2020
DOI: 10.1021/acs.jnatprod.0c00588
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Bioactive Alkaloids from the Actinomycete Actinoalloteichus sp. ZZ1866

Abstract: The new alkaloids marinacarbolines E–Q (1–10, 12–14), caerulomycin N (15), and actinoallonaphthyridine A (16), together with the known marinacarboline C (11) and cyanogramide (17), were isolated from the actinomycete Actinoalloteichus sp. ZZ1866. The structures of the isolated compounds were elucidated based on their HRESIMS data, extensive NMR spectroscopic analyses, Mosher’s method, ECD calculations, single-crystal X-ray diffraction analysis, and chemical degradation studies. Marinacarbolines E–L (1–8) share… Show more

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Cited by 28 publications
(22 citation statements)
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“…[ 31 ] Marinacarboline E ( 22 ), obtained from an Actinoalloteichus sp., is a novel alkaloid with an unusual indole‐ pyridone‐imidazole tetracyclic skeleton. [ 32 ] Dassonmycin A ( 23 ), from a marine sponge‐derived Nocardiopsis dassonvillei , is a novel thioalkaloid with a 6/6/6/6‐fused tetracyclic ring system. It is proposed to be biosynthesized from a nonribosomal peptide synthetase (NRPS) pathway and a chorismate pathway combined by a Michael addition reaction.…”
Section: Hot‐spot Compoundsmentioning
confidence: 99%
“…[ 31 ] Marinacarboline E ( 22 ), obtained from an Actinoalloteichus sp., is a novel alkaloid with an unusual indole‐ pyridone‐imidazole tetracyclic skeleton. [ 32 ] Dassonmycin A ( 23 ), from a marine sponge‐derived Nocardiopsis dassonvillei , is a novel thioalkaloid with a 6/6/6/6‐fused tetracyclic ring system. It is proposed to be biosynthesized from a nonribosomal peptide synthetase (NRPS) pathway and a chorismate pathway combined by a Michael addition reaction.…”
Section: Hot‐spot Compoundsmentioning
confidence: 99%
“…(R)-phenylethanolamine (PEA): white solid; 165.2 mg; isolated yield: 65.5 %; ee: > 99 %; [α]D20 = À 38.4 (c = 1.0 in EtOH); lit. [6a] [α]D25 = À 43.8 (c = 2.0 in EtOH); 1 Engineering of E. coli PPSSTCA(MVIK) strain co-expressing PAL, PAD, SMO, StEH, AldO(MVIK) and CvTA and whole-cell biotransformation of l-Phe to (R)-PEA E. coli PPSSTCA(MVIK) strain was obtained by transforming previously constructed pET-pal-pad [23] into chemical competent E. coli SSTCA(MVIK) cells. Freshly prepared E. coli PPSSTCA(MVIK) cells (10-25 g cdw/L) were added into a mixture of 10 mL KP buffer (200 mM, pH 8.0) containing 2 %(w/v) glucose, 1 mM PLP, 10-30 mM l-Phe, and 100-300 mM l-alanine, with 10 mL n-hexadecane to start the biotransformation at 30 °C and 220 rpm.…”
Section: Preparation Of (R)-pea By Biotransformation Of Styrene With ...mentioning
confidence: 99%
“…( R )‐phenylethanolamine (PEA) is a useful and important chiral intermediate in organic synthesis, pharmaceutical manufactory and medicinal chemistry. While its structure widely presents in numerous natural products such as bioactive alkaloids, [1] some derivatives have been developed as beta‐3 adrenergic agonist drugs [2] for treating obesity and non‐insulin dependent diabetes (type II) such as Myrbetriq, [3] or as a Sonic hedgehog signaling inhibitor [4] . Due to its strong cardiovascular activity, PEA sulfate salt, Apophedrin, is used as topical vasoconstrictor [5] …”
Section: Introductionmentioning
confidence: 99%
“…Natural N-substituted alkaloids are common secondary metabolites that reported from different terrestrial, marine and microbial organisms [25][26][27][28][29][30][31]. Reported substituents on the N atoms include OH, hydroperoxy, alkyl, heteroaromatic functionalities, and others [25][26][27][28][29][30][31]. Thus, fusaripyridine B represents an additional example of these alkaloids with N,N'-OH functionalities.…”
Section: Structure Of Fusaripyridine B (2)mentioning
confidence: 99%