Eudistomidins B, C, and D: novel antileukemic alkaloids from the Okinawan marine tunicate Eudistoma glaucus

Kobayashi, Jun’ichi; Cheng, Jie; Ohta, Tomihisa; Nozoe, Shigeo; Ohizumi, Yasushi; Sasaki, Takuma

doi:10.1021/jo00298a056

Cited by 131 publications

(72 citation statements)

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“…Eudistomin K (57) exhibited potent cytotoxic activities in vitro against murine P-388 cells with IC 50 value of 0.01 g/ml, and the antitumor assay in vivo gave a T/C of 137% at 100mg/kg, and further antitumor activities in vivo against L1210, A549 and HCT-8 cell lines were also reported [158]. Eudistomidins B (45), C (46) and D (47) showed significant cytotoxicities against murine leukemia L1210 (IC 50 respectively [159]. Eudistomin U (60) and its derivatives were synthesized and evaluated by Dong et al [160] for antitumor activities.…”

Section: -Methoxymanzamine Amentioning

confidence: 95%

“…Exhibition cytotoxicities against murine P-388 [158] 2. Exhibition antitumor activities in vivo against L1210, A549 and HCT-8 cell lines [158] Eudistomidins B, C and D Exhibition cytotoxicities against murine leukemia L1210 L5178Y cell lines [159] Eudistomin U and its derivatives Exhibition cytotoxicities against murine P-388 [160] (-)-Debromoeudistomin K and its analogues Exhibition cytotoxicities against murine leukemiaL1210, Molt/4F, MT-4 and leukemia P-388 cells [162] Hyrtioerectines A Exhibition cytotoxicity against HeLa cell lines [163] Plakortamines A, B, C and D Exhibition cytotoxicities against HCT-116 human colon tumor cell line [164] N-methyl -carbolinium derivatives Exhibition cytotoxicities against four human tumor cell lines LOX, OVCAR-3, COLO-205 and MOLT-4 [165] 6-Hydroxymanzamine A, 3,4-dihydromanzamine Exhibition cytotoxicities against L1210 and KB cell lines [166] Manzamine A…”

Section: Antitumor Activities Of -Carbolines In Vitro and In Vivomentioning

confidence: 99%

“…Marine ascidians belonging to the genus Eudistoma (family Polycitoridae) are another rich source of biologically active -carboline derivatives. So far, numerous -carboline alkaloids, including eudistomins A-T [177,178,227,228], eudistomidins A-F [229][230][231], eudistalbins A and B [236], eudistomin U and isoeudistomin U [222], eudistomin V [225] and two new trypargine derivatives [233], have been isolated and characterized from various Eudistoma species.…”

Section: Introductionmentioning

confidence: 99%

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β-Carboline Alkaloids: Biochemical and Pharmacological Functions

Cao

Peng²,

Wang³

et al. 2007

CMC

622

353

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beta-Carboline alkaloids are a large group of natural and synthetic indole alkaloids with different degrees of aromaticity, some of which are widely distributed in nature, including various plants, foodstuffs, marine creatures, insects, mammalians as well as human tissues and body fluids. These compounds are of great interest due to their diverse biological activities. Particularly, these compounds have been shown to intercalate into DNA, to inhibit CDK, Topisomerase, and monoamine oxidase, and to interact with benzodiazepine receptors and 5-hydroxy serotonin receptors. Furthermore, these chemicals also demonstrated a broad spectrum of pharmacological properties including sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic as well as antimicrobial activities. In this review, we summerized the biochemical and pharmacological functions of beta-carboline alkaloids.

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Section: -Methoxymanzamine Amentioning

confidence: 95%

Section: Antitumor Activities Of -Carbolines In Vitro and In Vivomentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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β-Carboline Alkaloids: Biochemical and Pharmacological Functions

Cao

Peng²,

Wang³

et al. 2007

CMC

622

353

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“…798 have been confirmed by synthesis. 800 indicates the structure of the natural product requires revision. 800 indicates the structure of the natural product requires revision.…”

Section: View Onlinementioning

confidence: 99%

Marine natural products

et al. 2011

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“…Tunicates and Ascidians (class Ascidiacea) are now well-known to be rich sources of unique and biologically active metabolites including lipids and lipophilic compounds [5,6], in particular those from the Eudistoma genus (family Polycitoridae) [7,8], and those from the apparently less documented genus Leptoclinides (family Didemnidae) [9,10]. New amino acid derivatives have been isolated from a polar cytotoxic extract (P-388 cells) of the ascidian Leptoclinides dubius [11].…”

Section: Introductionmentioning

confidence: 99%

Phospholipid Distribution and Phospholipid Fatty Acids of the Tropical Tunicates Eudistoma sp. and Leptoclinides uniorbis

Dagorn

Dumay

Wielgosz‐Collin

et al. 2010

Lipids

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Two tunicates, Eudistoma sp. and Leptoclinides uniorbis, collected from the tropical waters off Djibouti were investigated for lipids and phospholipid (PL) fatty acids. PL accounted for 38.2% of the total lipids in Eudistoma sp. and for 30.2% in L. uniorbis. PL classes were quantified by normal-phase high-performance liquid chromatography using an evaporative light-scattering detector and revealed essential differences. Eudistoma sp. contained mainly phosphatidylcholine (PC, 70.3% of total PL) and lysophosphatidylcholine (LPC, 11.9%) and was devoid of phosphatidylserine (PS), whereas the major PL of L. uniorbis was PS (59.1%) followed by PC (22.5%) and LPC (8.8%). Gas chromatography-mass spectrometry analyses of fatty acid (FA) derivatives revealed 38 FA in Eudistoma sp., and 35 FA in L. uniorbis, ranged from C(12) to C(24) chain lengths. Polyunsaturated FA accounted for 25.9% in Eudistoma sp. and for 32.3% in L. uniorbis. Interestingly, L. uniorbis contained a high percentage (16.7%) of the 20:5n-3 acid (8.9% in Eudistoma sp.) and the 18:4n-3 acid (4.1%). Significant levels of the 20:4n-6 acid were observed in both organisms (7.8 and 6.0% respectively). Eudistoma sp. contained the rare 20:3n-7 acid (2.3%) only recorded to date in hydrothermal vent animals. The cyclopropane dihydrosterculic acid was identified in both tunicates (0.7 and 0.5% respectively). These latter FA, together with some unusual branched saturated and monounsaturated FA, revealed the occurrence of associated bacteria in the tunicates. Another noticeable feature was a series of eight C(16) to C(18) aldehyde dimethylacetals revealing the presence of plasmalogens at 5.0% in Eudistoma sp. and 14.2% in L. uniorbis. The results of this study were compared with those previously published for other tunicates regarding mainly PL content and FA composition.

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Eudistomidins B, C, and D: novel antileukemic alkaloids from the Okinawan marine tunicate Eudistoma glaucus

Cited by 131 publications

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β-Carboline Alkaloids: Biochemical and Pharmacological Functions

β-Carboline Alkaloids: Biochemical and Pharmacological Functions

Marine natural products

Phospholipid Distribution and Phospholipid Fatty Acids of the Tropical Tunicates Eudistoma sp. and Leptoclinides uniorbis

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Eudistomidins B, C, and D: novel antileukemic alkaloids from the Okinawan marine tunicate Eudistoma glaucus

Cited by 131 publications

References 0 publications

&#946;-Carboline Alkaloids: Biochemical and Pharmacological Functions

&#946;-Carboline Alkaloids: Biochemical and Pharmacological Functions

Marine natural products

Phospholipid Distribution and Phospholipid Fatty Acids of the Tropical Tunicates Eudistoma sp. and Leptoclinides uniorbis

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Product

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β-Carboline Alkaloids: Biochemical and Pharmacological Functions

β-Carboline Alkaloids: Biochemical and Pharmacological Functions