Marine Natural Products as Antituberculosis Agents

Sayed, Khalid A. El; Bartyzel, Piotr; Shen, Xiaoyu; Perry, Tony L.; Zjawiony, Jordan K.; Hamann, Mark T.

doi:10.1016/s0040-4020(99)01093-5

Cited by 173 publications

(120 citation statements)

References 24 publications

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“…Noteworthy is the percent of sponge extracts (40%) active against M. tuberculosis H37Rv. Only recently marine sponges have started to be investigated for the search for new antituberculosis agents, for which they show to be a promising source of new drugs for the treatment of tuberculosis (Copp, 2003;El Sayed et al, 2000;Donia and Hamann, 2003). A smaller percentage of sponge extracts displayed cytotoxic activity against MCF-7 breast cancer cells (11%), HCT-8 colon cancer cells (18%) and B16 murine melanoma cancer cells (8%).…”

Section: Marine Spongesmentioning

confidence: 99%

Antibiotic, cytotoxic and enzyme inhibitory activity of crude extracts from Brazilian marine invertebrates

Seleghim¹,

Lira²,

Kossuga³

et al. 2007

Rev. bras. farmacogn.

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Section: Marine Spongesmentioning

confidence: 99%

Antibiotic, cytotoxic and enzyme inhibitory activity of crude extracts from Brazilian marine invertebrates

Seleghim¹,

Lira²,

Kossuga³

et al. 2007

Rev. bras. farmacogn.

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“…puupehenone (14) from the sponge Hyrtios sp. [46,47], which also shows a potent antituberculosis activity [48]). Among those are also the ones with a 4,9-friedo-rearranged skeleton, such as ilimaquinone (3) [49], and a related amino derivative 15 from the sponge Dactylospongia elegans [50], the nakijiquinones 5 [11] and especially avarone (2) and avarol (1), with strong ED 50 activities of 0.62 µM and 0.93 µM, respectively, for mouse lymphoma cells [51,52].…”

Section: Biological Effects I) Antitumor Activitymentioning

confidence: 99%

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

Sladić

Gašić

2006

Molecules

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A review of results of bioactivity and reactivity examinations of marine sesquiterpene (hydro)quinones is presented. The article is focused mostly on friedorearranged drimane structural types, isolated from sponges of the order Dictyoceratida. Examples of structural correlations are outlined. Available results on the mechanism of redox processes and examinations of chemo-and regioselectivity in addition reactions are presented and, where possible, analyzed in relation to established bioactivities. Most of the bioactivity examinations are concerned with antitumor activities and the mechanism thereof, such as DNA damage, arylation of nucleophiles, tubulin assembly inhibition, protein kinase inhibition, inhibition of the arachidonic cascade, etc. Perspectives on marine drug development are discussed with respect to biotechnological methods and synthesis. Examples of the recognition of validated core structures and synthesis of structurally simplified compounds retaining modes of activity are analyzed.

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“…22 The in vitro activity of manzamines against Mycobacterium tuberculosis (H37Rv), malaria parasite Plasmodium falciparum, and Leishmania donovani, the causative agent for visceral leishmaniasis, is reported in Table 2. Most manzamines were active against M. tuberculosis with MICs < 12.5 μg/mL.…”

Section: Author Manuscriptmentioning

confidence: 99%

“…Pentamidine and amphotericine B were tested as standard antileishmanials. Antimalarial, 26 antituberculosis, 22 and HIV 27 assays were performed using the referenced procedures.…”

Section: In Vitro Antileishmanial Assaymentioning

confidence: 99%

New Manzamine Alkaloids with Activity against Infectious and Tropical Parasitic Diseases from an Indonesian Sponge

et al. 2003

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Eleven manzamine type alkaloids, two β-carbolines, and five nucleosides have been isolated from an Indonesian sponge. Among these are the previously characterized 12,34-oxamanzamine A, 12,34-oxamanzamine E, manzamine A (1), 8-hydroxymanzamine A, 6-deoxymanzamine X, manzamine E (2), manzamine X, manzamine F (4), norharman, thymine, 2′,3′-didehydro-2′,3′-dideoxyuridine, uracil, thymidine, and 2′-deoxyuridine. The structures for the five new compounds have been assigned as 32,33-dihydro-31-hydroxymanzamine A (3), 32,33-dihydro-6-hydroxymanzamine A-35-one (5), des-N-methylxestomanzamine A (6), 32,33-dihydro-6,31-dihydroxymanzamine A (7), and 1,2,3,4-tetrahydronorharman-1-one (8), on the basis of NMR and X-ray data. The bioactivity and SAR of the manzamines against malaria, TB, and leishmania are also presented. The structural revision of two previously reported pyrazoles as uracil and thymine is also discussed.Manzamines are unique β-carboline alkaloids isolated from Indo-Pacific sponges and characterized by having an intricate nitrogen-containing polycyclic system. In 1986, Higa and co-workers first reported manzamine A from the Okinawan sponge of the genus Haliclona. 1 These compounds exhibit a diverse range of bioactivities including cytotoxicity, 1 insecticidal, 2 and antibacterial 3 as well as the exciting curative activity against malaria in animal models. 4,5 Since the first report of manzamine A, an additional 40 manzamine-type alkaloids have been reported from nine different sponge genera. 6,7 In our continuing search for manzamine-related alkaloids with significant activity against infectious diseases, we have identified several novel manzamine alkaloids from an Indonesian sponge, and herein we describe their structure determination and biological activity. *To whom correspondence should be addressed. Tel: (662) 915-5730. Fax: (662) 915-6975. mthamann@olemiss.edu. Supporting Information Available: Copies of 1 H and 13 C NMR spectra for all new compounds, HMQC spectra for 3, 5-7, HMBC spectra for 5-8, and X-ray data for 3. This material is available free of charge via the Internet at http://pubs.acs.org. (Table 1) includes aromatic proton resonances similar to those of manzamine E. 12 Spectral data of how 3 differs from manzamine E (2) includes the presence of 13 CH carbons (manzamine E has 12 CH carbons) and the absence of the low-field C-31 carbonyl carbon signal of manzamine E. In place of the carbonyl carbon compound 3 has a signal at 70.9 ppm, which correlates with a multiplet at 4.05 ppm in the HMQC spectrum. The presence of this new OH-functionality is confirmed by a number of long-range 1 H-13 C correlations H 2 -29 and H 2 -33 to C-31, Figure 1 HHS Public Access Author ManuscriptAuthor Manuscript Author ManuscriptAuthor Manuscript C-12, C-24, C-25, C-26, and C-34 of 3 were elucidated to be the same as those of manzamine E by NOESY data as well as comparable 13 C chemical shifts. In addition both compounds were isolated from the same sponge and possessed dextrorotation. The relative config...

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Marine Natural Products as Antituberculosis Agents

Cited by 173 publications

References 24 publications

Antibiotic, cytotoxic and enzyme inhibitory activity of crude extracts from Brazilian marine invertebrates

Antibiotic, cytotoxic and enzyme inhibitory activity of crude extracts from Brazilian marine invertebrates

Reactivity and Biological Activity of the Marine Sesquiterpene Hydroquinone Avarol and Related Compounds from Sponges of the Order Dictyoceratida

New Manzamine Alkaloids with Activity against Infectious and Tropical Parasitic Diseases from an Indonesian Sponge

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