Sesquiterpenes from the Hainan Sponge Dysidea septosa

Abstract

Five new sesquiterpenes, named lingshuiolides A (1) and B (2), lingshuiperoxide (6), isodysetherin (10), and spirolingshuiolide (12), along with several known related analogues (7- 9, 11, and 13- 15), were isolated from the Hainan marine sponge Dysidea septosa. The structures of new compounds 1, 2, 6, 10, and 12 were determined by detailed analysis of 1D and 2D NMR spectra and by comparison with related model compounds. The absolute configuration of lingshuiolide B (2) was established by using the modified Mosher's method. Spirolingshuiolide (12) represents the first example of a sesquiterpene with a rearranged drimane skeleton. Compounds 7- 9 and 15 exhibited significant inhibitory activity against human protein tyrosine phosphatase 1B (hPTP1B), an enzyme involved in the regulation of insulin signaling. In particular, 15 showed the most potent effect, with an IC 50 value of 1.9 microg/mL.

Natural products possessing protein tyrosine phosphatase 1B (PTP1B) inhibitory activity found in the last decades

“…Lactone 202 showed strong inhibitory activity with an IC 50 value of 1.58 μmol/L. Further studies on several species of Dysidea from Hainan produced other sesquiterpene PTP1B inhibitors, such as 203-206 from D septosa [132] , and 207 and 208 from D villosa [133] . Sesquiterpene 203 had the strongest inhibitory effect among 203-206 [132] .…”

“…Further studies on several species of Dysidea from Hainan produced other sesquiterpene PTP1B inhibitors, such as 203-206 from D septosa [132] , and 207 and 208 from D villosa [133] . Sesquiterpene 203 had the strongest inhibitory effect among 203-206 [132] . Compound 207, a member of the family of sesquiterpene quinine derivatives with a further rearranged drimane skeketon characterized by the abnormal position of the quinine moiety, showed moderate inhibitory activity and moderate cytotoxicity against HeLa cell lines.…”

Living inside a sponge skeleton: the association of a sponge, a macroalga and a diatom

“…because of the production of deterrent chemical compounds) (Boney 1972;da Cruz et al 2012), or if they could enhance the energetic value of the sponge tissues. Sponges belonging to the genus Dysidea contain several bioactive molecules (Agena et al 2009;De Caralt et al 2013;Huang et al 2008;Venkateswarlu et al 1998), which are often produced by symbiotic cyanobacteria (Becerro and Paul 2004). Studies on these photosynthetic organisms have gained much attention since cyanobacteria have potential applications in biotechnology (Abed et al 2009), while there are no researches on the production of natural products associated with endozoic algae.…”

Bioactive natural products from Chinese marine flora and fauna

“…Thus, the substances of the mangrove plant Excoecaria agallocha L (Euphorbiaceae family for the first time) were investigated, which led to the isolation of four diterpenes with an unprecedented skeleton, named excoagallochaols A-D (26-29) [26] ( Figure 6). In addition to these terpenes, a novel octacyclic alkaloid with an unusual scaffold, suffruticosine (30), was isolated from Securinega suffruticosa (Pall) Rehd in the same family [27] ( Figure 6). The absolute configuration of suffruticosine (30) was determined on the basis of CD spectral analysis.…”

“…For instance, five new sesquiterpenes, lingshuiolides A and B (37 and 38), lingshuiperoxide (39), isodysetherin (40), and spirolingshuidolide (41) were isolated from the Hainan sponge Dysidea septosa [30] (Figure 7). The absolute configuration of lingshuiolide B (38) was established by using a modified Mosher's method.…”