Synthesis and Stereochemistry of the Antitumor Diterpenoid (+)-Zerumin B

Boukouvalas, John; Wang, Jianxin; Marion, Olivier; Ndzi, Bruno

doi:10.1021/jo0610154

Cited by 46 publications

(48 citation statements)

References 16 publications

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“…Similar differences have also been reported between zerumin B and 12-epizerumin B. 11 From these observations, compound 2 was identified as 12-epivitexolide A, and the 5S, 9S, 10S, 12S, absolute configuration was assigned to this compound.…”

Section: ■ Results and Discussionsupporting

confidence: 82%

“…Fraction 9 (2.25 g) exhibited the most effective antibacterial activity with 13 Gram-positive strains fully inhibited but no activity on Gram-negative strains. Subsequent flash chromatography on silica gel followed by preparative and analytical HPLC afforded the new vitexolides B, C, and E (3, 4, and 8, respectively) and 12-epivitexolide A (2) as well as the known vitexolides A and D (1 and 7, respectively), vitexolins A and B (5 and 6, respectively) along with acuminolide 12,13 (9), 3β-hydroxyanticopalic acid 14 (10), 8α-hydroxyanticopalic acid 15 (11), and 6α-hydroxyanticopalic acid 16 (12).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Antibacterial Labdane Diterpenoids from Vitex vestita

Corlay

Lecsö-Bornet²,

Leborgne

et al. 2015

J. Nat. Prod.

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A large-scale in vitro screening of tropical plants using an antibacterial assay permitted the selection of several species with significant antibacterial activities. Bioassay-guided purification of the dichloromethane extract of the leaves of the Malaysian species Vitex vestita, led to the isolation of six new labdane-type diterpenoids, namely, 12-epivitexolide A (2), vitexolides B and C (3 and 4), vitexolide E (8), and vitexolins A and B (5 and 6), along with six known compounds, vitexolides A (1) and D (7), acuminolide (9), 3β-hydroxyanticopalic acid (10), 8α-hydroxyanticopalic acid (11), and 6α-hydroxyanticopalic acid (12). Their structures were elucidated on the basis of 1D and 2D NMR analyses and HRMS experiments. Both variable-temperature NMR spectroscopic studies and chemical modifications were performed to investigate the dynamic epimerization of the γ-hydroxybutenolide moiety of compounds 1-4. Compounds were assayed against a panel of 46 Gram-positive strains. Vitexolide A (1) exhibited the most potent antibacterial activity with minimal inhibitory concentration values ranging from 6 to 96 μM, whereas compounds 2 and 6-9 showed moderate antibacterial activity. The presence of a β-hydroxyalkyl-γ-hydroxybutenolide subunit contributed significantly to antibacterial activity. Compounds 1-4 and 6-9 showed cytotoxic activities against the HCT-116 cancer cell line (1 < IC50s < 10 μM) and human fetal lung fibroblast MRC5 cell line (1 < IC50s < 10 μM for compounds 1, 2, 7, 8, and 9).

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Section: ■ Results and Discussionsupporting

confidence: 82%

Section: ■ Results and Discussionmentioning

confidence: 99%

Antibacterial Labdane Diterpenoids from Vitex vestita

Corlay

Lecsö-Bornet²,

Leborgne

et al. 2015

J. Nat. Prod.

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“…Dehydration of 24 with thionyl chloride gave exo-olefin 25, [20][21][22][23][24][25][26][27][28][29][30][31] which was subjected to allylic oxidation with SeO 2 32) to provide allylic alcohol 23. The subsequent 5-exo-tet iodolactonization of 23 with N-iodosuccinimide (NIS) proceeded smoothly and stereoselectively to afford the desired iodolactone 26.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Structural Revision of Cyslabdan

Ohtawa

Hishinuma

Takagi

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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Cyslabdan was isolated from the culture broth of Streptomyces sp. K04-0144 as a new potentiator of imipenem activity against methicillin-resistant Staphylococcus aureus. We accomplished the synthesis of cyslabdan according to a previously reported structure. However, we subsequently found that this structure was incorrect; our analysis of natural cyslabdan showed that it possessed R stereochemistry at the C8 position, not S, as had previously been reported. Thus, we completed the protecting-group-free synthesis of the correct structure of cyslabdan, which is described herein.

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“…The structure of this diterpene was thus elucidated as (12R)-hydroxylabda-8(17),13-dien-15(16)-olide and was named curcucomosin C. It should be noted that compound 3 has been reported as an intermediate in the synthesis of a labdane diterpene, but no details were provided. 22 The orientation of the furan ring in the diterpene 4 was confirmed on the basis of NOE difference experiments (data not shown). Thus, irradiation at the H-11 frequency resulted in enhancement of the H-14 signal and vice versa.…”

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confidence: 84%

Labdane Diterpenes from the Aerial Parts of Curcuma comosa Enhance Fetal Hemoglobin Production in an Erythroid Cell Line

et al. 2010

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Three new labdane diterpenes, curcucomosins A-C (1-3), four known labdane diterpenes, 4-7, and a known diarylheptanoid, 8, were isolated from the aerial parts of Curcuma comosa. The structures of the new diterpenes were elucidated by spectroscopic data analysis. The fetal hemoglobin (Hb F) induction potency of the isolated compounds was examined using a K562 reporter cell line harboring the enhanced green fluorescence protein (EGFP) gene under the control of a (G)gamma-globin promoter. Compound 6, isocoronarin D, exhibited the highest Hb F induction effect of 1.6-fold at 20 microM.

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Synthesis and Stereochemistry of the Antitumor Diterpenoid (+)-Zerumin B

Cited by 46 publications

References 16 publications

Antibacterial Labdane Diterpenoids from Vitex vestita

Antibacterial Labdane Diterpenoids from Vitex vestita

Synthesis and Structural Revision of Cyslabdan

Labdane Diterpenes from the Aerial Parts of Curcuma comosa Enhance Fetal Hemoglobin Production in an Erythroid Cell Line

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