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Comprehensive characterization of polyacetylenes and diterpenes from the underground parts of Solidago altissima L. and their contribution to the overall allelopathic activity
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Nishidono, Yuto, Tanaka, Ken (2022): Comprehensive characterization of polyacetylenes and diterpenes from the underground parts of Solidago altissima L. and their contribution to the overall allelopathic activity. Phytochemistry (112986) 193: 1-9, DOI: 10.1016/j.phytochem.2021.112986, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112986
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References
- Bohlmann, F., Burkhardt, T., 1972. Biogenesis of matricaria ester. Chem. Ber. 105, 521-528. https://doi.org/10.1002/cber.19721050217.
- Bohlmann, F., Singh, P., Singh, R.K., Joshi, K.C., Jakupovic, J., 1985. A diterpene with a new carbon skeleton from Solidago altissima. Phytochemistry 24, 1114-1115. https://doi.org/10.1016/S0031-9422(00)83202-1.
- Bohlmann, F., Zdero, C., Robinson, H., King, R.M., 1979. New acetylenic derivatives from Chrysothamnus parryi. Phytochemistry 18, 1519-1521. https://doi.org/10.1016/ S0031-9422(00)98487-5.
- Busta, L., Yim, W.C., LaBrant, E.W., Wang, P., Grimes, L., Malyszka, K., Cushman, J.C., Santos, P., Kosma, D.K., Cahoon, E.B., 2018. Identification of genes encoding enzymes catalyzing the early steps of carrot polyacetylene biosynthesis. Plant Physiol. 178, 1507-1521. https://doi.org/10.1104/pp.18.01195.
- Christensen, L.P., Lam, J., 1991. Acetylenes and related compounds in Asteraceae. Phytochemistry 30, 2453-2476. https://doi.org/10.1016/0031-9422(91)85085-E.
- Csupor-Loffler ¨, B., Hajdu, Z., Zupk´o, I., Moln´ar, J., Forgo, P., Vasas, A., Kele, Z., Hohmann, J., 2011. Antiproliferative constituents of the roots of Conyza canadensis. Planta Med. 77, 1183-1188. https://doi.org/10.1055/s-0030-1270714.
- da Silva, B.P., Nepomuceno, M.P., Varela, R.M., Torres, A., Molinillo, J.M.G., Alves, P.L. C.A., Macias, F.A., 2017. Phytotoxicity study on Bidens sulphurea Sch. Bip. as a preliminary approach for weed control. J. Agric. Food Chem. 65, 5161-5172. https://doi.org/10.1021/acs.jafc.7b01922.
- Deevanhxay, P., Suzuki, M., Maeshibu, N., Li, H., Tanaka, K., Hirose, S., 2009. Simultaneous characterization of quaternary alkaloids, 8-oxoprotoberberine alkaloids, and a steroid compound in Coscinium fenestratum by liquid chromatography hybrid ion trap time-of-flight mass spectrometry. J. Pharmaceut. Biomed. Anal. 50, 413-425. https://doi.org/10.1016/j.jpba.2009.05.023.
- Du, Y., Pearce, K.C., Dai, Y., Krai, P., Dalal, S., Cassera, M.B., Goetz, M., Crawford, T.D., Kingston, D.G.I., 2017. Antiplasmodial sesquiterpenoid lactones from Trichospira verticillata: structure elucidation by spectroscopic methods and comparison of experimental and calculated ECD data. J. Nat. Prod. 80, 1639-1647. https://doi.org/ 10.1021/acs.jnatprod.7b00247.
- Etterson, J.R., Delf, D.E., Craig, T.P., Ando, Y., Ohgushi, T., 2008. Parallel patterns of clinal variation in Solidago altissima in its native range in central USA and its invasive range in Japan. Botany 86, 91-97. https://doi.org/10.1139/B07-115.
- Ichihara, K., Kawai, T., Noda, M., 1978. Polyacetylenes of Solidago altissima L. Agric. Biol. Chem. 42, 427-431. https://doi.org/10.1271/bbb1961.42.427.
- Jente, R., Richter, E., 1976. Biosynthesis of dehydromatricaria esters. Phytochemistry 15, 1673-1679. https://doi.org/10.1016/S0031-9422(00)97451-X.
- Jin, H., Ogino, K., Fujioka, T., Yoshida, M., Ishimaru, K., 2008. A new acylphloroglucinol glycoside from Solidago altissima L. J. Nat. Med. 62, 199-201. https://doi.org/ 10.1007/s11418-007-0215-y.
- Jin, H., Tanaka, T., Kouno, I., Ishimaru, K., 2007. A new kaempferol trioside from Solidago altissima L. J. Nat. Med. 61, 351-354. https://doi.org/10.1007/s11418-007- 0139-6.
- Johnson, R.H., Halitschke, R., Kessler, A., 2010. Simultaneous analysis of tissue- and genotype-specific variation in Solidago altissima (Asteraceae) rhizome terpenoids, and the polyacetylene dehydromatricaria ester. Chemoecology 20, 255-264. https:// doi.org/10.1007/s00049-010-0055-1.
- Kato, A., Ohbayashi, N., 2009. Habitat expansion of an exotic lace bug, Corythucha marmorata (uhler) (Hemiptera: tingidae), on the kii peninsula and shikoku island in western Japan. Entomol. Sci. 12, 130-134. https://doi.org/10.1111/j.1479- 8298.2009.00313.x.
- Kato-Noguchi, H., Kosemura, S., Yamamura, S., 1998. Allelopathic potential of 5-chloro- 6-methoxy-2-benzoxazolinone. Phytochemistry 48, 433-435. https://doi.org/ 10.1016/S0031-9422(98)00029-6.
- Kobayashi, A., Kouya, S., Yamashita, K., 1976. Synthesis of a new acetylenic compound isolated from Solidago altissima. Agric. Biol. Chem. 40, 2257-2260. https://doi.org/ 10.1271/bbb1961.40.2257.
- Kobayashi, A., Morimoto, S., Shibata, Y., Yamashita, K., Numata, M., 1980. C10- Polyacetylenes as allelopathic substances in dominants in early stages of secondary succession. J. Chem. Ecol. 6, 119-131. https://doi.org/10.1007/BF00987532.
- Kurisawa, N., Yukawa, M., Koshino, H., Onodera, T., Toda, T., Kimura, K., 2020. Kolavenic acid analog restores growth in HSET-overproducing fission yeast cells and multipolar mitosis in MDA-MB-231 human cells. Bioorg. Med. Chem. 28, 115154. https://doi.org/10.1016/j.bmc.2019.115154.
- Lawson, S.K., Sharp, L.G., Powers, C.N., McFeeters, R.L., Satyal, P., Setzer, W.N., 2020. Volatile compositions and antifungal activities of Native American medicinal plants: focus on the Asteraceae. Plants 9, 126. https://doi.org/10.3390/plants9010126.
- Lu, T., Cantrell, C.L., Robbs, S.L., Franzblau, S.G., Fischer, N.H., 1998. Antimycobacterial matricaria esters and lactones from Astereae species. Planta Med. 64, 665-667. https://doi.org/10.1055/s-2006-957547.
- Minto, R.E., Blacklock, B.J., 2008. Biosynthesis and function of polyacetylenes and allied natural products. Prog. Lipid Res. 47, 233-306. https://doi.org/10.1016/j. plipres.2008.02.002.
- Morimoto, M., 2019. Chemical defense against insects in Heterotheca subaxillaris and three Orobanchaceae species using exudates from trichomes. Pest Manag. Sci. 75, 2474-2481. https://doi.org/10.1002/ps.5395.
- Nishidono, Y., Ishii, T., Okada, R., Norimoto, H., Murayama, C., He, D., Okuyama, T., Nishizawa, M., Tanaka, K., 2020. Effect of heat processing on the chemical constituents and NO-suppressing activity of Bletilla Tuber. J. Nat. Med. 74, 219-228. https://doi.org/10.1007/s11418-019-01371-y.
- Nishidono, Y., Niwa, K., Kitajima, A., Watanabe, S., Tezuka, Y., Arita, M., Takabayashi, J., Tanaka, K., 2021. α- Linolenic acid in Papilio machaon larvae regurgitant induces a defensive response in Apiaceae. Phytochemistry 188, 112796. https://doi.org/10.1016/j.phytochem.2021.112796.
- Nishino, C., Manabe, S., Kazui, M., Matsuzaki, T., 1984. Piscicidal cis -clerodane diterpenes from Solidago altissima L: absolute configurations of 5α, 10α- cis - clerodanes. Tetrahedron Lett. 25, 2809-2812. https://doi.org/10.1016/S0040-4039 (01)81296-X.
- Ochi, R., Nishiwaki, H., Yamauchi, S., 2019. Syntheses and phytotoxicity of all stereoisomers of 6-(2-hydroxy-6-phenylhex-1-yl)-5,6-dihydro-2H -pyran-2-one and determination of the effect of the α,β- unsaturated carbonyl structure and hydroxy group bonding to chiral carbon. J. Agric. Food Chem. 67, 12558-12564. https://doi. org/10.1021/acs.jafc.9b05507.
- Okada, S., Iwasaki, A., Kataoka, I., Suenaga, K., Kato-Noguchi, H., 2019. Phytotoxic activity of kiwifruit leaves and isolation of a phytotoxic substance. Sci. Hortic. 250, 243-248. https://doi.org/10.1016/j.scienta.2019.02.029.
- Okano, A., Nomura, Y., Tezuka, T., 1983. Identification of bauerenol in Solidago altissima. J. Nat. Prod. 46, 750-751. https://doi.org/10.1021/np50029a026.
- Pfeifer Barbosa, A.L., Wenzel-Storjohann, A., Barbosa, J.D., Zidorn, C., Peifer, C., Tasdemir, D., Cicek, S.S., 2019. Antimicrobial and cytotoxic effects of the Copaifera reticulata oleoresin and its main diterpene acids. J. Ethnopharmacol. 233, 94-100. https://doi.org/10.1016/j.jep.2018.11.029.
- Ren, X., He, X., Zhang, Z., Yan, Z., Jin, H., Li, X., Qin, B., 2015. Isolation, identification, and autotoxicity effect of allelochemicals from rhizosphere soils of flue-cured tobacco. J. Agric. Food Chem. 63, 8975-8980. https://doi.org/10.1021/acs. jafc.5b03086.
- Sakata, Y., Itami, J., Isagi, Y., Ohgushi, T., 2015. Multiple and mass introductions from limited origins: genetic diversity and structure of Solidago altissima in the native and invaded range. J. Plant Res. 128, 909-921. https://doi.org/10.1007/s10265-015- 0753-4.
- Salah, M.A., Bedir, E., Toyang, N.J., Khan, I.A., Harries, M.D., Wedge, D.E., 2003. Antifungal clerodane diterpenes from Macaranga monandra (L) Muell. et Arg. (Euphorbiaceae). J. Agric. Food Chem. 51, 7607-7610. https://doi.org/10.1021/ jf034682w.
- Sawabe, A., Minemoto, K., Minematsu, T., Morita, M., Ouchi, S., Okamoto, T., 1997. Characterization of the Z and E isomers of dehydromatricaria lactones. J. Jpn. Oil Chem. Soc. 46 (413-417), 459. https://doi.org/10.5650/jos1996.46.413.
- Sawabe, A., Minemoto, K., Ouchi, S., Okamoto, T., 1999. Effects of acetylenes and terpenoids from Solidago altissima L. on seed germination. J. Jpn. Oil Chem. Soc. 48, 139-142. https://doi.org/10.5650/jos1996.48.139, 151.
- Silva, M.P., Piazza, L.A., L´opez, D., Lopez ´Rivilli, M.J., Turco, M.D., Cantero, J.J., Tourn, M.G., Scopel, A.L., 2012. Phytotoxic activity in Flourensia campestris and isolation of (!)-hamanasic acid A as its active principle compound. Phytochemistry 77, 140-148. https://doi.org/10.1016/j.phytochem.2011.09.020.
- Stevens, K.L., 1986. Allelopathic polyacetylenes from Centaurea repens (Russian knapweed). J. Chem. Ecol. 12, 1205-1211. https://doi.org/10.1007/BF01012342.
- Sun, J., Song, Y.L., Zhang, J., Huang, Z., Huo, H.X., Zheng, J., Zhang, Q., Zhao, Y.F., Li, J., Tu, P.F., 2015. Characterization and quantitative analysis of phenylpropanoid amides in eggplant (Solanum melongena L.) by high-performance liquid chromatography coupled with diode array detection and hybrid ion trap time-of-flight mass spectrometry. J. Agric. Food Chem. 63, 3426-3436. https://doi.org/ 10.1021/acs.jafc.5b00023.
- Tori, M., Katto, A., Sono, M., 1999. Nine new clerodane diterpenoids from rhizomes of Solidago altissima. Phytochemistry 52, 487-493. https://doi.org/10.1016/S0031- 9422(99)00273-3.
- Tsuji, H., Tani, Y., Ueda, H., 1977. On the antibacterial substances in the roots of Solidago altissima L. Nippon Nogeikagaku Kaishi 51, 609-615. https://doi.org/10.1271/ nogeikagaku1924.51.10_609.
- Uesugi, A., Johnson, R., Kessler, A., 2019. Context-dependent induction of allelopathy in plants under competition. Oikos 128, 1492-1502. https://doi.org/10.1111/ oik.06389.
- Wu, B., Takahashi, T., Kashiwagi, T., Tebayashi, S., Kim, C.S., 2007. New flavonoid glycosides from the leaves of Solidago altissima. Chem. Pharm. Bull. 55, 815-816. https://doi.org/10.1248/cpb.55.815.
- Yukinaga, H., Ide, K., Ito, K., Shimada, M., 1975. Control of Solidago altissima with asulam. J. Weed Sci. Technol. 19, 46-50. https://doi.org/10.3719/weed.1975.46.
- Zhang, N., Song, Y., Song, Q., Shi, S., Zhang, Q., Zhao, Y., Li, J., Tu, P., 2016. Qualitative and quantitative assessments of Aconiti Lateralis Radix Praeparata using high-performance liquid chromatography coupled with diode array detection and hybrid ion trap-time-of-flight mass spectrometry. J. Chromatogr. Sci. 54, 888-901. https:// doi.org/10.1093/chromsci/bmv245.
- Zhang, Z., Guo, S.S., Zhang, W.J., Geng, Z.F., Liang, J.Y., Du, S.S., Wang, C.F., Deng, Z. W., 2017. Essential oil and polyacetylenes from Artemisia ordosica and their bioactivities against Tribolium castaneum Herbst (Coleoptera: tenebrionidae). Ind. Crop. Prod. 100, 132-137. https://doi.org/10.1016/j.indcrop.2017.02.020.