The new bioactive diterpenes cyanthiwigins E–AA from the Jamaican sponge Myrmekioderma styx

Peng, Jiangnan; Walsh, Kelly; Weedman, Valarie; Bergthold, Jennifer D.; Lynch, John K.; Lieu, Kuo Lee; Braude, Irwin A.; Kelly, Michelle; Hamann, Mark T.

doi:10.1016/s0040-4020(02)00937-7

Cited by 71 publications

(48 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[13][14][15][16][17][18] In the marine environments, this class of compounds have been reported from sponges of the genera Axinyssa, Epipolas, Higginsia, and Myrmekioderma as well as from a species of gliding bacterium. [19][20][21][22][23][24][25] However, none of these verrucosanes have a high level of oxygenated functionalities, as do those of the gagunins. In our continuing search for bioactive substances from marine organisms of Korea, we re-collected the same Phorbas sponge species, the organic extract of which showed considerable toxicity against brine shrimp larvae (LC 50 37 ppm).…”

mentioning

confidence: 99%

Polyoxygenated Diterpenes from the Sponge Phorbas sp.

et al. 2008

View full text Add to dashboard Cite

Ten new polyoxygenated diterpenes (7-16) along with six known gagunin compounds (1-6) were isolated from the sponge Phorbas sp. collected in the Korean Sea. On the basis of a combination of NMR and mass spectroscopic analyses, the molecular structures of these diterpenes, designated as gagunins H-Q, were determined to be penta- or hexa-oxygenated diterpenes of the 10,13-bis-epi-homoverrucosane class. A new diterpene acid (17) of a bisabolane-related skeletal class was also isolated and structurally defined by the spectroscopic analyses. These compounds exhibited moderate to significant cytotoxicity against the K-562 cell line as well as weak inhibitory activity against isocitrate lyase (ICL).

show abstract

mentioning

confidence: 99%

Polyoxygenated Diterpenes from the Sponge Phorbas sp.

et al. 2008

View full text Add to dashboard Cite

show abstract

“…Reiswigin A (a potent anti-herpes virus marine terpenoid), 7 cyanthiwigin E (a potent anti-tumor marine terpenoid), 8 and aragusterol A (a potent anti-tumor marine steroid) 9 are just some examples that have been reported (Fig. 2).…”

Section: Introductionmentioning

confidence: 98%

“…The reaction mixture was diluted with Et 2 O and then filtered through a silica gel pad. Removal of the solvent gave a residue, which was purified by silica gel column chromatography (hexane/AcOEt¼9:1) to generate epoxyiodide 5 (38 8. mg, 89% yield) as a colorless oil.…”

mentioning

confidence: 99%

Stereocontrolled one-pot synthesis of cycloalkane derivatives possessing a quaternary carbon using allyl phenyl sulfone

et al. 2009

View full text Add to dashboard Cite

“…Members of the cyathane family are each related by a characteristic 5-6-7 tricarbocyclic fused-core structure, derived from the cyclization of geranylgeranyl diphosphate [3]. While many of the cyathanes display antibacterial/antimicrobial activity or have cytotoxic activity against human cancer cell lines [1,2,[22][23][24], their most exciting therapeutic potential is derived from their ability to induce nerve growth factor release from glial cells [13-15, 17, 19, 20].…”

Section: Introductionmentioning

confidence: 99%

“…The cyrneines [17] are produced by Sarcodon cyrneus. The cyanthiwigins [9,[22][23][24] are products of the marine sponges Epipolasis reiswigi and Myrmekioderma styx binds to basal forebrain cholinergic neurons (the neurons associated with AD) and promotes their survival. Recent preclinical and clinical AD studies have revealed a significant reduction of neuronal loss and a reduced rate of cognitive decline with NGF therapy [6,30].…”

Section: Introductionmentioning

confidence: 99%

Bacteria-induced static batch fungal fermentation of the diterpenoid cyathin A3, a small-molecule inducer of nerve growth factor

Dixon

Schweibenz

Hight

et al. 2010

J Ind Microbiol Biotechnol

View full text Add to dashboard Cite

Cyathin A(3), produced by the fungus Cyathus helenae, is a member of the cyathane family of diterpene natural products. While many of the cyathanes display antibacterial/antimicrobial activity or have cytotoxic activity against human cancer cell lines, their most exciting therapeutic potential is derived from their ability to induce nerve growth factor (NGF) release from glial cells, making the cyathanes attractive lead molecules for the development of neuroprotective therapeutics to prevent/treat Alzheimer's disease. To investigate if cyathin A(3) has NGF-inducing activity, we set out to obtain it using published C. helenae bench-scale fungal fermentations. However, to overcome nonproducing fermentations, we developed an alternative, bacteria-induced static batch fermentation approach to the production of cyathin A(3), as described in this report. HPLC, UV absorption spectra, and mass spectrometry identify cyathin A(3) in fungal fermentations induced by the timely addition of Escherichia coli K12 or Bacillus megabacterium. Pre-filtration of the bacterial culture abolishes cyathin A(3) induction, suggesting that bacteria-associated media changes or physical interaction between the fungus and bacteria underlie the induction mechanism. Through alteration of incubation conditions, including agitation, the timing of induction, and media composition, we optimized the fermentation to yield nearly 1 mg cyathin A(3)/ml media, a sixfold increase over previously described yields. Additionally, by comparison of fermentation profiles, we reveal that cyathin A(3) biosynthesis is regulated by carbon catabolite repression. We have used an enzyme-linked immunosorbent assay to illustrate that cyathin A(3) induces NGF release from cultured glial cells, and therefore cyathin A(3) warrants further examination in the development of neuroprotective therapeutics.

show abstract

The new bioactive diterpenes cyanthiwigins E–AA from the Jamaican sponge Myrmekioderma styx

Cited by 71 publications

References 12 publications

Polyoxygenated Diterpenes from the Sponge Phorbas sp.

Polyoxygenated Diterpenes from the Sponge Phorbas sp.

Stereocontrolled one-pot synthesis of cycloalkane derivatives possessing a quaternary carbon using allyl phenyl sulfone

Bacteria-induced static batch fungal fermentation of the diterpenoid cyathin A3, a small-molecule inducer of nerve growth factor

Contact Info

Product

Resources

About