Isolation and Identification of Antifungal and Antialgal Alkaloids from<i>Haplophyllum sieversii</i>

Cantrell, Charles L.; Schrader, Kevin K.; Mamonov, Leonid K.; Sitpayeva, Gulnara; Kustova, Tatyana S.; Dunbar, Cynthia E.; Wedge, David E.

doi:10.1021/jf051478v

Cited by 90 publications

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References 29 publications

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“…Optical rotation was measured on a Polartronic-E Schmidt-Haensch polarimeter in CHCl 3 . IR spectra (KBr or neat) were recorded on a Perkin-Elmer, Panagon 500 Fourier transform (FT)-IR spectrometer.…”

Section: Methodsmentioning

confidence: 99%

“…1D-NMR spectra for this compound was found to be very similar to that for 2, being solely differentiated by the absence of an H-3 hydrogen at quinolone moiety being replaced by a C-C bond between the piridinone ring and further aromatic ring, which was confirmed by a key HMBC correlation between H-5Ј (d H 7.52-7.43, m, 1H) and C-3 (d H 129.8). The structure of 3 was thus determined to be 6-methylbenzofuro[2,3-b]quinolin-4(1H)-one (hepta- (3). Although the structure of 3 has been described since 1980 as being a synthetic product, 22) the occurrence of 3 is presented herein as being a natural product, including full spectroscopic data analysis for the first time.…”

Section: )mentioning

confidence: 97%

“…3) Leishmaniasis is an endemic disease which affects nearly 12 million people worldwide in tropical and subtropical regions. 4) Clinically, the disease compromises skin, mucosa, and/or visceral organs and its specific action depends on both the species involved and the host's immunological system.…”

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confidence: 99%

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seco-Limonoids and Quinoline Alkaloids from Raputia heptaphylla and Their Antileishmanial Activity

Barrera

Coy-Barrera

Granados-Falla

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleThe Rutaceae family, consisting of ca. 150 genera and 1600 species, is mostly distributed throughout tropical regions. Species from this family have important uses in industry such as in food, pharmaceuticals and ornamental purposes, as well as having a wide variety of ethnobotanical uses 1) ; they are studied in terms of obtaining alkaloids and limonoids as bioactive principles.2) Among important plants from Rutaceae, those from the Raputia genus have attracted special attention because of their use in South-America due to their trypanocidal and leishmanicidal properties. 3)Leishmaniasis is an endemic disease which affects nearly 12 million people worldwide in tropical and subtropical regions.4) Clinically, the disease compromises skin, mucosa, and/or visceral organs and its specific action depends on both the species involved and the host's immunological system. Cutaneous and mucocutaneous varieties are often disabling, having high morbidity rates, whereas the visceral type affects a smaller number of people.5) More than 98% cases in Colombia are caused by cutaneous Leishmaniasis, being mostly transmitted by Leishmania (Viannia) panamensis (L. (V.) panamensis) species. 6) At clinical level, 20% of cases are neither reported nor treated; furthermore, nearly 80% of infections are spontaneously resolved due to the host's immunological response against parasites.7) Clinical cases which cannot be immunologically resolved are often treated by first-line drugs (e.g. pentavalent antimonial salts) which have shown higher toxicity and parasite-induced resistance. This had consequently led to the search and development of novel therapeutic agents for controlling this disease. Hence, studying the active principles obtained from traditional medicinal plants still has special importance.8) As part of our research into bioactive compounds from Rutaceae plants, this article thus describes the isolation, elucidation and antileishmanial activity of a novel seco-limonoid (1) and two novel alkaloids (2-3), along with other six known compounds [a seco-limonoid (4) and five alkaloids (5-9)] obtained from Raputia heptaphylla stem bark and leaves. The antileishmanial effect of isolated compounds was evaluated on L. (V.) panamensis (promastigotes and amastigotes). Compounds 1 and 5 revealed important antileishmanial activity at different levels. Results and DiscussionEthanol extract from R. heptaphylla (20 g) stem bark was subjected to an ultrasound-assisted acid-base extraction for alkaloids 9,10) affording an alkaloid extract (1.2 g). Chloroform-soluble extract was purified by repeated CC on silica gel to give compounds 1-4. Alkaloids 5-9 were also isolated using an identical procedure on ethanol extract from R. heptaphylla leaves (50 g). Structures were established on the basis of full spectroscopic data analysis compared to data from the pertinent literature (Fig. 1).Compound 1 was obtained as colorless crystals (mp 220-222°C, MeOH). Its high resolution-electrospray ionization mass spectra (HR-ESI-MS) showed a pseud...

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Section: Methodsmentioning

confidence: 99%

Section: )mentioning

confidence: 97%

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seco-Limonoids and Quinoline Alkaloids from Raputia heptaphylla and Their Antileishmanial Activity

Barrera

Coy-Barrera

Granados-Falla

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Recently, haplamine that was isolated from Haplophyllum sieversii, a plant endemic to Kazakhstan, was found to possess selective toxicity towards certain cyanobacterial species including O. perornata. 5 In this study, we present the additional discoveries of anti-algal compounds from other plants found primarily in the Republic of Kazakhstan.…”

Section: Introductionmentioning

confidence: 99%

Bioassay-guided isolation of anti-algal constituents from Inula helenium and Limonium myrianthum

Cantrell¹,

Mamonov²,

Ryabushkina³

et al. 2006

Arkivoc

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Over 70 crude plant extracts, primarily from Kazakhstan, were screened against the freshwater phytoplanktons Oscillatoria perornata and Selenastrum capricornutum. Extracts from Limonium myrianthum and Inula helenium both demonstrated selective inhibition against the odorproducing cyanobacterium O. perornata compared to activity against the green alga S. capricornutum. Bioassay-guided fractionation of the L. myrianthum dichloromethane extract resulted in the identification of nepodin, torachrysone, chrysophanol, and physcion. Nepodin demonstrated the desired selective inhibition with lowest-complete-inhibition concentration values of 100 µg/mL and >100 µg/mL towards O. perornata and S. capricornutum, respectively. Similarly, chrysophanol also demonstrated the desired selective inhibition with lowest-completeinhibition concentration values of 10 µg/mL and >100 µg/mL, respectively. Bioassay-guided fractionation of the I. helenium hexane extract resulted in the isolation of alantolactone, isoalantolactone, and 11αH,13-dihydroisoalantolactone. Activities of these three isolated constituents as well as those of synthetic isomers are reported.

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“…Eudesmin negatively affected the growth of Oscillatoria perornata at 3.86 mg/L and Selenastrum capricornutum at 38.6 mg/L, thereby showing the higher susceptibility of O. perornata. As a contrast, eudesmin exerted no effect on Oscillatoria agardhii even at 38.6 mg/L [136].…”

Section: Polyphenolsmentioning

confidence: 78%

Effect of Lignocellulose Related Compounds on Microalgae Growth and Product Biosynthesis: A Review

et al. 2014

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Microalgae contain valuable compounds that can be harnessed for industrial applications. Lignocellulose biomass is a plant material containing in abundance organic substances such as carbohydrates, phenolics, organic acids and other secondary compounds. As growth of microalgae on organic substances was confirmed during heterotrophic and mixotrophic cultivation, lignocellulose derived compounds can become a feedstock to cultivate microalgae and produce target compounds. In this review, different treatment methods to hydrolyse lignocellulose into organic substrates are presented first. Secondly, the effect of lignocellulosic hydrolysates, organic substances typically present in lignocellulosic hydrolysates, as well as minor co-products, on growth and accumulation of target compounds in microalgae cultures is described. Finally, the possibilities of using lignocellulose hydrolysates as a common feedstock for microalgae cultures are evaluated.Keywords: lignocellulose; hydrolysis; microalgae; cultivation; extraction; bioproducts OPEN ACCESSEnergies 2014, 7 4447 Microalgae: A Source of Valuable CompoundsMicroalgae include several groups of microorganisms that belong to the Prokaryota or Eukaryota, typically found in fresh water or marine systems in single cell forms or in groups. They are capable of performing photosynthesis, producing approximately half of the atmospheric oxygen while using the greenhouse gas carbon dioxide to grow photoautotrophically [1]. Microalgae contain valuable compounds such as lipids, proteins and pigments (Table 1) which have substantial potential for commercial applications. Microalgae cells accumulate lipids which include triacylglycerides (TAGs), polyunsaturated fatty acids (PUFAs) and sterols [2]. These lipids constitute storage materials or membrane structural components in microalgae and can be used for biofuel, food supplement and pharmaceutical production. Indeed, fossil fuels are nowadays still the main source of carbon based fuels, the exploitation of which causes emission of greenhouse CO 2 . Biodiesel production from oil crops is seen as currently the best alternative, but still presents the main drawback of competing with food production for arable land. Therefore, production of biodiesel from TAGs present in microalgae can become an environmentally friendly alternative as microalgae produce oil and fix CO 2 from atmosphere without the necessity of implementing vast arable areas for cultivation [3]. On the other hand, consumption of PUFAs in the human diet can help prevent the development of cardiovascular and mental diseases [4]. Fish are a rich source of PUFAs, but uncontrolled fishing has led to a substantial decrease in the worldwide fish population [5]. Production of PUFAs from microalgae may overcome this problem. On the other hand, sterols from microalgae are important part of the diet for juvenile scallops or prawns in aquaculture hatcheries [6]. Moreover, the high protein content in microalgae makes them a possible fodder for agricultural livestock [7]. In ad...

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Isolation and Identification of Antifungal and Antialgal Alkaloids fromHaplophyllum sieversii

Cited by 90 publications

References 29 publications

seco-Limonoids and Quinoline Alkaloids from Raputia heptaphylla and Their Antileishmanial Activity

seco-Limonoids and Quinoline Alkaloids from Raputia heptaphylla and Their Antileishmanial Activity

Bioassay-guided isolation of anti-algal constituents from Inula helenium and Limonium myrianthum

Effect of Lignocellulose Related Compounds on Microalgae Growth and Product Biosynthesis: A Review

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