Bioactive Compounds in Agricultural Soils

314 Pages·2016·10.42 MB·English

by  Lech Wojciech Szajdak (eds.)

Lech Wojciech Szajdak Editor
Bioactive
Compounds
in Agricultural
Soils
Bioactive Compounds in Agricultural Soils
Lech Wojciech Szajdak
Editor
Bioactive Compounds
in Agricultural Soils
Editor
Lech Wojciech Szajdak
Institute for Agricultural and Forest Environment
Polish Academy of Sciences
Poznan , Poland
ISBN 978-3-319-43106-2 ISBN 978-3-319-43107-9 (eBook)
DOI 10.1007/978-3-319-43107-9
Library of Congress Control Number: 2016953334
© Springer International Publishing Switzerland 2016
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Contents
1 Introduction: Biologically Active Compounds ..................................... 1
Lech Wojciech Szajdak
Part I Biologically Active Substances in Cropping Systems
2 Free, Bounded, and Included in Humic Acids Amino Acids:
Thermal Properties of Humic Acids from Cropping Systems ............ 25
Lech Wojciech Szajdak , Irena Ż yczyńska-Bałoniak ,
and Kazimiera Wegner
3 Conversions and Pathways of Organic Carbon and Organic
Nitrogen in Soils ...................................................................................... 53
Stanisław Kalembasa and Dorota Kalembasa
4 Free Sulfuric Amino Acids and Rhodanese in Soils Under
Rye Cropping and Crop Rotation ......................................................... 9 1
Lech Wojciech Szajdak and Teodor Rusu
5 Amino Acids, Indole-3-Acetic Acid, Stable and Transient
Radicals, and Properties of Humic and Fulvic Acids as
Affected by Tillage System ..................................................................... 113
Lech Wojciech Szajdak , Miguel L. Cabrera , and Adam Jezierski
6 Rate of Leaching of Organic and Inorganic Compounds
in Tilled and Orchard Soils .................................................................... 131
Lech Wojciech Szajdak , Jerzy Lipiec , Anna Siczek ,
Urszula Kotowska , and Artur Nosalewicz
7 Impact of Long-Term Agricultural Management and Native
Forest Ecosystem on the Chemical and Biochemical Properties
of Retisols’ Organic Matter .................................................................... 149
Alar Astover , Lech Wojciech Szajdak , and Raimo Kõlli
v
vi Contents
Part II The Physiological Importance of Biologically
Active Substances
8 Auxin, One Major Plant Hormone, in Soil ........................................... 175
Junichi Ueda , Marian Saniewski , and Kensuke Miyamoto
9 Transformations of Organic Matter in Soils Under Shelterbelts
of Different Ages in Agricultural Landscape ........................................ 211
Lech Wojciech Szajdak , Victoria Maryganova ,
Eugene Skakovskii , and Ludmila Tychinskaya
10 Phytohormone in Peats, Sapropels, and Peat Substrates .................... 247
Lech Wojciech Szajdak
11 Cranberry: A Plant Growing on Organic Soils with
a Broad Spectrum of Pharmaceutical and Medical Use ...................... 273
Lech Wojciech Szajdak and Lydia I. Inisheva
12 The Importance of Horticultural Growing Media
and Biochemical Processes ..................................................................... 287
Lech Wojciech Szajdak , Katarzyna Styła , Wioletta Gaca ,
Teresa Meysner , Marek Szczepański , and Jacek Stanisław Nowak
Chapter 1
Introduction: Biologically Active Compounds
Lech Wojciech Szajdak
Abstract E ach chemical compound possesses numerous biological activities.
Biological activity spectrum of a compound should be predicted on the basis of the
structure-activity-relationships. The biological activity spectrum of a compound
shows its all actions and its participation in the biological, physiological and meta-
bolically pathways despite the difference in the experimental conditions. The bio-
logical activity spectrum of a compound shows compound’s all actions and the
participation in the biological, physiological and metabolically pathways despite the
difference in the experimental conditions. If the differences in species, sex, age,
dose, and the participation in the metabolic processes and pathways etc. are neglected,
the biological activity may be identifi ed only qualitatively. Thus the biological activ-
ity spectrum is defi ned as the “intrinsic” property of a substance depending only on
its structure and physicochemical characteristics. Structure-activity-relationship
(SAR) is an approach to fi nding the relationships between the chemical structure (or
structural-related properties) and the biological activity of studied compounds. It
links the chemical structure to a chemical property (e.g., water solubility) or the
biological activity including toxicity.
Keywords Chemical compounds (cid:129) Biological potential (cid:129) Biological activity spec-
trum (cid:129) Structure-activity-relationship
Each chemical compound possesses numerous biological activities. However, its
activity always depends on the object, dose, and participation in the chemical con-
versions or biochemical pathways. On the other hand, the biological potential of the
substance may be discovered under the specifi c experimental conditions.
A s per the Oxford Dictionary, “Biochemistry refers the biological activity of a
substance demonstrated in living organisms.” The biologically active substances are
often from biological origin. Biological activity characterizes the biological effec-
tiveness of a substance and describes the changes caused by biological material like
enzymes, hormones, vitamins, etc., in a tissue or in an organ under constant condi-
L. W. Szajdak (*)
Institute for Agricultural and Forest Environment , Polish Academy of Sciences ,
Str. Bukowska 19 , 60-809 Poznań , Poland
e-mail: [email protected]
© Springer International Publishing Switzerland 2016 1
L.W. Szajdak (ed.), Bioactive Compounds in Agricultural Soils,
DOI 10.1007/978-3-319-43107-9_1
2 L.W. Szajdak
tions as compared with certain international standard. Certain biological activity is
measurable in quantity, and the international unit (IU) corresponds to a certain
amount of a biologically active substance which produces a certain biological
response. However, another measure is the IC —value corresponding to that
50
amount of an effective substance, which inhibits the biochemical reaction in target
organism by 50 % effectiveness. Concentration in this context means the concentra-
tion of a given substance in the target tissue—often in mg/kg or g/kg (Uosukainen
and Pihlaja 2 006 ).
S ome scientists call the b iological potential the biological activity spectrum .
Biological activity spectrum of the compound should be predicted based on the
structure–activity relationships. The biological activity spectrum of a compound
shows compound’s all actions and the participation in the biological, physiological,
and metabolic pathways despite the difference in the experimental conditions. If the
differences in species, sex, age, dose, participation in the metabolic processes and
pathways, etc., are neglected, the biological activity may be identifi ed only qualita-
tively. Thus, “the biological activity spectrum” is defi ned as the “intrinsic” property
of a substance depending only on its structure and physicochemical characteristics
(Filimonov and Poroikov 1 996 ; Filimonov et al. 1 999 ).
T he molecular structure of an organic compound determines its properties (Jurs
et al. 1 988 ).
Molecular Properties
Structures
Structural
Description

The term a ctive substance has been used in this chapter to refer to raw material
(organic matter, mineral and organic soil, peat, moorsh, sapropel) substrates and
growing media for agriculture and horticulture. Relationship between the molecular
structure and biological activity or molecular structure and physical properties can
be investigated for most organic compounds using different analytical methods.
High-performance liquid chromatography (HPLC), gas chromatography, infrared
analysis, UV-VIS spectrophotometry, spectrofl uorimetry, colorimetric test, thermal
analysis, electron paramagnetic resonance, enzyme activity, etc., are recommended
for the quantitative and qualitative determination of chemical and biochemical com-
pounds, their metabolites, and degradation products.
Specifi cation for the active substances should include the tests for (i) appearance,
(ii) identifi cation, (iii) content/assay, (iv) impurities (residual solvents, ash, heavy
metals, and related substances, metabolites, and the products of the degradation),
and (v) other parameters relevant to the individual substances (water content, loss
on drying, the presence or ratio of isomers, optical rotation, melting point and the
clarity, color and pH of solutions).
1 Introduction: Biologically Active Compounds 3
Structure–activity relationship (SAR) is an approach to fi nd the relationships
between chemical structure (or structural-related properties) and its biological
activity of studied compounds. It links the chemical structure to a chemical property
(e.g., water solubility) or biological activity including toxicity. Qualitative SARs
and quantitative SARs are collectively named (Q)SARs. Qualitative relationships
are derived from non–continuous data (e.g., yes or no data), while quantitative rela-
tionships are derived from continuous data (e.g., toxic potency data). The approach
is not new [AFA Cros in 1863 noted in “Action de l’alcool amylique sur l’organisme,”
the relationship between the toxicity of primary aliphatic alcohols and their water
solubility (Chirico and Gramatica 2 012) ]. The concept of structure biodegradability
relationships (SBR) explains the variability in persistence of organic chemicals in
the environment.
T he main concept of SAR is that the structure of compound is responsible for the
activity. Therefore, similar molecules should reveal similar biological activities.
Thus, the SAR approach assumes that the structure of a molecule (e.g., its geomet-
ric, electronic properties) contains the features responsible for its physical, chemi-
cal, and biological properties (Nantasenamat et al. 2 009 , 2 010; Thompson et al.
2 006 ).
B iological activity (e.g., mutagenicity, cancerogenicity, teratogenicity, inhibition
of enzyme activity, toxicity) of substances is governed by their properties, which in
turn are determined by their chemical structure. The objectives of SAR are
twofolds:
(i) To accurately determine the limits of variation in the structure of a chemical
that are consistent with the production of a specifi c effect (e.g., can a chemical
elicit a specifi c toxic endpoint)
(ii) To defi ne the ways, which alters the structure and thereby the overall properties
of a compound to infl uence the endpoint potency (Patani and LaVoie 1 996 ;
Brown 2012 )
The action of biologically active substances in soil depends upon the environ-
mental conditions (such as temperature, light, water, oxygen tension, and availabil-
ity of nutrients). Biologically active substances exert their greatest effects on
increasing the plant yield, when conditions are suboptimal for plant growth.
Chemical compounds may be classifi ed according to several criteria. One com-
mon method is based on the specifi c elements present (oxides, hydrides, halides,
halogens). Organic compounds are those compounds with a backbone of carbon
atoms, and all the remaining compounds are classifi ed as inorganic . As the name
suggests, o rganometallic compounds are organic compounds bonded to metal
atoms. Another classifi cation scheme for chemical compounds is based on the types
of bonds that the compound contains. I onic compounds contain ions and are held
together by the attractive forces among the oppositely charged ions. Common s alt
(sodium chloride) is one of the best-known ionic compounds.
However, molecular compounds contain discrete m olecules , which are held
together by sharing electrons ( c ovalent bonding), e.g., w ater (contains H O mole-
2
cules), m ethane (contains CH molecules), and hydrogen fl uoride (contains HF
4
4 L.W. Szajdak
molecules). Furthermore, another classifi cation system is based on reactivity—spe-
cifi cally, the types of chemical and biochemical reactions, conversions, and path-
ways that the compounds are likely to undergo.
Some biologically active substances act at low concentrations. Phytohormones
can be also considered in the same category as antagonisms as they affect the plant
growth. Vitamins from B group are normal constituents of fertile soils. Their pres-
ence is due to release from organic residues, liberation from plant roots, and synthe-
sis by soil microorganisms. Phenolic acids derived from the lignin decay by
microorganisms infl uence the activity of peroxidase in soils (Stevenson 1 982 ).
T he following organic compounds occur in soil under continuous cropping, and
intensive rotations are ecotoxic and allelopathic (Smyk 1992; Szajdak and
Życzyńska-Bałoniak 1 994 ):
1 . A liphatic and aromatic amines (primary, secondary, tertiary) as the precursors
of nitrozoamines
2 . A mides, imides, esters, derivatives of carboxylic and hydroxycarboxylic acids,
peptides (Fig. 1 .1 )
3. Phenols: hydroxyphenolic acids (p-hydroxybenzoic, p-coumaric, ferulic, sali-
cylic, syringic, vanillic, protocatechuic), catechol, quinone, hydroquinone, res-
orcine, derivatives of o,m,p, p-aminophenols and nitrophenols (Table 1 .1 )
4. Coumarins and their derivatives (Table 1 .2 ) (Fig. 1 .2 and 1 .3 )
5. Terpenoids (saponins, diterpenoids)
6. Flavonoids as per IUPAC nomenclature (Table 1 .3 ):
NH (γ)
2
NH (γ)
2
L DAB L Leu L DAB
L Leu L DAB NH2(γ)
D Fen L DAB NH (γ)
2
D Fen L Tre OH
(γ)H N L DAB L Tre OH
2
H2N L DAB L DAB NH2 L DAB (à)
L DAB
L DAB NH2 (γ)
D DAB NH (γ)
2
L Tre OH
IPEL
D DAB NH2 (γ)
IPEL
(I) (II)
Fig. 1.1 P olymyxin B—the product of Bacillus polymyxa strains. Structure of polymyxin B from
eight (I) or seven (II) of amino acids (Szajdak 2 011 )
Bond CO–NH, T re threonine, DAB L-α,γ-diaminobutyric acid, Fen phenylalanine, Leu leucine,
IPEL isopelargonic acid