Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum)Click to copy article linkArticle link copied!
Abstract
This is the first report showing that kava lactones are plant and plant fungus growth inhibitors. Aqueous extract of kava roots showed high allelopathic potential and strongly suppressed germination and growth of lettuce, radish, barnyardgrass, and monochoria. Nine kava lactones were detected using GC-MS including desmethoxyyagonin, kavain, 7,8-dihydrokavain, hydroxykavain, yagonin, 5,6,7,8-tetrahydroxyyagonin, methysticin, dihydromethysticin, and 11-hydroxy-12-methoxydihydrokavain. Quantities of desmethoxyyagonin, kavain, 7,8-dihydrokavain, yagonin, methysticin, and dihydromethysticin detected were 4.3, 6.9, 18.6, 5.7, 1.4, and 5.4 mg/g of dry weight, respectively. These six major lactones in kava roots showed great herbicidal and antifungal activities. Growth of lettuce and barnyardgrass were significantly inhibited at 1−10 ppm, and four plant fungi including Colletotrichum gloeosporides, Fusarium solani, Fusarium oxysporum, and Trichoderma viride were significantly inhibited at 10−50 ppm. The biological activities of kava lactones were characterized by different double-bond linkage patterns in positions 5,6 and 7,8. The findings of this study suggest that kava lactones may be useful for the development of bioactive herbicides and fungicides.
Keywords: Fungicide; herbicide; inhibition; kava roots; kava lactones; plant fungi; weeds
*
Corresponding author (telephone/fax 81-98-895-8734; e-mail [email protected]).
Cited By
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
This article is cited by 29 publications.
- Chen Yang, Shengxin Sun, Wei Li, Yushuai Mao, Qiao Wang, Yabing Duan, René Csuk, Shengkun Li. Bioactivity-Guided Subtraction of MIQOX for Easily Available Isoquinoline Hydrazides as Novel Antifungal Candidates. Journal of Agricultural and Food Chemistry 2023, 71
(30)
, 11341-11349. https://doi.org/10.1021/acs.jafc.3c02096
- Warot Chotpatiwetchkul, Nawasit Chotsaeng, Chamroon Laosinwattana, Patchanee Charoenying. Structure–Activity Relationship Study of Xanthoxyline and Related Small Methyl Ketone Herbicides. ACS Omega 2022, 7
(33)
, 29002-29012. https://doi.org/10.1021/acsomega.2c02704
- Zihui Yang, Yue Sun, Qingsong Liu, Aliang Li, Wenyan Wang, Wen Gu. Design, Synthesis, and Antifungal Activity of Novel Thiophene/Furan-1,3,4-Oxadiazole Carboxamides as Potent Succinate Dehydrogenase Inhibitors. Journal of Agricultural and Food Chemistry 2021, 69
(45)
, 13373-13385. https://doi.org/10.1021/acs.jafc.1c03857
- Yuan-Yuan Wu, Wu-Bin Shao, Jian-Jun Zhu, Zhou-Qing Long, Li-Wei Liu, Pei-Yi Wang, Zhong Li, Song Yang. Novel 1,3,4-Oxadiazole-2-carbohydrazides as Prospective Agricultural Antifungal Agents Potentially Targeting Succinate Dehydrogenase. Journal of Agricultural and Food Chemistry 2019, 67
(50)
, 13892-13903. https://doi.org/10.1021/acs.jafc.9b05942
- Nawasit Chotsaeng, Chamroon Laosinwattana, Patchanee Charoenying. Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.. ACS Omega 2019, 4
(24)
, 20748-20755. https://doi.org/10.1021/acsomega.9b03144
- Ryota Ochi, Hisashi Nishiwaki, Satoshi Yamauchi. 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. Journal of Agricultural and Food Chemistry 2019, 67
(45)
, 12558-12564. https://doi.org/10.1021/acs.jafc.9b05507
- Tran Dang Xuan, Tsuneaki Toyama, Masakazu Fukuta, Tran Dang Khanh and Shinkichi Tawata. Chemical Interaction in the Invasiveness of Cogongrass (Imperata cylindrica (L.) Beauv.). Journal of Agricultural and Food Chemistry 2009, 57
(20)
, 9448-9453. https://doi.org/10.1021/jf902310j
- Róbson R. Teixeira, Luiz C. A. Barbosa, Giuseppe Forlani, Dorila Piló-Veloso and José Walkimar de Mesquita Carneiro. Synthesis of Photosynthesis-Inhibiting Nostoclide Analogues. Journal of Agricultural and Food Chemistry 2008, 56
(7)
, 2321-2329. https://doi.org/10.1021/jf072964g
- Kento Tamada, Hisashi Nishiwaki, Satoshi Yamauchi. Syntheses of (S)- and (R)-dihydromethysticin from two yeast-reduction products, which can be prepared from one racemic compound. Phytochemistry Letters 2024, 60 , 143-147. https://doi.org/10.1016/j.phytol.2024.02.001
- Xin Luo, Yifang Chen, Yu Wang, Zhifu Xing, Ju Peng, Jixiang Chen. Design, synthesis and antifungal activity of novel amide derivatives containing a pyrrolidine moiety as potential succinate dehydrogenase inhibitors. Molecular Diversity 2024, 28
(2)
, 805-816. https://doi.org/10.1007/s11030-023-10622-w
- Quy Nguyen, Cuong Quoc Nguyen, Quang De Tran, Dang Quang Le, Thi Buu Hue Bui. 1,3,4-Oxadiazole derivatives as potent antifungal agents: Synthesis, biological evaluation and an in silico study. CTU Journal of Innovation and Sustainable Development 2023, 15
(3)
, 125-129. https://doi.org/10.22144/ctujoisd.2023.057
- Zhongzhong Yan, Siyuan Liu, Longjian Qiu, Yan Chen, Aijun Li, Zihan Wang, Taopeng Chang, Xinzhe Niu, Feng Jin. Design, synthesis, and antifungal activity of nicotinamide derivatives containing diphenylamine moieties. Journal of Chemical Sciences 2022, 134
(3)
https://doi.org/10.1007/s12039-022-02081-x
- Huiling Zhu, Peng Liu, Hongxin Liu, Ebrahim-Alkhalil M. A. Ahmed, Xingen Hu, Juan Li, Hong-Ping Xiao, Xinhua Li, Jun Jiang. Asymmetric synthesis of δ-substituted-β-keto esters and β-substituted ketones
via
carboxyl-assisted site- and enantio-selective addition reactions. Organic Chemistry Frontiers 2022, 9
(10)
, 2766-2772. https://doi.org/10.1039/D2QO00280A
- Marcin Luczynski, Agnieszka Kudelko. Synthesis and Biological Activity of 1,3,4-Oxadiazoles Used in Medicine and Agriculture. Applied Sciences 2022, 12
(8)
, 3756. https://doi.org/10.3390/app12083756
- Diego Cárdenas-Laverde, Sebastián Rincón-Aceldas, Ericsson Coy-Barrera. Identification of Antifungal Compounds from
Piper
Plants Against
Fusarium oxysporum
: An Untargeted Metabolite Profiling-Based Approach. Natural Product Communications 2022, 17
(4)
https://doi.org/10.1177/1934578X221089995
- Ryota Ochi, Kaori Yoneyama, Hisashi Nishiwaki, Satoshi Yamauchi. Structure–activity relationship of the aromatic moiety of 6-substituted 5,6-dihydro-2
H
-pyran-2-one to find the novel compound showing higher plant growth inhibitory activity. Bioscience, Biotechnology, and Biochemistry 2022, 86
(2)
, 165-169. https://doi.org/10.1093/bbb/zbab185
- Jianjun Zhu, Yazhen Chen, Fen Su, Peiyi Wang, . Synthesis of Novel Thiazolyl Hydrazine Derivatives and Their Antifungal Activity. Journal of Chemistry 2021, 2021 , 1-8. https://doi.org/10.1155/2021/6563871
- Ramoagi T. Segone, Sidonie Y. Tankeu, Weiyang Chen, Sandra Combrinck, Mathias Schmidt, Alvaro Viljoen. Rapid differentiation of Piper methysticum (kava) plant parts using single point and imaging vibrational spectroscopy. Journal of Applied Research on Medicinal and Aromatic Plants 2020, 16 , 100235. https://doi.org/10.1016/j.jarmap.2019.100235
- Truong Van, Tran Xuan, Truong Minh, Nguyen Quan. Isolation and Purification of Potent Growth Inhibitors from Piper methysticum Root. Molecules 2018, 23
(8)
, 1907. https://doi.org/10.3390/molecules23081907
- Phung Tuyen, Tran Xuan, Truong Tu Anh, Truong Mai Van, Ateeque Ahmad, Abdelnaser Elzaawely, Tran Khanh. Weed Suppressing Potential and Isolation of Potent Plant Growth Inhibitors from Castanea crenata Sieb. et Zucc. Molecules 2018, 23
(2)
, 345. https://doi.org/10.3390/molecules23020345
- Urbano Osorio-Nieto, Laura Y. Vázquez-Amaya, Herbert Höpfl, Leticia Quintero, Fernando Sartillo-Piscil. The direct and highly diastereoselective synthesis of 3,4-epoxy-2-piperidones. Application to the total synthesis and absolute configurational assignment of 3α,4α-epoxy-5β-pipermethystine. Organic & Biomolecular Chemistry 2018, 16
(1)
, 77-88. https://doi.org/10.1039/C7OB02700A
- Enrico Rolli, Matteo Marieschi, Silvia Maietti, Alessandra Guerrini, Alessandro Grandini, Gianni Sacchetti, Renato Bruni. Phytotoxic Effects and Phytochemical Fingerprinting of Hydrodistilled Oil, Enriched Fractions, and Isolated Compounds Obtained from
Cryptocarya massoy
(
Oken) Kosterm
. Bark. Chemistry & Biodiversity 2016, 13
(1)
, 66-76. https://doi.org/10.1002/cbdv.201500010
- T. K. Lim. Piper methysticum. 2016, 147-196. https://doi.org/10.1007/978-3-319-26062-4_15
- Suresh Walia, Supradip Saha, Virendra S. Rana. Phytochemical Pesticides. 2014, 295-322. https://doi.org/10.1007/978-81-322-2006-0_15
- . References. 2014, 1075-1473. https://doi.org/10.1016/B978-0-12-416677-6.00026-3
- Karim Hosni, Imed Hassen, Houcine Sebei, Hervé Casabianca. Secondary metabolites from Chrysanthemum coronarium (Garland) flowerheads: Chemical composition and biological activities. Industrial Crops and Products 2013, 44 , 263-271. https://doi.org/10.1016/j.indcrop.2012.11.033
- Tran Dang Xuan, Masakazu Fukuta, Ao Chang Wei, Abdelnaser Abdelghany Elzaawely, Tran Dang Khanh, Shinkichi Tawata. Efficacy of extracting solvents to chemical components of kava (Piper methysticum) roots. Journal of Natural Medicines 2008, 62
(2)
, 188-194. https://doi.org/10.1007/s11418-007-0203-2
- Shinkichi Tawata, Masakazu Fukuta, Tran Dang Xuan, Farah Deba. Total utilization of tropical plants Leucaena leucocephala and Alpinia zerumbet. Journal of Pesticide Science 2008, 33
(1)
, 40-43. https://doi.org/10.1584/jpestics.R07-10
- T D KHANH, I M CHUNG, S TAWATA, T D XUAN. Weed suppression by
Passiflora edulis
and its potential allelochemicals. Weed Research 2006, 46
(4)
, 296-303. https://doi.org/10.1111/j.1365-3180.2006.00512.x
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.