Monarda Species | Encyclopedia MDPI

Monarda Species: Comparison

View Latest Version

Please note this is a comparison between Version 2 by William N. Setzer and Version 3 by Vivi Li.

The genus

Monarda

(family Lamiaceae) contains 22 species of which three are native to southern Alabama,

M. citriodora

M. fistulosa

, and

M. punctata

. Several species of

Monarda

have been used in traditional medicines of Native Americans, and this present study is part of an ongoing project to add to our understanding of Native American pharmacopeia.

Monarda citriodora
Monarda fistulosa
Monarda punctata
essential oil
thymol
carvacrol
p-cymene

1. Introduction

The Plant List [1] shows 22 different

Monarda

L. (Lamiaceae) species, 18 of which occur in the United States [2]. There are three

Monarda

species native to south Alabama, namely

Monarda citriodora

Cerv. ex Lag.,

Monarda fistulosa

L., and

Monarda punctata

L. (see

Figure 1

) [2].

Figure 1.

Monarda species discussed in this work (photographs by S. K. L).

species discussed in this work (photographs by S. K. L).

Several

Monarda

species have been used by Native Americans as medicinal plants [3]. For example,

M. fistulosa

was used by the Blackfoot, Navajo, Lakota, and Winnebago people to treat boils, cuts and wounds; the Cherokee, Chippewa, Flathead, Ojibwa, and Tewa used the plant to treat colds, fever, and influenza; the Crow, Lakota, Menominee, and Ojibwa used the plant for coughs, catarrh, and other respiratory problems.

Monarda punctata

was used by the Delaware, Mohegan Nanticoke, and Navajo tribes to treat colds, fever coughs, and catarrh.

2. Essential oil from Monarda species

Monarda citriodora

and

M. fistulosa have been introduced throughout temperate regions of the world as popular herbal medicines as well as ornamentals ^[4][5][6]. The volatile phytochemistry has shown wide variation depending on geographical location (

have been introduced throughout temperate regions of the world as popular herbal medicines as well as ornamentals [4,5,6]. The volatile phytochemistry has shown wide variation depending on geographical location (

Table 4

). The essential oils of

M. citriodora

in the present study were rich in both thymol and carvacrol, whereas essential oils from Europe and Asia were dominated by thymol with much lower concentrations of carvacrol.

Monarda fistulosa

, in particular, showed wide variation with at least three different chemotypes (carvacrol-rich, thymol-rich, and geraniol-rich, see

Table 4

). The essential oils of

M. fistulosa

(samples #1 and #2) in this study fit into the thymol-rich chemotype. Interestingly, there was a high concentration of thymoquinone in

M. fistulosa

sample #3, with concomitant lower concentrations of thymol and carvacrol. Thymol was reported as the major component of

M. punctata in two old reports ^[7][8]. Consistent with these reports, a floral essential oil of

in two old reports [11,12]. Consistent with these reports, a floral essential oil of

M. punctata

from China was rich in thymol (75.2%), which is in agreement with the aerial parts essential oils from Alabama.

Table 4.

Major essential oil components of

Monarda

species from geographical locations around the world.

Monarda	spp.	Plant Tissue	Collection Site	Composition (Major Components)	Ref.
M. citriodora	Aerial parts	Jammu, India (cultivated)	Thymol (82.3%), carvacrol (4.8%)	^[9]	[13]
M. citriodora	Aerial parts	Imola (BO) Italy (cultivated)	Thymol (19.6%),	p	-cymene (15.6%), γ-terpinene (13.5%), carvacrol (9.3%), α-terpinene (9.2%), myrcene (5.7%)	^[10]	[14]
M. citriodora	Not reported	Commercial (India)	(	E	)-β-Caryophyllene (19.2%), citral	^a	(13.3%), limonene (11.8%),	cis	-verbenol (11.4%), geraniol (7.6%), citronellal (5.6%)	^[11]	[15]
M. citriodora	var.	citriodora	Leaves	Liverpool, UK (cultivated)	Thymol (50.7%),	p	-cymene (22.8%), carvacrol (3.6%)	^[12]	[16]
M. citriodora	var.	citriodora	Flowers	Liverpool, UK (cultivated)	Thymol (61.8%), γ-terpinene (13.3%),	p	-cymene (4.2%), carvacrol (3.8%)	^[12]	[16]
M. citriodora	var.	citriodora	Aerial parts	Liverpool, UK (cultivated)	Thymol (56.9%),	p	-cymene (13.0%), α-terpinene (10.0%), carvacrol (4.3%)	^[13]	[17]
M. citriodora	var.	citriodora	Aerial parts	Commercial (unknown)	Thymol (70.6%),	p	-cymene (10.6%), carvacrol (6.1%)	^[14]	[18]
M. fistulosa	Aerial parts	Krasnodarsk Krai, Russia (introduced, wild)	p	-Cymene (32.5%), carvacrol (23.9%), thymol (12.6%), carvacrol methyl ether (5.5%), unidentified aliphatic aldehyde (6.3%)	^[15]	[19]
M. fistulosa	Aerial parts	Casola Valsenio, Italy (cultivated)	Thymol (26.5%), β-phellandrene (17.0%), α-phellandrene (13.7%),	p	-cymene (13.5%), myrcene (8.1%)	^[16]	[20]
M. fistulosa	Aerial parts	Saint-Jean-sur-Richelieu, QC, Canada (cultivated)	Geraniol (61.8%), geranyl formate (16.6%), geranial (10.6%), neral (6.6%)	^[17]	[21]
M. fistulosa	Aerial parts	Poplarville, MS, USA (cultivated)	Carvacrol (39.1%),	p	-cymene (35.4%), (−)-1-octen-3-ol	^[18]	[22]
M. fistulosa	Aerial parts	Imola (BO) Italy (cultivated)	Thymol (31.6%), β-phellandrene (18.1%), α-phellandrene (14.2%),	p	-cymene (13.1%), myrcene (8.8%)	^[19]	[23]
M. fistulosa	Aerial parts	Imola (BO) Italy (cultivated)	Thymol (28.4%), β-phellandrene (16.9%), α-phellandrene (13.7%),	p	-cymene (13.3%), myrcene (8.7%)	^[20]	[24]
M. fistulosa	Aerial parts	Imola (BO) Italy (cultivated)	Thymol (33.4%), β-phellandrene (18.0%), α-phellandrene (14.0%),	p	-cymene (13.2%), myrcene (8.6%)	^[20]	[24]
M. fistulosa	Aerial parts	Ravenna, Italy (cultivated)	γ-Terpinene (25.2%), carvacrol (24.3%),	p	-cymene (11.0%; reported as	o	-cymene), thymol (8.4%), α-terpinene (5.0%), thymol methyl ether (4.7%)	^[21]	[25]
M. fistulosa	Aerial parts	Chişinău, Republic of Moldova (cultivated)	Carvacrol (54.8%),	p	-cymene (23.2%), carvacrol methyl ether (5.9%)	^[22]	[26]
M. fistulosa	Flowers	Gallatin Valley, MT, USA (wild)	Carvacrol (45.7%),	p	-cymene (25.6%), γ-terpinen (6.8%), thymol (3.1%)	^[23]	[27]
M. fistulosa	Leaves	Gallatin Valley, MT, USA (wild)	Carvacrol (71.5%),	p	-cymene (13.1%), γ-terpinen (2.5%), thymol (3.3%)	^[23]	[27]
M. fistulosa	Aerial parts	Moscow, Russia (cultivated)	α-Terpineol (37.7%), 1-octen-3-ol (10.5%), geraniol (10.4%), thymol (9.3%),	p	-cymene (4.9%)	^[24]	[28]
M. fistulosa	cv. Fortuna	Aerial parts	Kherson, Ukraine (cultivated)	Thymol (77.3%), carvacrol methyl ether (4.9%), carvacrol (3.8%)	[6]
M. fistulosa	cv. Premiera	Aerial parts	Kherson, Ukraine (cultivated)	Thymol (78.3%), carvacrol methyl ether (4.8%), carvacrol (3.6%)	[6]
M. fistulosa	var.	menthifolia	Aerial parts	Morden, Manitoba, Canada (cultivated)	Geraniol (86.8%)	^[25]	[29]
M. punctata	Flowers	Xi’an, China (cultivated?)	Thymol (75.2%),	p	-cymene (6.7%), limonene (5.4%), carvacrol (3.5%)	^[26]	[30]

^a Isomer not indicated.

The high concentrations of thymol, carvacrol, and

-cymene are consistent with the traditional uses of

Monarda spp. to treat skin infections, wounds, fevers, and respiratory problems. Thymol ^[27], carvacrol ^[28], and

spp. to treat skin infections, wounds, fevers, and respiratory problems. Thymol [31], carvacrol [32], and

p-cymene ^[29] have demonstrated antibacterial and antifungal activities ^[30][31], as well as wound-healing activity ^[32]. Thymol ^[33] and carvacrol ^[34], in addition to thymoquinone ^[35], have shown antitussive effects. Thymoquinone has also shown wound-healing properties ^[36]. Furthermore, both thymol ^[37] and carvacrol ^[28] have shown analgesic and anti-inflammatory activities ^[38].

-cymene [33] have demonstrated antibacterial and antifungal activities [34,35], as well as wound-healing activity [36]. Thymol [37] and carvacrol [38], in addition to thymoquinone [39], have shown antitussive effects. Thymoquinone has also shown wound-healing properties [40]. Furthermore, both thymol [41] and carvacrol [32] have shown analgesic and anti-inflammatory activities [42]. As far as we are aware, this work presents the first chiral analysis of terpenoid constituents of

Monarda

species. Several investigations on the enantiomeric distributions in other members of the Lamiaceae have been reported in the literature, however. There seems to be much variation in the enantiomeric distribution of monoterpenoids across the family. Consistent with what was observed in

Monarda

essential oils, (+)-α-pinene was the major enantiomer found in

Coridothymus capitatus ^[39],

[43],

Rosmarinus officinalis ^[40],

[44],

Lepechinia heteromorpha ^[41],

[45],

Ocimum canum

, and

Ocimum kilimandscharicum ^[42]. Likewise, (+)-β-pinene predominates over (−)-β-pinene in

[46]. Likewise, (+)-β-pinene predominates over (−)-β-pinene in

C. capitatus ^[39] as well as the

[43] as well as the

Monarda

essential oils. On the other hand, (−)-β-pinene dominates in

R. officinalis ^[40] and

[44] and

Lepechinia mutica ^[43]. The essential oils of peppermint (

[47]. The essential oils of peppermint (

Mentha

piperita

) and spearmint (

Mentha spicata) have shown nearly racemic mixtures of α- and β-pinenes ^[44]. (+)-α-Phellandrene and (−)-β-phellandrene were the dominant enantiomers in the

) have shown nearly racemic mixtures of α- and β-pinenes [48]. (+)-α-Phellandrene and (−)-β-phellandrene were the dominant enantiomers in the

Monarda

essential oils. In marked contrast, however, (−)-α-phellandrene and (+)-β-phellandrene predominated in

L. mutica essential oil ^[43]. (−)-Limonene predominates in

essential oil [47]. (−)-Limonene predominates in

M. fistulosa

essential oil, peppermint (

M. piperita

) and spearmint (

M. spicata) essential oils ^[44] whereas (+)-limonene is the major enantiomer in

) essential oils [48] whereas (+)-limonene is the major enantiomer in

C. capitatus ^[39],

[43],

O. canum

, and

O. kilimandscharicum ^[42], and a nearly racemic mixture was found in rosemary (

[46], and a nearly racemic mixture was found in rosemary (

R. officinalis) essential oil ^[40]. (+)-Linalool was the predominant enantiomer in

) essential oil [44]. (+)-Linalool was the predominant enantiomer in

C. capitatus ^[39],

[43],

Salvia schimperi ^[45],

[49],

Pycnanthemum incanum ^[46],

[50],

O. canum

, and

O. kilimandscharicum ^[42], whereas (−)-linalool was the major stereoisomer in

[46], whereas (−)-linalool was the major stereoisomer in

Lavandula angustifolia ^[47] and

[51] and

R. officinalis ^[40].

[44].