Casearia sylvestris Essential Oil Degradation Products Generated by Leaf Processing

Abstract

Casearia sylvestris is an endemic tree of the Latin America that the essential oil (EO) has anti‐inflammatory and gastroprotective actions. This study evaluates the chemical composition of the EO from the volatile fractions of in natura, fresh, and dried C. sylvestris var. sylvestris and var. lingua leaves. For both varieties, the dried leaves presented higher EO yield as compared to fresh leaves. The major EO chemical components were (E)‐caryophyllene, α‐humulene, germacrene D, bicyclogermacrene, spathulenol, caryophyllene oxide, and humulene epoxide II. In both varieties, the content of sesquiterpene hydrocarbons decreased and oxygenated sesquiterpenes increased on going from in natura to fresh and dried leaves, which indicated that leaf drying and hydrodistillation modified the volatile composition. The results also suggested that bicyclogermacrene and (E)‐caryophyllene were oxidized during processing, to generate spathulenol and caryophyllene oxide, respectively. C. sylvestris varieties and in natura, fresh, and dried leaves differed in terms of the chemical composition of volatiles, which could affect the EO biological activities.

In Vitro Schistosomicidal Activities of the Leaf Extracts from Casearia sylvestris Varieties

“…sylvestris leaf extract cannot be associated with the presence of casearin‐like diterpenes only. Other compounds, such as sesquiterpenes from the essential oil, [33] which was previously extracted from the dried leaves of the same specimens in 1.4 % yield (w/w) [34] can be responsible for the schistosomicidal activity alone or even acting in synergism with the casearin‐like diterpenes or other minor chemical components in the extract.…”

“…The plates were incubated under the same conditions mentioned above and visually evaluated every 24 h for 72 h; inverted optical microscope (Primo Vert Microscope, Carl Zeiss) was used (4 to 10× magnification). Alterations were scored on the basis of a viability scale (0 to 3), where 3 refers to normal activity, 2 refers to slower activity, 1 refers to minimal activity, and 0 refers to worm death according to Ramirez et al [34,39] . and [40].…”

Casearia Essential Oil: An Updated Review on the Chemistry and Pharmacological Activities

“…These reactions turned the sesquiterpenes hydrocarbons (E)-caryophyllene (5), α-humulene (6), bicyclogermacrene (1), and δ-cadinene (7) into oxygenated sesquiterpenes such as humulene epoxide II (8), caryophyllene oxide (4), spathulenol (3), viridiflorol, globulol (9), maaliol, and α-cadinol, thus increasing the oxygenated sesquiterpenes content. [20,35,[41][42][43] The most commonly detected sesquiterpenes hydrocarbons in the EOs of Casearia species are (E)-caryophyllene (5), bicyclogermacrene (1), germacrene D (2), germacrene B (10), αzingiberene (11), α-humulene (6), β-elemene (12), γ-elemene (13), γ-muurolene (14), β-acoradiene (15), δ-cadinene (7), and α-copaene (16) (Scheme 1 and Table 4), whereas spathulenol (3), humulene epoxide II (8), caryophyllene oxide (4), and globulol (9) are the main oxygenated sesquiterpenes. The main compounds derive from germacryl -germacrenes A and D, elemenes, muurolenes, α-copaene (16), α-selinene, bicyclogermacrene (1), spathulenol (3), among others -and humulyl cations -α-humulene (6), humulene epoxide II (8), (E)caryophyllene (5), and caryophyllene oxide (4), which are [20] 1.4 (0.4) [a] 4 Cerrado 12/16 Carvalho et al [16] [15] 0.4 (0.2) [a] 4.5 Atlantic Forest 02/12 Amaral et al [23] 1.2 2 -2014 Pereira et al [24] (0.2) [a] 5 Atlantic Forest 10/12 Bou et al [25] 0.6-1.1…”

“…1 [b] Atlantic Forest 01-09/00 Castellani et al [26] 0.6-0.9 4 C. sylvestris 'lingua' Cerrado 07 and 12/16 Carvalho et al [5] 0.9 (0.3) [a] 4 Cerrado 12/16 Carvalho et al [16] [29] Sousa et al [30] 2.5 4 --Esteves et al [14] 0.2 2 C. arborea --Pereira et al [31] 0.06 5 C. tomentosa Forest Dehradun (India) -Tyagi et al [13] 0.02 [a] 2 C. lasiophylla --Salvador et al [12] 0.2 [a] 2 C. decandra -08/06 Stefanello et al [32] 0.1 [a] -C. grandiflora Amazon Forest 12/92 Morais et al [33] [a] Values in parentheses refer to fresh leaves; [20] SA Population Carvalho et al [20] Thermal Desorption Carvalho et al [35] Carvalho et al [35] Spósito et al [21] Moreira et al [22] Carvalho et al [15] Amaral et al [23] Pereira et al [36] Pereira et al [24] Pereira et al [37] Pereira et al [38] Bou et al [25] Tininis et al [39] δ-elemene [20] SA Population Carvalho et al [20] Thermal Desorption Carvalho et al [35] Carvalho et al [35] Spósito et al [21] Moreira et al [22] Carvalho et al [15] Amaral et al [23] Pereira et al [36] Pereira et al [24] Pereira et al [37] Pereira et al [38] Bou et al [25]...…”

“…[12,[28][29][30] These compounds have been detected only in the EO from C. sylvestris, C. lasiophylla, and C. tomentosa (Scheme 2). The monoterpenes include α-pinene (17) (2.0- Thermal Desorption Carvalho et al [35] Carvalho et al [35] Winter [40] Autumn [40] Summer [40] Spring [40] Silva et al [28] Sousa et al [30] Schneider et al [29] Esteves et al [14] C. arborea [31] Pereira et al [31] C. tomentosa [13] C. lasiophylla [12] Salvador et al [12] C. decandra [32] Stefanello et al [32] C. grandiflora [33] Morais et al [33] Oxygenated sesquiterpenes 97.9 8.9 [c] 87.6 89.2…”