Ocotea quixos, American cinnamon

doi:10.1016/0378-8741(81)90038-6

Journal of Ethnopharmacology

Volume 4, Issue 2, September 1981, Pages 233-236

https://doi.org/10.1016/0378-8741(81)90038-6 Get rights and content

Abstract

Among the three South American Lauraceae with cinnamon odours, Ocotea quixos Lam. is distinguished with the richest historical legacy. Cinnamaldehyde, its odoriferous principle, occurs besides o-methoxycinnamaldehyde, cinnamic acid and methyl cinnamate in the fruit calyx. In contradistinction, 1-nitro-2-phenylethane is responsible for the cinnamon odour of bark and leaves of Aniba canelilla (H.B.K.) Mez and Ocotea pretiosa (Nees) Mez.

References (19)

O.R. Gottlieb et al.
A further study on the reaction of 1-nitro-2-phenylethane with alkali
Chemistry and Industry
(1963)
B. Cobo
Historia del Nuevo Mundo
(1891)
P.J. de Arriaga
La extirpación de la idolatróa en el Perú
P. de Villagomes
Exortaciones y instrucción acerca de las idolatrías: del arzobispado de Lima
A. Ducke
Lauráceas aromáticas da Amazônia Brasileirião
Anais da Primeira Reunião Sul-Americana de Botânica (Rio de Janeiro)
(1938)
G. Fernandes de OviedoG. Fernandes de Oviedo
F. Gonzalez Suarez
Historia del Ecuador
(1969)
O.R. Gottlieb et al.
Occurrence of 1-nitro-2-phenylethane in Ocotea pretiosa and Aniba canelilla
Journal of Organic Chemistry
(1959)
O.R. Gottlieb et al.
Essential oil of the bark and wood of Aniba canelilla
Perfumery and Essential Oil Record
(1960)

There are more references available in the full text version of this article.

Cited by (30)

Essential oils from Ocotea species: Chemical variety, biological activities and geographic availability
2022, Fitoterapia
Citation Excerpt :
Its flavoring property motivated its addition to drinks used in rituals. Nowadays the species Ocotea quixos continues to be a product of great value, being used not only in traditional medicine as an appetizer, eupeptic, antidiarrheal, disinfectant, and local anesthetic, but also as a condiment [4]. Another historical event that demonstrates the importance of the genus Ocotea, the South American cinnamon, refers to the account of Ludwig Riedel, who arrived in Brazil in 1821, invited to participate in the expedition organized by the German-Russian explorer Baron von Langsdorff.
This review describes the chemical composition and biological properties of essential oils from plants of the Ocotea genus, from different origin. This taxon belongs to the Laureaceae family, which in turn, is best known for medicinal use, often related to the essential oils. The text includes studies about Ocotea species distributed mainly on the South American continent, but also reporting species located in North America and Africa. Brazil, Colombia, Costa Rica and Ecuador are countries with highest number of species mentioned in the review. Also, the major components of each essential oil, its chemical structures, as well as the description and extent of biological activities related to essential oils are detailed in this review. Finally, the text discusses the chemical and biological aspects of these studies in a comparatively way, also informing additional data such as yield, biome of origin and pharmacobotanical location.
Molecular modifications on β-nitro-styrene derivatives increase their antioxidant capacities
2021, Journal of Molecular Structure
Citation Excerpt :
The 1-nitro-2-phenylethane or nitro-phenylethane is an odoriferous compound responsible for the cinnamon scent like cinnamaldehyde, found on Aniba canelilla (H.B.K.) Mez [1].
β-Nitro-styrenes among other nitroderivatives are known due to their high electrophilicity and low electron donation capacities. A preferential molecular modification on 1-nitro-2-phenylethene was analyzed by DFT method in B3LYP/6-311++G(2d,2p) level of theory on gas phase seeking to increase its electron donating capacity. For this, four molecular modifications were proposed showing the impact of alkene moiety, substitutions on β or para positions using electron donating groups (EDGs) or electron withdrawing groups (EWGs). The para is the preferential position for methylation when compared to ortho or meta positions. Our results show that EDGs increase the redox capacity in β and para positions and decrease the electrophilicity when compared to EWGs. The increase on electron donation capacity is in accordance with DPPH evaluation and β-nitro-phenylethene derivatives still are poor antioxidants. Therefore, the antioxidant capacity on β-nitro-phenylethene can be increased by using EDGs substituted on β or para positions.
Chemical composition and antimicrobial activity of Myrcianthes fragrans essential oil, a natural aromatizer of the traditional Ecuadorian beverage colada morada
2018, Journal of Ethnopharmacology
Citation Excerpt :
For example; in the Northern Sierra of the country (Pichincha, Chimborazo, Imbabura, Cotopaxi, Cañar, Tungurahua and other places), the leaves of M. halli are used (Gallardo de la Puente, 2014; Ulloa, 2006), while in the Province of Loja, the leaves of M. fragrans are used. In other places of Ecuador such as in the Pichincha province (Quito), people add another native Ecuadorian aromatic spice called ishpingo (Ocotea quixos), that is collected in the Amazonian region, and was highly appreciated even by the Incas as a medicine and as a spice (Naranjo et al., 1981). The presence of “arrayan” in various sites of the Loja Province (Southern Ecuador) is documented in several botanical registers of Ecuador, including the Loja Herbarium of the Universidad Nacional de Loja (UNL), the Herbarium of the Universidad Técnica Particular de Loja (HUTPL), the Herbarium Nacional del Ecuador (QCNE), the Herbarium of the Universidad Católica (QCA), the Herbarium of the Escuela Politécnica del Chimborazo (ESPOCH), and the Azuay Herbarium of the Universidad del Azuay (UDA).
The importance given in Ecuador to the rescue of traditional knowledge and nutritional value of ancestral foods and drinks, has stimulated our investigation of the chemical composition and some biological activities of M. fragrans (‘arrayán’) essential oil, a natural aromatic additive used in the preparation of the traditional fruit-juice ‘colada morada’, which is typically drunk in the Day of the Dead or All Soul´s Day.
Different essential oils of Myrcianthes fragrans (Sw.) McVaught were obtained by hydrodistillation of the aerial parts of the plant collected in Cerro Villonaco (Loja-Ecuador) at three different phenological growth stages, i.e., during foliation (Fo), flowering (Fl) and fruiting (Fr) stages. The chemical compositions of the essential oils were determined by GC/MS and GC/FID techniques. The antimicrobial activities were determined by the broth microdilution method and reported as minimal inhibitory concentration (MIC, ug/mL).
i) to investigate the traditional uses of arrayán (M. fragrans) in the South region of Ecuador; ii) to identify the main components of the essential oils isolated at different phenological stages; iiì) to test the antimicrobial activity of the essential oils against bacteria and yeasts causing human ailments and a yeast causing food spoilage.
37, 46 and 38 compounds, representing 96.5%, 96.2%, and 95.6% of the three essential oils (Fo, Fl and Fr), respectively, have been identified. Oxygenated monoterpenes (OM) were the major components with percentages of 63.1 (Fo), 49.4 (Fl), and 61.9% (Fr), respectively. The main constituents of the essential oils were the monoterpene aldehydes geranial (1) and neral (2), the content of which varied, depending on the phenological development stage of the plant, spanning from 31.1% and 23.6% (Fo), to 23.6% and 17.8% (Fl), and 29.7% and 24.3% (Fr), respectively. In vitro antimicrobial tests showed that the essential oils from M. fragrans exhibited good activity against the Gram-negative bacteria, K. pneumoniae, and against the yeasts, C. albicans and S. cerevisiae.
The oil is characterized by a high concentration of the monoterpene aldehydes geranial and neral (citral), that make the aroma of colada morada prepared in southern Ecuador quite different from the beverage made in other regions of the country, where other types of myrtles (Myrtaceae spp.) are used. Moreover, the oil may become a new rich source of the important industrial chemical citral. The pleasant aromatic properties and the good in vitro antimicrobial activity of arrayán oil suggest a plausible scientific explanation for the traditional uses of the plant not only as a natural aromatizer of a traditional beverage but also as a natural anti-infective and anti-yeast agent.
Vasorelaxant effects of 1-nitro-2-phenylethane, the main constituent of the essential oil of Aniba canelilla, in superior mesenteric arteries from spontaneously hypertensive rats
2013, European Journal of Pharmaceutical Sciences
Citation Excerpt :
Aniba elliptica A. C. Sm., Cryptocarya canelilla Kunth], (Lauraceae) is an aromatic plant abundant in the Amazon region, where it is commonly known as “casca-preciosa” (precious bark). This plant is an important and historically interesting species in the Amazon forest because it was confused with cinnamon trees (Cinnamomum zeylanicum Blume) during the 1540 voyage of Pizarro and Orellana from the Andes to the Amazon estuary and during Humbolt and Bonpland’s 1800 expedition in the Orinoco River basin to find the “famous cinnamon” (Naranjo and Kijjoa, 1981). The trunk wood, fine stems and leaves of casca-preciosa are used as spices and ingredients for local dishes, fragrances, and sachets.
The present study investigated the mechanisms underlying the vasorelaxant effects of the essential oil of Aniba canelilla (EOAC) and its main constituent 1-nitro-2-phenylethane (NP) in isolated superior mesenteric artery from spontaneously hypertensive rats (SHRs). At 0.1–1000 μg/mL, EOAC and NP relaxed SMA preparations pre-contracted with 75 mM KCl with IC₅₀ (geometric mean [95% confidence interval]) values of 294.19 [158.20–94.64] and 501.27 [378.60–624.00] μg/mL, respectively); or with phenylephrine (PHE) (IC₅₀s = 11.07 [6.40–15.68] and 7.91 [4.08–11.74) μg/mL, respectively). All these effects were reversible and remained unaltered by vascular endothelium removal. In preparations maintained under Ca²⁺-free conditions, EOAC and NP (both at 600 μg/mL) reduced the PHE-, but not the caffeine-induced contraction. In Ca²⁺-free and high K⁺ (75 mM) medium, the contractions produced by CaCl₂ or BaCl₂ were reduced or even abolished by EOAC and NP at 100 and 600 μg/mL, respectively. EOAC and NP (both at 10–1000 μg/mL) also relaxed the contraction evoked by phorbol dibutyrate (IC₅₀ = 52.66 [10.82–94.64] and 39.13 [31.55–46.72] μg/mL, respectively). It is concluded that NP has a myogenic endothelium-independent vasorelaxant effects and appears to be the active principle of the EOAC. Vasorelaxant effect induced by both EOAC and NP is preferential to receptor-activated pathways and it appears to occur intracellularly more than a superficial action restricted to the membrane environment such as a simple blocking activity on a given receptor or ion channel.
1-Nitro-2-phenylethane, the main constituent of the essential oil of Aniba canelilla, elicits a vago-vagal bradycardiac and depressor reflex in normotensive rats
2010, European Journal of Pharmacology
Previously, it was shown that intravenous (i.v.) treatment with the essential oil of Aniba canelilla (EOAC) elicited a hypotensive response that is due to active vascular relaxation rather than to the withdrawal of sympathetic tone. The present study investigated mechanisms underlying the cardiovascular responses to 1-nitro-2-phenylethane, the main constituent of the EOAC. In pentobarbital-anesthetized normotensive rats, 1-nitro-2-phenylethane (1–10 mg/kg, i.v.) elicited dose-dependent hypotensive and bradycardiac effects which were characterized in two periods (phases 1 and 2). The first rapid component (phase 1) evoked by 1-nitro-2-phenylethane (10 mg/kg) was fully abolished by bilateral vagotomy, perineural treatment of both cervical vagus nerves with capsaicin (250 µg/ml) and was absent after left ventricle injection. However, pretreatment with capsazepine (1 mg/kg, i.v.) or ondansetron (30 µg/kg, i.v.) did not alter phase 1 of the cardiovascular responses to 1-nitro-2-phenylethane (10 mg/kg, i.v.). In conscious rats, 1-nitro-2-phenylethane (1–10 mg/kg, i.v.) evoked rapid hypotensive and bradycardiac (phase 1) effects that were fully abolished by methylatropine (1 mg/kg, i.v.). It is concluded that 1-nitro-2-phenylethane induces a vago-vagal bradycardiac and depressor reflex (phase 1) that apparently results from the stimulation of vagal pulmonary rather than cardiac C-fiber afferents. The transduction mechanism of the 1-nitro-2-phenylethane excitation of C-fiber endings is not fully understood and does not appear to involve activation of either Vanilloid TPRV₁ or 5-HT₃ receptors. The phase 2 hypotensive response to 1-nitro-2-phenylethane seems to result, at least in part, from a direct vasodilatory effect since 1-nitro-2-phenylethane (1–300 µg/ml) induced a concentration-dependent reduction of phenylephrine-induced contraction in rat endothelium-containing aorta preparations.
Antinociceptive activity of 1-nitro-2-phenylethane, the main component of Aniba canelilla essential oil
2009, Phytomedicine
Aniba canelilla (H.B.K.) Mez is a medicinal plant used in the Amazon folk therapeutic as antispasmodic, antidiarreic, carminative, tonic agent and a stimulant of the digestive and central nervous system. Our preliminary studies showed that the plant essential oil has analgesic activity in mice. Now, we are reporting the antinociceptive effect of the compound 1-nitro-2-phenylethane (97.5%), the main component of the essential oil of Aniba canelilla, which was obtained by column chromatographic purification. In the writhing test this compound was dosed at 15, 25 and 50 mg/kg reducing the abdominal writhes in a significant manner; in the hot plate test it was assayed at 50, 100 and 200 mg/kg producing no alterations in the latency time when compared to the control; and in the formalin test the 1-nitro-2-phenylethane was tested at 50 and 25 mg/kg decreasing significantly the second phase of the algic stimulous. The study suggests that the 1-nitro-2-phenylethane has analgesic activity, probably of peripheral origin. The mechanism involved is not completely understood, however, the results suggest that the opiod receptors are involved in the antinociceptive action observed to 1-nitro-phenylethane.

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Journal of Ethnopharmacology

Abstract

References (19)

A further study on the reaction of 1-nitro-2-phenylethane with alkali

Chemistry and Industry

Historia del Nuevo Mundo

La extirpación de la idolatróa en el Perú

Exortaciones y instrucción acerca de las idolatrías: del arzobispado de Lima

Lauráceas aromáticas da Amazônia Brasileirião

Anais da Primeira Reunião Sul-Americana de Botânica (Rio de Janeiro)

Historia del Ecuador

Occurrence of 1-nitro-2-phenylethane in Ocotea pretiosa and Aniba canelilla

Journal of Organic Chemistry

Essential oil of the bark and wood of Aniba canelilla

Perfumery and Essential Oil Record

Cited by (30)

Essential oils from Ocotea species: Chemical variety, biological activities and geographic availability

Molecular modifications on β-nitro-styrene derivatives increase their antioxidant capacities

Chemical composition and antimicrobial activity of Myrcianthes fragrans essential oil, a natural aromatizer of the traditional Ecuadorian beverage colada morada

Vasorelaxant effects of 1-nitro-2-phenylethane, the main constituent of the essential oil of Aniba canelilla, in superior mesenteric arteries from spontaneously hypertensive rats

1-Nitro-2-phenylethane, the main constituent of the essential oil of Aniba canelilla, elicits a vago-vagal bradycardiac and depressor reflex in normotensive rats

Antinociceptive activity of 1-nitro-2-phenylethane, the main component of Aniba canelilla essential oil

Short communicationOcotea quixos, American cinnamon

Abstract

Chemistry and Industry

Historia del Nuevo Mundo

La extirpación de la idolatróa en el Perú

Exortaciones y instrucción acerca de las idolatrías: del arzobispado de Lima

Lauráceas aromáticas da Amazônia Brasileirião

Anais da Primeira Reunião Sul-Americana de Botânica (Rio de Janeiro)

Historia del Ecuador

Occurrence of 1-nitro-2-phenylethane in Ocotea pretiosa and Aniba canelilla

Journal of Organic Chemistry

Essential oil of the bark and wood of Aniba canelilla

Perfumery and Essential Oil Record

Short communication
Ocotea quixos, American cinnamon