Open access peer-reviewed chapter

Study Biochemistry of Mentha longifolia (L.) Huds.: A Review

By Sadeq Sabeeh Kareem Al-Taie and Noor Falah Mahde Al-Kenane

Submitted: October 18th 2019Reviewed: May 5th 2020Published: July 23rd 2020

DOI: 10.5772/intechopen.92732

Downloaded: 331

Abstract

The Mentha longifolia were found to be a rich source of phytochemical compounds like piperitone, piperitone oxide, piperitenone, pulegone, d-limonene, menthone, carvone, menthol, β-caryophyllene, 1,8-cineole, 5,7,4-trihydroxy-6,2,3-trimethoxyflavone, carvone, limonene, tripal, and oxathiane. Mentha longifolia possess antioxidant effect that could be attributed to the presence of phytosterosls, unsaturated fatty acids, phenolic compounds, and specific volatile constituents and antimicrobial and interfere in the treatment of many diseases.

Keywords

  • biochemistry
  • Mentha longifolia (L.) Huds
  • essential oils
  • antioxidant activity

1. MenthaLinnaeus, Sp. Pl. 2: 576.1753

Menthaspecies belong to the family Lamiaceae (Labiatae) and are widely distributed in Asia, Africa, Europe, North America, and Australia [1].

Mentha is classified into 42 species including subspecies, varieties, cultivar, as well as several of hybrid species. There are five sections of Menthagenus: Audibertia, Mentha, Eriodontes, Preslia, and Pulegium[2]; this is classified according to genetic, cytological, and morphological features. The species of Mentha grow in numerous and different environments.

Menthaextracts have several traditional properties; it is used in foods and medicinal drugs. Literature search reported antioxidant, antimicrobial, antifungal, as well as effects against yeasts, and anti-inflammatory and sedative [3]. Lamiaceaespecies are carminative, treating of colds and flu, diuretic, respiratory tract problems, stomachache gastralgia, hemorrhoids and antispasmodic [4]. Phytochemical studies of Menthashowed the presence of phenolic compounds. Essential oil such as (limonene, carvone, β-caryophyllene, terpinen-4-ol, piperitenone, pulegone, 1,8-cineole, and menthol), terpenes, flavonoids, ascorbic acid [5].

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2. Morphological character

Mentha longifolia(Linnaeus) Hudson (Figure 1).

Figure 1.

Morphology ofMentha longifolia.

Mentha longifoliais a creeping rhizomatous, perennial herb, opposite, two leaves per node. Sessile, it grows 30–100 cm tall, either hairless or hairy on the stems; the leaves are round, simple, lanceolate to oblong lanceolate, toothed, 1–3 cm long, and 1.5–3 cm broad, smooth, or wrinkled with sharply serrate margin. The stem is erect, square-shaped, and light green to reddish green. Inflorescence, slender spikes produces pink, white, or lavender flowers in disrepute terminal spikes; bisexual, calyx short tubular, 1–2.5 mm, calyx short tubular, 1–2.5 mm, glabrous; corolla short tubular, 2–4 mm, with 5 lobes, white to pink, four stamens, subequal, pistil with a single style, exserted, the fruit is nutlets, dry, ovoid, and tuberculate, ovary smooth [6, 7, 8, 9].

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3. Phytochemistry of Mentha longifolia(Linnaeus) Hudson

The oils of M. longifoliaare known to contain numerous monoterpenoids with piperitone oxide, piperitone, piperitenone, β-caryophyllene, d-limonene, carvone, menthone, pulegone1,8-cineole, and menthol as dominating compounds [5].

The phytochemical compounds of the essential oil of M. longifoliaare studied by Moroccan [4] and reported that piperitenone oxide and piperitone oxide are the main compounds in the plant. In addition, five flavonoids and some non-volatile compounds are found such as trans-piperitone oxide, luteolin 7-O-glucoside and hesperidin, and piperitenone oxide luteolin. These compounds are used as antibacterial and against gastric problems and intraditional medicine [10, 11]. The essential oil of M. longifoliais represented by the oxygenated monoterpene group; this group includes 1,8-cineole, pulegone, piperitenone oxide [12, 13], and some other compound found in trace amounts such as sabinene, isomenthone, borneol, menthol, piperitenone, α-pinene, γ-terpineol, menthone, β-caryophyllene, isopulegone, and β-pinene.

Dzamic et al. [3] studied the M. longifoliain terms of its antioxidant and antifungal activity. They found that the constituents of the essential oils are about 35 chemical compounds. The highest compound was trans-dihydrocarvone (23.64%), and the lowest compound was cis-carveol and β-gurjunene (0.10%). As for minimal inhibitory (MIC) of M. longifoliaessential oil (μl/ml), the values of some fungi were as follows:

  1. 10 MIC in Aspergillus flavus, A. ochraceusand Trichoderma viride.

  2. 5 MIC in Alternaria alternateand Trichophyton mentagrophytes.

  3. 2.5 MIC in Aspergillus niger, A. versicolor, Cladosporium fulvum, Fusarium tricinctum, F. sporotrichioides, Penicillium funiculosum, P. ochrochloronand Candida albicans.

  4. 1 MIC in Cladosporium cladosporioides.

The values of fungicidal concentrations (MFC) of M. longifoliaessential oil (μl/ml) are as follows:

  1. 10 MFC in Alternaria alternate, Aspergillus niger, A. ochraceus, A. flavus, A, versicolor, Fusarium tricinctum, F. sporotrichioides, Penicillium funiculosumand Trichoderma viride.

  2. 5 MFC in Trichophyton mentagrophytesand Candida albicans.

  3. 2.5 MFC in Cladosporium cladosporioides, C. fulvum, and Penicillium ochrochloron.

They also illustrate antioxidant activity of M. longifoliaessential oil as shown in Figure 2.

Figure 2.

Antioxidant activity ofM. longifoliaessential oil [3].

The major components in the polish M. longifoliaoil are limonene (5.8%), carvone (7.9%), 1,8-cineole (5.4%). and piperitone (4.8%) [14].

According to Khani and Asghari [15], the major volatile compounds were oxathiane (9.3%), tripal (14.3%), piperitenone (43.9%), piperitone oxide (5.9%), and d-limonene (4.3%) in M. longifolia.

The major volatile compounds of the Iranian M. longifoliaoil were piperitone (43.9%), limonene (13.5%), and trans-piperitol (12.9%) [16]. Essential oil of M. longifoliashowed some major component as; pulegone (21.90%), 1,8-cineole (11.58%), piperitone oxide (42.51%), and caryophyllene oxide (3.64%) [17].

The most abundant components in the essential oil of M. longifoliafrom Pakistani flora were borneol (5.96%), piperitenone (24.9%), piperitenone oxide (28.3%), germacrene D (8.16%), and β-caryophyllene (5.94%), and the analyzed essential oil mainly consisted of oxygenated monoterpenes (67.24%) followed by sesquiterpene hydrocarbons (17.19%), monoterpene hydrocarbons (7.31%), and oxygenated sesquiterpenes (5.05%) [18].

Piperitone oxide and piperitenone oxide were the major components in the essential oil of M. longifoliafrom the middle Black Sea Region of Turkey [19].

In Egypt, a study prepared from M. longifoliaaerial parts [20] found fatty acid content of the petroleum ether extracts of M. longifoliaoil (the percentage of total fatty acids palimitic 1.63%, stearic 4.20%, linoleic 6.97%, and behenic 1.65%, total saturated fatty acids 7.488%, total unsaturated, fatty acids 6.97%), Gas liquid chromatography (GLC) analysis of unsaponifiable matter of M. longifolia oil (as percentage of total unsaponifiable matter) (hydrocarbon [higher alkanes], pentadecane 0.24%, hexadecane 0.03%, heptadecane 0.16%, octadecane 1.51%, nonadencane 15.94%, heneicosane 3.62%, docosane 10.548%, tetracosane 1.73%, hexacosane 0.576%, octacosane 4.09%, total hydrocarbon 38.47%, phytosterols [campesterol 3.37%, stigmasterol 1.87%, β-sitosterol 4.65%, total phytosterols 9.90%]) and chemical composition of hydrodistilled M. longifoliaessential oil are α-pinene, sabinene, β-pinene, β-myrcene, limonene 1,8-cineole, linalool oxide, linalool, menthone, borneol, piperitone oxide, terpinehe-4-ol, α-terpineol, transcarveol, thymole, piperitenone, piperitenone oxide, β-caryophyllene, humulene, D-germacrene, caryophyllene oxide, cedrol, α-cadinol, monoterpenes, oxygenated monoterpenes, sesquiterpene hydrocarbons, oxygenated sesquiterpene hydrocarbons.

M. longifoliaessential oil belongs to oxygenated monoterpene group, which include pulegone, piperitenone oxide, and 1,8-cineole [12, 13] Beyond these, carvone, limonene, sabinene, α-pinene, isomenthone, borneol, menthol, menthone, piperitenone, dihydrocarvone eucalyptol, γ-terpineol, β-caryophyllene, isopulegone, cadinene, and β-pinene were also recorded as meaningful compounds from M. longifoliaessential oil.

The chemical compounds of some species of the genus Mentha are explained in [21], and the Mentha longifolia was among them, mentioning the essential oils as shown in Table 1 and the phenolic compounds as shown in Table 2 in the M. longifolia.

ComponentReference
Piperitone[22]
Pulegone[23, 24]
Cis-piperitone epoxide[25]

Table 1.

The essential oils of M. longifoliadescribed in the literature.

Identified chemical compoundsReference
g, rosmarinic, salvianolic acid L[26]
5-Hydroxy-6,7,3′,4′-tetramethoxyflavone[3]

Table 2.

Major constituents of the phenolic composition and flavonoids of M. longifoliadescribed in the literature.

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4. Phytochemistry in other species of the MenthaL.

As for the other species of the genus Mentha, it was rich in some chemical compounds, and it has a large antimicrobial role, including the Mentha piperita L. rich in caffeine, p-coumaric, ferulic, and rosmarinic acids that have an anti-Staphylococcus aureusand antiproliferative activity against two cancerous cell lines (MDA-MB-231), breast carcinoma cell line, and (A375) human melanoma cell line [27].

Patil et al. [28] reported that Mentha piperitais rich in chemical compounds such as diterpenes, tannins, flavonoids, cardiac glycosides, and stimulants, alkalis, phenols, coumarin, and saponins. These compounds have high activity as a microbial antibody.

Authors [29, 30, 31] also recorded menthofuran as an aromatic oil that ranges between 11 and 70.5% of the total content of the Mentha aquatic.

In Mentha cervinaL. [32, 33], two compounds are mentioned; pulegone and isomenthone are the main components identified.

The Mentha diemenicaessential oil in Australia was neomenthyl acetate, pulegone, and menthone, while the essential oil of the same species from Canada had significantly higher amounts of menthone, isomenthone and pulegone [34].

As mentioned by [13, 17], Mentha spicataL. essential oils are carvone and limonene.

Guedes et al.[35] found some chemical compounds in Mentha arvensisL. and M. piperitaL. as shown in Figure 3.

Figure 3.

Main components ofMenthaspecies essential oils: (1) β-caryophyllene, (2) germacrene D, (3) limonene, (4) elemol, (5) geraniol, (6) linalool, (7) menthol, (8) neomenthol, (9) 3-octanol, (10) cis-sabinene hydrate, (11) trans-sabinene hydrate, (12) α-terpineol, (13) terpinen-4-ol, (14) viridoflorol, (15) decyl acetate, (16) dihydrocarvyl acetate, (17) 1,2-epoxyneomenthyl acetate, (18) menthyl acetate, (19) neoisomenthyl acetate, (20) neomenthyl acetate, (21) 3-octyl acetate, (22) α-terpinyl acetate, (23) carvone, (24) cis-dihydrocarvone, (25) trans-dihydrocarvone, (26) isomenthone, (27) menthone, (28) 3-octanone, (29) pulegone, (30) piperitenone, (31) piperitone, (32) 1,8-cineole, (33) menthofuran, (34) caryophyllene oxide, (35) piperitenone oxide, and (36) piperitone oxide [35].

The major component of essential oil in M. arvensiswas menthol in the stem (78.16%), but it was (43.7%) in stolon (runner). Menthol is the major component of all the oils in M. arvensis, with the highest percentage in shoot stem oil (78.16%) and the lowest in stolon (runner) stem oil (43.7%). β-Caryophyllene oxide was the major component present in stem and leaf, while limonene, α-phellandrene, menthone, pulegone, and terpinolene are found in stolon [36].

Al-Okbi et al. [20] studied chemical content Mentha citrateshown in Tables 3, 4 and 5.

Fatty acids%
Palmitic11.645
Stearic8.437
Oleic25.706
Linoleic8.986
Behenic3.777
Total saturated fatty acids23.859
Total unsaturated fatty acids34.692

Table 3.

Fatty acids’ content of the petroleum ether extracts of Mentha citrataoils (as percentage of total fatty acids) [20].

Hydrocarbon and sterols%
Hydrocarbon (higher alkanes)
Hexadecane0.005
Heptadecane0.231
Octadecane0.256
Nonadecane0.527
Icosane0.663
Heneicosane0.142
Docosane0.423
Tricosane24.715
Tetracosane1.816
Pentacosane0.266
Hexacosane4.217
Octacosane6.792
Total hydrocarbon40.053
Phytosterols
Campesterol4.284
Stigmasterol0.341
β-Sitosterol5.748
Total phytosterols14.657

Table 4.

GLC analysis of unsaponifiable matter Mentha citrataoils (as percentage of total unsaponifiable matter) [20].

Components%
Linalool20.99
Isopulegol0.17
Menthol0.25
Phenyl ethylalcohol1.32
α-Terpineol2.89
1,8-Cineole2.82
β-Ocimene1.01
α-Terpinolene0.53

Table 5.

Some chemical compounds (%) isolated from M. citrata[20].

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5. Antioxidant activity of Mentha longifolia(Linnaeus) Hudson

Iqbal et al. [18] showed dichloromethane and methanol extracts of M. longifoliato exhibit excellent antioxidant activity.

The antioxidant activity of methanol extract of M. longifoliais studied by Vladimir-Knezevid et al. [37], which they reported the presence of rosmarinic acid in the dried plants. Rosmarinic acid was found in the highest amount in most of Menthaspecies [38].

The antioxidant activity of M. longifoliamethanol extract has been investigated in Saudi Arabia [39]. Phytochemical compounds and antioxidant activity of M. longifoliawere studied by [36]. Essential oils have a high free radical scavenging capacity. So M. longifoliaessential oil represented as a safe antiseptic addition in antioxidant and pharmaceuticals [40, 41, 42, 43].

The antioxidant activity of M. longifoliain study [20] could be ascribed to the total phenolic contents that have been determined in methanol extract, along with the essential oil.

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6. Traditional indications of M. longifolia

Have been used as [22, 25]:

  1. Antimicrobial, anti-catarrhal, antispasmodic carminative, and antirheumatic

  2. Antiemetic, sedative, diuretic, and aphrodisiac

  3. Insect repellent and deworming

  4. Treatment of headaches

  5. Blood purifier

  6. Digestive disorders, jaundice and gallstone

  7. Dyspnea, common cold, asthma, and cough wound healing

  8. And other uses

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7. Conclusion

This review discusses the chemical constituent of Mentha longifoliaand its antioxidant and antimicrobial effect and its role in alternative medicine in various regions of the world.

Essential oils and other chemical compounds in plant are natural products, which have been used for several applications in pharmaceutical, cosmetic, agricultural, and bioactivity example stems, leaves, and flowers.

Menthagenus encompasses several species used at medical, industrial, and nutritional levels. Most species contain essential oils and phenolic compound such as M. longifolia, M. piperita, M. aquatic, M. cervina, M. diemenica, M. spicata, and M. arvensisrich in essential oils and other compounds show activities of antioxidant and antimicrobial, and their essential oils and their derived extracts used as natural food preservatives.

© 2020 The Author(s). Licensee IntechOpen. This chapter is distributed under the terms of the Creative Commons Attribution 3.0 License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Sadeq Sabeeh Kareem Al-Taie and Noor Falah Mahde Al-Kenane (July 23rd 2020). Study Biochemistry of <em>Mentha longifolia</em> (L.) Huds.: A Review, Herbs and Spices, Muhammad Akram and Rabia Shabir Ahmad, IntechOpen, DOI: 10.5772/intechopen.92732. Available from:

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