New Coumarins from<i>Pilocarpus goudotianus</i>

Amaro-Luis, Juan M.; Massanet, Guillermo M.; Pando, E.; Rodríguez-Luis, Francisco; Zubı́a, Eva

doi:10.1055/s-2006-960965

Cited by 23 publications

(15 citation statements)

References 3 publications

(9 reference statements)

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“…Although studies on the isolation of secondary products from Pilocarpus sp. have been performed for a long time, the isolation of coumarins has only been reported just over a decade ago from the leaves of P. goudotianus (Amaro-Luis et al, 1990). The efficacy of the jaborandi infusions in the treatment of skin diseases such as psoriasis and vitiligo might be related with this class of natural products.…”

Section: Coumarinsmentioning

confidence: 99%

Pilocarpus spp.: a survey of its chemical constituents and biological activities

Santos¹,

Moreno²

2004

Rev. Bras. Cienc. Farm.

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Pilocarpus species have been exploited as the only source of the imidazole alkaloid pilocarpine (used in glaucoma treatment), since its isolation up to the present. Almost all Pilocarpus species are native from Brazil. Because of the medicinal importance of pilocarpine, several of them are in the path of extinction. Other secondary metabolites, such as coumarins, flavonoids and terpenes, were described for Pilocarpus species. In this review the secondary metabolites, other than pilocarpine, isolated from Pilocarpus species and their biological activities were compiled. Although the variety of structures and the importance of the biological activities described in literature for Pilocarpus species this is an unexploited field of research in Natural Products and Pharmacology.

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Section: Coumarinsmentioning

confidence: 99%

Pilocarpus spp.: a survey of its chemical constituents and biological activities

Santos¹,

Moreno²

2004

Rev. Bras. Cienc. Farm.

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“…It has been reported that coumarins with different skeletal types (furano-and pyrano-coumarins) have been isolated from the same plant species [11]. It is conceivable that the production of similarly structured constituents in the same plant is an evolutionarily advantageous response to a variety of environmental pressures that allows the plant to deter a wider spectrum of predators.…”

mentioning

confidence: 99%

Toxicity and Synergism in the Feeding Deterrence of Some Coumarins onSpodoptera frugiperdaSmith (Lepidoptera: Noctuidae)

Vera

Popich

Luna

et al. 2006

C&B

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The phagodepression activity of five coumarins (= 2H-1-benzopyran-2-ones), 6-hydroxy-7-isoprenyloxycoumarin (1), 6-methoxy-7-isoprenyloxycoumarin (2), 6,7-methylenedioxycoumarin (3), 5-methoxy-6,7-methylenedioxycoumarin (4), and 6-methoxy-7-(2-hydroxyethoxy)coumarin (5), from the Argentine native herb Pterocaulon polystachyum, was tested against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae. Two analogs, scopoletin (6) and 2-methoxy-2-methyl-3,4,5,6,7,8-hexahydro-3H-chromen-5-one (7), synthesized in our laboratory, were also evaluated for comparison. The compounds were added to an artificial diet at doses ranging from 50 to 200 microg per g of diet. Natural coumarins induced 100% of phagodepression when 200 microg were added per g of diet. Binary equimolar mixtures of the natural coumarins were phagodepressors against S. frugiperda surpassing the expected additive responses, indicating that these compounds can act synergistically against S. frugiperda larvae. Compounds 1 and 3 (non-methoxylated coumarins), and the equimolar mixture of both, displayed the strongest phagodepression. Additionally, 50 microg/g of 1 and 3 incorporated to the larval diet caused 80 and 50% of pupal mortality, respectively, while a 100 microg/g dose of compounds 2, 4, 6, and 7 produced 60, 50, 10, and 80% pupal mortality, respectively. Larval growing rate during the early larval instars was significantly reduced by treatments with the methylenedioxycoumarins 3 and 4. Coincidentally, the larval period duration was significantly increased by the latter compounds.

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“…Isopimpinellin was also indicated to have chemo-preventive effects when administered orally after skin tumour initiation by 7,12-dimethylbenz[α]anthracene (DMBA) [33]. While, alloxanthoxyletin was previously isolated from Pilocarpus goudotianus (Rutaceae) [24]. An oil derived from the flower of Melicope lunu-akenda was found to contain ecodione (38.9%), (E)-β-ocimene (12.4%), isolycodolin (11.7%) and alloevadionol (10.6%) as major constituents.…”

Section: Discussionmentioning

confidence: 99%

Alkaloid and benzopyran compounds of Melicope latifolia fruit exhibit anti-hepatitis C virus activities

Widyawaruyanti

Tanjung

Permanasari

et al. 2021

BMC Complement Med Ther

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Background New agents for developing alternative or complementary medicine to treat the hepatitis C virus (HCV) are still needed due to high rates of HCV infection globally and the current limitations of available treatments. Treatment of HCV with a combination of direct acting antivirals have been shown to be approximately 90% effective but will be limited in the future due to the emergence of drug resistance and high cost. The leaves of Melicope latifolia have previously been reported to have anti-HCV activity and are a potential source of bioactive compounds for future novel drug development. This study aimed to evaluate the efficacy of the extract of M. latifolia fruit to treat HCV and to isolate its active compounds. Method M. latifolia fruit was extracted using methanol and purified using vacuum liquid chromatography (VLC) and Radial Chromatography. The anti-HCV activity was analyzed using cell culture lines Huh7it-1 and JFH1 (genotype 2a). Time-of-addition and immunoblotting studies were performed to identify the mode of action of the isolated active compounds. The structures of the active compounds were determined using nuclear magnetic resonance (NMR) spectra, UV, IR, and Mass Spectra. Results Six known compounds were isolated from M. latifolia fruit: O-methyloktadrenolon, alloevodionol, isopimpinellin, alloxanthoxyletin, methylevodionol, and N-methylflindersine. N-methylflidersine was the most active compound with IC50 value of 3.8 μg/ml while methylevodionol, isopimpinellin, and alloevodionol were less active. O-methyloktadrenolon and alloxanthoxyletin were moderately active with IC50 values of 10.9 and 21.72 μg/ml, respectively. N-methylflidersine decreased level of HCV NS3 protein expression in the cells. Conclusion The alkaloid compound, N-methylflindersine which was isolated from M. latifolia possesses anti-HCV activity through post-entry inhibition and suppressed NS3 protein expression.

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New Coumarins fromPilocarpus goudotianus

Abstract: The leaves of PILOCARPUS GOUDOTIANUS afforded in addition to eight known coumarins three new ones, donatin, alloxanthoxyletol, and (+)-elisin. The structures were elucidated on the basis of spectroscopic evidence and chemical derivatives.

Cited by 23 publications

References 3 publications

Pilocarpus spp.: a survey of its chemical constituents and biological activities

Pilocarpus spp.: a survey of its chemical constituents and biological activities

Toxicity and Synergism in the Feeding Deterrence of Some Coumarins onSpodoptera frugiperdaSmith (Lepidoptera: Noctuidae)

Alkaloid and benzopyran compounds of Melicope latifolia fruit exhibit anti-hepatitis C virus activities

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