Hyperforin Analogues from St. John's Wort (<i>Hypericum perforatum</i>)

Verotta, Luisellá; Appendino, Giovanni; Jakupovic, Jasmin; Bombardelli, Ezio

doi:10.1021/np9903752

Cited by 114 publications

(82 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The NMR data of 8 (Supplementary Data) was very similar to that of propolone D (7) [30], except for the resonances of H-23, C-23, C-24, and C-24 geminal methyls. These observations indicated that 7 and 8 differ only in the replacement of the tertiary hydroxyl at C24 with a hydroperoxyl group [31].…”

Section: Studies Of Nemorosone Degradation Using Hplc-esi-ms Nmentioning

confidence: 92%

Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry

Piccinelli

Campone

Piaz

et al. 2009

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

Nemorosone is a polycyclic polyisoprenylated benzophenone (PPBs) with strong cytotoxic activity. It is the major constituent of Clusia rosea floral resin and brown Cuban propolis. Other PPBs found in Cuban propolis are oxidized and cyclized derivatives of nemorosone. The instability of PPBs carrying an enolizable 1,3-diketone system has been suggested, and the elucidation of this aspect is very fundamental for the evaluation of their biologic activity. Electrospray ionization multistage tandem mass spectrometry (ESI-MS n ) was employed to shed light on the origin of these derivatives of nemorosone and to define the stability of this natural product. For this purpose, we initially performed MS n experiments on seven related PPBs to obtain useful information for structural characterization of this class of compounds and to identify the degradation products of nemorosone. The proposed fragmentation pathways, supported by exact mass measurements, allowed the nature of side chains on the bicyclo core and the type and position of their modifications to be established. In a second part, the degradation profile of nemorosone under different conditions was investigated to assess the possible effects of isolation procedures, climatic, and storage conditions on its stability. Our results reveal that nemorosone undergoes rapid degradation in n-hexane and chloroform solutions. The degradation products, identified by HPLC-ESI/MS n and NMR, are identical to derivatives of nemorosone previously isolated from propolis and plants. Thus, these PPBs are artefacts formed predominantly during the extraction and purification procedures. (J Am Soc

show abstract

Section: Studies Of Nemorosone Degradation Using Hplc-esi-ms Nmentioning

confidence: 92%

Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry

Piccinelli

Campone

Piaz

et al. 2009

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

show abstract

“…Hyperforin (2.0 to 4.5 %), adhyperforin (0.2 to 1.9 %) (Brondz et al 1982 ;Ollivier et al 1985 ;Ayuga & Rebuelta 1986 ;American Herbal Pharmacopeia 1997), oxygenated analogues of hyperforin (Trifunovic et al 1998 ;Verotta et al 1999Verotta et al , 2000.…”

Section: Prenylated Phloroglucinolsmentioning

confidence: 99%

“…It has now emerged that hyperforin (Figure 1) is one of the major constituents responsible for antidepressant activity, although further research is required to determine which other constituents contribute to the antidepressant effect. As hyperforin is unstable (Verotta et al 2000), standardising products on hyperforin content is problematic.…”

Section: Commentmentioning

confidence: 99%

St John's wort (Hypericum perforatum L.): a review of its chemistry, pharmacology and clinical properties

Barnes

Anderson

Phillipson

2001

Journal of Pharmacy and Pharmacology

674

462

View full text Add to dashboard Cite

The chemical composition of St. John's wort has been well-studied. Documented pharmacological activities, including antidepressant, antiviral, and antibacterial effects, provide supporting evidence for several of the traditional uses stated for St John's wort. Many pharmacological activities appear to be attributable to hypericin and to the flavonoid constituents ; hypericin is also reported to be responsible for the photosensitive reactions that have been documented for St. John's wort. With regard to the antidepressant effects of St John's wort, hyperforin, rather than hypericin as originally thought, has emerged as one of the major constituents responsible for antidepressant activity. Further research is required to determine which other constituents contribute to the antidepressant effect.Evidence from randomised controlled trials has confirmed the efficacy of St John's wort extracts over placebo in the treatment of mild-to-moderately severe depression. Other randomised controlled studies have provided some evidence that St John's wort extracts are as effective as some standard antidepressants in mild-to-moderate depression. There is still a need for further trials to assess the efficacy of St John's wort extracts, compared with that of standard antidepressants, particularly newer antidepressant agents, such as the selective serotonin reuptake inhibitors (recent comparative studies with fluoxetine and sertraline have been conducted). Also, there is a need for further studies in well-defined groups of patients, in different types of depression, and conducted over longer periods in order to determine longterm safety. St John's wort does appear to have a more favourable short-term safety profile than do standard antidepressants, a factor that is likely to be important in patients continuing to take medication.Concerns have been raised over interactions between St John's wort and certain prescribed medicines (including warfarin, ciclosporin, theophylline, digoxin, HIV protease inhibitors, anticonvulsants, selective serotonin reuptake inhibitors, triptans, oral contraceptives) ; advice is that patients taking these medicines should stop taking St John's wort, generally after seeking professional advice as dose adjustment of conventional treatment may be necessary.

show abstract

“…Do extrato da erva-de-São-João (Hypericum perforatum), foi isolada a hipericina (50), utilizada como antidepressivo. Aparentemente, as propriedades atribuídas a este extrato devem-se à hiperforina (51), que compreende uma mistura de tautômeros (Figura 10) 13,23 . Outra substância natural de origem oriental que apresenta originalidade e complexidade estruturais capazes de inspirar novos fármacos úteis para tratamento da malária, importante doença tropical negligenciada, é a artemisinina (52, Figura 11), importante protótipo-natural antimalárico, isolado de Artemisia annua, planta muito conhecida e utilizada na medicina chinesa 24,25 .…”

Section: O Ressurgimento Dos Produtos Naturais Como Fonte De Novos Fáunclassified

Os produtos naturais e a química medicinal moderna

Viegas¹,

Bolzani²,

Barreiro³

2006

Quím. Nova

158

View full text Add to dashboard Cite

Recebido em 10/12/04; aceito em 29/6/05; publicado na web em 20/1/06 THE NATURAL PRODUCTS AND THE MODERN MEDICINAL CHEMISTRY. Natural products have been utilized by humans since ancient times and the relief and cure of their diseases was the first purpose for using natural products in medicine. The history of the oriental and occidental civilizations is very rich in examples of the utilization of natural products in medicine and health care. Chinese traditional medicine is one of the most important examples of how natural products can be efficient in the treatment of diseases, and it points to the importance of scientific research on natural products, concerning the discovery of new active chemical entities. The complexity, chemical diversity and biological properties of natural products always fascinated people, and during the last 200 years, this led to the discovery of important new drugs. In the last 30 years, the development of new bioassay techniques, biotechnology methods, bio-guided phytochemical studies, automated high throughput screening and high performance analytical methods, have introduced new concepts and possibilities of rational drug design and drug discovery. In this context, natural products have played an important and decisive role in the development of modern medicinal chemistry.Keywords: medicinal chemistry; natural products; drug design. INTRODUÇÃOOs produtos naturais são utilizados pela humanidade desde tempos imemoriais. A busca por alívio e cura de doenças pela ingestão de ervas e folhas talvez tenha sido uma das primeiras formas de utilização dos produtos naturais. A história do desenvolvimento das civilizações Oriental e Ocidental é rica em exemplos da utilização de recursos naturais na medicina, no controle de pragas e em mecanismos de defesa, merecendo destaque a civilização Egípcia, Greco-romana e Chinesa. A medicina tradicional chinesa desenvolveu-se com tal grandiosidade e eficiência que até hoje muitas espécies e preparados vegetais medicinais são estudados na busca pelo entendimento de seu mecanismo de ação e no isolamento dos princípios ativos.As técnicas desenvolvidas e utilizadas no Egito para conservação de múmias ainda são um desafio para a Química moderna. Na Idade Antiga, além de técnicas medicinais, muitos venenos foram descobertos na natureza e utilizados para fins de defesa, caça e mesmo ilícitos, como a utilização do veneno de Hemlock (Conium maculatum) na execução de prisioneiros, inclusive Sócrates, durante o Império Grego 1,2 . A natureza sempre despertou no homem um fascínio encantador, não só pelos recursos oferecidos para sua alimentação e manutenção, mas por ser sua principal fonte de inspiração e aprendizado. A busca incessante pela compreensão das leis naturais e o desafio de transpor barreiras à sua sobrevivência, como o clima e as doenças, levaram o homem ao atual estágio de desenvolvimento científico, mesmo após o avanço tecnológico observado nos dias de hoje. BREVE HISTÓRICO DO PAPEL DOS PRODUTOS NATURAIS NA DESCOBERTA DE FÁRMACOSVárias civilizações in...

show abstract

Hyperforin Analogues from St. John's Wort (Hypericum perforatum)

Abstract: Three oxygenated analogues of the prenylated phloroglucinol hyperforin (3-5) were isolated from the aerial parts of Hypericum perforatum and their structures elucidated by spectroscopic methods.

Cited by 114 publications

References 9 publications

Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry

Fragmentation pathways of polycyclic polyisoprenylated benzophenones and degradation profile of nemorosone by multiple-stage tandem mass spectrometry

St John's wort (Hypericum perforatum L.): a review of its chemistry, pharmacology and clinical properties

Os produtos naturais e a química medicinal moderna

Contact Info

Product

Resources

About