Search for new compounds and biologically active substances from Chinese marine organisms

Zeng, Lang; Su, Jingyu; Zhong, Yong‐Li; Fu, X.; Peng, Tang‐Sheng; Zhu, Yugui; Meng, Yanhui; Cen, Ying-Zhou; Xu, Xiaohua; Zheng, Yaohua; Wang, Gui-Yang-Sheng

doi:10.1351/pac199971061147

Cited by 11 publications

(3 citation statements)

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“…The melting points were determined using an X-6 micromelting point apparatus and are uncorrected. 1 H and 13 CNMR spectra were recorded at 500 and 125 MHz, respectively, in CDCl3 using TMS as internal standard. Optical rotations were measured on a Schmidt+Haensch Polaptronic hnqw5 polarimeter.…”

Section: Methodsmentioning

confidence: 99%

“…In the course of our study on the chemical constituents of soft corals, we have isolated many chemically and biologically interesting secondary metabolites. − Among them, two tetraterpenoids, named methyl sartortuoate ( 3 ) and methyl isosartortuoate ( 4 ), from the soft coral Sarcophyton tortuosum were structurally the most interesting compounds. After inspection of the structures of 3 and 4 , we proposed that this unique framework might be derived from Diels−Alder addition of two cembranoid units as precursors.…”

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confidence: 99%

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Two New Cytotoxic Tetracyclic Tetraterpenoids from the Soft Coral Sarcophyton tortuosum

Zeng

Lan

et al. 2004

J. Nat. Prod.

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Two new cytotoxic tetracyclic tetraterpenoids, methyl tortuoate A (1) and methyl tortuoate B (2), along with the known methyl sartortuoate (3) were isolated from the soft coral Sarcophyton tortuosum. The structures of 1 and 2 were established by spectroscopic methods, mainly on the basis of 2D NMR techniques, and were confirmed by single-crystal X-ray diffraction analysis. The cytotoxic activities of these compounds were carried out in vitro on human nasophyringeal carcinoma (CNE-2) and murine lymphocytic leukemia (P-388) tumor cell lines.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Two New Cytotoxic Tetracyclic Tetraterpenoids from the Soft Coral Sarcophyton tortuosum

Zeng

Lan

et al. 2004

J. Nat. Prod.

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“…However, in the Conus case, hydrogen bonding is directed toward increasing binding strength and selectivity toward their neuronal targets. Polyhydroxylation is a recurrent feature in natural products of marine and land origins. − Polyhydroxylated compounds, ranging from Taxol to Dermostatin, rely on the hydrogen-bonding capabilities of their hydroxyl groups to interact with their molecular targets. In the case of most polyhydroxylated natural products, their complex molecular scaffolds are the product of an intricate multienzymatic biosynthetic pathway that incorporates diverse metabolites in manners unique to the organisms that produce the compounds.…”

Section: Resultsmentioning

confidence: 99%

Polypeptide Chains Containingd-γ-Hydroxyvaline

et al. 2005

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Life has an unexplained and distinct l-homochirality. Proteins typically incorporate only l-amino acids into their sequences. In the present study, d-Val and d-gamma-hydroxyvaline (d-Hyv; V) have been found within ribosomally expressed polypeptide chains. Four conopeptides were initially isolated, gld-V/gld-V'from the venom of Conus gladiator and mus-V/mus-V' from the venom of Conus mus. Their complete sequences (gld-V/gld-V' = Ala-Hyp-Ala-Asn-Ser-d-Hyv-Trp-Ser and mus-V/mus-V' = Ser-Hyp-Ala-Asn-Ser-d-Hyv-Trp-Ser) were determined by a combination of nano/pico-NMR and MS/MS methods. The amino acid triad that contains the gamma-hydroxylated residue, Ser-d-Hyv-Trp, is a novel structural motif that is stabilized by specific interactions between the d-amino acid and its neighboring l-counterparts. These interactions inhibit lactonization, a peptide backbone scission process that would normally be initiated by gamma-hydroxylated residues. Conopeptides possessing the Ser-d-Hyv-Trp motif have been termed gamma-hydroxyconophans. We have also isolated analogous conopeptides (gld-V and mus-V) containing d-Val instead of d-Hyv; these are termed conophans. gamma-Hydroxyconophans and conophans are particularly atypical because (i) they are not constrained as most conopeptides, (ii) they are extremely short in length, (iii) they have a high content of hydroxylated residues, and (iv) their sequences have no close match with other peptides in sequence databases. Their modifications appear to be part of a novel hyperhydroxylation mechanism found within the venom of cone snails that enhances neuronal targeting. The finding of d-Val and d-Hyv within this family of peptides suggests the existence of a corresponding d-stereospecific enzyme capable of d-Val oxidation.

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Hyperhydroxylation: A New Strategy for Neuronal Targeting by Venomous Marine Molluscs

Franco¹,

Pisarewicz²,

Möller³

et al. 2006

Progress in Molecular and Subcellular Biology

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Search for new compounds and biologically active substances from Chinese marine organisms

Abstract: Abstract

Cited by 11 publications

References 0 publications

Two New Cytotoxic Tetracyclic Tetraterpenoids from the Soft Coral Sarcophyton tortuosum

Two New Cytotoxic Tetracyclic Tetraterpenoids from the Soft Coral Sarcophyton tortuosum

Polypeptide Chains Containingd-γ-Hydroxyvaline

Hyperhydroxylation: A New Strategy for Neuronal Targeting by Venomous Marine Molluscs

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