Natural Products from Marine Heterobranchs: an Overview of Recent Results

Heterobranchs are a fascinating group of marine mollusks that are recognized as an important source of bioactive natural products. Often, these molecules, which are either selected from the diet or de novo biosynthesized by the mollusks, play a fundamental role for their survival being utilized as defensive chemicals against predators. A summary of the studies carried out by our group, in the last decade, on heterobranchs is presented here. A number of new compounds exhibiting different molecular architectures have been chemically characterized. Some of them have also shown an interesting pharmacological potential. Some ecological studies that we conducted on selected species of heterobranchs are also reviewed

Cytosporin-related compounds from the marine-derived fungus Eutypella scoparia

[EN] Chemical investigation of the culture broth of the fungus Eutypella scoparia ICB-OBX, isolated from the marine pulmonate mollusc Onchidium sp., led to the finding of novel compounds 1 and 2, structurally related to angiotensin II binding inhibitors cytosporins, along with unrelated known nitrogen metabolites (compounds 3¿5). The structure and the relative stereochemistry of the novel metabolites were assigned mainly by a detailed analysis of two-dimensional NMR techniques whereas the absolute stereochemistry was proposed by modified Mosher's method. Compound 2 contains an unusual cyclic carbonate functionality that is rare among natural products.Ciavatta, ML.; López-Gresa, MP.; Gavagnin, M.; Nicoletti, R.; Manzo, E.; Mollo, E.; Guo, Y.... (2008). Cytosporin-related compounds from the marine-derived fungus Eutypella scoparia. Tetrahedron. 64(22):5365-5369. https://doi.org/10.1016/j.tet.2008.03.016S53655369642

An Alkaloid from a Highly Invasive Seaweed Increases the Voracity and Reproductive Output of a Model Fish Species

The invasive macroalga Caulerpa cylindracea has spread widely in the Mediterranean Sea, becoming a favorite food item for native fish for reasons yet unknown. By using a combination of behavioral, morphological, and molecular approaches, herein we provide evidence that the bisindole alkaloid caulerpin, a major secondary metabolite of C. cylindracea, significantly increases food intake in the model fish Danio rerio, influencing the regulation of genes involved in the orexigenic pathway. In addition, we found that the compound improves fish reproductive performance by affecting the hypothalamus-pituitary-gonadal axis. The obtained results pave the way for the possible valorization of C. cylindracea as a sustainable source of a functional feed additive of interest to face critical challenges both in aquaculture and in human nutrition

Occurence and Bioactivities of Funicone-Related Compounds

Studies on production of secondary metabolites by fungi have received a substantial boost lately, particularly with reference to applications of their biological properties in human medicine. Funicones represent a series of related compounds for which there is accumulating evidence supporting their possible use as pharmaceuticals. This paper provides a review on the current status of knowledge on these fungal extrolites, with special reference to aspects concerning their molecular structures and biological activities

SYNTHETIC STRATEGY FOR THE PREPARATION OF BIOACTIVE GALACTOGLYCEROLIPIDS

The current communication represents an extended abstract of the presentation delivered on the joint Moldo-Italian seminar “New frontiers in natural product chemistry”, held in the Institute of Chemistry, Academy of Sciences of Moldova on 30 September. A simple and efficient strategy for the synthesis of galactoglycerolipids is provided

Tetranorditerpenes from Detarium microcarpum

Abstract: The chloroform extract of Detariummicrocarpum afforded two tetranorditerpenes, 1-naphthaleneacetic-5-carboxy-1,2,3,4,4a,7,8,8a-octahydro- 1,2,4a-trimethyl acid and 1-naphthaleneacetic-7-oxo-1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl acid, together with a clerodane diterpene, 2-oxo-kolavenic acid. New spectroscopic data are reported for the two rare tetranorditerpenes

Production and fungitoxic activity of Sch 642305, a secondary metabolite of Penicillium canescens

[EN] Production of fungitoxic extrolites was evaluated in culture filtrates of several isolates belonging to Penicillium canescens and P. janczewskii that showed some extent of inhibitory activity against the plant pathogenic fungus Rhizoctonia solani. In addition to griseofulvin and dechlorogriseofulvin that are already known in these species, curvulinic acid, previously unreported in Penicillium, was produced by all isolates assayed. Another extrolite recently characterized from a P. verrucosum strain by the name of Sch 642305 was detected in 5 isolates of P. canescens only. The purified compound completely inhibited mycelial growth of isolates of Rhizoctonia solani and other plant pathogenic fungi in vitro. The role of this extrolite as a possible biochemical determinant of antagonism toward plant pathogenic fungi, and implications concerning chemotaxonomy are discussed.Nicoletti, R.; Lopez-Gresa, MP.; Manzo, E.; Carella, A.; Ciavatta, ML. (2007). 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First Occurrence of Megastigmane Glucosides in a Plant of Retama Genus

Chemical investigation of Retama sphaerocarpa collected in Algeria resulted in the isolation of two megastigmane glucosides, compounds 1 and 2, along with a series of isoflavones and phenol derivatives. Compound 1, named retamoside, was new and its structure was determined by extensive application of spectroscopic methods, including HRMS, 1D and 2D NMR and CD. The anti-inflammatory properties of co-occurring main megastigmane, saurobaccioside B (2) and structurally related vomifoliol (3) on LPS-stimulated murine macrophages RAW 274.7 have been evaluated

Exploring the Chemical Diversity of Algerian Plants: Three New Pentacyclic Triterpenoids from Launaea acanthoclada Roots

The chemical study of Launaea acanthoclada from South-East Algeria led to the isolation of twelve oxygenated terpenoid compounds, including three new pentacyclic triterpenoids 1–3 with either lupane or ursane rearranged skeletons. The structure and the stereochemistry of these compounds were established by spectroscopic methods, including NMR techniques. The chemical pattern of L. acanthoclada is in accordance with the triterpenoid scenario of the genus Launaea embracing to date lupane, oleane, ursane and taraxastane skeletons. However, the carbon frameworks exhibited by new compounds 1–3 have never been reported from Launaea species