Structural determination of carnosadine, a new cyclopropyl amino acid, from red alga Grateloupia carnosa

Wakamiya, Tateaki; Nakamoto, Hidetaka; Shiba, Tetsuo

doi:10.1016/s0040-4039(01)81452-0

Cited by 38 publications

(16 citation statements)

References 4 publications

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“…The major difference between these and other dolabellane derivatives is that the sites of unsaturation in the eleven-membered ring are at positions 4 and 8 rather than at 3 and 7 or at 2 and 7. Metabolite (90) is the only one that exhibits significant cytotoxicity.h8 Although no new dolastane diterpenes have been described during the reporting period, the absolute stereochemistry of isoamijiol (98) was determined by the c.d. allylic benzoate method."…”

Section: Brown Algaementioning

confidence: 99%

Marine natural products

Faulkner¹

1986

Nat. Prod. Rep.

477

214

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Section: Brown Algaementioning

confidence: 99%

Marine natural products

Faulkner¹

1986

Nat. Prod. Rep.

477

214

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“…The synthesis of the drugs followed a drug designed study finalized to project structures capable of selectively inhibiting the neuronal NOS [8][9][10][11][12].…”

Section: Methodsmentioning

confidence: 99%

Selective Inhibition of Neuronal Nitric Oxide Synthase by L-Arginine Derivatives

Capasso¹,

Saturnino²,

Buonerba

2008

LDDD

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Niric Oxide (NO) is a free radical which plays an important role in cellular signalling in mammals. NO is involved in the regulation of vascular tone, modulation of platelet adhesion, whereas in the central nervous system NO isgenerated following the activation of the ionotropic and the metabotropic receptors of the excitatory aminoacid. Larginine has been shown to be obligatory for the formation of the NO. Substances capable of antagonising the effect of NO could be suitable in the therapy of some forms in which there is an excessive vasodilator response or over-activation of the central excitatory circuits. A series of new arginine derivatives named MCS1, MCS2, MCS3, MCS4, MCS5, MCS6, MCS7 have been synthetized and their action on the NO synthase (NOS) has been tested. The NOS activity has been tested in homogenates of both human umbilical endothelial cells (HUVEC) and rat brain, by evaluating the conversion of 14 C-L-arginine in 14 C-L-citrulline in the presence and absence of scalar concentration of MCS compounds (10 μM-100 μM). In both HUVEC and rat brain, the 14 C-L-citrulline formation was completely inhibited by MCS3, MCS4, MCS5, MCS6 and MCS7 at the 100 μM concentration; MCS1 and MCS2 inhibited the NOS activity in the rat brain, but failed to inhibit NOS activity in HUVEC, MCS3, MCS4, MCS5, MCS6 were equiactive on the neuronal NOS and endotelial NOS whereas MCS7 was more active in inhibiting both.The results of the present study suggest that some arginine derivative compounds are able to block the NOS. Some of these compounds are able to inhibit the NOS production at both endothelial and neuronal level, whereas others are active only on one substrate. In particular, MCS1, MCS2 and MCS7 are relatively selective for neuronal NOS whereas MCS7 is also active on endothelial NOS.

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“…81,82 Carnosadine (40), which is an arginine analogue, has been isolated from the red alga Grateloupia carmasa. 83,84 Although the number of the known methanologues of natural amino acids is presently quite large, there have been only a few detailed structural and conformational studies of peptides that include these acids. The most studied peptides are those containing methanologues of methionine, 85 ± 87 phenylalanine 88,89 and diphenyl-substituted ACC.…”

Section: -Aminocyclopropanecarboxylic Acid and Its Derivativesmentioning

confidence: 99%