Recovery and Seasonal Variation of Cinnamtannin B-1 from Laurel (Laurus nobilis L.) Pruning Wood Wastes.
HPLC quantification
centrifugal partition chromatography (FCPC)
cinnamtannin B-1
laurel pruning wood wastes
semipreparative HPLC
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Feb 2022
Feb 2022
Historique:
received:
05
10
2021
accepted:
27
12
2021
pubmed:
20
1
2022
medline:
19
2
2022
entrez:
19
1
2022
Statut:
ppublish
Résumé
Cinnamtannin B-1 (C-B1) is a commercially-available trimeric A-type procyanidin with remarkable cellular actions mainly derived from its high radical scavenging activity. C-B1 is the main phenolic compound of laurel wood, which has previously been isolated by a combination of conventional chromatographic techniques. The first aim of this work was to find laurel trees containing as much C-B1 as possible, and learn about the influence of variables, such as gender and harvest time, on the production of C-B1 by the tree. It was found that all studied trees tend to give higher C-B1 percentages in the May-July period, from 6 % to 18 %, and lower ones around March (spring) and November (fall), from 1 % to 8 %. In a general way, it also seems that the female trees tend to produce a bit more C-B1 (from 2.8 % to 17.3 %) than male ones (from 1.7 % to 13.4 %). In addition, eight minor phenolic compounds [(-)-ent-catechin (1), (-)-ent-epicatechin-(4α→8)-ent-epicatechin (2), (epi)catechin-(4→8)-(epi)afzelechin-(4→8)-(epi)catechin (3), (+)-epiafzelechin-(4β→8)-epicatechin (4), (-)-epicatechin (5), (-)-afzelechin-(4α→8)-epicatechin (6), (epi)afzelechin-(4→8)-(epi)afzelechin-(4→8)-(epi)catechin (7) and (+)-epicatechin-(4β→8,2β→O-7)-epicatechin-(4β→8)-catechin (C-D1)] were found and quantified in the ethyl acetate extract of the wood samples. The second aim of this work was to improve the recovery of C-B1 from laurel wood. The use of the fast centrifugal partition chromatography (FCPC) technique has allowed for a recovery of 96 % of a technical-grade C-B1 (64 % in a previous protocol using conventional column chromatography on silica gel and size-exclusion chromatography).
Identifiants
pubmed: 35043548
doi: 10.1002/cbdv.202100807
doi:
Substances chimiques
Proanthocyanidins
0
cinnamtannin B-1
0
Catechin
8R1V1STN48
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202100807Subventions
Organisme : University of Jaén
ID : UJA081605
Organisme : Spanish Ministerio de Ciencia, Innovación y Universidades
ID : RTI2018-098560-B-C22
Organisme : Centro de Instrumentación Científico-Técnica (CICT)
Organisme : University of Jaén
Informations de copyright
© 2022 The Authors. Chemistry & Biodiversity published by Wiley-VHCA AG, Zurich, Switzerland.
Références
F. Chassagne, G. Cabanac, G. Hubert, B. David, G. Marti, ‘The landscape of natural product diversity and their pharmacological relevance from a focus on the Dictionary of Natural Products’, Phytochem. Rev. 2019, 18, 601-622.
M. C. S. Campelo, J. M. S. Medeiros, J. B. A. Silva, ‘Natural products in food preservation’, Int. Food Res. J. 2019, 26, 41-46.
M. Kanlayavattanakul, N. Lourith, ‘Plants and natural products for the treatment of skin hyperpigmentation - A review’, Planta Med. 2018, 84, 988-1006.
E. Araujo, G. Mota, M. S. Lorenço, U. L. Zidanes, L. Rodrigues da Silva, E. P. Silva, V. Ferreira, M. Cardoso, F. Mor, ‘Characterisation and valorisation of the bark of Myrcia eximia DC. trees from the Amazon rainforest as a source of phenolic compounds’, Holzforschung 2020, 74, 989-998.
V. G. Zuin, L. Z. Ramin, ‘Green and sustainable separation of natural products from agro-industrial waste: challenges, potentialities, and perspectives on emerging approaches’, Top. Curr. Chem. 2018, 376, 1-54.
K. B. Arun, A. Madhavan, R. Sindhu, P. Binod, A. Pandey, R. Reshmy, R. Sirohi, ‘Remodeling agro-industrial and food wastes into value-added bioactives and biopolymers’, Ind. Crops Prod. 2020, 154, 112621.
P. Rodríguez-Seoane, B. Díaz-Reinoso, A. Moure, H. Domínguez, ‘Potential of Paulownia sp. for biorefinery’, Ind. Crops Prod. 2020, 155, 112739.
A. Saha, B. B. Basak, ‘Scope of value addition and utilization of residual biomass from medicinal and aromatic plants’, Ind. Crops Prod. 2020, 145, 111979.
M. J. Rekha, B. K. Bettadaiah, T. C. Sindhu, K. A. Govindaraju, ‘Feasible method for isolation of pongamol from karanja (Pongamia pinnata) seed and its anti-inflammatory activity’, Ind. Crops Prod. 2020, 154, 112720-112731.
N. Chen, Z. Wu, W. Li, Y. Li, D. Luo, L. Chen, X. Zhang, Y. Zhang, G. Wang, Y. Li, ‘Acylphloroglucinols-based meroterpenoid enantiomers with antiviral activities from Dryopteris crassirhizoma’, Ind. Crops Prod. 2020, 150, 112415.
C.-L. Si, X. Z. Li, J. Lu, X. Tao, J. Zhang, W. Liu, Y. Bae, ‘Extractives of Cercidiphyllum japonicum twigs: isolation and structural elucidation of a new galloylflavonol glycoside, anomeric tannins and flavonoids’, Holzforschung 2018, 72, 719-725.
A. Alejo-Armijo, J. Altarejos, S. Salido, ‘Phytochemicals and biological activities of laurel tree (Laurus nobilis)’, Nat. Prod. Commun. 2017, 12, 743-757.
A. Alejo-Armijo, N. Glibota, M. P. Frías, J. Altarejos, A. Gálvez, E. Ortega-Morente, S. Salido, ‘Antimicrobial and antibiofilm activities of procyanidins extracted from laurel wood against a selection of foodborne microorganisms’, Int. J. Food Sci. Technol. 2017, 52, 679-686.
A. Alejo-Armijo, A. Tello-Abolafia, S. Salido, J. Altarejos, ‘Phenolic compounds in laurel wood: a new source of proanthocyanidins’, J. Wood Chem. Technol. 2019, 39, 436-453.
N. Ben Amor, A. Bouaziz, C. Romera-Castillo, S. Salido, P. J. Linares-Palomino, A. Bartegi, G. M. Salido, J. A. Rosado, ‘Characterization of the intracellular mechanisms involved in the antiaggregant properties of cinnamtannin B-1 from bay wood in human platelets’, J. Med. Chem. 2007, 50, 3937-3944.
A. Bouaziz, C. Romera-Castillo, S. Salido, P. J. Linares-Palomino, J. Altarejos, A. Bartegi, J. A. Rosado, G. M. Salido, ‘Cinnamtannin B-1 from bay wood exhibits antiapoptotic effects in human platelets’, Apoptosis 2007, 12, 489-498.
A. Bouaziz, S. Salido, P. J. Linares-Palomino, A. Sánchez, J. Altarejos, A. Bartegi, G. M. Salido, J. A. Rosado, ‘Cinnamtannin B-1 from bay wood reduces abnormal intracellular Ca2+ homeostasis and platelet hyperaggregability in type 2 diabetes mellitus patients’, Arch. Biochem. Biophys. 2007, 457, 235-242.
A. Tarasiuk, J. Fichna, ‘Effectiveness and therapeutic value of phytochemicals in acute pancreatitis: A review’, Pancreatology 2019, 19, 481-487.
C.-L. Yang, H.-C. Wu, T.-L. Hwang, C.-H. Lin, Y.-H. Cheng, C.-C. Wang, H.-L. Kan, Y.-H. Kuo, I.-S. Chen, H. Chang, ‘Anti-inflammatory and antibacterial activity constituents from the stem of Cinnamomum validinerve’, Molecules 2020, 25, 3382.
G. Nonaka, S. Morimoto, I. Nishioka, ‘Tannins and related compounds. Part 13. Isolation and structures of trimeric, tetrameric and pentameric proanthocyanidins from cinnamon’, J. Chem. Soc. Perkin Trans. 1 1983, 1983, 2139-2145.
K. B. Killday, M. H. Davey, J. A. Glinski, P. Duan, R. Veluri, G. Proni, F. J. Daugherty, M. S. Tempesta, ‘Bioactive A-type proanthocyanidins from Cinnamomum cassia’, J. Nat. Prod. 2011, 74, 1833-1841.
H. Lin, S. Lee, ‘Dibenzocycloheptanoids from the leaves of Cinnamomum subavenium’, J. Nat. Prod. 2012, 75, 1735-1743.
R. Buathong, F. Schindler, J. Schinnerl, K. Valant-Vetschera, M. Bacher, A. Potthast, T. Rosenau, S. Vajrodaya, ‘Uncommon fatty acids, iridoids and other secondary metabolites from the medicinal plant species Ixora cibdela Craib (Rubiaceae)’, Phytochem. Lett. 2019, 33, 77-80.
R. P. Medina, I. T. A. Schuquel, A. M. Pomini, C. C. Silva, C. M. A. Oliveira, L. Kato, C. V. Nakamura, S. M. O. Santin, ‘Ixorine, a new cyclopeptide alkaloid from the branches of Ixora brevifolia’, J. Braz. Chem. Soc. 2016, 27, 753-758.
Y. Lin, S. Tsai, S. Lee, ‘Oligoepicatechins from the leaves of Machilus konishii’, J. Chin. Chem. Soc. 2014, 61, 589-593.
H. Park, S. Kim, N. Song, J. Cho, J. Kang, T. Jeong, D. Lee, G. Kim, Y. Kim, H. Kang, N.-I. Baek, ‘Procyanidins from the stem wood of Machilus japonica and their inhibitory effect on LDL oxidation’, Arch. Pharm. Res. 2014, 37, 1403-1410.
G. Huh, J. Park, J. Kang, T. Jeong, H. Kang, N.-I. Baek, ‘Flavonoids from Lindera glauca Blume as low-density lipoprotein oxidation inhibitors’, Nat. Prod. Res. 2014, 28, 831-834.
S. N. Sulaiman, M. Hariono, H. M. Salleh, S.-L. Chong, L. S. Yee, A. Zahari, H. A. Wahab, S. Derbre, K. Awang, ‘Chemical constituents from Endiandra kingiana (Lauraceae) as potential inhibitors for dengue type 2 NS2B/NS3 serine protease and its molecular docking’, Nat. Prod. Commun. 2019, 14, 1-5.
J. J. López, I. Jardín, G. M. Salido, J. A. Rosado, ‘Cinnamtannin B-1 as an antioxidant and platelet aggregation inhibitor’, Life Sci. 2008, 82, 977-982.
D. González, H. Liu, C. Khoo, M. V. Moreno-Arribas, B. Bartolomé, ‘Some new findings regarding the antiadhesive activity of cranberry phenolic compounds and their microbial-derived metabolites against uropathogenic bacteria’, J. Agric. Food Chem. 2019, 67, 2166-2174.
Z. Chi, X. Ma, G. Cui, M. Li, F. Li, ‘Cinnamtannin B-1 regulates cell proliferation of spinal cord astrocytes and protects the cell from oxygen-glucose-serum deprivation/reoxygenation-induced apoptosis’, Int. J. Mol. Sci. 2013, 14, 15827-15837.
P. P. Carriere, N. Kapur, H. Mir, A. B. Ward, S. Singh, ‘Cinnamtannin B-1 inhibits cell survival molecules and induces apoptosis in colon cancer’, Int. J. Oncol. 2018, 53, 1442-1454.
Y. Li, Y. Yang, Q. Jia, H. Zhang, L. Chen, C. Shi, Y. Yang, ‘Pharmaceutical composition containing cinnamtannin B-1 and/or cinnamtannin D-1 for treating systemic lupus erythematosus and preparation method thereof’, 2017, patent application no. CN 106619608 A 20170510.
A. T. Romero, B. Qin, ‘Compositions comprising cinnamtannin D-1 and/or cinnamtannin B-1 for inhibiting expression of P-L1 (CD274) and enhancing expression of PD-1 for treating cardiac conditions’, 2019, patent application no. US 20190076397 A1, 20190314.
Enzo Life Sciences (ELS) AG. Cinnamtannin B-1, Available at: https://www.enzolifesciences.com/ALX-350-365/cinnamtannin-b-1 (Accessed September 26, 2021).
AdipoGen Life Sciences AG. Cinnamtannin B-1, Availabe at: https://adipogen.com/ag-cn2-0428-cinnamtannin-b-1.html (Accessed September 26, 2021).
A. Alejo-Armijo, S. Salido, J. Altarejos, ‘Synthesis of A-type proanthocyanidins and their analogs: A comprehensive review’, J. Agric. Food Chem. 2020, 68, 8104-8118.
Y. Ito, K. Ohmori, K. Suzuki, ‘Annulation approach to doubly linked (A-type) oligocatechins: syntheses of (+)-procyanidin A2 and (+)-cinnamtannin B1’, Angew. Chem. Int. Ed. 2014, 53, 10129-10133;
Angew. Chem. 2014, 126, 10293-10297.
J. B. Friesen, J. B. McAlpine, S.-N. Chen, G. F. Pauli, ‘Countercurrent separation of natural products: An update’, J. Nat. Prod. 2015, 78, 1765-1796.
G. López.’Guía de los árboles y arbustos de la península Ibérica y Baleares’, 3rd edn. Mundi-Prensa, 2002.
M. Pérez-Bonilla, S. Salido, A. Sánchez, T. van Beek, J. Altarejos, ‘Effect of extraction conditions on the antioxidant activity of olive wood extracts’, Int. J. Food Sci. 2013, 1, 1-13.
E. Tálos-Nebehaj, T. Hofmann, L. Albert, ‘Seasonal changes of natural antioxidant content in the leaves of Hungarian forest trees’, Ind. Crops Prod. 2017, 98, 53-59.
B. Sun, Y. Yang, X. Hu, X. Xie, J. Meucci, M. Fang, L. Zhao, ‘Purification of puerarin from Pueraria lobata by FCPC versus HSCCC using small-volume columns’, Chin. Herb. Med. 2014, 6, 140-144.
K. Skalicka-Woźniak, I. Garrard, ‘Counter-current chromatography for the separation of terpenoids: A comprehensive review with respect to the solvent systems employed’, Phytochem. Rev. 2014, 13, 547-572.
A. Berthod, ‘Countercurrent chromatography - The support-free liquid stationary phase’, In ‘Comprehensive Analytical Chemistry’, Ed. D. Barcelo, Elsevier Science Publishers, Amsterdam, 2002, p. 1-397.
M. Monagas, I. Garrido, R. Lebrón-Aguilar, B. Bartolomé, C. Gómez-Cordovés, ‘Almond (Prunus dulcis (Mill.) D. A. Webb) skins as a potential source of bioactive polyphenols’, J. Agric. Food Chem. 2007, 55, 8498-8507.