/4/4 |
[A3] | C24H35NO5/14.54 | 434.2549/2.74 | H | COOCH3 | CH3 | O | O | OCH2CH2NHCH3 | [32,34] | Ouesso-Sua | 53/36/6/5 |
[A4] | C25H39NO5/17.16 | 434.2855/10.59 | H | COOCH3 | CH3 | H,H | O | OCH2CH2N(CH3)2 | [31,37,41,52] | Sua * | 24/52/14/11 |
[A5] | C24H35NO6/15.77 | 434.2555/4.11 | H | COOCH3 | CH3 | O | O | OCH2CH2NHCH3 | [32,34] | Ivo-Libr 2 | 9/11/28/53 |
[B1] | C26H39NO8/14.44 | 494.2757/1.74 | OCOCH3 | COOCH3 | CH3 | OH (or O) | O (or OH) | OCH2CH2NHCH3 | [34] | Sua * | 10/82/3/5 |
[B2] | C24H37NO7/12.62 | 452.2664/4.7 | OH | COOCH3 | CH3 | OH (or O) | O (or OH) | OCH2CH2NHCH3 | [43,46] | Ouesso-Sua | 45/26/19/9 |
[B3] | C25H37NO8/14.34 | 480.2607/7.32 | OCOCH3 | COOCH3 | CH3 | OH (or O) | O (or OH) | OCH2CH2NH2 | NEW | Sua * | 16/83/0/0 |
[B4] | C25H37NO8/14.51 | 480.2828/49 | OCOCH3 | COOCH3 | CH3 | OH (or O) | O (or OH) | OCH2CH2NH2 | NEW | Sua * | 24/70/4/3 |
[B5] | C27H41NO8/14.40 | 508.2980/10.64 | OCOCH3 | COOCH3 | CH3 | OMe (or O) | O (or OMe) | OCH2CH2NHCH3 | [43] | Ivo-Libr 2 | 2/4/39/55 |
[B6] | C30H45NO8/17.04 | 548.3212/1.09 | OCOC(CH3)=CHCH3 (tigloyl) or OCOCH=C(CH3)2 (methylcrotonyl) | COOCH3 | CH3 | OMe (or O) | O (or OMe) | OCH2CH2NHCH3 | NEW | Ivo | 0/0/48/52 |
[B7] | C30H47NO8/17.28 | 550.3350/ 4.45 | OCOCH(CH3)CH2CH3 or OCOCH2CH(CH3)2 | COOCH3 | CH3 | OMe (or O) | O (or OMe) | OCH2CH2NHCH3 | NEW | Ivo | 0/0/50/50 |
[B8] | C30H47NO9/14.05 | 566.3312/ 2.69 | OCOC(OH)(CH3)CH2CH3 or OCOCH(OH) CH(CH3)2 | COOCH3 | CH3 | OMe (or O) | O (or OMe) | OCH2CH2NHCH3 | NEW | Ivo | 0/1/51/48 |
[B9] | C28H43NO7/15.65 | 506.3102/ 2.04 | OCOC(OH)(CH3)CH2CH3 or OCOCH(OH) CH(CH3)2 | CH3 | CH3 | O | O | OCH2CH2NHCH3 | NEW | Ivo | 0/0/52/48 |
[B10] | C28H41NO6/17.87 | 488.2988/ 3.83 | OCOC(CH3)=CHCH3 or OCOCH=C(CH3)2 | CH3 | CH3 | O | O | OCH2CH2NHCH3 | NEW | Ivo-Libr 1 | 1/1/59/39 |
[B11] | C30H48NO9/14.17 | 566.3308/2.76 | OCOC(OH)(CH3)CH2CH3 or OCOCH(OH) CH(CH3)2 | COOCH3 | CH3 | OMe (or O) | O (or OMe) | OCH2CH2NHCH3 | NEW | Ivo-Libr 2 | 1/1/3/95 |
[B12] | C31H49NO12/10.40 | 628.3323/0.72 | O-glucopyrannosyl | COOCH3 | CH3 | OMe (or O) | O (or OMe) | OCH2CH2NHCH3 | NEW | Ivo-Libr 2 | 1/0/35/65 |
[B13] | C23H37NO4/13.27 | 392.2802/1.70 | OH | CH3 | CH3 | H,H | O | OCH2CH2NHCH3 | NEW | Ivo-Libr 1 | 4/7/63/27 |
[B14] | C23H37NO4/12.66 | 392.2789/1.62 | OH | CH3 | CH3 | O | H,H | OCH2CH2NHCH3 | NEW | Ivo-Libr1 | 5/6/62/27 |
[B15] | C28H45NO6/15.83 | 492.3314/1.15 | OCOC(OH)(CH3)CH2CH3 or OCOCH(OH) CH(CH3)2OCOCH2C(OH) (CH3)2 | CH3 | CH3 | H,H | O | OCH2CH2NHCH3 | [26] | Ivo-Libr1 | 1/3/53/43 |
[B16] | C27H43NO6/15.61 | 478.3067/20.1 | OCOC(OH)(CH3)CH2CH3 or OCOCH(OH) CH(CH3)2OCOCH2C(OH) (CH3)2 | CH3 | CH3 | H,H | O | OCH2CH2NH2 | NEW | Sua * | 21/61/7/11 |
[B17] | C22H35NO4/13.10 | 378.2625/3.67 | OH | CH3 | CH3 | H,H | O (or OH) | OCH2CH2NH2 | NEW | Sua * | 33/62/3/2 |
[C1] | C24H37NO7/11.17 | 452.2636/1.50 | OH | COOCH3 | CH3 | OH (or O) | O (or OH) | OCH2CH2NHCH3 | [43,46] | Ouesso-Sua | 60/36/1/3 |
[C2] | C23H35NO7/10.97 | 438.2501/3.36 | OH | COOCH3 | CH3 | OH (or O) | O (or OH) | OCH2CH2NH2 | NEW | Ouesso-Sua | 60/40/0/0 |
[C3] | C25H39NO7/11.31 | 466.2787/2.64 | OH | COOCH3 | CH3 | OH (or O) | O (or OH) | OCH2CH2NH(CH3)2 | NEW | Ouesso-Sua | 69/24/2/5 |
[BS1] | C24H35NO7/12.84 | 450.2477/1.27 (Biosigner 450.2492/2.07) | OH | COOCH3 | CH3 | O | O | OCH2CH2NHCH3 | NEW | Sua * | 40/59/0/1 |
[BS2] | C28H43NO6/18.48 | 490.3145/3.71 (Biosigner 490.3158/1.05) | OCOC(CH3)=CHCH3 or OCOCH=C(CH3)2 | CH3 | CH3 | OH (or O) | O (or OH) | OCH2CH2NHCH3 | NEW | Ivo-Libr 1 | 0/0/65/35 |
[BS3] | C28H43NO7/15.65 | 506.3102/2.04 (Biosigner 506.3113/0.14) | OCOC(OH)(CH3)CH2CH3 or OCOCH(OH) CH(CH3)2 | CH3 | CH3 | O | O | OCH2CH2NHCH3 | NEW | Ivo | 0/0/52/48 |
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Delporte, C.; Noret, N.; Vanhaverbeke, C.; Hardy, O.J.; Martin, J.-F.; Tremblay-Franco, M.; Touboul, D.; Gorel, A.; Faes, M.; Stévigny, C.; et al. Does the Phytochemical Diversity of Wild Plants Like the Erythrophleum genus Correlate with Geographical Origin? Molecules 2021, 26, 1668. https://doi.org/10.3390/molecules26061668
Delporte C, Noret N, Vanhaverbeke C, Hardy OJ, Martin J-F, Tremblay-Franco M, Touboul D, Gorel A, Faes M, Stévigny C, et al. Does the Phytochemical Diversity of Wild Plants Like the Erythrophleum genus Correlate with Geographical Origin? Molecules. 2021; 26(6):1668. https://doi.org/10.3390/molecules26061668
Chicago/Turabian StyleDelporte, Cédric, Nausicaa Noret, Cécile Vanhaverbeke, Olivier J. Hardy, Jean-François Martin, Marie Tremblay-Franco, David Touboul, Anais Gorel, Marie Faes, Caroline Stévigny, and et al. 2021. "Does the Phytochemical Diversity of Wild Plants Like the Erythrophleum genus Correlate with Geographical Origin?" Molecules 26, no. 6: 1668. https://doi.org/10.3390/molecules26061668