Topic
Norzoanthamine
About: Norzoanthamine is a research topic. Over the lifetime, 52 publications have been published within this topic receiving 1167 citations.
Papers published on a yearly basis
Papers
TL;DR: This work reports the stereoselective total synthesis of norzoanthamine in 41 steps, with an overall yield of 3.5% (an average of 92% yield each step).
Abstract: Norzoanthamine, an alkaloid isolated from Zoanthus sp., can suppress the loss of bone weight and strength in ovariectomized mice. Norzoanthamine derivatives can also strongly inhibit the growth of P-388 murine leukemia cell lines and human platelet aggregation. However, norzoanthamine's densely functionalized complex stereostructure and scarce availability from natural sources have proved a synthetic challenge. We report the stereoselective total synthesis of norzoanthamine in 41 steps, with an overall yield of 3.5% (an average of 92% yield each step).
229 citations
99 citations
TL;DR: In this paper, the structures of newly isolated compounds from a colonial zoanthid Zoanthus sp. collected in the Amami Islands of Japan and their structures have been elucidated by detailed spectroscopic analysis and X-ray crystallographic analysis.
Abstract: Norzoanthamine, oxyzoanthamine, norzoanthaminone, cyc lozoanthamine and e p i n o r z o a n t h a m i n e have been isolated from a colonial zoanthid Zoanthus sp. collected in the Amami Islands of Japan and their structures have been elucidated by detailed spectroscopic analysis and X-ray crystallographic analysis. In our continuing search for physiologically active substances from marine organisms (1), we found five novel cytotoxic a lka lo ids , no rzoan thamine , o x y z o a n t h a m i n e , n o r z o a n t h a m i n o n e , cyc lozoan thamine and epinorzoanthamine from the genus Zoanthus on the Ayamaru coast of the Amami Islands. They inhibited growth of P388 murine leukemia cells with IC50 values of 24, 7.0, 1.0, 24 and 2.6 μg/ml1 respectively. Although a couple of zoanthamine derivatives possessing the unique heterocycles has been already reported (2), we wish to report herein the isolation and structures of newly isolated compounds of this series. The wet specimens (5.0 kg) which occurred as dense mat were minced by a Waring blender and extracted with ethanol. The ethanolic extract was filtered and concentrated in vacuo. The aqueous residue was partitioned between ethyl acetate and water, and the water layer was subsequently extracted twice with ethyl acetate. The lipid-soluble extracts were chromatographed on silica gel (eluted with chloroform containing methanol), followed to be separated by preparative TLC on S1O2 with acetonitri le, diethyl ether or ethyl acetate as solvent, giving zoanthamine 1 ( 6 . 3 X 10\" %) , norzoanthamine 2 as a colorless crystal [21 mg, 4.2 X 10\" %, mp. 282~285°C; [A]D 1.6° (c, 1.0, CHCI3)], oxyzoanthamine 3 [9.1 mg, 1.8 χ 1 0 \" 6 % , [
95 citations
TL;DR: Norzoanthamine hydrochloride, which suppresses the decrease in bone weight and strength in ovariectomized mice, could be a good candidate for an osteoporotic drug.
Abstract: Norzoanthamine is a zoanthamine-type alkaloid from the colonial zoanthid Zoanthus sp. Norzoanthamine hydrochloride, which suppresses the decrease in bone weight and strength in ovariectomized mice, could be a good candidate for an osteoporotic drug. Although the relative configuration of norzoanthamine was established based on an X-ray crystallographic analysis, the absolute stereochemistry of norzoanthamine remains unclear. To investigate their biogenesis and mechanisms of biological action, we conducted chemical and spectroscopic studies to determine the absolute configuration of norzoanthamines.
76 citations
TL;DR: Norzoanthamine hydrochloride significantly suppressed the decrease in femoral weight and bone biomechanical parameters caused by ovariectomy without an increase in uterine weight, suggesting it may act as both a suppressor of bone resorption and an enhancer of bone formation in vivo.
Abstract: Norzoanthamine is an alkaloid isolated from a colonial zoanthid We examined the effects of norzoanthamine hydrochloride on bone weight, strength and morphology in ovariectomized mice, a postmenopausal osteoporosis model Norzoanthamine hydrochloride significantly suppressed the decrease in femoral weight and bone biomechanical parameters caused by ovariectomy without an increase in uterine weight This means that norzoanthamine hydrochloride does not have an estrogen-like effect on reproductive organs Morphological observations of longitudinally ground sections of the humeri showed that norzoanthamine hydrochloride administration (2 mg/kg/d, po) completely suppressed the loss of trabecular bone Furthermore, norzoanthamine hydrochloride thickened the cortical bone Based on these results, norzoanthamine hydrochloride may act as both a suppressor of bone resorption and an enhancer of bone formation in vivo
74 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2021 | 2 |
| 2020 | 1 |
| 2018 | 1 |
| 2017 | 1 |
| 2016 | 1 |
| 2014 | 4 |