FAMILY TAXACEAE S.F.GRAY.: COMPOSITION OF METABOLITES, PHARMACOLOGICAL PROPERTIES, DRUGS
UDC 582.471: 581.192
Abstract
The review provides information on the systematics, distribution, composition of metabolites, biological activity of plants of the Taxaceae S.F.Gray. family, including 8 genus. According to taxonomists, the family has 30–35 species, most of which are endemic to Asia.
Across the globe medicine, since the 90s of the last century, the Taxaceae family has been known for the preparations «Paclitaxel®», «Docetaxel®», «Synribo®» with antitumor effect produced from some species.
In traditional Indian (Ayurveda), Tibetan, Chinese medicine, various parts of Taxus baccata, Taxus wallichiana, Cephalotaxushainanensis, Cephalotaxusmannii, Torreyagrandis are used.
The most studied are the antitumor properties and composition of some metabolites of 17 species of the family – Taxus brevifolia, Taxus baccata, Taxus cuspidata, Taxus wallichiana, Taxus yunnanensis, Torreya nucifera, Torreya grandis, Cephalotaxus wilsoniana, Cephalotaxus sinensis, Cephalotaxus oliveri, Cephalotaxus lanceolata, Cephalotaxus koreana, Cephalotaxus harringtonia, Cephalotaxus hainanensis, Cephalotaxus griffithii, Cephalotaxus fortunei, Amentotaxus formosana. More than 900 substances have been identified in the studied species - alkaloids, terpenoids, fatty acids, phenolic carboxylic acids, tannins, vitamins, lignans, sterols, amino acids, flavonoids, simple phenols, etc. An important marker of the family is probably the diterpene taxanes, which found in 17 species. This group of substances, as well as alkaloids, according to the literature, are decisive in the antitumor effect of species of the family.
Extracts and individual substances in the experiment in vivo, in vitro, in silico have a wide range of pharmacological activity: antitumor, antiproliferative, cytotoxic, antioxidant, anxiolytic, antinociceptive, anti-osteoporotic, anti-inflammatory, antibacterial, antiviral, neuroprotective, hypoglycemic, etc.
The information given in the review shows that plants of the Taxaceae family and their individual metabolites are promising for further study.
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Atanasov A.G., Zotchev S.B., Dirschandal V.M. Nat. Rev. Drug Discov., 2012, vol. 20, pр. 200–216. DOI: 10.1038/s41573-020-00114-z.
Schwikkard S.L., Mulholland D.A. Planta Medica, 2014, vol. 80, no. 14. DOI: 10.1055/s-0034-1368549.
Zmeyeva O.N., Kolomiyets N.Ye., Abramets N.Yu., Bondarchuk R.A. Khimiya rastitel'nogo syr'ya, 2017, no. 4, pp. 5–14. DOI: 10.14258/jcprm.2017041779. (in Russ.).
Mar'in A.A., Kolomiyets N.E. Fundamental'naya i klinicheskaya meditsina, 2017, vol. 2, no. 4, pp. 45–55. DOI: 10.23946/2500-0764-2017-2-4-45-55. (in Russ.).
Mar'in A.A., Tantsereva I.G., Bol'shakov V.V., Kolomiyets N.E. Fundamental'naya i klinicheskaya meditsina, 2019, vol. 4, no. 1, pp. 80–90. DOI: 10.23946/2500-0764-2019-4-1-80-90. (in Russ.).
Kolomiyets N.E., Shplis O.N. Khimiya rastitel'nogo syr'ya, 2022, no. 4, pp. 5–27. DOI: 10.14258/jcprm.20220411043. (in Russ.).
Simpson M. Plant systematics. Elsevier, 2010, 741 p. DOI: 10.1016/C2009-0-02260-0.
Takhtadzhyan A.L. Zhizn' rasteniy v shesti tomakh. T. 4. Mkhi. Plauny. Khvoshchi. Paporotniki. Golosemyannyye ras-teniya. [Life of Plants in Six Volumes. Vol. 4. Mosses. Club Mosses. Horsetails. Ferns. Gymnosperms]. Moscow, 1978, 513 p. (in Russ.).
Online Etymology Dictionary. URL: www.etymonline.com/word/taxine#etymonline_v_49449.
Chase M.W., Soltis D.E. et al. Annals of the Missouri Botanical Garden. JSTOR, 1993, vol. 80, no. 3, p. 528. DOI: 10.2307/2399846.
Anderson E., Owens J.N. Acta Horticulturae. International Society for Horticultural Science (ISHS), 2003, vol. 615, pp. 233–234. DOI: 10.17660/actahortic.2003.615.22.
Elpe C., Knopf P., Stützel T. et al. J. Plant Res., 2018, vol. 131, no. 1, pp. 125–141. DOI: 10.1007/s10265-017-0973-x.
Cheng W.-C., Fu Li-K., Chu C.-De. Fl. Reipubl. Popularis Sin., 1978, vol. 7, pp. 437–467.
Shirey P.D., Kunycky B.N. et al. Conservation Letters, 2013, vol. 6, no. 5, pp. 300–316. DOI: 10.1111/conl.12031.
Lee M.R. Journal of the Royal College of Physicians of Edinburgh, 1998, vol. 28, pp. 569–575.
Rastitel'nyye resursy Rossii: Komponentnyy sostav i biologicheskaya aktivnost' rasteniy. T. 7. Otdely Lycopodiophyta-Gnetophyta. [Plant resources of Russia: Component composition and biological activity of plants. Vol. 7. Departments Lycopodiophyta-Gnetophyta]. St. Petersburg, Moscow, 2016, 333 p. (in Russ.).
Hostettmann K., Marston A. Chimia, 2007, vol. 61, no. 6, pp. 322–326. DOI: 10.2533/chimia.2007.322.
Bharali P., Das S., Bhandari N. et al. IET Nanobiotechnol., 2019, vol. 13, no. 1, pp. 18–22. DOI: 10.1049/iet-nbt.2018.5036.
Wang L.W., Su H.J., Day S.H. et al. Planta Med., 2005, vol. 71, no. 4, pp. 344–348. DOI: 10.1055/s-2005-864101.
Lin C.N., Huang A.M., Lin K.W. et al. Phytochemistry, 2010, vol. 71, no. 17-18, pp. 2140–2146. DOI: 10.1016/j.phytochem.2010.08.012.
Chen H.L., Lin K.W., Gan K.H. et al. Fitoterapia, 2011, vol. 82, no. 2, pp. 219–224. DOI: 10.1016/j.fitote.2010.10.002.
Thanh N.T., Thuy L.T., Xuyen D.T. Chemistry & Biodiversity, 2023, vol. 20, no. 6, e202300604. DOI: 10.1002/cbdv.202300604.
Zhao C.X., Liu H., Zhang X. et al. Org. Biomol. Chem., 2022, vol. 14, no. 20(35), pp. 7076–7084. DOI: 10.1039/d2ob01242a.
Zhao J.X., Fan Y.Y., Xu J.B. et al. J. Nat. Prod., 2017, vol. 24, no. 80(2), pp. 356–362. DOI: 10.1021/acs.jnatprod.6b00802.
Ni L., Zhong X.H., Chen X.J. et al. Phytochemistry, 2018, vol. 151, pp. 50–60. DOI: 10.1016/j.phytochem.2018.04.007.
Bocar M., Jossang A., Bodo B. J. Nat. Prod., 2003, vol. 66, no. 1, pp. 152–154. DOI: 10.1021/np0203178.
Li Y.Z., Wang Y.T., Zhao C.X. et al. Fitoterapia, 2021, vol. 155, 105037. DOI: 10.1016/j.fitote.2021.105037.
Gong L., Chen C., Liu X. et al. Toxicol. Appl. Pharmacol., 2022, vol. 1, no. 454, 116249. DOI: 10.1016/j.taap.2022.116249.
Zhu L., Zhu D.R., Zhou W.X. et al. Org. Lett., 2021, vol. 2, no. 23(7), pp. 2807–2810. DOI: 10.1021/acs.orglett.1c00738.
Feng Q., Li B., Feng Y., Li X. et al. J. Nat. Med., 2019, vol. 73, no. 3, pp. 653–660. DOI: 10.1007/s11418-019-01308-5.
Ni L., Zhong X.H., Cai J. et al. Nat. Prod. Bioprospect., 2016, vol. 6, no. 3, pp. 149–154. DOI: 10.1007/s13659-016-0093-7.
Huang Q.P., Guo K., Liu Y. et al. Chem. Biodivers., 2020, vol. 17, no. 6, e2000210. DOI: 10.1002/cbdv.202000210.
Moirangthem D.S., Laishram S., Rana V.S. et al. Nat. Prod. Res., 2015, vol. 29, no. 12, pp. 1161–1165. DOI: 10.1080/14786419.2014.981540.
Moirangthem D.S., Borah J.C., Laishram S. et al. Nat. Prod. Res., 2014, vol. 28, no. 18, pp. 1503–1506. DOI: 10.1080/14786419.2014.913241.
Moirangthem D.S., Talukdar N.C., Kasoju N. et al. Altern. Med., 2012, vol. 3, 12:30. DOI: 10.1186/1472-6882-12-30.
Zhonghua Zhong Liu Za Zhi, 1979, vol. 1, no. 3, pp. 176–182.
Shi B., Han R. Yao Xue Xue Bao, 1998, vol. 33, no. 6, pp. 407–412.
Takeda S., Yajima N., Kitazato K. et al. J. Pharmacobiodyn., 1982, vol. 5, no. 10, pp. 841–847. DOI: 10.1248/bpb1978.5.841.
Kang S.Q., Cai S.Y., Teng L. Yao Xue Xue Bao, 1981, vol. 6, no. 11, pp. 867–868.
Takano I., Yasuda I., Nishijima M. et al. Phytochemistry, 1997, vol. 44, no. 4, pp. 735–738. DOI: 10.1016/s0031-9422(96)00574-2.
Komoto N., Nakane T., Matsumoto S. et al. J. Nat. Med., 2015, vol. 69, no. 4, pp. 479–486. DOI: 10.1007/s11418-015-0912-x.
Evanno L., Jossang A., Nguyen-Pouplin J. et al. Planta Med., 2008, vol. 74, no. 8, pp. 870–872. DOI: 10.1055/s-2008-1074546.
Politi M., Braca A., De Tommasi N. et al. Planta Med., 2003, vol. 69, no. 5, pp. 468–470. DOI: 10.1055/s-2003-39713.
Yoon K.D., Jeong D.G., Hwang Y.H. et al. J. Nat. Prod., 2007, vol. 70, no. 12, pp. 2029–2032. DOI: 10.1021/np070327e.
Lee M.K., Lim S.W., Yang H. et al. Bioorg Med Chem Lett., 2006, vol. 1, no. 16(11), pp. 2850–2854. DOI: 10.1016/j.bmcl.2006.03.018.
Park G., Kim S.Y., Song Y.J. PLoS One, 2017, vol. 3, no. 12(8), e0182701. DOI: 10.1371/journal.pone.0182701.
Bae K., Jin W., Thuong P.T. et al. Fitoterapia, 2007, vol. 78, no. 6, pp. 409–413. DOI: 10.1016/j.fitote.2007.02.008.
Lee J.H., Park S.Y., Hwang W. et al. Biomolecules, 2020, vol. 6, no. 10(11), 1521. DOI: 10.3390/biom10111521.
He Y.R., Shen Y.H., Li B. et al. Chem. Biodivers, 2013, vol. 10, no. 4, pp. 584–595. DOI: 10.1002/cbdv.201200105.
Ni L., Zhong X.H., Cai J. et al. Nat. Prod. Bioprospect., 2016, vol. 6, no. 3, pp. 149–154. DOI: 10.1007/s13659-016-0093-7.
Yu G.X., Wu J., Shi B.B. et al. Nat. Prod. Bioprospect., 2022, vol. 1, no. 12(1), p. 24. DOI: 10.1007/s13659-022-00344-1.
Yu G.X., Yu Y., Jing-Wu et al. Phytochemistry, 2022, vol. 200, 113220. DOI: 10.1016/j.phytochem.2022.113220.
Jiang C., Fan X., Zou D. et al. Org. Biomol. Chem., 2022, vol. 11, no. 20(18), pp. 3712–3716. DOI: 10.1039/d2ob00370h.
Song M., Xiao T., Wu Q.S. et al. Nat. Prod. Res., 2022, vol. 36, no. 12, pp. 3085–3094. DOI: 10.1080/14786419.2021.1958328.
Jiang C., Yang M., Zhao C. et al. Phytochemistry, 2022, vol. 199, 113187. DOI: 10.1016/j.phytochem.2022.113187.
Xiao S., Mu Z.Q., Cheng C.R., Ding J. Nat. Prod. Res., 2019, vol. 33, no. 3, pp. 321–327. DOI: 10.1080/14786419.2018.1448817.
Jiang C., Liu F., Yang H. et al. Phytochemistry, 2022, vol. 18, no. 204, 113436. DOI: 10.1016/j.phytochem.2022.113436.
Zhang F., Yang T., Yang K. et al. Org. Biomol. Chem., 2022, vol. 21, no. 21(1), pp. 169–178. DOI: 10.1039/d2ob01980a.
Fan Y.Y., Xu J.B., Liu H.C. et al. J. Nat. Prod., 2017, vol. 22, no. 80(12), pp. 3159–3166. DOI: 10.1021/acs.jnatprod.7b00412.
Kuo Y.H., Hwang S.Y., Yang Kuo L.M. et al. Chem. Pharm. Bull., 2002, vol. 50, no. 12, pp. 1607–1608. DOI: 10.1248/cpb.50.1607.
Wang L.W., Su H.J., Yang S.Z. et al. J. Nat. Prod., 2004, vol. 67, no. 7, pp. 1182–1185. DOI: 10.1021/np0498657.
Zhou X., Shang J., Qin M. et al. Molecules, 2019, vol. 19, no. 24(18), 3402. DOI: 10.3390/molecules24183402.
Cui J.J., Li W.J., Wang C.L. et al. Phytochemistry, 2022, vol. 201, 113278. DOI: 10.1016/j.phytochem.2022.113278.
Xiao M., Huang M., Huan W. et al. Oxid. Med. Cell Longev, 2022, vol. 14, no. 2022, 4472751. DOI: 10.1155/2022/4472751.
Quan W., Xu Y., Xie Y. et al. Molecules, 2022, vol. 27, no. 17, 5560. DOI: 10.3390/molecules27175560.
Duan F.F., Jia S.S., Yuan K. Pharmacogn. Mag., 2017, vol. 13, no. 51, pp. 351–357. DOI: 10.4103/pm.pm_286_16.
Li X.Q, Jia S.S., Yuan K., Jin S.H. Biomed. Res. Int., 2022, 5648896. DOI: 10.1155/2022/5648896.
Zhu M.F., Tu Z.C., Zhang L., Liao H. J. Food Biochem., 2019, vol. 43, no. 12, e13043. DOI: 10.1111/jfbc.13043.
Cui H.X., Duan F.F., Jia S.S. et al. Biomed. Res. Int., 2018, vol. 18, 5314320. DOI: 10.1155/2018/5314320.
Ni L., Shi W.Y. Iran J. Pharm. Res., 2014, vol. 13, no. 1, pp. 221–226.
Chen B.Q., Cui X.Y., Zhao X. et al. Fitoterapia, 2006, vol. 77, no. 4, pp. 262–267. DOI: 10.1016/j.fitote.2006.03.019.
Saeed M.K., Deng Y., Dai R. et al. J. Ethnopharmacol., 2010, vol. 127, no. 2, pp. 414–418. DOI: 10.1016/j.jep.2009.10.024.
Chen Z., Chen Z., Hou L. et al. Zhong Yao Cai, 2000, vol. 23, no. 9, pp. 551–553.
Liu M., Veryser C., Lu J.G. et al. J. Ethnopharmacol., 2018, vol. 5, no. 224, pp. 421–428. DOI: 10.1016/j.jep.2018.06.026.
Li H., Tang Y., Liang K.Y. et al. Phytochemistry, 2022, vol. 198, 113161. DOI: 10.1016/j.phytochem.2022.113161.
Koh E., Kim B., Choi K. BMC Complement Med. Ther. 2021, vol. 21, no. 1, p. 255. DOI: 10.1186/s12906-021-03429-5.
Kang M.S., Kim S., Kim D.S. et al. PLoS One, 2023, vol. 6, no. 18(2), e0281141. DOI: 10.1371/journal.pone.0281141.
Endo Y., Osada Y., Kimura F., Fujimoto K. Nutrition, 2006, vol. 22, no. 5, pp. 553–558. DOI: 10.1016/j.nut.2005.08.012.
Ryu Y.B., Jeong H.J., Kim J.H. et al. Bioorg. Med. Chem., 2010, vol. 15, no. 18(22), pp. 7940–7947. DOI: 10.1016/j.bmc.2010.09.035.
Bae J., Kwon H.J., Park J.S. et al. Curr. Issues Mol. Biol., 2023, vol. 9, no. 45(3), pp. 2284–2295. DOI: 10.3390/cimb45030147.
Jang Y.P., Kim S.R., Kim Y.C. Planta Med., 2001, vol. 67, no. 5, pp. 470–472. DOI: 10.1055/s-2001-15804.
Kim S.H., Park J.G., Hong Y.D. et al. J. Ethnopharmacol., 2016, vol. 21, no. 188, pp. 167–176. DOI: 10.1016/j.jep.2016.05.008.
Oh J., Rho H.S., Yang Y. et al. Mediators Inflamm, 2013, 761506. DOI: 10.1155/2013/761506.
Chen S.P., Dong M., Kita K. et al. Mol. Med. Rep., 2010, vol. 3, no. 4, pp. 673–678. DOI: 10.3892/mmr_00000315.
Yao X., Zhu F., Zhao Z. et al. J. Cell Biochem., 2011, vol. 112, no. 10, pp. 2837–2849. DOI: 10.1002/jcb.23198.
Jang Y.P., Kim S.R., Choi Y.H. et al. J. Neurosci. Res. 2002, vol. 15, no. 68(2), pp. 233–240. DOI: 10.1002/jnr.10204.
Kim S.H., Jang Y.P., Sung S.H. et al. Biol. Pharm. Bull., 2003, vol. 26, no. 8, pp. 1202–1205. DOI: 10.1248/bpb.26.1202.
Barradas-Dermitz D.M., Hayward-Jones P.M., Mata-Rosas M. et al. Biocell, 2010, vol. 34, no. 1, pp. 1–6.
Wang S.S., Abd El-Razek M.H., Chen Y.C. et al. Chem. Biodivers., 2009, vol. 6, no. 12, pp. 2255–2262. DOI: 10.1002/cbdv.200900003.
Shen Y.C., Wang S.S., Chien C.T. et al. J. Nat. Prod., 2008, vol. 71, no. 4, pp. 576–580. DOI: 10.1021/np078016r.
Shen Y.C., Wang S.S., Pan Y.L. et al. J. Nat. Prod., 2002, vol. 65, no. 12, pp. 1848–1852. DOI: 10.1021/np0202273.
Klein L.L., Li L., Maring C.J. et al. J. Med. Chem., 1995, vol. 28, no. 38(9), pp. 1482–1492. DOI: 10.1021/jm00009a009.
Koyama J., Morita I., Kobayashi N. et al. Biol. Pharm. Bull., 2006, vol. 29, no. 11, pp. 2310–2312. DOI: 10.1248/bpb.29.2310.
Ueda J.Y., Awale S., Tezuka Y. et al. Planta Med., 2006, vol. 72, no. 13, pp. 1241–1244. DOI: 10.1055/s-2006-947197.
Banskota A.H., Nguyen N.T., Tezuka Y. et al. Phytomedicine, 2006, vol. 13, no. 1-2, pp. 109–114. DOI: 10.1016/j.phymed.2004.01.015.
Yin J., Tezuka Y., Shi L. et al. Phytomedicine, 2006, vol. 13, no. 1-2, pp. 37–42. DOI: 10.1016/j.phymed.2004.06.017.
Nguyen N.T., Banskota A.H., Tezuka Y. et al. Planta Med., 2004, vol. 70, no. 1, pp. 29–33. DOI: 10.1055/s-2004-815451.
Hafezi K., Hemmati A.A., Abbaszadeh H. et al. Phytother. Res., 2020, vol. 34, no. 6, pp. 1397–1408. DOI: 10.1002/ptr.6613.
Sun L., Ding S., Luo Q. et al. Front Pharmacol., 2021, vol. 16, no. 12, 736442. DOI: 10.3389/fphar.2021.736442.
Sharma H., Garg M. J. Integr. Med., 2015, vol. 13, no. 2, pp. 80–90. DOI: 10.1016/S2095-4964(15)60161-3.
Li F., Li Y., Li Q., Shi X. Biomed Pharmacother, 2020, vol. 132, 110866. DOI: 10.1016/j.biopha.2020.110866.
Sharma H., Garg M. Indian J. Pharmacol., 2015, vol. 47, no. 3, pp. 299–303. DOI: 10.4103/0253-7613.157128.
Dang P.H., Nguyen H.X., Nguyen H.H.T. et al. J. Nat. Prod., 2017, vol. 23, no. 80(6), pp. 1876–1882. DOI: 10.1021/acs.jnatprod.7b00171.
Nisar M., Khan I., Ahmad B. et al. J. Enzyme Inhib Med. Chem., 2008, vol. 23, no. 2, pp. 256–260. DOI: 10.1080/14756360701505336.
Dang P.H., Nguyen H.X., Duong T.T.T. et al. J. Nat. Prod., 2017, vol. 28, no. 80(4), pp. 1087–1095. DOI: 10.1021/acs.jnatprod.7b00006.
Khan I., Nisar M., Shah M.R. et al. Fitoterapia, 2011, vol. 82, no. 7, pp. 1003–1007. DOI: 10.1016/j.fitote.2011.06.003.
Nisar M., Khan I., Simjee S.U. et al. J. Ethnopharmacol., 2008, vol. 28, no. 116(3), pp. 490–494. DOI: 10.1016/j.jep.2007.12.021.
Bhukya B., Alam S., Chaturvedi V. et al. Curr Top Med. Chem., 2021, vol. 21, no. 9, pp. 767–776. DOI: 10.2174/1568026620666200528155236.
Lee C.G., Lee J., Lee D.G. et al. Int. J. Biol. Macromol., 2016, vol. 85, pp. 505–513. DOI: 10.1016/j.ijbiomac.2016.01.027.
Zhang D., Meng H., Yang H.S. Int. J. Biol. Macromol., 2012, vol. 50, no. 3, pp. 720–724. DOI: 10.1016/j.ijbiomac.2011.12.020.
Jiang P., Zhang Q., Zhao Y. et al. Molecules, 2019, vol. 24, no. 16, 2926. DOI: 10.3390/molecules24162926.
Jiang S., Zhang Y., Zu Y. et al. Am. J. Chin. Med., 2010, vol. 38, no. 6, pp. 1107–1114. DOI: 10.1142/S0192415X10008500.
Elansary H.O., Szopa A., Kubica P. et al. Molecules, 2019, vol. 24, no. 3, 412. DOI: 10.3390/molecules24030412.
Pilija V., Djurendic-Brenesel M., Miletic S. Forensic Sci. Int., 2018, vol. 290, pp. e1–e4. DOI: 10.1016/j.forsciint.2018.07.017.
Reijnen G., Bethlehem C., van Remmen J.M.B.L. et al. J. Forensic Leg. Med., 2017, vol. 52, pp. 56–61. DOI: 10.1016/j.jflm.2017.08.016.
Küpeli E., Erdemoğlu N., Yeşilada E., Sener B. J. Ethnopharmacol., 2003, vol. 89, no. 2-3, pp. 265–270. DOI: 10.1016/j.jep.2003.09.005.
Dumitraş D.A., Bunea A., Vodnar D.C. et al. Antioxidants, 2022, vol. 11, no. 6, 1039. DOI: 10.3390/antiox11061039.
Dumitraş D.-A., Dreanca A.I., Pall E., Gal A.F., Rus V., Morohoschi A.G., Cotul M., Nan M.I., Andrei S. Antioxi-dants, 2022, vol. 11(1), 2264. DOI: 10.3390/antiox11112264.
Gotaskie G.E., Andreassi B.F. Cancer Pract., 1994, vol. 2, no. 1, pp. 27–33.
Potemski P., Płuzańska A. Pol Merkur Lekarski, 1999, vol. 6, no. 31, pp. 27–29.
Manzano A., Roig T., Bermúdez J., Bartrons R. Am. J. Physiol., 1996, vol. 271(6Pt1), pp. 1957–1962. DOI: 10.1152/ajpcell.1996.271.6.C1957.
Su H.J., Day S.H., Yang S.Z. et al. J. Nat. Prod., 2002, vol. 65, no. 1, pp. 79–81. DOI: 10.1021/np010355b.
Chen H.-L., Wang L.-W., Su H.-J. Org. Lett., 2006, vol. 16, no. 8(4), pр. 753–756. DOI: 10.1021/ol053029m.
Ettouati L., Ahond A., Poupat Ch. et al. Compton, 2007, hal-00149297f.
Li H., Liang Yu-Ru, Chen Sh.-X. et al. J. Nat. Prod., 2020, vol. 24, no. 83(7), pр. 2129–2144. DOI: 10.1021/acs.jnatprod.0c00064.
Li S.H., Zhang H.J., Niu X.M. et al. J. Nat. Prod., 2003, vol. 66, no. 7, pр. 1002–1005. DOI: 10.1021/np030117b.
Wang D.Z., Ma G.E., Xu R.S. Yao Xue Xue Bao, 1992, vol. 27, no. 3, pp. 173–177.
Kobayashi J., Yoshinaga M., Yoshida N. et al. J. Org. Chem., 2002, vol. 5, no. 67(7), pp. 2283–2286. DOI: 10.1021/jo016327f.
Cisowski W., Mazol I., Gleńsk M. Acta Pol. Pharm., 2005, vol. 62, no. 6, pp. 461–463.
Ni G., Zhang H., Fan Y.Y. et al. Org. Lett., 2016, vol. 15, no. 18(8), pp. 1880–1883. DOI: 10.1021/acs.orglett.6b00653.
Chen Z., Zheng H., Fu Q. et al. Zhongguo Zhong Yao Za Zhi, 1998, vol. 23, no. 8, pp. 456–457.
Yang C., Wang J.S., Luo J.G. et al. J. Asian Nat. Prod. Res., 2009, vol. 11, no. 6, pp. 534–538. DOI: 10.1080/10286020902932690.
Zamir L.O., Nedea M.E., Zhou Z.H. et al. Phytochemistry, 1996, vol. 41, no. 3, pp. 803–805. DOI: 10.1016/0031-9422(95)00706-7.
Shi Q.W., Si X.T., Zhao Y.M. et al. Biosci. Biotechnol. Biochem., 2006, vol. 70, no. 3, pp. 732–736. DOI: 10.1271/bbb.70.732.
Shi Q.W., Sauriol F., Mamer O., Zamir L.O. Chem. Commun., 2003, vol. 7, no. 1, pp. 68–69. DOI: 10.1039/b209312j.
Zhang J., Sauriol F., Mamer O., Zamir L.O. Phytochemistry, 2000, vol. 54, no. 2, pp. 221–230. DOI: 10.1016/s0031-9422(00)00079-0.
Bourbeau G. Laval Med., 1954, vol. 19, no. 5, pp. 637–695.
Su J., Zhang M.L., Huo C.H. et al. Zhong Yao Cai, 2013, vol. 36, no. 8, pp. 1267–1270.
Bhardwaj V. Adv. Exp. Med. Biol., 2023, vol. 1370, pp. 145–153. DOI: 10.1007/5584_2023_772.
Barboni L., Gariboldi P., Torregiani E. et al. J. Nat. Prod., 1995, vol. 58(6), pp. 934–939. DOI: 10.1021/np50120a019.
Chattopadhyay S.K., Tripathi V., Sharma R.P. et al. Phytochemistry, 1999, vol. 50, no. 1, pp. 131–133. DOI: 10.1016/s0031-9422(98)00461-0.
Madhusudanan K.P., Chattopadhyay S.K., Tripathi V.K. et al. Biomed Chromatogr., 2002, vol. 16, no. 5, pp. 343–355. DOI: 10.1002/bmc.163.
Li X., Xiong Y., Yu C., Zhang C. Se Pu, 2010, vol. 28, no. 11, pp. 1067–1070.
Choudhary M.I., Khan A.M., Habib-ur-Rehman et al. Chem. Pharm. Bull., 2002, vol. 50, no. 11, pp. 1488–1490. DOI: 10.1248/cpb.50.1488.
Stefanowicz P., Prasain J.K., Yeboah K.F., Konishi Y. Anal. Chem., 2001, vol. 1, no. 73(15), pp. 3583–3589. DOI: 10.1021/ac010254i.
Bulgakov V.P., Tchernoded G.K., Veselova M.V. et al. Biotechnol. Lett., 2011, vol. 33, no. 9, pp. 1879–1883. DOI: 10.1007/s10529-011-0632-6.
Asif M., Rizwani G.H., Zahid H. et al. Pak. J. Pharm. Sci., 2016, vol. 29, no. 1, pp. 105–109.
Tabaszewska M., Antoniewska A., Rutkowska J. et al. Molecules, 2021, vol. 24, no. 26(15), 4474. DOI: 10.3390/molecules26154474.
Stefanović M., Ristić M., Popović Z. et al. Chem. Biodivers, 2016, vol. 13, no. 7, pp. 943–953. DOI: 10.1002/cbdv.201500326.
Madrigal R.V., Smith C.R. Jr. Lipids, 1975, vol. 10, no. 8, pp. 502–504. DOI: 10.1007/BF02532438.
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