Mumiamicin: Structure and bioactivity of a new furan fatty acid from &lt;i&gt;Mumia&lt;/i&gt; sp. YSP-2-79

Kimura, Tōru; Tajima, Ayano; Inahashi, Yuki; Iwatsuki, Masato; Kasai, Hiroaki; Mokudai, Takayuki; Niwano, Yoshimi; Shiomi, Kazuro; Takahashi, Yōko; Ōmura, Satoshi; Nakashima, Takuji

doi:10.2323/jgam.2017.06.004

Cited by 11 publications

(6 citation statements)

References 23 publications

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“…The mangromicins [ 43 , 44 , 45 ], K10-0216 KA and KB [ 46 ], and pyrizomicins [ 47 ], which have differing core structures, were found in a culture broth of Lechevalieria aerocolonigenes K10-0216 isolated from sediment from mangroves. Mumiamicin [ 48 ] was found in an actinomycete strain isolated from sea sediment, while sagamilactam [ 49 ] and the dipyrimicins [ 50 ] originated in actinomycete strains from soil. In Section 5.1 , we describe, in detail, the discovery of other compounds, notably the trehangelins from Polymorphospora rubra K07-0510 and compounds from Lechevalieria aerocolonigenes K10-0216.…”

Section: Novel Compounds Discovered By Physicochemical (Pc) Screenmentioning

confidence: 99%

Actinomycetes, an Inexhaustible Source of Naturally Occurring Antibiotics

2018

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Global public health faces a desperate situation, due to the lack of effective antibiotics. Coordinated steps need to be taken, worldwide, to rectify this situation and protect the advances in modern medicine made over the last 100 years. Work at Japan’s Kitasato Institute has been in the vanguard of many such advances, and work is being proactively tailored to promote the discovery of urgently needed antimicrobials. Efforts are being concentrated on actinomycetes, the proven source of most modern antibiotics. We devised a novel physicochemical screening mechanism, whereby simple physico-chemical properties, in conjunction with related detection methods, such as LC/MS, LC/UV, and polarity, could be used to identify or predict new compounds in a culture broth, simply by comparing results with existing databases. New compounds are isolated, purified, and their structure determined before being tested for any bioactivity. We used lyophilized actinomycete strains from the Kitasato Microbial Library, most more than 35 years old, and found 330 strains were producers of useful bioactive substances. We also tested organisms found in fresh samples collected in the complex environments from around plant roots, as well as from sediments of mangrove forests and oceans, resulting in the discovery of 36 novel compounds from 11 actinomycete strains. A compound, designated iminimycin, containing an iminium ion in the structure was discovered from the culture broth of Streptomyces griseus OS-3601, which had been stored for a long time as a streptomycin-producing strain. This represented the first iminium ion discovery in actinomycetes. Compounds with a cyclopentadecane skeleton containing 5,6-dihydro-4-hydroxyl-2-pyrone ring and tetrahydrofuran ring, designated mangromicins, were isolated from the culture broth of Lechevalieria aerocolonigenes K10-0216 obtained from sediment in a mangrove forest. These structures are extremely unique among natural compounds. From the same culture broth, new steroid compounds, named K10-0216 KA and KB, and other new compounds having a thiazole and a pyridine ring, named pyrizomicin A and B, were discovered. New substances can be found from actinomycetes that have been exhaustively studied. Novel compounds with different skeletons can be found from a single broth of one strain. The sought after new antibiotics will arise from continued exploitation of the actinomycetes, especially rare actinomycetes. Work on new organisms and samples should be augmented by re-examination of known actinomycetes already in storage. New research should also be carried out on the manipulation of culture media, thereby stimulating actinomycete strains to produce novel chemicals. The establishment of wide-ranging international research collaborations will facilitate and expedite the efficient and timely discovery and provision of bioactive compounds to help maintain and promote advances in global public health.

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Section: Novel Compounds Discovered By Physicochemical (Pc) Screenmentioning

confidence: 99%

Actinomycetes, an Inexhaustible Source of Naturally Occurring Antibiotics

2018

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“…For the total synthesis of 3D5 , a unique F‐acid found in the soft corals S. glaucum and S. gemmatun (Scheme 2 C), we employed a sequence of reduction, Appel reaction, and cyanation of the furan 3 ll to produce the nitrile 5 , which underwent hydrolysis in 98 % yield to give the F‐acid [42] . Similarly, the furan 3 cc was converted into the nitrile 6 , which was hydrolyzed in 98 % yield to produce hydromumiamicin, [43] an F‐acid derivative in the actinomycete strain Mumia sp . YSP‐2‐79 with antimicrobial and antioxidant activity.…”

Section: Resultsmentioning

confidence: 99%

“…Forschungsartikel underwent hydrolysis in 98 %y ield to give the F-acid. [42] Similarly,t he furan 3cc was converted into the nitrile 6, which was hydrolyzed in 98 %yield to produce hydromumiamicin, [43] an F-acid derivative in the actinomycete strain Mumia sp. YSP-2-79 with antimicrobial and antioxidant activity.W hile several syntheses have been reported of Facids featuring long carboxyalkyl chains,o ur present total syntheses are the first for F-acids having at hree-carbon carboxyalkyl chain.…”

Section: Angewandte Chemiementioning

confidence: 99%

Unified Approach to Furan Natural Products via Phosphine‐Palladium Catalysis

Chen

Kwon

2021

Angewandte Chemie

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Polyalkyl furans are widespread in nature,o ften performing important biological roles.D espite ap lethora of methods for the synthesis of tetrasubstituted furans,t he construction of tetraalkylf urans remains non-trivial. The prevalence of alkylgroups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkylf urans, calls for ageneral synthetic protocol for polyalkylfurans.This paper describes aM ichael-Heck approach, using sequential phosphine-palladium catalysis,f or the preparation of various polyalkylf urans from readily available precursors.T he versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes,n amely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran;the marine natural products plakorsins A, B, and Dand plakorsin Dmethyl ester;and the furan fatty acids 3D5 and hydromumiamicin.

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“…Research Articles underwent hydrolysis in 98 %y ield to give the F-acid. [42] Similarly,t he furan 3cc was converted into the nitrile 6, which was hydrolyzed in 98 %yield to produce hydromumiamicin, [43] an F-acid derivative in the actinomycete strain Mumia sp. YSP-2-79 with antimicrobial and antioxidant activity.W hile several syntheses have been reported of Facids featuring long carboxyalkyl chains,o ur present total syntheses are the first for F-acids having at hree-carbon carboxyalkyl chain.…”

Section: Chemiementioning

confidence: 99%