Voratins A–C: Pyridinium Alkaloids from the Marine Dinoflagellate Effrenium voratum with Inhibitory Effects on Biomarkers for Benign Prostatic Hyperplasia

Abstract

Three voratin compounds (1−3) were isolated from the symbiotic marine dinoflagellate Ef f renium voratum. The planar structures of 1−3 were determined by 1D and 2D NMR spectroscopy and HRESIMS, and the relative and absolute configurations were established using ROESY correlations, Mosher's method, and quantum calculations. All of the compounds are zwitterionic and contain a dihydroindolizinium ring and a spiroketal moiety. Compounds 1−3 were found to exhibit therapeutic effects against benign prostatic hyperplasia (BPH), as evaluated using testosterone propionate-treated LNCap and RWPE-1 human prostate cells. This excellent activity suggests that 1−3 are promising for the development of BPH treatments.

Effect of Gynerium sagittatum methanol extract on testosterone-induced benign prostatic hyperplasia in rats compared with finasteride.

“…SIN therapy significantly reduced protein expression of Bcl-2 and PCNA in the PG tissues of mice with TP-induced BPH in vivo, indicating that SIN treatment alleviated BPH via the apoptotic pathway, which was consistent with in vitro data. These findings suggest that SIN treatment may improve BPH via the apoptotic pathway [32,33]. Inflammation is another mechanism for the development of BPH, which is also an important clue.…”

Marine natural products

“…Voratins A-C 869-871 are spiro-cyclic compounds from Effrenium voratum, a symbiotic dinoagellate associated with the coral Alveopora japonica. 309 while an anti-fungal amphidinol congener 872 was reported from an Irish isolate of Amphidinium carteri. 310 Ovataline 873 is a linear carbohydrate-bearing polyketide isolated from cultures of a Korean strain of Ostreopsis ovata, the absolute stereo-structure of which was assigned using standard methodologies.…”

“…Voratins A–C 869 – 871 are spiro-cyclic compounds from Effrenium voratum , a symbiotic dinoflagellate associated with the coral Alveopora japonica . 309 while an anti-fungal amphidinol congener 872 was reported from an Irish isolate of Amphidinium carteri . 310…”