Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha
Abstract
From the green alga Avrainvillea amadelpha, two new naturally halo-benzaldehyde derivatives were isolated by various chromatographic methods along with 10 known metabolites of bromophenols, sulfonoglycolipid, and steroids. Based on the 1D and 2D NMR spectra as well as on MS data, the structures of the new compounds were identified as 5-bromo-2-(3-bromo-4-hydroxybenzyl)-3,4-dihydroxybenzaldehyde named avrainvilleal (1), and 3-iodo-4-hydroxy-benzaldehyde (2). Using SRB assay, both compounds showed mild and weak cytotoxic activity against HeLa and MCF-7 cancer cell lines, compared to the good activity of their extract (IC50 values 3.1 and 4.3 μg/mL, respectively). However, avrainvilleal (1) displayed an effective scavenged DPPH radical activity with IC50 value 3.5 μM, compared to the antioxidant quercetin with IC50 value 1.5 μM.
Funding source: King Abdulaziz University
Acknowledgments
This project was funded by the Deanship of Scientific Research (DSR) at King Abdulaziz University, Jeddah under grant No (G: 659-150-1439). The authors, therefore, acknowledge with thank DSR for technical and financial support.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: None declared.
Conflict of interest statement: The authors declare no conflict of interest relating to the article.
References
1. Jesus, A, Correia-da-Silva, M, Afonso, C, Pinto, M, Cidade, H. Isolation and potential biological applications of haloaryl secondary metabolites from macroalgae. Mar Drugs 2019;17:73. https://doi.org/10.3390/md17020073.Suche in Google Scholar
2. Stojkovich, JO. A systematic study of the genus Avrainvillea Decaisne (Chlorophyta, Udoteaceae). Nova Hedwigia 1985;41:1–68.Suche in Google Scholar
3. Öztaskın, N, Taslimi, P, Maras, A, Gülcin, I, Göksu, S. Novel antioxidant bromophenols with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions. Bioorg Chem 2017;74:104–14.10.1016/j.bioorg.2017.07.010Suche in Google Scholar PubMed
4. Colon, M, Guevara, P, Gerwick, WH, Ballantine, D. 5′-Hydroxyisoavrainvilleol, a new diphenylmethane derivative from the tropical green alga Avrainvillea nigricans. J Nat Prod 1987;50:368–74. https://doi.org/10.1021/np50051a005.Suche in Google Scholar
5. Andersen, RJ, Taglialatela-Scafat, O. Avrainvilloside, a 6-deoxy-6-aminoglucoglycerolipid from the green alga Avrainvillea nigricans. J Nat Prod 2005;68:1428–30. https://doi.org/10.1021/np050161m.Suche in Google Scholar
6. Williams, DE, Sturgeon, CM, Roberge, MA, Raymond, J. Nigricanosides A and B, antimitotic glycolipids isolated from the green alga Avrainvillea nigricans collected in Dominica. J Am Chem Soc 2007;129:5822–3. https://doi.org/10.1021/ja0715187.Suche in Google Scholar
7. Chen, JL, Gerwick, WH. Isorawsonol and related IMP dehydrogenase inhibitors from the tropical green algae Avrainvillea rawsonii. J Nat Prod 1994;57:947–52. https://doi.org/10.1021/np50109a011.Suche in Google Scholar
8. Hay, ME, Paul, VJ, Renaud, PE, Fenical, W. Specialist herbivores reduce their susceptibility to predation by feeding on the chemically defended seaweed Avrainvillea longicaulis. Limnol Oceanogr 1990;35:1734–43. https://doi.org/10.4319/lo.1990.35.8.1734.Suche in Google Scholar
9. Suzuki, M, Kowata, N, Kurosawa, E. Bromophenols from the red alga Rhodomela larix. Bull Chem Soc Jpn 1980;53:2099–100. https://doi.org/10.1246/bcsj.53.2099.Suche in Google Scholar
10. Xu, X, Fan, X, Song, F, Shi, J. Bromophenols from the brown alga Leathesia nana. J Asian Nat Prod Res 2005;6:217–21.10.1080/10286020310001653273Suche in Google Scholar PubMed
11. Reshef, V, Mizrachi, E, Maretzki, T, Silberstein, C, Loya, S, Hizi, A, et al.. New acylated sulfoglycolipids and digalactolipids and related known glycolipids from cyanobacteria with a potential to inhibit the reverse transcriptase of HIV-1. J Nat Prod 1997;60:1251–60. https://doi.org/10.1021/np970327m.Suche in Google Scholar
12. Khan, NM, Hossain, MS. Scopoletin and β-sitosterol glucoside from roots of Ipomoea digitata. J Pharmacogn Phytochem 2015;4:5–7.Suche in Google Scholar
13. Schmidt, B, Riemer, M, Karras, M. 2,2′-Biphenols via protecting group-free thermal or microwave-accelerated Suzuki-Miyaura coupling in water. J Org Chem 2013;78:8680–8. https://doi.org/10.1021/jo401398n.Suche in Google Scholar
14. El-Kassem, LT, Mohammed, RS, El Souda, SS, El-Anssary, AA, Hawas, UW, Mohmoud, K, et al.. Digalacturonide flavones from Egyptian Lantana camara flowers with in vitro antioxidant and in vivo hepatoprotective activities. Z Naturforsch C 2012;67:381–90. https://doi.org/10.5560/znc.2012.67c0381.Suche in Google Scholar
15. Skehan, P, Storeng, R, Scudiero, D, Monks, A, McMahon, J, Vistica, D, et al.. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990;82:1107–12. https://doi.org/10.1093/jnci/82.13.1107.Suche in Google Scholar
16. Sun, HH, Paul, VJ, Fenical, W. Avrainvilleol, a brominated diphenylmethane derivative with feeding deterrent properties from the tropical green alga Avrainvillea longicaulis. Phytochemistry 1983;22:743–5. https://doi.org/10.1016/s0031-9422(00)86974-5.Suche in Google Scholar
17. Whitfield, FB, Helidoniotis, F, Shaw, KJ, Svoronos, D. Distribution of bromophenols in species of marine algae from Eastern Australia. J Agric Food Chem 1999;47:2367–73. https://doi.org/10.1021/jf981080h.Suche in Google Scholar
18. Takamatsu, S, Hodges, TW, Rajbhandari, I, Gerwick, WH, Hamann, MT, Nagle, DG. Marine natural products as novel antioxidant prototypes. J Nat Prod 2003;66:605–8. https://doi.org/10.1021/np0204038.Suche in Google Scholar
19. Liu, M, Hansen, PE, Lin, X. Bromophenols in marine algae and their bioactivities. Mar Drugs 2011;9:1273–92. https://doi.org/10.3390/md9071273.Suche in Google Scholar
20. Salvador, JA, Carvalho, JF, Neves, MA, Silvestre, SM, Leitao, AJ, Silva, MM, et al.. Anticancer steroids: linking natural and semi-synthetic compounds. Nat Prod Rep 2013;30:324–74. https://doi.org/10.1039/c2np20082a.Suche in Google Scholar
Supplementary material
The online version of this article offers supplementary material (https://doi.org/10.1515/znc-2020-0221).
The 1D- and 2D-NMR and mass spectra of compound 1-3 are available as Supporting Information.
© 2021 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Research Articles
- Chemical composition, antioxidant and antimicrobial activity of essential oils from tangerine (Citrus reticulata L.), grapefruit (Citrus paradisi L.), lemon (Citrus lemon L.) and cinnamon (Cinnamomum zeylanicum Blume)
- Down-regulation of SORL1 is associated with Alzheimer’s disease through activating ABC transporter pathway
- Essential oil chemical composition, antimicrobial, anticancer, and antioxidant effects of Thymus convolutus Klokov in Turkey
- Analysis and chemotaxonomic significance of pyrrolizidine alkaloids from two Boraginaceae species growing in Algeria
- Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha
- PEPPSI complexes as potential prodrugs: enzyme inhibition, antioxidant activity, electrochemical characterization, molecular docking analysis
- Anti-Leishmania activity of extracts from Piper cabralanum C.DC. (Piperaceae)
- Anticancer Cardenolides from the aerial parts of Calortopis procera
- Cytotoxic withanolides from Datura innoxia
- Book Review
- A. Sigel, E. Freisinger & R. K. O. Sigel (Eds.), M. E. Sosa Torres & P. M. H. Kroneck (volume Eds.): Transition Metals and Sulfur – A Strong Relationship for Life
Artikel in diesem Heft
- Frontmatter
- Research Articles
- Chemical composition, antioxidant and antimicrobial activity of essential oils from tangerine (Citrus reticulata L.), grapefruit (Citrus paradisi L.), lemon (Citrus lemon L.) and cinnamon (Cinnamomum zeylanicum Blume)
- Down-regulation of SORL1 is associated with Alzheimer’s disease through activating ABC transporter pathway
- Essential oil chemical composition, antimicrobial, anticancer, and antioxidant effects of Thymus convolutus Klokov in Turkey
- Analysis and chemotaxonomic significance of pyrrolizidine alkaloids from two Boraginaceae species growing in Algeria
- Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha
- PEPPSI complexes as potential prodrugs: enzyme inhibition, antioxidant activity, electrochemical characterization, molecular docking analysis
- Anti-Leishmania activity of extracts from Piper cabralanum C.DC. (Piperaceae)
- Anticancer Cardenolides from the aerial parts of Calortopis procera
- Cytotoxic withanolides from Datura innoxia
- Book Review
- A. Sigel, E. Freisinger & R. K. O. Sigel (Eds.), M. E. Sosa Torres & P. M. H. Kroneck (volume Eds.): Transition Metals and Sulfur – A Strong Relationship for Life