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
Monarda
Monarda citriodora
Monarda fistulosa
Monarda punctata
Figure 1.
Monarda species discussed in this work (photographs by S. K. L).
Several
Monarda
M. fistulosa
Monarda punctata
Monarda citriodora
andM. 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 (). The essential oils ofM. 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 ). The essential oils ofM. fistulosa
(samples #1 and #2) in this study fit into the thymol-rich chemotype. Interestingly, there was a high concentration of thymoquinone inM. fistulosa
sample #3, with concomitant lower concentrations of thymol and carvacrol. Thymol was reported as the major component ofM. 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 ofM. punctata
from China was rich in thymol (75.2%), which is in agreement with the aerial parts essential oils from Alabama.Table 4.
Monarda
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.
p
-cymene are consistent with the traditional uses ofMonarda 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], andp-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 ofMonarda
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 inMonarda
essential oils, (+)-α-pinene was the major enantiomer found inCoridothymus capitatus [39],
[43],Rosmarinus officinalis [40],
[44],Lepechinia heteromorpha [41],
[45],Ocimum canum
, andOcimum kilimandscharicum [42]. Likewise, (+)-β-pinene predominates over (−)-β-pinene in
[46]. Likewise, (+)-β-pinene predominates over (−)-β-pinene inC. capitatus [39] as well as the
[43] as well as theMonarda
essential oils. On the other hand, (−)-β-pinene dominates inR. officinalis [40] and
[44] andLepechinia 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 theMonarda
essential oils. In marked contrast, however, (−)-α-phellandrene and (+)-β-phellandrene predominated inL. mutica essential oil [43]. (−)-Limonene predominates in
essential oil [47]. (−)-Limonene predominates inM. 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 inC. capitatus [39],
[43],O. canum
, andO. 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 inC. capitatus [39],
[43],Salvia schimperi [45],
[49],Pycnanthemum incanum [46],
[50],O. canum
, andO. kilimandscharicum [42], whereas (−)-linalool was the major stereoisomer in
[46], whereas (−)-linalool was the major stereoisomer inLavandula angustifolia [47] and
[51] andR. officinalis [40].
[44].