Abstract
Medicinal plants are used globally as a valuable source for new drug formulations. They are important to human life from ancient times and have since been used to cure different types of ailments. Their growth, development, overall yield, and production of bioactive compounds such as secondary metabolites are adversely affected by environmental fluctuations (mainly under major abiotic stress conditions). Production of secondary metabolites in medicinal plants also depends on harvest time, seasons, soil type, nutrient supply, altitude, geographical location, stage of plant (juvenile or mature stage), and genotypes or cultivars. The presence of secondary metabolites in medicinal plants has shown several biological and pharmacological activities. Thus, they are important in new drug formulation. Additionally, several secondary metabolites are involved in signaling and controlling the attack of herbivores, microbes, and other plants. This chapter focuses on the secondary metabolites obtained from medicinal plants, their variation at different developmental stages, and the overall impact of resilient environmental conditions on their production.
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1 Introduction
Health is wealth. In consonance with this proverb, human beings have always been in search of various types of medicine to eliminate their illnesses. Plants are the natural source of these medicines mainly due to the presence of secondary metabolites and have been used as medicine in crude extract form. They have been also used to isolate the bioactive compounds in modern medicine and herbal medicine systems (Parveen et al. 2020a). Thus, they play an important role in the development, synthesis, and formulation of new drugs. Right now, numerous plant-based drugs are available in the market, and they have shown a remarkable contribution in disease management. In fact, from the ancient times, several herbal plants have been used as medicine or a source of medicines. For instance, in 2600 BC, the medicinal system in Mesopotamia had thousands of plant-derived medicines. Also, the Egyptian medicine system “Ebers Papyrus” has the written records of 700 drugs obtained from plants (Borchardt 2002; Cragg and Newman 2013; Sneader 2005). Traditional Chinese medicine and Indian Ayurveda and Unani medicine systems also documented evidence for the use of plant-derived medicine over thousands of years (Parveen et al. 2020b; Patwardhan 2005; Unschuld 1986).
A literature survey has shown that several families of plants have been used for medicinal purposes and in the development of new drugs. Some of the important medicinal plants are frequently obtained from Rutaceae, Asteraceae, Apocynaceae, Solanaceae, Caesalpiniaceae, Liliaceae, Piperaceae, Ranunculaceae, Apiaceae, Sapotaceae, Orchidaceae, and many more (Nautiyal et al. 2002; Husen and Rahman 2003; Husen and Faisal 2005; Aftab 2019). Aspirin, atropine, artemisinin, colchicine, digoxin, ephedrine, morphine, physostigmine, pilocarpine, quinine, quinidine, reserpine, taxol, tubocurarine, vincristine, vinblastine, etc., are important drugs obtained from the various medicinal/herbal plants. These drugs are obtained from the whole plant, leaves, roots, shoots, flower, or bark, etc. (Parveen et al. 2020a). For example, the root of Rauvolfia serpentina (Apocynaceae) is used to isolate serpentine, which is useful in the treatment of hypertension. Similarly, Catharanthus roseus is a source of vinblastine used in the treatment of different types of cancer (Iqbal and Srivastava 1997).
Numerous medicinal plants and their parts are a good source of bioactive compounds and/or secondary metabolites (terpenoids, phenolics, and nitrogen-based compounds) and have made a lot of contributions in drug formulation for the treatment of chronic diseases , such as heart disease, cancer, and diabetes (Iqbal 2013). Additionally, many other bioactive compounds obtained from herbal plants and combined with other compounds have shown to enhance the biological activity and are used in drug formulation (Kennedy and Wightman 2011; Shariff 2001). Generally, the significance of medicinal plants depends on the content and production of secondary metabolites. Swift et al. (2004) have reported over 100,000 known secondary metabolites with diverse chemical structures and function. Several factors such as harvest time, seasons, soil type, nutrient supply, altitude, geographical location, stage of plant (juvenile or mature stage), genotypes or cultivars, biotic stress, and abiotic stress (such as temperature variation, drought, salinity, and light intensity) extensively affect various plant processes including plant growth and development, and synthesis, accumulation, and production of secondary metabolites (Arshi et al. 2006a, b; Berini et al. 2018; Chetri et al. 2013; Falk et al. 2007; Iqbal et al. 2018; Ramakrishna and Ravishankar 2011; Zykin et al. 2018). Extraction process may also influence the chemical composition of natural products (Bucar et al. 2013; Jones and Kinghorn 2012). Like food crops and other higher plants, the medicinal plants also cope up with the surrounding adverse environment by producing secondary metabolites which help them to adopt and/or tolerate the stress situations (Berini et al. 2018; Isah 2019; Kroymann 2011). Several secondary metabolites have shown a specific role in defense against herbivores, pests, and pathogens (Bennett and Wallsgrove 1994; Zaynab et al. 2018) (Fig. 19.1). Accordingly, this chapter aims at reviewing the information about the secondary metabolites obtained from medicinal plants, their variation at different developmental stages, and the overall impact of adverse environmental conditions on their production.
Secondary metabolites under adverse environmental conditions and their role in plant defense
2 Secondary Metabolites and Their Production Sites
Herbal medicine is receiving attention in both developed and developing countries because of its natural origin and minimal adverse effects (Lawal and Yunusa 2013; Parveen et al. 2020b). The World Health Organization (WHO) report revealed that over nearly 80% of the global population uses herbal plants to cure human ailments (WHO 2019). Phytochemicals (natural products) are produced by plants via primary and/or secondary metabolism (Huang et al. 2016). They have shown various biological activities and play a key role in plant communication, growth, or defense against competitors, pathogens, or predators (Bachheti et al. 2019; Molyneux et al. 2007). Based on their biosynthetic pathway, secondary metabolites can be categorized into three major groups – phenolic compounds, terpenes, and nitrogen-containing compounds (Fang et al. 2011; Parveen et al. 2020b).
The flavonoids constitute one of the most widespread groups of natural products and are important to humans because they contribute color to plants and many of them, namely, coumestrol, phloridzin, rotenone, rutin, and artemetin. Flavonoids that occur as aglycones, glycosides (O-glycosides and C-glycosides), dimers, and methylated derivatives are physiologically active (Jay et al. 1975; Swain 1976). Glucose is the common sugar present in the flavonoids glycoside although the presence of galactose, rhamnose, xylose, arabinose, mannose, fructose, and apiose is also reported in mono-, di-, or tri-flavonoid glycosides (Harbone and Mabry 1975; Markham 1982). Structurally, flavonoids are benzo-y-pyrone derivatives that resemble coumarin. All the flavonoid aglycones consist of a benzene ring (A) condensed with a six-membered heterocyclic ring (C), which is either a γ-pyrone (chromone) or its dihydro derivative (4-chromone). The 4-chromone substituted by an aryl ring (B) at 2-position gives flavones and dihydroflavonols, and a similar substitution of chromone by aryl ring divides the flavonoids class into flavonoids (2-position) and isoflavonoids (3-position). Flavonols differ from flavanones by OH-group in the 3-position and a double bond at C2–C3 (Fig. 19.2). The common substituents such as free OH and OMe (methoxy group) are reported in flavonoids. In the case of O-glycosides, the C1 of sugar moiety is linked to flavonoid unit through O-atom. A free ortho position to phenolic hydroxyl groups appears to be a common feature that is a prerequisite for the formation of a C-glycosidic linkage in flavonoid (Markham 1982). In different classes of flavonoid C-glycosides (Fig. 19.1), the sugar moiety is attached directly to the ring A by C–C bond and is resistant to acid and enzymatic hydrolysis even after prolonged acid treatment, although partial isomerization often takes place under these conditions.
Basic skeleton of natural occurring (a) flavonoid glycosides and (b) C-glycoside
Terpenoids cover the major and most extensive group of natural plant products, and over 20,000 such structures have been described from plant sources. Isoprene a five-carbon unit, that is, isoprene, is the precursor of all terpenoids. Biosynthetically, they are formed in vivo by the condensation of two C5 precursors, that is, dimethylallyl pyrophosphate and isopentenyl pyrophosphate (IPP), which give rise to C10-intermediate, geranyl pyrophosphate (GPP). This is the immediate precursor of the monoterpenoids and the related monoterpene, and lactones are known as iridoids. GPP can be condensed in turn with another C5 unit of IPP to produce the C15 intermediate, farnesyl pyrophosphate (FPP). This compound is the starting point for the synthesis of sesquiterpenoids. FPP can undergo further extension by linking with another IPP residue to produce the C20 intermediate, geranyl-geranyl pyrophosphate (GGPP). This is the general precursor of all the plant diterpenoids with their C20 base structures. Two molecules of the intermediate FPP can condense together in a further step in terpenoid biosynthesis with the formation of squalene, the C30 precursor of the largest group of isoprenoids, the triterpenoids. Two molecules of GGPP may condense together tail to tail to form a C40 intermediate called phytene, which is the immediate precursor of the yellow carotenoid pigments. The whole class of terpenoids is thus structurally very complex. Polymerization of IPP can occur in plants leading to polymer, which is commonly secreted in special cells as milky latex. Terpenoids have been classified into different classes such as monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpene, and triterpenoids (Fig. 19.3) (Harborne 1998; Nakanishi et al. 1974).
Structures of naturally occurring terpenoids. (a) Monoterpenoids, (b) sesquiterpenoids, (c) diterpenoids, (d) sesterterpenoids, (e) triterpenoids
Nitrogen-containing secondary metabolites contain alkaloids, cyanogenic glycosides, and glucosinolates. Alkaloids contain more than 12,000 nitrogen-containing low-molecular-weight compounds family (Facchini 2001; Khan and Rahman 2017) and are known for their biological activities. Examples of alkaloids are quinine, antineoplastic agents (camptothecin and vinblastine), and strychnine (poison for rats). Precursors for the biosynthesis of alkaloids include tyrosine, lysine, and tryptophan (Khalil 2017; Taiz and Zeiger 2006).
The growth and developmental stage (juvenile or mature phase) of medicinal plants, harvest times, etc. affect the production of secondary metabolites (Table 19.1). The major production sites of secondary metabolites are leaves, flowers, fruits and seeds, roots, and stem. Leaves produce food for plants by the process of photosynthesis . Also, it is used for synthesis and storage site for secondary metabolites. The amount and/or concentration of secondary metabolites in plant leaves are usually affected by harvesting season, leafage, growth stage, etc. (Gomes et al. 2019; Li et al. 2016b; Vazquez-Leon et al. 2017). For instance, it was found that biosynthesis of terpenes (monoterpenes and sesquiterpenoids) starts at cotyledon stage of Melaleuca alternifolia (Southwell and Russell 2002). The highest content of essential oil (eugenol) in Cinnamomum verum was present in a 1-year-old leaf (Li et al. 2016b). However, in some plants, synthesis of compounds starts in the mature leaves. For instance, compounds associated with the sabinene hydrate–terpinen-4-ol–γ-terpinene pathways seem to be formed at later stages of development (Southwell and Russell 2002).
Normally, flowers have a good smell due to the presence of terpenes and aromatic compounds in them; their synthesis and storage are also affected by different developmental stages (Srivastava and Iqbal 1994). A study on volatile oils content of flower buds of Magnolia zenii at different growth stages found a remarkable difference in oil content at different growth stages (Hu et al. 2015). Volatile oil yield first increases and then decreases with the growth of flower buds, while maximum oil yield was obtained in October (Hu et al. 2015). Figueiredo et al. (2008) reported that the content of 1,8-cineole and camphor increases with the development stage of the flowers of Achillea millefolium , while the content of azulene decreases. In the case of Antirrhinum majus , contents of ocimene and elemene quickly increased on the second day after flowering and decreased after attaining peak on the sixth day (Dudareva et al. 2003). The developmental stages of fruit and seed also have a remarkable influence on the secondary metabolites content and composition. A study by Liang et al. (2006) has shown that the highest amount of essential oils (volatile oil) is present in citrus fruit when it is light yellow. Wu et al. (2013) also reported that the yield of essential oil increased the maturation process and the contents of β-pinene, α-thujone, carene, and γ-terpinene in Citrus medica change significantly during the maturation stage. Also, the maximum content of morphine was reported at the maturity of Papaver somniferum roots (Shukla and Singh 2001). The content of dicoffee quinic acids decreases with the developmental stage, while the content of quinic acid was the highest in the early developmental stage in coffee seeds (Lepelley et al. 2007). The highest saponins content in the root of Panax notoginseng was found when the plant was 3-year-old (Hong et al. 2005). Further details are presented in Table 19.1.
3 Role of Secondary Metabolites Under Adverse Environment
During the entire life span, plants come across both abiotic and biotic stresses. Secondary metabolites exhibit a significant role in tolerance and adaptation of plants to adverse environmental conditions (Anjum et al. 2014). Additionally, the biosynthesis of secondary metabolites is also influenced under various environmental conditions (Iqbal et al. 2011). Further details of different types of stresses encountered by the plant are shown in Fig. 19.1.
3.1 Biotic Stress
Like crop plants, medicinal plant growth and production are also affected by potential biotic enemies, such as bacteria, viruses, fungi, nematodes, mites, insects, mammals, and other herbivorous animals. Due to sessile nature, plants are unable to change their position to get rid of such enemies. In this negative situation, they protect themselves by producing secondary metabolites. For instance, phytoalexins having antimicrobial activity are produced by plants on attack of pathogen (Taiz and Zeiger 2006). Similarly, Verma and Shukla (2015) have reported that when a plant undergoes fungal infections, significant variation occurs in phenolics content. Kim et al. (2008) have reported that among the various secondary metabolites, the phenolic compounds play a vital role in plant defense against pathogens and insects attack. Alkaloids are also involved in plant defense and are produced in response to attacks by a microorganism (Joosten and van Veen 2011). It has been also reported that the content of trigonelline, camptothecin, and castanospermine increased due to reactions with fungus inoculum (Jia et al. 2016). Some specific enzymes are capable of avoiding the attack of any unsuitable organisms. For instance, the activity of polyphenol oxidase increases in wounded plants attacked by pests or infected by pathogens (Vanitha et al. 2009). Some plants also produce o-quinones, which act as antimicrobial agents and protect plants (Constabel et al. 2000).
3.2 Abiotic Stress
Climate change and an environmental variation, such as temperature, drought, salinity, solar radiation, and air pollution, have been reported to affect the production of secondary metabolites (De Castro et al. 2020; Ferreira et al. 2016; Iqbal et al. 2018; Kulak et al. 2020; Nascimento et al. 2015; Qureshi et al. 2013; Sampaio et al. 2016; Sharma et al. 2019; Zhou et al. 2017). Some of the major abiotic stress conditions and plant response in terms of secondary metabolite production are discussed in the following.
3.2.1 Temperature Stress
Change in temperature affects plant growth and secondary metabolite content due to changes in the metabolic pathways that control physiology, signaling, and defense mechanisms. Studies have shown that the production of secondary metabolites increases in response to elevated temperatures in Pringlea antiscorbutica (Hummel et al. 2004) and Panax quinquefolius (Jochum et al. 2007). However, in the case of Pseudotsuga menziesii , high temperature has reduced the content of monoterpene (Snow et al. 2003). Some studies such as Ruelland et al. (2009) and Sevillano et al. (2009) have suggested that low temperature generates reactive oxygen species (ROS), and to neutralize their effect, the plant generates antioxidative enzymes. However, almost all the abiotic stresses, including high- and low-temperature stresses, cause oxidative damage and generate ROS in plants (Aref et al. 2016; Siddiqi and Husen 2017, 2019). Thus, plants evolved a range of tolerance mechanisms to manage the damage produced by these stresses, such as activation of antioxidative enzymes, and the accumulation of compatible solutes that effectively scavenge ROS. The chemical composition of essential oil has also been affected due to changes in temperature conditions. For instance, the effect of cold temperature on essential oil composition Origanum dictamnus was examined by Lianopoulou and Bosabalidis (2014). This investigation has shown that the main components of essential oil of Origanum dictamnus were p-cymene, carvacrol, γ-terpinene, and borneol; however, in winter, content of p-cymene was 59.2%, whereas in summer, carvacrol content was 42%. Low temperature increases the accumulation of withanolides (steroids) in the leaves of Withania somnifera (Khan et al. 2015; Kumar et al. 2012). Also, in transgenic plants of this species, the same trend was noticed when exposed to low temperature, that is, increase in withanolide content when plant exposed to low temperature (Saema et al. 2016). Rivero et al. (2001) studied the effect of high temperature on tomato plants and found that high temperature causes accumulation of phenolic contents. Wu et al. (2016) studied polyphenols in different sorghum genotypes under high-temperature stress . They have suggested that the brown sorghum was rich in phenolic profile, and thus exhibited a greater temperature tolerance. Further details associated with medicinal plants and their response under temperature stress are given in Table 19.2.
3.2.2 Drought Stress
Global climate change is increasing the frequency of severe drought conditions. Drought stress conditions affect adversely growth, development, and the overall physiological and biochemical status of plants (Embiale et al. 2016; Getnet et al. 2015; Husen 2010; Husen et al. 2014). Similarly, drought stress affects the production of secondary metabolite contents (Caser et al. 2019; Podda et al. 2019). Plants accumulate more secondary metabolites in water-stressed conditions and a decrease in biomass production (Kleinwächter and Selmar 2014). A study was performed on Adonis amurensis and A. pseudoamurensis to check the effect of drought on secondary metabolites and changes in growth and physiology. In the early stage, both the perennial plants showed an adaptive change to drought stress and a significant increase in flavonoids and total phenols content in response to drought stress (Gao et al. 2020). In another study, García-Caparrós et al. (2019) observed the impact of drought stress on the essential oil content of Lavandula latifolia, Mentha piperita, Salvia sclarea, S. lavandulifolia, Thymus mastichina, and T. capitatus. The essential oil content of Lavandula latifolia and Salvia sclarea plants showed a reduction under drought stress conditions. Chavoushi et al. (2020) examined Carthamus tinctorius and found that secondary metabolites (flavonoids, anthocyanin, phenol, and phenylalanine ammonia-lyase activity) increased under drought stress conditions. Drought stress also increased the concentration of monoterpene in Salvia officinalis (Nowak et al. 2010), and its concentration was more than the reduction in biomass as compared to control plants. A similar type of result (increases in monoterpenes concentration and biomass reduction) was observed in another experiment conducted on Petroselinum crispum under drought stress condition (Petropoulos et al. 2008). An increase in secondary metabolites content of total anthocyanins, phenolics, and total flavonoids was also observed in Labisia pumila when it was kept under high water stress conditions (50% evapotranspiration) (Jaafar et al. 2012). Further details associated with medicinal plants and their responses to drought stress are given in Table 19.3.
3.2.3 Salinity Stress
Salinity stress is another important global problem that negatively affects plant growth and production (Husen et al. 2016, 2018, 2019; Hussein et al. 2017; Isayenkov and Maathuis 2019). It also affects the accumulation of secondary metabolites in plant tissues (Arshi et al. 2002; Cui et al. 2019; Hakeem et al. 2013; Ibrahim et al. 2019; Wang et al. 2015). In Gossypium hirsutum , salinity stress enhanced the secondary metabolism as indicated by the increased accumulation of gossypol, flavonoids, and tannin (Wang et al. 2015). Germination of Prosopis strombulifera seed was severely affected by increased salinity (Sosa et al. 2005). Further, seed germination of some other medicinal plants decreases under salt stress, as in Ocimum basilicum (Miceli et al. 2003), Petroselinum hortense (Ramin 2005), and Thymus maroccanus (Belaqziz et al. 2009). Seedling growth is also negatively affected by salinity, as in basil (Ramin 2005), chamomile, and marjoram (Ali et al. 2007) and Thymus maroccanus (Belaqziz et al. 2009). There are inconsistent reports on the effect of salt stress on essential oil content. In some studies, a negative effect of salt stress in essential oil yield is noticed, as in Trachyspermum ammi (Ashraf and Orooj 2006), Mentha piperita (Tabatabaie and Nazari 2007), Thymus maroccanus (Belaqziz et al. 2009), and basil (Said-Al Ahi et al. 2010). In these cases, oil content decreased under salt stress conditions. Nonetheless, in Matricaria recutita, the main chemical constituents of essential oil such as α-bisabololoxide B, α-bisabolonoxide A, chamazulene, and α-bisabolol oxide A increased under salt stress conditions (Baghalian et al. 2008). In Origanum vulgare, the main chemical constituents of essential oil carvacrol were found to decrease in salt stress, whereas p-cymene and γ-terpinene content increase under normal condition (Said-Al Ahl and Hussein 2010). De Castro et al. (2020) observed the effect of salinity on essential oil profile, growth, and morphology in Lippia alba and found that increase in linalool and decrease in eucalyptol levels at higher salt stress conditions. Further details associated with medicinal plants and their response to salinity stress are given in Table 19.4.
3.2.4 Light Intensity
Light intensity determines the concentration of plant secondary metabolites (Jurić et al. 2020; Pedroso et al. 2017; Tavakoli et al. 2020; Thoma et al. 2020). Light may suppress or stimulate the production of various secondary metabolites depending on its quantity (intensity) or duration (photoperiod). Production of flavonoid, phenolic compound, and terpenoids in root and shoots of Hordeum vulgare got stimulated in the presence of full sunlight as well as in monochromatic light, that is, blue light (Klem et al. 2019). Similarly, the concentration of scutellarin (phenols) in leaves of Erigeron breviscapus increased in full sunlight (Zhou et al. 2016). Li et al. (2018) have also reported that the alkaloids concentration in root, shoots, and essential oils in leaves of Mahonia breviracema increases in the presence of full sunlight. This study also found that hexadecanoic acid in leaves increases when Mahonia bodinieri was grown under 50% stress of light availability. Also, Kong et al. (2016) examined some other parts of Mahonia bodinieri and concluded that under 30–50% stress, the alkaloid content get enhanced, and in the case of Flourensia cernua, the alkaloids content of leaves such as sabinene, β-pinene, borneol, bornyl acetate, and Z-jasmone was increased when half of the regular sunlight available for plants was provided, that is, in 50% light stress. Further details associated with medicinal plants and their response to light are given in Table 19.5.
3.2.5 Heavy Metal Stress
The secondary metabolites production in plants also gets affected by the presence of heavy metals (Iqbal et al. 2015; Jabeen et al. 2009). Various researchers have claimed this, such as Manquian-Cerda et al. (2016) reported that in the presence of cadmium, the concentration of chlorogenic acid increases in Vaccinium corymbosum plantlets, while Sá et al. (2015) reported in their study that the production of carvone (essential oils) in Mentha crispa gets stimulated in the presence of lead. De and De (2011) investigated the impact of the treatment of chromium, nickel, cadmium, and copper on Trigonella foenum-graecum and found that the production of steroids, that is, diosgenin, gets inhibited by chromium and nickel, whereas cadmium and copper stimulated its production. Effect of chromium on the concentration of secondary metabolites of Phyllanthus amarus was studied by Rai and Mehrotra (2008). They have concluded that the concentration of phyllanthin and hypophyllanthin increases under chromium exposure. Sinha and Saxena (2006) found that in the presence of iron, the production of bacoside-A in roots and leaves of Bacopa monnieri increases, whereas the production of cysteine in roots increases and there is no effect in the production of cysteine in leaves. Similarly, in the presence of cadmium, there is no effect on the concentration of umbelliferone in Matricaria chamomilla (Kováčik et al. 2006). Narula et al. (2005) studied the plant culture of Dioscorea bulbifera and found that in the presence of copper, the production of diosgenin increases. The production of Eugenol (in the whole plant) and proline (in leaves) of Ocimum tenuiflorum increases in the presence of chromium (Rai et al. 2004). Murch et al. (2003) reported that the production of pseudohypericin and hypericin decreases in the presence of nickel in Hypericum perforatum , whereas the production of hyperforin gets completely inhibited under similar conditions. Further details associated with medicinal plants and their response to heavy metals are given in Table 19.6.
4 Conclusion
Human beings depend on plants for fulfilling their various needs. Medicinal/herbal plants are a good source of secondary metabolites used in pharmaceutical industries for drug synthesis and formulation. Concentration and content of secondary metabolites depend (increase/decrease) on harvest time, seasons, soil type, nutrient supply, altitude, geographical location, stage of plant (juvenile/mature), and genotypes or cultivars. Their production is under biotic (by the attack of herbivores, pets, and pathogens) and abiotic (such as temperature variation, drought, salinity, light intensity, and heavy metals) stresses. Secondary metabolites have a significant role in the tolerance and adaptation of plants to adverse environmental conditions. However, their synthesis mechanism is not fully examined, and further investigation is required to obtain the maximum production of secondary metabolites from important medicinal plants under normal as well as adverse environmental conditions.
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Bachheti, A., Deepti, Bachheti, R.K., Husen, A. (2021). Medicinal Plants and Their Pharmaceutical Properties Under Adverse Environmental Conditions. In: Husen, A. (eds) Harsh Environment and Plant Resilience. Springer, Cham. https://doi.org/10.1007/978-3-030-65912-7_19
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