A new cerebroside from Fusicoccum amygdali Del

Ballio, A.; Casinovi, C. G.; Framondino, M.; Marino, Gennaro; Nota, G.; Santurbano, B.

doi:10.1016/0005-2760(79)90172-3

Cited by 47 publications

(25 citation statements)

References 23 publications

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“…Cerebrosides and sphingosine derivatives have been isolated from diverse natural sources, including plants, 7) marine sources, 8) microorganisms, 9) and human. 10) Phytosphingosine type cerebrosides are reported to exhibit bioactivities such as the antitumor, 11) antiviral, 12) inhibition of histidine decarboxylase, 13) cytotoxicity, 14) and antifungal activity.…”

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“…10) Phytosphingosine type cerebrosides are reported to exhibit bioactivities such as the antitumor, 11) antiviral, 12) inhibition of histidine decarboxylase, 13) cytotoxicity, 14) and antifungal activity. 14) In a continuing study on the same sponge, fourteen phytosphingosine type cerebrosides (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were isolated from the n-hexane layer. Nine (1-9) of them contained saturated acyl chains, while five (10)(11)(12)(13)(14) possessed unsaturated acyl chains.…”

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“…Separation of the n-hexane layer by medium pressure liquid chromatography (MPLC) on a normal-phase flash column yielded 20 fractions. Fraction 16 was found to contain sugar moieties as observed in 1 H-NMR spectra, and was subjected to repeated HPLC chromatographic separation using ODS column to yield nine cerebrosides (1)(2)(3)(4)(5)(6)(7)(8)(9). And the mixture of fractions 10 to 15 afforded five analogues (10)(11)(12)(13)(14) through HPLC separation using the same condition as for fraction 16.…”

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New Cerebrosides from a Marine Sponge Haliclona (Reniera) sp.

Park

Mansoor

Shinde

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Sponges of the genus Haliclona have been extensively studied and afforded around 200 compounds belonging to different chemical classes. These compounds include the cytotoxic tertiary alkaloids haliclonacyclamines, 1) antifungal pentacyclic alkaloid papuamine, 2) antitumor alkaloid manzamine, 3) and anti-inflammatory cyclic depsipeptides halipeptins, 4) to name a few.In our previous study on the marine sponge Haliclona (Reniera) sp., we reported the isolation and structure elucidation of eight new cerebrosides 5) and a new sphingosine 6) obtained from the MeOH extract. Cerebrosides and sphingosine derivatives have been isolated from diverse natural sources, including plants, 7) marine sources, 8) microorganisms, 9) and human. 10) Phytosphingosine type cerebrosides are reported to exhibit bioactivities such as the antitumor, 11) antiviral, 12) inhibition of histidine decarboxylase, 13) cytotoxicity, 14) and antifungal activity. 14) In a continuing study on the same sponge, fourteen phytosphingosine type cerebrosides (1-14) were isolated from the n-hexane layer. Nine (1-9) of them contained saturated acyl chains, while five (10-14) possessed unsaturated acyl chains. Their structures were established on the basis of NMR and MS analyses, and chemical methods. Some of the cerebrosides (1, 3, 5, 7, 11, 12) contained unusual acyl chains with S-configuration. It is interesting to isolate epimeric pairs (1 : 2, 3 : 4, 5 : 6, 7 : 8) from the same specimen. Herein, we report isolation and structural characterization of cerebrosides from a marine sponge Haliclona (Reniera) sp.The brine shrimp-active MeOH extract (LD 50 126 mg/ml) of the sponge was partitioned between CH 2 Cl 2 and H 2 O. The CH 2 Cl 2 layer was further partitioned between aqueous MeOH (LD 50 27 mg/ml) and n-hexane (LD 50 45 mg/ml). Separation of the n-hexane layer by medium pressure liquid chromatography (MPLC) on a normal-phase flash column yielded 20 fractions. Fraction 16 was found to contain sugar moieties as observed in 1 H-NMR spectra, and was subjected to repeated HPLC chromatographic separation using ODS column to yield nine cerebrosides (1-9). And the mixture of fractions 10 to 15 afforded five analogues (10-14) through HPLC separation using the same condition as for fraction 16. Their structures were defined using NMR ( 1 H, 13 C, correlation spectroscopy (COSY), heteronuclear single quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC), and total correlation spectroscopy (TOCSY)) and MS analysis, optical rotation data, and chemical method.Renieroside C 1 (1) was obtained as a white, amorphous solid. Its molecular formula was assigned as C 39 1-3, 5-14), along with a known analogue (4). Their structures were elucidated on the basis of 1D and 2D NMR spectroscopy, MS spectrometry, and chemical method. The major new features of these glucocerebrosides are C 15 and C 19 acyl chains, long (C 24 -C 28 ) acyl chains, or the S-configuration of the acyl chains. It is noteworthy that both R-and S-configurations of the acyl chains wer...

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New Cerebrosides from a Marine Sponge Haliclona (Reniera) sp.

Park

Mansoor

Shinde

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Ballio et al 30 ) reported a cerebroside from a Deuteromycete, Fusicoccum amygdali, having a structure resembling that of Pen II. According to our study, the sample given to us by them exhibited the fruiting-inducing activity.?)…”

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confidence: 99%

Fruiting ofSchizophyllum communeInduced by Certain Ceramides and Cerebrosides fromPenicillium funiculosum

Kawai

Ikeda

Tubaki

1985

Agricultural and Biological Chemistry

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“…Limited investigations in the past in which whole-body preparations were studied have indicated that both gluco-and galactocerebrosides are distributed in small quantities in many protostomes and deuterostomes as well as parazoan animals with diffuse ganglionic nervous systems (16)(17)(18)(19)(20)(21). The present investigation focused on isolated nervous system tissues and demonstrates a distinct dichotomy between the carbohydrate moieties of cerebrosides found in these tissues.…”

Section: Discussionmentioning

confidence: 99%

Phylogenetic dichotomy of nerve glycosphingolipids.

Okamura¹,

Stoskopf²,

Hendricks³

et al. 1985

Proc. Natl. Acad. Sci. U.S.A.

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Galactocerebrosides and sulfatides are major characteristic components of vertebrate myelin. In contrast, glucocerebroside is the major glycosphingolipid of shrimp nerve. In this study, the concentrations of these glycosphingolipids in the nervous systems of animais from several evolutionary branches were determined by use of high-performance liquid chromatography. In nerves of protostome animals only glucose-containing glycosphingolipids were detected, whereas glycosphingolipids from deuterostomes contained predominantly galactose. Neither the glycolipids containing a-hydroxy fatty acids nor sulfate esters of the glycolipids, both of which always accompany galactocerebrosides in deuterostome myelin, were present in protostome nerves. This correlation suggests an evolutionary trend from gluco-to galactocerebrosides, which corresponds with changes in the nervous system from loosely structured membrane-enwrapped axons to multilameliar highly structured myelin.Rapid saltatory conduction of nerve impulses in vertebrates is facilitated by the myelin sheath, a unique multilamellar membrane that tightly enwraps axons (1). Vertebrate myelin is characterized by abundant lipids, with particularly high levels of galactocerebrosidest and sulfatides, which are considered to be myelin markers (2). The nervous systems of invertebrates, on the other hand, lack true compact myelin, although axons in higher orders (e.g., crustacea) are surrounded by layers ofloosely bound membrane (3). Previously we found that the nervous system of the brown shrimp (Penaeus aztecus aztecus) contained high concentrations of glucocerebroside but no galactocerebroside (4). Since little is known about the chemical composition ofthe nervous system of lower animals and because of the possible evolutionary significance of the change from gluco-to galactocerebroside in the development of the nervous system, we began a systematic survey ofthe sphingolipid composition of nervous tissue from a wide variety of animals from several evolutionary branches. We found that, whereas nervous system glycolipids from deuterostomes contained predominantly galactose, those from protostomes contained only glucose.MATERIALS AND METHODS Animals. Animals studied are listed in Table 1 and were of reproductive age unless otherwise specified. These animals were obtained either from colleagues or from marine supply houses, as also indicated in Table 1. Appropriate nerves (Table 1) were dissected under a microscope after the animal had been anesthetized either by immersion in 0.02% ethyl m-aminobenzoate methane sulfonate or by exposure to cold temperature.Glycosphingolipid Analysis. Concentrations of gluco-and galactocerebrosides and sulfatides were measured by HPLC after treating these lipids by benzoylation-desulfation as described (5). The nerves were homogenized in cold water immediately after dissection and total lipids were extracted with chloroform/methanol and washed according to Folch et al. (6). The total lipids obtained were then benzoylated with benzoyl chlo...

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A new cerebroside from Fusicoccum amygdali Del

Cited by 47 publications

References 23 publications

New Cerebrosides from a Marine Sponge Haliclona (Reniera) sp.

New Cerebrosides from a Marine Sponge Haliclona (Reniera) sp.

Fruiting ofSchizophyllum communeInduced by Certain Ceramides and Cerebrosides fromPenicillium funiculosum

Phylogenetic dichotomy of nerve glycosphingolipids.

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