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

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].

Plants 10 00482 g001 550
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 [11,12]. Consistent with these reports, a floral essential oil of 

 in two old reports [7][8]. 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%) [13][9]
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%) [14][10]
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%) [15][11]
M. citriodora var. citriodora Leaves Liverpool, UK (cultivated) Thymol (50.7%), p-cymene (22.8%), carvacrol (3.6%) [16][12]
M. citriodora var. citriodora Flowers Liverpool, UK (cultivated) Thymol (61.8%), γ-terpinene (13.3%), p-cymene (4.2%), carvacrol (3.8%) [16][12]
M. citriodora var. citriodora Aerial parts Liverpool, UK (cultivated) Thymol (56.9%), p-cymene (13.0%), α-terpinene (10.0%), carvacrol (4.3%) [17][13]
M. citriodora var. citriodora Aerial parts Commercial (unknown) Thymol (70.6%), p-cymene (10.6%), carvacrol (6.1%) [18][14]
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%) [19][15]
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%) [20][16]
M. fistulosa Aerial parts Saint-Jean-sur-Richelieu, QC, Canada (cultivated) Geraniol (61.8%), geranyl formate (16.6%), geranial (10.6%), neral (6.6%) [21][17]
M. fistulosa Aerial parts Poplarville, MS, USA (cultivated) Carvacrol (39.1%), p-cymene (35.4%), (−)-1-octen-3-ol [22][18]
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%) [23][19]
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%) [24][20]
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%) [24][20]
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%) [25][21]
M. fistulosa Aerial parts Chişinău, Republic of Moldova (cultivated) Carvacrol (54.8%), p-cymene (23.2%), carvacrol methyl ether (5.9%) [26][22]
M. fistulosa Flowers Gallatin Valley, MT, USA (wild) Carvacrol (45.7%), p-cymene (25.6%), γ-terpinen (6.8%), thymol (3.1%) [27][23]
M. fistulosa Leaves Gallatin Valley, MT, USA (wild) Carvacrol (71.5%), p-cymene (13.1%), γ-terpinen (2.5%), thymol (3.3%) [27][23]
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%) [28][24]
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%) [29][25]
M. punctata Flowers Xi’an, China (cultivated?) Thymol (75.2%), p-cymene (6.7%), limonene (5.4%), carvacrol (3.5%) [30][26]
a Isomer not indicated.

The high concentrations of thymol, carvacrol, and 

p

-cymene are consistent with the traditional uses of 

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

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

p-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].

-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].

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 [43], 

 [39], 

Rosmarinus officinalis [44], 

 [40], 

Lepechinia heteromorpha [45], 

 [41], 

Ocimum canum

, and 

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

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

C. capitatus [43] as well as the 

 [39] as well as the 

Monarda

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

R. officinalis [44] and 

 [40] and 

Lepechinia mutica [47]. The essential oils of peppermint (

 [43]. The essential oils of peppermint (

Mentha

 × 

piperita

) and spearmint (

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

) have shown nearly racemic mixtures of α- and β-pinenes [44]. (+)-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 [47]. (−)-Limonene predominates in 

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

M. fistulosa

 essential oil, peppermint (

M. piperita

) and spearmint (

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

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

C. capitatus [43], 

 [39], 

O. canum

, and 

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

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

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

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

C. capitatus [43], 

 [39], 

Salvia schimperi [49], 

 [45], 

Pycnanthemum incanum [50], 

 [46], 

O. canum

, and 

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

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

Lavandula angustifolia [51] and 

 [47] and 

R. officinalis [44].

 [40].

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