Localization of Sesquiterpene Lactones Biosynthesis in Flowers of Arnica Taxa
Abstract
:1. Introduction
2. Results
2.1. SL Accumulation in Flower Heads in Arnica Taxa
2.2. SLs in Leaves
2.3. Influence of Flower Development Stages of SLs
2.4. Structure and Morphology of Flower Trichomes
2.5. Histochemical Analysis
3. Discussion
3.1. SL Accumulation in Flower Heads in Arnica Taxa
3.2. Histochemistry Studies
4. Materials and Methods
4.1. Plant Material
4.2. Reagents
4.3. LC-QTOF-MS Quantitative Analysis and Method Validation
Method Validation
- Linearity
- Accuracy and precision
- Recovery
- Limit of detection and limit of quantification
4.4. Extraction of SLs
4.5. Sample Preparation for Histochemistry Analysis
4.6. Immunolocalization of Farnesyl Policlonal Antibody
4.7. Histochemistry
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
Abbreviation
ABA | abscisic acid |
C/EBPβ | CCAAT/enhancer binding protein |
CV | coefficient of variation |
DAMPs | damage-associated molecular patterns |
DH | 11α, 13-dihydrohelenalin |
DHA | acetyldihydrohelenalin |
DHIB | isobutyryldihydrohelenalin |
DHIV | isovaleryldihydrohelenalin |
DHM | methacryloyldihydrohelenalin |
DHMB | 2-methylbutyryldihydrohelenalin |
DHT | tigloyldihydrohelenalin |
DMAPP | dimethylallyl pyrophosphate |
FDS | farnesyl diphosphate synthase |
FPP | farnesyl pyrophosphate |
GM-CSF | regulatory link between granulocyte macrophage-colony stimulating factor |
H | helenalin |
HA | helenalin acetate |
HIB | isobutyrylhelenalin |
HIV | isovalerylhelenalin |
HM | methacryloylhelenalin |
HMB | 2-methylbutyrylhelenalin |
HPLC | high-performance liquid chromatography |
HT | tigloylhelenalin |
LOD | limit of detection |
LOQ | limit of quantification |
MALDI-MS | matrix-assisted laser desorption/ionization-mass spectrometry imaging |
MAMPs | microbe-associated molecular patterns |
MEP | 2-C-methyl-D-erythritol-4-phosphate |
MVA | mevalonate |
NF-κB | nuclear factor kappa-light-chain-enhancer |
PAP | primary cause of lung disease |
PPI | isopentenyl diphosphate |
RSD | relative standard deviation |
SD | standard deviation |
SLs | sesquiterpene lactones |
SNARE | soluble N-ethylmaleimide-sensitive-factor attachment protein receptor |
STPS | sesquiterpene synthases |
UHPLC-MS | ultra-high performance liquid chromatography-mass spectrometry |
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A. montana L. | A. montana cv. Arbo | A. chamissonis Less. | ||||
---|---|---|---|---|---|---|
Buds | Full Flowering | Buds | Full Flowering | Buds | Full Flowering | |
DH | 0.04 ± 0.02 | 0.09 ± 0.06 | 0.02 ± 0.01 | 0.04 ± 0.01 | - | - |
H | 0.09 ± 0.04 | 0.27 ± 0.05 | 0.14 ± 0.03 | 0.35 ± 0.09 | 0.24 ± 0.03 | 0.13 ± 0.05 |
DHA | - | 0.03 ± 0.02 | 0.23 ± 0.01 | 0.52 ± 0.11 | - | - |
HA | - | - | 0.18 ± 0.03 | 0.54 ± 0.12 | - | - |
DHM | 0.53 ± 0.17 | 0.94 ± 0.46 | 0.54 ± 0.07 | 0.73 ± 0.12 | - | - |
HM | 0.19 ± 0.08 | 0.72 ± 0.21 | 0.56 ± 0.06 | 1.44 ± 0.23 | - | - |
DHIB | 0.38 ± 0.04 | 1.48 ± 0.76 | 0.46 ± 0.40 | 1.43 ± 0.28 | - | - |
HIB | 0.15 ± 0.06 | 0.97 ± 0.26 | 1.07 ± 0.23 | 4.06 ± 0.87 | - | - |
DHT | 1.70 ± 0.20 | 2.28 ± 0.87 | 0.75 ± 0.17 | 1.13 ± 0.19 | - | - |
HT | 0.82 ± 0.06 | 2.49 ± 0.75 | 1.09 ± 0.09 | 2.75 ± 0.38 | 0.02 ± 0.01 | 0.01 ± 0.01 |
DHMB/DHIV | 0.59 ± 0.11 | 1.22 ± 0.52 | 1.23 ± 0.11 | 2.47 ± 0.45 | - | - |
HMB/HIV | 0.33 ± 0.06 | 1.15 ± 0.32 | 3.41 ± 0.37 | 9.42 ± 1.45 | - | - |
Total H | 1.58 ± 0.31 | 5.59 ± 1.55 | 6.45 ± 0.75 | 18.57 ± 3.13 | 0.26 ± 0.03 | 0.14 ± 0.06 |
Total DH | 3.25 ± 0.53 | 6.03 ± 2.69 | 3.24 ± 0.12 | 6.32 ± 1.17 | - | - |
Total SL | 4.84 ± 0.67 | 11.63 ± 1.69 | 9.69 ± 0.68 | 24.88 ± 4.28 | 0.26 ± 0.03 | 0.14 ± 0.06 |
Arnica montana | Arnica montana cv. Arbo | ||||
---|---|---|---|---|---|
Non-grandural Trichomes | Grandural Trichomes | Diameter of Grandular Trichomes [µm] | Non-grandural Trichomes | Grandural Trichomes | Diameter of Grandular Trichomes [µm] |
16.95 ± 1.54 | 15.55 ± 3.33 | 32.33 ± 3.06 | 22.96 ± 2.63 | 18.09 ± 3.57 | 34.48 ± 3.83 |
Histochemical Tests | Color of Reaction Products | References |
---|---|---|
Legal’s reaction for methylene and methyl ketone. | Red to dark brown; concentration dependent after adding CH3COOH red | Positive for helenalin [88] |
Zimmermann reaction for methyl ketone and aldehyde. | Reddish purple | Positive for helenalin [88] |
Schiff’s reagent for aldehydes. | Red or magenta | Negative for helenalin [41,88,89] |
NADI for cytochrome oxidase | Stains lipids blue; fat inclusions, red-purple; and terpenes and resins, indigo to violet, according the proportion of oil and resin acids | [90] |
Succinate dehydrogenase with Neo-T | Light blue | [91] |
Vanillin for lactones | Stains helenalin yellow; after heating, turns reddish orange | [43] |
p-dimethylamino-benzaldehyde for lactones | Greyish yellow | [43] |
EP reaction for azulene and proazulenes | Green, blue or dark blue | [92] |
1% EDTA in water lactones | Greyish black | [42] |
2,4-Dinitrophenylhydrazine test for aldehydes and ketones, Brady’s reagent | Stains aliphatic carbonyls yellow; red to orange for aromatic carbonyls Precipitation on slides coated with glycerol, visible after several days | [89] |
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Parafiniuk, A.; Kromer, K.; Fleszar, M.G.; Kreitschitz, A.; Wiśniewski, J.; Gamian, A. Localization of Sesquiterpene Lactones Biosynthesis in Flowers of Arnica Taxa. Molecules 2023, 28, 4379. https://doi.org/10.3390/molecules28114379
Parafiniuk A, Kromer K, Fleszar MG, Kreitschitz A, Wiśniewski J, Gamian A. Localization of Sesquiterpene Lactones Biosynthesis in Flowers of Arnica Taxa. Molecules. 2023; 28(11):4379. https://doi.org/10.3390/molecules28114379
Chicago/Turabian StyleParafiniuk, Agata, Krystyna Kromer, Mariusz G. Fleszar, Agnieszka Kreitschitz, Jerzy Wiśniewski, and Andrzej Gamian. 2023. "Localization of Sesquiterpene Lactones Biosynthesis in Flowers of Arnica Taxa" Molecules 28, no. 11: 4379. https://doi.org/10.3390/molecules28114379