Malbrancheamide, a new calmodulin inhibitor from the fungus Malbranchea aurantiaca

Fluorescence, circular dichroism, NMR, and docking studies of the interaction of the alkaloid malbrancheamide with calmodulin

“…Compounds 1 and 2 were characterized by comparison with authentic samples previously isolated from M. aurantiaca [12][13][14] , and the NMR data of 4 was consistent with the synthetic premalbrancheamide described by Ding et al 21 . Compound 3 is a new natural product and its complete structural characterization was achieved using a combination of IR, CD, UV, as well as 1D ( 1 H and 13 C-NMR) and 2D (HSQC and HMBC) NMR analyses.…”

“…Fluorescence, circular dichroism, NMR, and docking studies of the interaction of the alkaloid malbrancheamide with calmodulin Interaction of the alkaloid malbrancheamide with calmodulin 379 isolation and structure elucidation of two novel indole alkaloids, namely malbrancheamide (1) and malbrancheamide B (2), from both the mycelium and culture broth of the fungus Malbranchea aurantiaca Sigler & Carmichael (Myxotrichaceae) 12,13 . Compounds 1 and 2 inhibited the activation of the CaM-deficient-CaMdependent cyclic adenosine monophosphate (cAMP) phosphodiesterase (PDE1), such as CPZ.…”

Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi

“…After hydrolysis of the amide bond of 13 , oxidation at C-24 followed by decarboxylative dehydration would afford notoamide L. 26 On the other hand, stephacidin A may be converted to aspergamide B 72 via notoamide R. Oxidative cleavage of the tri-substituted alkene in aspergamide B would generate aldehyde hydrate 16 ; simple ring closure would afford notoamide O. 27 Notoamide N is one of the rare chlorinated members of the family of prenylated indole alkaloids and this is the third chlorinated derivative following malbrancheamide, 21 malbrancheamide B 22 and spiromalbramide. 23 On the other hand notoamide P is the first brominated member of this family.…”

“…In particular, various prenylated indole alkaloids have been discovered, including the brevianamides, 1–7 marcfortines, 8,9 paraherquamides, 10–14 penicimutamides, 15 sclerotiamide, 16 asperparalines, 17 avrainvillamide, 18,19 stephacidins, 20 malbrancheamides, 21–23 notoamides, 24–27 versicolamide B, 28 chrysogenamide, 29 and recently the taichunamides (Fig. 1).…”

Chrysogenamide A from an Endophytic Fungus Associated with Cistanche deserticola and Its Neuroprotective Effect on SH-SY5Y Cells

“…Indole alkaloids possessing an unusual bicyclo [2.2.2] diazaoctane ring system have been isolated from different genera of fungi such as Aspergillus [12,9,13], Penicillium [14ϳ16] and Malbranchea [17]. 1 was a new member of this group of compounds, it possessed a skeleton expected to be an intermediate in the biosynthesis of the citrinadins A and B reported as a novel class of pentacyclic spiroindolinone alkaloids in 2005 [18].…”