Bioactive Terpenoids from Octocorallia. 4. Three New Cembrane-Type Diterpenoids from the Soft Coral <i>Lobophytum schoedei</i>

Yamada, Koji; Ryu, Kenjiro; Miyamoto, Tomofumi; Higuchi, Ryota

doi:10.1021/np960728m

Cited by 38 publications

(37 citation statements)

References 15 publications

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“…Earlier studies of the genus Lobophytum led to the isolation of several sesquiterpenoids, cembrane and lobane diterpenes, sterols and sphingolipids. 7,8) Several compounds from this genus showed cytotoxic, [9][10][11] anti-HIV, 12) antibacterial, 13) and ichthyotoxic [14][15][16][17] activities. In this paper we report the isolation and structural elucidation of three new sphingolipids and a sterol along with cytotoxic activity of a known sphingolipid isolated from the organism.…”

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confidence: 99%

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New Sphingolipids and a Sterol from a Lobophytum Species of the Indian Ocean

Muralidhar¹,

Kumar²,

Krishna³

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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As part of our continuous search for bioactive metabolites from marine organisms, [2][3][4][5][6] we have investigated a soft coral species belonging to the genus Lobophytum collected from the Indian Ocean. Earlier studies of the genus Lobophytum led to the isolation of several sesquiterpenoids, cembrane and lobane diterpenes, sterols and sphingolipids. 7,8) Several compounds from this genus showed cytotoxic, [9][10][11] anti-HIV, 12) antibacterial, 13) and ichthyotoxic [14][15][16][17] activities. In this paper we report the isolation and structural elucidation of three new sphingolipids and a sterol along with cytotoxic activity of a known sphingolipid isolated from the organism.Sphingolipids exist widely in the eukaryotic cell membranes of both terrestrial and marine organisms.18) Sphingolipids attracted much attention in recent years due to their involvement in various cellular processes including cell growth, survival, differentiation, and adhesion. 19,20) Results and DiscussionRepeated column chromatography of EtOAc solubles of the methanolic extract of the organism followed by purification by medium pressure liquid chromatography (MPLC) afforded compounds 1-5 as colourless solids. The IR spectra of 1-3 suggested the presence of hydroxyl and amide groups while the UV spectra had no characteristic signals above 210 nm. Close examination of 1 H-and 13 C-NMR spectra of 1-3 (Table 1) revealed the presence of NH, carbonyl, end methyls and long aliphatic chain suggesting sphingolipid skeleton. . The stereochemistries at C-2, C-3 and C-2Ј were assigned 2S, 3R and 2ЈR by comparing the NMR and optical rotation data with those of natural and synthetic sphingolipids. [24][25][26][27] The geometry of the double bonds was taken as trans (4E,8E) on the basis of large coupling constants (15.3, 15.0 Hz). Chemical investigation of a soft coral species of the genus Lobophytum has resulted in the isolation of three new sphingolipids- (2S,3S,4R)-2-nonadecanoylamino-octadecane-1,3,4-triol (1), (2S,3R,4E,8E)

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confidence: 99%

“…antibacterial, 13) and ichthyotoxic [14][15][16][17] activities. In this paper we report the isolation and structural elucidation of three new sphingolipids and a sterol along with cytotoxic activity of a known sphingolipid isolated from the organism.…”

mentioning

confidence: 99%

New Sphingolipids and a Sterol from a Lobophytum Species of the Indian Ocean

Muralidhar¹,

Kumar²,

Krishna³

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Moreover, sarcophytol T (23), was isolated from the same species by Konig and his coworker [14]. From the soft coral Sarcophyton sp., studies have led to the identification of two new cembranes, epoxysartone B (24), and sartone E (25) [15]. Naturally occurring cembranes (26)(27)(28)(29) have been isolated from Sarcophyton sp.…”

Section: Isopropyl Cembranesmentioning

confidence: 99%

“…[22]. [24], Lobopytum sp. (53)(54)(55) [25], Sinularia ovispiculata (56) [26], Cladiella kashmani (57) [27], Alcyonium flaccidum (56) [28].…”

Section: Isopropyl Cembranesunclassified

“…Lobophynin C displayed ichthyotoxicity with an LC 100 value of 30 ppm and exhibited toxicity with an LC 50 value of 22.5 ppm in the brine shrimp lethality bioassay [24]. Furthermore, other similar diterpenes were discovered in the soft corals, including sarcophytonin E (540) [161], 13-dehydroxysarcoglaucol (541) [89], (+)-12-carboxy-11Z-sarcophytoxide (542), lobophynin C (543) [13], (-)-7 -hydroxy-8 -methoxydeepoxysarcophytoxide (544), (-)-7 ,8 -dihydroxydeepoxysarcophytoxide (545), and (-)-17-hydroxysarcophytonin A (546) [49], 11,12-epoxy-sarcophytoxide (547) [160].…”

Section: Furanocembranoidsmentioning

confidence: 99%

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Cembrane Diterpenes Chemistry and Biological Properties

Yang¹,

Zhou²,

Lin³

et al. 2012

COC

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Cembrane-type diterpenoids are a large and structurally varied group of natural products isolated from both terrestrial and marine organisms. The present paper reviews all the metabolites of cembrane diterpenes, reported up to 2010. The natural products discussed in this review can be divided into several different structural families featuring a variety of ring sizes and oxidation patterns. The currently known biological activities will be presented as well.

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Cnidaria and Ctenophora–2

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Membrane Constituents and Secondary Metabolites of Hexacorallia (Anthozoa) Fatty Acids, Oxylipins, and Acetylenic Derivatives Sterols and Ecdysteroids Terpenes Carotenoids of Sea Anemones Aromatic Derivatives Ceramides and Lipidic α‐Amino Acids Examples of Nitrogenous Pigments: Zoanthoxanthins and Calliactine Palytoxins ( PTXs ) Mycosporines Betaines, Phosphobetaines, Purines, and Other Nitrogen‐Containing Derivatives Zoanthamine Alkaloids Cytolysins, Neuropeptides, and Other Venoms of Sea Anemones Venoms and Other Metabolites of Medusozoa Some Data on the Cubozoa and Other Jellyfish Bioluminescence of Jellyfish and Other Cnidaria Some Results on the Secondary Metabolites of Other Hydrozoa Ctenophora

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Bioactive Terpenoids from Octocorallia. 4. Three New Cembrane-Type Diterpenoids from the Soft Coral Lobophytum schoedei

Cited by 38 publications

References 15 publications

New Sphingolipids and a Sterol from a Lobophytum Species of the Indian Ocean

New Sphingolipids and a Sterol from a Lobophytum Species of the Indian Ocean

Cembrane Diterpenes Chemistry and Biological Properties

Cnidaria and Ctenophora–2

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