In Search of High-Yielding and Single-Compound-Yielding Plants: New Sources of Pharmaceutically Important Saponins from the Primulaceae Family
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals
2.2. Plant Material
2.3. Preparation of Samples
2.4. Preparation of Standards
2.5. General NMR and HRMS Experimental Procedures
2.6. Purity of Standards
2.7. LC-MS Analytical Conditions
2.8. Validation of the Analytical Method
2.8.1. Specificity
2.8.2. Linearity, Range and Limits of Analysis
2.8.3. Precision, Accuracy and Stability
2.9. Clustering of Saponin Concentrations
3. Results
3.1. Method Development
3.2. Distribution of Saponins
3.2.1. Distribution of Primulasaponins
3.2.2. Distribution of Sakurasosaponin
3.2.3. Results of Clustering Analysis
4. Discussion
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
List of Abbreviations
[M–H]− | Pseudomolecular Ion (deprotonated molecule) |
2D | Two Dimensional (experiment in NMR) |
A. | Androsace |
APCI | Atmospheric-Pressure Chemical Ionization |
COSY | 1H-1H Correlated Spectroscopy (experiment in NMR) |
ELSD | Evaporative Light Scattering Detector |
ESI | Electrospray Ionization |
EU | European Union |
H. | Hottonia |
HCOOH | Formic Acid |
HMBC | Heteronuclear Multiple Bond Correlation (experiment in NMR) |
HRMS | High-Resolution Mass Spectrometry |
HSQC | Heteronuclear Single Quantum Correlation (experiment in NMR) |
LOD | Limit of Detection |
LOQ | Limit of Quantification |
LC | Liquid Chromatography |
LC-MS | Liquid Chromatography coupled with Mass Spectrometry Detector |
LC-UV | Liquid Chromatography coupled with Ultraviolet Absorbance Detector |
MeOH | Methanol |
MS/MS | Tandem Mass Spectrometry |
NMR | Nuclear Magnetic Resonance (Spectroscopy) |
P. | Primula |
PSI | Primulasaponin I |
PSII | Primulasaponin II |
qHNMR | Quantitative Proton Nuclear Magnetic Resonance (Spectroscopy) |
r | Coefficient of Correlation |
r2 | Coefficient of Determination |
RE | Relative Error |
RSD | Relative Standard Deviation |
sct. | Section |
SD | Standard Deviation |
sg. | Subgenus |
SPE | Solid-Phase Extraction |
ssct. | Subsection |
ssp. | Subspecies |
SSI | Sakurasosaponin |
TLC | Thin-Layer Chromatography |
UAE | Ultrasound-Assisted Extraction |
UHPLC | Ultra-High-Performance Liquid Chromatography |
var. | variety |
Appendix A
Taxon (a) | Acronym | Taxon (b) | Acronym |
genus Primula L. | sg. Aleuritia, sct. Minutissimae | ||
sg. Aleuritia, sct. Aleuritia, ssct. Aleuritia | Primula primulina | PPRI_P_2014 | |
Primula halleri | PHAL_P_2013, PHAL_K_2016 | sg. Aleuritia, sct. Muscarioides | |
Primula scandinavica | PSCA_B_2013 | Primula concholoba | PCON_K_2014 |
Primula scotica | PSCO_K_2016 | Primula muscarioides | PMUS_P_2013 |
sg. Aleuritia, sct. Aleuritia, ssct. Algida | Primula vialii | PVIA_B_2013 | |
Primula algida | PALG_K_2014 | sg. Aleuritia, sct. Oreophlomis | |
Primula darialica | PDAR_K_2014 | Primula auriculata | PAUA_K_2015 |
sg. Aleuritia, sct. Armerina | Primula luteola | PLUT_K_2015 | |
Primula fasciculata | PFAS_K_2014 | Primula rosea ‘Gigas’ | PROG_B_2013 |
Primula involucrata | PINV_P_2015 | Primula warschenewskiana | PWAR_K_2014 |
Primula munroi ssp. yargongensis (->P. involucrata in [1]) | PMUY_P_2015 | sg. Aleuritia, sct. Petiolares, ssct. Edgeworthii | |
Primula yargongensis (->P. involucrata in [1]) | PYAR_P_2015 | Primula moupinensis | PMOU_GP_2014 |
Primula zambalensis | PZAM_K_2014 | Primula moupinensis ssp. barkamensis | PMOB_K_2015 |
sg. Aleuritia, sct. Capitatae | sg. Aleuritia, sct. Petiolares, ssct. Griffithii | ||
Primula capitata ssp. mooreana | PCAM_B_2013 | Primula calderiana ssp. calderiana | PCAL_K_2014 |
Primula glomerata | PGLO_K_2014 | Primula tanneri ssp. nepalensis | PTNN_K_2014 |
sg. Aleuritia, sct. Crystalophlomis | sg. Aleuritia, sct. Petiolares, ssct. Petiolares | ||
Primula purdomii | PPUR_P_2014 | Primula boothi var. repens | PBOR_K_2014 |
sg. Aleuritia, sct. Crystalophlomis, ssct. Crystalophlomis | sg. Aleuritia, sct. Petiolares, ssct. Sonchifolia | ||
Primula chionantha | PCHI_K_2014 | Primula sonchifolia ssp. sonchifolia | PSON_K_2014 |
Primula chionantha ssp. chionantha | PCHC_K_2015 | sg. Aleuritia, sct. Proliferae | |
Primula chionantha ssp. sinopurpurea | PCHS_K_2015 | Primula beesiana | PBES_B_2013 |
Primula graminifolia (->P. chionantha in [1]) | PGRM_P_2015 | Primula bulleyana | PBUL_B_2013 |
Primula longipetiolata | PLON_K_2014 | Primula japonica | PJAP_B_2013 |
Primula macrophylla | PMAC_K_2015 | Primula prolifera | PPRO_K_2015 |
Primula orbicularis | PORB_K_2015, PORB_P_2015 | Primula wilsonii var. anisodora | PWIA_K_2015 |
sg. Aleuritia, sct. Crystalophlomis, ssct. Maximowiczii | sg. Aleuritia, sct. Pulchella | ||
Primula maximowiczii var. maximowiczii | PMAX_K_2014 | Primula pulchella | PPUL_K_2015, PPUL_P_2015 |
Primula tangutica | PTAN_P_2013 | Primula sharmae | PSHA_K_2016 |
Primula woodwardii | PWOD_P_2013, PWOD_P_2014 | Primula stenocalyx | PSTE_P_2013, PSTE_P_2014 |
sg. Aleuritia, sct. Davidii | sg. Aleuritia, sct. Sikkimensis | ||
Primula bergenioides | PBER_K_2015 | Primula firmipes | PFIR_K_2014 |
Primula ovaliifolia | POVA_K_2015 | Primula florindae | PFLO_B_2013 |
sg. Aleuritia, sct. Denticulata | Primula florindae, red flowered | PFLR_K_2015 | |
Primula denticulata ‘Alba’ | PDEA_B_2013 | Primula ioessa | PIOE_P_2013 |
Primula denticulata | PDEN_K_2016 | Primula sikkimensis | PSIK_K_2014 |
Primula monticola | PMON_K_2014, PMON_K_2015 | Primula waltonii | PWAL_K_2014 |
Taxon (c) | Acronym | Taxon (d) | Acronym |
sg. Aleuritia, sct. Soldanelloides | sg. Auriculastrum, sct. Auricula, ssct. Erythrodosum | ||
Primula reidii | PREI_K_2016 | Primula daoensis | PDAO_K_2014 |
Primula reidii var. williamsii ‘Alba’ | PREW_F_2015 | Primula hirsuta | PHIR_P_2013 |
sg. Aleuritia, sct. Yunnanensis | sg. Auriculastrum, sct. Auricula, ssct. Rhopsidium | ||
Primula florida (P. blinii) | PBLI_P_2013, PBLI_P_2014 | Primula allionii | PALL_F_2015 |
Primula rupicola | PRUP_K_2016 | Primula integrifolia | PINT_P_2013 |
sg. Auganthus, sct. Bullatae | Primula tyrolensis | PTYR_TK_2015 | |
Primula bullata var. rufa | PBUR_K_2014 | sg. Auriculastrum, sct. Auricula, hybrids | |
Primula forrestii | PFOR_K_2014 | Primula venusta | PVEN_B_2013 |
sg. Auganthus, sct. Cortusoides, ssct. Cortusoides | Primula allioni × Primula villosa | PXAV_P_2013 | |
Primula cortusoides | PCOR_B_2013 | sg. Auriculastrum, sct. Cuneifolia | |
Primula polyneura | PPOL_K_2015 | Primula cuneifolia | PCUN_K_2016 |
Primula sieboldii | PSIE_K_2014 | Primula cuneifolia ssp. heterodonta | PCUH_K_2016 |
sg. Auganthus, sct. Cortusoides, ssct. Geraniifolia | sg. Auriculastrum, sct. Dodecatheon | ||
Primula heucheriifolia | PHEU_K_2015 | Primula austrofrigida | PAUS_K_2014 |
Primula jesoana | PJES_K_2014 | Primula clevelandii | PCLE_K_2016 |
Primula kisoana | PKIS_K_2015 | Primula conjugens | PCJG_K_2014 |
Primula palmata | PPAL_K_2014 | Primula jeffreyi | PJEF_K_2015, PJEF_K_2016 |
sg. Auganthus, sct. Obconicolisteri | Primula latiloba | PLLB_K_2014 | |
Primula obconica | POBC_K_2014 | Primula meadia | PMEA_K_2014 |
sg. Auganthus, sct. Reinii | Primula pauciflora | PPAU_K_2014 | |
Primula takedana | PTAK_E_2014 | Primula tetrandra | PTET_K_2014 |
sg. Auriculastrum, sct. Amethystina | sg. Auriculastrum, sct. Parryi | ||
Primula amethystina var. brevifolia | PAMB_K_2015 | Primula angustifolia | PANG_K_2016 |
sg. Auriculastrum, sct. Auricula, ssct. Arthritica | Primula parryi | PPAR_K_2014 | |
Primula glaucescens ssp. longobarda | PGLL_P_2013, PGLL_P_2014 | Primula rusbyi | PRUS_K_2014 |
Primula spectabilis | PSPE_P_2013 | sg. Primula, sct. Primula | |
sg. Auriculastrum, sct. Auricula, ssct. Auricula | Primula elatior | PELA_K_2014 | |
Primula auricula | PAUR_B_2013 | Primula elatior var. amoena | PAMO_P_2014 |
sg. Auriculastrum, sct. Auricula, ssct. Brevibracteatum | Primula juliae | PJUL_B_2013 | |
Primula carniolica | PCAR_K_2014, PCAR_K_2015 | Primula megaseifolia | PMEG_K_2015 |
Primula latifolia ‘Alba’ | PLAA_P_2013 | Primula veris (syn. P. officinalis) | PVRS_K_2014 |
Primula marginata | PMGN_P_2013 | Primula vulgaris | PVUL_K_2014 |
sg. Auriculastrum, sct. Auricula, ssct. Chamaecallis | sg. Primula, sct. Sredinskya | ||
Primula minima | PMIN_I_2014 | Primula grandis | PGRA_K_2014, PGRA_K_2016 |
Primula minima f. niveum | PNIV_P_2014 | sg. Primula, hybrids | |
sg. Auriculastrum, sct. Auricula, ssct. Cyanaster | Primula margotae ‘Garryarde Guinevere’ | PMAG_B_2013 | |
Primula glutinosa | PGLU_P_2013 | sg. Sphondyllia | |
Primula × kewensis | PXKE_K_2016 | ||
Primula verticillata | PVRT_K_2014 | ||
Taxon (e) | Acronym | Taxon (f) | Acronym |
genus Androsace L. | sct. Aizodium | ||
sct. Andraspis | Androsace bulleyana | ABUL_F_2015 | |
Androsace albana | AALB_K_2019 | genus Cortusa L. | |
sct. Aretia, ssct. Aretia | Cortusa matthioli | CMAT_P_2013 | |
Androsace cylindrica | ACYL_K_2015 | Cortusa matthioli ssp. matthioli | CMAT_K_2015 |
Androsace lehmannii | ALEH_P_2014 | Cortusa matthioli ssp. caucasica | CCAU_K_2015, CCAU_K_2016 |
Androsace mathildae | AMTH_TK_2015 | Cortusa matthioli ssp. sachalinensis | CSAC_P_2013, CSAC_K_2015 |
sct. Aretia, ssct. Dicranothrix | Cortusa matthioli ssp. turkestanica | CTUR_P_2013 | |
Androsace lacteal | ALAC_TK_2015 | genus Dionysia Fenzl. | |
Androsace laggeri (= A. carnea var. laggeri) | ACAL_P_2014 | Dionysia khatamii | DKHA_F_2015 |
Androsace obtusifolia | AOBT_P_2014 | Dionysia zschummelii | DZSH_F_2015 |
sct. Chamaejasme, ssct. Hookerianae | genus Hottonia L. | ||
Androsace limprichtii | ALIM_P_2014 | Hottonia inflata hb | HOIN_MO_2014 |
sct. Chamaejasme, ssct. Mucronifoliae | Hottonia palustris hb | HOPA_PG_2014 | |
Androsace mariae var. tibetica | AMAT_P_2014 | genus Lysimachia L. | |
Androsace mucronifolia | AMUC_TK_2015 | Lysimachia nummularia ‘Gold’ | LYNG_PG_2014 |
Androsace sempervivoides | ASPV_B_2015 | Lysimachia thyrsiflora | LYTH_MO_2014 |
sct. Chamaejasme, ssct. Strigillosae | genus Omphalogramma (Franch.) Franch. | ||
Androsace spinulifera | ASPI_P_2015 | Omphalogramma delavayi | ODEL_PO_2019 |
Androsace strigillosa | ASTR_P_2014 | Omphalogramma tibeticum | OTIB_K_2019 |
sct. Chamaejasme, ssct. Sublanatae | genus Soldanella L. | ||
Androsace adenocephala | AADE_F_2015 | sct. Crateriflorae | |
Androsace nortonii | ANOR_P_2014 | Soldanella alpina | SALP_K_2016 |
sct. Chamaejasme, ssct. Villosae, series Chamaejasmoidae | Soldanella carpatica | SCAR_K_2014 | |
Androsace brachystegia | ABRA_P_2014 | Soldanella cyanaster | SCYA_K_2014 |
Androsace chamaejasme ssp. carinata | ACHC_P_2014 | Soldanella dimoniei | SDIM_K_2014 |
Androsace zambalensis | AZAM_P_2014 | Soldanella villosa | SVIL_K_2014 |
sct. Chamaejasme, ssct. Villosae, series Euvillosae | sct. Tubiflorae | ||
Androsace dasyphylla | ADAS_P_2014 | Soldanella minima | SMIN_F_2015, SMIN_TK_2015 |
Androsace robusta ssp. purpurea | AROP_P_2014 | genus Vitaliana Sesl. | |
Androsace sarmentosa | ASAR_K_2015 | Vitaliana primuliflora | VPRI_B_2015 |
sct. Pseudoprimula | Vitaliana primuliflora ssp. assoana | VPAS_TK_2015 | |
Androsace elatior | AELA_F_2015 | Vitaliana primuliflora ssp. praetutiana | VPPR_B_2015, VPPR_B_2017 |
sct. Douglasia | |||
Androsace montana (= Douglasia montana) | AMON_F_2015 |
Taxon (a) | Average % of Dry Mass | Taxon (b) | Average % of Dry Mass | Taxon (c) | Average % of Dry Mass | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
PSI | PSII | SSI | PSI | PSII | SSI | PSI | PSII | SSI | |||||
genus Primula | sg. Auganthus, sct. Bullatae | sg. Auriculastrum, sct. Cuneifolia | |||||||||||
sg. Aleuritia, sct. Armerina | P. bullata var. rufa | nd | nd | 1.07 | P. cuneifolia | Nd | nd | 2.31 | |||||
P. zambalensis | t | nd | 2.97 | P. forrestii | t | nd | 8.00 | P. cuneifolia ssp. heterodonta | Nd | nd | 3.28 | ||
sg. Aleuritia, sct. Crystallophlomis | sg. Auganthus, sct. Cortusoides | sg. Auriculastrum, sct. Dodecatheon | |||||||||||
P. chionantha | 5.57 | nd | nd | P. cortusoides | nd | nd | 4.37 | P. austrofrigida | T | nd | 2.62 | ||
P. chionantha ssp. chionantha | 6.35 | nd | nd | P. heucherifolia | t | nd | 2.24 | P. clevelandii | t | nd | 8.59 | ||
P. chionantha ssp. sinopurpurea | 4.31 | nd | nd | P. kisoana | t | nd | 1.68 | P. conjugens | 3.86 | nd | 1.26 | ||
P. graminifolia | 1.22 | nd | nd | P. palmata | t | nd | 2.13 | P. jeffreyi | 2.85 | nd | 1.00 | ||
P. longipetiolata | 9.48 | nd | nd | P. polyneura | t | nd | 2.22 | P. latiloba | t | nd | 0.77 | ||
P. macrophylla | 7.06 | nd | nd | P. sieboldii | t | nd | 4.20 | P. meadia | t | nd | 3.56 | ||
P. orbicularis | 0.60 | nd | nd | sg. Auganthus, sct. Obconicolisteri | P. pauciflora | t | nd | 5.08 | |||||
P. purdomii | t | nd | nd | P. obconica | t | nd | 8.59 | P. tetrandra | t | nd | 6.90 | ||
sg. Aleuritia, sct. Davidii | sg. Auganthus, sct. Reinii | sg. Auriculastrum, sct. Parryi | |||||||||||
P. bergenioides | 0.73 | nd | nd | P. takedana | t | nd | 9.09 | P. angustifolia | 0.35 | nd | 8.60 | ||
P. ovaliifolia | t | nd | nd | sg. Auriculastrum, sct. Auricula | P. parryi | 1.13 | nd | 0.44 | |||||
sg. Aleuritia, sct. Oreophlomis | P. allionii | t | nd | nd | P. rusbyi | t | nd | 0.85 | |||||
P. auriculata | 3.24 | nd | nd | P. allionii × P. villosa | t | nd | nd | sg. Primula, sct. Primula | |||||
P. luteola | 1.75 | nd | nd | P. auricula | t | nd | nd | P. elatior var. amoena | t | nd | nd | ||
P. rosea ‘Gigas’ | 4.06 | nd | nd | P. carniolica | t | nd | nd | P. elatior | 3.30 | nd | nd | ||
P. warschenewskiana | 5.21 | nd | nd | P. glaucescens ssp. longobarda | t | nd | 0.48 | P. elatior rhiz | 4.63 | nd | nd | ||
sg. Aleuritia, sct. Petiolares | P. glutinosa | t | nd | nd | P. juliae | 0.79 | t | nd | |||||
P. boothi var. repens | 1.04 | nd | nd | P. hirsuta | t | nd | nd | P. juliae rhiz | 0.21 | t | nd | ||
P. moupinensis | t | nd | nd | P. integrifolia | t | nd | nd | P. megaseifolia | 3.24 | 2.65 | nd | ||
P. moupinensis ssp. barkamensis | 1.17 | nd | nd | P. latifolia ‘Alba’ | t | nd | nd | P. veris (syn. P. officinalis) | 2.84 | t | nd | ||
P. sonchifolia ssp. sonchifolia | 0.67 | nd | nd | P. marginata | t | nd | nd | P. vulgaris | 6.23 | 3.26 | nd | ||
sg. Aleuritia, sct. Proliferae | P. minima | t | nd | nd | P. vulgaris rhiz | 3.30 | 2.27 | nd | |||||
P. besiana | t | nd | nd | P. minima f. niveum | t | nd | nd | sg. Primula, sct. Sredinskya | |||||
P. japonica ‘Alba’ | 1.05 | nd | nd | P. tyrolensis | t | nd | nd | P. grandis (PGRA_K_2014) | 23.88 | nd | nd | ||
P. prolifera | t | nd | nd | P. venusta | t | nd | nd | P. grandis (PGRA_K_2016) | 15.72 | nd | nd | ||
sg. Aleuritia, sct. Pulchella | P. grandis rhiz (PGRA_K_2016) | 14.57 | nd | nd | |||||||||
P. pulchella | t | nd | t |
Taxon (d) | Average % of Dry Mass | ||
---|---|---|---|
PSI | PSII | SSI | |
sg. Primula, hybrids | |||
P. margotae ‘GarryardeGuinevere’ | 4.80 | 0.32 | nd |
P. margotae rhiz | 2.21 | 0.23 | nd |
sg. Primula, trade samples | |||
Primulae radix 1 (PR1) | 8.60 | 4.90 | nd |
Primulae radix 2 (PR2) | 6.16 | t | nd |
Primulae radix 3 (PR3) | 2.66 | t | nd |
Primulae radix 4 (PR4) | 2.18 | t | nd |
sg. Sphondylia, hybrids | |||
P. × kewensis | 0.33 | nd | nd |
genus Androsace | |||
sct. Aretia | |||
A. lehmanii | nd | nd | 1.12 |
sct. Chamaejasme | |||
A. adenocephala | nd | nd | t |
A. brachystegia | nd | nd | t |
A. chamaejasme ssp. carinata | nd | nd | t |
A. limprichtii | nd | nd | 0.36 |
A. robusta ssp. purpurea | nd | nd | 0.76 |
A. sarmentosa | nd | nd | 1.28 |
A. strigillosa | t | nd | t |
genus Hottonia | |||
H. inflata hb | 0.36 | nd | 2.27 |
H. palustris hb | 0.31 | nd | 0.62 |
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Standard | n ± SD | A ± SD | B ± SD | r | r2 | LOD [ng/mL] | LOQ [ng/mL] |
---|---|---|---|---|---|---|---|
PSI | 0.890 ± 0.072 | 4,574,451 ± 83,044 | 24.73 ± 1.26 | 0.9998 | 0.9996 | 6.7 | 20.3 |
PSII | 0.776 ± 0.110 | 3,274,550 ± 100,794 | 23.41 ± 2.24 | 0.9994 | 0.9988 | 6.4 | 19.4 |
SSI | 0.943 ± 0.110 | 3,951,182 ± 86,066 | 20.29 ± 1.62 | 0.9995 | 0.9990 | 7.4 | 22.5 |
Standard | Repeatability (RSD)/(Intra-Day Precision) | Intermediate Precision (RSD)/(Inter-Day Precision) | ||||
Level | 1 µg/mL | 10 µg/mL | 100 µg/mL | 1 µg/mL | 10 µg/mL | 100 µg/mL |
PSI | 2.3 | 2.0 | 0.4 | 5.6 | 1.6 | 1.2 |
PSII | 4.0 | 1.7 | 0.7 | 6.1 | 1.5 | 1.1 |
SSI | 2.8 | 1.2 | 1.0 | 3.0 | 1.2 | 0.9 |
Standard | Accuracy (%RE) | Stability (RSD)/(14 days) | ||||
Level | 1 µg/mL | 10 µg/mL | 100 µg/mL | 1 µg/mL | 10 µg/mL | 100 µg/mL |
PSI | +21.2 | +3.5 | +0.1 | 3.2 | 3.3 | 2.6 |
PSII | +30.6 | +5.5 | −0.7 | 10.1 | 1.8 | 4.2 |
SSI | +15.4 | +4.8 | +0.4 | 6.8 | 2.2 | 1.4 |
Sample Acronym | Group | Sample Acronym | Group | Sample Acronym | Group | Sample Acronym | Group |
---|---|---|---|---|---|---|---|
PFOR_K_2014 | 1 | HOIN_MO_2014 | 2 | PCHS_K_2015 | 3 | PCHI_K_2014 | 6 |
POBC_K_2014 | 1 | PZAM_K_2014 | 2 | PAUA_K_2015 | 3 | PCHC_K_2015 | 6 |
PTAK_E_2014 | 1 | PCOR_B_2013 | 2 | PROG_B_2013 | 3 | PLON_K_2014 | 6 |
PCLE_K_2016 | 1 | PPOL_K_2015 | 2 | PCJG_K_2014 | 3 | PMAC_K_2015 | 6 |
PTET_K_2014 | 1 | PSIE_K_2014 | 2 | PJEF_K_2015 | 3 | PWAR_K_2014 | 6 |
PANG_K_2016 | 1 | PHEU_K_2015 | 2 | PELA_K_2014 | 3 | PR2 | 6 |
PPAL_K_2014 | 2 | PMEG_K_2015 | 3 | ||||
PCUN_K_2016 | 2 | PVRS_K_2014 | 3 | PVUL_K_2014 | 7 | ||
PCUH_K_2016 | 2 | PR3 | 3 | PR1 | 7 | ||
PAUS_K_2014 | 2 | PR4 | 3 | ||||
PMEA_K_2014 | 2 | PMAG_B_2013 | 3 | PGRA_K_2014 | 8 | ||
PPAU_K_2014 | 2 | PGRA_K_2016 | 8 |
Taxon | n | PSI | PSII | SSI | Taxon (Continuation) | n | PSI | PSII | SSI | Taxon (Continuation) | n | PSI | PSII | SSI |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
genus Primula L., sg. Aleuritia | genus Primula L., sg. Auganthus | genus Androsace L. | ||||||||||||
sct. Aleuritia, ssct. Aleuritia | 3 | sct. Bullatae | 2 | sct. Aizodium | 1 | |||||||||
sct. Aleuritia, ssct. Algida | 2 | sct. Cortusoides, ssct. Cortusoides | 3 | sct. Andraspis | 1 | |||||||||
sct. Armerina | 5 | sct. Cortusoides, ssct. Geraniifolia | 4 | sct. Aretia, ssct. Aretia | 3 | |||||||||
sct. Capitatae | 2 | sct. Obconicolisteri | 1 | sct. Aretia, ssct. Dicranothrix | 3 | |||||||||
sct. Crystalophlomis | 1 | sct. Reinii | 1 | sct. Chamaejasme, ssct. Hookerianae | 1 | |||||||||
sct. Crystalophlomis, ssct. Crystalophlomis | 7 | genus Primula L., sg. Auriculastrum | sct. Chamaejasme, ssct. Mucronifoliae | 3 | ||||||||||
sct. Crystalophlomis, ssct. Maximowiczii | 3 | sct. Amethystina | 1 | sct. Chamaejasme, ssct. Strigillosae | 2 | |||||||||
sct. Davidii | 2 | sct. Auricula, ssct. Arthritica | 2 | sct. Chamaejasme, ssct. Sublanatae | 2 | |||||||||
sct. Denticulata | 3 | sct. Auricula, ssct. Auricula | 1 | sct. Chamaejasme, ssct. Villosae | ||||||||||
sct. Minutissimae | 1 | sct. Auricula, ssct. Brevibracteatum | 3 | series Chamaejasmoidae | 3 | |||||||||
sct. Muscarioides | 3 | sct. Auricula, ssct. Chamaecallis | 2 | series Euvillosae | 3 | |||||||||
sct. Oreophlomis | 4 | sct. Auricula, ssct. Cyanaster | 1 | sct. Douglasia | 1 | |||||||||
sct. Petiolares, ssct. Edgeworthii | 2 | sct. Auricula, ssct. Erythrodosum | 2 | sct. Pseudoprimula | 1 | |||||||||
sct. Petiolares, ssct. Griffithii | 2 | sct. Auricula, ssct. Rhopsidium | 3 | |||||||||||
sct. Petiolares, ssct. Petiolares | 1 | sct. Auricula, hybrids | 2 | genus Cortusa L. | 6 | |||||||||
sct. Petiolares, ssct. Sonchifolia | 1 | sct. Cuneifolia | 2 | genus Dionysia Fenzl. | 2 | |||||||||
sct. Proliferae | 5 | sct. Dodecatheon | 8 | genus Hottonia L. | 2 | |||||||||
sct. Pulchella | 3 | sct. Parryi | 3 | genus Lysimachia L. | 2 | |||||||||
sct. Sikkimensis | 6 | genus Primula L., sg. Primula | genus Omphalogramma (Franch.) Franch. | 2 | ||||||||||
sct. Soldanelloides | 2 | sct. Primula | 6 | genus Soldanella L. | 6 | |||||||||
sct. Yunnanensis | 2 | sct. Sredinskya | 1 | genus Vitaliana Sesl. | 3 | |||||||||
genus Primula, sg. Sphondyllia | 2 | sct. Primula, hybrids | 1 |
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Włodarczyk, M.; Pasikowski, P.; Osiewała, K.; Frankiewicz, A.; Dryś, A.; Gleńsk, M. In Search of High-Yielding and Single-Compound-Yielding Plants: New Sources of Pharmaceutically Important Saponins from the Primulaceae Family. Biomolecules 2020, 10, 376. https://doi.org/10.3390/biom10030376
Włodarczyk M, Pasikowski P, Osiewała K, Frankiewicz A, Dryś A, Gleńsk M. In Search of High-Yielding and Single-Compound-Yielding Plants: New Sources of Pharmaceutically Important Saponins from the Primulaceae Family. Biomolecules. 2020; 10(3):376. https://doi.org/10.3390/biom10030376
Chicago/Turabian StyleWłodarczyk, Maciej, Paweł Pasikowski, Kinga Osiewała, Aleksandra Frankiewicz, Andrzej Dryś, and Michał Gleńsk. 2020. "In Search of High-Yielding and Single-Compound-Yielding Plants: New Sources of Pharmaceutically Important Saponins from the Primulaceae Family" Biomolecules 10, no. 3: 376. https://doi.org/10.3390/biom10030376
APA StyleWłodarczyk, M., Pasikowski, P., Osiewała, K., Frankiewicz, A., Dryś, A., & Gleńsk, M. (2020). In Search of High-Yielding and Single-Compound-Yielding Plants: New Sources of Pharmaceutically Important Saponins from the Primulaceae Family. Biomolecules, 10(3), 376. https://doi.org/10.3390/biom10030376