An Insight into Citrus medica Linn.: A Systematic Review on Phytochemical Profile and Biological Activities
Abstract
:1. Introduction
2. Materials and Methods
2.1. Search Strategy
2.2. Study Selection
2.3. Data Extraction
2.4. Methodological Quality Assessment
3. Results and Discussion
3.1. Study Characteristics
3.2. Phytochemistry
3.2.1. Macronutrients and Micronutrients
3.2.2. Polyphenols, Flavonoids, and Phenolic Acids
3.2.3. Terpenes
3.2.4. Coumarins
3.3. Other Compounds
3.4. Biological Activity
3.4.1. Antioxidant Activity
3.4.2. Antibacterial, Antiviral, and Antifungal Activity
3.4.3. Cytotoxic Activity
3.4.4. Anti-Inflammatory and Analgesic Activity
3.4.5. Other Activities
4. Conclusions
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
Abbreviations
ABTS | 2,2′-Azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) |
APE | Alginate extract and pectin filler |
COSY | Correlation spectroscopy |
CPE | Continuous phase-transition extraction |
C-RDI | Contribution reference daily intake |
DLA | Dalton’s lymphoma ascites |
DPPH | 2,2-Diphenyl-1-picrylhydrazyl |
DW | Dry weight |
EC50 | Half maximal effective concentration |
EAC | Ehrlich’s ascites carcinoma |
EtOH | Ethanol |
EI-MS | Electron ionization–mass spectrometry |
EO | Essential oil |
ERK | Extracellular signal-regulated kinase |
FW | FW |
GAE | Gallic acid equivalent |
GC–MS | Gas chromatography–mass spectrometry |
GC–MS–SPME | Gas chromatography–mass spectrometry–solid-phase microextraction |
HeLa | Henrietta Lacks |
HL60 | Human leukemia cell line |
HMQC | Heteronuclear multiple quantum coherence |
HMBC | Heteronuclear multiple bond coherence |
HPGPC | High-performance gel-permeation chromatography |
HPLC | High-performance liquid chromatography |
HPLC–PDA–MS | High-performance liquid chromatography–photodiode array–mass spectrometry |
HPLC–QTOF–MS | High-performance liquid chromatography–quadruple time of flight–mass spectrometry |
HRGC–MS | High-resolution gas chromatography–mass spectrometry |
HR–ESI–MS | High-resolution–electrospray ionization–mass spectrometry |
HR–EI–MS | High-resolution–electron ionization–mass spectrometry |
HR–MAS–NMR | High-resolution–magic angle sinning–nuclear magnetic resonance |
HY | Hydrolat |
IC50 | Half-maximal inhibitory concentration |
IkB-α: | Nuclear factor of kappa light polypeptide gene enhancer in B-cells inhibitor, alpha |
IL-6 | Interleukin 6 |
IL-1β | Interleukin 1β |
IL-10 | Interleukin 10 |
JNK | c-Jun N-terminal kinase |
LPS | Lipopolysaccharide |
MAPKs | Mitogen-activated protein kinase |
MeOH | Methanol |
MIC | Minimum inhibitory concentration |
NF-kB | Nuclear factor kappa-light-chain-enhancer of activated B cells |
NO | Nitric oxide |
NOESY | Nuclear Overhauser effect spectroscopy |
PC-3 | Human prostate adenocarcinoma cell line |
PLE | Pressure liquid extraction |
RAW 264.7 | Macrophage cell line |
RSA | Radical-scavenging activity |
SARS-CoV-2 | Severe Acute Respiratory Syndrome Coronavirus 2 |
SCF–CO2 | Super-critical fluid–carbon bioxide |
SH-SY5Y | Human neuroblastoma cell line |
TFC | Total flavonoid content |
TNF-α | Tumor necrosis factor alpha |
TPC | Total phenolic content |
UV | Ultraviolet |
UAHD | Hydro-distillation ultrasound-assisted extraction |
UAE | Ultrasound-assisted extraction |
UHPLC–QTOF–IMS | Ultra-performance liquid chromatography–quadruple time of flight–mass spectrometry |
Var. | Variety |
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Checklist for Assessment of Risks of Bias in Pre-Clinical Studies |
---|
Are the hypothesis and objective of the study clearly described? |
Are the main outcomes to be measured clearly described? |
Are the main findings of the study clearly described? |
Are the samples size calculations reported? |
Are the animals randomly housed during the experiment? |
Are the investigators blinded from knowledge which treatment used? |
Are the outcome assessors blinded? |
Is the dose/route of administration of Citrus medica L. properly reported? |
Is the dose/route of administration of the drug in co-treatment properly reported? |
Is the frequency of treatments adequately described? |
Nutrient Compounds | Part of Plant | Quantitative | References |
---|---|---|---|
Minerals | |||
Calcium (Ca) | peel, pulp | 107.39–195.91 mg/100 g FW | [17] |
Copper (Cu) | peel, pulp | 0.061–0.45 mg/100 g FW | [17] |
Iron (Fe) | peel, pulp | 0.82–2.92 mg/100 g FW | [17] |
Magnesium (Mg) | peel, pulp | 5.86–16.29 mg/100 g FW | [17] |
Manganese (Mn) | peel, pulp | 0.052–0.266 mg/100 g FW | [17] |
Potassium (K) | peel, pulp | 126.04–263.27 mg/100 g FW | [17] |
Sodium (Na) | peel, pulp | 6.74–27.92 mg/100 g FW | [17] |
Zinc (Zn) | peel, pulp | 0.24–0.51 mg/100 g FW | [17] |
Vitamins | |||
Ascorbic acid (vitamin C) | peel, pulp, exocarp, mesocarp, endocarp, seeds | 0.23–2.39 mg/100 g FW | [17] |
2.33–7.95 mg/100 g DW | [15] | ||
fructus | 11.61 ± 2.50 mg/100 g FW | [18] | |
peel | - | [19] | |
peel | - | [20] | |
fructus | - | [21] | |
juice | 18.49 ± 0.52 mg/100 g FW | [3] | |
Niacin (vitamin B3) | peel, pulp | 0.05–0.63 mg/100 g FW | [17] |
Pyridoxine (vitamin B6) | peel, pulp | 0.75–10.12 mg/100 g FW | [17] |
Riboflavin (vitamin B2) | peel, pulp, exocarp, mesocarp, endocarp, seeds | 0.37–1.16 mg/100 g FW | [17] |
1.85–6.38 mg/100 g DW | [15] | ||
Thiamin (vitamin B1) | peel, pulp, exocarp, endocarp | 1.32–3.65 mg/100 g FW | [17] |
0.18–0.40 mg/100 g DW | [15] | ||
Essential amino acids | |||
Histidine | peel, pulp | 7.68–38.04 mg/100 g FW | [17] |
Isoleucine | peel, pulp | 16.14–81.95 mg/100 g FW | [17] |
Leucine | peel, pulp | 30.05–126.24 mg/100 g FW | [17] |
Lysine | peel, pulp | 27.37–94.46 mg/100 g FW | [17] |
- | [22] | ||
Methionine | peel, pulp | 1.63–11.53 mg/100 g FW | [17] |
Phenylalanine | peel, pulp, exocarp, endocarp, mesocarp, seeds | 19.21–89.44 mg/100 g FW | [17] |
- | [15] | ||
Threonine | albedo, pulp | - | [22] |
Valine | peel, pulp, albedo, pulp | 29.64–121.92 mg/100 g FW | [17] |
- | [22] | ||
Non-essential amino acids | |||
Alanine | peel, pulp | 57.55–153.99 mg/100 g FW | [17] |
albedo, pulp | [22] | ||
Arginine | peel, pulp | 18.64–90.62 mg/100 g FW | [17] |
Asparagine | peel, oil glands, albedo, pulp | - | [22] |
Aspartic acid | peel, pulp | 232.86–637.32 mg/100 g FW | [17] |
Cystine | peel, pulp | 1.76–1.82 mg/100 g FW | [17] |
Glutamic acid | peel, pulp | 71.47–227.50 mg/100 g FW | [17] |
Glycine | peel, pulp | 21.15–108.48 mg/100 g FW | [17] |
Proline | peel, pulp | 55.22–150.18 mg/100 g FW | [17] |
- | [15] | ||
- | [22] | ||
Serine | peel, pulp | 22.45–78.84 mg/100 g FW | [17] |
Tryptophan | exocarp, endocarp, mesocarp | - | [17] |
Tyrosine | peel, pulp | 12.51–53.74 mg/100 g FW | [17] |
Macronutrients | |||
Moisture content | peel, pulp | 81.78–86.03 g/100 g FW | [17] |
Fat | peel, pulp | 0.39–0.56 g/100 g FW | [17] |
Protein | peel, pulp | 0.80–2.99 g/100 g FW | [17] |
Ash | peel, pulp | 0.44–1.23 g/100 g FW | [17] |
Carbohydrates | peel, pulp | 9.19–16.60 g/100 g FW | [17] |
Energy | peel, pulp | 53.74–73.06 g/100 g FW | [17] |
Glucose | peel, pulp | 0.92–2.27 g/100 g FW | [17] |
Fructose | peel, pulp | 1.60–2.95 g/100 g FW | [17] |
Sucrose | peel, pulp | 0.27–1.03 g/100 g FW | [17] |
Compounds | Formula | Structure | Extraction Method | Chemical Analysis | Part of the Plant | Quantitative | References |
---|---|---|---|---|---|---|---|
Apigenin | C15H12O5 | Maceration 70% EtOH | HPLC | flavedo | 62.80 mg/kg FW | [33] | |
Exhaustive maceration 70% EtOH | HPLC | flowers, leaves, mesocarp, endocarp | 58.00–941.00 mg/kg FW | [27] | |||
Maceration 100% EtOH | UPLC–DAD | peel and pulp | 24.26 ± 1.67 µg/g FW | [34] | |||
Apigenin-6,8-di-C-glucoside | C27H30O15 | UAE 50%MeOH | HPLC–Q/TOF–MS | fructus | - | [35] | |
Atalantoflavon | C21H18O4 | Maceration Acetone | COSY, NOESY, HMQC, HMBC, HR–ESI–MS | root bark, stem bark | - | [36] | |
Maceration MeOH | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |||
Catechin | C15H14O6 | UAE EtOH 80% | UHPLC–QTOF–IMS | mesocarp, endocarp, seeds | 5.14–57.87 mg/100 g DW | [15] | |
Maceration 100% EtOH | UPLC–DAD | flavedo, pulp | 4.34–68.78 µg/g FW | [34] | |||
Dihydrokaem-pferide | C16H14O6 | Maceration 70% MeOH | UV, MS, NMR | leaves | - | [38] | |
Dihydroquercetin | C15H12O7 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, endocarp, seeds | - | [15] | |
Epicatechin | C15H14O6 | Maceration 100% EtOH | UPLC–DAD | flavedo, pulp | 9.85–105.10 µg/g FW | [34] | |
Eriocitrin (Eriodictyol-7-O-rutinoside) | C27H32O15 | Maceration MeOH and 0.1% HCl | HPLC–PDA–MS | fructus | - | [39] | |
Herbacetin | C15H10O7 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, mesocarp, seeds | - | [15] | |
Hesperetin | C16H14O6 | Dynamic maceration 70% EtOH | HPLC | flavedo | 0.39–1.82 mg/g DW | [26] | |
UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, endocarp, mesocarp, seeds | - | [15] | |||
Maceration 70% EtOH | HPLC | flavedo | 50.4 mg/kg FW | [33] | |||
Exhaustive maceration 70% EtOH | HPLC | flowers, leaves, mesocarp, endocarp | 203.80 mg/kg FW | [27] | |||
Hesperetin-7-O-rutinoside | C28H34O15 | Maceration MeOH and 0.1% HCl | HPLC–PDA–MS | fructus | - | [39] | |
Hesperidin | C28H34O15 | PLE MeOH | HPLC–DAD | fructus | 30.36 µg/mL | [40] | |
Dynamic maceration with 70% EtOH | HPLC | flavedo | 1.86–2.77 mg/g DW | [26] | |||
UAE 80% EtOH | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp, seeds | 383.02–3307.25 mg/100 g DW | [15] | |||
Exhaustive maceration 70% EtOH | HPLC | flowers, leaves, mesocarp, endocarp | 9.00–224.30 mg/kg FW | [27] | |||
UAE 50% MeOH | HPLC–Q/TOF–MS | fructus | 0.84–1.84 mg/g DW | [35] | |||
Kaempferol 3-O-rutinoside | C27H32O15 | Dynamic maceration 70% EtOH | HPLC | flavedo | - | [26] | |
Limocitrol 3-α-l-arabinopyranosyl-(1->3) -galactoside | C29H34O18 | CPE 85% EtOH | UPLC–QTOF–MS/MS | fructus | - | [41] | |
Lonchocarpol A | C25H28O5 | Maceration Acetone | COSY, NOESY, HMQC, HMBC, HR–ESI–MS | root bark, stem bark | - | [36] | |
Naringenin 7-O-glucoside | C21H22O10 | UAE 80% EtOH | UHPLC–QTOF–IMS | exocarp, mesocarp, seeds | - | [15] | |
Naringin | C27H32O14 | Exhaustive extraction 70% EtOH | HPLC | fructus | 556.00 mg/kg FW | [27] | |
UAE 80% EtOH | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp, seeds | 36.82–295.15 mg/100 g DW | [15] | |||
UAE 80% EtOH | HPLC–QTOF–MS | fructus | 0.43–0.61 mg/g DW | [35] | |||
Maceration 70% EtOH | HPLC | flavedo | 18.60 mg/kg FW | [33] | |||
Neodiosmin (Diosmetin-7-O-neoheseridoside) | C28H32O15 | CPE 85% EtOH | UPLC–QTOF–MS/MS | fructus | - | [41] | |
Diosmin | Exhaustively maceration 70% EtOH | HPLC | flowers, leaves, mesocarp, endocarp | 18.20–372.50 mg/kg FW | [27] | ||
Neohesperidin (hesperetin-7-O-neohesperidoside) | C28H34O15 | Maceration MeOH and 0.1% HCl | HPLC–PDA–MS | fructus | - | [39] | |
Nobiletin | C21H22O8 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp, seeds | 25.63–94.32 mg/100 g DW | [15] | |
Phloretin-3′, 5′-di-C-glucoside | C27H34O15 | Maceration MeOH and 0.1%HCl | HPLC–PDA–MS | fructus | - | [39] | |
Quercetin | C15H10O7 | Soxhlet MeOH 65 °C | HPLC | fructus 2 | 0.025 mg/g DW | [42] | |
Maceration 70% EtOH | HPLC | flavedo | 18.20 mg/kg FW | [33] | |||
Dynamic maceration 70% EtOH | HPLC | flavedo | 1.62–3.01 mg/g DW | [26] | |||
Exhaustive maceration 70% EtOH | HPLC | flowers, leaves, mesocarp, endocarp | 11.00–580.80 mg/kg FW | [27] | |||
Rutin | C27H30O16 | Maceration 100% EtOH | UPLC–DAD | flavedo and pulp | 19.39–115.47 µg/g FW | [34] | |
Dynamic maceration 70% EtOH | HPLC | flavedo | 0.20–0.42 mg/g DW | [26] | |||
UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp | 74.08–328.82 mg/100 g DW | [15] | |||
70% MeOH | UV, MS, NMR | leaves | - | [38] | |||
Sakuranetin | C16H14O5 | Maceration on cold 70% MeOH | UV, MS, NMR | leaves | - | [38] | |
Stachannin Scutellarein 4′-methyl ether 7-glucoside | C22H22011 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, endocarp, seeds | - | [15] | |
Tangeritin | C20H20O7 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp, seeds | 18.96–164.88 mg/100 g DW | [15] | |
Vitexin | C21H20010 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, endocarp, seeds | - | [15] | |
Vitexin-2-rhamnoside | C27H30O14 | PLE MeOH | HPLC–DAD | fructus | - | [40] | |
3,5,6-Trihydroxy-3′,4′,7-trimethoxyflavone | C18H16O8 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp, seeds | - | [15] | |
5,7-Dihydroxy-3′, 4′, 5′-trimethoxyflavone | C18H16O7 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, seeds | - | [15] | |
5-Demethylnobiletin | C20H20O8 | Dynamic maceration 70% EtOH | HPLC | flavedo | - | [26] | |
6,8-di-C-glucosyldiosmetin | C28H32016 | PLE MeOH | HPLC–DAD | fructus | 13.51 µg/mL | [40] | |
7-O-Methyl-aromadendrin | C16H14O6 | Maceration on cold 70% MeOH | UV, MS, NMR | leaves | - | [38] | |
Scoparin (Chrysoeriol 8-C-glucoside) | C22H22O11 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Phenolic acids | |||||||
Benzoic acid | C7H6O2 | Soxhlet with MeOH | HPLC | fructus | 0.00103 mg/g DW | [42] | |
Caffeic acid | C9H8O4 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp, seeds | 36.38–122.88 mg/100 g DW | [15] | |
100% EtOH for 24 h | UPLC–DAD | flavedo, pulp | 6.97–7.11 µg/g FW | [34] | |||
Chlorogenic acid | C16H18O9 | UAE EtOH 80% | UHPLC–QTOF–IMS | mesocarp, endocarp, seeds | 66.66–109.85 mg/100 g DW | [15] | |
Gallic acid | C7H605 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp | 13.51–26.36 mg/100 g DW | [15] | |
100% EtOH | UPLC–DAD | flavedo, pulp | 16.84–39.02 µg/g FW | [34] | |||
Soxhlet with MeOH | HPLC | fructus | 0.30 mg/g DW | [42] | |||
p-Coumaric acid | C9H803 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp, seeds | 3.90–28.09 mg/100 g DW | [15] | |
Methyl-4-hydroxycinnamate | C10H10O3 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Salicylic acid | C7H6O3 | Soxhlet with MeOH | HPLC | fructus | 0.16 mg/g DW | [42] | |
trans-Cinnamic acid | C9H8O2 | UAE EtOH 80% | UHPLC–QTOF–IMS | mesocarp, endocarp, seeds | 0.42–13.06 mg/100 g DW | [15] | |
trans-Ferulic acid | C10H10O4 | UAE EtOH 80% | UHPLC–QTOF–IMS | exocarp, mesocarp. Endocarp, seeds | 19.85–96.79 mg/100 g DW | [15] | |
100% EtOH | UPLC–DAD | flavedo and pulp | 106.36–295.97 µg/g FW | [34] | |||
Dynamic maceration 70% EtOH | HPLC | flavedo | 0.21–1.08 mg/g DW | [26] | |||
Neolignans | |||||||
(7E)-1-Allyl alcohol-5,6-(11-isopropyl)-furanyl-3′,5′-dimethoxy-4′-glycerol-9′-isovalerate-3,4,7′,8′-benzodioxane neolignan | C33H40O11 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
2(7E,10′E,11E)-1-(9-Methoxyl)-propenyl-5-hydroxy-6-prenyl-8′-methylol-11′,16′-dihydroxy-15′,17′-dimethoxy-10′-phenylallyl alcohol-3,4,7′,8′-benzodioxane neolignan | C35H38O10 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(7E,11E)-1-(9-Methoxyl)-propenyl-5-hydroxy-6-geranyl-16′-hydroxy-15′,17′-dimethoxyphenyl-8′,11′-dimethylol-benzofuranyl 3,4,7′,8′-benzodioxane neolignan | C39H44O11 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
1-(18,19-Dimethyl)-propanol-4-hydroxyl-5,6-(13-hydroxyl-12-methoxyl)-phenylethyl-7′-(4′-hydroxyl-5′-methoxy)-phenyl-9′-O-β-D glucopyranosyl-phenanthrofuran neolignan | C36H42O13 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
1-(17-Furanyl)-ethyl-4-hydroxyl-5,6-(13-hydroxyl-12-methoxyl)- phenylethyl-7′-(3′,4′,5′-trimethoxy)-phenyl-9′-O-β-D-glucopyranosyl- phenanthrofuran neolignan | C39H42O14 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
1-(17Z)-Methyl-butanol-4-hydroxyl-5,6-(13-hydroxyl-12-methoxyl)- phenylethyl-7′-(4′-hydroxy-3′,5′-dimethoxy)-phenyl-9′-O-β-D-glucopyranosyl-phenanthrofuran neolignan | C37H42O14 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(9′E)-4,5-(11,12-Dimethyl)- pyranyl-7′-(4′-hydroxy)- phenyl-4′-propenyl-8′-methylol-furanyl-6′-acetyl-1′,6-biphenyl-7-ketone | C32H28O6 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(9E,9′E)-5-Isopentenyl-7′-(4′-hydroxy-5′-methoxy)-phenyl-4′-propenylketone-8′-methylol-furanyl-6′-acetyl-1′,6-biphenyl-7-ketone | C33H30O8 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(7E,10E)-4,5′-Dihydroxy-5-isopentenol-6-(7,8-trans allyl)-alcohol7′-(4′-hydroxy-3′,5′-dimethoxyl)-phenyl-9′,9′-dimethylol-1′,7′- bineolignan | C34H34O11 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(7E)-5′-Hydroxy-4,5-(13,14-dimethyl)-pyranyl-6-allyl alcohol-7′-(4′-hydroxy-3′,5′-dimethoxyl)-phenyl-9′,9′-dimethylol-1′,7′-bineolignan | C34H32O10 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(7S,8R)-9′,3-Dimethoxyl isoamericanol | C20H22O7 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(7S,8R,7′S,8′R)-7,8–7′,8′-trans-7′,8′-Z-Sesquiverniciasin A | C27H25O9 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(7S,8R,7′S,8′R)-7,8–7′,8′-trans-7′,8′-E-Sesquiverniciasin A | C27H25O9 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
Selamoellenin B | C21H24O7 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
Dendronbibisline A | C30H26O7 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
Dendronbibisline B | C25H24O7 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
Dendronbibisline C | C32H32O8 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
Dendronbibisline D | C33H34O8 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
Herpetiosol B | C30H34O9 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
Herpetosiols C | C31H34O9 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
Silychristin A | C25H22O10 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
Silychristin B | C25H22O10 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(7S,8R)-threo-1′-[3′-Hydroxy-7-(4-hydroxy-3- methoxyphenyl)-8-hydroxymethyl-7,8-dihydrobenzofuran]acryl-aldehyde | C19H18O6 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] | |
(-)-(7R,8S,7′E)-4-Hydroxy-3,5,5′,9′-tetramethoxy-4′,7-epoxy-8,3′-neolign-7′-en-9-ol | C22H26O7 | reflux 95% EtOH | NMR, HR–ESI–MS | fructus | - | [32] |
Compounds | Formula | Structure | Extraction Method * | Analysis | Part of the Plant | Abundance | References |
---|---|---|---|---|---|---|---|
Monoterpenes | |||||||
ɑ-Thujene | C10H16 | I | GC–MS | flavedo | 0.2% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.28–0.59% | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.2–0.9% | [48] | |||
VIII | GC–MS–SPME | industrial essence | - | [57] | |||
X | GC–MS | fructus | 1.20–1.29% | [53] | |||
XI | GC–MS | fructus | 0.87% | [58] | |||
XII | HR–MAS–NMR | oil glands | - | [22] | |||
XV | GC–MS | exocarp, mesocarp | 0.4–0.5% | [54] | |||
ɑ-Thujone | C10H16O | XIII | GC–MS | fresh fructus | 4.29–5.05% | [45] | |
Ꞵ-Thujene | C10H16 | VIII | GC–MS–SPME | industrial essence | 0.78% | [57] | |
ɑ-Pinene | C10H16 | I | GC–MS | flavedo | 0.49% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.69–1.46% | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.6–2.1% | [48] | |||
X | GC–MS | fructus | 2.92–3.40% | [53] | |||
XI | GC–MS | fructus | 1.99% | [58] | |||
XII | HR–MAS–NMR | oil glands | - | [22] | |||
XIII | GC–MS | fresh fructus | 6.38–7.73% | [45] | |||
XV | GC–MS | exocarp, mesocarp | 1.4–1.6% | [54] | |||
Sabinene | C10H16 | I | GC–MS | flavedo | 0.64% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.14–0.22% | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.1–0.3% | [48] | |||
XII | HR–MAS–NMR | oil glands | - | [22] | |||
Camphene | C10H16 | II, III, IV | HRGC–MS | flavedo | 0.01% | [49] | |
V, VI, VII | GC–MS | flavedo | trace | [48] | |||
VIII | GC–MS–SPME | industrial essence | 0.04% | [57] | |||
X | GC–MS | fructus | 0.02–0.03% | [53] | |||
XIII | GC–MS | fresh fruit | 0.22–0.29% | [45] | |||
cis-Sabinene hydrate | C10H18O | II, III, IV | HRGC–MS | flavedo | 0.04–0.06% | [49] | |
V, VI, VII | GC–MS | flavedo | trace | [48] | |||
trans-Sabinene hydrate | C10H18O | VIII | GC–MS–SPME | industrial essence | - | [57] | |
Ꞵ-Pinene | C10H16 | I | GC–MS | flavedo | 0.63% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.69–1.47% | [49] | |||
V, VI, VII | GC–MS | flavedo | 1.0–2.0% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 20.07% | [57] | |||
X | GC–MS | fructus | 2.48–2.88% | [53] | |||
XI | GC–MS | fructus | 2.02% | [58] | |||
XII | HR–MAS–NMR | flavedo, oil glands | - | [22] | |||
XIII | GC–MS | fresh fructus | 2.64–3.18% | [45] | |||
XIV | GC–MS | exocarp, mesocarp | 2.4–2.5% | [54] | |||
Myrcene | C10H16 | I | GC–MS | flavedo | 0.89 | [50] | |
II, III, IV | HRGC–MS | flavedo | 1.13–1.47% | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.8–1.6% | [48] | |||
XII | HR–MAS–NMR | oil glands | - | [22] | |||
VIII | GC–MS–SPME | industrial essence | 2.24% | [57] | |||
X | GC–MS | fructus | 1.64–1.76% | [53] | |||
XI | GC–MS | fructus | 1.25% | [58] | |||
Limonene | C10H16 | I | GC–MS | flavedo | 15.20% | [50] | |
II, III, IV | HRGC–MS | flavedo | 25.70–60.30 g/100 g DW | [49] | |||
V, VI, VII | GC–MS | flavedo | 34.6–60.8% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 41.07% | [57] | |||
X | GC–MS | fructus | 51.24–57.63% | [53] | |||
XI | GC–MS | fructus | 52.44% | [58] | |||
XII | HR–MAS–NMR | flavedo, oil glands, albedo | - | [22] | |||
XIII | GC–MS | fresh fructus | 32.07–36.37% | [45] | |||
XIV | UHPLC–QTOF–IMS | exocarp, mesocarp, endocarp, seeds | - | [15] | |||
XV | GC–MS | exocarp, mesocarp | 75.8–76.2% | [54] | |||
Decane | C10H22 | II, III, IV | HRGC–MS | flavedo | trace | [49] | |
Decanal | C10H20O | II, III, IV | HRGC–MS | flavedo | 0.04–0.07 | [49] | |
V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 0.27% | [57] | |||
Octyl acetate | C10H20O2 | II, III, IV | HRGC–MS | flavedo | 0.01% | [49] | |
VIII | GC–MS | industrial essence | 0.16% | [57] | |||
Citronellol | C10H20O | II, III, IV | HRGC–MS | flavedo | 0.03–0.11% | [49] | |
cis-Limonene oxide | C10H16O | II, III, IV | HRGC–MS | flavedo | 0.01% | [49] | |
VIII | GC–MS–SPME | industrial essence | - | [57] | |||
trans-Limonene oxide | C10H16O | II, III, IV | HRGC–MS | flavedo | trace | [49] | |
VIII | GC–MS | industrial essence | 0.28% | [57] | |||
trans-Carveol | C10H16O | V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |
Carveol | C10H16O | XV | GC–MS | mesocarp | 0.1% | [54] | |
Camphor | C10H16O | II, III, IV | HRGC–MS | flavedo | 0.01% | [49] | |
Citronellal | C10H18O | II, III, IV | HRGC–MS | flavedo | 0.04–0.06% | [49] | |
V, VI, VII | GC–MS | flavedo | 0.1–0.2% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 0.27% | [57] | |||
XII | HR–MAS–NMR | oil glands | - | [22] | |||
XIII | GC–MS | fresh fructus | 0.11% | [45] | |||
Borneol | C10H18O | II, III, IV | HRGC–MS | flavedo | 0.01% | [49] | |
(Z)-Ꞵ-Ocimene | C10H16 | II, III, IV | HRGC–MS | flavedo | 0.75–1.19% | [49] | |
V, VI, VII | GC–MS | flavedo | 1.4–1.5% | [48] | |||
VIII | GC–MS–SPME | industrial essence | - | [57] | |||
XI | GC–MS | fructus | 0.94% | [58] | |||
(E)-Ꞵ-Ocimene | C10H16 | II, III, IV | HRGC–MS | flavedo | 1.10–1.74% | [49] | |
V, VI, VII | GC–MS | flavedo | 1.9–2.1% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 0.07% | [57] | |||
XIII | GC–MS | fresh fructus | 0.55–0.99% | [45] | |||
X | GC–MS | fructus | 0.23–0.93% | [53] | |||
XI | GC–MS | fructus | 0.65% | [58] | |||
XV | GC–MS | exocarp, mesocarp | 1.1–1.2% | [54] | |||
Citral | C10H16O | VIII | GC–MS–SPME | industrial essence | - | [57] | |
X | GC–MS | fructus | 1.96–2.34% | [53] | |||
XII | HR–MAS–NMR | flavedo | - | [22] | |||
XV | GC–MS | mesocarp | 0.1% | [54] | |||
Octanal | C8H16O | II, III, IV | HRGC–MS | flavedo | 0.01% | [49] | |
V, VI, VII | GC–MS | flavedo | - | [48] | |||
VIII | GC–MS–SPME | industrial essence | 0.31% | [57] | |||
ɑ-Phellandrene | C10H16 | II, III, IV | HRGC–MS | flavedo | 0.04–0.05% | [49] | |
XV | GC–MS | mesocarp | trace | [54] | |||
V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |||
X | GC–MS | fructus | 0.1% | [53] | |||
δ-3-Carene | C10H16 | I | GC–MS | flavedo | 2.30% | [50] | |
II, III, IV | HRGC–MS | flavedo | trace | [49] | |||
3-Carene | C10H16 | XIII | GC–MS | fresh fructus | 8.15–9.01% | [45] | |
4-Carene | C10H16 | VIII | GC–MS–SPME | industrial essence | 0.10% | [57] | |
γ-Terpinene | C10H16 | I | GC–MS | flavedo | 10.27% | [50] | |
II, III, IV | HRGC–MS | flavedo | 21.19–23.44% | [49] | |||
V, VI, VII | GC–MS | flavedo | 22.1–24.6% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 8.35% | [57] | |||
X | GC–MS | fructus | 27.01–33.71% | [53] | |||
XI | GC–MS | fructus | 28.41% | [58] | |||
XII | HR–MAS–NMR | flavedo, oil glands | - | [22] | |||
XIII | GC–MS | fresh fructus | 22.44–25.23% | [45] | |||
XV | GC–MS | exocarp, mesocarp | 15.0–16.5% | [54] | |||
ɑ-Terpinene | C10H16 | II, III, IV | HRGC–MS | flavedo | 0.35–0.41% | [49] | |
V, VI, VII | GC–MS | flavedo | trace | [48] | |||
X | GC–MS | fructus | 1.28% | [53] | |||
XI | GC–MS | fructus | 0.81% | [58] | |||
Terpinolene | C10H16 | I | GC–MS | flavedo | 0.91% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.87–1.00% | [49] | |||
V, VI, VII | GC–MS | flavedo | 1.0–1.2% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 0.33% | [57] | |||
X | GC–MS | fructus | 1.25–1.54% | [53] | |||
XIII | GC–MS | industrial essence | - | [45] | |||
XV | GC–MS | exocarp, mesocarp | 0.2–0.6% | [54] | |||
Linalool | C10H18O | I | GC–MS | flavedo | 1.15% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.10–0.20 g/100 g DW | [47] | |||
V, VI, VII | GC–MS | flavedo | 0.1–0.3% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 1.73% | [57] | |||
XIII | GC–MS | fresh fructus | 0.16–0.18% | [45] | |||
Linalool oxide | C10H18O2 | VIII | GC–MS–SPME | industrial essence | 0.28% | [57] | |
Allocimene | C10H16 | I | GC–MS | flavedo | 0.70% | [50] | |
Terpinen-4-ol | C10H18O | I | GC–MS | flavedo | 1.02% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.04–0.06% | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.1–0.2% | [48] | |||
X | GC–MS | fructus | 0.34–0.51% | [53] | |||
VIII | GC–MS–SPME | industrial essence | 0.31% | [57] | |||
XIII | GC–MS | fresh fructus | 0.69–0.88% | [45] | |||
ɑ-Terpineol | C10H18O | I | GC–MS | flavedo | 2.64% | [50] | |
V, VI, VII | GC–MS | flavedo | 0.1–0.3% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 0.10% | [57] | |||
X | GC–MS | fructus | 0.48–0.58% | [53] | |||
XIII | GC–MS | fresh fruit | 1.17–1.61% | [45] | |||
XV | GC–MS | exocarp, mesocarp | 0.1–0.4% | [54] | |||
Nerol | C10H18O | I | GC–MS | flavedo | 4.69% | [50] | |
V, VI, VII | GC–MS | flavedo | 0.1–0.3% | [48] | |||
XIII | GC–MS | fresh fructus | 0.9–1.53% | [45] | |||
Neral | C10H16O | II, III, IV | HRGC–MS | flavedo | 1.20–9.40 g/100 g DW | [49] | |
V, VI, VII | GC–MS | flavedo | trace | [48] | |||
VIII | GC–MS–SPME | industrial essence | 2.49% | [57] | |||
X | GC–MS | fructus | 0.45% | [53] | |||
XII | HR–MAS–NMR | flavedo | - | [22] | |||
XIII | GC–MS | fresh fructus | 1.04–1.60% | [45] | |||
p-Cymen-8-ol | C10H14O | II, III, IV | HRGC–MS | flavedo | 0.01% | [47] | |
p-Cymene | C10H14 | V, VI, VII | GC–MS | flavedo | 0.4–0.6% | [48] | |
XIV | GC–MS | exocarp, mesocarp | 0.2–0.7% | [54] | |||
VIII | GC–MS–SPME | industrial essence | 5.92% | [57] | |||
XIII | GC–MS | fresh fructus | 1.64–2.77% | [45] | |||
Geraniol | C10H18O | I | GC–MS | flavedo | 4.63% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.10–8.50 g/100 g DW | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.1–0.7% | [48] | |||
X | GC–MS | fructus | 0.55–0.58% | [53] | |||
VIII | GC–MS-SPME | industrial essence | 0.27% | [57] | |||
XIII | GC–MS | fresh fructus | 1.18–2.02% | [45] | |||
Perillal | C10H14O | VIII | GC–MS–SPME | industrial essence | 0.10% | [57] | |
Cuminol | C10H14O | VIII | GC–MS–SPME | industrial essence | 0.03% | [57] | |
Carvacrol | C10H14O | II, III, IV | HRGC–MS | flavedo | trace | [49] | |
Perilla aldehyde | C10H14O | II, III, IV | HRGC–MS | flavedo | 0.01–0.02% | [49] | |
Sesquiterpenes | |||||||
δ-Elemene | C15H24 | II, III, IV | HRGC–MS | flavedo | 0.06–0.16% | [49] | |
V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |||
Ꞵ-Elemene | C15H24 | I | GC–MS | flavedo | 0.1% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.1% | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |||
X | GC–MS | flavedo | 0.1% | [53] | |||
Copaene | C15H24 | X | GC–MS | fructus | 0.02% | [53] | |
trans-Caryophyllene | C15H24 | I | GC–MS | flavedo | 0.41% | [50] | |
ɑ-Bisabolol | C15H26O | V, VI, VII | GC–MS | flavedo | 0.2% | [48] | |
ɑ-Bergamotene | C15H24 | I | GC–MS | flavedo | 1.09% | [50] | |
XV | GC–MS | exocarp, mesocarp | 0.3–0.6% | [54] | |||
X | GC–MS | fructus | 0.07% | [53] | |||
V, VI, VII | GC–MS | flavedo | 0.2–1.7% | [48] | |||
ɑ-Himachalene | C15H24 | XV | GC–MS | exocarp, mesocarp | 0.1–0.6% | [54] | |
γ-Gurjunene | C15H24 | XV | GC–MS | mesocarp | trace | [54] | |
ɑ-Humulene | C15H24 | I | GC–MS | flavedo | 0.13% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.1% | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |||
X | GC–MS | fructus | - | [53] | |||
(Z)-β-Farnesene | C15H24 | I | GC–MS | flavedo | 0.14% | [50] | |
II, III, IV | HRGC–MS | flavedo | trace | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |||
α-Bisabolene | C15H24 | I | GC–MS | flavedo | 0.10% | [50] | |
IX | GC–MS | leaves | - | [59] | |||
β-Bisabolene | C15H24 | I | GC–MS | flavedo | 1.39% | [50] | |
II, III, IV | HRGC–MS | flavedo | 0.03–0.05% | [49] | |||
V, VI, VII | GC–MS | flavedo | 0.2–2.6% | [48] | |||
VIII | GC–MS–SPME | industrial essence | 0.30% | [57] | |||
Spathulenol | C15H24O | I | GC–MS | flavedo | 0.1% | [50] | |
V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |||
α-cis-Bergamotene | C15H24 | II, III, IV | HRGC–MS | flavedo | 0.02–0.03% | [49] | |
E-β-Caryophyllene | C15H24 | II, III, IV | HRGC–MS | flavedo | 0.10 g/100 g DW | [49] | |
VIII | GC–MS | industrial essence | 0.23% | [57] | |||
IX | GC–MS | leaves | - | [59] | |||
X | GC–MS | fructus | 0.06% | [53] | |||
XIII | GC–MS | fresh fructus | 0.27–0.46% | [45] | |||
XIV | UHPLC–QTOF–IMS | mesocarp | - | [15] | |||
α-trans-Bergamotene | C15H24 | II, III, IV | HRGC–MS | flavedo | 0.29–0.45% | [49] | |
V, VI, VII | GC–MS | flavedo | 0.2–1.7% | [48] | |||
IX | GC–MS | leaves | - | [59] | |||
(E)-β-Farnesene | C15H24 | II, III, IV | HRGC–MS | flavedo | trace | [49] | |
XV | GC–MS | exocarp | 0.2% | [54] | |||
IX | GC–MS | leaves | - | [59] | |||
(Z)-β-Santalene | C15H24 | II, III, IV | HRGC–MS | flavedo | 0.01% | [49] | |
Valencene | C15H24 | II, III, IV | HRGC–MS | flavedo | 0.03–0.07% | [49] | |
Bicyclogermacrene | C15H24 | II, III, IV | HRGC–MS | flavedo | 0.03–0.04% | [49] | |
(Z)-α-Bisabolene | C15H24 | II, III, IV | HRGC–MS | flavedo | 0.03–0.05% | [49] | |
β-Cadinene | C15H24 | XIII | GC–MS | fresh fructus | 0.74–1.09% | [45] | |
α-Cedrene | C15H24 | XIII | GC–MS | fresh fructus | 0.55–0.64% | [45] | |
(E,E)-α-Farnesene | C15H24 | V, VI, VII | GC–MS | flavedo | trace | [48] | |
(Z)-α-Farnesene | C15H24 | XV | GC–MS | exocarp | 0.6% | [54] | |
α-Farnesene | C15H24 | X | GC–MS | fructus | 0.1% | [53] | |
XV | GC–MS | mesocarp | 0.2% | [54] | |||
(Z)-γ-Bisabolene | C15H24 | II, III, IV | HRGC–MS | flavedo | trace | [49] | |
Germacrene B | C15H24 | V, VI, VII | GC–MS | flavedo | 0.1–0.3% | [48] | |
X | GC–MS | fructus | - | [53] | |||
Gemacrene D | C15H24 | IX | GC–MS | leaves | - | [59] | |
X | GC–MS | fructus | 0.15–0.19% | [53] | |||
Bicyclogermacrene | C15H24 | IX | GC–MS | leaves | - | [59] | |
X | GC–MS | fructus | 0.06% | [53] | |||
(E)-Nerolidol | C15H26O | V, VI, VII | GC–MS | flavedo | 0.1–0.3% | [48] | |
IX | GC–MS | leaves | - | [59] | |||
Β-Bisabolene | C15H24 | II, III, IV | HRGC–MS | flavedo | 0.40–0.67% | [49] | |
Farnesol | C15H26O | V, VI, VII | GC–MS | flavedo | trace | [48] | |
Farnesal | C15H24O | V, VI, VII | GC–MS | flavedo | trace | [48] | |
Triterpenoids (Limonoids) | |||||||
Limonyl acetate | C28H34O9 | XIV | UHPLC–QTOF–IMS | exocarp, seeds | - | [15] | |
Limonin | C26H30O8 | XVII | HPLC | citron waste | 3.08 mg/100 g DW | [56] | |
XVI | EI–MS, HR–EI–MS | fresh fructus | - | [43] | |||
XIV | HPLC–Q/TOF–MS | fructus | 0.45–0.86 mg/g DW | [35] | |||
XVIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |||
Nomilin | C28H34O9 | XVII | HPLC | citron waste | 0.87 mg/100 g DW | [56] | |
XVI | EI–MS, HR–EI–MS | fresh fructus | - | [43] | |||
XIV | HPLC–Q/TOF–MS | fructus | 1.97–3.84 mg/g DW | [35] | |||
Citrusin | C28H34O11 | XVI | EI–MS, HR–EI–MS | fresh fructus | - | [43] | |
Obacunone | C26H30O7 | XVI | EI–MS, HR–EI–MS | fresh fructus | - | [43] | |
XIV | HPLC–Q/TOF–MS | fructus | 0.15–0.36 mg/g DW | [35] | |||
Nomilinic acid | C28H36O10 | XIV | UHPLC–QTOF–IMS | exocarp, seeds | - | [15] | |
Terpenoids | |||||||
Geranyl acetate | C12H20O2 | I | GC–MS | flavedo | 0.75% | [50] | |
Citronellyl acetate | C12H22O2 | II, III, IV | HRGC–MS | flavedo | 0.10 g/100 g DW | [49] | |
V, VI, VII | GC–MS | flavedo | 0.1–0.2% | [48] | |||
Dihydrolinalyl acetate | C12H22O2 | II, III, IV | HRGC–MS | flavedo | trace | [49] | |
β-lonone | C13H20O | XIII | GC–MS | fresh fructus | 0.20–0.49% | [45] | |
Linalyl acetate | C12H20O2 | VIII | GC–MS | industrial essence | 1.82% | [57] |
Compounds | Formula | Structure | Extraction Method | Method Analyses | Part of the Plant | Quantitative | References |
---|---|---|---|---|---|---|---|
Oxypeucedanin hydrate | C16H16O6 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | 2.03–21.30 g/100 g DW | [43] | |
Scoparone (6,7-dimethoxycoumarin) | C11H10O4 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
PLE MeOH | HPLCDAD | fructus | 38.79 µg/mL | [40] | |||
UAE | HPLC–Q/TOF–MS | fructus | - | [35] | |||
Skimmin | C15H16O8 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Haploperoside A | C22H28O13 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Leptodactylone | C11H10O5 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Herniarin (7-methoycoumarin) | C10H8O3 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Isomeranzin | C15H16O4 | UAE | HPLC–Q/TOF–MS | fructus | - | [35] | |
Scopoletin | C10H8O4 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
PLE MeOH | HPLC–DAD | fructus | 53.56 µg/mL | [40] | |||
Isoscopoletin | C10H8O4 | PLE MeOH | HPLC–DAD | fructus | 63.06 µg/mL | [40] | |
Umbelliferone (7-hydroxycoumarin) | C9H6O3 | MeOH under reflux | EI-MS, HR–EI–MS | fresh fruit | - | [43] | |
PLE MeOH | HPLC–DAD | fructus | 40.23 µg/mL | [40] | |||
Nordentatin | C19H20O4 | MeOH under reflux | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Maceration in acetone | COSY, NOESY, HMQC, HMBC, HR–ESI–MS | root bark, stem bark | - | [36] | |||
2-pyrone | C5H4O2 | Maceration and UAE MeOH | GC–MS | exocarp, mesocarp | 23.4–33.1% | [54] | |
Citropten (5,7-dimethoxycoumarin) | C11H10O4 | PLE MeOH | HPLC–DAD | fructus | 106.47 µg/mL | [40] | |
MeOH under reflux | HR–EI–MS1 | fresh fruits | 0.16–0.45 mg/g DW | [43] | |||
Maceration of peel with n-hexane at room temperature | GC–MS | fructus | 12.64% | [50] | |||
UAE | HPLC–Q/TOF–MS | fructus | 0.18–0.45 mg/g DW | [35] | |||
Bergapten | C12H8O4 | PLE MeOH | HPLC–DAD | fructus | 35.07 µg/mL | [40] | |
UAE | HPLC–Q/TOF–MS | fructus | - | [35] | |||
Maceration MeOH | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |||
Citrumedin-B | C24H28O4 | Acetone at room temperature | COSY, NOESY, HMQC, HMBC, HR–ESI–MS | root bark, stem bark | - | [36] | |
Xanthyletin | C14H12O3 | PLE MeOH | HPLC–DAD | fructus | - | [40] | |
UAE with CHCl3 | MEKC (micellar electrokinetic capillary chromatography) | root bark | - | [60] | |||
Xanthoxyletin | C15H14O4 | UAE with CHCl3 | MEKC (micellar electrokinetic capillary chromatography) | root bark | - | [60] | |
5,8-dimethoxhypsoralene | C12H8O4 | Maceration MeOH | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] |
Compounds | Formula | Structure | * Extraction Method | Method Analyses | Part of the Plant | Abundance | References |
---|---|---|---|---|---|---|---|
Alkaloids | |||||||
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid | C12H12N2O2 | IX | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Acridine derivatives | |||||||
Medicacridone | C20H21NO4 | VIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |
Citracridone-I | C20H19NO5 | VIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |
citracridone-III | C19H17NO5 | VIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |
5-hydroxynoracronycine 3 | C19H17NO4 | VIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |
Xanthones | |||||||
Medicaxanthone | C51H75O8 | VIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |
Lichenxanthone | C15H12O6 | VIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |
Glycol | |||||||
2,3-Butanediol | C4H10O2 | X | GC–MS | exocarp, mesocarp | 23.7% | [54] | |
Furan derivatives | |||||||
Furfural | C5H4O2 | X | GC–MS | exocarp, mesocarp | 3.9% | [54] | |
2(3H)-Furanone, 5-methyl | C8H12O2 | X | GC–MS | exocarp, mesocarp | 0.9% | [54] | |
5- 5-Hydroxymethylfurfural | C6H6O3 | X | GC–MS | exocarp, mesocarp | 1.9% | [54] | |
Hydrocarbons | |||||||
1,3-Cyclopentadiene | C5H6 | XIII | GC–MS | fresh fructus | 1.75–2.36% | [45] | |
Benzene | C6H6 | XI | GC–MS | fructus | 1.67% | [58] | |
Eicosane | C20H42 | I | GC–MS | flavedo | 0.10% | [50] | |
Nonacosane | C29H60 | I | GC–MS | flavedo | 0.10% | [50] | |
Mono or polyunsaturated aldehyde | |||||||
Undecanal | C11H22O | V, VI, VII | GC–MS | flavedo | 0.1–0.2% | [48] | |
II, III, IV | HRGC–MS | flavedo | 0.03–0.06% | [49] | |||
Dodecanal | C12H24O | II, III, IV | HRGC–MS | flavedo | 0.02–0.03% | [49] | |
V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |||
9,17-octadecadienal | C18H32O | I | GC–MS | flavedo | 9.29% | [50] | |
16-Octadecenal | C18H34O | I | GC–MS | flavedo | 0.10% | [50] | |
Nonanal | C9H18O | II, III, IV | HRGC–MS | flavedo | 0.04–0.07% | [49] | |
Tetradecanal | C14H28O | V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |
Pentadecanal | C15H30O | V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |
Phenylpropanoids | |||||||
Coniferin | C16H22O8 | IX | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Syringin | C17H24O9 | IX | EI–MS, HR–EI-MS | fresh fruit | - | [43] | |
Phytosterols | |||||||
Lupeol | C26H32O7 | VIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |
Stigmasterol | C29H48O | VIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |
Ꞵ-Sitosterol | C29H50O | VIII | ESI–HR, EI–MS, HMQC, HMBC | bark | - | [37] | |
Fatty acids and their esters | |||||||
Lauric acid | C12H24O2 | I | GC–MS | flavedo | 0.11% | [50] | |
Myristic acid | C14H28O2 | I | GC–MS | flavedo | 0.23% | [50] | |
Palmitic acid | C16H32O2 | I | GC–MS | flavedo | 5.17% | [50] | |
Hexadecanal | C16H32O | XIII | GC–MS | mesocarp | 1.6% | [54] | |
V, VI, VII | GC–MS | flavedo | 0.1% | [48] | |||
Pentadecanoic acid methyl ester | C16H32O2 | I | GC–MS | flavedo | 0.22% | [50] | |
Palmitoleic acid | C17H32O2 | I | GC–MS | flavedo | 0.19% | [50] | |
Heptadecanoic acid | C17H34O2 | I | GC–MS | flavedo | 0.20% | [50] | |
Stearic acid | C18H36O2 | I | GC–MS | flavedo | 0.18% | [50] | |
16-Octadecenal | C18H34O | I | GC–MS | flavedo | 0.10% | [50] | |
Linoleic acid, methyl ester | C19H34O2 | I | GC–MS | flavedo | 0.19% | [50] | |
Linolenic acid, methyl ester | C19H32O2 | I | GC–MS | flavedo | 0.41%0.30% | [50] | |
Stearic acid, methyl ester | C19H38O2 | I | GC–MS | flavedo | 0.30% | [50] | |
Benzoates | |||||||
Methyl vanillate methyl ester | C9H10O4 | IX | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Methyl benzoate | C8H8O2 | IX | EI–MS, HR–EI–MS | fresh fruit | - | [43] | |
Methyl paraben | C8H8O3 | IX | EI–MS, HR–EI–MS | fresh fruit | - | [43] |
Compounds | Molecular Weight | Extraction Method | Method Analyses | Part of the Plant | Abundance | References |
---|---|---|---|---|---|---|
Polysaccharides | ||||||
CMSPB80-1 | 103 kDa | Alkali extraction | HPGPC, FT–IR, methylation analysis, GC–MS, NMR | fructus | - | [61] |
CMSPW90-1 | 18.8 kDa | Hot water | HPGPC, FT–IR, methylation analysis, GC–MS, NMR | pulp | - | [62] |
CMSPW90-M1 | 75.4 kDa | Hot water | HPGPC, FT–IR, methylation analysis, GC–MS, NMR | pulp | - | [62] |
CMSPA90-1 | 17.6 kDa | Acid extraction | HPGPC, FT–IR, methylation analysis, GC–MS, NMR | fructus | 97.77% ± 1.4% (w/w) DW | [63] |
FCp-1, FCp-2, FCp-3, and FCp-4 | 113.9, 32.6, 140.3, and 177.1 kDa respectively | Hot water | acid hydrolysis, methylation, IR, GC–MS, and NMR | fructus | - | [64] |
CM-1 and CM-2 | 21.520 kDa, 22.303 kDa respectively | Hot water | Monosaccharide composition, linkage, and NMR | fructus | - | [65] |
K-CLMP | 3.76 × 103 kDa | Hot water | methylation analysis, NMR | fructus | 5.81% | [66] |
Crude polysaccharides (FCPs) | - | Hot water | FT–IR | fructus | 3.19 ± 0.10% | [67] |
Test/Model | Concentration/Dosage Tested/Results | Part of the Plant | Extraction Method | Reference |
---|---|---|---|---|
Antioxidant activity | ||||
ABTS | RSA 87.94% 0.2 mg/mL | fructus | CPE | [41] |
DPPH | RSA 89.86% at 0.8 mg/mL | |||
ORAC | 928.64 µmol TE/g | |||
DPPH | 112.18 μg ascorbic acid/ mL | fructus | Soxhlet | [42] |
NO | 112.18 μg ascorbic acid/ mL | |||
TPC | 177.50 ± 4.95 mgGAE/g | |||
TFC | 165.52 ± 0.65 mgQUE/g | |||
TPC | 227.45 ± 1.04 mg GAE/100 g FW | peel | MAE | [17] |
88.76 ± 1.38 mg GAE/100 g FW | pulp | |||
DPPH | 22.79 ± 0.12 IC50 μg GAE/mL | peel | ||
22.79 ± 0.12 IC50 μg GAE/mL | pulp | |||
ABTS | 214.81 ± 1.45 mg TE/100 g FW | peel | ||
71.53 ± 0.84 mg TE/100 g FW | pulp | |||
DPPH | EC50 827.26 µg/mL | peel | Maceration | [20] |
TPC | 66.36 μg GAE/mg | peel | ||
51.21 μg GAE/mg | pulp | |||
TFC | 40.17μg cathecol equivalent/mg | peel | ||
37.9μg cathecol equivalent/mg | pulp | |||
DPPH | 0.80 ± 0.07 (IC50 mg/mL) | peel | Maceration | [33] |
ABTS | 3.48 ± 1.0 (IC50 mg/mL) | |||
BCB | 0.23 ± 0.002 (IC50 mg/mL) | |||
FRAP | 3.9 ± 0.5 P (µm Fe (II)/g) | |||
DPPH | 147 ± 1.23 IC50 µg/mL | peel | Maceration | [50] |
BCB | 3 ± 0.05 IC50 µg/mL at 30 min | |||
Bovine brain peroxidation assay | 2472 ± 4.19 IC50 µg/mL | |||
DPPH | 72.00 ± 0.82% scavenging activity | juice | Maceration | [3] |
TPC | 309.08 ± 3.06 mgGAE/g | |||
DPPH | EC50 102.9 µg/mL | leaves | Maceration | [38] |
TPC | 398.0 ± 3.2 mg/100 g FW | flowers | Exhaustive maceration | [27] |
401.6 ± 5.1 mg/100 g FW | leaves | |||
181.3 ± 3.1 mg/100 g FW | immature mesocarp | |||
262.6 ± 3.7 mg/100 g FW | immature endocarp | |||
123.1 ± 6.5 mg/100 g FW | mature mesocarp | |||
109.4 ± 2.9 mg/100 g FW | mature endocarp | |||
TFC | 266.9 ± 7.2 mg QUE/100 g FW | flowers | ||
97.5 ± 2.8 mg QUE/100 g FW | leaves | |||
95.7 ± 3.2 mg QUE/100 g FW | immature mesocarp | |||
64.9 ± 3.2 mg QUE/100 g FW | immature endocarp | |||
43.1 ± 1.2 mg QUE/100 g FW | mature mesocarp | |||
37.5 ± 1.6 mg QUE/100 g FW | mature endocarp | |||
DPPH | 425.0 ± 2.95 µg Ascorbic acid/mL | flowers | ||
502.0 ± 3.01 µg Ascorbic acid/mL | leaves | |||
382.0 ± 2.45 µg Ascorbic acid/mL | immature mesocarp | |||
>1000 µg Ascorbic acid/mL | immature endocarp | |||
>1000 µg Ascorbic acid/mL | mature mesocarp | |||
>1000 µg Ascorbic acid/mL | mature endocarp | |||
BCB | 2.8 ± 0.002 µg/mL at 30 min | flowers | ||
>100 µg/mL at 30 min | leaves | |||
3.7 ± 0.007 µg/mL at 30 min | immature mesocarp | |||
4.1 ± 0.009 µg/mL at 30 min | immature endocarp | |||
36.6 ± 0.075 µg/mL at 30 min | mature mesocarp | |||
3.5 ± 0.008 µg/mL at 30 min | mature endocarp | |||
TPC | 227.45 mg GAE/100 g FW | peel | Maceration 70% MeOH | [26] |
88.76 mg GAE/100 g FW | pulp | |||
DPPH | IC50 22.79 μg GAE/ml | peel | ||
IC50 54.74 μg GAE/mL | pulp | |||
TPC | 2.52 ± 0.07 mg GAE/g | exocarp | UAE | [54] |
1.74 ± 0.02 mg GAE/g | mesocarp | |||
TFC | 2.20 ± 0.26 mg QE/g | exocarp | ||
1.50 ± 0.06 mg QE/g | mesocarp | |||
ABTS | 55.8 ± 5.4% RSA | exocarp | ||
52.0 ± 0.4% RSA | mesocarp | |||
54.1 ± 0.2% RSA | EO | Hydro-distillation | ||
3.1 ± 0.2% RSA | Hy | |||
DPPH | 55.7 ± 1.20% RSA | exocarp | UAE | |
46.7 ± 0.82% RSA | mesocarp | |||
26.4 ± 0.74% RSA | EO | Hydro-distillation | ||
2.5 ± 0.3% RSA | Hy | |||
DPPH | 77.2% RSA | EO | Hydro-distillation | [46] |
TPC | 2.74 ± 1.12 mg GAE/g | fructus | UAE | [35] |
TFC | 2.41 ± 2.03 mg QUE/g | fructus | ||
DPPH | 1.48 ± 1.82 TE mM/g | fructus | ||
ABTS | 0.92 ± 2.08 TE mM/g | fructus | ||
FRAP | 0.38 ± 1.98 FeII mM/g | fructus | ||
TPC | 31.60 ± 0.35 mg GAE/g | fructus | Maceration and UAE | [15] |
TFC | 15.38 ± 0.02 mg RE/g | |||
DPPH | EC50 78.00% μg/mL | |||
DPPH | 47.45% (3.2 mg/mL) | fructus | Maceration in 95% ethanol and 0.3 mol/L of NaOH solution overnight | [61] |
ABTS | 49.58% (3.2 mg/mL) | |||
DPPH | 90.24% at 1.0 mg/mL | fructus | CPE | [41] |
ORAC | 928.64 µmol TE/g | |||
Hydroxyl RSA | 81.5% at 0.8 mg/mL | fructus | Digestion | [45] |
Superoxide anion radical scavenging activity | 7.7 to 73.5% at 0.05 to 0.8 mg/mL | |||
TPC | 25.8 ± 2.8 mg GAE/g of DW | by-products | Maceration 96% EtOH | [68] |
DPPH | 43.8 ± 0.3% | |||
Antimicrobial, antiviral and antifungal activity | ||||
MTT | 95% inhibition at 0.5 µg/µL on Madin Darby canine kidney (MDCK) cell line with Avian influenza A virus (H5N1 | EO | Hydro-distillation | [69] |
Agar diffusion assay | MIC: C. albicans 3 µg/mL, B. subtilis 25 µg/mL, K. pneumonia 25 µg/mL | fructus | Hydro-distillation | [41] |
Inibition zone (mm): B. subtilis 13, B. cereus 21, S. aureus 12, K. pneumonia 15, C. albicans 27, A. niger 11 | leaves | |||
Plaque reduction assay | 50% at 0.504 µg/µl | fructus | ||
95% at 0.5 µg/µl | leaves | |||
Plate count analysis | Saccharomyces cerevisiae: 3 min at 500 ppm | fructus | Hydro-distillation | [44] |
Plate count analysis | Bacteria survival: E. coli (600 ppm) 1 log decrease at day 3, S. Enteritidis (600 ppm) 3 log decrease at day 3, L. monocytogenes (600 ppm) 4 log decrease at day 3 | fructus | Hydro-distillation | [70] |
Disc diffusion test | Inibition zone (mm): mold growth on bread from 8.54 ± 1.27 mm to 15.26 ± 2.16 mm | flower and fructus | Hydro-distillation | [71] |
Inibition zone (mm): mold growth on bread > 90 mm | leaves | Hydro-distillation | ||
Agar diffusion assay | MIC (µL/mL): Lactobacillus curvatus, Weissella viridescens, Leuconostoc mesenteroides, Enterococcus faecium, Lactobacillus reuteri, Lactobacillus dextrinicus, Lactobacillus sakei, and Pediococcus dextrinicus from 7.33 ± 0.57 to 9.00 ± 0.00 | fructus | Hydro-distillation | [72] |
Agar diffusion assay | MIC (mg/mL): Gram-positive from 0.625 to 1.25; Gram-negative bacteria 2.5 | fructus | Hydro-distillation | [73] |
Plate count analysis | MIC (mg/mL): Gluconobacter cerinus, Dekkera bruxellensis, Candida zemplinina, Hanseniaspora uvarum, Pichia guilliermondii, and Zygosaccharomyces bailii from 530 to 4240 | fructus | Hydro-distillation | [74] |
Oxford cup method | MIC (mg/mL): Fusarium oxysporum 9.38, Fusarium solani 12.05, and Cylindrocarpon destructans 8.44 | fructus | Hydro-distillation | [75] |
Plate count analysis | Yersinia enterocolitica O9, Proteus spp., Klebsiella pneumoniae, and E. coli: not effective | aerial parts | Hydro-distillation | [76] |
Agar diffusion assay | MIC (mg/L): Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Listeria monocytogenes, Salmonella Enteritidis, Salmonella Typhimurium, Pseudomonas fragi, Saccharomyces cerevisiae, and Aspergillus niger < 2000 | fructus | Hydro-distillation | [77] |
Agar diffusion assay | MIC (v/v%): Escherichia coli, Pseudomonas Aeruginosa, Salmonella paratyphi B, Listeria monocytogenes, Staphylococcus aureus, Bacillus subtilis, Candida albicans, and Aspergillus flavus from 1 and 4% v/v | peel | Hydro-distillation | [46] |
Biofilm formation | Inhibition of biofilm formation (%): Staphylococcus aureus 100% at 0.75 mg/mL | fructus | Ultrasonic/microwave assisted hydro-distillation | [78] |
Inhibition of biofilm formation (%): Staphylococcus aureus 83l% at 0.75 mg/mL | Maceration | |||
Agar diffusion assay | Gold fingered citron MIC (mg/mL): Bacillus subtilis, Streptococcus pneumoniae, Enterococcus faecalis, Escherichia coli, and Staphylococcus aureus from 0.00 to 10.82 ± 02 | fructus | ultrasonic | [79] |
Cantonese fingered citron MIC (mg/mL): Bacillus subtilis, Streptococcus pneumoniae, Enterococcus faecalis, Escherichia coli, and Staphylococcus aureus from 0.00 to 9.81 ± 0.20 | ||||
Sichuan fingered citron MIC (mg/mL): Bacillus subtilis, Streptococcus pneumoniae, Enterococcus faecalis, Escherichia coli, and Staphylococcus aureus from 0.00 to 10.83 ± 0.24 | ||||
Agar diffusion assay | Sulphur nanoparticles MIC (µg/mL): Listeria monocytogenes, Salmonella typhi, Chromobacterium violaceum, Fusarium oxysporum, and Aspergillus flavus from 250 ± 1.21 to 700 ± 1.88 | leaves | Hydro-distillation | [80] |
Aluminium oxide nanoparticles MIC (µg/mL): Listeria monocytogenes, Salmonella typhi, Chromobacterium violaceum, Fusarium oxysporum, and Aspergillus flavus from 150 ± 2.77 to 1000 ± 1.1 | ||||
Tetrazolium microplate Assay | Nanoemulsions MIC (μL/mL): Escherichia coli, Bacillus subtilis, and Staphylococcus aureus from 0.16 to >2.5 | commercial EO | Commercial EO | [81] |
Mycelial growth assay | Nanoemulsions mycelial growth inhibition (%): Penicillium citrinum and Aspergillus niger from 3.6 ± 0.6 to 27.0 ± 1.1 | |||
Agar diffusion assay | ZnO nanoparticles inhibition zone (mm): Streptomyces sannanesis, Bacillus subtilis, Pseudomonas aeruginosa, Salmonella enterica, Candida albicans, and Aspergillus niger from 22 to 25 | peel | Maceration | [82] |
Agar diffusion assay | Ethyl acetate and ethanolic extract MIC (mg/mL): Staphylococcus auricularis not active, Streptococcus mitis not active, Streptococcus pneumoniae not active, Klebsiella pneumoniae, and Escherichia coli from 12.5 to 25. | peel | Reflex extraction | [83] |
MIC (mg/mL): Staphylococcus auricularis, Streptococcus mitis, Streptococcus pneumoniae, and Klebsiella pneumoniae from 1.5625 to 6.25; Escherichia coli not active | juice | Hand squeezing | ||
Agar diffusion assay | Zone of inhibition (mm): Bacillus subtilis, Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Proteus vulgaris, Aspergillus flavus, A. niger, and Candida albicans from 0 to 23 | root, leaf, bark, peel, pulp | Maceration | [84] |
juice | Hand squeezing | |||
Agar diffusion assay | Bacillus subtilis, Staphylococcus aureus, and Escherichia coli; Klebsiella pneumonia not active | juice | Hand squeezing | [85] |
Pour plate | (At 2.0 mg/mL) MIC: P. aeruginosa 82.8%, S. aureus 100% | fructus | Maceration | [21] |
Microtiter-plate | E. coli, L. monocytegenes, P. carotovorum, Ps. aeruginosa, and S. aureus MIC (mg/mL): 7–10 | peel | Maceration | [34] |
pulp | ||||
Adherence and invasion in HeLA cells | Adherence (50.8 to 91%), invasion (85.1 to 94.8%) in C. jejuni strain | by-products | Maceration | [68] |
Motility | Inhibition C. jejuni: 35–50% | peles, seeds, bagasse | Maceration | [86] |
Biofilm formation | Inhibition C. jejuni: 60–75%, | |||
Disk diffusion | E. coli, K. pneumoniae, P. aeruginosa, Propionibacterium acnes, Salmonella typhi, and fungi Fusarium culmorum, F. oxysporum, and F. graminearum; zone of inhibition:10–30 mm | fructus | Squeezing | [87] |
Crystal violet staining | MIC = 1.25% (v/v) | fructus | Carbon-quantum-dots synthesis | [88] |
Cytotoxic activity | ||||
MTT | Growth inhibition 56.5 ± 3.6% 50 µg/mL | peel | Hydro-distillation | [89] |
Growth inhibition 30.2 ± 2.2% and 73.3 ± 2.6% cell death at 25 and 50 μg/mL | [90] | |||
EC50 1.24 ± 0.42 EO EC50 2.97 ± 0.07 Hy | fructus | [54] | ||
EC50 1.76 ± 0.32 | exocarp | Maceration and UAE | [54] | |
50% growth inhibition at 7.80 and 9.50 μmol/L | peel | Semisynthesis | [91] | |
IC50 from 60.5 to 80.0 μM | bark | Maceration | [37] | |
Anti-inflammatory and analgesic activity | ||||
NO | 56% after 12 h, 83% after 24 h at 0.063 mg/mL | fructus | Hydro-distillation | [77] |
IC50 17.0 mg/mL | peel | [92] | ||
10.87–82.77% at 500 mg (60–300 min) | [24] | |||
250–500 mg at 30–120 min | ||||
Clinical study | > than placebo in reduction in headache-attack intensity | juice | Syrup | [10] |
Hypoglycemic activity | ||||
α-amylase | IC50 625 ± 8.53 µg/mL | peel | Maceration | [50] |
>1000 IC50 µg/mL | flowers | [27] | ||
438.5 ± 5.2 IC50 µg/mL | leaves | |||
702.2 ± 5.7 IC50 µg/mL | immature mesocarp | |||
702.2 ± 5.7 IC50 µg/mL | immature endocarp | |||
707.4 ± 5.6 IC50 µg/mL | mature mesocarp | |||
426.0 ± 4.4 IC50 µg/mL | mature endocarp | |||
α -glucosidase | >1000 IC50 µg/mL | flowers | ||
777.8 ± 5.4 IC50 µg/mL | leaves | |||
539.7 ± 6.4 IC50 µg/mL | immature mesocarp | |||
472.9 ± 4.7 IC50 µg/mL | immature endocarp | |||
633.1 ± 3.4 IC50 µg/mL | mature mesocarp | |||
574.1 ± 5.8 IC50 µg/mL | mature endocarp | |||
Plasma glucose level | Glucose (mg/dL): from 213 (60 min) to 155 (120 min) | epicarp | Hydro-distillation | [53] |
Glucose (mg/dL): from 228 (60 min) to 216(120 min) | pulp | |||
From glucose level (mg/dL) 106.8 ± 5.87 to 105.2 ± 8.35 (after 1 month) at 200 mg/kg/day; from glucose level (mg/dL) 109.3 ± 5.04 to 87.4 ± 6.30 (after 1 month) at 400 mg/kg/day | leaves | Maceration | [38] |
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Benedetto, N.; Carlucci, V.; Faraone, I.; Lela, L.; Ponticelli, M.; Russo, D.; Mangieri, C.; Tzvetkov, N.T.; Milella, L. An Insight into Citrus medica Linn.: A Systematic Review on Phytochemical Profile and Biological Activities. Plants 2023, 12, 2267. https://doi.org/10.3390/plants12122267
Benedetto N, Carlucci V, Faraone I, Lela L, Ponticelli M, Russo D, Mangieri C, Tzvetkov NT, Milella L. An Insight into Citrus medica Linn.: A Systematic Review on Phytochemical Profile and Biological Activities. Plants. 2023; 12(12):2267. https://doi.org/10.3390/plants12122267
Chicago/Turabian StyleBenedetto, Nadia, Vittorio Carlucci, Immacolata Faraone, Ludovica Lela, Maria Ponticelli, Daniela Russo, Claudia Mangieri, Nikolay T. Tzvetkov, and Luigi Milella. 2023. "An Insight into Citrus medica Linn.: A Systematic Review on Phytochemical Profile and Biological Activities" Plants 12, no. 12: 2267. https://doi.org/10.3390/plants12122267