Antifungal anthraquinones from Morinda lucida

Rath, Guido; Ndonzao, Menavanza; Hostettmann, Kurt

doi:10.3109/13880209509055208

Cited by 72 publications

(45 citation statements)

References 15 publications

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“…Natural AQs are characterized by a large structural variety and exhibit very diverse effects with broad pharmacological activities and low toxicity (Müller 2000). They possess anti-inflammatory, antiviral (Semple et al 2001;Schinazi et al 1990), antimicrobial (Izhaki 2002), antifungal (Chrysayi-Tokousbalides and Kastanias 2003Rath et al 1995), antimalarial (Sittie et al 1999, hypotensive, analgetic (Younos et al 1990), antioxidant (Tripathi et al 1997), moderate antitumor, cytostatic (Gálvez et al 1996), antileukemic, andmutagenic (Ismail et al 1997), astringent, and purgative effects (Bruneton 1999). Another important feature of naturally produced AQs is their great biotechnological potential.…”

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confidence: 99%

Hydroxylated anthraquinones produced by Geosmithia species

et al. 2009

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Geosmithia fungi are little known symbionts of bark beetles. Secondary metabolites of lilac colored species G. lavendula and other nine Geosmithia species were investigated in order to elucidate their possible role in the interactions of the fungi with environment. Hydroxylated anthraquinones (yellow, orange, and red pigments), were found to be the most abundant compounds produced into the medium during the submerged cultivation. Three main compounds were identified as 1,3,6,8-tetrahydroxyanthraquinone (1), rhodolamprometrin (1-acetyl-2,4,5,7-tetrahydroxyanthraquinone; 2), and 1-acetyl-2,4,5,7,8-pentahydroxyanthraquinone (3). Compounds 2 and 3 (representing the majority of produced metabolites) inhibited the growth of G+-bacteria Staphylococcus aureus and Bacillus subtilis with minimum inhibitory concentration of 64-512 microg/mL. Anti-inflammatory activity detected as inhibition of cyclooxygenase-2 was found only for compound 3 at 1 and 10 microg/mL. Compound 2 interfered with the morphology, compound 3 with cell-cycle dynamics of adherent mammalian cell lines.

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confidence: 99%

Hydroxylated anthraquinones produced by Geosmithia species

et al. 2009

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“…Compounds 3-8 were found to be 2-methyl anthraquinone (tectoquinone) (3), 24,25 maritinone (4), 26,27 elliptinone (5), 28,29 plumbagin (6), 27,30 (+)-cis-isoshinanolone (7), 26,31 and ethylidene-6,6′-biplumbagin (8) 32,33 by comparison of their NMR and MS data with those in the literature. The relative configuration of cis-isoshinanolone (7) was supported by the small coupling constant observed between H-3 and H-4 (J = 2.8 Hz); cis and trans isomers show significantly different coupling constants (cis: J = 2.5 Hz; trans: J = 7.5 Hz).…”

Section: Resultsmentioning

confidence: 98%

Synergistic trail sensitizers from Barleria alluaudii and Diospyros maritima

Whitson¹,

Hui²,

Thomas³

et al. 2012

Planta Med

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Barleria alluaudii and Diospyros maritima were both investigated as part of an ongoing search for synergistic TRAIL (tumor necrosis factor-α-related apoptosis-inducing ligand) sensitizers. As a result of this study, two naphthoquinone epoxides, 2,3-epoxy-2,3-dihydrolapachol (1) and 2,3-epoxy-2,3-dihydro-8-hydroxylapachol (2), both not previously isolated from natural sources, and the known 2-methyl anthraquinone (3) were identified from B. alluaudii. Time-dependent density functional theory (TD-DFT) calculations of electronic circular dichroism (ECD) spectra were utilized to establish the absolute configuration of 1 and 2. Additionally, five known naphthoquinone derivatives, maritinone (4), elliptinone (5), plumbagin (6), (+)-cis-isoshinanolone (7), and ethylidene-6,6′-biplumbagin (8) were isolated from D. maritima. Compounds 1, 2, and 4-6 showed varying levels of synergy with TRAIL. Maritinone (4) and elliptinone (5) showed the highest synergistic effect, with more than a three-fold increase in activity observed with TRAIL than with compound alone.Tumor necrosis factor-α-related apoptosis-inducing ligand (TRAIL/Apo2L) is a member of the tumor necrosis factor (TNF) family of apoptosis triggering proteins. 1 TRAIL promotes recruitment of the adaptor protein FADD (Fas associated death domain) upon binding to death domain-containing transmembrane receptors, death receptors 4 and 5 (DR4, DR5). FADD is responsible for recruiting procaspase-8 and procaspase-10, which results in the formation of a trimerized receptor-ligand complex called DISC (death-inducing signaling complex). The activated initiator caspase-8 then activates effector caspase-3, caspase-6, and caspase-7, which triggers the caspase cascade and subsequently results in apoptosis. 2,3 In type I cancer cells, caspase-8 can directly activate downstream effector caspases to promote apoptosis. However, in type II cancer cells, apoptosis proceeds through cross-talk between # Dedicated to Dr. Gordon M. Cragg, formerly of the National Cancer Institute, Frederick, Maryland, for his pioneering work on the development of natural product anticancer agents. * Corresponding Author: Tel: (301) 846-1943. Fax: (301) 846-6851. mckeeta@mail.nih.gov. ASSOCIATED CONTENT:Supporting Information: 1 H and 13 C NMR spectra for 1-2, chiral HPLC analysis of 1, Gaussian keywords, calculated excitation energies, oscillator strengths, and rotational strengths for 1-2, important dihedral angles of conformers 1a-1f and 2a-2f, conformational analysis of 1, calculated ORD values for 1-2, and coordinates of conformers 1a-1f and 2a-2f. This material is available free of charge via the Internet at http://pubs.acs.org. the extrinsic and intrinsic pathways and involves the participation of the mitochondria. 4 TRAIL is particularly important because it selectively induces apoptosis in cancer cells, while showing little to no effect in normal cells. 1,5 However, TRAIL resistance has been widely documented, 5-9 and there is evidence to suggest that combination chemotherapy regimens may b...

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“…The roots of Morinda geminata DC are a source of anthraquinones. Anthraquinones of Rubiaceae plants have been reported as molecules possessing in vitro biological activities with antimicrobial 18 , antifungal 19 , hypotensive, analgesic 20 , antimalarial 18,21 , antileukemic and mutagenic functions 22,23 . In addition, the anthraquinones [24][25][26][27][28][29][30] we have isolated from Morinda geminata DC have widespread bioactive potential.…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial anthraquinones and triterpenoid isolated from Morinda geminata DC (Rubiaceae)

et al. 2017

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Morinda geminata DC is a plant of the traditional Senegalese pharmacopoeia, the leaves of which are used in the treatment of various diseases. The phytochemical investigation of its leaves and roots resulted in the isolation of the triterpenoid ursolic acid 6, and five known anthraquinones analogues: nordamnacanthal 1, damnacanthal 2, damnacanthol 3, lucidin-ω-ethyl ether 4, and anthraquinone 5. The isolated compounds were characterized by NMR and mass-spectrometry and were evaluated for their antimicrobial properties. Compounds 1 and 4 displayed significant antimicrobial activities towards Staphylococcus aureus. The present study constitutes the first phytochemical examination of the leaves and roots of Morinda geminata DC.

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Antifungal anthraquinones from Morinda lucida

Cited by 72 publications

References 15 publications

Hydroxylated anthraquinones produced by Geosmithia species

Hydroxylated anthraquinones produced by Geosmithia species

Synergistic trail sensitizers from Barleria alluaudii and Diospyros maritima

Antimicrobial anthraquinones and triterpenoid isolated from Morinda geminata DC (Rubiaceae)

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