Abstract
Alkaloids are a type of secondary metabolites that can be found in different parts of plants. This group of compounds is diverse and can be divided into nine subgroups: pyridine, tropane, isoquinoline, phenanthrene, phenylethylamine, indole, purine, imidazole, and terpenoids. Most of these compounds are recognized for their anti-inflammatory, antitumor, antibacterial, antifungal, and antiviral activities, among others. Although more than 27,000 alkaloids have been described up to date, the search for novel compounds with promising therapeutic properties is a hot topic among researchers worldwide. In this line, the production of the currently marketed plant alkaloids including extraction methods, isolation, and purification is reviewed in this chapter. In addition, a deep description of different groups of alkaloids in terms of their chemical structure, plant source, and uses is also presented. Recent advances in the therapeutic potential and biological activities of this vast group of phytochemicals are also included.
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Abbreviations
- AE:
-
Acid extraction
- DE:
-
Decoction
- DES:
-
Eutectic solvents
- HP:
-
Hot water under pressure
- HPPE:
-
High-pressure propane extraction
- MA:
-
Maceration
- MAE:
-
Microwave-assisted extraction
- ME:
-
Methylation
- PHWE:
-
Pressurized hot water extraction
- SFE:
-
Supercritical fluid extraction
- SO:
-
Soxhlet
- UAE:
-
Ultrasound-assisted extraction
- WE:
-
Water extraction
- GC-MS:
-
Gas chromatography coupled to mass spectrometry
- HPLC:
-
High-performance liquid chromatography
- HPLC-Q-TOF-MS:
-
High-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry
- HPLC–UV–ESI MS/MS:
-
HPLC with UV detection coupled with electrospray ionization MS/MS
- HPTLC:
-
High-performance thin-layer chromatographic
- HSCCC:
-
High-speed counter-current chromatography
- NMR:
-
Nuclear magnetic resonance
- TLC:
-
Thin-layer chromatography
- UHPLC–Q-TOF-MS:
-
Ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry
- IA:
-
Isoquinoline alkaloids
- InA:
-
Indole alkaloids
- IzA:
-
Imidazole alkaloids
- PA:
-
Pyridine alkaloids
- PeA:
-
Phenylethylamine alkaloids
- PhA:
-
Phenanthrene alkaloids
- PuA:
-
Purine alkaloids
- TA:
-
Tropane alkaloids
- TeA:
-
Terpenoid alkaloids
- FDA:
-
Food and Drug Administration
- HR:
-
Hairy root culture
- MEP:
-
Methyl-erythritol phosphate
- Nd:
-
Not determined
References
Adamse P, Van Egmond HP (2010) Method development and analysis of mycotoxins and phycotoxins in food Tropane alkaloids in food [Internet]. [cited 2022 Jan 17]. www.rikilt.wur.nl
Afewerki S, Wang JX, Liao WW, Córdova A (2019) The chemical synthesis and applications of tropane alkaloids. In: Alkaloids: chemistry and biology. Academic Press, New York, pp 151–233
Ahammed GJ, Zhou YH, Xia XJ, Mao WH, Shi K, Yu JQ (2013) Brassinosteroid regulates secondary metabolism in tomato towards enhanced tolerance to phenanthrene. Biol Plant 57(1):154–158
Ahmad S, Garg M, Tamboli ET, Abdin MZ, Ansari SH (2013) In vitro production of alkaloids: factors, approaches, challenges and prospects. Pharmacogn Rev 7(13):27–33. https://doi.org/10.4103/0973-7847.112837
Ahmad A, Ahmad W, Zeenat F, Sajid M (2018) Therapeutic, phytochemistry and pharmacology of Tamarindus indica: a review. Int J Unani Integr Med 2(2):14–19
Anaya AL, Cruz-Ortega R, Waller GR (2006) Metabolism and ecology of purine alkaloids. Front Biosci 11:2354–2370
Aniszewski T (2015) Alkaloid chemistry. In: Alkaloids. Elsevier, New York, pp 99–193
Appley MG, Chambers MI, Musah RA (2021) Quantification of hordenine in a complex plant matrix by direct analysis in real time–high-resolution mass spectrometry: application to the “plant of concern” Sceletium tortuosum. Drug Test Anal [Internet]. [cited 2022 Feb 10]. https://onlinelibrary.wiley.com/doi/full/10.1002/dta.3193
Ashihara H, Crozier A (1999) Biosynthesis and metabolism of caffeine and related purine alkaloids in plants. Adv Bot Res. 30:117–205
Ashihara H, Sano H, Crozier A (2008) Caffeine and related purine alkaloids: biosynthesis, catabolism, function and genetic engineering. Phytochemistry 69:841–856
Ashihara H, Ludwig IA, Crozier A (2020) Occurrence and biosynthesis of pyridine alkaloids. In: Plant nucleotide metabolism - biosynthesis, degradation, and alkaloid formation [Internet]. Wiley [cited 2022 Jan 18]. pp 329–349. https://onlinelibrary.wiley.com/doi/full/10.1002/9781119476139.ch20
Awuchi CG (2019) The biochemistry, toxicology, and uses of the pharmacologically active phytochemicals: alkaloids, terpenes, polyphenols, and glycosides. J Food Pharm Sci 7(1):2
Balick MJ, Rivier L, Plowman T (1982) The effects of field preservation on alkaloid content of fresh coca leaves (Erythroxylum spp.). J Ethnopharmacol 6(3):287–291
Barnes PJ (2006) Drugs for asthma. Br J Pharmacol 147:297–303
Bedikian AY, Plager C, Papadopoulos N, Eton O, Ellerhorst J, Smith T (2004) Phase II evaluation of paclitaxel by short intravenous infusion in metastatic melanoma. Melanoma Res 14(1):63–66
Belwal T, Pandey A, Bhatt ID, Rawal RS (2020 Jan 22) Optimized microwave assisted extraction (MAE) of alkaloids and polyphenols from Berberis roots using multiple-component analysis. Sci Rep [Internet]. [cited 2022 Jan 19];10(1):1–10. https://www.nature.com/articles/s41598-020-57585-8
Bernardo J, Ferreres F, Gil-Izquierdo Á, Videira RA, Valentão P, Veiga F, et al (2018 Jan 30) In vitro multimodal-effect of Trichilia catigua A. Juss. (Meliaceae) bark aqueous extract in CNS targets. J Ethnopharmacol [Internet]. [cited 2022 Jan 19];211:247–55. https://pubmed.ncbi.nlm.nih.gov/28970152/
Bhandari M, Bhandari A, Bhandari A (2011) Recent updates on codeine. Pharm Methods 2(1):3–8. https://doi.org/10.4103/2229-4708.81082
Bhatia S (2015 Jan) History and scope of plant biotechnology. Mod Appl Plant Biotechnol Pharm Sci 1:1–30
Borquaye LS, Gasu EN, Ampomah GB, Kyei LK, Amarh MA, Mensah CN et al (2020) Alkaloids from Cryptolepis sanguinolenta as potential inhibitors of SARS-CoV-2 viral proteins: an in silico study. Biomed Res Int 2020:5324560
Bouffet E, Jakacki R, Goldman S, Hargrave D, Hawkins C, Shroff M et al (2012) Phase II study of weekly vinblastine in recurrent or refractory pediatric low-grade glioma. J Clin Oncol 30(12):1358–1363
Bourdat-Deschamps M, Herrenknecht C, Akendengue B, Laurens A, Hocquemiller R (2004) Separation of protoberberine quaternary alkaloids from a crude extract of Enantia chlorantha by centrifugal partition chromatography. J Chromatogr A. 1041(1–2):143–152
Bourebaba L, Sullini G, Mendiola JA, Bourebaba Y, Deghima A, Oukil N et al (2016) In-vivo edema inhibition of Hyoscyamus albus antioxidant extracts rich in calystegines. Ind Crops Prod. 89:316–322
Brown T (2008) Deisign thinking. Harv Bus Rev 86(6):84–92
Browning DJ (2014) Hydroxychloroquine and chloroquine retinopathy. Springer, New York, pp 1–291
Brugnerotto P, Seraglio SKT, Schulz M, Gonzaga LV, Fett R, Costa ACO (2021) Pyrrolizidine alkaloids and beehive products: a review. Food Chem 342:128384
Bufo SA, Karaman R (2019) Herbivores, cancerous cells and pathogens. Toxins (Basel) 11(656):1–28
Bulduk I, Gezer B, Cengiz M (2015) Optimization of ultrasound-assisted extraction of morphine from capsules of Papaver somniferum by response surface methodology. Int J Anal Chem 2015:796349. https://doi.org/10.1155/2015/796349
Cassani L, Gomez-Zavaglia A (2022) Sustainable food systems in fruits and vegetables food supply chains. Front Nutr 9
Chan TYK (2009) Aconite poisoning. Clinical Toxicol 47:279–285
Chan ZY, Krishnan P, Modaresi SM, Hii LW, Mai CW, Lim WM, et al (2021 Aug 27) Monomeric, dimeric, and trimeric tropane alkaloids from pellacalyx saccardianus. J Nat Prod [Internet]. [cited 2022 Feb 23];84(8):2272–2281. https://pubs.acs.org/doi/abs/10.1021/acs.jnatprod.1c00374
Cheang TM (2018) Biological screening for anti-influenza a virus agents. University of Malaya, Kuala Lumpur
Chen X, Shao S, Yang R, Gu M, Wang P, Zhao F et al (2021) Identification of co-expressed genes related to theacrine synthesis in tea flowers at different developmental stages. Int J Mol Sci 22(24):13394
Cheng W, Lu J, Wang B, Sun L, Zhu B, Zhou F et al (2021) Inhibition of inflammation-induced injury and cell migration by coelonin and militarine in PM2.5-exposed human lung alveolar epithelial A549 cells. Eur J Pharmacol. 896:173931
Cherney EC, Baran PS (2011) Terpenoid-alkaloids: their biosynthetic twist of fate and total synthesis. Israel J Chem 51:391–405
Chia A, Lu QS, Tan D (2016) Five-year clinical trial on atropine for the treatment of myopia 2 myopia control with atropine 0.01% eyedrops. Ophthalmology 123(2):391–399
Chiocchio I, Mandrone M, Tomasi P, Marincich L, Poli F (2021) Plant secondary metabolites: an opportunity for circular economy. Molecules 26
Cinelli MA, Jones AD (2021) Alkaloids of the genus datura: review of a rich resource for natural product discovery. Molecules 26(9):2629
Csupor D, Wenzig EM, Zupkó I, Wölkart K, Hohmann J, Bauer R (2009) Qualitative and quantitative analysis of aconitine-type and lipo-alkaloids of Aconitum carmichaelii roots. J Chromatogr A 1216(11):2079–2086
Cui WQ, Wang ST, Pan D, Chang B, Sang LX (2020) Caffeine and its main targets of colorectal cancer. World J Gastrointest Oncol 12:149–172
da Silva DM, Martins JLR, de Oliveira DR, Florentino IF, da Silva DPB, dos Santos FCA et al (2018) Effect of allantoin on experimentally induced gastric ulcers: Pathways of gastroprotection. Eur J Pharmacol 821:68–78
da Silveira A-CT (2020) Bioactive compounds and health benefits of Pereskioideae and Cactoideae: a review. Food Chem 327
Daly JW (2003 Jun 1) Alkaloids. Nature’s curse or blessing by Manfred Hesse. Verlag Helvetica Chimica Acta, Zürich, Switzerland, and Wiley-VCH Weinheim, Germany. 2002. xii + 413 pp. 16 × 18 cm. $135. ISBN 3-906390-24-1. J Nat Prod [Internet]. [cited 2022 Jan 20];66(6):901–902. https://pubs.acs.org/doi/full/10.1021/np030705p
Das S, Krishi Viswavidyalaya C, Sharangi AB (2017) Madagascar periwinkle (Catharanthus roseus L.): Diverse medicinal and therapeutic benefits to humankind. J Pharmacogn Phytochem 6(5):1695–1701
Das A, Sarkar S, Bhattacharyya S, Gantait S (2020) Biotechnological advancements in Catharanthus roseus (L.) G. Don. Appl Microbiol Biotechnol 104:4811–4835
Davies SG, Roberts PM, Stephenson PT, Storr HR, Thomson JE (2009) A practical and scaleable total synthesis of the jaborandi alkaloid (+)-pilocarpine. Tetrahedron 65(39):8283–8296
Debnath B, Singh WS, Das M, Goswami S, Singh MK, Maiti D et al (2018) Role of plant alkaloids on human health: a review of biological activities. In: Materials today chemistry, vol 9. Elsevier, New York, pp 56–72
Demetri GD, Von Mehren M, Jones RL, Hensley ML, Schuetze SM, Staddon A et al (2016) Efficacy and safety of trabectedin or dacarbazine for metastatic liposarcoma or leiomyosarcoma after failure of conventional chemotherapy: results of a phase III randomized multicenter clinical trial. J Clin Oncol 34(8):786–793
Dey P, Kundu A, Kumar A, Gupta M, Lee BM, Bhakta T et al (2020) Analysis of alkaloids (indole alkaloids, isoquinoline alkaloids, tropane alkaloids). In: Recent advances in natural products analysis. Elsevier, New York, pp 505–567
Dittbrenner A, Mock HP, Börner A, Lohwasser U (2009) Variability of alkaloid content in Papaver somniferum L. J Appl Bot Food Qual 82(2):103–107
Dräger B (1995 Jan 1) Identification and quantification of calystegines, polyhydroxyl nortropane alkaloids. Phytochem Anal [Internet]. [cited 2022 Jan 14];6(1):31–37. https://onlinelibrary.wiley.com/doi/full/10.1002/pca.2800060105
Dutta D, Ramanna C, Kamath VV (2017) Estimation of arecoline content of various forms of areca nut preparations by high-pressure thin-layer chromatography. J Adv Clin Res Insights. 4(2):31–37
Dziekan JM, Yu H, Chen D, Dai L, Wirjanata G, Larsson A et al (2019) Identifying purine nucleoside phosphorylase as the target of quinine using cellular thermal shift assay. Sci Transl Med 11(473)
Edagha IA, Davies KG, Akpan BC, Mbadugha CC, Udoiso WU (2014 Mar 15 ) Ethanolic extract of Emilia sonchifolia leaves possess erythropoietic and hepatoprotective effect in mice infected with plasmodium berghei berghei. Open Access Maced J Med Sci [Internet]. [cited 2022 Jan 20];2(1):11–17. https://oamjms.eu/index.php/mjms/article/view/2
Eini H, Frishman V, Yulzari R, Kachko L, Lewis EC, Chaimovitz C et al (2015) Caffeine promotes anti-tumor immune response during tumor initiation: involvement of the adenosine A2A receptor. Biochem Pharmacol. 98(1):110–118
El-Sayed RM, Abo El Gheit RE, Badawi GA (2021) Vincamine protects against cisplatin induced nephrotoxicity via activation of Nrf2/HO-1 and hindering TLR4/ IFN-γ/CD44 cells inflammatory cascade. Life Sci 272:119224
Fan X, Kong D, He S, Chen J, Jiang Y, Ma Z et al (2021) Phenanthrene derivatives from asarum heterotropoides showed excellent antibacterial activity against phytopathogenic bacteria. J Agric Food Chem 69(48):14520–14529
Fang YS, Yang MH, Wang JP, Fu H, Cai L, Ding ZT (2021) Four new phenanthrene derivatives from Bulbophyllum retusiusculum. Fitoterapia. 1(152):104910
Fatima S, Mujib A, Tonk D (2015 May 1) NaCl amendment improves vinblastine and vincristine synthesis in Catharanthus roseus: a case of stress signalling as evidenced by antioxidant enzymes activities. Plant Cell Tissue Organ Cult [Internet]. [cited 2022 Feb 10];121(2):445–458. https://link.springer.com/article/10.1007/s11240-015-0715-5
Fernandez-Gomez B, Lezama A, Amigo-Benavent M, Ullate M, Herrero M, Martín MÁ et al (2016) Insights on the health benefits of the bioactive compounds of coffee silverskin extract. J Funct Foods 25:197–207
Fischer M, Jefferies TM (1996) Optimization of nicotine extraction from tobacco using supercritical fluid technology with dynamic extraction modeling. J Agric Food Chem [Internet]. [cited 2022 Jan 18];44(5):1258–1264. https://pubs.acs.org/sharingguidelines
Florea S, Panaccione DG, Schardl CL (2017) Ergot alkaloids of the family clavicipitaceae. Phytopathology 107:504–518
Furusaki S, Takeda T (2019) Bioreactors for plant cell culture. In: Comprehensive biotechnology. Elsevier, Pergamon, pp 519–530
Gadzikowska M, Grynkiewicz G (2002) Tropane alkaloids in pharmaceutical and phytochemical analysis. Acta Pol Pharm Drug Res 59(2):149–160
Gantait S, Mukherjee E (2021) Hairy root culture technology: applications, constraints and prospect [Internet]. vol 105, Applied microbiology and biotechnology. Springer Science and Business Media Deutschland GmbH [cited 2022 Jan 20]. pp 35–53. https://link.springer.com/article/10.1007/s00253-020-11017-9
Gantet P, Memelink J (2002) Transcription factors: tools to engineer the production of pharmacologically active plant metabolites [Internet]. vol 23, Trends in pharmacological sciences [cited 2022 Jan 19]. pp 563–569. https://pubmed.ncbi.nlm.nih.gov/12457774/
Garcia-Oliveira P, Otero P, Pereira AG, Chamorro F, Carpena M, Echave J, et al (2021 Feb 14) Status and challenges of plant-anticancer compounds in cancer treatment. Pharmaceuticals [Internet]. [cited 2021 Mar 1];14(2):157. https://www.mdpi.com/1424-8247/14/2/157
Garg S, Roy A (2020) In silico analysis of selected alkaloids against main protease (Mpro) of SARS-CoV-2. Chem Biol Interact 332(September):109309
Ghaffar N, Lee LS, Choi YJ, Perre C, Khan B (2021) Efficient heated ultrasound assisted extraction and clean-up method for quantifying paclitaxel concentrations in Taxus wallichiana. Int J Environ Anal Chem 101(4):549–560
Gibbons S, Arunotayanun W (2013) Natural product (fungal and herbal) novel psychoactive substances. In: Novel psychoactive substances: classification, pharmacology and toxicology. Elsevier, New York, pp 345–362
Gonçalves Paterson Fox E, Russ Solis D, Delazari dos Santos L, dos Santos A, Pinto JR, da Silva R, Menegasso A, Silva CMC et al (2013) A simple, rapid method for the extraction of whole fire ant venom (Insecta: Formicidae: Solenopsis). Toxicon 65:5–8
Gradishar WJ (2012) Taxanes for the treatment of metastatic breast cancer. Breast Cancer 6:159–171
Gradishar WJ, Tjulandin S, Davidson N, Shaw H, Desai N, Bhar P et al (2005) Phase III trial of nanoparticle albumin-bound paclitaxel compared with polyethylated castor oil-based paclitaxel in women with breast cancer. J Clin Oncol 23(31):7794–7803
Grebenstein PE, Erickson P, Grace M, Kotz CM (2022) Anatabine, nornicotine, and anabasine reduce weight gain and body fat through decreases in food intake and increases in physical activity. J Clin Med 11(3):481
Griffiths MR, Strobel BW, Hama JR, Cedergreen N (2021) Toxicity and risk of plant-produced alkaloids to Daphnia magna. Environ Sci Eur 33(1)
Grycová L, Dostál J, Marek R (2007) Quaternary protoberberine alkaloids. In: Phytochemistry, vol 68. Elsevier, Pergamon, pp 150–175
Guo ZG, Liu Y, Gong MZ, Chen W, Li WY (2013 Jan 29) Regulation of vinblastine biosynthesis in cell suspension cultures of Catharanthus roseus. Plant Cell Tissue Organ Cult [Internet]. [cited 2022 Feb 10];112(1):43–54. https://link.springer.com/article/10.1007/s11240-012-0213-y
Gupta P (2015) Synthesis of bioactive imidazoles: a review. Chem Sci J 6(2)
Gutierrez-Valdes N, Häkkinen ST, Lemasson C, Guillet M, Oksman-Caldentey KM, Ritala A et al (2020) Hairy root cultures—a versatile tool with multiple applications. Front Plant Sci 11:33
Güven KC, Percot A, Sezik E (2010) Alkaloids in marine algae. Mar Drugs 8:269–284
Häkkinen ST, Oksman-Caldentey KM (2018) Progress and prospects of hairy root research. In: Hairy roots: an effective tool of plant biotechnology [Internet]. Springer, Singapore [cited 2022 Jan 20]. pp 3–19. https://link.springer.com/chapter/10.1007/978-981-13-2562-5_1
Haller CA, Jacob P, Benowitz NL (2004) Enhanced stimulant and metabolic effects of combined ephedrine and caffeine. Clin Pharmacol Ther 75(4):259–273
Han J, Jiang L, Zhang L, Quinn RJ, Liu X, Feng Y (2021) Peculiarities of meroterpenoids and their bioproduction. Appl Microbiol Biotechnol 105:3987–4003
He K, Hu Y, Ma H, Zou Z, Xiao Y, Yang Y et al (2016) Rhizoma coptidis alkaloids alleviate hyperlipidemia in B6 mice by modulating gut microbiota and bile acid pathways. Biochim Biophys Acta Mol Basis Dis 1862(9):1696–1709
Heubach JF, Schüle A (1998) Cardiac effects of lappaconitine and N-deacetyllappaconitine, two diterpenoid alkaloids from plants of the Aconitum and Delphinium species. Planta Med 64(1):22–26
Hien DFDS, Paré PSL, Cooper A, Koama BK, Guissou E, Yaméogo KB, et al (2021 Dec 1) Contrasting effects of the alkaloid ricinine on the capacity of Anopheles gambiae and Anopheles coluzzii to transmit Plasmodium falciparum. Parasites Vectors [Internet]. [cited 2022 Jan 18];14(1):1–11. https://parasitesandvectors.biomedcentral.com/articles/10.1186/s13071-021-04992-z
Huang P, Xia L, Liu W, Jiang R, Liu X, Tang Q, et al (2018 Aug 10) Hairy root induction and benzylisoquinoline alkaloid production in Macleaya cordata. Sci Rep [Internet]. [cited 2022 Jan 20];8(1):1–9. https://www.nature.com/articles/s41598-018-30560-0
Huang JP, Wang YJ, Tian T, Wang L, Yan Y, Huang SX (2021) Tropane alkaloid biosynthesis: a centennial review [Internet]. vol 38, Natural product reports. The Royal Society of Chemistry [cited 2022 Jan 17]. pp 1634–1658. https://pubs.rsc.org/en/content/articlehtml/2021/np/d0np00076k
Hughes EH, Shanks JV (2002) Metabolic engineering of plants for alkaloid production. Metab Eng 4(1):41–48
Hyuga S, Hyuga M, Oshima N, Maruyama T, Kamakura H, Yamashita T, et al (2016) Ephedrine alkaloids-free Ephedra Herb extract: a safer alternative to ephedra with comparable analgesic, anticancer, and anti-influenza activities. J Nat Med [Internet]. [cited 2022 Feb 10];70(3):571–583. https://link.springer.com/article/10.1007/s11418-016-0979-z
Jhuo CF, Hsu YY, Chen WY, Tzen JTC (2021) Attenuation of tumor development in mammary carcinoma rats by theacrine, an antagonist of adenosine 2a receptor. Molecules 26(24):1–12
Jiang F, Li M, Wang H, Ding B, Zhang C, Ding Z et al (2019) Coelonin, an anti-inflammation active component of Bletilla striata and its potential mechanism. Int J Mol Sci 20(18)
Jin SS, Guo Q, Xu J, Yu P, Liu JH, Tang YQ (2015) Antiarrhythmic ionic mechanism of Guanfu base A-Selective inhibition of late sodium current in isolated ventricular myocytes from guinea pigs. Chin J Nat Med 13(5):361–367
Jones NM, Bernardo-Gil MG, Lourenço MG (2001 Mar 1) Comparison of methods for extraction of tobacco alkaloids. J AOAC Int [Internet]. [cited 2022 Jan 20];84(2):309–316. https://academic.oup.com/jaoac/article/84/2/309/5656442
Khan AY, Suresh Kumar G (2015) Natural isoquinoline alkaloids: binding aspects to functional proteins, serum albumins, hemoglobin, and lysozyme. Biophys Rev 7(4):407–420. https://doi.org/10.1007/s12551-015-0183-5
Kim EH, Min HY, Chung HJ, Song J, Park HJ, Kim S et al (2012) Anti-proliferative activity and suppression of P-glycoprotein by (-)-antofine, a natural phenanthroindolizidine alkaloid, in paclitaxel-resistant human lung cancer cells. Food Chem Toxicol 50(3–4):1060–1065
Klein-Júnior LC, Vander Heyden Y, Henriques AT (2016) Enlarging the bottleneck in the analysis of alkaloids: a review on sample preparation in herbal matrices. Trends Anal Chem 80:66–82
Kleinmeier D, Pettengill E, Redan BW (2021) Commentary: opium alkaloids in harvested and thermally processed poppy seeds. Front Chem 8:737
Kloc M, Ghobrial RM, Kubiak JZ (2020) How nicotine can inhibit cytokine storm in the lungs and prevent or lessen the severity of COVID-19 infection? Immunol Lett 224:28–29
Koetz M, Santos TG, Rayane M, Henriques AT (2017) Quantification of atropine in leaves of Atropa belladonna: development and validation of method by high-perfomance liquid chromatography (Hplc). Drug Anal Res 1(1):44–49
Kohnen-Johannsen KL, Kayser O (2019) Tropane alkaloids: chemistry, pharmacology, biosynthesis and production. Molecules 24(4):796. https://doi.org/10.3390/molecules24040796
Kopp T, Abdel-Tawab M, Mizaikoff B (2020) Extracting and analyzing pyrrolizidine alkaloids in medicinal plants: a review [Internet]. vol 12, Toxins. Multidisciplinary Digital Publishing Institute [cited 2022 Jan 20]. p 320. https://www.mdpi.com/2072-6651/12/5/320/htm
Kovács A, Vasas A, Hohmann J (2008) Natural phenanthrenes and their biological activity. Phytochemistry 69:1084–1110
Kuete V (2014) Health effects of alkaloids from African medicinal plants. In: Toxicological survey of African medicinal plants. Elsevier, New York, pp 611–633
Kukula-Koch WA, Widelski J (2017) Alkaloids. In: Pharmacognosy: fundamentals, applications and strategy. Academic Press, New York, pp 163–198
Kulma A, Szopa J (2007) Catecholamines are active compounds in plants. Plant Sci 172:433–440
Kumar S, Singh B, Singh R (2022) Catharanthus roseus (L.) G. Don: a review of its ethnobotany, phytochemistry, ethnopharmacology and toxicities. J Ethnopharmacol 284:114647
Kumari A, Singh RK (2019) Medicinal chemistry of indole derivatives: current to future therapeutic prospectives. In: In: Bioorganic chemistry, vol 89. Elsevier, New York, p 103021
Kurek J (2019) Introductory Chapter: Alkaloids - their importance in nature and for human life. In: Alkaloids - their importance in nature and human life [Internet]. IntechOpen [cited 2022 Jan 14]. https://www.intechopen.com/chapters/66742
Kwang KK, Quon MJ, Seung HH, Chung WJ, Jeong YA, Seo YH et al (2004) Additive beneficial effects of losartan combined with simvastatin in the treatment of hypercholesterolemic, hypertensive patients. Circulation 110(24):3687–3692
Langmead CJ, Watson J, Reavill C (2008) Muscarinic acetylcholine receptors as CNS drug targets [Internet]. vol 117, Pharmacology and therapeutics. Pharmacol Ther [cited 2022 Jan 14]. pp 232–243. https://pubmed.ncbi.nlm.nih.gov/18082893/
Lee YS, Kim WS, Kim KH, Yoon MJ, Cho HJ, Shen Y et al (2006) Berberine, a natural plant product, activates AMP-activated protein kinase with beneficial metabolic effects in diabetic and insulin-resistant states. Diabetes 55(8):2256–2264
Lee MY, Lee NH, Jung D, Lee JA, Seo CS, Lee H et al (2010) Protective effects of allantoin against ovalbumin (OVA)-induced lung inflammation in a murine model of asthma. Int Immunopharmacol 10(4):474–480
Leitão GG, Leal CM, Mendonça SC, Pereda-Miranda R (2021) Purification of alkaloids by countercurrent chromatography [Internet]. vol 31, Revista Brasileira de Farmacognosia. Springer [cited 2022 Feb 24]. pp 625–647. https://link.springer.com/article/10.1007/s43450-021-00163-4
Li Y, Zhang G, Pfeifer BA (2015) Current and emerging options for taxol production. Adv Biochem Eng Biotechnol 148:405–425
Li G, Wang X, Row KH (2017 Jun 25) Magnetic solid-phase extraction with Fe3O4/molecularly imprinted polymers modified by deep eutectic solvents and ionic liquids for the rapid purification of alkaloid isomers (Theobromine and Theophylline) from green tea. Molecules [Internet]. [cited 2022 Feb 10];22(7):1061. https://www.mdpi.com/1420-3049/22/7/1061/htm
Li S, Li Y, Smolke CD (2018) Strategies for microbial synthesis of high-value phytochemicals [Internet]. vol 10, Nature chemistry. Nature Publishing Group [cited 2022 Jan 19]. pp 395–404. https://www.nature.com/articles/s41557-018-0013-z
Lião LM (2003) Sesquiterpene pyridine alkaloids. In: Alkaloids: chemistry and biology, vol 60. Elsevier, New York, pp 287–343
Lichman BR (2021) The scaffold-forming steps of plant alkaloid biosynthesis [Internet]. vol 38, Natural product reports. Royal Society of Chemistry [cited 2022 Jan 19]. pp 103–29. https://pubs.rsc.org/en/content/articlehtml/2021/np/d0np00031k
Lin YS, Wu SS, Lin JK (2003 Feb 12 ) Determination of tea polyphenols and caffeine in tea flowers (Camellia sinensis) and their hydroxyl radical scavenging and nitric oxide suppressing effects. J Agric Food Chem [Internet]. [cited 2022 Feb 10];51(4):975–980. https://pubs.acs.org/doi/abs/10.1021/jf020870v
Lin Y, Wang F, Yang LJ, Chun Z, Bao JK, Zhang GL (2013) Anti-inflammatory phenanthrene derivatives from stems of Dendrobium denneanum. Phytochemistry 95:242–251
Lin SX, Curtis MA, Sperry J (2020) Pyridine alkaloids with activity in the central nervous system. Bioorganic Med Chem 28(24):115820
Long J, Song J, Zhong L, Liao Y, Liu L, Li X (2019) Palmatine: a review of its pharmacology, toxicity and pharmacokinetics. Biochimie 162:176–184
Lu Q, Li R, Yang Y, Zhang Y, Zhao Q, Li J (2022) Ingredients with anti-inflammatory effect from medicine food homology plants. Food Chem. 2021(368):130610
Lv SS, Fu Y, Chen J, Jiao Y, Chen SQ (2020) Six phenanthrenes from the roots of Cymbidium faberi Rolfe. and their biological activities. Nat Prod Res [Internet]. [cited 2022 Mar 2];1–12. https://www.tandfonline.com/doi/abs/10.1080/14786419.2020.1862836
Ma W, Zhang Y, Ding YY, Liu F, Li N (2016 Feb 1) Cytotoxic and anti-inflammatory activities of phenanthrenes from the medullae of Juncus effusus L. Arch Pharm Res [Internet]. [cited 2022 Mar 2];39(2):154–60. https://pubmed.ncbi.nlm.nih.gov/26584913/
Madani A, Mazouni N, Nedjhioui M (2021 Sep 29) Plants’ bioactive metabolites and extraction methods. In: Mazouni N (ed). [cited 2022 Jan 20];Chap. 3. https://www.intechopen.com/chapters/75759
Majumder M, Debnath S, Gajbhiye RL, Saikia R, Gogoi B, Samanta SK et al (2019) Ricinus communis L. fruit extract inhibits migration/invasion, induces apoptosis in breast cancer cells and arrests tumor progression in vivo. Sci Rep. 9(1):1–14
Marinho FF, Simões AO, Barcellos T, Moura S (2016) Brazilian Tabernaemontana genus: indole alkaloids and phytochemical activities. In: Fitoterapia, vol 114. Elsevier, New York, pp 127–137
Miller SL, Aroniadou-Anderjaska V, Figueiredo TH, Prager EM, Almeida-Suhett CP, Apland JP et al (2015) A rat model of nerve agent exposure applicable to the pediatric population: the anticonvulsant efficacies of atropine and GluK1 antagonists. Toxicol Appl Pharmacol 284(2):204–216
Mishra A, Aslam J, Verma C, Quraishi MA, Ebenso EE (2020) Imidazoles as highly effective heterocyclic corrosion inhibitors for metals and alloys in aqueous electrolytes: a review. J Taiwan Ins Chem Eng 114:341–358
Misra N, Luthra R, Singh KL, Kumar S (1999) Recent advances in biosynthesis of alkaloids. In: Comprehensive natural products chemistry. Elsevier, Pergamon, pp 25–59
Muthaura CN, Rukunga GM, Chhabra SC, Mungai GM, Njagi ENM (2007) Traditional phytotherapy of some remedies used in treatment of malaria in Meru district of Kenya. South Afr J Bot 73(3):402–411
Namukobe J, Kiremire BT, Byamukama R, Kasenene JM, Dumontet V, Guéritte F et al (2014) Cycloartane triterpenes from the leaves of Neoboutonia macrocalyx L. Phytochemistry 102:189–196
Nanjala C, Ren J, Mutie FM, Waswa EN, Mutinda ES, Odago WO et al (2022) Ethnobotany, phytochemistry, pharmacology, and conservation of the genus Calanthe R. Br. (Orchidaceae). J Ethnopharmacol 285:114822
Neag MA, Mocan A, Echeverría J, Pop RM, Bocsan CI, Crisan G et al (2018) Berberine: botanical occurrence, traditional uses, extraction methods, and relevance in cardiovascular, metabolic, hepatic, and renal disorders. Front Pharmacol 9:557
Nidorf SM, Eikelboom JW, Budgeon CA, Thompson PL (2013) Low-dose colchicine for secondary prevention of cardiovascular disease. J Am Coll Cardiol 61(4):404–410
O’Connor SE (2010) Alkaloids. In: Comprehensive natural products II [Internet]. Elsevier [cited 2022 Jan 17]. pp 977–1007. https://linkinghub.elsevier.com/retrieve/pii/B9780080453828000137
Ogunbodede O, McCombs D, Trout K, Daley P, Terry M (2010) New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) (“ San Pedro” ) and their relevance to shamanic practice. J Ethnopharmacol 131(2):356–362
Ottaggio L, Bestoso F, Armirotti A, Balbi A, Damonte G, Mazzei M et al (2008) Taxanes from shells and leaves of Corylus avellana. J Nat Prod. 71(1):58–60
Ou S, Zhao YD, Xiao Z, Wen HZ, Cui J, Ruan HZ (2011) Effect of lappaconitine on neuropathic pain mediated by P2X 3 receptor in rat dorsal root ganglion. Neurochem Int 58(5):564–573
Ouakki M, Galai M, Cherkaoui M (2022) Imidazole derivatives as efficient and potential class of corrosion inhibitors for metals and alloys in aqueous electrolytes: a review. J Mol Liq 345:117815
Pandrangi SL, Chalumuri SS, Garimella S (2022) Emerging therapeutic efficacy of alkaloids as anticancer agents. Ann Rom Soc Cell Biol 26(01):64–74
Panwar GS, Guru SK (2015 Jan 1 ) Stimulation of reserpine production in the whole plant culture of Rauwolfia serpentina L. by elicitors and precursor feeding. J Plant Biochem Biotechnol [Internet]. [cited 2022 Feb 10];24(1):49–55. https://link.springer.com/article/10.1007/s13562-013-0235-5
Pellati F, Benvenuti S (2008) Determination of ephedrine alkaloids in Ephedra natural products using HPLC on a pentafluorophenylpropyl stationary phase. J Pharm Biomed Anal 48(2):254–263
Peng W, Liu YJ, Hu MB, Yan D, Gao YX, Wu CJ (2017 Jan 5) Using the “target constituent removal combined with bioactivity assay” strategy to investigate the optimum arecoline content in charred areca nut. Sci Rep [Internet]. [cited 2022 Jan 18];7(1):1–12. https://www.nature.com/articles/srep40278
Pérez EG, Méndez-Gálvez C, Cassels BK (2012) Cytisine: a natural product lead for the development of drugs acting at nicotinic acetylcholine receptors. Nat Prod Rep 29:555–567
Petruczynik A (2012) Analysis of alkaloids from different chemical groups by different liquid chromatography methods. Cent Eur J Chem 10(3):802–835
Qing Z, Xu Y, Yu L, Liu J, Huang X, Tang Z, et al (2020 Jan 20) Investigation of fragmentation behaviours of isoquinoline alkaloids by mass spectrometry combined with computational chemistry. Sci Rep [Internet]. [cited 2022 Jan 17];10(1):1–13. https://www.nature.com/articles/s41598-019-57406-7
Qu SJ, Tan CH, Liu ZL, Jiang SH, Yu L, Zhu DY (2011) Diterpenoid alkaloids from Aconitum tanguticum. Phytochem Lett 4(2):144–146
Ratnadewi D (2017) Alkaloids in plant cell cultures. In: Alkaloids - alternatives in synthesis, modification and application [Internet]. IntechOpen [cited 2022 Jan 19]. https://www.intechopen.com/chapters/52980
Reiss GJ, Wyshusek M (2021) The layered crystal structure of bis(theophyllinium) hexachloridostannate (IV), C14H18N8O8SnCl6. Zeitschrift fur Krist New Cryst Struct 236(5):989–992
Renner UD, Oertel R, Kirch W (2005) Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Therap Drug Monit 27:655–665
Rios JL, Simeon S, Villar A (1989) Pharmacological activity of aporphinoid alkaloids. A review. Fitoterapia 60:387–412
Robenshtok E, Luria S, Tashma Z, Hourvitz A (2002) Adverse reaction to atropine and the treatment of organophosphate intoxication. Israel Med Assoc J 4:535–539
Robert C, Dummer R, Gutzmer R, Lorigan P, Kim KB, Nyakas M et al (2013) Selumetinib plus dacarbazine versus placebo plus dacarbazine as first-line treatment for BRAF-mutant metastatic melanoma: A phase 2 double-blind randomised study. Lancet Oncol. 14(8):733–740
Roberts MF, Strack D, Wink M (2018) Biosynthesis of alkaloids and betalains. In: Annual plant reviews online [Internet]. Wiley, Ltd [cited 2022 Jan 19], pp 20–91. https://onlinelibrary.wiley.com/doi/full/10.1002/9781119312994.apr0424
Rodak K, Kokot I, Kratz EM (2021) Caffeine as a factor influencing the functioning of the human body—friend or foe? Nutrients 13
Roddan R, Ward JM, Keep NH, Hailes HC (2020) Pictet–Spenglerases in alkaloid biosynthesis: future applications in biocatalysis. Curr Opin Chem Biol. 55:69–76
Rodriguez I, Alfonso C, Alfonso A, Otero P, Meyer T, Breitenbach U et al (2014) Toxin profile in samples collected in fresh and brackish water in Germany. Toxicon 91:35–44
Rolle J, Asante DO, Kok-Fong LL, Boucetta H, Seidu TA, Tai LLK, et al (2021) Jatrorrhizine: a review of its pharmacological effects [Internet]. vol 73, J Pharm Pharmacol. Oxford Academic [cited 2022 Jan 19]. pp 709–719. https://academic.oup.com/jpp/article/73/6/709/6209765
Rosales PF, Bordin GS, Gower AE, Moura S (2020) Indole alkaloids: 2012 until now, highlighting the new chemical structures and biological activities. In: Fitoterapia, vol 143. Elsevier, New York, p 104558
Rouden J, Lasne MC, Blanchet J, Baudoux J (2014) (-)-Cytisine and derivatives: Synthesis, reactivity, and applications [Internet]. vol 114, Chemical reviews. [cited 2022 Jan 18]. pp 712–78. https://pubs.acs.org/sharingguidelines
Saghatelyan T, Tananyan A, Janoyan N, Tadevosyan A, Petrosyan H, Hovhannisyan A et al (2020) Efficacy and safety of curcumin in combination with paclitaxel in patients with advanced, metastatic breast cancer: a comparative, randomized, double-blind, placebo-controlled clinical trial. Phytomedicine 70(March):153218
Sai C, Wang J, Li B, Ding L, Wang H, Wang Q, et al (2020 Jan 22) Isolation and identification of alkaloids from macleaya microcarpa by UHPLC– Q-TOF-MS and their cytotoxic activity in vitro, antiangiogenic activity in vivo. BMC Chem [Internet]. [cited 2022 Jan 20];14(1):1–11. https://bmcchem.biomedcentral.com/articles/10.1186/s13065-020-0660-1
Sanchez JA, Otero P, Alfonso A, Ramos V, Vasconcelos V, Aráoz R et al (2014) Detection of anatoxin-a and three analogs in Anabaena spp. cultures: new fluorescence polarization assay and toxin profile by LC-MS/MS. Toxins (Basel) 6(2):402–415
Schläger S, Dräger B (2016) Exploiting plant alkaloids. Curr Opin Biotechnol 37:155–164
Sevón N, Oksman-Caldentey KM (2002) Agrobacterium rhizogenes-mediated transformation: root cultures as a source of alkaloids [Internet]. vol 68, Planta Medica. Planta Med [cited 2022 Jan 20]. pp 859–68. https://pubmed.ncbi.nlm.nih.gov/12391546/
Sharma SK, Agnihotri AK (2021) Hairy root cultures and plant tropane alkaloids: production matrix and product in biotechnological perspective. In: Tropane alkaloids [Internet]. Springer, Singapore [cited 2022 Jan 20]. pp 89–104. https://link.springer.com/chapter/10.1007/978-981-33-4535-5_5
Sharma P, Padh H, Shrivastava N (2013) Hairy root cultures: a suitable biological system for studying secondary metabolic pathways in plants. Eng Life Sci 13:62–75
Shen Y, Liang WJ, Shi YN, Kennelly EJ, Zhao DK (2020) Structural diversity, bioactivities, and biosynthesis of natural diterpenoid alkaloids. Nat Prod Rep 37:763–796
Shojaei-Zarghani S, Yari Khosroushahi A, Rafraf M (2021) Oncopreventive effects of theanine and theobromine on dimethylhydrazine-induced colon cancer model. Biomed Pharmacother. 134:111140
Silva Teles MMR, Vieira Pinheiro AA, Da Silva DC, Fechine Tavares J, Barbosa Filho JM, Leitão Da Cunha EV (2019) Alkaloids of the lauraceae. In: Alkaloids: chemistry and biology. Academic Press, New York, pp 147–304
Singh A, Alvi NI (2011 Jan 1) High-performance thin-layer chromatographic quantification of yohimbine in the stem bark of Pausinystalia yohimbe. J Planar Chromatogr - Mod TLC [Internet]. [cited 2022 Feb 10];24(3):253–256. https://link.springer.com/article/10.1556/JPC.24.2011.3.15
Singh TP, Singh OM (2017) Recent progress in biological activities of indole and indole alkaloids. Mini Rev Med Chem 18(1):9–25
Siwach A, Verma PK (2021) Synthesis and therapeutic potential of imidazole containing compounds. BMC Chem 15:1–69
Sravanthi V, Sampath Kumar HM (2017) Immunomodulators in prophylaxis and therapy of Type-1 diabetes. In: Discovery and development of antidiabetic agents from natural products: natural product drug discovery. Elsevier, New York, pp 229–249
Srivastava S, Srivastava AK (2013) Biotechnology and genetic engineering for alkaloid production. In: Natural products: phytochemistry, botany and metabolism of alkaloids, phenolics and terpenes [Internet]. Springer, Berlin, Heidelberg [cited 2022 Jan 19]. pp 213–50. https://link.springer.com/referenceworkentry/10.1007/978-3-642-22144-6_95
Stohs SJ, Preuss HG, Shara M (2012) A review of the human clinical studies involving Citrus aurantium (bitter orange) extract and its primary protoalkaloid p-synephrine [Internet]. vol 9, International Journal of Medical Sciences. Ivyspring International Publisher [cited 2022 Feb 10]. pp 527–538. /pmc/articles/PMC3444973/
Stohs SJ, Shara M, Ray SD (2020) p-Synephrine, ephedrine, p-octopamine and m-synephrine: comparative mechanistic, physiological and pharmacological properties. Phytother Res 34:1838–1846
St-Pierre B, Vazquez-Flota FA, De Luca V (1999) Multicellular compartmentation of Catharanthus roseus alkaloid biosynthesis predicts intercellular translocation of a pathway intermediate. Plant Cell [Internet]. [cited 2022 Jan 19];11(5):887–900. https://pubmed.ncbi.nlm.nih.gov/10330473/
Supriya R, Kala RG, Thulaseedharan A (2020) Hairy Root culture: secondary metabolite production in a biotechnological perspective. In: Plant metabolites: methods, applications and prospects [Internet]. Springer, Singapore [cited 2022 Jan 20]. pp 89–110. https://link.springer.com/chapter/10.1007/978-981-15-5136-9_5
Sut S, Maggi F, Dall’Acqua S (2017) Bioactive secondary metabolites from orchids (Orchidaceae). In: Chemistry and biodiversity, vol 14. Wiley-VCH, Hoboken
Suzgec S, Bitis L, Sozer U, Ozcelik H, Zapp J, Kiemer AK et al (2009) Alkaloids from the aerial parts of Consolida anthoroidea and Delphinium linearilobum. Chem Nat Compd 45(2):287–289
Swamy MK (2020) Plant-derived bioactives: chemistry and mode of action. In: Plant-derived bioactives: chemistry and mode of action. Springer, New York, pp 1–589
Takla SS, Shawky E, Hammoda HM, Darwish FA (2018 Sep) Green techniques in comparison to conventional ones in the extraction of amaryllidaceae alkaloids: best solvents selection and parameters optimization. J Chromatogr A 14(1567):99–110
Tarabasz D, Kukula-Koch W (2020) Palmatine: a review of pharmacological properties and pharmacokinetics [Internet]. vol 34, Phytotherapy research. [cited 2022 Jan 19]. pp 33–50. https://pubmed.ncbi.nlm.nih.gov/31496018/
Tazi A, Lorillon G, Haroche J, Neel A, Dominique S, Aouba A et al (2017) Vinblastine chemotherapy in adult patients with langerhans cell histiocytosis: a multicenter retrospective study. Orphanet J Rare Dis 12(1):95
Terkeltaub RA, Furst DE, Bennett K, Kook KA, Crockett RS, Davis MW (2010) High versus low dosing of oral colchicine for early acute gout flare: twenty-four-hour outcome of the first multicenter, randomized, double-blind, placebo-controlled, parallel-group, dose-comparison colchicine study. Arthritis Rheum 62(4):1060–1068
Tóth B, Hohmann J, Vasas A (2018) Phenanthrenes: a promising group of plant secondary metabolites. J Nat Prod Am Chem Soc 81:661–678
Upadhyay SU, Patel VB, Patel AAUUM, Patel NM, Singh S, Pramod (2012) Pharma science monitor. Pharma Sci Monit 3:2085–2104
Van Den Bogaard B, Draijer R, Westerhof BE, Van Den Meiracker AH, Van Montfrans GA, Van Den Born BJH (2010) Effects on peripheral and central blood pressure of cocoa with natural or high-dose theobromine: a randomized, double-blind crossover trial. Hypertension 56(5):839–846
Verma A, Hartonen K, Riekkola ML (2008 Jan 1) Optimisation of supercritical fluid extraction of indole alkaloids from Catharanthus roseus using experimental design methodology - comparison with other extraction techniques. Phytochem Anal [Internet]. [cited 2022 Jan 20];19(1):52–63. https://onlinelibrary.wiley.com/doi/full/10.1002/pca.1015
Vrabec R, Maříková J, Ločárek M, Korábečný J, Hulcová D, Hošťálková A, et al (2022 Feb 1 ) Monoterpene indole alkaloids from Vinca minor L. (Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer’s disease. Phytochemistry [Internet]. [cited 2022 Feb 23];194:113017. https://doi.org/10.1016/j.phytochem.2021.113017
Wang X, Mao M, Liu S, Xu S, Yang J (2019) A comparative study of bolus norepinephrine, phenylephrine, and ephedrine for the treatment of maternal hypotension in parturients with preeclampsia during cesarean delivery under spinal anesthesia. Med Sci Monit 25:1093–1101
Wang F, Bi J, He L, Chen J, Zhang Q, Hou X et al (2021) The indole alkaloids from the roots of Isatidis Radix. Fitoterapia 153:104950
Weckerle CS, Stutz MA, Baumann TW (2003) Purine alkaloids in Paullinia. Phytochemistry 64(3):735–742
Wisniak J (2013) Pierre-Jean Robiquet. Educ Quim. 24(1):139–149
Xiong W, Chen X, Lv G, Hu D, Zhao J, Li S (2016 Dec 1) Optimization of microwave-assisted extraction of bioactive alkaloids from lotus plumule using response surface methodology. J Pharm Anal [Internet]. [cited 2022 Jan 20];6(6):382–8. https://pubmed.ncbi.nlm.nih.gov/29404007/
Xu JB, Li YZ, Huang S, Chen L, Luo YY, Gao F et al (2021) Diterpenoid alkaloids from the whole herb of Delphinium grandiflorum L. Phytochemistry 190:112866
Yan Y, Zhou H, Wu C, Feng X, Han C, Chen H, et al (2021) Ultrasound-assisted aqueous two-phase extraction of synephrine, naringin, and neohesperidin from Citrus aurantium L. fruitlets. Prep Biochem Biotechnol [Internet]. [cited 2022 Feb 10];51(8):780–791. https://www.tandfonline.com/doi/abs/10.1080/10826068.2020.1858427
Yao Y, Wang W, Shi W, Yan R, Zhang J, Wei G et al (2022) Overproduction of medicinal ergot alkaloids based on a fungal platform. Metab Eng 2021(69):198–208
Yates FS (1984) Pyridines and their benzo derivatives: (vi) Applications. In: Comprehensive heterocyclic chemistry. Elsevier, Pergamon, pp 511–524
Yin J, Xing H, Ye J (2008) Efficacy of berberine in patients with type 2 diabetes mellitus. Metabolism 57(5):712–717
Yin T, Zhang H, Zhang W, Jiang Z (2021) Chemistry and biological activities of hetisine-type diterpenoid alkaloids, vol 11. RSC Adv, pp 36023–36033
Yu X, Wei P, Wang Z, Liu Y, Wang L, Wang Q (2016) Design, synthesis, antiviral activity and mode of action of phenanthrene-containing N-heterocyclic compounds inspired by the phenanthroindolizidine alkaloid antofine. Pest Manag Sci. 72(2):371–378
Zein AL, Valluru G, Georghiou PE (2012) Recent asymmetric syntheses of tetrahydroisoquinolines using “named” and some other newer methods. In: Studies in natural products chemistry. Elsevier, New York, pp 53–80
Zhang QW, Lin LG, Ye WC (2018) Techniques for extraction and isolation of natural products: a comprehensive review [Internet]. vol 13, Chinese Medicine (United Kingdom). BioMed Central Ltd [cited 2022 Jan 20]. pp 1–26. https://cmjournal.biomedcentral.com/articles/10.1186/s13020-018-0177-x
Zhao W, He J, Zhang Y, Ito Y, Su Q, Sun W (2012) Preparative isolation and purification of alkaloids from Picrasma quassiodes (D. Don) Benn. by high-speed countercurrent chromatography. J Liq Chromatogr Relat Technol 35(11):1597–1606. https://doi.org/10.1080/10826076.2011.621150
Zhao T, Wang C, Bai F, Li S, Yang C, Zhang F et al (2019) Metabolic characterization of Hyoscyamus niger ornithine decarboxylase. Front Plant Sci 27(10):229
Zhou JT, Li CL, Tan LH, Xu YF, Liu YH, Mo ZZ et al (2017) Inhibition of Helicobacter pylori and its associated urease by Palmatine: investigation on the potential mechanism. PLoS One 12(1):1–15
Ziegler J, Facchini PJ (2008) Alkaloid biosynthesis: metabolism and trafficking. Ann Rev Plant Biol 59:735–769
Acknowledgments
The research leading to these results was supported by MICINN supporting the Ramón y Cajal grant for M.A. Prieto (RYC-2017-22891); by Xunta de Galicia supporting the program EXCELENCIA-ED431F 2020/12, the post-doctoral grant of L. Cassani (ED481B-2021/152), and the pre-doctoral grants of P. Garcia-Oliveira (ED481A-2019/295), and A.G. Pereira (ED481A-2019/0228); by the EcoChestnut Project (Erasmus+ KA202) that supports the work of J. Echave; and by the Bio Based Industries Joint Undertaking (JU) under grant agreement No 888003 UP4HEALTH Project (H2020-BBI-JTI-2019) that supports the work of P. Otero. JU receives support from the European Union’s Horizon 2020 research and innovation program and the Bio Based Industries Consortium. Authors are grateful to Ibero-American Program on Science and Technology (CYTED—AQUA-CIBUS, P317RT0003). The project SYSTEMIC Knowledge hub on Nutrition and Food Security has received funding from national research funding parties in Belgium (FWO), France (INRA), Germany (BLE), Italy (MIPAAF), Latvia (IZM), Norway (RCN), Portugal (FCT), and Spain (AEI) in a joint action of JPI HDHL, JPI-OCEANS, and FACCE-JPI launched in 2019 under the ERA-NET ERA-HDHL (n° 696295).
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Pereira, A.G. et al. (2023). Plant Alkaloids: Production, Extraction, and Potential Therapeutic Properties. In: Carocho, M., Heleno, S.A., Barros, L. (eds) Natural Secondary Metabolites. Springer, Cham. https://doi.org/10.1007/978-3-031-18587-8_6
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