Anti-Mycobacterium tuberculosis activity of essential oil and 6,7-dehydroroyleanone isolated from leaves of Tetradenia riparia (Hochst.) Codd (Lamiaceae)

Baldin, Vanessa Pietrowski; Scodro, Regiane Bertin de Lima; Lopes-Ortiz, Mariana Aparecida; Almeida, Aryadne Larissa de; Gazim, Zilda Cristiani; Ferarrese, Letícia; Faiões, Viviane dos Santos; Torres-Santos, Eduardo Caio; Pires, Cláudia Terêncio Agostinho; Caleffi-Ferracioli, Katiany Rizzieri; Siqueira, Vera Lúcia Dias; Cortez, Diógenes Aparı́cio Garcia; Cardoso, Rosilene Fressatti

doi:10.1016/j.phymed.2018.04.043

Cited by 39 publications

(32 citation statements)

References 28 publications

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“…Concerning chemical constituents, some terpenes have already had their antimycobacterial activity evaluated. Isoprenes, such as monoterpenes, sesquiterpenes and related alcohols and phenols, have been responsible for antimycobacterial activity of EOs (Baldin et al 2018). It should be emphasized that the promising antitubercular activity of EOs from S. odoratissima may be attributed to β-caryophyllene, a terpene whose favorable biological activity has already been described in the literature, mainly its antioxidant, antitumor and antimicrobial properties (Dahham et al 2015).…”

Section: Discussionmentioning

confidence: 98%

Bioactivities of essential oils from different parts of Spiranthera odoratissima (Rutaceae)

et al. 2020

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This paper aims to investigate, for the first time, in vitro antitubercular, antileishmanial and antiproliferative activities of essential oils (EOs) from S. odoratissima leaves and flowers - grown in midwestern Brazil - against Mycobacterium tuberculosis, promastigote forms of Leishmania amazonensis and human tumor cell lines. Antimycobacterial activity of EOs was evaluated in terms of the minimal inhibitory concentration (MIC). EOs from leaves and flowers showed to be active antimicrobials against M. tuberculosis, since MIC values were 150 µg/mL and 162.5 µg/mL, respectively. Both EOs exhibited significant activity against promastigote forms of L. amazonensis; IC50 values (50% growth inhibition) were 14.36 ± 2.02 (EOs from leaves) and 19.89 ± 2.66 µg/mL (EOs from flowers). Antiproliferative activity in normal (GM07492A, lung fibroblasts) and tumor (MCF-7, HeLa and M059J) cell lines was performed by the XTT assay; results were expressed as IC50 (50% cell growth inhibition) and the selective index was calculated. IC50 values of EOs from leaves and flowers obtained in normal cell lines for were 502.97 ± 40.33 µg/mL and 370.60 ± 2.01 µg/mL, respectively. Antiproliferative activity was observed against human tumor cell lines, whose IC50 values were significantly lower than those obtained in normal cell lines of MCF-7 cells (367.57 ± 4.46 µg/mL-EOs from leaves and 357.70 ± 1.85 µg/mL-EOs from flowers) and M059J cells (492.53 ± 56.67 µg/mL-EOs from leaves and 324.90 ± 6.72 µg/mL-EOs from flowers), thus, indicating selectivity. These in vitro results showed that EOs from S. odoratissima may be an antimycobacterial, antiparasitic and antitumor agent.

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Section: Discussionmentioning

confidence: 98%

Bioactivities of essential oils from different parts of Spiranthera odoratissima (Rutaceae)

et al. 2020

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“…The HMBC spectrum allowed us to place the chlorinated side chain and the rearranged methyl group at the correct positions by selected Leishmanicidal activity of (2) and 3Recently, activity against Mycobacterium tuberculosis, Leishmania amazonensis, Staphylococcus aureus and Caenorrhabditis elegans was demonstrated for the essential oil from T. riparia and some of its isolated constituents. 3,[14][15][16][17] Here, we evaluated the activity of 7α-hydroxyroyleanone (1), extracted from T. riparia leaves and the product of its dehydration reaction (2), against Leishmania amazonensis, a parasite that can cause different clinical disease manifestations such as cutaneous leishmaniasis, which may evolve to the severe anergic diffuse cutaneous disease, and the visceral leishmaniasis as well. [18][19][20][21] Our results demonstrated that the diterpenequinone (1) exhibits a dose dependent anti-Leishmania promastigote activity with half maximal inhibitory concentration (IC 50 ) of 2.96 μg mL -1 ( Table 2).…”

Section: Structural Identification Of (2)mentioning

confidence: 99%

“…2 The plant is used as a remedy against a wide range of diseases including malaria, angina, gastroenteritis, diarrhea, influenza, respiratory problems and symptoms such as headaches, fever, stomachaches, etc. 3,4 Studies have shown that extracts of leaves of T. riparia as well as its essential oil exhibited antimicrobial activities against bacteria and fungi such as Mycobacterium tuberculosis, M. smegmatis, M. simiae, Staphylococcus aureus and Candida albicans. 3 The diterpenequinone 7α-hydroxyroyleanone, also known as horminone, 5 was shown to be one of the active compounds against tuberculosis (TB).…”

Section: Introductionmentioning

confidence: 99%

“…3,4 Studies have shown that extracts of leaves of T. riparia as well as its essential oil exhibited antimicrobial activities against bacteria and fungi such as Mycobacterium tuberculosis, M. smegmatis, M. simiae, Staphylococcus aureus and Candida albicans. 3 The diterpenequinone 7α-hydroxyroyleanone, also known as horminone, 5 was shown to be one of the active compounds against tuberculosis (TB). 4,6 It also displays activity against T. cruzi, the Chagas' disease parasite.…”

Section: Introductionmentioning

confidence: 99%

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Unexpected Rearrangement and Aromatization on Dehydration Reaction of the Bioactive Diterpenequinone 7α-Hydroxyroyleanone

Leitão¹,

Pinheiro²,

Rezende³

et al. 2020

J. Braz. Chem. Soc.

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7α-Hydroxyroyleanone is a bioactive diterpene isolated from leaves of Tetradenia riparia, active against tuberculosis and T. cruzi. In order to use this compound as starting material for the synthesis of compounds with enhanced bioactivity we aimed the dehydration of the 7-alpha-hydroxyl group of royleanone. The reaction performed in acetic acid and hydrochloric acid under reflux gave an unexpected chlorinated naphtoquinone, with aromatization and opening of one of the rings of the starting material, as major product, besides 6,7-dehydroroyleanone and a complex mixture of other products. The reaction products were purified by high-speed countercurrent chromatography with hexane-acetonitrile 1:1. Compounds were tested for their anti-leishmanial activity (L. amazonensis) pointing out a potential leishmanicidal agent which may favor the development of more effective therapies.

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“…The recent investigation demonstrated that essential oil isolated from leaves of Tetradenia riparia and the pure compound 6,7-dehydroroyleanone display good activity against Mycobacterium tuberculosis clinical isolates, including MDR isolates, with low cytotoxicity to murine macrophages. The 6,7-dehydroroyleanone compound is a potential candidate for anti-TB drug (BALDIN et al, 2018).…”

Section: Natural Products From Aromatic and Medical Plants As Antimicmentioning

confidence: 99%

A review on antibiotic resistance: Origin and mechanisms of bacterial resistance as biological phenomenon

2018

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Antimicrobial resistance is a natural biological phenomenon in their struggle for existence and represents a major health care issue, associated with high mortality and morbidity. The first cases of mass emergence of resistant strains were observed in the middle of the 20th century, and since then cases of resistance have been reported all over the world, and in the last two decades even more frequently are reported multiple bacterial resistance. Factors that contribute to the development of bacteria resistance are abuse in the use of antibacterial agents, in humans or livestock, and releases of antibacterial agents into the environment. Moreover, the development of new effective antibiotics is decreasing, contrary to increasing the overall effort for the synthesis of new ones. Identification and reporting of bacterial resistance, as well as monitoring of the use of antibiotics in the outpatient and inpatient setting, today is the obligation of all countries.

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Anti-Mycobacterium tuberculosis activity of essential oil and 6,7-dehydroroyleanone isolated from leaves of Tetradenia riparia (Hochst.) Codd (Lamiaceae)

Cited by 39 publications

References 28 publications

Bioactivities of essential oils from different parts of Spiranthera odoratissima (Rutaceae)

Bioactivities of essential oils from different parts of Spiranthera odoratissima (Rutaceae)

Unexpected Rearrangement and Aromatization on Dehydration Reaction of the Bioactive Diterpenequinone 7α-Hydroxyroyleanone

A review on antibiotic resistance: Origin and mechanisms of bacterial resistance as biological phenomenon

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