SCH 42137, a novel antifungal antibiotic from an Actinoplanes sp. Fermentation, isolation, structure and biological properties.

Cooper, Raymond; Truumees, Imbi; Gunnarsson, I.; Loebenberg, David; Horan, Ann C.; Marquez, Joseph A.; Patel, Mahesh; Gullo, Vincent P.; Puar, Mohindar S.; Das, Pradip R.; Mittelman, Stanley

doi:10.7164/antibiotics.45.444

Cited by 19 publications

(18 citation statements)

References 6 publications

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“…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] …”

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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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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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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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“…Table 53. Compound 106 is structurally related to a small family of polycyclic antibiotics including cervinomycins [146] , citreamicins [148] , simaomycins [149] and the highly cytotoxic polycyclic xanthones actinoplanones A~G; which have a lactam with partial reduction at ring F [150] . They were isolated from terrestrial Micromonospora, Streptomyces, Actinomadura and Actinoplanes strains, respectively.…”

Section: Optimization Of the Terrestrial Streptomyces Sp Bl 2/5831mentioning

confidence: 99%

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Ueda¹,

Hashimoto²,

Yamamura³

et al. 2011

J Antibiot

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“…Albofungin is a polycyclic isoquinolone-xanthone and this family of compounds (Winter et al, 2013) have a wide range of potent bioactivities, including antimicrobial (Carter et al, 1991), anticoccidial (Lee et al, 1989), antifungal (Cooper et al, 1992;Chu et al, 1997), antimalarial and anticancer activities (Dobler & Keller-Schierlein, 1977;Liu et al, 2013). Albofungin, also known as kanchanomycin, was identified as a secondary metabolite from various Streptomyces species, and possesses high antibiotic, antihelmintic and antitumour activity (Fukushima et al, 1973;Goldberg, 1975;Kempter et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

She

Sung

et al. 2020

Acta Crystallogr C

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The potent antibiotics albofungin [systematic name: (1S,4R,8aR)-13-amino-1,15,16-trihydroxy-4-methoxy-12-methyl-3,4,8a,13-tetrahydro-1H-xantheno[4′,3′,2′:4,5][1,3]benzodioxino[7,6-g]isoquinoline-14,17(2H,9H)-dione, C27H24N2O9, 1] and its chlorinated analogue chloroalbofungin (the 11-chloro analogue, C27H23ClN2O9, 2) have been crystallized following their isolation from the bacterial strain Streptomyces chrestomyceticus and their structures determined by single-crystal X-ray diffraction. The novel N-aminoquinolone molecular arrangement shows N—N bond lengths of 1.4202 (16) and 1.424 (2) Å in 1 and 2, respectively. The regiochemistry of chloro substitution in the A-ring is para to the quinolone O atom, with a C—Cl bond length of 1.741 (2) Å. The absolute stereochemistry at three chiral centres of the xanthone rings (i.e. 10S, 13R and 19R) is confirmed. Both compounds crystallize in chiral Sohncke space groups consistent with enantiopurity, but are not fully isostructural. A preserved supramolecular construct (SC) confers two-dimensional (2D) isostructurality, but the SC self-associates via either a twofold screw operation in 1, giving a monoclinic P21 structure, or a twofold rotation in 2, affording a monoclinic C2 structure with a doubled unit-cell axis.

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SCH 42137, a novel antifungal antibiotic from an Actinoplanes sp. Fermentation, isolation, structure and biological properties.

Cited by 19 publications

References 6 publications

Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

Kibdelones: Novel Anticancer Polyketides from a Rare Australian Actinomycete

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

Albofungin and chloroalbofungin: antibiotic crystals with 2D but not 3D isostructurality

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