Sch 54445:  A New Polycyclic Xanthone with Highly Potent Antifungal Activity Produced by <i>Actinoplanes </i>sp.

Chu, Min; Truumees, Imbi; Mierzwa, Ronald; Terracciano, Joseph; Patel, Mahesh; Loebenberg, David; Kaminski, James J.; Das, Pradip R.; Puar, Mohindar S.

doi:10.1021/np960737v

Cited by 33 publications

(41 citation statements)

References 2 publications

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“…HRESI(+)MS analysis of a minor kibdelone 7 revealed a pseudo molecular ion consistent with a molecular formula (C 29 H 22 35 ClNO 10 , Dmmu = 0.7) suggestive of a didehydro kibdelone A (1) analogue. The 1 H and 13 C NMR spectroscopic data for 7 were remarkably similar with that for 1 with the only significant differences being associated with ring F resonances, namely, the absence of a hydroxy methine, a significant downfield shift of the diastereotopic methylene resonances (H-12a, d H = 3.05 ppm; and H-12b, d H = 2.70 ppm), and COSY correlations that defined an isolated spin system involving H-10 (d H = 4.97 ppm), H-11 (d H = 4.14 ppm), and H 2 -12.…”

Section: Resultsmentioning

confidence: 99%

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Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

Ratnayake

Lacey²,

Tennant³

et al. 2007

Chemistry A European J

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The kibdelones are a novel family of bioactive heterocyclic polyketides produced by a rare soil actinomycete, Kibdelosporangium sp. (MST-108465). Complete relative stereostructures were assigned to kibdelones A-C (1-3), kibdelone B rhamnoside (5), 13-oxokibdelone A (7), and 25-methoxy-24-oxokibdelone C (8) on the basis of detailed spectroscopic analysis and chemical interconversion, as well as mechanistic and biosynthetic considerations. Under mild conditions, kibdelones B (2) and C (3) undergo a facile equilibration to kibdelones A-C (1-3), while kibdelone B rhamnoside (5) equilibrates to a mixture of kibdelone A-C rhamnosides (4-6). A plausible mechanism for this equilibration is proposed and involves air oxidation, quinone/hydroquinone redox transformations, and a choreographed sequence of keto/enol tautomerizations that aromatize ring C via a quinone methide intermediate. Kibdelones exhibit potent and selective cytotoxicity against a panel of human tumor cell lines and display significant antibacterial and nematocidal activity.

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Section: Resultsmentioning

confidence: 99%

“…kibdelones X X X citreamicins X X [12,17] kigamicins X X [15,16] simaomicins X X [14,18] albofungins X X X [8,19] actinoplanones X X X [10,11] Sch54445/56036/42137 X [20][21][22] cervinomycins X [23,24] …”

mentioning

confidence: 99%

Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

Ratnayake

Lacey²,

Tennant³

et al. 2007

Chemistry A European J

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“…23 ) are known to display broad antifungal activities. Disorazoles as represented by disorazole A 1 [180], xanthone isoquinoline derivatives such as SCH54445 [181], LL-Z1271 alpha [182], sonomolide B [183], coniochaetone A, 1-dehydroxyarthrinone [184, 185], pseudolaric acid B [186], soraphen A1α [187], and clabistrin A [188], all display antifungal activities, several of which are comparable to amphotericin B. Fusarielin A displays antifungal activity against A. fumigatus [189]. The structures of several key compounds are shown in Fig.…”

Section: Agents Exhibiting Antifungal Activity With Unknown Mechanismentioning

confidence: 99%

The Mechanistic Targets of Antifungal Agents: An Overview

Mazu¹,

Bricker²,

Flores‐Rozas³

et al. 2016

MRMC

161

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Pathogenic fungi are a major causative group for opportunistic infections (OIs). AIDS patients and other immunocompromised individuals are at risk for OIs, which if not treated appropriately, contribute to the mortality associated with their conditions. Several studies have indicated that the majority of HIV-positive patients contract fungal infections throughout the course of their disease. Similar observations have been made regarding the increased frequency of bone marrow and organ transplants, the use of antineoplastic agents, the excessive use of antibiotics, and the prolonged use of corticosteroids among others. In addition, several pathogenic fungi have developed resistance to current drugs. Together these have conspired to spur a need for developing new treatment options for OIs. To aid this effort, this article reviews the biological targets of current and emerging drugs and agents that act through these targets for the treatment of opportunistic fungal infections.

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“…Recently, there have been numerous reports of polycyclic xanthones showing a wide array of biological activities ranging from potent antifungal activity (Sch 5445, ( 16 )) 19 to heat shock protein inhibition (xantholipin, ( 6 )). 9a Simaomic in α ( 10 ), isolated from the culture broth of Actinomadura madurae ssp.…”

Section: Biological Activitymentioning

confidence: 99%

Polycyclic xanthone natural products: structure, biological activity and chemical synthesis

2013

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Polycyclic xanthone natural products are a family of polyketides which are characterized by highly oxygenated, angular hexacyclic frameworks. In the last decade, this novel class of molecules has attracted noticeable attention from the synthetic and biological communities due to emerging reports of their potential use as antitumour agents. The aim of this article is to highlight the most recent developments of this subset of the xanthone family by detailing the innate challenges of the construction of this class of natural products, new synthetic approaches, and pharmacological data.

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Sch 54445: A New Polycyclic Xanthone with Highly Potent Antifungal Activity Produced by Actinoplanes sp.

Cited by 33 publications

References 2 publications

Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

The Mechanistic Targets of Antifungal Agents: An Overview

Polycyclic xanthone natural products: structure, biological activity and chemical synthesis

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