Identification of anti-HIV active dicaffeoylquinic- and tricaffeoylquinic acids in Helichrysum populifolium by NMR-based metabolomic guided fractionation

Heyman, Heino M.; Sénejoux, François; Seibert, Isabell; Klimkait, Thomas; Maharaj, Vinesh; Meyer, J.J.M.

doi:10.1016/j.fitote.2015.03.024

Cited by 57 publications

(53 citation statements)

References 24 publications

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“…The LC-MS data of the negative ionization mode, identified a caffeoylquinic acid derivative as a possible constituent in the crude methanolic extract (Table 2, Figure S2 and Figure S3). The identified mass fragment m/z 515.1223 making up the peak at 3.71 min ( Figure S4-Supplementary Data) was of particular interest since the possible compound hits included some caffeoylquinic acid derivatives which have been previously identified in other Helichrysum species, including Helichrysum italicum, Helichrysum populifolium, and Helichrysum stoechas (Barroso et al, 2014;Heyman et al, 2015;Maksimovic et al, 2017;Pereira et al, 2017). The mass fragments m/z 353.1017 and 191.0762 corresponded to previous data on Helichrysum obconicum reported by Gouveia and Castilho (2011) corresponding to some caffeoyl-quinic acid derivatives.…”

Section: Gas Chromatography-mass Spectrometry and Liquid Chromatograpmentioning

confidence: 99%

Exploring the Anti-Acne Potential of Impepho [Helichrysum odoratissimum (L.) Sweet] to Combat Cutibacterium acnes Virulence

et al. 2020

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The Gram-positive bacterium Cutibacterium acnes (previously Propionibacterium acnes), plays an important role in the pathogenesis and progression of the dermatological skin disorder acne vulgaris. The methanolic extract of Helichrysum odoratissimum (L.) Sweet (HO-MeOH) was investigated for its ability to target bacterial growth and pathogenic virulence factors associated with acne progression. The gas chromatography-mass spectrometry (GC-MS) analysis of HO-MeOH identified a-humulene (3.94%), acurcumene (3.74%), and caryophyllene (8.12%) as major constituents, which correlated with previous reports of other Helichrysum species. The HO-MeOH extract exhibited potent antimicrobial activity against C. acnes (ATCC 6919) with a minimum inhibitory concentration (MIC) of 7.81 µg/ml. It enhanced the antimicrobial activity of benzoyl peroxide (BPO). The extract showed high specificity against C. acnes cell aggregation at sub-inhibitory concentrations, preventing biofilm formation. Mature C. acnes biofilms were disrupted at a sub-inhibitory concentration of 3.91 µg/ml. At 100 µg/ml, HO-MeOH reduced interleukin-1a (IL-1a) cytokine levels in C. acnes-induced human keratinocytes (HaCaT) by 11.08%, highlighting its potential as a comedolytic agent for the treatment of comedonal acne. The extract exhibited a 50% inhibitory concentration (IC 50 ) of 157.50 µg/ ml against lipase enzyme activity, an enzyme responsible for sebum degradation, ultimately causing inflammation. The extract's anti-inflammatory activity was tested against various targets associated with inflammatory activation by the bacterium. The extract inhibited pro-inflammatory cytokine levels of IL-8 by 48.31% when compared to C. acnes-induced HaCaT cells at 7.81 µg/ml. It exhibited cyclooxygenase-II (COX-II) enzyme inhibition with an IC 50 of 22.87 µg/ml. Intracellular nitric oxide (NO) was inhibited by 40.39% at 7.81 µg/ml when compared with NO production in lipopolysaccharide (LPS)induced RAW264.7 cells. The intracellular NO inhibition was potentially due to the 2.14 fold reduction of inducible nitric oxide synthase (iNOS) gene expression. The HO-MeOH extract exhibited an IC 50 of 145.45 µg/ml against virulent hyaluronidase enzyme activity, Frontiers in Pharmacology | www.frontiersin.org January 2020 | Volume 10 | Article 1559 1 which is responsible for hyaluronan degradation and scar formation. This study provides scientific validation for the traditional use of H. odoratissimum as an ointment for pimples, not only due to its ability to control C. acnes proliferation but also due to its inhibitory activity on various targets associated with bacterial virulence leading to acne progression.

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Section: Gas Chromatography-mass Spectrometry and Liquid Chromatograpmentioning

confidence: 99%

Exploring the Anti-Acne Potential of Impepho [Helichrysum odoratissimum (L.) Sweet] to Combat Cutibacterium acnes Virulence

et al. 2020

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“…H. cymosum is mainly used as a purgative, ritual incense, and magical purposes (chase away evil spirits and rain making) and as herbal medicine for colds, cough, fever, headache, and wounds (Table 1 and Figure 1). Other minor medicinal applications include blocked nose, boost immunity, cardiovascular problems, diarrhea, dizziness, eye problems, flatulence, improve appetite, influenza, insect repellent, insomnia, kidney problems, laxative, menstrual pain, pertussis, pulmonary problems, skin infections, urinary problems, varicose veins, vomiting, and weak bones [72][73][74][75][76][77][78][79][80][81].…”

Section: Medicinal Uses Of H Cymosummentioning

confidence: 99%

Helichrysum Cymosum (L.) D.DON (Asteraceae): Medicinal Uses, Chemistry, and Biological Activities

Maroyi

2019

Asian J Pharm Clin Res

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Helichrysum cymosum is a valuable and well-known medicinal plant in tropical Africa. The current study critically reviewed the medicinal uses, phytochemistry and biological activities of H. cymosum. Information on medicinal uses, phytochemistry and biological activities of H. cymosum, was collected from multiple internet sources which included Scopus, Google Scholar, Elsevier, Science Direct, Web of Science, PubMed, SciFinder, and BMC. Additional information was gathered from pre-electronic sources such as journal articles, scientific reports, theses, books, and book chapters obtained from the University library. This study showed that H. cymosum is traditionally used as a purgative, ritual incense, and magical purposes and as herbal medicine for colds, cough, fever, headache, and wounds. Ethnopharmacological research revealed that H. cymosum extracts and compounds isolated from the species have antibacterial, antioxidant, antifungal, antiviral, anti-HIV, anti-inflammatory, antimalarial, and cytotoxicity activities. This research showed that H. cymosum is an integral part of indigenous pharmacopeia in tropical Africa, but there is lack of correlation between medicinal uses and existing pharmacological properties of the species. Therefore, future research should focus on evaluating the chemical and pharmacological properties of H. cymosum extracts and compounds isolated from the species.

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“…By analyzing and comparing the information on plants from the southern African region popularly used for HIV treatment, or tested anti-HIV activity, several compounds and compound groups have been repeatedly reported, and by evaluation of these compounds and compound groups, been classified into three distinct groups. The three groups identified are: Sufficient evidence for the antiviral activity of the phenolic acids has accumulated over the years and is still explored in many medicinal plant species (Heyman et al, 2015). Some of the dicaffeoylquinic acids (DCQAs) and the dicaffeoyltartaric acids (DCTAs) are selective inhibitors of HIV-1 IN at concentrations between 150 and 840 nM.…”

Section: Phytochemistry Of Anti-viral Componentsmentioning

confidence: 99%

Anti-HIV activity of southern African plants: Current developments, phytochemistry and future research

Prinsloo

Marokane

Street

2018

Journal of Ethnopharmacology

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An investigation of the plants from southern Africa with ethnobotanical use for the treatment of HIV, management of HIV or HIV-related symptoms, therefore provide a very good analysis of the major assays employed and the anti-viral compounds and compound groups identified. The similarity in identified anti-viral compounds worldwide should support the progression from in vitro studies to in vivo testing in development of affordable and effective anti-HIV agents for countries with high infection and mortality rates due to HIV/AIDS.

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Identification of anti-HIV active dicaffeoylquinic- and tricaffeoylquinic acids in Helichrysum populifolium by NMR-based metabolomic guided fractionation

Cited by 57 publications

References 24 publications

Exploring the Anti-Acne Potential of Impepho [Helichrysum odoratissimum (L.) Sweet] to Combat Cutibacterium acnes Virulence

Exploring the Anti-Acne Potential of Impepho [Helichrysum odoratissimum (L.) Sweet] to Combat Cutibacterium acnes Virulence

Helichrysum Cymosum (L.) D.DON (Asteraceae): Medicinal Uses, Chemistry, and Biological Activities

Anti-HIV activity of southern African plants: Current developments, phytochemistry and future research

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