Chemical constituents from the calli of Maytenus hookeri

doi:10.5246/jcps.2023.04.025

Abstract

Abstract:

In order to study the chemical compounds of the calli induced from Maytenus hookeri, the dried and fresh cells of the calli were extracted by heat refluxing and cold soaking method, respectively. The chemical constituents were purified through various column chromatography including silica gel, RP-18 and Sephadex LH-20 from the ethyl acetate extract. According to the NMR and MS analysis, sixteen compounds were identified as wilforlide A (1), wilforlide B (2), 3β,22α-dihydroxyolean-12-en-29-oic acid (3), 22α-hydroxy-3-oxoolean-12-en-29-oic acid (4), 3-epikatonic acid (5), oleana-9(11),12-dien-3-β-ol (6), 22α-hydroxy-3-oxo-12-ursen-30-oic acid (7), triptotriterpenic acid C (8), 2α,3β-dihydroxy-29-friedelanoic acid (9), maytenonic acid (10), 3β-hydroxystigmast-5-en-7-one (11), 7β-hydroxysitosterol (12), stigmast-4-ene-3-one (13), β-sitosterol (14), 1-β-D-glucpotyransyl-2,6-dimetoxi-4-propenyl-benzene (15) and adenosine (16). All compounds were reported in the calli of M. hookeri and the plant for the first time except 10 and 14.

Key words: Maytenus hookeri, Calli, Chemical constituents, Column chromatography

Supporting:

Lei Jiang, Yujiao Tu, Weihua Dai, Lin Yuan. Chemical constituents from the calli of Maytenus hookeri[J]. Journal of Chinese Pharmaceutical Sciences, 2023, 32(4): 283-290.

Figures/Tables 1

References 21

[1]	He, J.P.; Gu, J.; Huang, H.K.; Cao, Y.H.; Tan, R. Research progress of Maytenus Hookeri Loes. Chin. Arch. Tradit. Chin. Med. 2013, 31, 721–724.
[2]	Wang, J.; Li, J.X.; Li, J.L.; Gao, W.Y. Application of plant tissue culture in field of Chinese medicine resources. Chin. J. Chin. Mater. Med. 2017, 42, 2236–2246.
[3]	Lu, C.H.; Zhao, P.J.; Shen, Y.M. The callus tissue culture of maytenus hookeri and its chemical constituents. Nat. Prod. Res. Dev. 2002, 14, 11–13.
[4]	Lu, C.H.; Zhang, J.X.; Gan, F.Y.; Shen, Y.M. Chemical constituents of the suspension cell cultures of Maytenus hookeri. Acta Bot. Sin. 2002, 44, 603–610.
[5]	Wang, F.; Zhang, Y.; Zhao, Y.Q. Chemical constituents of tripterygium hypoglaucum. Chin. Tradit. Herb. Drugs. 2011, 42, 46–49.
[6]	Wang, K.W.; Yan, S.N. Chemical constituents of Symplocos setchuensis. Chem. Nat. Compd. 2018, 54, 1012–1014.
[7]	Jeong, E.J.; Bae, J.Y.; Rho, J.R.; Kim, Y.C.; Ahn, M.J.; Sung, S.H. Anti-inflammatory triterpenes from euonymus alatus leaves and twigs on lipopolysaccharide-activated RAW_264.7 macrophage cells. Bull. Korean Chem. Soc. 2014, 35, 2945–2949.
[8]	Yang, B.Y.; Meng, Y.; Liu, Z.X.; Jiang, Y.Q.; Zhou, Y.Y. Triterpenes from pericarps of juglans regia. Chin. J. Exp. Tradit. Med. Form. 2015, 21, 49–52.
[9]	Hamid, A.A.; Aiyelaagbe, O.O.; Negi, A.S.; Luqman, S.; Kaneez, F.; Bhukya, B.; Kumar, B.S.. Triterpenoids from the aerial parts of smilax kraussiana as antitumor agents. Chem. Nat. Compd. 2017, 53, 1192–1195.
[10]	Guo, J.L.; Liu, L.M.; Jiang, Z.Z.; Bi, Z.M.; Wang, H.; Ye, W.C. Studies on the chemical constituents of tripterygium wilfordill extract. Res. Pract. Chin. Med. 2011, 25, 41–44.
[11]	Yu, L.; Zuo, W.J.; Mei, W.L.; Guo, Z.K.; Li, X.N.; Dai, H.F. Three new terpenoids from trigonostemon xyphophylloides (croiz.) L.K. Dai and T.L. wu. Phytochem. Lett. 2013, 6, 472–475.
[12]	Hu, Z.Y.; Fan, Q.F.; Zhang, Y.M.; Feng, F.; Yang, J.L.; Song, Q.S. Chemical constituents from twigs of nothapodytesnimmoniana. Nat. Prod. Res. Dev. 2014, 26, 1605–1609, 1627.
[13]	Mi, C.N.; Mei, W.L.; Yuan, J.Z.; Long, W.X.; Dai, H.F. Chemical constituents from agarwood of aquilaria filaria. J. Chin. Pharm. Sci. 2021, 30, 505–517.
[14]	Liu, Y.; Wang, Z.Y.; He, W.J.; Tan, N.H.; Yin, Z.Q. Chemical constituents from stems and leaves of Micromelum integerrimum. Acta Pharm. Sin. 2015, 50, 475–479.
[15]	Xi, C.C.; Xu, Y.L.; Feng, K.; Wu, R.Z.; Luo, S.H. Chemical constituents from the seeds of Capparis masaikai. J. Chin. Pharm. Sci. 2021, 30, 924–931.
[16]	Zhang, X.Y.; Feng, J.T.; Zhang, X. Advances in studies on triterpenes constituents and their biological activities in species of maytenus. Acta Bot. Boreal. Occident. Sin. 2007, 27, 1484–1490.
[17]	Nozaki, H.; Matsuura, Y.; Hirono, S.; Kasai, R.; Chang, J.J.; Lee, K.H. Antitumor agents, 116. cytotoxic triterpenes from maytenus diversifolia. J. Nat. Prod. 1990, 53, 1039–1041.
[18]	Itokawa, H.; Shirota, O.; Ikuta, H.; Morita, H.; Takeya, K.; Iitaka, Y. Triterpenes from Maytenus ilicifolia. Phytochemistry. 1991, 30, 3713–3716.
[19]	Henneh, I.T.; Huang, B.S.; Musayev, F.N.; Hashimi, R.A.; Safo, M.K.; Armah, F.A.; Ameyaw, E.O.; Adokoh, C.K.; Ekor, M.; Zhang, Y. Structural elucidation and in vivo anti-arthritic activity of β-amyrin and polpunonic acid isolated from the root bark of Ziziphus abyssinica HochstEx. A Rich (Rhamnaceae). Bioorg. Chem. 2020, 98, 103744.
[20]	Lindsey, K.L.; Budesinsky, M.; Kohout, L.; van Staden, J. Antibacterial activity of maytenonic acid isolated from the root-bark of Maytenus senegalensis. S Afr N J. Bot. 2006, 72, 473–477.
[21]	Tan, W.Z.; Pu, D.B.; Feng, Y.; Li, H.Z. A new triterpenoid from maytenus austroyunnanensis. Nat. Prod. Res. Dev. 2016, 28, 173–178.