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Phytoconstituents of Mentha & Explanation on traditional

& modern therapeutic uses of Mentha or its constituents
with mechanism of action.
Assignment of

Pharmacognosy & Phytochemistry II

PHS CC 5104

Session 2024-25

Supervisor: Submitted by:

Prof. Umesh Mr. Devesh Rai

Kumar Patil Y22150022
B. Pharm V Sem
Mr. Rakesh
Kashyap
Miss. Shifa

Department of Pharmaceutical
Sciences
Dr. Harisingh Gour Vishwavidyalaya, Sagar, (M.P.)
(A Central University)
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CONTENT TABLE
1.MENTHA
1.1 Characteristics
1.2 Mentha oil
2. CHEMICAL CONSTITUENTS
3. THERAPEUTIC USES OF MENTHA
3.1 Antioxidant properties
3.2 For Gastrointestinal Disorders
3.3 Antibacterial Properties
3.4 Other uses
4. Referneces
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1.MENTHA
 Synonym- Brandy Mint, Peppermint ,Mentha piperita, Labiatae.
 It is the oil obtained by the distillation of Mentha piperita, belonging to family
Labiatae.
 Geographical Source It is mainly found in Europe, United States, and also in damp
places of England.
(Shah B;et.all;2009)

 The present literature suggests the classification of the genus Mentha into the three
basic lines named: capitatae, spicatae and verticillatae, based on the characteristic
inflorescence.
(Mahendran G;et.all;2021)

 Oil of Mentha: They distinctly deposit a solid substance upon chilling i.e., menthol
and thymol respectively, and leaving behind a liquid portion as a ‘mother liquor’.
(Kar A;2007)

 The former is termed as “Stearoptene” and the latter is known as “Oleoptene”.

 Mentha piperita is a highly aromatic perennial plant native to Europe and has been
used since ancient time as an important flavoring ingredient.
 In a series of clinical studies peppermint oil demonstrated antispasmodic activity on
gastrointestinal tract smooth muscle. This effect is principally due to the activity of
menthol, which is a calcium channel antagonist of the intestinal smooth muscle.
(Shah B;et.all;2009)

 Enteric-coated peppermint oil (0.2 mL) significantly decreased symptoms of irritable

bowel syndrome and seems to be more effective even than hyoscyamine.
(Kar A;2007)

 Peppermint is a herbaceous plant that grows to approximately 81 cm (32 in.) high.

The essential oil is obtained by steam distillation of the flowering plant tops.
 Seedlings and young plants of Mentha piperita, when treated with derivatives of
NAA, gave in the mature plants an increased yield (30–50%) of oil which itself
contained 4.5–9.0% more menthol than the controls.

 Breeding experiments have been performed with irradiated Mentha piperita in the
USA in an endeavour to produce a dominant mutation (bud sport) for Verticillium
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(wilt) resistance, a disease to which mints are particularly prone; a successful strain,
Todd’s Mitcham Peppermint, is now cultivated.
 Hybrids between various species of Mentha have been used to study the inheritance
of a number of essential oil components, including menthol, carvone and pulegone.
(Evans CW;2010)

 The biogenesis of rosmarinic acid (α-O-caffeoyl-3,4-dihydroxyphenyl-lactic acid),

the second most common ester of caffeic acid in the plant kingdom, was studied
in Mentha arvense and Mentha piperita.
(Ellis B;et.all;1970)

1.1 Characteristics
 Mint has more or less crumpled, opposite, ovate-lanceolate leaves, 3–7 cm
long. The apex is acute or acuminate, and the margin unequally serrate. The
leaves differ from those of peppermint in that they are almost sessile and
have a bright green colour free from purple.
(Shah B;et.all;2009)

 From creeping rootstocks, erect, square stems rise to a height of about 2 feet,
with very short-stalked, lance-shaped, acute-pointed, wrinkled, bright green
leaves. It has finetoothed edges and smooth surfaces, the ribs very prominent
on the lower surface. Leaves are sessile, lanceolate to oblong, acute apex,
and coarsely dentate margin.
(Evans CW;2010)

 The flowers are densely arranged in whorls in the axils of the upper leaves,
forming slender, cylindrical, tapering spikes, pinkish in colour. The plant has
characteristic taste and odour.

(Shah B;et.all;2009 pg 248)

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1.2Mentha Oil
 The oil is obtained by stream distillation of the fresh flowering tops of the plants
known as Mentha piperita Linn; Mentha arvensis var-piperascens (Japanese Mint
(Family: Labiatae).
(Shah B; et.all;2009)

 Based on phylogenetic analysis of morphology, chromosome numbers and major

essential oil constituents the genus Mentha (mint), an important member of
the Lamiaceae family, is highly diverse . It is represented by about 19 species and
13 natural hybrids, mainly perennial herbs, growing wildly in damp or wet places
throughout the temperate regions of Europe, Asia, Africa, Australia and North
America. Mints are fast growing, invasive and generally tolerate a wide range of
agro-climatic conditions.
 Mentha oil is commercially cultivated in U.P., Himachal Pradesh, Punjab,
Haryana, Jammu and Kashmir and Central India. It contains about 80% of l-
menthol.
 It is also cultivated in Japan, Brazil and California. They are colourless or pale
yellow liquid; strong and penetrating odour and taste is pungent and sensation of
a cool feeling when air is drawn into the mouth.
 Mentha oil contains chiefly l-menthol to the extent of 70% in free, as well as, in
the form of esters, depending upon variety (like American, Japanese, Indian).
American mentha oil contains 80% menthol while Japanese oil contains 70–90%.
(Kokate CK; et.all;2009)

 Other important constituents of the peppermint oil are menthone, menthofuran,

Jasmone, menthyl isovalerate, menthyl acetate and several other terpenes
derivatives.
 The other terpene includes 1-limonene, isopulegone, cineole, pinene, camphene,
etc., Jasmone and esters are responsible for pleasant flavour, while menthofuran
causes resinilication and develops dirty smell.
(Shah B; et.all;2009)
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 It is normally prepared from Japanese Peppermint Oil, from the flowering tops of
Mentha avensis Linne’ var piperascens, by subjecting it to refrigeration below –
22o C whereby the menthol crystallizes out distinctly.
(Kar A;2009)

 The crystals of menthol are separated by filteration and squeezes between layers
of filter papers to remove the adhering oil and finally purified by recrystallization.
 Peppermint Leaf as defined in the BP and EP is the dried leaves of Mentha ×
piperita L. (Labiatae). It is required to contain not less than 1.2% of volatile oil.
The oil is obtained from the same plant by steam distillation using the flowering
tops
 Spearmint or ordinary garden mint consists of the dried leaf and flowering top of
Mentha spicata L. (M. viridis Linn.) and Mentha × cardiaca (Labiatae). The BP
oil is prepared by steam distillation and should contain not less than 55% of
carvone, 2–25% limonene with upper limits for a number of other constituents as
determined by gas chromatography.

 De-mentholized Mint- Oil BP This is cited as the volatile oil from Mentha
arvensis var. piperascens from which the menthol has been partially removed. The
two commercial oils, Brazilian and Chinese, differ somewhat in their ranges of
ester and alcohol contents; standards are given for each. For both, the
cineole:limonene ratio, as determined by GC, is less than unity.
(Evans CW ; 2010)

 Menthol has three chiral centres, hence it would give rise to eight optically active
isomers and four racemic forms. Menthol on oxidation gives menthone (a
ketone), by the sacrifice of one chiral centre; therefore, the resulting menthone
must exist in four optically active isomers and two recemic forms and all, these
have been actually prepared.
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(Shah B;2009 pg 426)

1.2.1 Isolation
Mentha oil is obtained from the hydrodistillation or steam distillation of fresh
above-ground parts just before flowering. For (-) menthol isolation from
peppermint oil the oil is subjected to cooling. The crystals of menthol crystallize
out from the oil which is separated by centrifugation. Cornmint oil obtained from
the steam distillation of the flowering herb Mentha arvensis contains about 70–
80% of free (-) menthol. Cornmint oil is cooled and the crystals of menthol
produced are separated by centrifugation. Since the crystalline product contains
traces of cornmint oil, this menthol has a slightly herbaceous minty note. Pure (-)
menthol is obtained by re-crystallization from solvents with low boiling points.
Dementholized corn mint oil from which (-) menthol is removed by
crystallization and which still contains 40–50% free menthol can also be reused
for producing (-) menthol. Melting point: 41–44°C
(Shah B;et.all;2009)

2.CHEMICAL CONSTITUENTS
 It contains about 0.5% volatile oil containing carvone. It also contains limonene,
phellandrine, dihydrocarveol acetate, esters of acetic, butyric, and caproic or
caprylic acids. The drug also contains resin and tannins.
(Kokate CK; et.all;2009)

 Carvone- Chemical Structure 2-Methyl-5-(1-methylethenyl)-2-cyclohexene-1-one

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 Occurrence It occurs in the mandarin peel oil (Citrus reticulata Blanco., Family:
Rutaceae); spearmint oil upto 70% (Mentha spicata or Mentha cardiaca, Family:
Lamiaceae); gingergrass oil
(Kar A;2009)

 Peppermint oil contains chiefly - menthol to the extent of 70 per cent in free, as
well as, in the form of esters, depending upon variety (ike American, Japanese,
Indian).
 American peppermint oil contains 80 per cent menthol while Japanese oil
contains 70 - 90 per cent. Other important constituents of the peppermint oil are
menthone, menthofuran, jasmone, menthyl isovalerate, menthyl acetate and
several other terpene derivatives, The other terpenes include Limonene,
isopulegone, cineole, pinene, camphene, etc.
(Shah B; et.all;2009)

(Kokate CK; et.all;2009 pg 14.61)

 The main constituents of the essential oil are a- and b-pinene, limonene, cineol,
ethyl amylcarbinol, menthone, menthol, isomenthol, menthyl acetate, and
piperitone. It has a strong mint odor with a sweet balsam taste masked by a strong
cooling effect. It is widely used in foods, as well as in liquid pharmaceuticals, to
8000 ppm.
(Walker JT; et.all;1996)

 Mint plants either produce C3-oxygenated p-menthane (e.g., pulegone, menthone,

menthol) or C6-oxygenated p-menthane (e.g., carvone) types, as major
monoterpenes .
(Evans CW;2010)
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 Hydrocarbons (β-caryophyllene, germacrene D, limonene), alcohols (elemol,

geraniol, linalool, menthol, neomenthol, 3-octanol, cis/trans-sabinene hydrate, α-
terpineol, terpinen-4-ol, viridoflorol), esters (decyl acetate, dihydrocarvyl acetate,
1,2-epoxyneomenthyl acetate, menthyl acetate, neoisomenthyl acetate,
neomenthyl acetate, 3-octyl acetate, α-terpinyl acetate), ketones
(carvone, cis-/trans-dihydrocarvone, isomenthone, menthone, 3-octanone,
pulegone, piperitenone, piperitone), and ethers (1,8-cineole, menthofuran,
caryophyllene oxide, piperitenone oxide, piperitone oxide) were also found as
main components of Mentha species essential oils
(Shah B; et.all;2009)

 Along with menthol the oil contains (+) neomenthol, (+) isomenthol, menthone,
menthofuran, menthyl acetate and cineol. The menthol obtained from the natural
sources is. Levorotatory (l-menthol) or racemic (dl-menthol). Menthol can be
synthetically prepared by hydrogenation of thymol.
(Kar A;2009)

 In M. piperita essential oil 26 components were detected and identified (97.7%).

Menthol (37.4%), menthyl acetate (17.4%) and menthone (12.7%) were the main
components in this oil. In essential oil of M. spicata 27 components were
identified (92.4%).
 The main components were carvone (49.5%) and menthone (21.9%) . The results
of antifungal activities of both essential oils and components are presented in .
The essential oil of M. spicata showed the same fungistatic activity in macro- and
microdilution method with of 1.0-2.5 μL/mL in ethanol and 0.5-1.5 μL/mL in
Tween. MICs of M. piperita essential oil were higher, 1.5-3.0 μL/mL in ethanol
and 1.0-2.5 μL/mL in Tween.
(Gershenzon J; et.all;2009)

3. THERAPEUTIC USES OF MENTHA

Peppermint or Mentha oil is used as carminative, stimulant, and flavouring agent. It has
m antiseptic properties too, it is used in toothpaste, tooth powders, shaving cream and
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different pharmaceutical dosage forms. It is also consumed in the preparation of chewing

gums, candies jellies, perfumes and essences. Menthol is manufactured in India by S, H.
Kelkar and Co, Bhavr Chemicals, Procter and Gamble Lid. and several others. India
produces about 500 tonnes ce menthol annually-
Both mentha oil and menthol have calcium channel blocking activity causing spasmolytic
and smooth muscle relaxant effects, and hence useful in irritable bowel syndrome. They
show better pharmacokinetic profile when given by enteric coated capsules for release in
large intestine. Muscie relaxant activity is employed to reduce spasm during endoscopy
of colon.
For this purpose,
emulsified oil is injected through biopsy channel of the endoscope. Mentha oil shows
digestare activity by stimuläting bile flow. This is also supported by flavonoid pigments
of leaf. Azulene fie the leaf is believed to be anti-inflammatory and anti-ulcer in activity.
For the nasal decogestar: effect menthol is considered by U.S.F.D.A. as generally
regarded as safe (GRAS). Mentha oil is used for inhalation in steam, as well as topical
products and lozenges for its antitussive effects.
Peppermint oil and menthol are being exported from india since a decade, The export
values during 1994-95 were 7 2890 lakhs and 2 623 lakhs for menthol and peppermint oil
respectively.
(Kokate CK; et.all;2009)

3. 1. Antioxidant Properties
Lack of antioxidants in organism, promotes the oxidative stress due to the presence
of free radicals, which in turn causes a variety of pathological conditions.
Antioxidants, which are an integral part of biologically active substances, are of
great interest. They can reduce mutagenic influence, regulating the oxidation process
of free radicals.
According to literature, a number of biologically active substances, which are
produced by plants and have antioxidant activity, are known. They include α-
tocoferol (vitamin E), tannins, ascorbic acid (vitamin C), β- carotene, a number of
protein compounds with enzymatic activity, flavonoids, polysaccharides, terpenoids,
polyphenol compounds and etc.
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Mentha pipertita have antioxidant properties due to presence of several bioactive

substances. The antioxidant properties of Mentha pipertita are important to prevent
inflammation process and dyslipidemia as well as several chronic degenerative
diseases as diabetes and cardiovascular diseases
(Li Y; et.all;2017)

3.2 For Gastrointestinal Disorders

 The medical use of mints for gastrointestinal affections is present in the works of
most philosophers and physicians who came across them, from classical antiquity to
present-day medicine.
 Mints have been consistently referred to as possessing anti-emetic and carminative
properties, and being used to facilitate digestion and assist in the treatment of
gastrointestinal disorders.
 The gastrointestinal usefulness attributed to mints has been uncovered in recent
scientific publications. Mint oils possess substances that increase gastric emptying to
improve digestion and relax the bowel. Its antiemetic properties are of considerable
magnitude as they can reduce postoperative, chemotherapy-induced nausea and
vomiting. Their spasmolytic properties are known to relieve symptoms of irritable
bowel syndrome .
 They are safe to be used in endoscopic procedures, as a suitable alternative to
conventional spasmolytics, and increase the diagnostic sensitivity of the procedure
itself .
 The carminative (i.e., reliever of flatulence) and spasmolytic properties of mints were
also much appreciated. Paulus Aegineta provided a recipe for constipation in
children, for which he advised rubbing the abdomen with a mixture of mint and
honey .
(Tayarani-NZ; et.all;2013)

 Using peppermint water as a palliative treatment for digestive and spasmodic

problems and mentioned the activity of mints’ oils against a multitude of pathogenic
microorganisms, including Vibrio cholera, the causative agent of cholera.
(Li Y; et.all;2017)

3.3 Antibacterial Properties

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 The constituents of the essential oil of M. piperita have different modes of action in
bacteria and eukaryotic cells. They exhibit strong bactericidal properties, and in
eukaryotic they modify apoptosis and differentiation, interfere with the post
translational modification of proteins and induce or inhibit certain liver detoxifying
enzymes.
(Karpavičienė B;2022)

 Antibacterial activity of plants may be attributed to the presence of phenolic

compounds that behave as prooxidants because they undergo high oxidation, so
instead of eliminating the reaction of free radical chain, they lead to generation of
superoxide and quinones. The most easily oxidized phenolics such as quercetin and
gallic acid have pro-oxidant activity but tannins, due to the high molecular weight
have little pro-oxidant activity.
 The extracts can be categorized into several classes among which are terpenoids,
flavonoids and phenolics that are known to be active against bacteria, viruses and
protozoa. The antimicrobial effects of the essential oil can be attributed to their
mechanisms of action within the cell membrane. The implications of this mechanism
involves lysis and loss of membrane integrity due to changes that determine the
output of ions (hydrogen, potassium and calcium), causing damage in the essential
cell survival processes. Menthol and menthone present in the essential oil
components of M. piperita is responsible for the antimicrobial activity.
(Mahendran G; et.all;2021)

3.4. Other uses

 Menthol is one of the main components of the essential oil of M. piperita that
produce anti-cancer activity inducing cell death, either by necrosis or apoptosis
(in Caco-2 cell line). The cytotoxicity associated with essential oil has been
attributed to various effects such as the production of reactive species, change
in fluidity and membrane permeability, tubulin polymerization, imbalance in
ion transport, and inhibition of protein function.
(Gershenzon J; et.all;2009)
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 M. piperita relaxes the lower esophageal sphincter, which is useful as an

antispasmodic agent by taking double contrast barium and in patients with
dyspepsia. It acts by inhibiting the spontaneous peristaltic activity, reducing the
total gastrointestinal transit and gastric emptying by lowering basal tone in the
intestinal tract, reducing low frequency waves in the esophagus, and small
intestine by slowing the peristaltic movements and inhibiting responses
induced by potassium depolarization. (Turner GW; et.all;2004)

4.REFERENCES
 Badal S , Delgoda R “Pharmacognosy Fundamentals, Applications and Strategy”
ELSEVIER Publications,2016, pg. 80,257
 Ellis BE, Towers G. “Biogenesis of rosmarinic acid in Mentha”. Biochemical journal.
1970 Jun 1;118(2):pg.291.
 Ewans CW “Trease and Evans Pharmacognosy” 16 th edition, 2010, ELSEVIER
Publication pg. . 113,114,267,268,269
 Gershenzon J, Maffei M, Croteau R. “Biochemical and histochemical localization of
monoterpene biosynthesis in the glandular trichomes of spearmint (Mentha spicata)”.
Plant physiology. 2009 Apr 1;89(4):pg.1351-3.
 Kar A , “Pharmacognosy and Pharmacobiotechnology”, second edition, New Age
International Publishers,2007, pg. 223,239
 Karpavičienė B. “Traditional Uses of medicinal plants in south-Western part of
Lithuania” Plants Physiology. 2022 Aug 11;11(16):pg.2091-2093.
 Kokate C.K, Purohit AP, Gokhale SB , “Pharmacognosy” 55 th edition , Nirali Prakashan,
2009 pg. 14.60,14.61,14.62
 Li Y, Liu Y, Ma A, Bao Y, Wang M, Sun Z. “In vitro antiviral, anti-inflammatory, and
antioxidant activities of the ethanol extract of Mentha piperita L”. Food science and
biotechnology. 2017 Dec;26:pg.1675-83.
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 Mahendran G, Verma SK, Rahman LU. “The traditional uses, phytochemistry and
pharmacology of spearmint (Mentha spicata L.)”: A review. Journal of
Ethnopharmacology. 2021 Oct 5;278: pg. 114261
 Shah B , Seth AK “Textbook Of Pharmacognosy and Phytochemistry” ELSEVIER
Publications , 2009 , pg. 284,285,286,426
 Tayarani-NZ, Talasaz-FE, Nasiri R, Jalali N, Hassanzadeh MK. “Antiemetic activity of
volatile oil from Mentha spicata and Mentha× piperita in chemotherapy-induced nausea
and vomiting”. ecancermedicalscience. 2013;pg.7 .
 Turner GW, Croteau R. “Organization of monoterpene biosynthesis in Mentha.
Immunocytochemical localizations of geranyl diphosphate synthase, limonene-6-
hydroxylase, isopiperitenol dehydrogenase, and pulegone reductase”. Plant physiology.
2004 Dec 1;136(4):pg. 4215-27.
 Walker JT, Melin JB.” Mentha x piperita, Mentha spicata and effects of their essential
oils on Meloidogyne in soil”. Journal of Nematology. 1996 Dec;28(4S):pg.629.
 Yousefian S, Esmaeili F, Lohrasebi T. “A Comprehensive Review of the Key
Characteristics of the Genus Mentha, Natural Compounds and Biotechnological
Approaches for the Production of Secondary Metabolites”. Iranian Journal of
Biotechnology. 2023 Oct;21(4):pg.3605.