Abstract
Plants constitute nowadays an important source for the discovery of new products of medicinal value for drug development, food additives, and cosmetic ingredients. High-value plant derivatives include phenolic compounds, terpenes and terpenoids, alkaloids, phytoalexins, among others, all of which biosynthesized as a defensive strategy by plants to respond to perturbations under certain environmental conditions. Although plants produce a number of therapeutical products, either already on the market or under clinical trial, the amounts obtained from natural sources are still very minute or difficult to synthesize at an industrial level because of the complex chemical composition and chirality exhibited by these compounds. Nonetheless, as natural bioactive-oriented researches intensify—from large-scale epidemiological and interventional studies to innovative biotechnological tools pursuing compound refinement and production at the industrial level—, one may expect the upcoming years to be determinant for plant secondary metabolites to achieve their highest value in the most diverse technological and pharmacological domains. In this chapter, we discuss various aspects of plant secondary metabolites, including their biosynthetic pathways, health-promoting properties, and sources of medical products for commercial and pharmaceutical applications.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Abdalla MA, Mühling KH (2019) Plant-derived sulfur containing natural products produced as a response to biotic and abiotic stresses: a review of their structural diversity and medicinal importance. J Appl Bot Food Qual 92:204–215
Ahmed S, Kovinich N (2021) Regulation of phytoalexin biosynthesis for agriculture and human health. Phytochem Rev 20(2):483–505
Ahmed NU et al (2014) Characterization of dihydroflavonol 4-reductase (DFR) genes and their association with cold and freezing stress in Brassica rapa. Gene 550:46–55
Anthoni C et al (2006) Mechanisms underlying the anti-inflammatory actions of boswellic acid derivatives in experimental colitis. Am J Physiol Gastrointest Liver Physiol 290(6):G1131–G1137
Appalasamy S et al (2014) Antimicrobial activity of artemisinin and precursor derived from in vitro plantlets of Artemisia annua L. Biomed Res Int 2014:215872
Araújo FF et al (2021) Polyphenols and their applications: an approach in food chemistry and innovation potential. Food Chem 338:127535
Arendt P et al (2017) An endoplasmic reticulum-engineered yeast platform for overproduction of triterpenoids. Metab Eng 40:165–175
Ashour M, Wink M, Gershenzon J (2018) Biochemistry of terpenoids: monoterpenes, sesquiterpenes and diterpenes. Annu Plant Rev 258–303. https://doi.org/10.1002/9781119312994.apr0427
Bahi A et al (2014) β-Caryophyllene, a CB2 receptor agonist produces multiple behavioral changes relevant to anxiety and depression in mice. Physiol Behav 135:119–124
Bakkali F et al (2008) Biological effects of essential oils—a review. Food Chem Toxicol 46(2):446–475
Bell EA (2003) Nonprotein amino acids of plants: significance in medicine, nutrition, and agriculture. J Agric Food Chem 51(10):2854–2865
Bent S et al (2006) Saw palmetto for benign prostatic hyperplasia. N Engl J Med 354(6):557–566
Berges RR, Kassen A, Senge T (2000) Treatment of symptomatic benign prostatic hyperplasia with beta-sitosterol: an 18-month follow-up. BJU Int 85(7):842–846
Bhattacharyya D et al (2007) Initial exploratory observational pharmacology of Valeriana wallichii on stress management: a clinical report. Nepal Med Coll J 9(1):36–39
Bi X et al (2017) Anti-inflammatory effects, SAR, and action mechanism of monoterpenoids from Radix Paeoniae Alba on LPS-stimulated RAW 264.7 cells. Molecules 22(5)
Bian G, Deng Z, Liu T (2017) Strategies for terpenoid overproduction and new terpenoid discovery. Curr Opin Biotechnol 48:234–241
Bolarinwa IF, Orfila C, Morgan MR (2015) Determination of amygdalin in apple seeds, fresh apples and processed apple juices. Food Chem 170:437–442
Bolarinwa IF et al (2016) A review of cyanogenic glycosides in edible plants. In: Soloneski S, Larramendy ML (eds) Toxicology—new aspects to this scientific conundrum. IntechOpen
Bound DJ, Murthy PS, Srinivas P (2015) Synthesis and antibacterial properties of 2,3-dideoxyglucosides of terpene alcohols and phenols. Food Chem 185:192–199
Boyom FF et al (2011) Antiplasmodial volatile extracts from Cleistopholis patens Engler & Diels and Uvariastrum pierreanum Engl. (Engl. & Diels) (Annonaceae) growing in Cameroon. Parasitol Res 108(5):1211–1217
Carnesecchi S et al (2001) Geraniol, a component of plant essential oils, inhibits growth and polyamine biosynthesis in human colon cancer cells. J Pharmacol Exp Ther 298(1):197–200
Carson CF, Hammer KA, Riley TV (2006) Melaleuca alternifolia (Tea Tree) oil: a review of antimicrobial and other medicinal properties. Clin Microbiol Rev 19(1):50–62
Castañeda-Ovando A et al (2009) Chemical studies of anthocyanins: a review. Food Chem 113(4):859–871
Chan YW et al (2016) Plasma polymerized carvone as an antibacterial and biocompatible coating. Mater Sci Eng C Mater Biol Appl 68:861–871
Chang C-D et al (2016) Ursolic acid suppresses hepatitis B virus X protein-mediated autophagy and chemotherapeutic drug resistance. Anticancer Res 36(10):5097
Chatzivasileiou AO et al (2019) Two-step pathway for isoprenoid synthesis. Proc Natl Acad Sci USA 116(2):506
Chen D-Z et al (2001) Indole-3-carbinol and diindolylmethane induce apoptosis of human cervical cancer cells and in murine HPV16-transgenic preneoplastic cervical epithelium. J Nutr 131(12):3294–3302
Chen TC, Fonseca COD, Schönthal AH (2015a) Preclinical development and clinical use of perillyl alcohol for chemoprevention and cancer therapy. Am J Cancer Res 5(5):1580–1593
Chen X et al (2015b) IVSE, isolated from Inula japonica, suppresses LPS-induced NO production via NF-κB and MAPK inactivation in RAW264.7 cells. Life Sci 124:8–15
Chen J et al (2020) Structure-antioxidant activity relationship of methoxy, phenolic hydroxyl, and carboxylic acid groups of phenolic acids. Sci Rep 10:2611
Cheynier V et al (2013) Plant phenolics: recent advances on their biosynthesis, genetics, and ecophysiology. Plant Physiol Biochem 72:1–20
Chimi H et al (1991) Peroxyl and hydroxyl radical scavenging activity of some natural phenolic antioxidants. J Am Oil Chem Society 68:307–312
Chiocchio I et al (2021) Plant secondary metabolites: an opportunity for circular economy. Molecules 26(2)
Cho M et al (2016) The antitumor effects of geraniol: modulation of cancer hallmark pathways (Review). Int J Oncol 48(5):1772–1782
Cholbi MR, Paya M, Alcaraz MJ (1991) Inhibitory effects of phenolic compounds on carbon tetrachloride-induced microsomal lipid peroxidation. Experientia 47(2):195–199
Clomburg JM, Crumbley AM, Gonzalez R (2017) Industrial biomanufacturing: the future of chemical production. Science 355(6320):aag0804
Clomburg JM et al (2019) The isoprenoid alcohol pathway, a synthetic route for isoprenoid biosynthesis. Proc Natl Acad Sci USA 116(26):12810
Cravens A, Payne J, Smolke CD (2019) Synthetic biology strategies for microbial biosynthesis of plant natural products. Nat Commun 10(1):2142
Crespo-Ortiz MP, Wei MQ (2012) Antitumor activity of artemisinin and its derivatives: from a well-known antimalarial agent to a potential anticancer drug. J Biomed Biotechnol 2012:247597
Cruz L et al (2022) Natural and synthetic flavylium-based dyes: the chemistry behind the color. Chem Rev 122(1):1416–1481
de Cássia da Silveira e Sá R, Andrade LN, de Sousa DP (2013) A review on anti-inflammatory activity of monoterpenes. Molecules 18(1):1227–1254
De Gregorio C et al (2017) Genistein supplementation and cardiac function in postmenopausal women with metabolic syndrome: results from a Pilot Strain-Echo Study. Nutrients 9(6)
de Morais J et al (2020) Antioxidant activity and bioaccessibility of phenolic compounds in white, red, blue, purple, yellow and orange edible flowers through a simulated intestinal barrier. Food Res Int 131:109046
Dermatology A (2014) A prospective split-face double-blind randomized placebo-controlled trial to assess the efficacy of vitamin C and ferulic acid serum postfractional ablative laser for skin rejuvenation. J Am Acad Dermatol 70(5):AB13
De Sousa IP, Sousa Teixeira MV, Jacometti Cardoso Furtado NA (2018) An overview of biotransformation and toxicity of diterpenes. Molecules 23(6):1387
Devane WA et al (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258(5090):1946–1949
Dey P et al (2020) Analysis of alkaloids (indole alkaloids, isoquinoline alkaloids, tropane alkaloids). Recent Adv Nat Prod Anal 505–567
Dias R et al (2021) Recent advances on dietary polyphenol’s potential roles in Celiac disease. Trends Food Sci Technol 107:213–225
Dogan G et al (2017) Chemical composition and biological activities of leaf and fruit essential oils from Eucalyptus camaldulensis. Zeitschrift für Naturforschung C 72(11-12):483–489
Domonkos I et al (2013) Carotenoids, versatile components of oxygenic photosynthesis. Prog Lipid Res 52(4):539–561
Duangmano S et al (2010) Antiproliferative effects of cucurbitacin B in breast cancer cells: down-regulation of the c-Myc/hTERT/telomerase pathway and obstruction of the cell cycle. Int J Mol Sci 11(12):5323–5338
Dudley QM, Karim AS, Jewett MC (2015) Cell-free metabolic engineering: biomanufacturing beyond the cell. Biotechnol J 10(1):69–82
Dzhakhangirov FN et al (1997) Diterpenoid alkaloids as a new class of antiarrhythmic agents. Structure-activity relationship. Chem Nat Comp 33(2):190–202
Dziedzic S, Hudson B (1983) Polyhydroxy chalcones and flavanones as antioxidants for edible oils. Food Chem 12(3):205–212
Efferth T, Kaina B (2010) Toxicity of the antimalarial artemisinin and its derivatives. Crit Rev Toxicol 40(5):405–421
Escobar-Cévoli R et al (2017) An overview of global flavonoid intake and its food sources. In: Flavonoids-from biosynthesis to human health
Espíndola K et al (2019) Chemical and pharmacological aspects of caffeic acid and its activity in hepatocarcinoma. Front Oncol 9:541
Feldo M et al (2019) Effect of diosmin administration in patients with chronic venous disorders on selected factors affecting angiogenesis. Molecules 24(18)
Fenger J-A et al (2020) The fate of acylated anthocyanins in mildly heated neutral solution. Dyes Pigment 178:108326
Forslund K et al (2004) Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus. Plant Physiol 135(1):71–84
Frampton JE (2013) Crofelemer: a review of its use in the management of non-infectious diarrhoea in adult patients with HIV/AIDS on antiretroviral therapy. Drugs 73(10):1121–1129
Galle M et al (2014) Suppression by geraniol of the growth of A549 human lung adenocarcinoma cells and inhibition of the mevalonate pathway in culture and in vivo: potential use in cancer chemotherapy. Nutr Cancer 66(5):888–895
Graziose R, Lila MA, Raskin I (2010) Merging traditional Chinese medicine with modern drug discovery technologies to find novel drugs and functional foods. Curr Drug Discov Technol 7(1):2–12
Gupta R et al (2007) An overview of Indian novel traditional medicinal plants with anti-diabetic potentials. Afr J Tradit Complement Altern Med AJTCAM 5(1):1–17
Guzmán-Gutiérrez SL et al (2015) Linalool and β-pinene exert their antidepressant-like activity through the monoaminergic pathway. Life Sci 128:24–29
Haneklaus S, Schnug E (2004) Significance of secondary nitrogen metabolites for food quality. In: Amâncio S, Stulen I (eds) Nitrogen acquisition and assimilation in higher plants, Plant ecophysiology, vol 3. Springer, Dordrecht, pp 231–259. https://doi.org/10.1007/978-1-4020-2728-4_9
Hassan STS et al (2018) In vitro study of multi-therapeutic properties of Thymus bovei Benth. Essential oil and its main component for promoting their use in clinical practice. J Clin Med 7(9)
Heim KE, Tagliaferro AR, Bobilya DJ (2002) Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J Nutr Biochem 13(10):572–584
Heleno S et al (2015) Bioactivity of phenolic acids: metabolites versus parent compounds: a review. Food Chem 173:501–513
Hensel H, Zotterman Y (1951) The effect of menthol on the thermoreceptors. Acta Physiol Scand 24(1):27–34
Herrera-Balandrano D et al (2021) Blueberry anthocyanins: an updated review on approaches to enhancing their bioavailability. Trends Food Sci Technol 118:808–821
Hincks JR et al (1991) DNA cross-linking in mammalian cells by pyrrolizidine alkaloids: structure-activity relationships. Toxicol Appl Pharmacol 111(1):90–98
Hoballah ME et al (2007) Single gene-mediated shift in pollinator attraction in Petunia. Plant Cell 19(3):779–790
Hsu JL et al (2011) Costunolide induces apoptosis through nuclear calcium2+ overload and DNA damage response in human prostate cancer. J Urol 185(5):1967–1974
Hussein RA, El-Anssary AA (2018) Plants secondary metabolites: the key drivers of the pharmacological actions of medicinal plants. In: Builders PF (ed) Herbal medicine. IntechOpen
Idrees M et al (2020) Multimodal role of amino acids in microbial control and drug development. Antibiotics (Basel) 9(6):330
Iwasa K et al (1998) Antimalarial activity and structure-activity relationships of protoberberine alkaloids. Eur J Med Chem 33(1):65–69
Jamwal K, Bhattacharya S, Puri S (2018) Plant growth regulator mediated consequences of secondary metabolites in medicinal plants. J Appl Res Med Aromat Plants 9:26–38
Jansen DJ, Shenvi RA (2014) Synthesis of medicinally relevant terpenes: reducing the cost and time of drug discovery. Future Med Chem 6(10):1127–1148
Jeppesen PB et al (2006) Can stevioside in combination with a soy-based dietary supplement be a new useful treatment of type 2 diabetes? An in vivo study in the diabetic goto-kakizaki rat. Rev Diabet Stud RDS 3(4):189–199
Jokioja J, Yang B, Linderborg K (2021) Acylated anthocyanins: a review on their bioavailability and effects on postprandial carbohydrate metabolism and inflammation. Compr Rev Food Sci Food Saf 20(6):5570–5615
Jordão FM, Kimura EA, Katzin AM (2011) Isoprenoid biosynthesis in the erythrocytic stages of Plasmodium falciparum. Mem Inst Oswaldo Cruz 106(Suppl 1):134–141
Juergens UR et al (2003) Anti-inflammatory activity of 1.8-cineol (eucalyptol) in bronchial asthma: a double-blind placebo-controlled trial. Respir Med 97(3):250–256
Kang A, Lee TS (2016) Chapter 2—Secondary metabolism for isoprenoid-based biofuels. In: Eckert CA, Trinh CT (eds) Biotechnology for biofuel production and optimization. Elsevier, Amsterdam, pp 35–71
Kang A et al (2016) Isopentenyl diphosphate (IPP)-bypass mevalonate pathways for isopentenol production. Metab Eng 34:25–35
Kharadze M et al (2018) Anthocyanins and antioxidant activity of red wines made from endemic grape varieties. Ann Agrarian Sci 16(2):181–184
Khokhani D et al (2013) Discovery of plant phenolic compounds that act as type III secretion system inhibitors or inducers of the fire blight pathogen, Erwinia amylovora. Appl Environ Microbiol 79(18):5424–5436
Khoo HE et al (2017) Anthocyanidins and anthocyanins: colored pigments as food, pharmaceutical ingredients, and the potential health benefits. Food Nutr Res 61(1):1361779
Kim SH et al (2012) Geraniol induces cooperative interaction of apoptosis and autophagy to elicit cell death in PC-3 prostate cancer cells. Int J Oncol 40(5):1683–1690
Kim WS et al (2015a) Anti-inflammatory, antioxidant and antimicrobial effects of artemisinin extracts from Artemisia annua L. Korean J Physiol Pharmacol 19(1):21–27
Kim S et al (2015b) Antimicrobial action of oleanolic acid on Listeria monocytogenes, Enterococcus faecium, and Enterococcus faecalis. PLoS One 10(3):e0118800–e0118800
Kim JH et al (2017) Role of ginsenosides, the main active components of Panax ginseng, in inflammatory responses and diseases. J Ginseng Res 41(4):435–443
Kim J-E et al (2019) Tailoring the Saccharomyces cerevisiae endoplasmic reticulum for functional assembly of terpene synthesis pathway. Metab Eng 56:50–59
Koleva II et al (2012) Alkaloids in the human food chain–natural occurrence and possible adverse effects. Mol Nutr Food Res 56(1):30–52
Krga I, Milenkovic D (2019) Anthocyanins: from sources and bioavailability to cardiovascular-health benefits and molecular mechanisms of action. J Agric Food Chem 67(7):1771–1783
Kumar S et al (2010) Clinical trials and progress with paclitaxel in ovarian cancer. Int J Womens Health 2:411–427
Lay F, Anderson M (2005) Defensins-components of the innate immune system in plants. Curr Protein Pept Sci 6(1):85–101
Lee SB et al (2007) The antimicrobial activity of essential oil from Dracocephalum foetidum against pathogenic microorganisms. J Microbiol 45(1):53–57
Lee TK et al (2017) Pinecone of Pinus koraiensis inducing apoptosis in human lung cancer cells by activating caspase-3 and its chemical constituents. Chem Biodivers 14(4)
Lewinska A et al (2017) Ursolic acid-mediated changes in glycolytic pathway promote cytotoxic autophagy and apoptosis in phenotypically different breast cancer cells. Apoptosis 22(6):800–815
Li J, Zhang L, Liu W (2018) Cell-free synthetic biology for in vitro biosynthesis of pharmaceutical natural products. Synth Syst Biotechnol 3(2):83–89
Li J-x, Wu J-q, Cai Q-r (2020a) Research progresses on the synthetic biology of terpenes in Saccharomyces cerevisiae. Biotechnol Bull 36(12):199–207
Li Z et al (2020b) Sesquiterpenes in grapes and wines: occurrence, biosynthesis, functionality, and influence of winemaking processes. Compr Rev Food Sci Food Saf 19(1):247–281
Lin JG et al (2002) Effects of garlic components diallyl sulfide and diallyl disulfide on arylamine N-acetyltransferase activity and 2-aminofluorene-DNA adducts in human promyelocytic leukemia cells. Am J Chin Med 30(02n03):315–325
Lin M et al (2019) Quinoa secondary metabolites and their biological activities or functions. Molecules 24(13):2512
Liu J et al (2020) Characterization of phenolic acid antimicrobial and antioxidant structure-property relationships. Pharmaceutics 12:419
Lorigooini Z, Jamshidi-kia F, Dodman S (2020) Chapter 8—Analysis of sesquiterpenes and sesquiterpenoids. In: Sanches Silva A et al (eds) Recent advances in natural products analysis. Elsevier, pp 289–312
Ma T et al (2019) Lipid engineering combined with systematic metabolic engineering of Saccharomyces cerevisiae for high-yield production of lycopene. Metab Eng 52:134–142
Maeda H, Dudareva N (2012) The shikimate pathway and aromatic amino acid biosynthesis in plants. Annu Rev Plant Biol 63(1):73–105
Magnard JL et al (2015) Plant volatiles. Biosynthesis of monoterpene scent compounds in roses. Science 349(6243):81–83
Maia MF, Moore SJ (2011) Plant-based insect repellents: a review of their efficacy, development and testing. Malar J 10(1):S11
Majdalawieh AF, Fayyad MW, Nasrallah GK (2017) Anti-cancer properties and mechanisms of action of thymoquinone, the major active ingredient of Nigella sativa. Crit Rev Food Sci Nutr 57(18):3911–3928
Mandal S, Chakraborty D, Dey S (2010) Phenolic acids act as signaling molecules in plant-microbe symbioses. Plant Signal Behav 5(4):359–368
Mansour MH et al (2013) Garlic (Allium sativum) down-regulates the expression of angiotensin II AT(1) receptor in adrenal and renal tissues of streptozotocin-induced diabetic rats. Inflammopharmacology 21(2):147–159
Maoka T (2020) Carotenoids as natural functional pigments. J Nat Med 74(1):1–16
Matera R et al (2015) Acylated anthocyanins from sprouts of Raphanus sativus cv. Sango: isolation, structure elucidation and antioxidant activity. Food Chem 166:397–406
Mazid M, Khan T, Mohammad F (2011) Role of secondary metabolites in defense mechanisms of plants. Biol Med 3(2):232–249
Melrose J (2019) The glucosinolates: a sulphur glucoside family of mustard anti-tumour and antimicrobial phytochemicals of potential therapeutic application. Biomedicines 7(3):62
Mendoza J et al (2018) Rationalizing the color in heavenly blue anthocyanin: a complete kinetic and thermodynamic study. J Phys Chem B 122:4982–4992
Miller JA et al (2013) Human breast tissue disposition and bioactivity of limonene in women with early-stage breast cancer. Cancer Prev Res (Phila) 6(6):577–584
Mücke M et al (2018) Cannabis-based medicines for chronic neuropathic pain in adults. Cochrane Database Syst Rev (3)
Mueller KO, Meyer G, Klinkowski M (1939) Physiologisch-genetische Untersuchungen über die Resistenz der Kartoffel gegenüber Phytophthora infestans. Naturwissenschaften 27(46):765–768
Nabavi SF et al (2015) Curcumin: a natural product for diabetes and its complications. Curr Top Med Chem 15(23):2445–2455
Nattela F et al (1999) Benzoic and cinnamic acid derivatives as antioxidants: structure−activity relation. J Agric Food Chem 47(4):1453–1459
Nguyen Q-M et al (2021) Recent advances in effector-triggered immunity in plants: new pieces in the puzzle create a different paradigm. Int J Mol Sci 22(9):4709
Nosten F, White NJ (2007) Artemisinin-based combination treatment of falciparum malaria. Am J Trop Med Hyg 77(6 Suppl):181–192
Oberlies NH, Kroll DJ (2004) Camptothecin and taxol: historic achievements in natural products research. J Nat Prod 67(2):129–135
Oliveira H et al (2019) Purple-fleshed sweet potato acylated anthocyanins: equilibrium network and photophysical properties. Food Chem 288:386–394
Park YJ et al (2016) Composition of volatile compounds and in vitro antimicrobial activity of nine Mentha spp. SpringerPlus 5(1):1628
Parker JK (2015) 1—Introduction to aroma compounds in foods. In: Parker JK, Elmore JS, Methven L (eds) Flavour development, analysis and perception in food and beverages. Woodhead, pp 3–30
Pei K et al (2016) p-Coumaric acid and its conjugates: dietary sources, pharmacokinetic properties and biological activities. J Sci Food Agric 96(9):2952–2962
Peluso I, Palmery M (2015) Flavonoids at the pharma-nutrition interface: is a therapeutic index in demand? Biomed Pharmacother 71:102–107
Pina F, Oliveira J, de Freitas V (2015) Anthocyanins and derivatives are more than flavylium cations. Tetrahedron 71(20):14
Pizzarello S (2015) Nonprotein amino acids. In: Gargaud M et al (eds) Encyclopedia of astrobiology. Springer, Berlin, pp 1697–1702
Poeckel D, Werz O (2006) Boswellic acids: biological actions and molecular targets. Curr Med Chem 13(28):3359–3369
Poeckel D et al (2005) Induction of central signalling pathways and select functional effects in human platelets by beta-boswellic acid. Br J Pharmacol 146(4):514–524
Pokorny J (1987) Major factors affecting the antioxidant of lipids. In: Chand H (ed) Autoxidation of unsaturated lipids. Academic, London, pp 141–206
Polturak G, Osbourn A (2021) The emerging role of biosynthetic gene clusters in plant defense and plant interactions. PLoS Pathog 17(7):e1009698
Porres-martinez M, Accame MEC, Gómez-Serranillos M (2013) Pharmacological activity of Salvia lavandulifolia and chemical components of its essential oil. A review. Lazaroa 34:237–254
Qing Z-X et al (2017) Isoquinoline alkaloids and their antiviral, antibacterial, and antifungal activities and structure-activity relationship. Curr Org Chem 21(18):1920–1934
Rashmi HB, Negi PS (2020) Phenolic acids from vegetables: a review on processing stability and health benefits. Food Res Int 136:109298
Rasul A et al (2013) Induction of apoptosis by costunolide in bladder cancer cells is mediated through ROS generation and mitochondrial dysfunction. Molecules 18(2):1418–1433
Reynolds WF, Enriquez RG (2017) Chapter 7—Terpenes: mono-, sesqui-, and higher terpenes. In: Modern NMR approaches to the structure elucidation of natural products: Volume 2: Data acquisition and applications to compound classes. The Royal Society of Chemistry, pp 251–274
Ribas de Pouplana L (2014) Not an inside job: non-coded amino acids compromise the genetic code. EMBO J 33(15):1619–1620
Rice-Evans C, Miller N, Paganga G (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20(7):933–956
Richelle M et al (2004) Both free and esterified plant sterols reduce cholesterol absorption and the bioavailability of beta-carotene and alpha-tocopherol in normocholesterolemic humans. Am J Clin Nutr 80(1):171–177
Ried K (2020) Garlic lowers blood pressure in hypertensive subjects, improves arterial stiffness and gut microbiota: a review and meta-analysis. Exp Ther Med 19(2):1472–1478
Romanos-Nanclares A et al (2020) Phenolic acid subclasses, individual compounds, and breast cancer risk in a mediterranean cohort: the SUN Project. J Acad Nutr Diet 120(6):1002–1015.e5
Saldanha SN, Tollefsbol TO (2012) The role of nutraceuticals in chemoprevention and chemotherapy and their clinical outcomes. J Oncol 2012:192464
Santana-Gálvez J, Cisneros-Zevallos L, Jacobo-Velázquez D (2017) Chlorogenic acid: recent advances on its dual role as a food additive and a nutraceutical against metabolic syndrome. Molecules 22:358
Seeram NP et al (2006) Blackberry, black raspberry, blueberry, cranberry, red raspberry, and strawberry extracts inhibit growth and stimulate apoptosis of human cancer cells in vitro. J Agric Food Chem 54:9329–9339
Shahbazi Y (2015) Chemical composition and in vitro antibacterial activity of Mentha spicata essential oil against common food-borne pathogenic bacteria. J Pathog 2015:916305
Shao Y et al (2014) Phenolic acids, anthocyanins, and antioxidant capacity in rice (Oryza sativa L.) grains at four stages of development after flowering. Food Chem 143:90–96
Sharifi-Rad J et al (2017) Biological activities of essential oils: from plant chemoecology to traditional healing systems. Molecules 22(1):70
Silva F et al (2007) Anthocyanin pigments in strawberry. LWT Food Sci Technol 40(2):374–382
Singh SK (2018) Explorations of plant’s chemodiversity: role of nitrogen-containing secondary metabolites in plant defense. In: Singh A, Singh IK (eds) Molecular aspects of plant-pathogen interaction. Springer, Singapore, pp 309–332
Singh B, Sharma RA (2015) Plant terpenes: defense responses, phylogenetic analysis, regulation and clinical applications. 3 Biotech 5(2):129–151
Siquet C et al (2006) Antioxidant profile of dihydroxy- and trihydroxyphenolic acids-A structure–activity relationship study. Free Radic Res 40(4):433–442
Sobral MV et al (2014) Antitumor activity of monoterpenes found in essential oils. ScientificWorldJournal 2014:953451
Sønderby IE, Geu-Flores F, Halkier BA (2010) Biosynthesis of glucosinolates—gene discovery and beyond. Trends Plant Sci 15(5):283–290
Song Y et al (2015) Sequential combination of flavopiridol with Taxol synergistically suppresses human ovarian carcinoma growth. Arch Gynecol Obstet 291(1):143–150
Sozer O et al (2010) Involvement of carotenoids in the synthesis and assembly of protein subunits of photosynthetic reaction centers of Synechocystis sp. PCC 6803. Plant Cell Physiol 51(5):823–835
Stintzing FC et al (2002) Color and antioxidant properties of cyanidin-based anthocyanin pigments. J Agric Food Chem 50:6172–6181
Subhan F et al (2010) Terpenoid content of Valeriana wallichii extracts and antidepressant-like response profiles. Phytother Res 24(5):686–691
Subramanian MS et al (2020) Prevailing knowledge on the bioavailability and biological activities of sulphur compounds from alliums: a potential drug candidate. Molecules 25(18):4111
Sun NK et al (2018a) TLR4 and NFκB signaling is critical for taxol resistance in ovarian carcinoma cells. J Cell Physiol 233(3):2489–2501
Sun Z et al (2018b) Biosynthesis and regulation of cyanogenic glycoside production in forage plants. Appl Microbiol Biotechnol 102(1):9–16
Tadeusz A (2015) Alkaloids: chemistry, biology, ecology, and applications, vol 13. Elsevier, Amsterdam. 978-0444594334
Takaishi M et al (2012) 1,8-cineole, a TRPM8 agonist, is a novel natural antagonist of human TRPA1. Mol Pain 8:86
Teixeira J et al (2013) Hydroxycinnamic acid antioxidants: an electrochemical overview. Biomed Res Int 2013:251754
Tena N, Martín J, Asuero A (2020) State of the art of anthocyanins: antioxidant activity, sources, bioavailability, and therapeutic effect in human health. Antioxidants 9:45
Thawabteh A et al (2019) The biological activity of natural alkaloids against herbivores, cancerous cells and pathogens. Toxins 11(11):656
Thimmappa R et al (2014) Triterpene biosynthesis in plants. Annu Rev Plant Biol 65(1):225–257
Tian Z et al (2021) Dose-dependent effects of anthocyanin supplementation on platelet function in subjects with dyslipidemia: a randomized clinical trial. EBioMedicine 70:103533
Tuladhar P, Sasidharan S, Saudagar P (2021) Role of phenols and polyphenols in plant defense response to biotic and abiotic stresses. In: Biocontrol agents and secondary metabolites: applications and immunization for plant growth and protection. Woodhead, pp 419–441
Vankar P, Srivastava J (2010) Evaluation of anthocyanin content in red and blue flowers. Int J Food Eng 6(4)
Vetter J (2000) Plant cyanogenic glycosides. Toxicon 38(1):11–36
Vicente MR, Plasencia J (2011) Salicylic acid beyond defence: its role in plant growth and development. J Exp Bot 62(10):3321–3338
Vuolo MM, Lima VS, Maróstica-Jr MR (2019) Phenolic compounds: structure, classification, and antioxidant power. In: Bioactive compounds: health benefits and potential applications. Woodhead, pp 33–50
Wagner CS et al (2017) Antibacterial activity of medicinal plants from The Physicians of Myddvai, a 14th century Welsh medical manuscript. J Ethnopharmacol 203:171–181
Wang X et al (2015) Inhibitory effects of JEUD-38, a new sesquiterpene lactone from Inula japonica Thunb, on LPS-induced iNOS expression in RAW264.7 cells. Inflammation 38(3):941–948
Wang T-H et al (2016) Evaluation of the antibacterial potential of liquid and vapor phase phenolic essential oil compounds against oral microorganisms. PLoS One 11(9):e0163147
Wang S, Meng X, Dong Y (2017) Ursolic acid nanoparticles inhibit cervical cancer growth in vitro and in vivo via apoptosis induction. Int J Oncol 50(4):1330–1340
Wang C et al (2018) Microbial platform for terpenoid production: Escherichia coli and yeast. Front Microbiol 9
Wang P et al (2019) Synthesizing ginsenoside Rh2 in Saccharomyces cerevisiae cell factory at high-efficiency. Cell Discov 5(1):5
Wang L et al (2021) Medical cannabis or cannabinoids for chronic non-cancer and cancer related pain: a systematic review and meta-analysis of randomised clinical trials. BMJ 374:n1034
Wani MC et al (1971) Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 93(9):2325–2327
Williamson G (2017) The role of polyphenols in modern nutrition. Nutr Bull 42(3):226–235
Wu S et al (2018) Structure–affinity relationship of the interaction between phenolic acids and their derivatives and β-lactoglobulin and effect on antioxidant activity. Food Chem 245:613–619
Wu W et al (2021) Simultaneous process optimization of ultrasound-assisted extraction of polyphenols and ellagic acid from pomegranate (Punica granatum L.) flowers and its biological activities. Ultrason Sonochem 80:105833
Xu YF et al (2017) In vitro and in vivo antibacterial activities of patchouli alcohol, a naturally occurring tricyclic sesquiterpene, against Helicobacter pylori infection. Antimicrob Agents Chemother 61(6):e00122-17
Xu C et al (2020) Artemisinins as anticancer drugs: novel therapeutic approaches, molecular mechanisms, and clinical trials. Front Pharmacol 11:529881
Yamane H et al (2010) Chemical defence and toxins of plants
Yang YI et al (2011) Costunolide induces apoptosis in platinum-resistant human ovarian cancer cells by generating reactive oxygen species. Gynecol Oncol 123(3):588–596
Yee DA et al (2019) Engineered mitochondrial production of monoterpenes in Saccharomyces cerevisiae. Metab Eng 55:76–84
Yulvianti M, Zidorn C (2021) Chemical diversity of plant cyanogenic glycosides: an overview of reported natural products. Molecules (Basel, Switzerland) 26(3):719
Zamora-Ros R et al (2013) Dietary intakes and food sources of phenolic acids in the European Prospective Investigation into Cancer and Nutrition (EPIC) study. Br J Nutr 110(8):1500–1511
Zhang L et al (2020) Effect of andrographolide and its analogs on bacterial infection: a review. Pharmacology 105(3–4):123–134
Zhao Z, Moghadasian M (2008) Chemistry, natural sources, dietary intake and pharmacokinetic properties of ferulic acid: a review. Food Chem 109(4):691–702
Zhao CL et al (2014) Structure-activity relationships of anthocyanidin glycosylation. Mol Divers 18(3):687–700
Zor M, Aydur E, Dmochowski RR (2015) Flavoxate in urogynecology: an old drug revisited. Int Urogynecol J 26(7):959–966
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2023 The Author(s), under exclusive license to Springer Nature Switzerland AG
About this chapter
Cite this chapter
Oliveira, H., Pérez-Gregorio, R., Fernandes, I., Soares, S., Freitas, V., Dias, R. (2023). New Trends from Plant Secondary Metabolism in the Pharmaceutical Industry. In: Carocho, M., Heleno, S.A., Barros, L. (eds) Natural Secondary Metabolites. Springer, Cham. https://doi.org/10.1007/978-3-031-18587-8_25
Download citation
DOI: https://doi.org/10.1007/978-3-031-18587-8_25
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-031-18586-1
Online ISBN: 978-3-031-18587-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)