journal article
Open Access
Jul 12, 2021
Dihydroisocoumarins, Naphthalenes, and Further Polyketides from Aloe vera and A. plicatilis: Isolation, Identification and Their 5-LOX/COX-1 Inhibiting Potency
Abstract
The present study aims at the isolation and identification of diverse phenolic polyketides from Aloe vera (L.) Burm.f. and Aloe plicatilis (L.) Miller and includes their 5-LOX/COX-1 inhibiting potency. After initial Sephadex-LH20 gel filtration and combined silica gel 60- and RP18-CC, three dihydroisocoumarins (nonaketides), four 5-methyl-8-C-glucosylchromones (heptaketides) from A. vera, and two hexaketide-naphthalenes from A. plicatilis have been isolated by means of HSCCC. The structures of all polyketides were elucidated by ESI-MS and 2D 1H/13C-NMR (HMQC, HMBC) techniques. The analytical/preparative separation of 3R-feralolide, 3′-O-β-d-glucopyranosyl- and the new 6-O-β-d-glucopyranosyl-3R-feralolide into their respective positional isomers are described here for the first time, including the assignment of the 3R-configuration in all feralolides by comparative CD spectroscopy. The chromones 7-O-methyl-aloesin and 7-O-methyl-aloeresin A were isolated for the first time from A. vera, together with the previously described aloesin (syn. aloeresin B) and aloeresin D. Furthermore, the new 5,6,7,8-tetrahydro-1-O-β-d-glucopyranosyl- 3,6R-dihydroxy-8R-methylnaphtalene was isolated from A. plicatilis, together with the known plicataloside. Subsequently, biological-pharmacological screening was performed to identify Aloe polyketides with anti-inflammatory potential in vitro. In addition to the above constituents, the anthranoids (octaketides) aloe emodin, aloin, 6′-(E)-p-coumaroyl-aloin A and B, and 6′-(E)-p-coumaroyl-7-hydroxy-8-O-methyl-aloin A and B were tested. In the COX-1 examination, only feralolide (10 µM) inhibited the formation of MDA by 24%, whereas the other polyketides did not display any inhibition at all. In the 5-LOX-test, all aloin-type anthranoids (10 µM) inhibited the formation of LTB4 by about 25–41%. Aloesin also displayed 10% inhibition at 10 µM in this in vitro setup, while the other chromones and naphthalenes did not display any activity. The present study, therefore, demonstrates the importance of low molecular phenolic polyketides for the known overall anti-inflammatory activity of Aloe vera preparations.
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References
48
[1]
Reynolds, T. (2004). Editor: The Genus Aloe, CRC Press.
[2]
Keller "Aloe" Hagers Handbuch der Pharmazeutischen Praxis (1992)
[3]
Rauwald "Three 8-C-glucosyl-5-methyl-chromones from Aloe barbadensis (Ph. Eur. 1997)" Pharmazie (1997)
[4]
Rauwald "Bestimmung der Konfiguration der beiden diastereomeren C-Glucosylanthrone Aloin A und B" Angew. Chem. (1989) 10.1002/ange.19891011114
[5]
Rauwald "Simultaneous determination of 18 polyketides typical of Aloe by high performance liquid chromatography and photodiode array detection" Phytochem. Anal. (1994) 10.1002/pca.2800050510
[6]
Sigler "Aloe Plants Accumulate Anthrone-Type Anthranoids in Inflorescence and Leaves, and Tetrahydroanthracenes in Roots" Zeitschrift für Naturforschung (1994) 10.1515/znc-1994-5-602
[7]
Rauwald "Naturally occurring quinones and their related reduction forms: Analysis and analytical methods" PZ Wissenschaft. (1990)
[8]
Dannhardt "In-vitro evaluation of 5-lipoxygenase and cyclo-oxygenase inhibitors using bovine neutrophils and platelets and HPLC" J. Pharm. Pharmacol. (1992) 10.1111/j.2042-7158.1992.tb03636.x
[9]
Dannhardt "Cyclooxygenase inhibitors--current status and future prospects" Eur. J. Med. Chem. (2001) 10.1016/s0223-5234(01)01197-7
[10]
Dannhardt "In-vitro test system for the evaluation of cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) inhibitors based on a single HPLC run with UV detection using bovine aortic coronary endothelial cells (BAECs)" Inflamm. Res. (2001) 10.1007/s000110050752
[11]
Dannhardt "Identification and 5-lipoxygenase inhibiting potency of medicarpin isolated from roots of Ononis spinosa L." Pharma. Pharmacol. Lett. (1992)
[12]
Speranza "Feralolide, a dihydroisocoumarin from cape aloe" Phytochemistry (1993) 10.1016/0031-9422(93)85417-p
[13]
Veitch "A dihydroisocoumarin glucoside from Aloe hildebrandtii" Phytochemistry (1994) 10.1016/s0031-9422(00)94814-3
[14]
Maucher, R., Rauwald, H.W., and Niyonzima, D.D. (1997, January 7–12). Three 8-C-glucosylchromones and two dihydroisocoumarins from Aloe barbadensis (DAB 1996). Proceedings of the 45th Annual Congress of the Society of Medicinal Plant Research, Regensburg, Germany. Conference booklet: C25.
[15]
Maucher, R., and Rauwald, H.W. (1999, January 26–30). Stereoselective resolution and characterisation of dihydroisocoumarin glycosides from Aloe vera. Proceedings of the 5th Joint Meeting of ASP, AFERP, GA, PSE: 2000 Years of Natural Products Research, Past, Present and Future, Amsterdam, The Netherlands. Conference booklet.
[16]
Kurizaki, A., Watanabe, T., and Devkota, H.P. (2019). Chemical Constituents from the Flowers of Aloe arborescens. Nat. Prod. Commun., 14.
10.1177/1934578x19844135
[17]
Choi "Phytochemical Study of Aloe vera" Arch. Pharm. Res. (1996) 10.1007/bf02976854
[18]
Shaaban "New bioactive compounds from Aloe hijazensis" Nat. Prod. Res. (2009) 10.1080/14786410802242851
[19]
Hutter "Antiinflammatory C-glucosyl chromones from Aloe barbadensis" J. Nat. Prod. (1996) 10.1021/np9601519
[20]
Lee "Isolation and identification of a phenolic antioxidant from Aloe barbadensis" Free Radic. Biol. Med. (2000) 10.1016/s0891-5849(99)00235-x
[21]
Speranza "Aloeresin I, an anti-inflammatory 5-methylchromone from cape aloe" Planta Med. (2005) 10.1055/s-2005-837756
[22]
Yagi "Antioxidant, free radical scavenging and anti-inflammatory effects of aloesin derivatives in Aloe vera" Planta Med. (2002) 10.1055/s-2002-35666
[23]
Bisrat "Chromones and anthrones from Aloe marlothii and Aloe rupestris" Phytochemistry (2000) 10.1016/s0031-9422(00)00328-9
[24]
Rauwald "High-performance liquid chromatographic separation and determination of diastereomeric anthrone-C-glucosyls in Cape aloes" J. Chromatogr. A (1993) 10.1016/0021-9673(93)80276-e
[25]
Aldayel "LC-MS characterization of bioactive metabolites from two Yemeni Aloe spp. with antioxidant and antidiabetic properties" Arab. J. Chem. (2020) 10.1016/j.arabjc.2020.02.003
[26]
Mikayoulou "Anti-tyrosinase activity of South African Aloe species and isolated compounds plicataloside and aloesin" Fitoterapia (2021) 10.1016/j.fitote.2021.104828
[27]
Speranza "Feroxidin, a novel 1-methyltetralin derivative isolated from cape aloe" Tetrahedron Lett. (1990) 10.1016/s0040-4039(00)89030-9
[28]
Speranza "Absolute configuration of feroxidin: An experimental support to Snatzke’s helicity rules for tetralins" Chirality (1991) 10.1002/chir.530030409
[29]
Speranza "Studies on Aloe, Part 10. Feroxins A and B, two O glucosylated 1-methyltetralins from Cape aloe" J. Nat. Prod. (1992) 10.1021/np50084a003
[30]
Hanske "The bioavailability of apigenin-7-glucoside is influenced by human intestinal microbiota in rats" J. Nutr. (2009) 10.3945/jn.108.102814
[31]
Malterud "Antioxidant and radical scavenging effects of anthraquinones and anthrones" Pharmacology (1993) 10.1159/000139846
[32]
Silva "Chromones: A Promising Ring System for New Anti-inflammatory Drugs" ChemMedChem (2016) 10.1002/cmdc.201600359
[33]
Yoshikawa "Dihydroisocoumarin constituents from the leaves of Hydrangea macrophylla var. thunbergii (2). Absolute stereostructures of hydrangenol, thunberginol I, and phyllodulcin glycosides and isomerization reaction at the 3-positions of phyllodulcin and its glycosides" Chem. Pharm. Bull. (1999) 10.1248/cpb.47.383
[34]
Liu "Medicinal flowers 40: Structures of dihydroisocoumarin glycosides and inhibitory effects on aldose reducatase from the flowers of Hydrangea macrophylla var.thunbergii" Chem. Pharm. Bull. (2013) 10.1248/cpb.c13-00160
[35]
Tomasik, P. (2003). Chemical and Functional Properties of Food Saccharides (Chemical & Functional Properties of Food Components, CRC Press.
10.1201/9780203495728
[36]
Matsuda "Effects of phyllodulcin, hydrangenol, and their 8-O-glucosides, and thunberginols A and F from Hydrangea macrophylla SERINGE var. thunbergii MAKINO on passive cutaneous anaphylaxis reaction in rats" Biol. Pharm. Bull. (1999) 10.1248/bpb.22.870
[37]
Yoshikawa "Development of bioactive functions in Hydrangeae dulcis folium. V. On the antiallergic and antimicrobial principles of Hydrangeae dulcis folium. (2). Thunberginols C, D, and E, thunberginol G 3′-O-glucoside, (-)-hydrangenol 4′-o-glucoside, and (+)-hydrangenol 4′-O-glucoside" Chem. Pharm. Bull. (1996) 10.1248/cpb.44.1440
[38]
Umehara "Differentiation inducing activities of isocoumarins from Hydrangea Dulcis Folium" Chem. Pharm. Bull. (2000) 10.1248/cpb.48.566
[39]
Endringer "Selective inhibition of aromatase by a dihydroisocoumarin from Xyris pterygoblephara" J. Nat. Prod. (2008) 10.1021/np800098f
[40]
Braga "Dihydroisocoumarin from Xyris pterygoblephara active against dermatophyte fungi" Phytochemistry (2008) 10.1016/j.phytochem.2007.08.002
[41]
Li "HPLC-based activity profiling for GABA(A) receptor modulators: A new dihydroisocoumarin from Haloxylon scoparium" J. Nat. Prod. (2010) 10.1021/np900803w
[42]
Syed "Management of psoriasis with Aloe vera extract in a hydrophilic cream: A placebo-controlled, double-blind study" Trop. Med. Int. Health (1996) 10.1046/j.1365-3156.1996.d01-91.x
[43]
Langmead "Randomized, double-blind, placebo-controlled trial of oral Aloe vera gel for active ulcerative colitis" Aliment Pharm. Ther. (2004) 10.1111/j.1365-2036.2004.01902.x
[44]
Krishnan "The scientific study of herbal wound healing therapies: Current state of play" Curr. Anaesth. Crit. Care (2006) 10.1016/j.cacc.2006.02.009
[45]
Moghbel "Wound Healing and Toxicity Evaluation of Aloe vera Cream on Outpatients with Second Degree Burns" Iran. J. Pharm. Sci. (2007)
[46]
Maenthaisong "The efficacy of Aloe vera used for burn wound healing: A systematic review" Burns (2007) 10.1016/j.burns.2006.10.384
[47]
Zago, R. (2000). Cancer Can Be Cured!, Waid Group Inc.
[48]
Ledergerber "Development of a screening assay for the in vitro evaluation of thromboxane A2 synthase inhibitors" J. Enzym. Inhib. (1995) 10.3109/14756369509036554
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14
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48
References
Details
- Published
- Jul 12, 2021
- Vol/Issue
- 26(14)
- Pages
- 4223
- License
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Authors
Cite This Article
Hans Wilhelm Rauwald, Ralf Maucher, Gerd Dannhardt, et al. (2021). Dihydroisocoumarins, Naphthalenes, and Further Polyketides from Aloe vera and A. plicatilis: Isolation, Identification and Their 5-LOX/COX-1 Inhibiting Potency. Molecules, 26(14), 4223. https://doi.org/10.3390/molecules26144223
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