Biotransformation of Vermitaline by <i>Cunninghamella echinulata</i>

Lu, Yifeng; Chen, Ke-Yu; Li, Hui‐Liang; Pei, Yue‐Hu; Liu, Runhui; Zhang, Wei‐Dong

doi:10.1002/hlca.200890083

Cited by 8 publications

(1 citation statement)

References 12 publications

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“…The known constituents were determined by juxtaposing spectroscopic and physical findings ( 1 H-NMR, 13 C-NMR, DEPT, and MS) with the published reports, and this included 3-Angeloylzygadenine (3) [31], 3-Veratroylgemine (4) [32], Jervine (5) [33], Verazine (6) [34], Vermitaline (7) [35], 3-Angeloylzygadenine-β-N-oxide (8) [36], Cyclopamine (9) [37], Veratramine (10) [38].…”

Section: Structural Assessment Of Known Constituentsmentioning

confidence: 99%

Steroidal Alkaloids from the Roots of Veratrum mengtzeanum Loes. with Their Anti-Inflammatory Activities

Yuan,

Ma,

Liu

et al. 2023

Molecules

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The phytochemical investigation of Veratrum mengtzeanum Loes. roots resulted in the isolation and characterization of two novel, namely Mengtzeanines A (1), Mengtzeanines B (2), and eight known steroidal alkaloids (3–10). Their structural properties were assessed though extensive spectroscopic techniques. All constituents 1–10 were analyzed for suppression of NO formation in LPS-induced RAW264.7 macrophages. Among them, constituent 6 (Verazine) showed inhibition against LPS-induced NO production (IC50 = 20.41 μM). Additionally, compound 6 could inhibit the secretion of IL1β, IL6, and TNFα, and downregulate the productions of iNOS and COX2 in LPS-induced RAW264.7 macrophages. Further experiments revealed that 6 exhibited a potent anti-inflammatory level in LPS-stimulated RAW264.7 macrophages via inhibiting NF-κB, and triggering of Keap1/Nrf2/HO-1 axis, implying that compound 6 may be a promising candidate for treating inflammatory disorders.

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Section: Structural Assessment Of Known Constituentsmentioning

confidence: 99%

Steroidal Alkaloids from the Roots of Veratrum mengtzeanum Loes. with Their Anti-Inflammatory Activities

Yuan,

Ma,

Liu

et al. 2023

Molecules

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Biotransformation of Jervine by Cunninghamella echinulata

Chen

et al. 2013

Helvetica Chimica Acta

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Biotransformation of jervine (1) by Cunninghamella echinulata (ACCC 30369) was carried out. Four biotransformation products were obtained, and three of them, 3 -5, were identified as new compounds. On the basis of their NMR and mass-spectral data, their structures were characterized as jervinone (2), 7a-hydroxyjervine (3), 14a-hydroxyjervine (4), and 1b,7a-dihydroxyjervine (5). The X-ray diffraction structure of 1 is also reported for the first time.

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Biotransformation of Oleaside A by Cunninghamella echinulata

Lu¹,

Liu²,

Han³

et al. 2014

Helvetica Chimica Acta

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Biotransformation of oleaside A (1) by Cunninghamella echinulata (ACCC 30369) was carried out to afford two products, (6R)-6-hydroxyoleaside A (2) and (7S)-7-hydroxyoleaside A (3). The structures of 2 and 3 were elucidated by extensive NMR analyses and further confirmed by single-crystal X-ray diffraction analysis. We also report herein the X-ray diffraction structure of oleaside A (1) for the first time. Compounds 1 -3 were evaluated for their cytotoxic activities against the A549, HCT116, HepG2, and HL-60 human cancer cell lines.Introduction. -Microbial transformation is an effective tool for the structural modification of natural bioactive compounds. Its application in asymmetric synthesis is increasing due to its versatility and simplicity [1]. A variety of transformations on natural products such as oxidation, reduction, hydrolysis, isomerization, epimerization, rearrangement, d-homoannulation, Michael addition, and reverse aldol reaction have already been performed [2]. Cunninghamella echinulata, a filamentous fungus, is recognized for its potential for steroid hydroxylation and has been noted for its ability to mimic mammalian hepatic metabolism with other substrates [3] [4].Oleaside A (1) is one of the most important cardiac glycosides derived from the Nerium oleander L. Recently, the anticancer effects of cardiac glycosides have been reported [5 -7]. In continuation of our biotransformation studies on the natural anticancer products [8] [9], we now report the characterization of two metabolites of oleaside A (1) in cell suspension of C. echinulata (ACCC 30369). These metabolites were identified as (6R)-6-hydroxyoleaside A (2) and (7S)-7-hydroxyoleaside A (3) by spectroscopic methods. We also report here the X-ray diffraction structure of these three compounds. Compounds 1 -3 (see Fig. 1) were evaluated for their cytotoxic activities against the A549, HCT116, HepG2, and HL-60 human cancer cell lines.

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Biotransformation of Vermitaline by Cunninghamella echinulata

Cited by 8 publications

References 12 publications

Steroidal Alkaloids from the Roots of Veratrum mengtzeanum Loes. with Their Anti-Inflammatory Activities

Steroidal Alkaloids from the Roots of Veratrum mengtzeanum Loes. with Their Anti-Inflammatory Activities

Biotransformation of Jervine by Cunninghamella echinulata

Biotransformation of Oleaside A by Cunninghamella echinulata

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