Received: 20 January 2021 Revised: 7 May 2021
DOI: 10.1111/wbm.12230
REVIEW PAPER
Phenolic allelochemicals: Achievements, limitations, and
prospective approaches in weed management
La Hoang Anh1 | Nguyen Van Quan1,2
Tran Dang Xuan1,2
1
Graduate School for International
Development and Cooperation,
Hiroshima University, Hiroshima, Japan
2
Transdisciplinary Science and
Engineering Program, Graduate School of
Advanced Science and Engineering,
Hiroshima University, Hiroshima, Japan
3
Division of Agricultural Biodiversity,
Plant Resources Center of Vietnam,
Hanoi, Vietnam
Correspondence
Tran Dang Xuan, Transdisciplinary
Science and Engineering Program,
Graduate School of Advanced Science and
Engineering, Hiroshima University,
Hiroshima 739-8529, Japan.
Email: tdxuan@hiroshima-u.ac.jp
Funding information
This research received no external funding
Communicated by Masanori Morimoto
1 | INTRODUCTION
Weed invasion is threatening biodiversity, agriculture,
and forestry all over the world (Hartzler & Buhler, 2007;
Weed Biol. Manag. 2021;21:37–67.
Accepted: 9 May 2021
| La Tuan Nghia3 |
Abstract
In recent decades, phenolic compounds derived from plants have been consid-
ered as potential weed inhibitors due to their environmentally friendly proper-
ties, which are profitable regarding sustainable development targets. While
experiments indicated that phenolic compounds exhibited significant inhibi-
tion on weeds via various biological pathways, none of these natural com-
pounds have been efficiently applied in practical agricultural production. This
paper provides an overview of the phenolic allelochemicals (and their plant
sources) that have been reported to have the most potential for weed growth
inhibition as well as their modes of action. The biosynthetic pathway, classifi-
cation, distribution, release, degradation, extraction, and isolation of these
allelochemicals are also discussed. In addition, the advantages and limitations
of applying these allelochemicals in weed management and sustainable agri-
cultural development are indicated. Accordingly, there are three promising
strategies to deal with the present problems and improve the effectiveness of
future studies, including: (a) to discover a new approach combining phenolic
allelochemicals and other prospective phytochemicals in the development of
natural herbicides; (b) to modify the chemical structure for strengthening the
stability and activity of the target compound; and (c) to generate resistant crops
against weed stress related to the proliferation of phenolic allelochemicals
through genetic engineering approaches. Conceivably, the information on phe-
nolic allelochemicals that is assembled in this paper may provide a useful
dataset for future studies on the application of artificial intelligence in the
design and production of efficient natural herbicides for weed management
and sustainable agricultural development.
KEYWORDS
allelopathy, allelopathic plant, phenolic allelochemicals, sustainable agricultural
development, weed management
Jose, Kohli, Singh, Batish, & Pieterson, 2008; Vitousek,
D'Antonio, Loope, & Westbrooks, 1996). In agricultural
and forestry production, yield loss caused by weed stress
is considered to be higher than other biotic stresses
wileyonlinelibrary.com/journal/wbm © 2021 Weed Science Society of Japan 37
38
caused by fungi, viruses, and bacteria (Abbas, Tanaka,
Duke, & Boyette, 1995). The most popular solutions for
weed management are hand weeding, mechanical
weeding, and herbicide. Currently, herbicides have been
increasingly used to control weeds, particularly in devel-
oping countries (Zhang, 2003).
Weed management without herbicide is often consid-
ered impossible. However, the overuse of herbicides is
negatively affecting the environment and human health
(Stephenson, 2003). Additionally, the long-term applica-
tion of herbicides is the cause of generating resistance to
herbicides in weeds, which is currently becoming a seri-
ous problem in the development of sustainable agricul-
ture worldwide. An increase in herbicide-resistant weeds
has been continuously reported. For example, triazines
were one of the first popular groups of herbicides, which
were applied widely due to their significant inhibition of
the photosynthesis of various weeds.
However, the frequent and inaccurate application of
triazines leads to a decrease in efficiency together with
the rapid development of triazine-resistant genes in
weeds. Currently, a total of 262 resistant weeds (152 and
110 dicots and monocots, respectively) against herbicides
have been found. Additionally, a number of 514 unique
cases (species with
site of action) have been reported—
for example, the unique case of Conyza canadensis,
which is resistant to atrazine (Group C1). C. canadensis
FIGURE 1 Allelopathic mechanism of phenolic allelochemicals [Color figure can be viewed at wileyonlinelibrary.com]
HOANG ANH ET AL.
becoming resistant to acetolactate synthase inhibitors
(Group B) is another unique case. In addition, 229 com-
mon resistant genes have been sequenced and published
worldwide (International Herbicide Resistance-Weed
Database, 2020).
These numbers are increasing, and 10 species are
causing serious yield loss of crops. There are three dan-
gerous weed species with multiple resistant genes against
herbicides, including rigid ryegrass (Lolium rigidum),
wild oat (Avena fatua), and redroot pigweed
(Amaranthus retroflexus) (International Herbicide
Resistance-Weed Database, 2020). Therefore, sustainable
solutions should be developed in advance to deal with
weed stress around the world. Recently, among the pro-
posed approaches, research on allelopathy has become
increasingly prevalent in weed management for
agroecosystems and agroforestry systems.
Allelopathy is known as a popular natural phenome-
non by which a plant impacts on the growth and develop-
ment of ambient organisms via releasing phytochemicals
into the habitat. Compounds possessing allelopathic
activities (also known as allelochemicals) are plant sec-
ondary metabolites, which have stimulatory and/or
inhibitory effects on other plants or living organisms
(Rice, 1974). Allelochemicals can be released by a plant
via volatilization, leaching, exudation, and plant residue
decomposition (Figure 1).
HOANG ANH ET AL.
Phenolics are the largest group of allelochemicals.
Phenolic compounds are synthesized via the
phenylpropanoid–acetate pathway and exhibit a wide
range of structures and allelopathic modes of action.
Based on their specific structure of carbon skeletons, phe-
nolic compounds are classified into different groups
(Tsimogiannis & Oreopoulou, 2019). The biosynthesis
and classification of phenolics are described in the next
section of this review.
Currently, the development of sustainable solutions
for weed management has met various complications. In
the context of herbicide-resistant weeds becoming serious
problems in the future, herbicides with new modes of
action are urgently needed. Fortunately, the vast diversity
and wide distribution of phenolic allelochemicals and
their plant sources offer a great opportunity to generate
natural herbicides, which can be directly applied to weed
management (Dayan & Duke, 2014). Due to the rapid
development of advanced techniques, there is a promis-
ing direction in creating resistant crops to weed stress by
genetic engineering approaches. In this paper, phenolic
allelochemicals and their potential for weed management
are comprehensively reviewed and discussed.
2 | P H E N O L IC
ALLELOCHEMICALS
Phenolic allelochemicals are abundantly found in soil;
therefore, they are considered as the most common
phytotoxins between plants (Inderjit, 1996; Khanh,
Xuan, & Chung, 2007). The popular phenolic
allelochemicals are described in Table 1, and their respec-
tive structures are shown in Figure 2. Their plants
sources and test plants are also presented in this section.
This information is useful to develop strategies for exploi-
ting the phenolic allelochemicals of plants.
3 | B IOSYNTHETIC P ATHWAY OF
P H E N O L I C A L L EL O C H E M I C A L S
Among phenolic compounds, phenolic acids and flavo-
noids are the most studied groups of allelopathic activity.
The major biosynthetic pathways of these allelochemicals
and relevant enzymes are described in Figure 3. Genes
encoding the mentioned enzymes are fully sequenced in
many crops, such as soybeans, rice, tomato, wine grape,
tobacco, and cotton.
Detailed information can be easily accessed by
searching the enzyme names in Gene Database of
National Center for Biotechnology Information (2021).
Comprehensive understandings of enzyme reactions and
39
genetic engineering may support future studies on the
proliferating phenolic allelochemical contents in plants
as well as for synthesizing such compounds and their
derivatives against noxious weeds.
4 | C L A SSI F I C A T I O N,
D I S T R I B U T I O N , RE L E A S E , AN D
DEG RADATION O F P HENOLIC
ALLELOCHEMICALS
4.1 | Classification
In allelopathic research, the classification of phenolic
compounds may not precisely determine their proper-
ties on an indicator object but can help clarify their
mechanisms of action as well as the biosynthetic path-
ways (Neilson, Goodger, Woodrow, & Møller, 2013).
The classification of phenolic allelochemicals in this
review is based on the specific rules described by
Tsimogiannis and Oreopoulou (2019). Essentially, com-
pounds containing a benzene (C6) ring linked to
hydroxyl (-OH) groups are considered as phenolics.
According to their basic carbon skeletons, phenolic
allelochemicals can be categorized as presented in
Table 1. Briefly, the categories of phenolic
allelochemicals are listed as follows:
1. (C6) compounds such as simple phenols.
2. (C6-Cn) compounds, including (C6-C1): benzoic acids and
derivatives, phenolic aldehydes; (C6-C2): phenylacetic
acids, acetophenones; (C6-C3): phenylpropanoids, cou-
marins, phenylalanine and derivatives; and (C6-C4):
naphthoquinones and phenylbutyric acids.
3. (C6-Cn-C6) compounds, comprising (C6-C2-C6):
anthraquinones; (C6-C3-C6): flavonoids.
4. Compounds with a complex structure can be referred
to as phenolic dimers and phenolic hybrids.
4.2 | Distribution
Phenolic compounds can be found in every plant (trees,
crops, medicinal plants, and weeds) (Weston &
Duke, 2003). In soil, these compounds are found abun-
dantly and appear in three forms: free, reversibly bound,
and bound allelochemicals (Li et al., 2010).
4.3 | Release
Phenolic allelochemicals can be released by every plant
part including the roots, stems, leaves, flowers, seeds, and
 40

TABLE 1 Phenolic allelochemicals

Phenolic compounds Plant sources Indicator plants References

(C6) Compounds
Simple phenols
Resorcinol (1) Zea mays Lactuca sativa (Chou & Patrick, 1976)
Phloroglucinol (2)
Catechol (3) Olea europaea Papaver rhoeas; Cirsium arvense; Lamium (Dellagreca et al., 2001; Fiorentino
amplexicaule; Sinapis arvensis; Triticum et al., 2003; Topal, Kocaçalişkan, &
vulgare; Hordeum vulgare Arslan, 2006)
Hydroquinone (4) Adenostoma fasciculatum Avena sativa; Zea mays; Abutilon (McPherson, Chou, & Muller, 1971)
theophrasti; Amaranthus retroflexus;
Panicum miliaceum
(C6-C1) Compounds
Shikimic acids and derivatives
Shikimic acid (5) Illicium verum Lactuca sativa (Aniya, Nomura, Fuerdeng, Appiah, &
Fujii, 2020)
Benzoic acids and derivatives
Benzoic acid (6) Cucumis sativus; Imperata cylindrica; Oryza Bidens pilosa; Cucumis sativus; Echinochloa (Chou & Patrick, 1976; Kuwatsuka &
sativa; Secale cereale; Zea mays crus-galli; Lactuca sativa; Leucaena Shindo, 1973; Xuan, Tsuneaki, Masakazu,
leucocaphala Tran, & Shinkichi, 2009; Yu, Ye, Zhang, &
Hu, 2003)
⍴-Hydroxybenzoic acid (7) Ageratum conyzoides; Cucumis sativus; Amaranthus retroflexus; Betula platyphylla; (Batish, Kaur, Singh, & Kohli, 2009; Chou &
Delonix regia; Litchi chinensis; Oryza Chenopodium album; Cirsium sp.; Leu, 1992; Chou & Patrick, 1976; He &
sativa; Quercus mongolica; Secale cereale; Cucumis sativus; Lactuca sativa; Lin, 2001; Li, Wang, Ruan, De Pan, &
Zea mays; Ophiopogon japonicus; Delonix Monochorea; Plantago lanceolata; Rumex Jiang, 2010; Lin et al., 2004; Lin
regia; Picea schrenkiana crispus; Solanum nigrum; Echinochloa et al., 2004; Politycka, 1997; Reigosa,
crus-galli; Sagittaria montevidensis; Souto, & Gonz
alez, 1999; Seal, Haig, &
Eleusine indica; Portulaca oleracea; Picea Pratley, 2004; Wang et al., 2013; Yu
schrenkiana et al., 2003; Yukiko, Yasuo, &
Minoru, 2001)
3,4-Dimethoxybenzoic acid (8) Quercus mongolica Betula platyphylla; Lactuca sativa (Yukiko et al., 2001)
3,4,5-Trimethoxybenzoic acid (9)
3,5-Dinitrobenzoic acid (10) Delonix regia Lactuca sativa (Chou & Leu, 1992)
Anisic acid (11) Ageratum conyzoides Oryza sativa (Batish et al., 2009)
Gallic acid (12) Ageratum conyzoides; Cucumis sativus; Cucumis sativus; Glycine max; Oryza sativa; (Batish et al., 2009; Patterson, 1981; Yu
Delonix regia; Eucalyptus spp.; Picea Picea schrenkiana; Phaseolus mungo et al., 2003; Li et al., 2010; Chou &
schrenkiana Leu, 1992; Sasikumar, Vijiaylakshmi, &
Parthiban, 2002)
HOANG ANH ET AL.
TABLE 1 (Continued)
Phenolic compounds
Gentisic acid (13)
Isovanillic acid (14)
Phthalic acid (15)
Protocatechuic acid (16)
Salicylic acid (17)
Syringic acid (18)
Vanillic acid (19)
β-Resorcylic acid (20)
Phenolic aldehydes
⍴-Hydroxybenzaldehyde (21)
3,4-Dihydroxybenzaldehyde (22)
Ethyl hematommate (23)
Grandinol (24)
Plant sources
Eucalyptus spp.; Lanta camara; Oryza
sativa; Picea schrenkiana
Imperata cylindrica
Lilium davidii
Cucumis sativus; Delonix regia; Oryza sativa;
Capsicum annuum
Cucumis sativus; dwarf lilyturf; Medicago
sativa; Oryza sativa; Quercus mongolica;
Secale cereale; Stylosanthes guianensis; Zea
mays; Ophiopogon japonicus
Avena fatua; Imperata cylindrica; Oryza
sativa; Triticum aestivum; Zea mays;
Capsicum annuum; Ophiopogon japonicus
Cucumis sativus; Oryza sativa; Picea
schrenkiana; Quercus mongolica; Secale
cereale; Triticum aestivum; Zea mays;
Ophiopogon japonicus
Picea schrenkiana
Echinochloa crus-galli; Litchi chinensis;
Quercus mongolica; Zea mays; Capsicum
annuum
Delonix regia
Picea schrenkiana
Eucalyptus grandis
Indicator plants
Picea schrenkiana; Vigna mungo; Phaseolus
mungo
Bidens pilosa; Echinochloa crus-galli;
Leucaena leucocaphala
Lactuca sativa; Lilium davidii
Cucumis sativus; Lactuca sativa;
Betula platyphylla; Cucumis sativus;
Echinochloa crus-galli; Lactuca sativa;
Medicago sativa; Monochorea; Sagittaria
montevidensis; Monochoria vaginalis;
Pyrus communis; Avena sativa; Zea mays;
Glycine max; Abutilon theophrasti;
Amaranthus retroflexus; Panicum
miliaceum
Bidens pilosa; Echinochloa crus-galli;
Lactuca sativa; Leucaena leucocaphala;
Sagittaria montevidensis; Triticum
aestivum; Vigna mungo
Amaranthus retroflexus; Amaranthus
tricolor; Betula platyphylla; Chenopodium
album; Cirsium sp.; Cucumis sativus;
Lactuca sativa; Monchoria; Picea
schrenkiana; Plantago lanceolata; Rumex
crispus; Sagittaria montevidensis; Solanum
nigrum; Vigna mungo; Glycine max
Picea schrenkiana
Betula platyphylla; Lactuca sativa
Lactuca sativa
Picea schrenkiana
Vigna radiata
References
(Hussain, Ghulam, Sher, & Ahmad, 2011;
Kuwatsuka & Shindo, 1973; Li et al., 2010;
HOANG ANH ET AL.
Sasikumar et al., 2002)
(Xuan et al., 2009)
(Wu et al., 2015)
(Chou & Leu, 1992; Kuwatsuka &
Shindo, 1973; Reigosa et al., 1999; Yu
et al., 2003)
(Chou & Patrick, 1976; Ghimire, Ghimire,
Yu, & Chung, 2019; Khanh et al., 2006;
Kuwatsuka & Shindo, 1973; Leslie &
Romani, 1988; Lin, He, et al., 2004; Lin,
Tsuzuki, et al., 2004; Seal, Haig, &
Pratley, 2004; Shettel & Balke, 1983; Yu
et al., 2003; Yukiko et al., 2001)
(Chou, Liu, & Kao, 1977; Kuwatsuka &
Shindo, 1973; Liu et al., 2016; Reigosa
et al., 1999; Seal, Haig, & Pratley, 2004;
Xuan et al., 2009)
(Chotsaeng, Laosinwattana, &
Charoenying, 2017; Chou & Patrick, 1976;
Li et al., 2010; Lin, He, et al., 2004; Lin,
Tsuzuki, et al., 2004; Mattice, Lavy,
Skulman, & Dilday, 1998; Patterson, 1981;
Reigosa et al., 1999; Seal, Haig, &
Pratley, 2004; Yu et al., 2003; Yukiko
et al., 2001)
(Li et al., 2010)
(Chou & Patrick, 1976; Reigosa et al., 1999;
Wang et al., 2013; Yukiko et al., 2001)
(Chou & Leu, 1992)
(Li et al., 2010)
(Yoneyama et al., 1996; Yoshida et al., 1988)
41
(Continues)
 42

TABLE 1 (Continued)

Phenolic compounds Plant sources Indicator plants References

Salicylaldehyde (25)
Syringaldehyde (26)
Vanillin (27)
Phenolic glycosides
Dhurrin (28)
(C6-C2) Compounds
Phenylacetic acids
Phenylacetic acid (29)
2-Hydroxyphenylacetic acid (30)
4-Hydroxyphenylacetic acid (31)
Acetophenones
4-Acetyl-2-methoxyphenol (32)
Xanthoxyline (33)
Styrenes
4-Vinylphenol (34)
Homograndinol (35)
Phenethylamines
Hordenine (36)
(C6-C3) Compounds
Cinnamic acids and derivatives
Cinnamic acid (37)
Secale cereale; Zea mays Lactuca sativa
Dwarf lilyturf; Imperata cylindrica Bidens pilosa; Echinochloa crus-galli;
Leucaena leucocaphala; Monochoria
vaginalis
Imperata cylindrica; Stylosanthes guianensis Bidens pilosa; Echinochloa crus-galli;
Leucaena leucocaphala
Sorghum halepense Lactuca sativa; Solanum lycopersicum
Secale cereale; Zea mays Lactuca sativa
Oryza sativa; Picea schrenkiana Lactuca sativa; Oryza sativa; Picea
schrenkiana; Vigna radiata
Picea schrenkiana Picea schrenkiana
Imperata cylindrica Bidens pilosa; Imperata cylindrica;
Echinochloa crus-galli; Leucaena
leucocaphala
Zanthoxylum limonella Amaranthus tricolor; Echinochloa crus-galli
Picea schrenkiana Picea schrenkiana
Eucalyptus grandis
Hordeum vulgare Amaranthus powellii; Bromus unioloide;
Sinapis alba
Citrullus lanatus; Cucumis sativus; Cuscuta Bidens pilosa; Cucumis sativus; Cucurbita
hygrophilae; Imperata cylindrica; Zea ficifolia; Echinochloa crus-galli; Glycine
mays max; Lactuca sativa; Leucaena
leucocaphala
(Chou & Patrick, 1976)
(Lin, He, et al., 2004; Lin, Tsuzuki,
et al., 2004; Xuan et al., 2009)
(Khanh et al., 2006; Xuan et al., 2009)
(Nicollier, Pope, & Thompson, 1983)
(Chou & Patrick, 1976)
(Chou et al., 1977; Li et al., 2010)
(Li et al., 2010)
(Xuan et al., 2009)
(Charoenying, Teerarak, &
Laosinwattana, 2010; Chotsaeng
et al., 2017)
(Li et al., 2010)
(Yoshida et al., 1988)
(Lovett & Hoult, 1994)
(Chou & Patrick, 1976; Ding et al., 2007; He
& Lin, 2001; Khanh et al., 2008; Li, Inoue,
Nishimura, Mizutani, & Tsuzuki, 1993;
Patterson, 1981; Xuan et al., 2009; Yu
et al., 2003)
HOANG ANH ET AL.
TABLE 1 (Continued)

Phenolic compounds Plant sources Indicator plants References

cis-Cinnamic acid (38) Spiraea thunbergii Amaranthus retroflexus; Brassica rapa; (Hiradate, Morita, Furubayashi, Fujii, &
Lactuca sativa; Phleum pretense; Trifolium Harada, 2005)
HOANG ANH ET AL.

⍴-Coumaric acid (39) Ageratum conyzoides; Cucumis sativus;
Imperata cylindrica; Medicago sativa;
Oryza sativa; Picea schrenkiana; Piper
methysticum; Quercus mongolica; Secale
cereale; Sorghum halepense; Triticum
aestivum; Zea mays
m-Coumaric acid (40) Medicago sativa; Oryza sativa
o-Coumaric acid (41) Medicago sativa; Oryza sativa; Secale cereale;
Zea mays
Caffeic acid (42) Cucumis sativus; Delonix regia; Oryza sativa;
Zea mays; Capsicum annuum
Ferulic acid (43) Ageratum conyzoides; Cucumis sativus;
Imperata cylindrica; Oryza sativa; Quercus
mongolica; Secale cereale; Triticum
aestivum; Zea mays
Isoferulic acid (44) Imperata cylindrica
Sinapic acid (45) Cucumis sativus; Oryaza sativa
Chlorogenic acid (46) Delonix regia; Quercus mongolica; Capsicum
annuum
pretense
Amaranthus retroflexus; Betula platyphylla;
Bidens pilosa; Chenopodium album;
Cirsium sp.; Cucumis sativus; Echinochloa
crus-galli; Glycine max; Lactuca sativa;
Leucaena leucocaphala; Picea schrenkiana;
Plantago lanceolata; Rumex crispus;
Sagittaria montevidensis; Solanum nigrum
Lactuca sativa
Lactuca sativa
Cucumis sativus; Glycine max; Lactuca
sativa; Phaseolus aureus; Plantago
lanceolata
Amaranthus retroflexus; Betula platyphylla;
Bidens Pilosa; Chenopodium album;
Cirsium sp.; Cucumis sativus; Ipomoea
lacunose; Lactuca sativa; Leucaena
leucocaphala; Plantago lanceolata; Rumex
crispus; Sagittaria montevidensis; Sida
spinose; Solanum nigrum; Glycine max
Bidens pilosa; Echinochloa crus-galli;
Leucaena leucocaphala
Cucumis sativus
Betula platyphylla; Lactuca sativa
(Batish et al., 2009; Chou & Patrick, 1976;
Kuwatsuka & Shindo, 1973; Li et al., 2010;
Li, Inoue, et al., 1993; Nicollier
et al., 1983; Patterson, 1981;
Politycka, 1997; Reigosa et al., 1999; Seal,
Haig, & Pratley, 2004; Wu, Pratley,
Lemerle, & Haig, 2001; Xuan et al., 2009;
Xuan, Eiji, Hiroyuki, Mitsuhiro, &
Khanh, 2003; Xuan, Tsuzuki, Terao,
Matsuo, & Khanh, 2003; Yu et al., 2003;
Yukiko et al., 2001)
(Chon & Kim, 2002; Li, Inoue, et al., 1993)
(Chon & Kim, 2002; Chou & Patrick, 1976;
Li, Inoue, et al., 1993)
(Batish, Singh, Kaur, Kohli, & Yadav, 2008;
Chou & Patrick, 1976; Kuwatsuka &
Shindo, 1973; Li, Inoue, et al., 1993;
Patterson, 1981; Reigosa et al., 1999; Yu
et al., 2003)
(Batish et al., 2009; Chou & Patrick, 1976;
He & Lin, 2001; Li, Inoue, et al., 1993;
Patterson, 1981; Politycka, 1997; Reigosa
et al., 1999; Shilling, Liebl, &
Worsham, 1985; Xuan et al., 2009; Yu
et al., 2003; Yukiko et al., 2001)
(Xuan et al., 2009)
(Kuwatsuka & Shindo, 1973; Yu et al., 2003)
(Li, Inoue, et al., 1993; Reigosa et al., 1999;
Yukiko et al., 2001)
(Continues)
43
 44

TABLE 1 (Continued)

Phenolic compounds Plant sources Indicator plants References

Phenolic glycosides
1-O-cis-Cinnamoyl-β-D-glucopyranose Spiraea thunbergii Amaranthus retroflexus; Brassica rapa; (Hiradate et al., 2005)
(47) Lactuca sativa; Phleum pretense; Trifolium
6-O-(4’-Hydroxy-20 - pretense
methylenebutyroyl)-1-O-cis-
cinnamoyl-β-D-glucopyranose (48)
Syringoside (49) Avena fatua Triticum aestivum (Liu et al., 2016)
Phenylpropanoids
Dihydrocaffeic acid (50) Cucumis sativus Cucumis sativus (Yu et al., 2003)
3-Phenylpropionic acid (51) Cucumis sativus; Imperata cylindrica Bidens pilosa; Cucumis sativus; Echinochloa (Xuan et al., 2009; Yu et al., 2003)
crus-galli; Leucaena leucocaphala
β-Phenyl-lactic acid (52) Secale cereale Amaranthus retroflexus; Chenopodium (Shilling et al., 1985)
album
Eugenol (53) Eugenia spp. Bidens pilosa; Cassia occidentalis (Vaid, Batish, Singh, & Kohli, 2010)
2,4-Di-tert-butylphenol (54) Imperata cylindrica Bidens pilosa; Imperata cylindrica; (Xuan et al., 2009)
Echinochloa crus-galli; Leucaena
leucocaphala
Isoeugenol (55) Imperata cylindrica Bidens pilosa; Imperata cylindrica; (Xuan et al., 2009)
Echinochloa crus-galli; Leucaena
leucocaphala
Coumarins
Scopoletin (56) Medicago sativa Medicago sativa (Ghimire et al., 2019)
Umbelliferone (57) Stellera chamaejasme Elymus dahuricus; Festuca arundinacea; Poa (Guo et al., 2016; Shettel & Balke, 1983)
annua; Avena sativa
Furanocoumarins
Chalepin (58) Stauranthus perforatus Amaranthus hypochondriacus; Echinochloa (Anaya et al., 2005)
crus-galli
Aromatic amino acids
m-Tyrosine (59) Festuca spp. Abutilon theophrasti; Arabidopsis thaliana; (Bertin et al., 2007)
Cerastium vulgatum; Digitaria sanguinalis;
Echinochloa crus-galli; Lactuca sativa;
Lepidium sativum; Lotus corniculatus;
Medicago lupulina; Plantago major; Poa
annua; Portulaca oleracea; Stellaria media;
Taraxacum officinale; Trifolium repens
HOANG ANH ET AL.
TABLE 1 (Continued)

Phenolic compounds Plant sources Indicator plants References

(C6-C4) Compounds
Naphthoquinones
HOANG ANH ET AL.

Juglone (60) Juglans nigra Cirsium arvense; Cucumis melo; Cucumis (Al-Jawasim, Ghitheeth, & Jabar, 2019;; Li,
sativus; Lamium amplexicaule; Papaver Nishimura, et al., 1993; Terzi, 2008; Topal,
rhoeas; Raphanus raphanistrum; Sinapis Kocaçalişkan, Arslan, & Tel, 2007)
arvensis; Solanum lycopersicum; Pisum
sativum
Phenylbutyric acids
4-Phenylbutyric acid (61) Helianthus annuus; Oryza sativa; Secale Lactuca sativa (Chou & Patrick, 1976; Seal, Pratley, Haig, &
cereale; Zea mays An, 2004)
(C6-C2-C6) Compounds
Anthraquinones
Emodin (62) Polygonum sachalinense; Rhamnus alaternus Amaranthus viridis; Helianthus annuus; (Hasan, 1998; Inoue, Nishimura, Li, &
Lactuca sativa; Phleum pretense; Zea mays Mizutani, 1992)
Physcion (63) Polygonum sachalinense Lactuca sativa (Inoue et al., 1992)
(C6-C3-C6) Compounds
Flavones
Tricin (64) Agropyron repens; Avena fatua; Echinochloa Lepidium sativum; Triticum aestivum (Kong, Zhao, Xu, Wang, & Gu, 2007; Liu
crus-galli; Oryza sativa et al., 2016; Weston, Burke, &
Putnam, 1987)
40 -Methoxyapigenin (65) Cistus ladanifer Rumex crispus (Chaves, Sosa, & Escudero, 2001)
3,7-Dimethoxykaempferol (66)
Isokaempferide (67)
Bonanzin (68) Jasonia montana Convolvulus arvensis (Balah, 2012)
Luteolin (69) Conyza canadensis Agrostis stolonifera; Lactuca sativa (Zhang et al., 2017)
Diosmetin (70) Avena fatua Triticum aestivum (Liu et al., 2016)
Acacetin (71)
3, 6, 7, 30 ,4’-Pentamethoxy flavone Jasonia montana Convolvulus arvensis (Balah, 2012)
(72)
6, 4’-Dihydroxy-3, 7-dimethoxy
flavone (73)
6, 4-Dihydroxy-3, 5, 7-
trimethoxyflavone (74)
(Continues)
45
TABLE 1 (Continued)
46

Phenolic compounds Plant sources Indicator plants References

Apigenin (75) Dittrichia viscosa Lactuca sativa (Levizou, Karageorgou, Petropoulou,
Grammatikopoulos, & Manetas, 2004)
Flavanones
Eriodictyol (76) C. canadensis Agrostis stolonifera; Lactuca sativa (Zhang et al., 2017)
5-Hydroxy-40 ,7-dimethoxyflavanone Piper methysticum Raphanus sativus (Van, Xuan, Minh, & Quan, 2018)
(77)
Matteucinol (78)
Naringenin (79) Centaurea maculosa Arabidopsis thaliana; Centaurea diffusa; (Bais, Walker, Kennan, Stermitz, &
Centaurea maculosa; Kochia scoparia; Vivanco, 2003)
Linaria dalmatica; Lycopersicon
esculentum; Triticum aestivum
Flavonols
Dihydroquercetin (80) Centaurea maculosa; Jasonia montana Arabidopsis thaliana; Centaurea diffusa; (Bais et al., 2003; Balah, 2012)
Centaurea maculosa; Convolvulus arvensis;
Kochia scoparia; Linaria dalmatica;
Lycopersicon esculentum; Triticum
aestivum
Kaempferol (81) Centaurea maculosa Arabidopsis thaliana; Centaurea diffusa; (Bais et al., 2003)
Centaurea maculosa; Kochia scoparia;
Linaria dalmatica; Lycopersicon
esculentum; Triticum aestivum
Quercetin (82) Capparis spinose; Centaurea maculosa; Arabidopsis thaliana; Centaurea diffusa; (Bais et al., 2003; Ghimire et al., 2019;
Medicago sativa; Pluchea lanceolata Centaurea maculosa; Kochia scoparia; Ladhari, Omezzine, Dellagreca, Zarrelli, &
Lactuca sativa; Linaria dalmatica; Haouala, 2013)
Lycopersicon esculentum; Medicago sativa;
Peganum harmala; Raphanus sativus;
Silybum marianum; Triticum aestivum;
Vigna unguiculate
6-Methoxy-kaempferol (83) Dittrichia viscosa Lactuca sativa (Levizou et al., 2004)
Rhamnetin (84)
Isorhamnetin (85)
Taxifolin (86)
Catechins
Catechin (87) Centaurea maculosa; Centaurea stoebe Arabidopsis thaliana; Centaurea diffusa; (Bais et al., 2003; Bais & Kaushik, 2010)
Centaurea maculosa; Festuca idahoensis;
Kochia scoparia; Linaria dalmatica;
HOANG ANH ET AL.

Lycopersicon esculentum; Triticum aestivum

TABLE 1 (Continued)

Phenolic compounds Plant sources Indicator plants References

Epicatechins
Epicatechin (88) Centaurea maculosa; Litchi chinensis Arabidopsis thaliana; Centaurea diffusa; (Bais et al., 2003; Wang et al., 2013)
HOANG ANH ET AL.

Centaurea maculosa; Kochia scoparia;

Flavan-3,4-diols
Flavan-3,4-diol (89)
Pterocarpanes
Medicarpin (90)
Flavonoid glycosides
Rutin (91)
Kaempferol-3-O-galactoside (92)
Quercetin-3-O-β-D-glucopyranoside
(93)
(C6-C3)2 Compounds
Coumaric acids and derivatives
3,5-Dicaffeoylquinic acid (94)
(C6-C3-C6)2 compounds
Biflavonoids and polyflavonoids
Procyanidin A2 (95)
(C6-C1)10 compounds
Tannins
Tannic acid (96)
Others
Phenolic monoterpenes
Thymol (97)
Lactuca sativa; Linaria dalmatica;
Lycopersicon esculentum; Triticum
aestivum
Centaurea maculosa Arabidopsis thaliana; Centaurea diffusa;
Centaurea maculosa; Kochia scoparia;
Linaria dalmatica; Lycopersicon
esculentum; Triticum aestivum
Medicago sativa Medicago sativa; Abutilon theophrasti
Medicago sativa Medicago sativa
Capparis spinosa; Litchi chinensis Lactuca sativa; Peganum harmala;
Raphanus sativus; Silybum marianum
Jasonia montana Convolvulus arvensis
Litchi chinensis Lactuca sativa
Ampelocissus latifolia Triticum aestivum
Hypericum perfoliatum; Santolina Amaranthus retroflexus; Centaurea
chamaecyparissus; Thymus vulgaris; salsotitialis; Chenopodium album; Lepidium
Origanum onites; Thymbra spicata; sativum; Raphanus raphanistrum; Rumex
Origanum acutidens nepalensis; Sinapis arvensis; Sonchus
oleraceus; Lactuca sativa; Portulaca
oleracea; Echinochloa crus-galli; Rumex
(Bais, Park, Weir, Callaway, &
Vivanco, 2004)
(Dornbos, Spencer, & Miller, 1990)
(Ghimire et al., 2019)
(Ladhari et al., 2013; Wang et al., 2013)
(Balah, 2012)
(Wang et al., 2013)
(Chaudhuri & Ray, 2016)
(Angelini et al., 2003; Azirak &
Karaman, 2008; Grosso, Coelho, Urieta,
Palavra, & Barroso, 2010; Kordali
et al., 2008)
47

crispus; Capsicum annuum

(Continues)
 48

TABLE 1 (Continued)

Phenolic compounds Plant sources Indicator plants References

Carvacrol (98) Melissa officinalis; Origanum acutidens; Amaranthus retroflexus; Centaurea (Angelini et al., 2003; Azirak &
Origanum vulgare; Santolina salsotitialis; Chenopodium album; Karaman, 2008; De Almeida, Frei,
chamaecyparissus; Satureja montana; Raphanus raphanistrum; Rumex Mancini, De Martino, & De Feo, 2010; De
Teucrium montbretia; Teucrium polium; nepalensis; Sinapis arvensis; Sonchus Martino, Roscigno, Mancini, De Falco, &
Origanum onites; Thymbra spicata oleraceus; Lactuca sativa; Portulaca De Feo, 2010; Grosso et al., 2010; Kordali
oleracea; Echinochloa crus-galli; Capsicum et al., 2008)
annuum
Phenolic lipids
Helibisabonol A (99) Helianthus annuus Triticum aestivum (Macías et al., 2002)
Phenolic sesquiterpenes
Heliannuol A (100) Helianthus annuus Triticum aestivum (Macías et al., 2002)
Dibenzofurans
Usnic acid (101) Alectoria sarmentosa Helianthus annuus; Zea mays (Lascève & Gaugain, 1990; Romagni,
Meazza, Nanayakkara, & Dayan, 2000)
Quinolines
8-Hydroxyquinoline (102) Centaurea diffusa; Centaurea maculata Centaurea maculosa; Acroptilon repens (Vivanco, Bais, Stermitz, Thelen, &
Callaway, 2004)
Benzoxazinones
2,4-Dihydroxy-1,4-benzoxazin-3-one Secale cereale Amaranthus retroflexus; Chlamydomonas (Barnes & Putnam, 1987; Chase, Nair, &
(103) rheinhardtii; Cucumis sativus; Echinochloa Putnam, 1991)
crus-galli; Lactuca sativa; Lepidium
sativum; Lycopersicon esculentum;
Phaseolus vulgaris
2,4-Dihydroxy-7-methoxy- Secale cereale; Triticum aestivum Amaranthus retroflexus; Apera spica-venti; (Copaja, Villarroel, Bravo, Pizarro, &
1,4-benzoxazin-3-one (104) Echinochloa crus-galli; Lactuca sativa; Argandoña, 2006; Mathiassen, Kudsk, &
Setaria viridis Mogensen, 2006)
HOANG ANH ET AL.
HOANG ANH ET AL. 49

Phenolic compounds
(C6) Compounds
Simple phenols

(1) (2) (3) (4)

(C6-C1) Compounds
Shikimic acids and derivatives

(5)
Benzoic acids and derivatives

(6) (7) (8) (9)

(10) (11) (12) (13)

(14) (15) (16) (17)

(18) (19) (20)

FIGURE 2 Structures of phenolic allelochemicals mentioned in Table 1

even pollen (Weston & Duke, 2003). There are multiple
factors that determine the production and release of these
allelochemicals from plants to the environment. The natu-
ral characteristics of these compounds (the molecular
weight and polarity) and their content in plants are impor-
tant factors. For example, compounds with close character-
istics tend to be released together in a mixture to the
rhizosphere (Macías, Molinillo, Varela, & Galindo, 2007).
Additionally, the growth stage, biomass, and density of
recipient plants are other factors affecting the exudation of
phenolic allelochemicals by donor plants into the soil.
For instance, an increase in exudation will be
required for a higher density of recipient plants. The
release of phenolic compounds can be regulated by
the effects of biotic and abiotic stresses, including
drought, temperature, nutrient deficiency, plant competi-
tors, pests, and diseases (Cseke & Kaufman, 1999;
Einhellig, 1996; Vidal & Bauman, 1997). The changes in
electrical conductivity and osmotic pressure also correlate
strongly to the release of allelochemicals into the soil due
to the decomposition of allelopathic plants (Xuan,
Tawata, Khanh, & Chung, 2005).
50 HOANG ANH ET AL.

Phenolic aldehydes

(21) (22) (23) (24)

(25) (26) (27)

Phenolic glycosides

(28)
(C6-C2) Compounds
Phenylacetic acids

(29) (30) (31)

Acetophenones

(32) (33)
Styrenes

(34) (35)
Phenethylamines

(36)

FIGURE 2 (Continued)

4.4 | Degradation
To date, most studies on the allelopathic activity of iso-
lated phenolic allelochemicals have been conducted with-
out the effects of soil conditions. As a result, the
phytotoxic activities of compounds in artificial situations
do not precisely reflect the practical conditions. After
releasing into the environment, allelochemicals can be
degraded by multiple factors, especially soil
microorganisms, such as bacteria and fungi that can con-
sume the organic chemicals.
The phytotoxic effects on donor plants might not be as
expected (Tharayil, Bhowmik, & Xing, 2008; Yoneyama &
Natsume, 2013). A previous study indicated that phenolic
allelochemicals could be degraded in the soil after 10 days;
however, a strong inhibition against the weeds
Echinochloa crus-galli and Monochoria vaginalis was still
recorded after 25 days (Xuan et al., 2005). Therefore, a
HOANG ANH ET AL. 51

(C6-C3) Compounds
Cinnamic acids and derivatives

(37) (38) (39) (40)

(41) (42) (43) (44)

(45) (46)
Phenolic glycosides

(47) (48)

(49)
Phenylpropanoids

(50) (51) (52) (53)

(54) (55)
Coumarins

(56) (57)

FIGURE 2 (Continued)

deep understanding of phenolic degradation is essential multiple plant biological activities (Macías
for the development of phenolic herbicides. et al., 2007). In general, phenolic allelochemicals can
affect weed cell functions via various biological path-
ways (Haig, 2008).
5 | P H E N O L IC
ALLELOCHEMICALS: MODES OF
ACTION 5.1 | Oxidative stress

Phenolic allelochemicals can directly affect plant sys- In previous studies, oxidative stress was induced in
tems via plant uptake. They also regulate the activi- phenolic-treated plants. The enhancement of oxidative
ties of plant symbiotic microorganisms (Jassey stress in cucumber under the effects of cinnamic acid is
et al., 2011). One compound may be involved in an example (Ye, Zhou, Sun, Zou, & Yu, 2006). The
52 HOANG ANH ET AL.

Furanocoumarins

(58)
Aromatic amino acids

(59)
Naphthoquinones

(60)
Phenylbutyric acids

(61)
(C6-C2-C6) Compounds
Anthraquinones

(62) (63)
(C6-C3-C6) Compounds
Flavones

(64) (65)

(66) (67)

FIGURE 2 (Continued)

mechanism can be explained: antioxidant enzymes are
suppressed by phenolics, and thus the formation of reac-
tive oxygen species is increased, resulting in oxidative
damage (Chai, Ooh, Ooi, Chue, & Wong, 2013; Ye
et al., 2006; Yu et al., 2003). Consequently, the plant
metabolism is negatively affected.
5.2 | Cell division and permeability
Together with cell growth, cell division is the most
important process determining the growth of plants,
including root elongation, the number of Golgi bodies,
and the differentiation of meristems. Substances causing
an inhibition of cell division may subsequently prevent
the growth of plants and are, therefore, so-called plant
growth inhibitors. The lettuce (Lactuca sativa) cell divi-
sion was inhibited by coumarins, resulting in the sup-
pression of root elongation (Li, Inoue, et al., 1993).
Consequently, the coumarins impeded the growth of
lettuce.
Phenolic allelochemicals, such as benzoic, cinnamic,
and ferulic acids, can affect the cell permeability (Chai
et al., 2013; Kobza & Einhellig, 1987; Politycka, 1997).
HOANG ANH ET AL. 53

(68) (69)

(70) (71)

(72) (73)

(74) (75)
Flavanones

(76) (77)

(78) (79)
Flavonols

(80) (81)

(82) (83)

FIGURE 2 (Continued)

After that, the lipid peroxidation will be increased, and 5.3 | Photosynthesis, respiration, and
plant tissue will be harmed (Chai et al., 2013). In addi- transpiration
tion, cell permeability is a determinant of the plant nutri-
ent uptake. Therefore, inhibition of this physiological Photosynthesis is an indispensable process in plants. The
activity can lead to an imbalance of nutrients in process has been proven to be inhibited by phenolic
plants, resulting in growth suppression (Kobza & allelochemicals. In particular, grandinol and
Einhellig, 1987). homograndinol, caffeic, coumaric, ferulic, cinnamic,
54 HOANG ANH ET AL.

(84) (85)

(86)
Catechins

(87)
Epicatechins

(88)
Flavan-3,4-diols

(89)
Pterocarpanes

(90)
Flavonoid glycosides

(91) (92)

FIGURE 2 (Continued)

and vanillic acids can be listed as photosynthetic inhibi-
tors (Patterson, 1981; Yoshida et al., 1988). The effective
doses and physiological responses are divergent among
various weed species.
Respiration is directly related to the energy metabo-
lism in plants. A previous report indicated that the respi-
ratory process can be suppressed by applying phenolic
compounds, including benzoic and cinnamic acids,
resulting in plant growth inhibition (Yu et al., 2003).
Transpiration is another crucial process that balances
the leaf temperature and is involved in plant nutrient
uptake. Yoneyama et al. (1996) indicated that the transpi-
ration of mung bean (Vigna radiata) was prevented
under the effects of grandinol due to a decrease in the
stomatal pore opening. The acylphloroglucinol structure
might play a significant role in inhibiting plant transpira-
tion. The suppression of transpiration may lead to the
loss of functions or even the death of plant leaves.
HOANG ANH ET AL. 55

(93)
(C6-C3)2 compounds
Coumaric acids and derivatives

(94)
(C6-C3-C6)2 compounds
Biflavonoids and polyflavonoids

(95)
(C6-C1)10 compounds
Tannins

(96)

FIGURE 2 (Continued)

5.4 | Gene expression, protein
biosynthesis, phytohormone activities, and
enzyme functions
Phenolic allelochemicals can inhibit nucleic acid formation,
which is an essential process in the cellular metabolism and
gene expression. Through this inhibitory pathway, the sup-
pression of protein biosynthesis was recorded. For example,
the inhibitory effects of cinnamic and ferulic acids on
protein biosynthesis can be explained via this genetic mech-
anism (He & Lin, 2001; Ni, 2000; Zeng, Luo, & Shi, 2001).
Phenolics, including hydroxyl benzoic acid and poly-
phenols, can inhibit phytohormones, such as indole-
3-acetic acid, gibberellin, and ethylene (He & Lin, 2001;
Leslie & Romani, 1988), which are important regulators
of various plant developmental processes.
Phenolic compounds also have various inhibitory
effects against enzyme activities. For instance, chlorogenic,
56 HOANG ANH ET AL.

Others
Phenolic monoterpenes

(97) (98)
Phenolic lipids

(99)
Phenolic sesquiterpenes

(100)
Dibenzofurans

(101)
Quinolines

(102)
Benzoxazinones

(103) (104)

FIGURE 2 (Continued)

caffeic acids, and catechol are inhibitors of phosphorylase.
Cinnamic acid and its derivatives are inhibitors of ATPase.
Tannic acid is an inhibitor of peroxidase, catalase, and cel-
lulase (Rice, 1974). In addition, caffeic acid exhibits inhibi-
tion against protease (Batish et al., 2008).
Certain phenolic allelochemicals also inhibit phenyl-
alanine ammonia-lyase (PAL), hydrolase, maltase, phos-
pholipase, and protease (Devi & Prasad, 1992;
Politycka, 1998). Abenavoli, Lupini, Oliva, and
Sorgona (2010) reported that cinnamic, ferulic, and
ρ-coumaric acids had inhibitory effects against the
enzyme H+-ATPase, which can be the cause of decreas-
ing nitrate uptake in Zea mays roots.
pathogenic microorganisms via biological and physical
pathways (Bais et al., 2004). Located microorganisms in
the rhizosphere play an important role in plant adapta-
tions to environmental conditions. Additionally, these
organisms can regulate the soil characteristics related to
plant development (Mathesius & Watt, 2010; Nardi
et al., 2000). Thus, the effects on symbiotic and patho-
genic microorganisms may indirectly regulate the growth
of weeds.
6 | E X T R A C T I O N , IS O L A T I O N ,
A N D PU R I F I C A T I O N O F PH E N O L I C
ALLELOCHEMICALS

5.5 | Symbiotic and pathogenic
microorganisms
In addition to the direct effects on plant growth, phenolic
allelochemicals also interact with symbiotic and
There are various methods to extract, isolate, and purify
phenolic compounds from plants and different protocols
exhibit diverse effectiveness and limitations. There is no
standard protocol for the isolation of phenolic com-
pounds from different allelopathic plant sources.
HOANG ANH ET AL. 57

F I G U R E 3 Biosynthetic pathways of phenolic allelochemicals (aggregated based on pathways described by Jiang et al., 2013; Lee
et al., 2018). DHD, 3-dehydroquinate dehydratase; SDH, shikimate dehydrogenase; 3DSD, 3-dehydroshikimate dehydratase; PCAH,
protocatechuic acid hydroxylase; ADT, arogenate dehydratase; PH, phenylalanine hydroxylase; PAL, phenylalanine ammonia lyase; CNL,
cinnamoyl-CoA ligase; C4H, cinnamic acid 4-hydroxylase; C3H, ⍴-coumaroyl ester 3-hydroxylase; C30 H, ⍴-coumaroyl ester 30 -hydroxylase;
COMT, caffeic acid/5-hydroxyferulic acid O-methyltransferase; 4CL, 4-coumaroyl:CoA-ligase; CHS, chalcone synthase; CHR, chalcone
reductase; CHI, chalcone isomerase; F3H, flavanone 3-hydroxylase; F30 H, flavanone 30 -hydroxylase; FLS, flavonol synthase; UFGT, UDP
glucose: flavonoid-3-O-glucosyltransferase; FLS, flavonol synthase; DFR, dihydroflavonol 4-reductase; LAR, leucoanthocyanidin reductase;
ANS, anthocyanidin synthase; ANR, anthocyanidin reductase; IFS, isoflavone synthase; IFR, isoflavone reductase

However, based on sample natural characteristics, target 6.2 | Extraction of phenolic

compounds, and objectives, the processes can be opti-
mized with the highest efficiency of extraction and isola-
tion (Palanisamy, Gunasekaran, Dominic, & Xuan, 2020).
The basic procedure is presented in Figure 4 and
described in this section.
6.1 | Sample preparation
Sample preparation is an important step, and this has
been improved in numerous studies. This step plays a sig-
nificant role in phenolic extraction. Appropriate prepara-
tion can increase the sample stability and extraction
efficiency. In addition, contaminants can be eliminated
or reduced via careful preparation, enhancing the effi-
ciency of chemical analysis and further isolation steps
(Palanisamy et al., 2020).
Sample preparation can be optimized based on the
sample sources, target compounds, and objectives. For
example, phenolic contents are different between plant
species and plant parts (roots, leaves, barks, flowers,
fruits, etc.). Based on the target compounds, such as
phenolic aglycones, the hydrolysis process can be
applied (Willis, 1985). For preservation, the samples
should be kept in dried form or frozen to protect the
chemical composition (Palanisamy et al., 2020).
allelochemicals
In general, the classical solid–liquid solvent extraction is
widely conducted because it is simple, safe, and low cost
(Garcia-Salas, Morales-Soto, Segura-Carretero, &
Fern
andez-Gutiérrez, 2010). The classical methods are
maceration, percolation, and Soxhlet extractions
(Aires, 2017). Maceration and percolation were popularly
used in the past; however, they show the disadvantages
of being time-consuming and using a large volume of sol-
vent. Additionally, their efficiency is lower compared
with other methods. Among classical extractions, Soxhlet
is considered as the most effective method (Azmir
et al., 2013; Seidel, 2012; Sticher, 2008).
In the classical methods, the solvent polarity is also
important as this determines the capacity in phenolic
extraction. A wide range of solvents can be used, such
as water, methanol, ethanol, hexane, ethyl acetate, and
others (Aires, 2017). Among them, aqueous organic
solvents have been recently proven to display higher
efficiencies over individual organic solvents. In partic-
ular, plant extracts acquired by aqueous methanol
demonstrated the highest content of phenolics com-
pared to those extracted by other solvents (Iloki-
Assanga et al., 2015; Metrouh-Amir, Duarte, &
Maiza, 2015).
58
However, the limitations of classical methods include
the low efficiency, time-consumption, and pollution with a
high volume of applied organic solvents. Due to these rea-
sons, more advanced methods have been developed, which
include microwave-assisted extraction, ultrasound-assisted
extraction, supercritical CO2 extraction, pressurized fluid
extraction, and enzyme-assisted extraction. Based on the
literature, there are effective choices to overcome the dis-
advantages of classical methods (Aires, 2017).
6.3 | Isolation of phenolic
allelochemicals
The obtained extracts from plants containing phenolic
compounds can be used for further fractionation and
isolation. The most popular method for fractionation is
column chromatography. Through this method, com-
pounds can be separated based on their adsorption
(Palanisamy et al., 2020). The affinity of phenolic com-
pounds is determined by the formation of hydrogen
linking between proton donors and recipient groups in
the resin and the hydrophobic interaction with the
aromatic rings.
Following this feature, a method can be developed to
acquire phenolic compounds with numerous hydroxyl
groups and aromatic rings (Einhellig, 2003). To support
the isolation process, widely applied methods for the
analysis of phenolic compounds in samples from plants
include thin-layer chromatography, gas
chromatography–mass spectrometry, liquid chromatogra-
phy electrospray ionization mass spectrometry, nuclear
magnetic resonance, and others (Figure 4) (Palanisamy
et al., 2020). In addition to column chromatography,
counter-current chromatography is another effective
method for phenolic isolation, which has been recently
expanded using (Palanisamy et al., 2020).
7 | P H E N O L IC
ALLELOCHEMICALS: CURRENT
STATUS AND FUTURE
PERSPECTIVES
7.1 | Current status
Allelopathy is included in the research on complex
plant–plant and plant–microorganism interactions,
which is a very active field in plant sciences. Recently,
studies on allelopathy have been continuously increased
globally with a vast number of identified allelochemicals.
Of these, phenolics are in the largest class, and can be
used to inhibit dangerous weed species. A vast amount of
HOANG ANH ET AL.
research has been widely conducted in the field of pheno-
lic allelochemicals.
Numerous advanced analytical methods have been
developed to effectively evaluate the potential properties
of these allelochemicals, including their distribution,
release, degradation, biosynthesis, structure, and absorp-
tion in practices under various environmental factors.
Many specific methods have been improved to effectively
exploit phenolic allelochemicals based on the sample fea-
tures and research objectives. However, no phenolic
allelochemicals have been successfully developed as a
natural herbicide. Therefore, in this section, we discuss
the current status of research on phenolic allelochemicals
in sustainable weed management and the existing limita-
tions are also presented.
7.1.1 | Application doses of phenolic
allelochemicals
The research on application doses is required to develop
phenolic herbicides, as the allelopathic response of these
compounds depends on the doses. Investigating the rela-
tionship between application doses and their response
effects can help to determine the modes of action of phe-
nolic allelochemicals (Belz, Velini, & Duke, 2007). Far-
ooq, Abbas, Tanveer, and Jabran (2020) mentioned that
allelochemicals might show stimulation at a low con-
centration, which can contribute positively to crop
plants via strengthening plant growth and competition
over weeds. Otherwise, inhibition can be observed when
increasing the concentration for use directly as natural
herbicides.
7.1.2 | Factors induce the biosynthesis of
phenolic allelochemicals in plants
The factors involved in the biosynthesis of
allelochemicals include different species, growth periods,
and plant tissues. Otherwise, exogenous factors, such as
natural enemies, drought, temperature, soil conditions,
rainfall, nutrients, irrigation, and ultraviolet
(UV) radiation, can be regarded as important determi-
nants (Cseke & Kaufman, 1999; Einhellig, 1996;
Iannucci, Fragasso, Platani, & Papa, 2013; Mahmood
et al., 2013). For instance, the production of
momilactone B, a well-known plant inhibitor from rice,
was proven to be closely correlated to various biotic and
abiotic stresses, such as weed, UV, drought, and salt
stresses, heavy metal ions, and blast fungus (Kato-
Noguchi & Peters, 2013; Xuan, Minh, Anh, &
Khanh, 2016).
HOANG ANH ET AL.
F I G U R E 4 Process of
extraction, isolation, and
purification of phenolic
allelochemicals (improved based
on the report of Palanisamy
et al., 2020)
The mechanisms for increasing the content of phyto-
chemicals can be explained through the expression and
regulation of relevant genes encoding the key enzymes
involved in the biosynthetic pathways. Numerous studies
were carried out to support this point. For example, the
expression increases of genes encoding PAL, Oryza sativa
momilactone A synthase, and Oryza sativa momilactone
A synthase 2 in rice grown with barnyardgrass were
announced. These enzymes are related to the formation
of phenolics and momilactones in rice (Bajsa-Hirschel,
Pan, & Duke, 2020; He et al., 2012).
In another report of Song et al. (2008), the allelo-
pathic activity of rice variety PI312777 was strengthened
under a nitrogen deficit. Additionally, the overexpression
of genes encoding PAL, O-methyltransferase, tri-
osephosphate isomerase, and P450 was remarkably
recorded. These enzymes play a major role in the pheno-
lic synthetic pathway. Therefore, the biosynthesis of phe-
nolic allelochemicals and the expression of relevant
genes are strongly correlated with weed stress in particu-
lar and other stresses in general. To reinforce this state-
ment, research on Arabidopsis thalina obtained that the
plant response to weed stress through the phenolic bio-
synthetic pathway was similar to other biotic and abiotic
stresses (Golisz, Sugano, & Fujii, 2008).
Further evidence indicated that the accumulations of
phenylpropanoid and flavonoid allelochemicals in various
plant species, such as beans, parsley, potatoes, tomatoes,
maize, rye, barley, and rice, were increased under the effect
of UV-B irradiation (Hahlbrock & Scheel, 1989; Kim
et al., 2000; Liu, Gitz, & McClure, 1995). Thus, it can be con-
cluded that phenolic contents can be regulated by adjusting
the endogenous factors by genetic modification or altering
exogenous factors to induce the expression of relevant genes.
Numerous major enzymes are involved in the biosyn-
thesis of potential phenolic allelochemicals (Figure 3),
and their relevant genes have been globally
59
acknowledged (NCBI, 2021). Many other vital enzymes
remain uncharacterized. Therefore, subsequent studies
should be conducted to clarify this information, which
can contribute to further research on genetic engineering
approaches involving the plant response to weed stress
via the biosynthesis of phenolic allelochemicals.
7.1.3 | Genetic engineering approaches
Biotic stresses caused by weeds, fungus, virus, and bacteria
threaten agriculture worldwide. Among these, weed inva-
sion is considered to cause a higher yield loss over the
other biotic stresses. To date, there are some conducted
studies that identified and transferred the quantitative trait
locus/genes (QTLs/genes) related to the tolerance/resis-
tance of plants against biotic stresses with multiple aspect
sites. However, very few crops were identified with QTLs/
genes determining phenolic allelochemicals in the
response of target plants to weed stress.
Regarding improving crop productivity, increasing
the content of phenolic compounds in plants with high
allelopathic activity using this approach has a high poten-
tial (Soltys, Krasuska, Bogatek, & Gniazdowsk, 2013). It
is possible to identify the QTLs/genes related to these
compounds in plants (Belz, 2007). The first investigation
of QTLs involved in allelopathic activity was conducted
in rice. These QTLs were identified as associated with the
enzymatic activities of PAL, thioredoxin, and 3-hydroxy-
3-methylglutaryl coenzyme A reductase, which play sig-
nificant roles in the biosynthesis of phenolic compounds
(Lin, He, et al., 2004).
Other crops were genetically analyzed, including
wheat, barley, and oats; however, the results are still lim-
ited (Belz, 2007). To date, successful transgenic studies
covered the enhancement of phenolic production in hairy
roots of nettleleaf goosefoot (Miti
c et al., 2012) and
60
gossypol of cotton (Triplett, Moss, Bland, & Dowd, 2008).
The outcomes are considered as having high stability in
the genetic background.
7.1.4 | Allelopathic activity of phenolic
mixtures
At the present time, the effects of individual phenolic
compounds on weed growth have been extensively publi-
shed. However, the allelopathic interactions among these
compounds have been rarely investigated. Phenolic
allelochemicals always appear in mixtures instead of as
individual compounds in nature. Studies determined that
the mixtures had higher allelopathic activity compared
with individual compounds (Einhellig, 1996; Quan,
Xuan, Tran, & Thuy, 2019).
For example, momilactone E and 7-ketostigmasterol
individually showed no effects against test plants; how-
ever, their mixture significantly inhibited the growth of
Solidago altissima (Quan et al., 2019). In the report
of Chai et al. (2013), the interaction between phenolics
and mimosine in Leucaena leucocephala leachate may
compromise the membrane integrity, respiration, and
antioxidative defense of water hyacinth leaf tissues. In
natural allelopathy, the activity significantly depended on
a complex mixture of compounds.
The mechanism could be explained in that the
mixture of different groups revealed various sites of
action. In addition, the synergic interactions between
compounds at the molecular level can determine the
allelopathic activity of the mixture (Albuquerque
et al., 2011; Einhellig, 1996; Neilson et al., 2013).
Therefore, this should be an integral part of the forth-
coming research on developing natural herbicides with
high efficiency.
7.1.5 | Development of phenolic herbicides
In laboratory and in greenhouse, numerous phenolic
allelochemicals have been acknowledged with various
modes of action. They can be found abundantly in plant
tissues, leaf leachates, and roots exudates, and plant resi-
dues. However, the interactions between these com-
pounds and environmental factors in the practical
ecosystem have not been fully elucidated.
The contents of phenolic allelochemicals in soils may
not be high enough to inhibit competitive weeds due to
their loss in degradation, oxidation, binding to other sub-
stances, and adsorption to soil particles (Tharayil
et al., 2008; Yoneyama & Natsume, 2013). Therefore, the
development of herbicides from these sources has met
HOANG ANH ET AL.
limitations. Very few phenolic allelochemicals have been
developed successfully in field conditions.
The production of natural-based herbicides has been
attractive for industries. Among popularly known syn-
thetic herbicides, phosphinothricin, glyphosate,
sulcotrione, mesotrione, and cinmethylin are produced
with base from natural products as lead compounds. The
commercial herbicides from natural products are very
few, which can be mentioned as bialaphos and
pelargonic acid. However, none of these consist of pheno-
lic compounds, despite phenolics being a plentiful source
for developing new herbicides. The reasons are that these
compounds require high production costs and have low
stability and selectivity (Farooq et al., 2020).
7.2 | Future perspectives
A vast number of studies on phenolic allelochemicals
have been conducted. However, very few of these
allelochemicals have been successfully applied by
farmers. To solve this problem, the practical application
of phenolic allelochemicals should be evaluated. Enhanc-
ing the interdisciplinary knowledge of soil, chemistry,
ecology, genetic, molecular biology, and others can help
to interpret the activities of phenolic allelochemicals in
natural conditions.
In addition, the regulation and biosynthetic mecha-
nisms of these compounds in donor plants involving in
response to weed stress should be discovered. Compre-
hensive information regarding these complex interactions
will lead to further research on weed management,
including the production of bioherbicides with multiple
target sites and the improvement of resistant plants
against weed stress via genetic approaches. Some promis-
ing directions in the future research on phenolic
allelochemicals are discussed in this section.
7.2.1 | Allelopathic activity of mixtures
Among the promising approaches, the research on allelo-
pathic effects of compound mixtures can contribute to
the development of synthetic herbicides with multiple
modes of action in the future. A vast number of mixtures,
including phenolics and other prospective compounds,
should be examined for their allelopathic effects and
modes of action, since their potential has been indicated
(Einhellig, 1996; Li et al., 2010; Quan et al., 2019).
Apart from phenolics, other allelochemicals possessing
potent inhibition on weeds should be considered, such as
momilactones from rice (Oryza sativa) and the moss
(Hypnum plumaeform) (Kato-Noguchi, Hasegawa, Ino,
HOANG ANH ET AL.
Ota, & Kujime, 2010; Quan et al., 2019), mimosine from
Leucaena leucocephala (Xuan, Elzaawely, Deba, Fukuta, &
Tawata, 2006; Xuan, Minh, & Khanh, 2016), and
sorgoleone from Sorghum spp. (Czarnota, Paul, Dayan,
Nimbal, & Weston, 2001; Einhellig & Souza, 1992). These
mentioned compounds exhibit a potent suppressive effect
on various weed species.
Therefore, the synergic activity of these compounds
and phenolic allelochemicals is a promising approach to
develop natural herbicides with high effectiveness in
weed management and crop protection. However, the
contributions and interactions among compounds in
the mixture should be investigated because the allelo-
pathic activity of mixtures can be regulated by multiple
factors, including plant growth periods, density, plant
uptakes, environmental conditions, and others.
Thus, allelopathic bioassays of mixtures should be con-
ducted simulating the practical conditions with various
impact factors instead of a single one (Albuquerque
et al., 2011; Einhellig, 1996; Neilson et al., 2013). The
determination of the dose/response relationship can be
sufficient proof indicating the interactions between differ-
ent phenolic allelochemicals, including both antagonistic
and synergistic effects and can reflect their activity prop-
erly in particular natural conditions (Belz et al., 2007).
7.2.2 | Structural modifications of phenolic
allelochemicals
As mentioned in the current status of developing phenolic
herbicides by industries, the high production cost, low sta-
bility, and selectivity of these allelochemicals are challenges.
To solve these problems, Farooq et al. (2020) mentioned the
potential approach of artificial modification in the structure
of phenolic compounds, which could strengthen the stabil-
ity and activity of targeted compounds with multiple modes
of action. This solution can expand the directions in the
research on allelochemicals in the future.
7.2.3 | Genetic engineering approaches
Another advanced technology is genetic engineering.
Induced-gene expression, metabolic engineering, and
genetic modification are potential approaches in enhanc-
ing phenolic allelochemicals to cope with weed stress
(Bourgaud, Gravot, Milesi, & Gontier, 2001). A compre-
hensive understanding of the biosynthetic output of these
allelochemicals via the gene expression pathways is a
promising strategy aiming to exploit a higher amount of
these compounds from plant sources.
A comprehensive database of genes encoding key
enzymes in the phenolic biosynthetic pathways is
61
published online by NCBI GenBank. For example, by
searching the mentioned names of enzymes in Figure 3,
complete information can be accessed, comprising plant
species, genomic regions, transcripts, products, and others.
NCBI GenBank also provides useful tools for analyzing
sequences and designing primers, which can support the
research on genetic engineering (NCBI, 2021).
In contrast, there are many unknown enzymes and
associated relevant genes related to the biosynthesis of
phenolics as well as other potential allelochemicals, which
should be further characterized; however, it is complicated
to precisely define the relevant gene clusters and their
exact role in encoding the targeted enzymes. This research
can provide a deeper understanding of phenolic biosynthe-
sis in plant defense systems responding to weed stress that
also allows investigation of effective solutions for weed
management and targeted crop protection.
Recently, open sources of such data have increasingly
diversified. The insightful integration of these available
resources and information technologies, such as artificial
intelligence (AI) and learning machines, is expected to
create breakthroughs in the discovery of new natural-
based herbicides that are both highly efficient and envi-
ronmentally friendly.
Expanding the research on QTLs/genes related to the
proliferation of phenolic allelochemicals promises valu-
able achievements in the development of sustainable
weed management. Genetic modification protocols can
be listed as marker-assisted selection and marker-assisted
backcrossing, which allow improving resistant plants
against weeds via plant breeding programs. However, a
challenge is that there are multiple QTLs/genes related to
the synthesis of plant compounds.
Therefore, genetic techniques aiming at phenolic
allelochemicals will meet with complications. Even if the
candidate QTLs/genes can be successfully located into the
genetic background of targeted plants, we cannot ensure
that these QTLs/genes will adapt to the environment as
the environment significantly affects gene expression.
The practical results will be unpredictable. In addition,
the negative influence on plant growth or tissues in terms of
improving the endogenous accumulation of phenolic com-
pounds has been still unknown. Thus, to succeed with this
approach, the secondary metabolisms with the activities of
relevant enzymes and QTLs/genes involved in the biosynthe-
sis of phenolic allelochemicals should be deeply understood.
8 | CONCLUSION
To date, studies on phenolic allelochemicals and their
modes of action against a wide range of test plants are
extensive. A great number of allelopathic plants have been
reported as rich in phenolic allelochemicals. Advanced
62
technologies of analytical measurement have been devel-
oped actively and rapidly. Based on these reasons, pheno-
lic allelochemicals can be feasibly exploited from nature or
synthesized from their analogues.
However, research has not been successfully devel-
oped in a wide range of applications under various envi-
ronmental conditions, such as temperature, nutrient,
irrigation, soil characteristics, microorganisms, and
others. Therefore, the uses of phenolic allelochemicals in
weed management should be practically expanded in dif-
ferent ecosystems over yearly replications.
In addition, the allelopathic effects of phenolics and
other potential compounds in mixtures should be com-
prehensively investigated. The information in this review
can be used to establish a useful database for designing
and producing natural herbicides with the most potential
through AI, which can contribute to weed management
and the development of sustainable agriculture.
The biosynthesis of phenolic allelochemicals can be
regulated by modifying the genetic factors. Numerous
crops have been developed by genetic engineering
methods to cope with biotic and abiotic stresses, such as
submergence, drought, pests, diseases, and others. How-
ever, very few breeding programs have been conducted to
generate strong allelopathic plants containing high levels
of phenolic allelochemicals. Thus, this should be consid-
ered as a promising approach in the future.
A C K N O WL E D G M E N T S
The authors are grateful to the Ministry of Education,
Culture, Sports, Science, and Technology (MEXT), Japan
to provide La Hoang Anh a scholarship.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
A U T H O R C ON T R I B U T I O NS
All authors contributed to completing the manuscript.
ORCID
La Hoang Anh https://orcid.org/0000-0002-6844-8296
Nguyen Van Quan https://orcid.org/0000-0002-6567-
9902
Tran Dang Xuan https://orcid.org/0000-0001-7103-
5698
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How to cite this article: Hoang Anh, L., Van
Quan, N., Tuan Nghia, L., & Dang Xuan, T. (2021).
Phenolic allelochemicals: Achievements,
limitations, and prospective approaches in weed
management. Weed Biology and Management, 21
(2), 37–67. https://doi.org/10.1111/wbm.12230