The Structures of Bioactive Cyclodepsipeptides, Beauveriolides I and II, Metabolites of Entomopathogenic Fungi Beauveria sp.

Abstract

Among the cyclodepsipeptides, beauveriolides I (1) and II (2) have been isolated from the mycelium of Beauveria sp., and their stereostructures were elucidated by spectral analyses coupled with syntheses of the corresponding 3-hydroxyoctanoic acid derivatives. Beauveriolide I (1) exhibited moderate insecticidal activities against Spodoptera litura and Callosobruchus chinensis.

Lydiamycins A–D: Cyclodepsipetides with Antimycobacterial Properties

“…[15] The largest group among them, 16 beauverolides, recently attracted interest because of their antiatherogenic activity, as demonstrated by inhibition of acyl-CoA-cholesterol acyltransferase (ACAT). [16] Altogether, the thirteen-membered ring depsipetides cover a wide range of biological activities, including antibiotic, [17] antifungal, [18] insecticidal, [19] and immunosuppressant properties. [20] Like the lydiamycins, none of them are known to display significant cytotoxic activity which is a very common characteristic of larger cyclodepsipetides.…”

Sequencing of new beauverolides by high‐performance liquid chromatography and mass spectrometry

“…In this work we used the isolated and most abundant beauveriolide I as a 'standard' 14 and tested separately two different mass spectral techniques with precursor ion selection (PSD MALDI and CID on an ion trap) and in-source CID mass spectra recorded on a sector instrument (APCI). We found that protonated cyclic tetrapeptides, beauverolides, can easily be sequenced by tandem mass spectrometry.…”

“…Various biological tests have indicated that beauverolides do not exhibit bactericidal, fungicidal or direct insecticidal effects. 13,14 However, they were shown to be apparently involved in insect immunomodulation. 15 macrophage-driven foam cell formation.…”

Enantioselective Total Synthesis of Octalactin A Using Asymmetric Aldol Reactions and a Rapid Lactonization To Form a Medium‐Sized Ring

“…By comparison of the sense of optical rotation of 24 (Scheme 4) and ent-24 (Scheme 5), it was revealed that the absolute stereochemistry of C-2 in 24 and 10 was R. In addition, 27 was treated with benzaldehyde dimethyl acetal to produce the cyclic compound 28, and a conventional one-carbon elongation via 29 and 30 afforded primary alcohol 31 as preliminarily reported by the Yamamura group. [20] Protection of the hydroxyl group with tert-butyldimethylsilyl (TBS) or triisopropylsilyl (TIPS) ether, followed by reductive cleavage of the benzylidene acetal, yielded the five-carbon units 34 and 35, respectively. Iodoalkanes 9 and 36 were prepared from 34 and 35 by treatment with I 2 and Ph 3 P, and the product 9 (Scheme 5) was identified by comparison with the former compound 9 derived from aldol syn-16 (Scheme 3); therefore, it can be deduced that C-3 in compounds 9 and 19 also has an R configuration.…”