Abstract
Chemical composition of the extract from the Pinus roxburghii Sarg. knotwood was studied for the first time. The extracts were obtained by ultrasound assisted sequential extraction of knotwood with hexane, acetone—water (95 : 5, v/v), and water. According to GC-MS analysis, hexane extract was dominated by monoterpenoids amounting to 53.57% and sesquiterpenoids (41.05%). Components of the acetone—water (95 : 5, v/v) extract were isolated, purified by HPLC, and identified by NMR spectroscopy and mass spectrometry as 2,3-bis(4-hydroxy-3-methoxybenzyl)butan-1,4-diol, 3-hydroxy-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one and 3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one. These compounds demonstrated notable antioxidant capacity determined using the amperometric method.
Similar content being viewed by others
References
A. Varun, D. P. Sharma, D. Rajeev. Bull. Env. Pharmacol. Life Sci., 2017, 6, 01–6.
A. Sharma, L. Sharma, R. Goyal, Pharmacogn. J., 2018, 10, 611–619; DOI: https://doi.org/10.5530/pj.2018.4.100.
D. N. Tewari, A Monograph on Chir Pine, International Book Distributors, India, 1994, 311 pp.
M. Bhagat, A. Bandrall, M. Bashir, K. Bindu, Indian J. Nat. Prod. Resour., 2018, 9, 34–38.
H. Pande, B. Kumar, V. K Varshney, Waste Biomass Valorization, 2016, DOI: https://doi.org/10.1007/s12649-016-9683-1.
D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, V. M. Menshov, D. V. Yashunsky, A. Ya. Yashin, Ya. I. Yashin, R. Kumar, V. K. Varshney, N. E. Nifantiev, J. Biol. Act. Prod. Nat., 2016, 6, 272–281; DOI: https://doi.org/10.1080/22311866.2016.1253502.
H. Pande, B. Kumar, VK. Varshney, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 2018, 57, 988–996.
A. Ya. Yashin, D. B. Yashunskii, A. N. Vedenin, N. E. Nifantiev, B. V Nemzer, Ya. I. Yashin, J. Anal. Chem., 2018, 73, 399–406; DOI: https://doi.org/10.1134/S106193481805012X].
D. E. Tsvetkov, R. Kumar, A. S. Dmitrenok, Yu. E. Tsvetkov, A. O. Chizhov, A. Ya. Yashin, Ya. I. Yashin, V. K. Varshney, N. E. Nifantiev, Russ. Chem. Bull., 68, 1756–1762.
P. Yang, F. Xu, H.-F. Li, Y. Wang, F.-C. Li, M.-Y Shang, G.-X Liu, X. Wang, S.-Q. Cai, Molecules, 2016, 21, 1209; DOI:10.3390/molecules21091209.
G. Loers, D. V Yashunsky, N. E. Nifantiev, M. Schachner, J. Nat. Prod., 2014, 77, 1554; DOI: https://doi.org/10.1021/np4009738.
M. Correia-da-Silva, E. Sousa, B. Duarte, F Marques, L. M. Cunha-Ribeiro, M. M. Pinto, Eur. J. Med. Chem., 2011, 46, 2347; DOI: https://doi.org/10.1016/j.ejmech.2011.03.016.
V B. Krylov, N. E. Ustyuzhanina, A. A. Grachev, N. E. Nifantiev, Tetrahedron left., 2008, 49. 5877; DOI: https://doi.org/10.1016/j.tetlet.2008.07.135.
C. P. Khare, Indian Medicinal Plants: an Illustrated Dictionary, Springer-Verlag, New York, 2007, 199–201.
S. Mohd, A. Mohd, A. Javed, J. N. Kamran, I. A. Mohd, J. Pharmacogn. Phytochem., 2013, 2, No. 1, 262–268.
H. Pereira, J. Graça, J. C. Rodrigues, in Wood Quality and its Biological Basis, Eds J. Barnett, G. Jeronimidis, Blackwell Publ., Oxford, 2003, pp. 53–86.
R. Allison, K. Graham, Appita J., 1988, 41, 197–202.
U. Sahlberg, TAPPIJ., 1995, 78, 162–168.
S. M. Willför, M. O. Ahotupa, J. E. Hemming, M. H. T. Reunanen, P. C. Eklund, Sjöholm, C. S. E. Eckerman, S. P. Pohjamo, B. R. Holmbom, J. Agric. Food Chem., 2003, 51, 7600–7606; DOI: https://doi.org/10.1021/jf030445h.
S. Willior, M. Reunanen, P. Eklund, R. Sjoholm, L. Kronberg, P. Fardim, S. Pietarinen, B. Holmbom, Holzforschung, 2004, 58, 345–354; DOI: https://doi.org/10.1515/HF.2004.053.
Z. Kebbi-Benkeder, F. Colin, S. Dumarcay, P. Gemtdin, Ann. For. Sci., 2015, 72, 277–284; DOI: https://doi.org/10.1007/sl3595-014-0428-7.
S. Johansson, K. Carlqvist, R. Kataria, T. Ulvcrona, U. Berg-sten, M. Arshadi, M. Galbe, G. Liden, Wood Sci. Technol., 2015, 49, 1037–1054; DOI: https://doi.org/10.1007/s00226-015-0739-3.
L. E. Lindberg, S. M. Willior, B. R. Holmbom, J. Ind. Microbiol. Biotechnol., 2004, 31, 137–147; DOI: https://doi.org/10.1007/s10295-004-0132-y.
NIST Standard Reference Database Number 69, Eds P. J. Linstrom, W G. Mallard}, National Institute of Standards and Technology, Gaithersburg (MD), 20899; DOI: https://doi.org/10.18434/T4D303, https://webbook.nist.gov.
R. P. Adams, Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, 4th ed, Allured Publishing Corp., Carol Stream, 2007, 804 pp.
L. Mondelo, Mass Spectra of Flavors and Fragrances of Natural and Synthetic Compounds, 3rd ed., Wiley Scientific, Technical and Medicinal Database, John Wiley & Sons, Hoboken, 2015.
P. Satyal, P. Paudel, J. Raut, A. Deo, N. S. Dosoky, W N. Setzer, Pharmacogn. Res., 2013, 5, 43–48.
R. M. Labib, F S. Youssef, M. L. Ashour, M. M. Abdel-Daim, S. A. Ross, Molecules, 2017, 22, 1384; DOI: https://doi.org/10.3390/molecules22091384.
O. Ekundayo, Flavour Fragrance J., 1988, 3, 1–11.
N. E. Nifantiev, D. V. Yashunsky, V. M. Men'shov, Yu. E. Tsvetkov, D. E. Tsvetkov, Pat. RF 2359666; Bull. Izobtret. [Invention Bull.], 2009, No. 19 (in Russian).
S. Willför, M. Ali, M. Karonen, M. Reunanen, M. Arfan, R. Harlamow, Holzforschung, 2009, 63, 551–558; DOI 10.1515/HF2009.095.
S. Tandon, R. P. Rasiiigi, Phytochem., 1976, 15, 1789–1791; DOI:10.1016/S0031-9422(00)97493-4.
R. Ekman, S. Willför, R. Sjöholm, M. Reunanen, J. Måki, R. Lehtilå, C. Eckerman, Holzforschung, 2002, 56, 253—256; DOI: https://doi.org/10.1515/HF2002.041.
E. Eich, H. Pertz, M. Kaloga, J. Schulz, M. R. Fesen, A. Mazumder, Y. Pommier, J. Med. Chem., 1996, 39, 86–95.
Y. I. Yashin, B. V. Nemzer, V. Yu. Ryzhnev, A. Ya. Yashin, N. I. Chernousova, P. A. Fedina, Molecules, 2010, 15, 7450–7466; DOI: https://doi.org/10.3390/moleculesl5107450.
A. Y. Yashin, D. V. Yashunsky, A. N. Vedenin, N. E. Nifantiev, Y. I. Yashin, B. V. Nemzer, Nutr. Food Sci., 2017, 47, 297–303; DOI: https://doi.org/10.1108/NFS-05-2016-0064.
D. V. Yashunsky, V. M. Men'shov, D. E. Tsvetkov, Yu. E. Tsvetkov, A. A. Belko, G. G. Vasiyarov, E. V. Titova, A. V. Pimenov, A. A. Onuchin, V. A. Dokichev, Yu. V. Tomilov, N. E. Nifantiev, Russ. Chem. Bull., 2014, 63, 2571–2576; DOI:10.1007/s11172-014-0780-7.
J. Gabaston, T. Richard, S. Cluzet, A. P. Pinto, M.-C. Dufour, M.-F Corio-Costet, J.-M. Merillon, J. Agric. Food Chem., 2017, 65, 8884–8891; DOI: https://doi.org/10.1021/acs.jafc.7b04129.
D.-E. Sok, H. S. Cui, M. R. Kim, Rec. Pat. Food, Nutr. Agric., 2009, 1, 87–95.
M.-X. Li, H.-Y Zhu, D.-H. Yang, X.-Q. Ma, C.-Z. Wang, S.-Q. Cai, G.-R. Liu, B.-S. Ku, S.-L. Liu, J. Appl. Microbiol., 2012, 113, 1352–1361; DOI: https://doi.org/10.1111/j.l365-2672.2012.05436.x.
O. S. Zhukova, L. V. Fetisova, A. V. Trishin, N. Yu. Anisi-mova, A. E. Shcherbakov, D. V. Yashunskii, D. E. Tsvetkov, V. M. Men'shov, M. V. Kiselevskii, N. E. Nifantiev, Bull. Exp. Biol. Med., 2010, 149, 511.
https://www.biocrick.com/Nortrachelogenin-BCN5280.html (checked on September 20, 2019).
J. S. Kebenei, P. K. Ndalut, A. O. Sabah, Int. J. Appl. Res. Nat. Prod., 2011, 4, 1–5.
M. Laavola, T. Leppanen, H. Erasalo, M. Hamalainen, R. Nieminen, E. Moilanen, Planta Med., 2017, 83, 519–526; DOI: https://doi.org/10.1055/S-0042-118188.
D. E. Tsvetkov, A. S. Dmitrenok, Yu. E. Tsvetkov, V. A. Dokichev, Yu. V. Tomilov, N. E. Nifantiev, Russ. Chem. Bull., 2015, 64, 1413–1418; DOI: https://doi.org/10.1007/s11172-015-1025-0.
S. P. Pietarinen, S. M. Willfor, M. O. Ahotupa, J. E. Hemming, B. R. Holmbom, J. Wood Sci., 2006, 52, 436–444; DOI 10.1007/sl0086-005-0780-1.
Author information
Authors and Affiliations
Corresponding authors
Additional information
The authors are grateful to A. Uniyal and A. K. Singh for their help in obtaining the knotwood extracts and the GC-MS analysis of the hexane extract.
This work was financially supported by the Russian Foundation for Basic Research (Project No. 17-53-45030) and the Department of Science&Technology, New Delhi, India (Project No. INT/RUS/RFBR/P-304).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2298–2306, December, 2019.
Rights and permissions
About this article
Cite this article
Tsvetkov, D.E., Kumar, R., Devrani, R. et al. Chemical constituents of the extracts of the knotwood of Pinus roxburghii Sarg. and their antioxidant activity. Russ Chem Bull 68, 2298–2306 (2019). https://doi.org/10.1007/s11172-019-2703-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-019-2703-0