Phytochemistry of Verbascum Species Growing in Iraqi Kurdistan and Bioactive Iridoids from the Flowers of Verbascum calvum
Abstract
:1. Introduction
2. Literature Data about the Verbascum Species Growing in Kurdistan
3. Phytochemical Studies on Vebascum Calvum
3.1. General Experimental Techniques and Procedures
3.2. Plant Material
3.3. Extraction of V. Calvum Flowers
3.4. Preliminary Phytochemical Analysis of Residues B and C
3.5. Preliminary Chromatographic Purification of Residues B and C
3.6. Folin–Ciocalteu Assay
3.7. Anti-radical Activity Test
3.8. Antibacterial Activity Test
3.9. Antifungal Activity Test
3.10. Tumor Cell Viability Test (MTS Assay)
3.11. Chromatographic Separation of Residue B’
3.12. Spectroscopic Data of Compounds 43 (Aucubin) and 42 (Ajugol)
3.13. Acidic Hydrolysis of Compounds 42 and 43
4. Results and Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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---|---|---|---|
Verbascum cheiranthifolium Boiss. | Rheumatism, eczema, earache, menstrual pains, haemorrhoids, oedema, earache and arthralgia [18] | Antioxidant [18], anti-inflammatory [19], anti-ulcerogenic [20], cytotoxic [21], insecticide [22,23], and antimicrobial effects [24]. | Aucubin (43), catalpol, 6-O-(E)-coumaroylaucubin, and 6-O-[(E)-p-methoxycinnamoyl]aucubin (1) [25] |
Verbascum songaricum Schrenk | Emmenagogue and to cure infertility [26] | antibacterial [27] and antifungal activities [28] | 3-O-{[α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranosyl}-olea-11,13-diene-3β,23,28-triol (songarosaponin A) (2), 3-O-{[α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→2)]-β-D-fuco-pyranosyl}-olea-11-ene-3β,13,23,28-tetrol (songarosaponin B), 3-O-{[β-D-glucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranosyl}-13β,28-epoxyolea-11-ene-3β,23-diol (songarosaponin C), 3-O-{[β-D-glucopyranosyl-(1→4)]-[β-D-glucopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranosyl}-13β,28-epoxyolea-11-ene-3β,16β,23-triol (songarosaponin D), 3-O-{[β-D-glucopyranosyl-(l→4)-β-D-glucopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranosyl}-olea-11,13-diene-3β,23,28-triol (songarosaponin E), 3-O-{[β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyranosyl}-olea-11,13-diene-3β,16β,23,28-tetrol (songarosaponin F), and 3-O-{[α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)]-[β-D-glucopyranosyl-(1→2)]-β-D-fucopyra- nosyl}-13β,28-epoxyolea-11-ene-3β,16β,23-triol (buddlejasaponin I) [29,30,31]. Poliumoside and verbascoside (3) inhibited mammalian DNA polymerases [32] |
Verbascum speciosum Schrad. | Skin diseases and wound bacterial infection [33] | insecticidal [33], antibacterial [34], antifungal [35] and wound healing potential [36] | Palmitic and oleic acids, (3β,5α)-stigmasta-7,25-dien-3-ol [37] |
Verbascum thapsus L. [38] | Although mullein has a long history as a favored herbal remedy for the treatment of many disorders [39,40,41,42], high-quality clinical researches have not been conducted so far, and there is no approved drug from this plant [43]. The traditional uses of V. thapsus have generally focused on effects aimed at wound healing [44,45,46], and treating Parkinson’s disease [47], diabetes [48,49,50], bronchitis [51], stomachache [52], snake bites [52], spasmodic cough [46], skin diseases [53], asthma [54], and joint pains [54]. The plant is also used as astringent [46] and sedative remedy [55]. | antioxidant [49,50,56], antibacterial [39,57,58,59], antiviral [60,61,62,63], anthelmintic [64,65], antihepatitis [66,67], anti-trichomonas [68,69], and anti-leishmanial effects [70]. | Luteolin (4) [71], apigetrin (apigenin 7-O-glucoside) (5) [71], 5-O-α-L-rhamnopyranoyl(1→3)-[β-D-glucuronopyranosyl-1→6)]-β-D-glucopyranosyl luteolin [72], and the dimer amentoflavone (6) [73]. verbathasin A (7) [71], ningpogenin (8) [71], 10-deoxyeucommiol (9) [71], jioglutolide (10) [71], 6β-hydroxy-2-oxabicyclo[4.3.0]Δ8-9-nonen-1-one (11) [71], (+)-genipin (12) [73], α-gardiol (13) and β-gardiol (14) [73]. Other characteristic terpenoids are buddlindeterpene A-C (15–17) [73], and 3α-hydroxy-drimmanyl-8-methanoate [74]. Iridoid glycosides include lateroside (18) [73,75,76], harpagoside (19) [71,73,75,76], compounds 20–41 [75], ajugol (42) [71,73,75,76], aucubin (43) [74,76], 6-O-β-xyloxyl aucubin [74], 8-cinnamoylmyoporoside (44) [71] and picroside IV (45) [73]. Lignan glycosides include compounds 46–50 [77], whereas phenylethanoid glycosides include compounds 51–56 [77], alyssonoside (57) [77,78], leucosceptoside B (58) [77,78], verbacoside (3) [73,78], leucosceptoside A (59) [78], martynoside (60) [78], samioside (61) [78], and isoverbascoside (62) [78]. Sterones and saponins include 24α-methyl-5α-cholestan-3-one, 24-ξ-ethyl-5α-cholestan-22-en-3-one, 24-ξ-ethyl-5β-cholestan-22-en-3-one, 24-ξ-ethyl-5α-cholestan-7-en-3-one, 24α-ethyl-5α-cholestan-Δ7,22-dien-3-one, 24-ξ-ethyl-5α-cholestan-3-one, 24-ξ-ethyl-5β-cholestan-3-one [74], and 3-O-fucopyranosylsaikogenin F (63) [71].Verbascoside (3) exhibited anti-inflammatory properties [79], whereas luteolin (4) and saponin 63 induced apoptosis of A549 lung cancer cells [71]. |
Sample. | Candida albicans | Aspergillus niger | Microsporum canis | Bipolaris oryzae |
---|---|---|---|---|
Extract B’ | >5 mg/mL | >5 mg/mL | 1 mg/mL | >1 mg/mL |
Extract C’ | >5 mg/mL | >5 mg/mL | - | >1 mg/mL |
Cell Line | 600 µg/mL | 60 µg/mL | 6 µg/mL | 0.6 µg/mL | 0.06 µg/mL |
---|---|---|---|---|---|
A549 | 48.43 | 44.95 | 14.69 | ̶ | ̶ |
MCF-7 | 19.62 | 18.35 | ̶ | ̶ | ̶ |
Proton/Carbon | Aucubin (43) | Ajugol (42) | ||
---|---|---|---|---|
1H a | 13C b | 1H a | 13C b | |
1 | 1H, 4.96 d (7.0) | 97.7 (CH) | 1H, 5.47 d (2.2) | 93.7 (CH) |
3 | 1H, 6.31 dd (6.0 and 1.8) | 141.6 (CH) | 1H, 6.16 dd (6.3 and 1.9) | 140.4 (CH) |
4 | 1H, 5.10 dd (6.0 and 4.0) | 105.7 (CH) | 1H, 4.78–4.82 (m) | 105.9 (CH) |
5 | 1H, 2.60–2.70 (m) | 46.3 (CH) | 1H, 2.69–2.74 (m) | 41.2 (CH) |
6 | 1H, 4.39–4.48 (m) | 82.8 (CH) | 1H, 3.90 ddd (5.6, 5.0, and 3.0) | 78.0 (CH) |
7 | 1H, 5.76 br s (t) | 130.3 (CH) | 1H, 1.79 dd (13.5, 5.0);1H, 2.05 dd (13.5 and 5.6) | 50.0 (CH2) |
8 | - | 148.0 (C) | - | 79.5 (C) |
9 | 1H, 2.89 br t (7.2) | 47.9 (CH) | 1H, 2.53 dd (9.5 and 2.2) | 51.8 (CH) |
10 | 2H, ABq centered at 4.25 (15.4) | 61.4 (CH2) | 3H, 1.30 s | 25.2 (CH3) |
1′ | 1H, 4.68 d (7.8) | 99.9 (CH) | 1H, 4.63 d (7.9) | 99.4 (CH) |
2′ | 1H, 3.21 dd (7.8 and 9.0) | 74.9 (CH) | 1H, 3.21 dd (8.0 and 9.0) | 74.8 (CH) |
3′ | 1H, 3.34 t (9.0) | 77.9 (CH) | 1H, 3.30–3.37 m | 77.8 (CH) |
4′ | 1H, 3.28 t (9.0) | 71.6 (CH) | 1H, 3.20–3.25 m | 71.7 (CH) |
5′ | 1H, 3.28–3.33 m | 78.3 (CH) | 1H, 3.28–3.33 m | 78.2 (CH) |
6′ | 1H, 3.65 dd (12.2 and 5.2);1H, 3.87 dd (12.2 and 1.5) | 62.7 (CH2) | 1H, 3.66 dd (12.0 and 5.2);1H, 3.91 dd (12.0 and 1.5) | 62.9 (CH2) |
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M. Amin, H.I.; Hussain, F.H.S.; Gilardoni, G.; Thu, Z.M.; Clericuzio, M.; Vidari, G. Phytochemistry of Verbascum Species Growing in Iraqi Kurdistan and Bioactive Iridoids from the Flowers of Verbascum calvum. Plants 2020, 9, 1066. https://doi.org/10.3390/plants9091066
M. Amin HI, Hussain FHS, Gilardoni G, Thu ZM, Clericuzio M, Vidari G. Phytochemistry of Verbascum Species Growing in Iraqi Kurdistan and Bioactive Iridoids from the Flowers of Verbascum calvum. Plants. 2020; 9(9):1066. https://doi.org/10.3390/plants9091066
Chicago/Turabian StyleM. Amin, Hawraz Ibrahim, Faiq H. S. Hussain, Gianluca Gilardoni, Zaw Min Thu, Marco Clericuzio, and Giovanni Vidari. 2020. "Phytochemistry of Verbascum Species Growing in Iraqi Kurdistan and Bioactive Iridoids from the Flowers of Verbascum calvum" Plants 9, no. 9: 1066. https://doi.org/10.3390/plants9091066