Abstract
One new pentacyclic sesterterpene, hippospongide A (1), and one new scalarane sesterterpenoid, hippospongide B (2), along with six previously reported known scalarane–type sesterterpenes (3–8), were isolated from a sponge Hippospongia sp. The structures of these compounds were elucidated on the basis of their spectroscopic data and comparison of the NMR data with those of known analogues. These metabolites are the first pentacyclic sesterterpene and scalarane-type sesterterpenes to be reported from this genus. Compounds 3–5 exhibited significant cytotoxicity against DLD-1, HCT-116, T-47D and K562 cancer cell lines.
Highlights
IntroductionScalarane sesterterpenoids have been identified from sponges and nudibranchs [1]
In previous reports, scalarane sesterterpenoids have been identified from sponges and nudibranchs [1].Research into the pharmacological properties of this class of natural products is of particular interest.many scalarane metabolites show a variety of biological activities, such as antimicrobial, cytotoxic, antifeedant, ichthyotoxic, anti-inflammatory, antitubercular, platelet aggregation inhibition, RCE-protease inhibition and nerve growth factor synthesis-stimulating [1]
After determining the structure of 1, we discovered that its molecular framework has been obtained as known sesterterpenoids salmahyrtisol A and similan A, which were isolated previously from sponges
Summary
Scalarane sesterterpenoids have been identified from sponges and nudibranchs [1]. Research into the pharmacological properties of this class of natural products is of particular interest. Many scalarane metabolites show a variety of biological activities, such as antimicrobial, cytotoxic, antifeedant, ichthyotoxic, anti-inflammatory, antitubercular, platelet aggregation inhibition, RCE-protease inhibition and nerve growth factor synthesis-stimulating [1]. Our investigation of the chemical constituents of a sponge Hippospongia sp. (Figure 1) yielded one new pentacyclic sesterterpene, hippospongide A (1), and one new scalarane sesterterpenoid, hiposppongide B (2), along with six known sesterterpenoids, heteronemin (3) [2], heteronemin acetate (4) [3], hyrtiosin E (5) [4], 12-deacetoxyscalarin 19-acetate (6) [5], hyrtiosal (7) [6] and scalarafuran (8) [7]. The cytotoxicity of metabolites 1–8 against human colon adenocarcinoma (DLD-1 and HCT-116), hormone-dependent breast cancer (T-47D) and human chronic myelogenous leukemia (K562) cell lines was evaluated
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