Micromonosporin A, a Novel 24‐Membered Polyene Lactam Macrolide from <i>Micromonospora</i> sp. Isolated from Peat Swamp Forest

Thawai, Chitti; Kittakoop, Prasat; Tanasupawat, Somboon; Suwanborirux, Khanit; Sriklung, Kanlayanee; Thebtaranonth, Yodhathai

doi:10.1002/cbdv.200490055

Cited by 23 publications

(29 citation statements)

References 24 publications

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“…Typically, colonies on agar media are initially light orange, becoming orange, red, brown or purple with the production of spores. Micromonospora is the type genus of the family Micromonosporaceae and contains microorganisms with potential biotechnological applications (Ismet et al, 2004;Thawai et al, 2004). Micromonosporae have been isolated from diverse habitats including soil, water and marine sediments (Kawamoto, 1989;Zhao et al, 2004;Maldonado et al, 2005;de Menezes et al, 2008).…”

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confidence: 99%

The genus Micromonospora is widespread in legume root nodules: the example of Lupinus angustifolius

et al. 2010

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Our current knowledge of plant-microbe interactions indicate that populations inhabiting a host plant are not restricted to a single microbial species but comprise several genera and species. No one knows if communities inside plants interact, and it has been speculated that beneficial effects are the result of their combined activities. During an ecological study of nitrogen-fixing bacterial communities from Lupinus angustifolius collected in Spain, significant numbers of orangepigmented actinomycete colonies were isolated from surface-sterilized root nodules. The isolates were analysed by BOX-PCR fingerprinting revealing an unexpectedly high genetic variation. Selected strains were chosen for 16S rRNA gene sequencing and phylogenetic analyses confirmed that all strains isolated belonged to the genus Micromonospora and that some of them may represent new species. To determine the possibility that the isolates fixed atmospheric nitrogen, chosen strains were grown in nitrogen-free media, obtaining in some cases, significant growth when compared with the controls. These strains were further screened for the presence of the nifH gene encoding dinitrogenase reductase, a key enzyme in nitrogen fixation. The partial nifH-like gene sequences obtained showed a 99% similarity with the sequence of the nifH gene from Frankia alni ACN14a, an actinobacterium that induces nodulation and fixes nitrogen in symbiosis with Alnus. In addition, in situ hybridization was performed to determine if these microorganisms inhabit the inside of the nodules. This study strongly suggests that Micromonospora populations are natural inhabitants of nitrogen-fixing root nodules.

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Section: Introductionmentioning

confidence: 99%

The genus Micromonospora is widespread in legume root nodules: the example of Lupinus angustifolius

et al. 2010

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“…There is a small family of related macrocyclic lactams, and the most closely related are salinilactam ( 2 ) from the marine actinomycete Salinispora tropica (9) and macromonosporin A ( 3 ) from the acidic peat swamp forest actinomycete Micromonospora sp. (10)…”

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Sceliphrolactam, a Polyene Macrocyclic Lactam from a Wasp-Associated Streptomyces sp.

Poulsen

Currie

et al. 2011

Org. Lett.

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A previously unreported 26-membered polyene macrocyclic lactam, sceliphrolactam, was isolated from an actinomycete, Streptomyces sp., associated with the mud dauber, Sceliphron caementarium. Sceliphrolactam’s structure was determined by 1D- and 2D-NMR, MS, UV, and IR spectral analysis. Sceliphrolactam displays antifungal activity against amphotericin B-resistant Candida albicans (MIC = 4 μg/mL, 8.3 μM).

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“…The 1 H, 1 H-COSY spectrum showed the connectivity from HÀC(3) to HÀC (6), and also demonstrated couplings between CH 2 (7) and CH 2 (8), and between HÀC(3') and HÀC(4'). The HMBC spectral data were very informative concerning the assembly of the gross structure of 1.…”

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confidence: 98%

“…The HMBC spectral data were very informative concerning the assembly of the gross structure of 1. The following 1 H, 13 C long range correlations were observed: HÀC(3) to C(1); both HÀC(4) and HÀC (6) to C(2); HÀC(5) to C(1); CH 2 (7) to C(1), C(2), and C(3); CH 2 (8) to C(5') and C(6'); the 2'-Me H-atoms to C(2') and C(3'); HÀC(3') to C(4'a); HÀC(4') to C(2'), C(5'), and C(8'a); HÀC(6') to C (8) and C(7'); the 7'-OMe H-atoms to C(7'); and the 8'-Me H-atoms to C(7'), C(8'), and C(8'a). On the basis of these spectral data, bauhinol A (1) was identified as 2-[2-(7-methoxy-2,2,8-trimethyl-2H-1-benzopyran-5-yl)ethyl]phenol.…”

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confidence: 99%

“…The antimycobacterial activity was assayed against Mycobacterium tuberculosis H37Ra, using the Microplate Alamar-Blue Assay (MABA) [16]. The twofold dilution technique, starting at a concentration of 200 mg/ml, was used, and the MIC value 1 ) was recorded at the minimum concentration of the tested compound inhibiting bacterial growth. The standard drugs, isoniazid (Sigma, USA) and kanamycin sulfate (Sigma, USA), used as reference compounds for the antimycobacterial assay, showed MIC values of 0.040 ± 0.090 and 2.0 ± 5.0 mg/ml, resp.…”

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Novel Biologically Active Bibenzyls from Bauhinia saccocalyx Pierre

Apisantiyakom

Kittakoop

Manyum

et al. 2004

Chemistry & Biodiversity

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Four new bibenzyls, bauhinols A-D (1-4), together with the two known bibenzyls 5 and 6, were isolated from the roots of Bauhinia saccocalyx, and their structures were elucidated by analyses of spectroscopic data. Bauhinol A (1) exhibits significant cytotoxicity towards NCI-H187 (small-cell lung cancer), BC (breast cancer), and KB (oral-cavity cancer) cell lines, with IC50 values of 2.7-4.5 microg/ml. Bauhinol B (2) is cytotoxic against NCI-H187 (IC50 = 1.1 microg/ml) and BC (IC50 = 9.7 microg/ml) cell lines, but inactive toward the KB cell line (at 20 microg/ml). Compound 2 also is mildly antifungal towards Candia albicans (IC50 = 28.9 microg/ml). Bibenzyl 6 is active against NCI-H187 (IC50 = 14.1 microg/ml) and BC (IC50 = 4.0 microg/ml) cells, but inactive (at 20 microg/ml) toward the KB cell line. Compounds 1, 2, and 6 show mild antimycobacterial activities, with MIC values of 25-50 microg/ml, but are inactive at 20 microg/ml against the K1 malarial parasite strain (Plasmodium falciparum). While bauhinol A (1) is inactive against cyclooxygenase 1 (COX-1) and cyclooxygenase 2 (COX-2), compounds 2 and 6 inhibit both COX-1 and COX-2, with IC50 values comparable to those of the standard drug, aspirin (Table 3).

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Micromonosporin A, a Novel 24‐Membered Polyene Lactam Macrolide from Micromonospora sp. Isolated from Peat Swamp Forest

Cited by 23 publications

References 24 publications

The genus Micromonospora is widespread in legume root nodules: the example of Lupinus angustifolius

The genus Micromonospora is widespread in legume root nodules: the example of Lupinus angustifolius

Sceliphrolactam, a Polyene Macrocyclic Lactam from a Wasp-Associated Streptomyces sp.

Novel Biologically Active Bibenzyls from Bauhinia saccocalyx Pierre

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