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Nicotiana tabacum

Nicotiana tabacum, or cultivated tobacco, is an annually grown herbaceous plant of the genus Nicotiana. N. tabacum is the most commonly grown species in the genus Nicotiana, as the plant's leaves are commercially harvested to be processed into tobacco for human use. The plant is tropical in origin, is commonly grown throughout the world, and is often found in cultivation. It grows to heights between 1 to 2 metres (3.3 to 6.6 ft). Research is ongoing into its ancestry among wild Nicotiana species, but it is believed to be a hybrid of Nicotiana sylvestris, N. tomentosiformis, and possibly N. otophora.[1]

Nicotiana tabacum
Scientific classification Edit this classification
Kingdom: Plantae
Clade: Tracheophytes
Clade: Angiosperms
Clade: Eudicots
Clade: Asterids
Order: Solanales
Family: Solanaceae
Genus: Nicotiana
Species:
N. tabacum
Binomial name
Nicotiana tabacum

Description

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It is an annual plant that grows 1 to 3 metres (3 to 10 feet) high and is sticky hairy on all parts. The stems are thick and not very branched. The leaves can be over 50 centimetres (1 ft 8 in) long with the blades ovate to elliptical, or obovate, pointed towards the front and, at the base, run down the stem or are sessile, encompassing the stem.[citation needed]

The scented inflorescences are multi-branched panicles. The flower stalks are 5 to 15 millimetres (3⁄16 to 9⁄16 in) long. The calyx is 12 to 18 millimetres (1⁄2 to 11⁄16 in) and is covered with uneven 4 to 8 mm (3⁄16 to 5⁄16 in) narrow pointed calyx lobes shorter than the calyx tube. The crown is plate-shaped, the coronet is white, pink or red, the corolla tube greenish-cream, pink or red. The corolla tube has a total length of 3.5 to 4.5 cm (1+3⁄8 to 1+3⁄4 in) and is 3 to 5 mm (1⁄8 to 3⁄16 in) wide in the lower part and widens to 7 to 12 mm (1⁄4 to 1⁄2 in) in the upper part. The coronet is lobed or pentagonal. The stamens are designed unevenly and start below the center of the corolla tube. The anthers of the four longer stamens are close to the opening of the corolla tube or are slightly above it. The fifth stamen is significantly shorter than both longer pairs. The stamens have a length of 2.5 to 3.5 cm (1 to 1+3⁄8 in), significantly longer than the anthers, and are hairy at the base.[citation needed]

The fruit is a 1.5 to 2 cm (9⁄16 to 13⁄16 in) long capsule that is narrowly elliptical to egg-shaped. It can stand out over the calyx or be enclosed by it. The seeds are spherical or broadly elliptical and are up to 0.5 mm (1⁄64 in) long with a wavy networked surface.

Almost every part of the plant except the seed contains nicotine, but the concentration is related to different factors such as species, type of land, culture and weather conditions. The concentration of nicotine increases with the age of the plant. Tobacco leaves contain 2 to 8% nicotine combined as malate or citrate. The distribution of the nicotine in the mature plant is widely variable: 64% of the total nicotine exists in the leaves, 18% in the stem, 13% in the root, and 5% in the flowers.[citation needed]

Phytochemistry

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Natural tobacco polysaccharides, including cellulose, have been shown to be the primary precursors of acetaldehyde in tobacco smoke.[2] The main polyphenols contained in the tobacco leaf are rutin and chlorogenic acid. Amino acids contained include glutamic acids, asparagine, glutamine, and γ-Aminobutyric acid[3]

Pyridine alkaloids are present in tobacco as free bases and salts. Nicotine accounts for 90–95% of the plant's pyridines with nornicotine and anatabine accounting for roughly 2.5% each.[4] Pyridyl functional groups present in minute amounts include anabasine, myosmine, cotinine and 2, 3′-bipyridyl.[5] Indole alkaloids are also present in leaves and stems which includes harmala alkaloids as well. Yohimbine, harmine, harmaline and ajmalicine occurs in descending order, yohimbine being highest.[6]

The tobacco plant readily absorbs heavy metals from the surrounding soil and accumulates them in its leaves. These are readily absorbed into the user's body following smoke inhalation.[7]

Tobacco also contains the following phytochemicals: glucosides (tabacinine, tabacine), 2,3,6-trimethyl-1,4-naphthoquinone, 2-methylquinone, 2-napthylamine, propionic acid, anthalin, anethole, acrolein, cembrene, choline, nicotelline, nicotianine, and pyrene.[8]

Megastigmatrienone

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Tobacco aroma is due to presence of different volatile compounds; megastigmatrienone being the key flavor compound in tobacco.[9][10] Megastigmatrienone is used as flavour in tobacco products as well.[11]

Megastigmatrienone, a cyclohexenone,[12] and a carotenoid-derived aromatic compound, produces spice notes associated with wine.[9][13][14][15]

Megastigmatrienone is a metabolite of Brewer's yeast.[12]

Megastigmatrienone, as Tabanone, is manufactured by Symrise as a perfume ingredient.[16][17][18][19]

Habitat and ecology

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N. tabacum is a native of tropical and subtropical America, also appearing as a weed.[citation needed]

N. tabacum is sensitive to temperature, air, ground humidity and the type of land. Temperatures of 20–30 °C (68–86 °F) are best for adequate growth; an atmospheric humidity of 80 to 85% and soil without a high level of nitrogen are also optimal.

Parasites

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The potato tuber moth (Phthorimaea operculella) is an oligophagous insect that prefers to feed on plants of the family Solanaceae such as tobacco plants. Female P. operculella use the leaves to lay their eggs and the hatched larvae will eat away at the mesophyll of the leaf.[20]

Uses

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The plant is native to the Caribbean, where the Taíno people were the first recorded peoples to use it and cultivate it. In 1560, Jean Nicot de Villemain, then French ambassador to Portugal, brought tobacco seeds and leaves as a "wonder drug" to the French court. In 1586 the botanist Jaques Dalechamps gave the plant the name of Herba nicotiana, which was also adopted by Linné. It was considered a decorative plant at first, then a panacea, before it became a common snuff and tobacco plant.[citation needed]

Tobacco arrived in Africa at the beginning of the 17th century. The leaf extract was a popular pest control method up to the beginning of the 20th century. In 1851, the Belgian chemist Jean Stas documented the use of tobacco extract as a murder poison. The Belgian count Hippolyte Visart de Bocarmé had poisoned his brother-in-law with tobacco leaf extract in order to acquire some urgently needed money. This was the first exact proof of alkaloids in forensic medicine.[21]

It is now commercially cultivated worldwide. All parts of the plant contain nicotine, which can be extracted and used as an insecticide. The dried leaves can also be used; they remain effective for 6 months after drying. The juice of the leaves can be rubbed on the body as an insect repellent. The leaves can be dried and chewed as an intoxicant. The dried leaves are also used as snuff or are smoked. This is the main species that is used to make cigarettes, cigars, and other products. A drying oil is obtained from the seed.[citation needed]

Other varieties are cultivated as ornamental plants.

Curing and aging

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Dried tobacco at the North Carolina State Fair

After tobacco is harvested, it is cured (dried), and then aged to improve its flavor. There are four common methods of curing tobacco: air curing, fire curing, flue curing, and sun curing. The curing method used depends on the type of tobacco and its intended use. Air-cured tobacco is sheltered from wind and sun in a well-ventilated barn, where it air dries for six to eight weeks. Air-cured tobacco is low in sugar, which gives the tobacco smoke a light, sweet flavour, and high in nicotine. Cigar and burley tobaccos are air cured.[citation needed]

In fire curing, smoke from a low-burning fire on the barn floor permeates the leaves. This gives the leaves a distinctive smoky aroma and flavor. Fire curing takes three to ten weeks and produces a tobacco low in sugar and high in nicotine. Pipe tobacco, chewing tobacco, and snuff are fire cured.[citation needed]

Flue-cured tobacco is kept in an enclosed barn heated by flues (pipes) of hot air, but the tobacco is not directly exposed to smoke. This method produces cigarette tobacco that is high in sugar and has medium to high levels of nicotine. It is the fastest method of curing, requiring about a week. Virginia tobacco that has been flue cured is also called bright tobacco, because flue curing turns its leaves gold, orange, or yellow.[citation needed]

Sun-cured tobacco dries uncovered in the sun. This method is used in Greece, Turkey, and other Mediterranean countries to produce oriental tobacco. Sun-cured tobacco is low in sugar and nicotine and is used in cigarettes.[citation needed]

Once the tobacco is cured, workers tie it into small bundles of about 20 leaves, called hands, or use a machine to make large blocks, called bales. The hands or bales are aged for one to three years to improve flavor and reduce bitterness.[citation needed]

Ethnomedicinal uses

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The regions that have histories of use of the plant include:[citation needed]

  • Brazil: The leaf juice is taken orally to induce vomiting and narcosis.
  • Colombia: Fresh leaf is used as poultice over boils and infected wounds; the leaves are crushed with oil from palms and used as hair treatment to prevent baldness.
  • Cuba: Extract of the leaf is taken orally to treat dysmenorrhea.
  • East Africa: Dried leaves of Nicotiana tabacum and Securinega virosa are mixed into a paste and used externally to destroy worms in sores.
  • Ecuador: Leaf juice is used for indisposition, chills and snake bites and to treat pulmonary ailments.
  • Fiji: Fresh root is taken orally for asthma and indigestion; fresh root is applied ophthalmically as drops for bloodshot eyes and other problems; seed is taken orally for rheumatism and to treat hoarseness.
  • Guatemala: Leaves are applied externally by adults for myiasis, headache and wounds; hot water extract of the dried leaf is applied externally for ring worms, fungal diseases of the skin, wounds, ulcers, bruises, sores, mouth lesions, stomatitis and mucosa; leaf is orally taken for kidney diseases.
  • Haiti: Decoction of dried leaf is taken orally for bronchitis and pneumonia.
  • Hong Kong: Fresh leaves are mashed and combined with vegetable oil to create a potion that is applied to injuries for it to heal faster. This practice is also apparent in other places in China.
  • Iran: Infusion of the dried leaf is applied externally as an insect repellent; ointments made from crushed leaves are used for baldness, dermatitis and infectious ulceration and as a pediculicide.
  • Mexico (south-eastern): Among the ancient Maya, Nicotiana was considered a sacred plant, closely associated with deities of earth and sky, and used for both visionary and therapeutic ends. The contemporary Tzeltal and Tzotzil Maya of Highland Chiapas (Mexico) are bearers of this ethnobotanical inheritance, preserving a rich and varied tradition of Nicotiana use and folklore. The entire tobacco plant is viewed as a primordial medicine and a powerful botanical "helper" or "protector". Depending on the condition to be treated, whole Nicotiana leaves are used alone or in combination with other herbs in the preparation of various medicinal plasters and teas. In its most common form, fresh or green leaves are ground with slaked lime to produce an intoxicating oral snuff that serves as both a protective and therapeutic agent.[22]
  • United States: Extract of N. tabacum is taken orally to treat tiredness, ward off diseases, and quiet fear.
  • Tanzania: Leaves of Nicotiana tabacum are placed in the vagina to stimulate labour.
  • Zimbabwe: Leaves or root of the plant are infused and taken by mouth for asthma and other respiratory problems. Leaves and roots are also rubbed against warts and wounds as ointment.[23]
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See also

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References

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  1. ^ Ren, Nan; Timko, Michael P. (2001). "AFLP analysis of genetic polymorphism and evolutionary relationships among cultivated and wild Nicotiana species". Genome. 44 (4): 559–71. doi:10.1139/gen-44-4-559. PMID 11550889.
  2. ^ Talhout, R; Opperhuizen, A; van Amsterdam, JG (Oct 2007). "Role of acetaldehyde in tobacco smoke addiction". Eur. Neuropsychopharmacol. 17 (10): 627–36. doi:10.1016/j.euroneuro.2007.02.013. PMID 17382522. S2CID 25866206.
  3. ^ Roberts, E.A.H. (1951). "The polyphenols and amino acids of tobacco leaf". Archives of Biochemistry and Biophysics. 33 (2): 299–303. doi:10.1016/0003-9861(51)90109-9. PMID 14886011.
  4. ^ C. Laszlo, K. Kaminski, H. Guan, M. Fatarova, J. Wei, A. Bergounioux, W. K. Schlage, S. Schorderet-Weber, P. A. Guy, N. V. Ivanov, K. Lamottke and J. Hoeng (Nov 2022). "Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species", Molecules 2022, 27(22), 8105. [1]
  5. ^ Zhang, Jianxun; et al. (2007). "Selective Determination of Pyridine Alkaloids in Tobacco by PFTBA Ions/Analyte Molecule Reaction Ionization Ion Trap Mass Spectrometry". Journal of the American Society for Mass Spectrometry. 18 (10): 1774–1782. doi:10.1016/j.jasms.2007.07.017. PMID 17716908. S2CID 23808750.
  6. ^ Tarkowská D (July 2020). "A Fast and Reliable UHPLC-MS/MS-Based Method for Screening Selected Pharmacologically Significant Natural Plant Indole Alkaloids". Molecules (Basel, Switzerland). 25 (14): 3274. doi:10.3390/molecules25143274. PMC 7397342. PMID 32708364.
  7. ^ Pourkhabbaz, Alireza; Pourkhabbaz, Hamidreza (2012). "Investigation of Toxic Metals in the Tobacco of Different Iranian Cigarette Brands and Related Health Issues". Iran J Basic Med Sci. 15 (1): 636–644. PMC 3586865. PMID 23493960.
  8. ^ Zhang, Xiaotao; Wang, Ruoning; Zhang, Li; Ruan, Yibin; Wang, Weiwei; Ji, Houwei; Lin, Fucheng; Liu, Jian (2018). "Simultaneous determination of tobacco minor alkaloids and tobacco-specific nitrosamines in mainstream smoke by dispersive solid-phase extraction coupled with ultra-performance liquid chromatography/Tandem orbitrap mass spectrometry". Rapid Communications in Mass Spectrometry. 32 (20): 1791–1798. Bibcode:2018RCMS...32.1791Z. doi:10.1002/rcm.8222. PMID 29964303. S2CID 49639753.
  9. ^ a b Slaghenaufi D, Perello MC, Marchand-Marion S, Tempere S, de Revel G (February 2014). "Quantitative solid phase microextraction--gas chromatography mass spectrometry analysis of five megastigmatrienone isomers in aged wine". Analytica Chimica Acta. 813: 63–9. Bibcode:2014AcAC..813...63S. doi:10.1016/j.aca.2014.01.019. PMID 24528661.
  10. ^ Slaghenaufi D, Perello MC, Marchand S, de Revel G (July 2016). "Quantification of megastigmatrienone, a potential contributor to tobacco aroma in spirits". Food Chemistry. 203: 41–48. doi:10.1016/j.foodchem.2016.02.034. PMID 26948587.
  11. ^ Krüsemann, Erna JZ; Visser, Wouter F; Cremers, Johannes WJM; Pennings, Jeroen LA; Talhout, Reinskje (2018). "Identification of flavour additives in tobacco products to develop a flavour library". Tobacco Control. 27 (1): 105–111. doi:10.1136/tobaccocontrol-2016-052961. ISSN 0964-4563. PMC 5801651. PMID 28190004.
  12. ^ a b "Megastigmatrienone (YMDB01739)". Yeast Metabolome Database. Archived from the original on 15 January 2020. Retrieved 27 February 2022.
  13. ^ wikt:megastigmatrienone
  14. ^ Slaghenaufi, Davide; Perello, Marie-Claire; Marchand, Stéphanie; de Revel, Gilles (July 2016). "Quantification of megastigmatrienone, a potential contributor to tobacco aroma in spirits". Food Chemistry. 203: 41–48. doi:10.1016/j.foodchem.2016.02.034. PMID 26948587. Retrieved 27 February 2022.
  15. ^ "MEGASTIGMATRIENONE A". Inxight Drugs. National Center for Advancing Translational Sciences. Retrieved 27 February 2022.
  16. ^ "Tabanon". Ingredient Finder. symrise.com. Retrieved 27 February 2022.
  17. ^ "Tabanon" (PDF). Symrise. Retrieved 27 February 2022.
  18. ^ "Megastigmatrienone (Tabanone)". SincoPharmachem. Retrieved 27 February 2022.
  19. ^ Wiedemann, Joern; Kaufhold, Astrid (20 August 2013). "US8513180B2 Ethanol-free perfume oil microemulsion". google patents. Retrieved 27 February 2022.
  20. ^ Varela, L. G.; Bernays, E. A. (1988-07-01). "Behavior of newly hatched potato tuber moth larvae, Phthorimaea operculella Zell. (Lepidoptera: Gelechiidae), in relation to their host plants". Journal of Insect Behavior. 1 (3): 261–275. Bibcode:1988JIBeh...1..261V. doi:10.1007/BF01054525. ISSN 0892-7553. S2CID 19062069.
  21. ^ Wennig, Robert (2009). "Back to the roots of modern analytical toxicology: Jean Servais Stas and the Bocarmé murder case". Drug Testing and Analysis. 1 (4): 153–5. doi:10.1002/dta.32. PMID 20355192. S2CID 42750864.
  22. ^ Groark, Kevin P. (2010). "The Angel in the Gourd: Ritual, Therapeutic, and Protective Uses of Tobacco (Nicotiana tabacum) Among the Tzeltal and Tzotzil Maya of Chiapas, Mexico". Journal of Ethnobiology. 30 (1): 5–30. doi:10.2993/0278-0771-30.1.5. S2CID 86134500.
  23. ^ Maroyi, Alfred (2012). "Garden Plants in Zimbabwe: Their ethnomedicinal uses and reported toxicity". Ethnobotany Research and Applications. 10 (1): 54. doi:10.17348/era.10.0.045-057. hdl:10125/23547.
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