Cladieunicellins K and L, New Eunicellin-Based Diterpenoids from an Octocoral Cladiella sp.

Shih, Frank Y.; Chen, Tsung-Hung; Lu, Mei‐Chin; Chen, Wu-Fu; Wen, Zhi‐Hong; Kuo, Yueh‐Hsiung; Sung, Ping‐Jyun

doi:10.3390/ijms141121781

Cited by 19 publications

(18 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An HMBC cross-peak was observed between the proton at δ 4.03 and the carbon at δ 74.8 ppm. However, no COSY correlation was observed between the two oxymethine signals suggesting that the dihedral angle between the two protons should be around 90° [18]. These data were consistent with a vicinal diol, with one hydroxyl group acylated and the other one linked to a sugar moiety [19,20].…”

Section: Resultsmentioning

confidence: 91%

Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens

et al. 2016

View full text Add to dashboard Cite

Among marine organisms, sponges are the richest sources of pharmacologically-active compounds. Stemming from a previous lead discovery program that gathered a comprehensive library of organic extracts of marine sponges from the off-shore region of Portugal, crude extracts of Erylus cf. deficiens collected in the Gorringe Bank (Atlantic Ocean) were tested in the innovative high throughput screening (HTS) assay for inhibitors of indoleamine 2,3-dioxygenase (IDO) and showed activity. Bioassay guided fractionation of the dichloromethane extract led to the isolation of four new glycolipids, named erylusamide A–D. The structures of the isolated compounds were established by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and chemical derivatization. The metabolites shared a pentasaccharide moiety constituted by unusual highly acetylated d-glucose moieties as well as d-xylose and d-galactose. The aglycones were unprecedented long chain dihydroxyketo amides. Erylusamides A, B and D differ in the length of the hydrocarbon chain, while erylusamide C is a structural isomer of erylusamide B.

show abstract

Section: Resultsmentioning

confidence: 91%

Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens

et al. 2016

View full text Add to dashboard Cite

show abstract

“…(family Alcyoniidae) collected in Taiwan waters [1,2,3]. Because of our interest in the chemistry of new natural products, the continuing investigation on the chemical constituents of the soft coral Cladiella sp.…”

Section: Introductionmentioning

confidence: 99%

Cladieunicellins M–Q, New Eunicellins from Cladiella sp.

Chen

Wen

et al. 2014

Marine Drugs

Self Cite

View full text Add to dashboard Cite

Five new 7α-hydroxyeunicellin-based diterpenoids, designated as cladieunicellins M–Q (1–5), were isolated from a Formosan octocoral Cladiella sp. The structures of 1–5 were elucidated on the basis of spectroscopic methods and by comparison of the data with those of the related metabolites. Cytotoxicity of metabolites 1–5 against the human leukemia Molt 4 and HL 60 is also described. Among them, compounds 1, 3 and 5 exhibited moderate cytotoxicity toward Molt 4 cells with IC50 values 16.43, 14.17 and 15.55 μM, respectively. Preliminary SAR (structure activity relationship) information was obtained from these compounds and their analogues.

show abstract

“…Soft corals of the genus Cladiella have been known to be rich sources of eunicellin-type metabolites and several bioactivities of these compounds have been studied [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. Our previous studies on the soft coral Cladiella krempfi have resulted in the isolation of a series of new eunicellin-based diterpenoids, krempfielins A–P [ 15 , 16 , 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

“…Our contineous investigation on the chemical constituents of soft coral C . krempfi has afforded two new compounds, krempfielins Q and R ( 1 and 2 in Chart 1 ), and one minor known compound cladieunicellin K ( 3 ) [ 11 ]. The molecular structures of 1 and 2 , including the relative configurations, were established by the detailed spectroscopic analysis and by comparison with related physical and spectral data of known compound, krempfielin E ( 4 ) [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Krempfielins Q and R, Two New Eunicellin-Based Diterpenoids from the Soft Coral Cladiella krempfi

Tai

Uvarani

Cheng

et al. 2014

IJMS

Self Cite

View full text Add to dashboard Cite

Two new eunicellin-based diterpenoids, krempfielins Q and R (1 and 2), and one known compound cladieunicellin K (3) have been isolated from a Formosan soft coral Cladiella krempfi. The structures of these two new metabolites were elucidated by extensive spectroscopic analysis. Anti-inflammatory activity of new metabolites to inhibit the superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (FMLP/CB)-induced human neutrophil cells and cytotoxicity of both new compounds toward five cancer cell lines were reported.

show abstract

Cladieunicellins K and L, New Eunicellin-Based Diterpenoids from an Octocoral Cladiella sp.

Abstract: Two new eunicellin-based diterpenoids, cladieunicellins K (1) and L (2), were isolated from an octocoral Cladiella sp. The structures of 1 and 2 were elucidated by spectroscopic methods and 2 exhibited moderate cytotoxicity towards the MOLT-4 human leukemia.

Cited by 19 publications

References 7 publications

Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens

Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens

Cladieunicellins M–Q, New Eunicellins from Cladiella sp.

Krempfielins Q and R, Two New Eunicellin-Based Diterpenoids from the Soft Coral Cladiella krempfi

Contact Info

Product

Resources

About