Marine terpenes and terpenoids. VI. Isolation of several plausible precursors of marine cembranolides, from the soft coral, Sinularia mayi.

Kobayashi, Masaru; Hamaguchi, Takuya

doi:10.1248/cpb.36.3780

Cited by 22 publications

(14 citation statements)

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“…The new compounds were named as lobophyolide A ( 1 ) and B ( 2 ) and the known compounds were identified as 16-methoxycarbonyl-cembrene A ( 3 ) [50], sinarone ( 4 ) [83], sinulariol D ( 5 ) [83], 16-acetyl-sinulariol D ( 6 ) [83], and ( E , E , E )-6,10,14-trimethy-3-methylene-trans-3 α ,4,7,8,11,12,15,15 α -octahydrocy clotetradeca[ β ]furan-2(3H)-one ( 7 ) [3]. …”

Section: Resultsmentioning

confidence: 99%

Anti-Inflammatory Cembranoids from the Soft Coral Lobophytum crassum

et al. 2017

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Cembrane-type diterpenoids are among the most frequently encountered natural products from the soft corals of the genus Lobophytum. In the course of our investigation to identify anti-inflammatory constituents from a wild-type soft coral Lobophytum crassum, two new cembranoids, lobophyolide A (1) and B (2), along with five known compounds (3–7), were isolated. The structures of these natural products were identified using NMR and MS spectroscopic analyses. Compound 1 was found to possess the first identified α-epoxylactone group among all cembrane-type diterpenoids. The in vitro anti-inflammatory effect of compounds 1–5 was evaluated. The results showed that compounds 1–5 not only reduced IL-12 release, but also attenuated NO production in LPS-activated dendritic cells. Our data indicated that the isolated series of cembrane-type diterpenoids demonstrated interesting structural features and anti-inflammatory activity which could be further developed into therapeutic entities.

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Section: Resultsmentioning

confidence: 99%

Anti-Inflammatory Cembranoids from the Soft Coral Lobophytum crassum

et al. 2017

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“…24) Part of the n-hexane extract (21.1 g) was dissolved in n-hexane and was further partitioned against 90% of aqueous methanol to yield a nhexane soluble part (7.2 g). Flash chromatography of this part (7. 8 mg), 26) 17 (1.0 mg), and 18 (0.7 mg). 27) Fr.…”

Section: Methodsmentioning

confidence: 99%

Four New Cembrane Diterpenes Isolated from an Okinawan Soft Coral Lobophytum crassum with Inhibitory Effects on Nitric Oxide Production

Wanzola

Furuta

Kohno

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Regular ArticleSoft corals are well known to be a rich source of terpene metabolites, especially diterpenes of the cembranoid series, 1,2) which are naturally occurring diterpenens containing a 14-carbon ring. Many of them are of great interest as they exhibit a wide range of biological activities including ichthyotoxic, anti-cancer, anti-inflammatory, anti-human immunodeficiency virus (HIV), and anti-microbial activities. [3][4][5][6][7][8][9] In the continuation of our ongoing research for bioactive marine natural products, we have investigated the n-hexane extract of the Lobophytum crassum (von Marenzeller, 1886) which has exhibited a significantly inhibitory effect on nitric oxide (NO) production against lipopolysaccharide (LPS)-induced Raw 264.7. Chemical investigation revealed that the nhexane-soluble material in this soft coral included four new (1-4) and fifteen known (5-19) cembranoids (Fig. 1). In this paper, we report on the isolation and structure elucidation of four new cembranoids 1-4 and also the determination of absolute stereochemistry of the new 1 and 2 and the known cembranoids 5 and 6. Furthermore, the inhibitory effect of some isolates was evaluated on NO production against Raw264.7.The frozen L. crassum collected in Okinawa was completely extracted in n-hexane. The extract was partitioned between n-hexane and aqueous methanol. The n-hexane soluble-material was subjected to silica gel flash column chromatography and recycling HPLC, followed by the reversed phase (RP) HPLC to afford four new cembranoids 1-4 and fifteen known cembranoids 5-19.The molecular formula of 1 was determined to be C-NMR spectra of 1 showed signals assignable to three olefinic methyls, one acetylmethyl, three trisubstituted double bonds, one exomethylene, two oxymethines, one aliphatic methine, five methylenes, and two ester carbonyls. Six of the eight degrees of unsaturation in 1 were attributed to four double bonds and two ester carbonyls (Tables 1, 2). The remaining two degrees of unsaturation were attributed to the bicyclic ring system of 1. Interpretation of correlation spectroscopy (COSY) and total correlation spectroscopy (TOCSY) spectra, in combination with heteronuclear multiple bond correlation (HMBC) experiments, led to the planar structure of 1 (Fig. 2) easily merged these three spin systems and the presence of an a-methylene-l-lactone adjacent to the 14-membered ring. Thus, the planar structure of 1 was depicted in Fig. 2. The E-geometry of the D 3 and D 7 was determined by the nuclear Overhauser effect (NOE) correlations between H-3/H-5 and H-7/H-9 (d H 2.00), and the Zgeometry of the D 12 was determined by the strong NOE between H-13 and H-20. The cis-fused a-methylene-l-lactone and the 14-membered ring was deduced from the NOE correlation between H-1 and H-2. In addition, NOE correlations were observed between H-3 and H-2/H-5/H-7, H-7 and H-9/H11, H-13 and H-1/H-17/H-20. These data revealed the conformation of the 14-membered ring and the relative configuration of C-11. Thus, the relative stereochemist...

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“…[24], Lobopytum sp. (53)(54)(55) [25], Sinularia ovispiculata (56) [26], Cladiella kashmani (57) [27], Alcyonium flaccidum (56) [28]. Five new cembradiene diterpenoids (58)(59)(60)(61)(62)(63) have been isolated from an undescribed Caribbean gorgonian of the genus Eunicea [29].…”

Section: Isopropyl Cembranesmentioning

confidence: 99%

“…Sinulaflexiolide E showed selective inhibitory activity against the gastric gland carcinoma cell line BGC-823 at 0.12 μM [43]. Meanwhile, the genus Sinularia yielded a cluster of cembranoids, including sinularic acid A (196) [54], granosolides C (197) and D (198) [71], querciformolide E (199) [71]. A series of analogs were isolated from Sarcophyton glaucum (200) [72], Lobophytum crassum (201) [23], Eunicea succinea (202) [61], Eunicea mammosa (203) [62].…”

Section: Isopropyl/ Isopropenyl Acid Cembranesmentioning

confidence: 99%

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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Marine terpenes and terpenoids. VI. Isolation of several plausible precursors of marine cembranolides, from the soft coral, Sinularia mayi.

Cited by 22 publications

References 1 publication

Anti-Inflammatory Cembranoids from the Soft Coral Lobophytum crassum

Anti-Inflammatory Cembranoids from the Soft Coral Lobophytum crassum

Four New Cembrane Diterpenes Isolated from an Okinawan Soft Coral Lobophytum crassum with Inhibitory Effects on Nitric Oxide Production

Cembrane Diterpenes Chemistry and Biological Properties

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