Zur Kenntnis von Levorin A und Candicidin

Bosshardt, R.; Bickel, Hans

doi:10.1007/bf02144363

Cited by 16 publications

(5 citation statements)

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“…For instance, the candicidin complex was previously considered to consist of at least three, four to five, or even nine components. Moreover, some authors postulated a very close resemblance, if not identity, of candicidin and levorin complexes. ,, Recently, we have shown that candicidin, levorin, and also ascosin are complexes of three major identical components, designated as A1, A2 (D), and A3 …”

Section: Resultsmentioning

confidence: 96%

Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer

et al. 2018

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Illumination of the aromatic heptaene macrolide antifungal antibiotic candicicin D with UV light results in an isomerization of the molecule. The product formed after irradiation of the candicidin complex with UV light (λ = 365 nm), namely, iso-candicidin D, was isolated and subjected to 2D NMR studies, consisting of DQF-COSY, ROESY, TOCSY, HSQC, and HMBC experiments. The obtained spectral data unambiguously evidenced that iso-candicidin D was the all-trans isomer of the native antibiotic, and straightening of the heptaenic chromophore was the only light-induced structural change that occurred. Hence, iso-candicidin D was proclaimed to be a prototype of a novel class of polyene macrolide antifungal antibiotics: the all-trans aromatic heptaenes, containing a macrolide ring similar to that of amphotericin B.

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Section: Resultsmentioning

confidence: 96%

Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer

et al. 2018

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“…As it was mentioned before, the structure of the main component of the candicidin complex, candicidin D, has been evidenced to be identical with the structure of levorin A2, the main component of the levorin complex8. As concerns the major component of the ascosin complex, ascosin A2, herein shown to exhibit the same chromatographic and spectroscopic parameters as candicidin D and levorin A2, no structural data have been available so far.…”

Section: Resultsmentioning

confidence: 86%

“…The aim of this article is to solve one of such cases, regarding the issue of the similarity of the three aromatic heptaene complexes, namely ascosin, candicidin and levorin, which was raised repeatedly in the previous studies89101112.…”

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confidence: 99%

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Analytical studies on ascosin, candicidin and levorin multicomponent antifungal antibiotic complexes. The stereostructure of ascosin A2

Szczeblewski

Laskowski

Kubacki

et al. 2017

Sci Rep

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In the class of polyene macrolides, there is a subgroup of aromatic heptaenes, which exhibit the highest antifungal activity within this type of antibiotics. Yet, due to their complex nature, aromatic heptaenes were not extensively studied and their potential as drugs is currently underexploited. Moreover, there are many inconsistencies in the literature regarding the composition and the structures of the individual components of the aromatic heptaene complexes. Inspired by one of such cases, herein we conducted the analytical studies on ascosin, candicidin and levorin using HPLC-DAD-(ESI)Q-TOF techniques. The resulting chromatograms and the molecular masses of the individual components of these three complexes strongly indicated that the major components of ascosin, candicidin and levorin are structurally identical. In order to validate these results, the main component of previously structurally uncharacterized ascosin was derivatized, isolated and subjected to 2D NMR studies. The resulting structure of the ascosin’s main component, herein named ascosin A2, was shown to be identical with the earlier reported structures of the main components of candicidin and levorin complexes: candicidin D and levorin A2. In the end, all the structural knowledge regarding these three antibiotic complexes was gathered, systematized and completed, and the new nomenclature was proposed.

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“…More detailed analysis of levorin A by the extensive CCD method with great number of transfers (up to 1000) has revealed that this product is a complex of closely related compounds, including levorin A 0 , A 1 , A 2 , A 3 and A 4 . The structure of levorin A 2 and the stereostructure of levorin A 3 have been elucidated to date.…”

Section: Introductionmentioning

confidence: 99%

The structure, including stereochemistry, of levorin A₁

et al. 2015

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Zur Kenntnis von Levorin A und Candicidin

Cited by 16 publications

References 3 publications

Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer

Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer

Analytical studies on ascosin, candicidin and levorin multicomponent antifungal antibiotic complexes. The stereostructure of ascosin A2

The structure, including stereochemistry, of levorin A₁

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Zur Kenntnis von Levorin A und Candicidin

Cited by 16 publications

References 3 publications

Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer

Light-Induced Transformation of the Aromatic Heptaene Antifungal Antibiotic Candicidin D into Its All-Trans Isomer

Analytical studies on ascosin, candicidin and levorin multicomponent antifungal antibiotic complexes. The stereostructure of ascosin A2

The structure, including stereochemistry, of levorin A1

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The structure, including stereochemistry, of levorin A₁