Identification of Floral Scent Profiles in Bearded Irises
Abstract
:1. Introduction
2. Results and Discussion
2.1. Identification of Floral Scent Components in Bearded Iris Accessions
2.2. Principle Components Analysis of Floral Scent Components in Bearded Irises
2.3. Hierarchical Cluster Analysis of Floral Scent Components in Bearded Irises
3. Materials and Methods
3.1. Plant Materials
3.2. Sample Collection
3.3. HS-SPME Analysis
3.4. GC-MS Analysis
3.5. Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Acknowledgments
Conflicts of Interest
References
- Schiestl, F.P. The Evolution of Floral Scent and Insect Chemical Communication. Ecol. Lett. 2010, 13, 643–656. [Google Scholar] [CrossRef] [PubMed]
- Xiang, L.; Chen, L. Adavances in Genetic Engineering of Floral Scent. Sci. Agric. Sin. 2009, 42, 2076–2084. [Google Scholar]
- Zhang, Y.; Li, X.; Wang, Y.; Tian, M.; Fan, M. Changes of Aroma Components in Oncidium Sharry Baby in Different Florescence and Flower Parts. Sci. Agric. Sin. 2011, 44, 110–117. [Google Scholar]
- Dormont, L.; Delle-Vedove, R.; Bessière, J.-M.; Schatza, B. Floral Scent Emitted by White and Coloured Morphs in Orchids. Phytochemistry 2014, 100, 51–59. [Google Scholar] [CrossRef] [PubMed]
- Cao, H.; Li, Z.; Shen, D. GC/MS Fingerprint Analysis of Osmanthus fragrans Lour. in Different Varieties. Acta Hortic. Sin. 2009, 36, 391–398. [Google Scholar]
- Li, S.; Chen, L.; Xu, Y.; Wang, L.; Wang, L. Identification of Floral Fragrances in Tree Peony Cultivars by Gas Chromatography-Mass Spectrometry. Sci. Hortic. 2012, 142, 158–165. [Google Scholar] [CrossRef]
- Zhang, H.; Hu, Z.; Leng, P.; Wang, W.; Xu, F.; Zhao, J. Qualitative and Quantitative Analysis of Floral Volatile Components from Different Varieties of Lilium spp. Sci. Agric. Sin. 2013, 46, 790–799. [Google Scholar]
- Feng, L.-G.; Chen, C.; Sheng, L.-X.; Liu, P.; Tao, J.; Su, J.-L.; Zhao, L.-Y. Comparative Analysis of Headspace Volatiles of Chinese Rosa rugosa. Molecules 2010, 15, 8390–8399. [Google Scholar] [CrossRef] [PubMed]
- Karami, A.; Khosh-Khui, M.; Salehi, H.; Saharkhiz, M.J.; Rowshan, V. Headspace Analysis of Floral Scent from Two Distinct Genotypes of Iranian Damask Rose (Rosa damascena Mill.). J. Essent. Oil Bear. Plants 2013, 16, 489–498. [Google Scholar] [CrossRef]
- Zhao, Y.; Pan, H.; Zhang, Q.; Pan, C.; Cai, M. Dynamics of Fragrant Compounds from Prunus mume Flowers. J. Beijing Forest. Univ. 2010, 32, 201–206. [Google Scholar]
- Zhou, J.; Ni, D. Changes in Flower Aroma Compounds of Cultivars of Chimonanthus praecox (L.) Link and at Different Stages Relative to Chimonanthus Tea Quality. Acta Hortic. Sin. 2010, 37, 1621–1628. [Google Scholar]
- Li, Y.; Ma, H.; Wan, Y.; Li, T.; Liu, X.; Sun, Z.; Li, Z. Volatile Organic Compounds Emissions from Luculia pinceana Flower and Its Changes at Different Stages of Flower Development. Molecules 2016, 21, 531. [Google Scholar] [CrossRef] [PubMed]
- Liu, Q.; Sun, G.; Wang, S.; Lin, Q.; Zhang, J.; Li, X. Analysis of the Variation in Scent Components of Hosta Flowers by HS-SPME and GC-MS. Sci. Hortic. 2014, 175, 57–67. [Google Scholar] [CrossRef]
- Xu, W.; Cai, M.; Pan, H.; Zhang, Q. Study on Spatial-temporal Variability of Volatile Components in Lagerstroemia indica ‘Xiang Xue Yun’. J. Beijing For. Univ. 2017, 39, 85–95. [Google Scholar]
- Austin, C. Irises: A Gardener’s Encyclopedia; Timber Press: Portland, OR, USA, 2005; p. 23. [Google Scholar]
- Wang, G.; Li, D.; Zhang, J.; Xia, Y. Comparison of Cold Tolerance Within 6 Cultivars of Iris germanica. Acta Hortic. Sin. 2014, 41, 773–780. [Google Scholar]
- Meyer, C.J.; Peterson, C.A.; Steudle, E. Permeability of Iris germanica’s Multiseriate Exodermis to Water, NaCl, and Ethanol. J. Exp. Bot. 2011, 62, 1911–1926. [Google Scholar] [CrossRef] [PubMed]
- Guo, J.; Zhang, J.; Sun, G.; Shi, L. Effects of 6-BA Application on Promotion of Offset Formation in Iris germanica. Acta Hortic. Sin. 2007, 34, 461–464. [Google Scholar]
- Wang, Y.; Jeknic¢, Z.; Ernst, R.C.; Chen, T.H.H. Improved Plant Regeneration from Suspension-Cultured Cells of Iris germanica L. ‘Skating Party’. Hortscience 1999, 34, 1271–1276. [Google Scholar] [CrossRef]
- Hossein, A.M.; Somayyeh, J.; Rodrigo, B.G. Multivariate Analysis of Morphological Characteristics in Iris germanica Hybrids. Euphytica 2018, 214, 161. [Google Scholar]
- Huang, S.Z.; Han, Y.L.; Zhang, Y.G.; Guo, W.M. Breeding Dwarf Plants of Iris germanica L. through Hybridization. J. Nanjing Agric. Univ. 2003, 26, 21–25. [Google Scholar]
- Jeknic´, Z.; Jeknic´, S.; Jevremovic´, S.; Subotic´, A.; Chen, T.H.H. Alteration of Flower Color in Iris germanica L. ‘Fire Bride’ through Ectopic Expression of Phytoene Synthase Gene (crtB) from Pantoea agglomerans. Plant Cell Rep. 2014, 33, 1307–1321. [Google Scholar] [CrossRef] [PubMed]
- Li, F.; Bao, J.; Sun, Y.; Liu, C.; Ma, H.; Zhang, T.; Chen, X. Biological Effects of 60Co-γ Rays Irradiation on the Hybrid Seeds of Iris germanica. J. Nuclear Agric. Sci. 2017, 31, 1469–1474. [Google Scholar]
- Sun, H.; Zhang, T.; Fan, Q.; Qi, X.; Zhang, F.; Fang, W.; Jiang, J.; Chen, F.; Chen, S. Identification of Floral Scent in Chrysanthemum Cultivars and Wild Relatives by Gas Chromatography-Mass Spectrometry. Molecules 2015, 20, 5346–5359. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Dobson, H.E.M.; Arroyo, J.; Bergstrom, G.; Groth, I. Interspecific Variation in Floral Fragrances within the Genus Narcissus (Amaryllidaceae). Biochem. Syst. Ecol. 1997, 25, 685–706. [Google Scholar] [CrossRef]
- Jürgens, A. Flower Scent Composition in Diurnal Silene Species (Caryophyllaceae): Phylogenetic Constraints or Adaptation to Flower Visitors? Biochem. Syst. Ecol. 2004, 32, 841–859. [Google Scholar] [CrossRef]
- Majetic, C.J.; Levin, D.A.; Raguso, R.A. Divergence in Floral Scent Profiles among and within Cultivated Species of Phlox. Sci. Hortic. 2014, 172, 285–291. [Google Scholar] [CrossRef]
- Kukula-Koch, W.; Sieniawska, E.; Widelski, J.; Urjin, O.; Głowniak, P.; Skalicka-Woźniak, K. Major Secondary Metabolites of Iris spp. Phytochem. Rev. 2015, 14, 51–80. [Google Scholar] [CrossRef]
- Hacibekiroglu, I.; Kolak, U. Antioxidant and Anticholinesterase Constituents from the Petroleum Ether and Chloroform Extracts of Iris suaveolens. Phytother. Res. 2011, 25, 522–529. [Google Scholar] [CrossRef]
- Roger, B.; Jeannot, V.; Fernandez, X. Characterisation and Quantification of Flavonoids in Iris germanica L. and Iris pallida Lam. Resinoids from Morocco. Phytochem. Anal. 2012, 23, 450–455. [Google Scholar] [CrossRef]
- Basser, K.; Demirci, B.; Orhan, I.E.; Kartal, M.; Sekeroglu, N.; Sener, B. Composition of Volatiles from Three Iris Species of Turkey. J. Essent. Oil Res. 2011, 23, 66–71. [Google Scholar] [CrossRef]
- Mühlemann, J.K.; Klempien, A.; Dudareva, N. Floral Volatiles: From Biosynthesis to Function. Plant Cell Environ. 2014, 37, 1936–1949. [Google Scholar] [CrossRef]
- Azuma, H.; Thien, L.B.; Kawano, S. Molecular Phylogeny of Magnolia (Magnoliaceae) Inferred from cpDNA Sequences and Evolutionary Divergence of the Floral Scents. J. Plant Res. 1999, 112, 291–306. [Google Scholar] [CrossRef]
- Weiss, J.; Mühlemann, J.K.; Ruiz-Hernández, V.; Dudareva, N.; Egea-Cortines, M. Phenotypic Space and Variation of Floral Scent Profiles during Late Flower Development in Antirrhinum. Front. Plant Sci. 2016, 7, 1903. [Google Scholar] [CrossRef] [PubMed]
- Raguso, R.A.; Schlumpberger, B.O.; Kaczorowski, R.L.; Holtsford, T.P. Phylogenetic Fragrance Patterns in Nicotiana Sections Alatae and Suaveolentes. Phytochemistry 2006, 67, 1931–1942. [Google Scholar] [CrossRef] [PubMed]
- Liu, Q.; Sun, G.; Zhang, J.; Li, X. Study on Floral Scent of the Genus Hosta. Sci. Agric. Sin. 2015, 48, 4323–4334. [Google Scholar]
- Minh Tu, N.T.; Onishi, Y.; Choi, H.; Kondo, Y.; Bassore, S.M.; Ukeda, H.; Sawamura, M. Characteristic Odor Components of Citrus sphaerocarpa Tanaka (Kabosu) Cold-Pressed Peel Oil. J. Agric. Food Chem. 2002, 50, 2908–2913. [Google Scholar] [CrossRef]
- Dou, H. Study on the Change of the Main Biochemistry, Aroma Components, as well as Their Influence on the Flavor of Green Tea Beverages during Storage. Master’s Thesis, Huazhong Agricultural University, Wuhan, China, 2007. [Google Scholar]
- NIST Standard Reference Database. Available online: http://webbook.nist.gov/chemistry (accessed on 10 April 2019).
Sample Availability: Samples of the compounds are not available from the authors. |
Compound | Relative Content for Each Compound (%) | ||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 | 15 | 16 | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 | |
Methyl cinnamate | 34.16 | 0.20 | 7.71 | 0.34 | 13.54 | 23.59 | 1.67 | 10.48 | 0.22 | 0.92 | 2.43 | 0.23 | |||||||||||||||
Isosafrole | 21.27 | 0.15 | 6.26 | 14.01 | 1.16 | 0.14 | 0.67 | 0.92 | |||||||||||||||||||
Safrole | 5.94 | ||||||||||||||||||||||||||
Farnesol | 5.31 | 0.15 | 0.16 | 0.21 | 0.23 | 0.96 | 0.37 | 0.16 | |||||||||||||||||||
α-Longipinene | 3.24 | 0.13 | 0.91 | 7.40 | 0.75 | 0.15 | 0.14 | 0.25 | 1.29 | 0.19 | 0.11 | 1.09 | 1.09 | 2.51 | 2.86 | 0.44 | 0.23 | 1.23 | 0.17 | 4.66 | 3.34 | ||||||
Linalyl formate | 3.03 | 0.10 | 0.74 | ||||||||||||||||||||||||
Thujopsene | 2.45 | 1.90 | 18.33 | 1.70 | 0.11 | 0.31 | 0.53 | 0.51 | 10.11 | 2.30 | 1.57 | 0.18 | 21.92 | 5.95 | 3.82 | 0.22 | 0.31 | 0.37 | 0.25 | 5.36 | 0.24 | 1.18 | 17.58 | 0.85 | 4.44 | ||
Geranyl acetone | 1.59 | 0.21 | 0.18 | 0.30 | 0.16 | 0.55 | 1.91 | 0.29 | 0.14 | 0.23 | 0.12 | 0.65 | |||||||||||||||
α-Pinene | 1.56 | 3.51 | 5.70 | 0.42 | 0.46 | 0.48 | 0.81 | 2.19 | 1.69 | 0.83 | 11.10 | 1.15 | 11.97 | 1.23 | 4.02 | 1.03 | 0.61 | 10.71 | 3.69 | 2.76 | 0.46 | 0.24 | |||||
Limonene | 1.42 | 16.99 | 2.50 | 4.89 | 0.43 | 1.14 | 0.79 | 0.31 | 11.2 | 0.17 | 7.63 | 0.21 | 4.49 | 1.10 | 2.54 | 3.45 | 1.06 | 0.19 | 0.50 | ||||||||
Nerolidol | 1.23 | 0.60 | 1.57 | 0.31 | 0.13 | 18.15 | 2.78 | 12.63 | 11.07 | 0.38 | 0.61 | 0.61 | 0.19 | 0.10 | 0.60 | 0.62 | 22.52 | 1.46 | 0.56 | 1.61 | 1.72 | ||||||
Ttetrahydrogeraniol | 1.05 | 0.35 | 1.38 | 0.30 | 0.32 | 0.11 | 1.26 | 0.14 | 0.76 | 0.49 | 0.25 | 0.82 | 19.04 | 0.26 | 3.58 | 0.35 | 2.72 | 0.28 | 0.69 | 4.12 | 0.32 | ||||||
(-)-Verbenone | 0.93 | 0.19 | 0.53 | 0.46 | 0.24 | 1.70 | 0.12 | 0.96 | |||||||||||||||||||
Menthol | 0.82 | 0.10 | 0.76 | 0.17 | 0.58 | ||||||||||||||||||||||
Isolimonene | 0.72 | 1.29 | 0.11 | 2.22 | 1.84 | 0.44 | |||||||||||||||||||||
DL-Menthol | 0.67 | 0.17 | |||||||||||||||||||||||||
Isomenthol | 0.62 | 0.44 | 0.13 | ||||||||||||||||||||||||
Hexadecane | 0.59 | 0.15 | 0.21 | 0.65 | 0.47 | 0.43 | 0.14 | 0.18 | 0.13 | 0.21 | 0.10 | 0.79 | 0.22 | 0.26 | 0.33 | 0.39 | 0.16 | 0.18 | 0.26 | 0.74 | |||||||
Safranal | 0.55 | 1.29 | |||||||||||||||||||||||||
α-Phellandrene | 0.47 | 1.11 | 0.14 | 0.49 | 0.10 | 0.61 | 0.14 | 0.64 | 0.54 | ||||||||||||||||||
Butyl butyrate | 0.45 | 0.23 | |||||||||||||||||||||||||
Citronellyl acetate | 0.44 | 4.43 | 0.18 | 0.10 | 0.11 | 0.42 | 0.42 | 16.90 | |||||||||||||||||||
3-Methylheptane | 0.43 | 0.13 | 0.11 | 0.12 | |||||||||||||||||||||||
Farnesyl acetate | 0.36 | 0.23 | 0.11 | ||||||||||||||||||||||||
Pentadecane | 0.35 | 0.11 | 0.17 | 0.39 | 0.21 | 12.74 | 0.13 | 0.31 | 1.20 | 0.35 | 2.98 | 0.22 | 0.57 | 8.06 | 0.33 | 0.53 | 0.85 | 6.08 | 7.98 | 0.24 | 0.22 | 0.26 | 0.28 | 0.47 | 7.79 | ||
Butyl isobutyrate | 0.29 | 0.10 | |||||||||||||||||||||||||
Eugenol | 0.27 | 3.88 | 0.27 | ||||||||||||||||||||||||
Tridecane | 0.26 | 0.39 | 0.19 | 0.41 | 0.11 | 0.74 | 0.11 | 0.10 | 0.21 | 3.05 | 0.46 | 0.48 | 0.31 | ||||||||||||||
Cineole | 0.25 | 0.15 | 0.15 | 0.29 | 0.20 | 0.42 | 0.19 | 0.50 | 0.11 | 0.10 | |||||||||||||||||
1-Octanol | 0.23 | 0.14 | 0.33 | 2.41 | 1.16 | 0.13 | |||||||||||||||||||||
Tetradecane | 0.22 | 0.12 | 0.10 | 0.20 | 0.13 | 0.38 | 0.28 | 0.18 | 0.42 | 0.62 | |||||||||||||||||
1-Undecanol | 0.21 | 0.20 | 0.15 | 0.17 | 0.19 | 0.11 | 0.16 | 0.11 | |||||||||||||||||||
Methyl oleate | 0.21 | 0.20 | 0.42 | 0.24 | 2.50 | 0.19 | 0.11 | 0.86 | |||||||||||||||||||
Camphene | 0.21 | 0.42 | 0.14 | 0.15 | 0.70 | 1.28 | 0.50 | 2.56 | 0.15 | 1.35 | 0.83 | 0.88 | 0.26 | ||||||||||||||
trans-Dihydrocarveol | 0.21 | 0.19 | 3.96 | 0.31 | 0.23 | 5.10 | 0.61 | ||||||||||||||||||||
β-Pinene | 0.20 | 4.39 | 0.20 | 0.34 | 1.47 | 0.15 | 0.24 | 2.09 | 0.26 | 1.14 | 2.26 | 0.44 | 0.20 | 0.26 | 0.88 | 1.86 | |||||||||||
Undecane | 0.20 | 0.11 | 0.13 | 0.24 | 0.10 | 3.93 | 0.13 | 0.27 | |||||||||||||||||||
β-Terpineol | 0.17 | 0.17 | 0.33 | 3.78 | 0.13 | ||||||||||||||||||||||
Cedrol | 0.13 | 0.37 | 0.23 | 0.19 | 0.24 | 0.19 | 0.10 | 0.13 | 0.13 | ||||||||||||||||||
Myrcene | 0.13 | 4.38 | 0.75 | 0.29 | 0.31 | 0.30 | 0.34 | 1.08 | 1.38 | 2.08 | 0.76 | 0.37 | 0.91 | 0.80 | 2.87 | 0.11 | |||||||||||
Sabinene | 0.13 | 0.45 | 0.27 | 0.85 | 0.26 | 0.22 | |||||||||||||||||||||
Methyl octanoate | 0.12 | 0.35 | 0.10 | 0.14 | 0.59 | 1.10 | 0.18 | 0.12 | |||||||||||||||||||
Lauryl alcohol | 0.12 | 0.20 | 0.11 | 0.12 | 0.20 | 2.42 | 0.18 | 0.27 | 0.12 | 0.44 | 0.13 | 0.24 | 1.74 | 0.70 | 0.22 | 0.50 | 0.24 | 0.62 | 0.53 | 0.59 | 0.36 | 0.32 | |||||
Isoeugenol | 0.12 | 0.15 | |||||||||||||||||||||||||
Geranial | 0.12 | 0.50 | 0.44 | 1.99 | |||||||||||||||||||||||
Terpinyl acetate | 0.12 | 1.67 | 0.10 | 0.18 | 0.60 | 4.06 | 0.13 | ||||||||||||||||||||
7,8-Epoxy-α-ionone | 0.11 | 0.11 | |||||||||||||||||||||||||
Nonane | 0.10 | 0.10 | 0.15 | 0.11 | |||||||||||||||||||||||
Citronellyl propanoate | 0.10 | 2.58 | 1.25 | 0.31 | 2.63 | 0.17 | 0.43 | 0.11 | |||||||||||||||||||
3-Carene | 0.10 | 1.49 | 0.98 | 1.32 | 0.10 | 1.45 | 0.25 | 0.3 | 0.22 | 0.33 | 0.49 | 0.38 | 9.23 | 0.64 | |||||||||||||
l-Caryophyllene | 0.10 | 0.10 | 45.44 | 24.64 | 0.38 | 0.27 | 0.25 | 7.46 | 9.64 | 17.11 | 0.71 | 1.14 | 5.72 | 0.12 | 19.6 | 0.50 | 37.41 | 0.90 | 54.38 | 10.71 | |||||||
Butyl hydroxy anisole | 0.10 | 0.12 | |||||||||||||||||||||||||
Methyl myristate | 22.86 | 2.55 | 2.67 | 7.87 | 2.10 | 9.72 | 5.40 | 3.30 | 1.93 | 20.25 | 2.29 | 0.83 | 7.76 | 5.56 | 2.85 | 0.70 | |||||||||||
Anisic aldehyde | 5.30 | 0.24 | 1.44 | ||||||||||||||||||||||||
Isoprene | 3.30 | 0.13 | 0.12 | ||||||||||||||||||||||||
Linalool | 3.14 | 11.88 | 10.00 | 4.98 | 10.25 | 21.79 | 32.42 | 13.41 | 12.22 | 18.17 | 33.84 | 0.25 | 0.33 | 18.26 | 16.29 | 17.90 | 10.75 | 18.68 | 34.61 | 4.37 | 0.12 | ||||||
4-Carene | 2.73 | 0.35 | 0.26 | 0.64 | 0.63 | 2.45 | 0.38 | ||||||||||||||||||||
Linalyl acetate | 1.92 | 0.19 | 4.20 | 4.78 | 6.31 | 1.50 | 1.74 | 0.69 | 9.42 | 11.16 | 8.66 | 8.79 | 7.33 | 21.99 | 0.10 | ||||||||||||
Geranyl phenylacetate | 1.89 | 0.83 | 0.24 | ||||||||||||||||||||||||
Ethyl chrysanthemumate | 1.67 | 1.98 | |||||||||||||||||||||||||
Alloaromadendrene | 1.54 | 1.19 | 2.80 | 1.95 | 0.87 | 2.66 | 1.53 | 5.58 | 0.39 | 11.75 | 1.20 | 5.21 | 0.13 | 0.38 | 5.50 | 5.64 | 5.47 | 0.65 | 0.16 | ||||||||
Methyl laurinate | 1.41 | 0.30 | 0.69 | 0.33 | 1.67 | 3.11 | 9.54 | 0.14 | 0.30 | 0.69 | |||||||||||||||||
Sativene | 1.33 | 1.08 | 0.19 | 2.02 | 0.20 | 0.76 | 0.53 | 0.13 | 0.46 | 0.69 | 7.80 | 1.63 | 0.58 | 1.64 | 0.41 | ||||||||||||
Methyl hexadecanoate | 1.03 | 0.91 | 0.60 | 6.95 | 1.57 | 5.51 | 3.78 | 1.30 | 6.01 | 23.18 | 12.03 | 0.24 | 3.44 | 6.77 | 0.85 | 5.64 | |||||||||||
Methyl undecanoate | 0.84 | 0.14 | 0.10 | 1.21 | 0.22 | 0.22 | 0.19 | 0.13 | 0.25 | 0.10 | 1.38 | ||||||||||||||||
β-Cyclocitral | 0.58 | 0.69 | |||||||||||||||||||||||||
α-Guaiene | 0.57 | 0.30 | 1.22 | 0.33 | 0.33 | 0.36 | 0.11 | 0.18 | 0.19 | 0.32 | 0.28 | 0.13 | |||||||||||||||
Ethylbenzene | 0.53 | 0.50 | 0.29 | 0.86 | 0.19 | ||||||||||||||||||||||
α-Terpinene | 0.46 | 0.16 | 0.23 | 0.17 | 0.21 | 0.22 | 0.10 | ||||||||||||||||||||
trans-Carveol | 0.32 | ||||||||||||||||||||||||||
α-Bulnesene | 0.30 | 0.96 | 0.80 | 1.55 | 0.63 | 2.49 | 0.31 | 2.57 | 0.45 | 0.10 | 0.52 | 1.32 | |||||||||||||||
(-)-4-Terpineol | 0.24 | 0.26 | 0.13 | 0.18 | 0.13 | 0.60 | 0.11 | 0.23 | 0.59 | 0.41 | 0.15 | 0.12 | |||||||||||||||
Calarene | 0.17 | 0.35 | 2.01 | 1.30 | 0.22 | 0.76 | 3.63 | 0.31 | 0.34 | ||||||||||||||||||
1-Decanol | 0.17 | 0.16 | 0.79 | 0.12 | 0.53 | ||||||||||||||||||||||
Valencene | 0.17 | 0.17 | 0.12 | 0.46 | 0.34 | 0.64 | 1.20 | 0.20 | 0.38 | 0.21 | 3.76 | 0.70 | 0.15 | ||||||||||||||
1-Methoxy-4-propylbenzene | 0.16 | ||||||||||||||||||||||||||
Isocyclocitral | 0.11 | 0.10 | |||||||||||||||||||||||||
Methyl 10-undecenoate | 0.11 | 0.16 | 0.24 | 0.50 | 0.57 | 0.30 | 0.47 | 0.24 | 0.13 | 0.24 | |||||||||||||||||
Geraniol | 22.64 | 5.70 | 0.25 | 0.63 | 1.91 | 2.11 | 2.87 | 1.99 | |||||||||||||||||||
2-Pentadecanone | 5.91 | ||||||||||||||||||||||||||
α-Caryophyllene | 4.82 | 0.41 | 0.67 | 0.12 | 1.03 | 0.14 | 0.28 | 16.7 | 0.18 | 1.63 | 0.11 | 3.95 | 0.34 | 0.71 | |||||||||||||
Nerol | 3.43 | 12.4 | 0.15 | 1.85 | 0.18 | 1.33 | 0.54 | 3.90 | 0.13 | 23.25 | 0.55 | 0.21 | |||||||||||||||
Geranyl butyrate | 1.03 | 0.13 | 1.42 | ||||||||||||||||||||||||
Neryl acetate | 0.87 | 0.28 | 1.92 | 1.39 | 2.40 | ||||||||||||||||||||||
2-Dodecanone | 0.76 | ||||||||||||||||||||||||||
Methyl caprate | 0.71 | 0.40 | 6.60 | 14.08 | 0.13 | 0.61 | 2.87 | ||||||||||||||||||||
Isopulegol | 0.62 | 0.10 | 0.12 | 0.37 | 0.66 | 0.13 | 0.70 | 0.80 | 0.16 | 0.33 | 0.69 | 1.07 | 0.33 | 0.22 | |||||||||||||
Phenylacetaldehyde | 0.58 | 0.17 | |||||||||||||||||||||||||
Methyl toluene | 0.47 | 0.15 | 0.39 | ||||||||||||||||||||||||
α-Terpineol | 0.40 | 0.46 | 0.83 | 0.62 | 0.63 | 1.09 | 0.95 | 0.36 | 0.64 | 0.81 | 1.19 | 0.36 | |||||||||||||||
Citronellyl formate | 0.37 | 0.12 | 0.16 | 0.17 | |||||||||||||||||||||||
Tridecanal | 0.36 | 0.11 | 0.36 | ||||||||||||||||||||||||
α-Santalol | 0.35 | 0.47 | 0.70 | 0.12 | 0.13 | 0.25 | 0.10 | 0.10 | |||||||||||||||||||
Citronellol | 0.27 | 33.64 | 0.55 | 0.26 | 2.14 | 25.58 | |||||||||||||||||||||
Diethyl carbonate | 0.26 | ||||||||||||||||||||||||||
cis-Citral | 0.20 | 0.12 | 0.87 | ||||||||||||||||||||||||
Tricyclene | 1.79 | 0.18 | 0.16 | 0.35 | 0.81 | 0.15 | 3.37 | 0.16 | |||||||||||||||||||
Linalool propionate | 0.18 | 0.27 | 0.13 | 0.11 | 0.10 | 5.10 | 2.27 | 0.16 | |||||||||||||||||||
Undecanal | 0.14 | 0.18 | 0.10 | 0.13 | |||||||||||||||||||||||
Cumin alcohol | 0.14 | ||||||||||||||||||||||||||
Tridecanol | 0.13 | 9.65 | 0.17 | 0.25 | 0.14 | 0.19 | 3.57 | 0.12 | 0.11 | ||||||||||||||||||
Aromadendrene | 0.12 | 0.26 | 0.84 | 1.22 | 1.40 | 0.57 | 0.34 | 0.12 | |||||||||||||||||||
Methyl benzoate | 0.11 | 0.11 | 0.65 | 0.14 | 0.15 | ||||||||||||||||||||||
Tetradecanal | 0.10 | 0.12 | 0.19 | 0.53 | 0.28 | 0.32 | 0.65 | 1.86 | 0.27 | 0.14 | 1.81 | 0.76 | 1.94 | 0.86 | 0.51 | 0.18 | |||||||||||
α-Bisabolene | 7.17 | 1.77 | 0.24 | 0.21 | 0.15 | 1.30 | 1.03 | 0.40 | 0.90 | 0.10 | 0.16 | 4.12 | |||||||||||||||
α-Copaene | 7.12 | 0.16 | 0.27 | 6.80 | 2.26 | 0.19 | |||||||||||||||||||||
Ketone | 2.34 | 0.17 | |||||||||||||||||||||||||
β-Cedrene | 1.53 | 29.36 | 5.56 | 0.13 | 16.94 | 9.89 | 19.29 | 13.89 | 3.41 | 12.92 | 11.07 | 1.63 | 8.66 | 7.10 | 3.20 | ||||||||||||
α-Cubebene | 1.05 | 0.81 | 1.15 | 0.65 | |||||||||||||||||||||||
α-Cedrene | 0.90 | 2.16 | 0.21 | 2.51 | 1.37 | 1.35 | 2.69 | 1.72 | 0.17 | 0.34 | 1.12 | 0.26 | 0.79 | 1.53 | 0.24 | ||||||||||||
α-Bisabolol | 0.79 | 0.39 | 0.18 | 0.12 | 0.27 | 0.17 | 0.12 | 1.54 | 0.10 | ||||||||||||||||||
δ-Cadinene | 0.68 | 0.10 | 0.19 | 0.29 | 10.64 | ||||||||||||||||||||||
Patchouli alcohol | 0.59 | 0.11 | |||||||||||||||||||||||||
Propylbenzene | 0.45 | 0.17 | 0.44 | ||||||||||||||||||||||||
α-Asarone | 0.42 | ||||||||||||||||||||||||||
Heptadecane | 0.36 | 0.41 | 7.68 | 0.18 | 0.19 | 0.11 | 0.16 | 0.13 | 1.05 | 0.22 | 0.28 | 0.10 | 0.42 | 0.38 | 0.17 | 0.5 | |||||||||||
Eugenol acetate | 0.35 | 0.19 | |||||||||||||||||||||||||
Piperonal | 0.35 | 0.10 | 0.33 | 0.10 | 0.10 | 0.16 | |||||||||||||||||||||
Viridiflorene | 0.28 | 3.11 | 0.32 | 1.84 | 0.12 | 0.21 | 0.18 | 11.76 | |||||||||||||||||||
2-Ethylhexanol | 0.27 | ||||||||||||||||||||||||||
β-Asarone | 0.18 | ||||||||||||||||||||||||||
Globulol | 0.17 | 8.07 | 0.12 | 0.60 | |||||||||||||||||||||||
α-Longifolene | 0.17 | 4.45 | 0.15 | 1.47 | 2.54 | 0.17 | 0.17 | 0.39 | 0.22 | 0.23 | 1.99 | 1.18 | 2.28 | ||||||||||||||
Caryophyllene oxide | 0.16 | 0.10 | 0.12 | 0.23 | 0.17 | 0.30 | 0.12 | ||||||||||||||||||||
β-Santalol | 0.16 | 0.37 | 0.13 | 0.17 | 0.26 | 0.17 | 0.18 | 0.34 | |||||||||||||||||||
γ-Gurjunene | 0.14 | 0.10 | 1.11 | 3.89 | 0.84 | 0.24 | 0.11 | 0.43 | 0.10 | 0.13 | |||||||||||||||||
1-Isoproyl-3-tert-butylbenzene | 0.13 | 0.25 | |||||||||||||||||||||||||
(-)-Aristolene | 0.11 | 0.23 | 1.26 | ||||||||||||||||||||||||
2-tert-Butyl-4-hydroxyanisole | 0.10 | ||||||||||||||||||||||||||
2-Isopropyl-5-ketohexanal | 0.10 | ||||||||||||||||||||||||||
β-Eudesmene | 2.67 | 0.15 | 0.34 | 0.16 | 0.17 | 0.11 | |||||||||||||||||||||
ρ-Diethylbenzene | 0.60 | 0.36 | 0.64 | 0.26 | |||||||||||||||||||||||
Benzyl formate | 0.36 | ||||||||||||||||||||||||||
Phenylethyl alcohol | 0.32 | 1.43 | 0.28 | 0.76 | |||||||||||||||||||||||
γ-Terpinene | 0.30 | 1.71 | 0.26 | 0.15 | 0.17 | ||||||||||||||||||||||
Phenylacetic acid | 0.22 | ||||||||||||||||||||||||||
Dolcymene | 0.17 | 0.26 | 0.18 | 3.88 | 0.11 | 1.71 | 0.34 | 0.26 | |||||||||||||||||||
Terpinolene | 0.15 | 0.11 | 1.12 | 0.91 | |||||||||||||||||||||||
2-Phenyl-1-propanal | 0.11 | 0.11 | 0.24 | 0.23 | |||||||||||||||||||||||
Isolongifolene | 0.10 | 0.16 | |||||||||||||||||||||||||
α-Thujone | 13.41 | 0.43 | 0.11 | 1.47 | 2.58 | 6.1 | |||||||||||||||||||||
2,2,4-Trimethylpentane | 2.71 | ||||||||||||||||||||||||||
Myristyl alcohol | 2.33 | 0.22 | 2.02 | 0.32 | 0.18 | 0.11 | 0.54 | 3.10 | 0.14 | ||||||||||||||||||
Cryptone | 2.26 | 2.64 | 0.36 | ||||||||||||||||||||||||
2,5-Dimethylhexane | 0.17 | 0.13 | 0.49 | 0.32 | 6.47 | 0.18 | 0.22 | 0.21 | |||||||||||||||||||
Dihydrocarvone | 0.16 | 0.12 | 0.13 | ||||||||||||||||||||||||
Methyl linoleate | 0.16 | 1.21 | 0.16 | 0.32 | |||||||||||||||||||||||
Methyl stearate | 0.13 | 0.74 | 0.30 | 0.35 | |||||||||||||||||||||||
Allyl hexanoate | 0.11 | 0.46 | 0.18 | ||||||||||||||||||||||||
2,4-Dimethylpentane | 0.10 | 0.10 | |||||||||||||||||||||||||
Cyclohexaneethanol | 5.45 | 1.68 | |||||||||||||||||||||||||
Methyl nonanoate | 2.00 | 0.34 | 1.39 | 0.11 | 0.19 | ||||||||||||||||||||||
Geranic acid | 1.06 | 0.37 | |||||||||||||||||||||||||
Menthol acetic ester | 0.85 | 0.34 | 0.24 | ||||||||||||||||||||||||
Citronellyl butyrate | 0.72 | 0.15 | 0.26 | ||||||||||||||||||||||||
Crotonaldehyde | 0.46 | ||||||||||||||||||||||||||
Carvomenthene | 0.19 | 0.10 | |||||||||||||||||||||||||
Methyl salicylate | 0.18 | ||||||||||||||||||||||||||
Benzyl benzoate | 0.12 | 0.14 | |||||||||||||||||||||||||
Benzoic aldehyde | 0.10 | ||||||||||||||||||||||||||
m-Isopropyl ethylbenzene | 0.97 | 0.34 | |||||||||||||||||||||||||
Cinnamaldehyde | 0.23 | 9.00 | 0.81 | ||||||||||||||||||||||||
m-Tolualdehyde | 0.22 | 0.48 | 4.36 | ||||||||||||||||||||||||
Amyl caprylate | 0.16 | 0.11 | |||||||||||||||||||||||||
Longicyclene | 0.16 | 0.14 | 0.11 | 1.38 | 0.23 | ||||||||||||||||||||||
Phenetole | 0.12 | ||||||||||||||||||||||||||
Fenchole | 13.59 | 0.86 | |||||||||||||||||||||||||
Pantolactone | 1.79 | 1.35 | 2.01 | 0.75 | |||||||||||||||||||||||
Methyl capronate | 0.14 | ||||||||||||||||||||||||||
Eicosane | 0.11 | 0.16 | 0.11 | 0.17 | 0.91 | ||||||||||||||||||||||
m-Diethylbenzene | 0.42 | 0.99 | 0.72 | ||||||||||||||||||||||||
1-Nonanol | 0.13 | 0.41 | |||||||||||||||||||||||||
o-Xylene | 0.13 | ||||||||||||||||||||||||||
Thymol | 0.12 | ||||||||||||||||||||||||||
Butyl caprylate | 0.10 | 0.12 | |||||||||||||||||||||||||
Geranyl tiglate | 2.31 | 1.49 | |||||||||||||||||||||||||
γ-Nonanolactone | 0.99 | 0.21 | 0.15 | 0.48 | 0.23 | 0.12 | 1.58 | ||||||||||||||||||||
γ-Decalactone | 0.90 | 0.26 | |||||||||||||||||||||||||
2,3,4-Trimethylpentane | 0.43 | 0.60 | 0.69 | 0.16 | |||||||||||||||||||||||
Tetrahydrofurfuryl acetate | 0.31 | 0.58 | 1.42 | ||||||||||||||||||||||||
Nootkanone | 0.13 | 0.15 | |||||||||||||||||||||||||
α-Cyclociral | 0.11 | 0.10 | |||||||||||||||||||||||||
Hydroquinone Dimethyl | 4.93 | 8.82 | 2.20 | ||||||||||||||||||||||||
Mesitylene | 0.45 | ||||||||||||||||||||||||||
Linalyl isovalerate | 0.36 | ||||||||||||||||||||||||||
Methyl acetate | 0.21 | ||||||||||||||||||||||||||
Methyl m-tolylketone | 0.20 | 0.84 | |||||||||||||||||||||||||
2,2,5-Trimethylhexane | 0.35 | 0.14 | |||||||||||||||||||||||||
Dodecane | 0.13 | 0.52 | 0.19 | ||||||||||||||||||||||||
Octyl formate | 0.33 | 0.27 | 0.20 | 0.36 | 0.23 | ||||||||||||||||||||||
Cyclohexane | 0.79 | 0.22 | |||||||||||||||||||||||||
2,6-Di-tert-butyl-p-cresol | 0.58 | 0.11 | 0.13 | 0.1 | |||||||||||||||||||||||
γ-Valerolactone | 0.42 | ||||||||||||||||||||||||||
6-Decalactone | 0.17 | 0.11 | |||||||||||||||||||||||||
Dihydro-α-ionone | 0.13 | ||||||||||||||||||||||||||
trans-2-Nonenal | 0.10 | ||||||||||||||||||||||||||
trans-2-Pinanol | 0.38 | 0.27 | |||||||||||||||||||||||||
2,2,4,4-Tetramethyl-3-pentanone | 0.20 | 0.27 | |||||||||||||||||||||||||
2-Methylpropanoic acetyl ester | 2.10 | 0.29 | 0.32 | ||||||||||||||||||||||||
2,3-Dimethylcyclohexanol | 0.39 | ||||||||||||||||||||||||||
Decanal | 0.25 | 0.13 | |||||||||||||||||||||||||
β-Pinone | 0.15 | ||||||||||||||||||||||||||
3-Methylpentane | 0.11 | 1.05 | |||||||||||||||||||||||||
β-Thujone | 2.58 | ||||||||||||||||||||||||||
Isohexane | 1.12 | ||||||||||||||||||||||||||
Neohexane | 0.82 | ||||||||||||||||||||||||||
p-Methylbenzaldehyde | 0.24 | 0.51 | |||||||||||||||||||||||||
Pentanol | 0.18 | ||||||||||||||||||||||||||
Citronellene | 2.71 | ||||||||||||||||||||||||||
Pentadecanol | 0.19 | ||||||||||||||||||||||||||
2-Ethyl-1-butanol | 0.19 | ||||||||||||||||||||||||||
Cedryl acetate | 0.21 | ||||||||||||||||||||||||||
Myristic acid | 0.10 | ||||||||||||||||||||||||||
Isoamyl butyrate | 0.13 | ||||||||||||||||||||||||||
Perillyl aldehyde | 0.12 | ||||||||||||||||||||||||||
sogeraniol | 0.10 | ||||||||||||||||||||||||||
Methyl anthranilate | 7.76 | ||||||||||||||||||||||||||
Piperitone | 3.01 | ||||||||||||||||||||||||||
3,5-Dimethyl-2-cyclohexen-1-one | 2.64 |
Code | Terpene | Alkane | Aromatic | Ester | Alcohol | Aldehyde | Ketone | Ether | Phenol | Acid | Total |
---|---|---|---|---|---|---|---|---|---|---|---|
1 | 10.71 (12) | 2.15 (7) | 39.29 (10) | 11.03 (13) | 0.67 (2) | 2.63 (3) | 27.31 (3) | 0.39 (2) | 94.18 (52) | ||
2 | 47 (19) | 0.47 (4) | 0.53 (1) | 33.4 (9) | 4.97 (8) | 5.99 (3) | 0.16 (1) | 92.51 (45) | |||
3 | 34.39 (14) | 0.49 (3) | 0.97 (2) | 4.58 (12) | 43.08 (17) | 1.88 (6) | 6.86 (3) | 92.24 (57) | |||
4 | 71.50 (22) | 2.23 (7) | 0.73 (3) | 0.46 (2) | 14.76 (12) | 0.67 (4) | 2.34 (1) | 0.70 (3) | 4.03 (2) | 97.42 (56) | |
5 | 90.16 (29) | 1.09 (3) | 0.77 (2) | 0.47 (2) | 2.49 (8) | 0.54 (3) | 0.22 (1) | 95.74 (48) | |||
6 | 14.38 (14) | 23.83 (6) | 0.26 (1) | 19.73 (8) | 19.61 (6) | 0.53 (1) | 16.04 (4) | 94.38 (40) | |||
7 | 3.85 (9) | 0.13 (1) | 0.29 (1) | 14.35 (14) | 73.11 (12) | 1.41 (5) | 1.06 (1) | 94.21 (43) | |||
8 | 35.83 (20) | 0.31 (1) | 1.68 (4) | 3.91 (5) | 51.11 (8) | 0.94 (4) | 0.26 (2) | 94.03 (44) | |||
9 | 21.14 (19) | 1.95 (6) | 23.52 (7) | 47.62 (9) | 0.65 (1) | 0.53 (1) | 95.42 (43) | ||||
10 | 31.58 (17) | 0.73 (3) | 0.54 (2) | 15.52 (6) | 26.19 (17) | 10.96 (3) | 0.46 (1) | 6.26 (1) | 0.12 (1) | 92.37 (51) | |
11 | 50.69 (17) | 4.03 (5) | 4.52 (2) | 10.62 (11) | 26.59 (10) | 0.49 (3) | 0.30 (2) | 97.25 (50) | |||
12 | 26.96 (8) | 0.75 (5) | 40.14 (6) | 5.10 (10) | 0.99 (2) | 0.54 (2) | 18.94 (2) | 93.41 (35) | |||
13 | 40.61 (14) | 0.70 (2) | 1.26 (4) | 13.16(10) | 32.20 (8) | 0.62 (2) | 0.36 (2) | 1.16 (1) | 90.08 (43) | ||
14 | 57.41 (19) | 11.52 (10) | 0.99 (1) | 21.03 (9) | 2.12 (7) | 1.90 (2) | 0.55 (1) | 95.53 (49) | |||
15 | 36.81 (17) | 0.90 (5) | 11.76 (5) | 38.87 (10) | 1.39 (2) | 1.70 (1) | 91.44 (40) | ||||
16 | 28.85 (18) | 14.03 (10) | 20.96 (19) | 26.14 (10) | 1.00 (2) | 2.47 (3) | 0.12 (1) | 0.58 (1) | 94.16 (64) | ||
17 | 30.90 (21) | 1.31 (5) | 1.11 (2) | 51.41 (12) | 7.05 (16) | 2.03 (2) | 0.20 (1) | 0.11 (1) | 94.13 (60) | ||
18 | 28.32 (16) | 2.15 (9) | 45.20 (15) | 6.06 (9) | 1.79 (4) | 0.67 (4) | 8.82 (1) | 93.02 (58) | |||
19 | 37.45 (25) | 9.52 (9) | 3.16 (4) | 14.81 (7) | 23.45 (11) | 0.24 (1) | 5.00 (4) | 93.63 (61) | |||
20 | 28.54 (14) | 12.36 (6) | 0.53 (2) | 17.13 (10) | 29.90 (10) | 0.10 (1) | 5.37 (3) | 0.14 (1) | 93.06 (47) | ||
21 | 36.84 (19) | 0.40 (2) | 30.41 (18) | 24.75 (12) | 0.15 (1) | 2.20 (1) | 0.40 (2) | 0.10 (1) | 95.25 (56) | ||
22 | 74.62 (26) | 0.22 (1) | 0.26 (1) | 17.69 (8) | 0.22 (2) | 93.02 (38) | |||||
23 | 14.00 (4) | 1.42 (3) | 30.68 (13) | 48.95 (11) | 0.62 (2) | 0.23 (1) | 0.67 (1) | 96.57 (35) | |||
24 | 18.22 (3) | 2.81 (8) | 29.43 (12) | 43.93 (9) | 1.44 (1) | 0.50 (1) | 96.33 (34) | ||||
25 | 24.22 (10) | 0.47 (1) | 5.76 (6) | 59.00 (12) | 3.68 (4) | 0.92 (1) | 0.37 (1) | 94.42 (35) | |||
26 | 89.03 (16) | 0.60 (3) | 0.14 (1) | 4.04 (12) | 1.09 (4) | 94.89 (36) | |||||
27 | 24.32 (15) | 10.87 (6) | 37.24 (14) | 5.34 (12) | 4.66 (3) | 14.02 (8) | 0.10 (1) | 96.54 (59) |
Code | Accession |
---|---|
1 | I. germanica wild species |
2 | I. germanica ‘Crown Princess’ |
3 | I. germanica ‘Swahili’ |
4 | I. germanica ‘Casual Elegance’ |
5 | I. germanica ‘Blessed Again’ |
6 | I. germanica ‘Hold and Behold’ |
7 | I. germanica ‘Forever Blue’ |
8 | I. germanica ‘Crinoline’ |
9 | I. germanica ‘Immortality’ |
10 | I. germanica ‘Indian chief’ |
11 | I. germanica ‘Summer Olympics’ |
12 | I. germanica ‘Spiced Custard’ |
13 | I. germanica ‘Lenora Pearls’ |
14 | I. germanica ‘Abridged Version’ |
15 | I. germanica ‘Lent a Williamson’ |
16 | I. germanica ‘Rare Edition’ |
17 | I. germanica ‘Rajah Brooke’ |
18 | I. germanica ‘Superstition’ |
19 | I. germanica ‘Splashacata’ |
20 | I. germanica ‘I’ ve Got Rhythm’ |
21 | I. germanica ‘Tulip Festival’ |
22 | I. germanica ‘Amsterdam’ |
23 | I. germanica ‘Wanda Rezac’ |
24 | I. pumila ‘Dash Away’ |
25 | I. pumila ‘Brassie’ |
26 | I. pallida ‘Dalmatica’ |
27 | I. pallida ‘Albo Variegata’ |
© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Yuan, Y.; Sun, Y.; Zhao, Y.; Liu, C.; Chen, X.; Li, F.; Bao, J. Identification of Floral Scent Profiles in Bearded Irises. Molecules 2019, 24, 1773. https://doi.org/10.3390/molecules24091773
Yuan Y, Sun Y, Zhao Y, Liu C, Chen X, Li F, Bao J. Identification of Floral Scent Profiles in Bearded Irises. Molecules. 2019; 24(9):1773. https://doi.org/10.3390/molecules24091773
Chicago/Turabian StyleYuan, Yuan, Ye Sun, Yanchun Zhao, Chungui Liu, Xiulan Chen, Fengtong Li, and Jianzhong Bao. 2019. "Identification of Floral Scent Profiles in Bearded Irises" Molecules 24, no. 9: 1773. https://doi.org/10.3390/molecules24091773
APA StyleYuan, Y., Sun, Y., Zhao, Y., Liu, C., Chen, X., Li, F., & Bao, J. (2019). Identification of Floral Scent Profiles in Bearded Irises. Molecules, 24(9), 1773. https://doi.org/10.3390/molecules24091773