Isolation, Chemical Profile and Antimalarial Activities of Bioactive Compounds from Rauvolfia caffra Sond

Tlhapi, Dorcas B.; Ramaite, Isaiah D. I.; Anokwuru, Chinedu P.; Taglialatela‐Scafati, Orazio; Hoppe, Heinrich C.

doi:10.3390/molecules24010039

Cited by 12 publications

(8 citation statements)

References 23 publications

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“…1 H-NMR (400 MHz, CD 3 OD): δ H 4.7 (1H, s, 29a-H), 4.6 (1H, s, 29b-H), 3.18 (1H, m, 3-H), 2.38 (1H, m, 19-H), 1.91 (1H, m, 21-H), 1.70 (3H, s, 30-H), 1.60 (1H, m, 2-H), 1.39 (1H, m, 18-H), 1.30 (1H, m, 9-H), 1.04 (3H, s, C 26-H), 1.0 (3H, s, 23-H), 0.97 (3H, s, 27-H), 0.86 (3H, s, 25-H), 0.77 (3H, s, 24-H) ppm. 13 C-NMR (100 MHz, CD 3 OD): δ C 150.95 (C-20), 108.54 (C-29), 78.27 (C-3), 55.48 (C-5), 50.64 (C-9), 49.16 (C-18), 42.17 (C-14), 40.53 (C-8), 38.67 (C-4), 38.54 (C-1), 38.17 (C-13), 37.00 (C-10), 36.91 (C-16), 34.21 (C-7), 30.43 (C-21), 29.52 (C-23), 29.27 (C-2), 27.19 (C-15), 25.54 (C-12), 22.79 (C-11), 20.70 (C-30), 18.17 (C-6), 18.03 (C-28), 15.32 (C-26), 14.69 (C-24), 13.67 (C-27) ppm ( Figures S1–S6 [ 21 , 25 ]).…”

Section: Methodsmentioning

confidence: 99%

“…1 H-NMR (400 MHz, CD 3 OD): δ H 7.11 (1H, d, J = 8.6 Hz, 12-H), 6.77 (1H, d, J = 2.0 Hz, 9-H), 6.68 (1H, dd, J = 8.9, 2.2 Hz, 11-H), 5.59 (1H, q, J = 6.8 Hz, 19-H), 4.41 (1H, d AB, J = 15.6 Hz, 21-H α ), 4.16 (1H, d AB, J = 15.6 Hz, 21-H β ), 3.48 (2H, d, J = 7.2 Hz, 17-H), 3.28 (3H, s, N-CH 3 ), 3.15 (1H, dd, J = 12.4, 4.8 Hz, 6-H β ), 3.0 (3H, s, N + -CH 3 ), 2.95 (1H, dd, J = 2.0, 10.4 Hz, 15-H), 2.9 (1H, d, J = 15.2 Hz, 6-H α ), 2.4 (1H, dd, J = 11.6, 10.8 Hz, 14-H α ), 2.12-2.0 (2H, m, 16-H + 14-H β ), 1.82 (s, OH), 1.63 (3H, d, J = 6.7 Hz, 18-H) ppm. 13 C-NMR (100 MHz, CD 3 OD): δ C 150.91 (C-10), 132.10 (C-20), 131.68 (C-13), 127.67 (C-8), 126.83 (C-2), 120.72 (C-19), 112.34 (C-12), 111.75 (C-11), 102.14 (C-9), 99.77 (C-7), 65.45 (C-5), 64.39 (C-17), 62.40 (C-21), 61.07 (C-3), 43.63 (C-16), 32.01 (C-14), 26.01 (C-15), 23.87 (C-6), 11.57 (C-18) ppm ( Figures S13–S16 [ 21 , 27 ]).…”

Section: Methodsmentioning

confidence: 99%

“…HRMS [M] + : m / z 325.1912; calcd. for C 20 H 25 N 2 O 2 + : 325.1911 ( Figures S17–S21 [ 21 , 27 ]).…”

Section: Methodsmentioning

confidence: 99%

“…In our continuing search for biologically active metabolites of traditional medicinal plants from the Venda area in South Africa, we investigated Rauvolfia caffra , which is widely used in medicine in Sub-Sahara African communities to treat a range of ailments such as toothaches, hysteria, epilepsy, eye diseases, skin wounds, urticaria, severe abdominal pains, diarrhoea, headaches, constipation, irregular periods, swollen legs, palpitation of the heart, insomnia, insecurity, restlessness, anxiety and earache [ 15 , 16 , 17 , 18 , 19 , 20 ]. Previously, we isolated three indole alkaloids (raucaffricine, N -methylsarpagine and spegatrine) and one terpenoid (lupeol) from the stem bark of Rauvolfia caffra and found that the major constituents do not contribute to the antiplasmodial activity of R. caffra [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

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In Vitro Studies on Antioxidant and Anti-Parasitic Activities of Compounds Isolated from Rauvolfia caffra Sond

et al. 2020

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As part of an ongoing study of natural products from local medicinal plants, the methanol extract of stem bark of Rauvolfia caffra Sond was investigated for biological activity. Column chromatography and preparative thin-layer chromatography were used to isolate lupeol (1), raucaffricine (2), N-methylsarpagine (3), and spegatrine (4). The crude extract, fractions and isolated compounds were tested for anti-oxidant, antitrypanosomal and anti-proliferation activities. Two fractions displayed high DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical scavenging activity and reducing power with IC50 (The half maximal inhibitory concentration) and IC0.5 values of 0.022 ± 0.003 mg/mL and 0.036 ± 0.007 mg/mL, and 0.518 ± 0.044 mg/mL and 1.076 ± 0.136 mg/mL, respectively. Spegatrine (4) was identified as the main antioxidant compound in R. caffra with IC50 and IC0.5 values of 0.119 ± 0.067 mg/mL and 0.712 ± 0 mg/mL, respectively. One fraction displayed high antitrypanosomal activity with an IC50 value of 18.50 μg/mL. However, the major constituent of this fraction, raucaffricine (2), was not active. The crude extract, fractions and pure compounds did not display any cytotoxic effect at a concentration of 50 μg/mL against HeLa cells. This study shows directions for further in vitro studies on the antioxidant and antitrypanosomal activities of Rauvolfia caffra Sond.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…HRMS [M] + : m / z 325.1912; calcd. for C 20 H 25 N 2 O 2 + : 325.1911 ( Figures S17–S21 [ 21 , 27 ]).…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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In Vitro Studies on Antioxidant and Anti-Parasitic Activities of Compounds Isolated from Rauvolfia caffra Sond

et al. 2020

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“… 39 Psidium guajava guava Eugenol Raja et al., 2015 40 Pycnanthus angolensis Akomu Pycnantolol, lignans (–)-dihydroguaiaretic acid, heliobuphthalmin, talaumidin, hinokinin, the labdanetype diterpene ozic acid, and the steroids stigmast-4-en-6β-ol-3-one, β-sitosterol and stigmasterol Abrantes et al., 2008 41. Rauvolfia vomitoria asofeyeje raucaffricine Tlhapi et al., 2019 42. Senna podocarpa 1,2-benzenedicarboxylic acid, mono (2-ethylhexyl) ester phthalate (26.6%) and β-elemene (27.9%).…”

Section: Medicinal Plants With Pharmacological and Biological Action mentioning

confidence: 99%

A systematic review on COVID-19 pandemic with special emphasis on curative potentials of Nigeria based medicinal plants

Oladele¹,

Ajayi

Oyeleke³

et al. 2020

Heliyon

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Despite the frightening mortality rate associated with COVID-19, there is no known approved drug to effectively combat the pandemic. COVID-19 clinical manifestations include fever, fatigue, cough, shortness of breath, and other complications. At present, there is no known effective treatment or vaccine that can mitigate/inhibit SARS-CoV-2. Available clinical intervention for COVID-19 is only palliative and limited to support. Thus, there is an exigent need for effective and non-invasive treatment. This article evaluates the possible mechanism of actions of SARS-CoV-2 and present Nigeria based medicinal plants which have pharmacological and biological activities that can mitigate the hallmarks of the pathogenesis of COVID-19. SARS-CoV-2 mode of actions includes hyper-inflammation characterized by a severe and fatal hyper-cytokinaemia with multi-organ failure; immunosuppression; reduction of angiotensin-converting enzyme 2 (ACE2) to enhance pulmonary vascular permeability causing damage to the alveoli; and further activated by open reading frame (ORF)3a, ORF3b, and ORF7a via c-Jun N- terminal kinase (JNK) pathway which induces lung damage. These mechanisms of action of SARS-CoV-2 can be mitigated by a combination therapy of medicinal herbs based on their pharmacological activities. Since the clinical manifestations of COVID-19 are multifactorial with co-morbidities, we strongly recommend the use of combined therapy such that two or more herbs with specific therapeutic actions are administered to combat the mediators of the disease.

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Natural indole‐containing alkaloids and their antibacterial activities

Liu

Cui

et al. 2020

Archiv der Pharmazie

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As the growth in resistance to bacterial infection treatments poses a grave threat to global health in the 21st century, there is a constant need to explore novel antibacterial agents that have the ability to overcome drug resistance. Indole-containing alkaloids are widely distributed in nature, and a variety of indole-containing alkaloids have already been applied in clinical practice, proving that indole-containing alkaloids are fascinating and privileged scaffolds for the development of novel drugs. Moreover, indole

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Isolation, Chemical Profile and Antimalarial Activities of Bioactive Compounds from Rauvolfia caffra Sond

Cited by 12 publications

References 23 publications

In Vitro Studies on Antioxidant and Anti-Parasitic Activities of Compounds Isolated from Rauvolfia caffra Sond

In Vitro Studies on Antioxidant and Anti-Parasitic Activities of Compounds Isolated from Rauvolfia caffra Sond

A systematic review on COVID-19 pandemic with special emphasis on curative potentials of Nigeria based medicinal plants

Natural indole‐containing alkaloids and their antibacterial activities

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