Two new 7-dehydroaporphine alkaloids and antiplatelet action aporphines from the leaves of Annona purpurea

Chang, Fang Rong; Wei, Jia; Teng, Che-Ming; Wu, Yang Chang

doi:10.1016/s0031-9422(98)00376-8

Cited by 44 publications

(30 citation statements)

References 14 publications

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“…In concordance with the above statement, the AC of some aporphine alkaloids isolated from the leaves of Annona purpurea [22][23][24][25] is somewhat unclear, as they are represented as R or S even though they were isolated from the same plant [24,25] and their specific rotation was not described, or in some cases the same compound is reported as dextro-or levo-rotatory [23][24][25] Accordingly, it was considered relevant to use vibrational circular dichroism (VCD) as a reliable alternative to assign the AC of aporphine alkaloids. This method has demonstrated great efficiency in the assignment of the AC of many natural products [26][27][28] although few alkaloids were studied using this approach.…”

supporting

confidence: 64%

“…The back-conversion of norpurpurein hydrochloride (3) to norpurpureine (2), showed again dextrorotatory specific rotation. From these results it could be inferred that the intrinsic levorotatory optical rotation (OR) of 3 might be confused with (-)-2 reported from A. purpurea [23]. This finding shows that the AC assignment of aporphine alkaloids should not be based only on its OR [10], since it has been shown that OR is not always a reliable tool for the AC assignments [19][20][21].…”

mentioning

confidence: 95%

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Configurational Study of an Aporphine Alkaloid from Annona purpurea

Ontiveros-Rodríguez

Burgueño‐Tapia

Porras-Ramírez

et al. 2018

Natural Product Communications

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Purpureine (1), norpurpureine (2), and 3-hydroxyglaucine (4) were isolated from the leaves of Annona purpurea. A vibrational circular dichroism study for the absolute configuration determination of 1 provides evidence for the mutually dependent atropisomerism, local chirality of the sole stereogenic center, and the geometry of the tetrahedral nitrogen atom in aporphine alkaloids. The observed change in the optical rotation sign between 2 and its hydrochloride 3 might explain why this compound has been reported as dextrorotatory and levorotatory from the same botanical source. Furthermore, 1 H and 13 C NMR spectra of 1, 2 and 4 were fully assigned for the first time.

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supporting

confidence: 64%

mentioning

confidence: 95%

Configurational Study of an Aporphine Alkaloid from Annona purpurea

Ontiveros-Rodríguez

Burgueño‐Tapia

Porras-Ramírez

et al. 2018

Natural Product Communications

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“…Also, 7-hydroxydehydrothalicsimidine was found to be strongly active against platelet aggregation induced by thrombin, PAF, collagen, and AA. 22 Therefore, isoquinoline alkaloid 5 and several others were also assayed for thrombin activity inhibition, which catalyzes the conversion of fibrinogen to fibrin. None of the alkaloids tested were inhibitory.…”

Section: Resultsmentioning

confidence: 99%

The Alkaloids of Artabotrys uncinatus

et al. 2001

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A novel type of alpha,beta-butenolide alkaloid, uncinine (1), two novel oxoaporphines, artabonatine C (2) and artabonatine D (3), a new oxazoloaporphine, artabonatine E (4), and a new 7,7'-bisdehydroaporphine, artabonatine F (5), along with 25 known alkaloids, were isolated from Artabotrys uncinatus. The structures of 1-5 were determined using NMR and mass spectral data. Atherospermidine and squamolone exhibited cytotoxicity against hepatocarcinoma cancer cell lines (Hep G(2) and 2,2,15), and the activity of some of the alkaloids in an antithrombin assay is also discussed.

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“…A literature survey for biological activity of 3 and 5 showed that 3 reverses a multidrug resistance phenotype and possessed weak cytotoxicity (You et al, 1995), mutagenicity (Nozaka et al, 1990), a relaxant effect (Chulia et al, 1995) and an inhibitory activity for CD45 protein tyrosine phosphatase (Miski et al, 1995), however 5 inhibited platelet aggregation (Chang, Wei, Teng, & Wu, 1998) and had a sedative effect (Han, Park, & Park, 1989).…”

Section: Resultsmentioning

confidence: 99%

Constituents of Nelumbo nucifera leaves and their antimalarial and antifungal activity

Agnihotri

ElSohly

Khan

et al. 2008

Phytochemistry Letters

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From the leaves of Nelumbo nucifera (an aquatic plant), one new compound, 24(R)-ethylcholest-6-ene-5α-ol-3-O-β-D-glucopyranoside (1), along with 11 known metabolites (2-12), were isolated and identified by spectroscopic methods including 1D-and 2D NMR. Antifungal activity for (R)-roemerine (3) (IC 50 /MIC = 4.5/10 μg/mL against Candida albicans) and antimalarial activity for (R)-roemerine (3) and N-methylasimilobine (5) (IC 50 = 0.2 and 4.8 μg/mL for the D6 clone, respectively, and 0.4 and 4.8 μg/mL for the W2 clone, respectively) was observed. None of the compounds were cytotoxic to Vero cells up to a concentration of 23.8 μg/mL. NMR data for 10-eicosanol (7) and 7,11,15-trimethyl-2-hexadecanone (10) are presented for the first time. An analysis of the structure-activity relationship shows that the substituents in position C-1 and C-2 of aporphine alkaloids are crucial for the antimalarial activity.

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Two new 7-dehydroaporphine alkaloids and antiplatelet action aporphines from the leaves of Annona purpurea

Cited by 44 publications

References 14 publications

Configurational Study of an Aporphine Alkaloid from Annona purpurea

Configurational Study of an Aporphine Alkaloid from Annona purpurea

The Alkaloids of Artabotrys uncinatus

Constituents of Nelumbo nucifera leaves and their antimalarial and antifungal activity

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