A sesquiterpene thiocyanate and three sesquiterpene isothiocyanates from the sponge Trachyopsis aplysinoides

He, Hai Yin; Faulkner, D. John; Shumsky, Jay S.; Hong, Ki Bum; Clardy, Jon

doi:10.1021/jo00272a008

Cited by 66 publications

(49 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An NOE correlation we observed for 4 from H-6 to H 3 -14, shown in Figure 1, can be used to rule out the latter two. Consistent with the literature, 10 we observed other key NOE enhancements ( With the stereochemistry of 4 defined above, there were now three possibilities to be considered for 5: 2S, 5S, 10S; 2S, 5R, 10S; or 2R, 5S, 10S. The important NOE correlation observed in 4 from H-6 to H 3 -14 was not in the data set for 5, which allowed elimination of the first possibility listed above.…”

Section: Resultssupporting

confidence: 88%

See 1 more Smart Citation

Stereochemical challenges in characterizing nitrogenous spiro-axane sesquiterpenes from the Indo-Pacific sponges Amorphinopsis and Axinyssa

Wegerski¹,

Sonnenschein²,

Cabriales³

et al. 2006

Tetrahedron

View full text Add to dashboard Cite

An investigation was conducted to identify the structures and bioactive properties of five compounds isolated from the Halichondrida sponges Amorphinopsis foetida and Axinyssa aplysinoides. All compounds possessed the spiro-axane sesquiterepene core and all were substituted at C-2 with nitrogen containing functionality. The stereochemistry of one known compound has been revised to (2R,5R,10S)-2-formamido-6-axene (3). It exhibited mild selective solid tumor and mild antibacterial activity and was found from Axinyssa. A second known substance whose stereochemistry has also been revised, (2R,5R,10S)-2-isothiocyanato-6-axene (4) plus its undescribed diastereomer (5) were isolated from Amorphinopsis. Both sponges were the source of two new N-phenethyl-2-formamido-6-axene diastereomeric compounds (6) and (7). No solid tumor or antibacterial activity was found for 4 -7.

show abstract

Section: Resultssupporting

confidence: 88%

“…Described below are properties of five compounds obtained including the known substances, 2-formamido-6-axene (3), and 2-isothiocyanato-6-axene (4), 10 its undescribed diastereomer 5, and a set of new diastereomeric compounds, N-phenethyl-2-formamido-6-axenes 6 and 7. …”

Section: Introductionmentioning

confidence: 99%

Stereochemical challenges in characterizing nitrogenous spiro-axane sesquiterpenes from the Indo-Pacific sponges Amorphinopsis and Axinyssa

Wegerski¹,

Sonnenschein²,

Cabriales³

et al. 2006

Tetrahedron

View full text Add to dashboard Cite

show abstract

“…The isolation of prepsammaplin A (155), a cysteine dimer, indicated that cysteine might be the precursor of the central part of psammaplin A. Interestingly, the R functional groups of psammaplin B (156) and C (157) are unique and do not appear to have counterparts among any known marine sponge amino acid derivatives (110). Additionally, the only precedent of the thiocyanate group, as found in psammaplin B (156), is the sesquiterpene thiocyanate isolated from the sponge Trachyopsis aplysinoides (111).…”

Section: Oxime-histamines-ianthellinmentioning

confidence: 99%

The Marine Bromotyrosine Derivatives

Peng¹,

Jing²,

Hamann³

2005

The Alkaloids: Chemistry and Biology

101

View full text Add to dashboard Cite

“…[Molinski et al (1987)] "Eplpolasls" kushlmotoensls [Tada and Yasuda (1985)] Ciocalypta sp..l: ; Gulavita et al (1986); Hagadone et aZ (1979); Karuso et aL (1989); Tada and Yasuda (1985)} "Stylotella" sp. § [Pais et al (19~7)] = Axlnyssa aplysinoldes 7rachyops~s aplyslholdes [He et aL (1989)] Halichondrla sp. [Burreson etal.…”

Section: H2n/~ N CI 39 Girollinementioning

confidence: 99%

Chemotaxonomy of Agelas (Porifera: Demospongiae)

Braekman¹,

Daloze²,

Stoller³

et al. 1992

Biochemical Systematics and Ecology

View full text Add to dashboard Cite

Chemotaxonomy of the genus AgelasBraekman, J.C.; Stoller, C.; van Soest, R.W.M. Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. Download date: 09 May 2018Biochemical Systernatics and Ecology, Vol. 20. No. 5. pp, 417-431, 1992 Abstract--The secondary metabolite content of four different species of Agelas (Porifera) from the West Indies has been studied. All the compounds isolated are already known metabolites whose identification was confirmed by comparison of their spectral properties with those reported in the literature. They pertain to two different classes of compounds: terpenoids and pyrrole-2-carboxylic acid derivatives. The chemotaxonomic value of these secondary metabolites has been evaluated. Their distribution amongst the Porifera, as well as that of isocyanide derivatives, suggests a close relationship between the Agelasidae, the Axinellidae and the Halichondriidae.

show abstract

A sesquiterpene thiocyanate and three sesquiterpene isothiocyanates from the sponge Trachyopsis aplysinoides

Cited by 66 publications

References 1 publication

Stereochemical challenges in characterizing nitrogenous spiro-axane sesquiterpenes from the Indo-Pacific sponges Amorphinopsis and Axinyssa

Stereochemical challenges in characterizing nitrogenous spiro-axane sesquiterpenes from the Indo-Pacific sponges Amorphinopsis and Axinyssa

The Marine Bromotyrosine Derivatives

Chemotaxonomy of Agelas (Porifera: Demospongiae)

Contact Info

Product

Resources

About