First asymmetric synthesis of the marine furanosesterterpene natural product, (18S)-variabilin, employing enzymatic desymmetrization of propanediol derivatives

Takabe, Kunihiko; Hashimoto, Hiroo; Sugimoto, Hideki; Nomoto, Masaru; Yoda, Hidemi

doi:10.1016/j.tetasy.2004.01.031

Cited by 34 publications

(27 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…178 182 The first asymmetric synthesis of the marine furanosesterterpene tetronic acid 18S-variabilin 256, from the sponge Ircinia variabilis, has been reported. 183 An efficient and stereodefined process is employed, featuring lipase-catalyzed asymmetric desymmetrization of two types of propanediol precursors incorporating the terpene skeleton. Eight cytotoxic furanosesterterpenoids, namely ircinins 1and 2, sacotins D 260 and E 261, 166 sacotins G 262 and H 263, 125 (7E,12E,18R,20Z)-variabilin, and (8E,13Z,18R,20Z)-strobilinin, 138 were reported from a specimen of Sarcotragus sp.…”

Section: Furanoditerpenoidsmentioning

confidence: 99%

Heterocyclic Terpenes: Linear Furano‐ and Pyrroloterpenoids

Wang

et al. 2006

ChemInform

View full text Add to dashboard Cite

show abstract

Section: Furanoditerpenoidsmentioning

confidence: 99%

Heterocyclic Terpenes: Linear Furano‐ and Pyrroloterpenoids

Wang

et al. 2006

ChemInform

View full text Add to dashboard Cite

show abstract

“…Two selected fractions (40 mg and 60 mg) from this column containing sarcotin A ( 2 ) [16, 42] and variabilin ( 3 ) [43, 44], respectively, were further subjected to preparative TLC purification to give pure 2 [15.5 mg; [ α ] D + 28.0 ( c = 7.7, CHCl 3 ); and [ α ] D + 17.5 ( c = 7.7, MeOH)] and 3 [21.3 mg; [ α ] D − 21.5 ( c = 1.5, CHCl 3 ); and [ α ] D − 10.5 ( c = 1.5, MeOH)].…”

Section: Methodsmentioning

confidence: 99%

“…All isolated compounds were identified by comparison of their spectral data (see Supplementary Material, available online at http://dx.doi.org/10.1155/2016/5318176) with the literature values [16, 26, 39–44]. …”

Section: Methodsmentioning

confidence: 99%

In VitroGrowth Inhibitory Activities of Natural Products from Irciniid Sponges against Cancer Cells: A Comparative Study

Romdhane

Elbour

Carbone

et al. 2016

BioMed Research International

View full text Add to dashboard Cite

Marine sponges of the Irciniidae family contain both bioactive furanosesterterpene tetronic acids (FTAs) and prenylated hydroquinones (PHQs). Both classes of compounds are known for their anti-inflammatory, antioxidant, and antimicrobial properties and known to display growth inhibitory effects against various human tumor cell lines. However, the different experimental conditions of the reported in vitro bioassays, carried out on different cancer cell lines within separate studies, prevent realistic actual discrimination between the two classes of compounds from being carried out in terms of growth inhibitory effects. In the present work, a chemical investigation of irciniid sponges from Tunisian coasts led to the purification of three known FTAs and three known PHQs. The in vitro growth inhibitory properties of the six purified compounds have been evaluated in the same experiment in a panel of five human and one murine cancer cell lines displaying various levels of sensitivity to proapoptotic stimuli. Surprisingly, FTAs and PHQs elicited distinct profiles of growth inhibitory-responses, differing by one to two orders of magnitude in favor of the PHQs in all cell lines. The obtained comparative results are discussed in the light of a better selection of drug candidates from natural sources.

show abstract

“…The first asymmetric synthesis of the marine furanosesterterpene natural product, (18S)-variabilin, employed enzymatic desymmetrization of propanediol derivatives [158], Fig. (61).…”

Section: Prochiral Substratementioning

confidence: 99%