Durumolides A–E, anti-inflammatory and antibacterial cembranolides from the soft coral Lobophytum durum

Cheng, Shi‐Yie; Wen, Zhi‐Hong; Chiou, Shu‐Fen; Hsu, Chi‐Hsin; Wang, Shang‐Kwei; Dai, Chang‐Feng; Chiang, Michael Y.; Duh, Chang‐Yih

doi:10.1016/j.tet.2008.07.104

Cited by 68 publications

(58 citation statements)

References 26 publications

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“…Similarly, from the same university, Cheng et al found that new cembranolides from the soft coral Lobophytum durum, durumolides A-C (5, 6, 7) inhibited both the iNOS and COX-2 proteins in LPS-activated RAW 264.7 cells in vitro (apparently IC 50 was less than 10 μmol/L) suggesting that the α-methylene-γ-lactone moiety of these compounds was necessary for the observed activity [19]. Cheng et al also isolated durumhemiketalolides A-C (8, 9, 10) and durumolide F (11) from the soft coral Lobophytum durum with anti-inflammatory activity [20,21].…”

Section: Diterpenoidmentioning

confidence: 92%

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Marine soft corals as source of lead compounds for anti-inflammatories

Putra¹,

Murniasih²

2016

J Coast Life Med

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Section: Diterpenoidmentioning

confidence: 92%

“…Compounds 23 and 24 reduced iNOS protein expression (47.3% ± 7.1%, 46.5% ± 5.3%, respectively), but did not inhibit COX-2 protein expression (Figure 4) [28]. Gyrosanolide B (18) Gyrosanolide C (19) Simplexin E (15) …”

Section: Glycolipidmentioning

confidence: 99%

Marine soft corals as source of lead compounds for anti-inflammatories

Putra¹,

Murniasih²

2016

J Coast Life Med

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“…Meanwhile, the genus Lobophytum yielded twelve analogs, durumolides A-L (222-233). Anti-inflammatory activity of metabolites 227 and 232 (10 μM) significantly reduced the levels of the iNOS protein to 0.8 ± 0.6% and 5.7 ± 2.2%, respectively, and COX-2 protein to 47.8 ± 9.0% and 71.6 ± 5.8%, respectively [76,77]. The soft coral Lobophytum crassum continues to provide novel cembranoids withlactone, including crassumolides A-D, F (234-238) [55], 2-hydroperoxysarcophine (239) [78], lobocrassolide (240) [79], and two unnamed diterpenes (241, 242) [23].…”

Section: -Membered Lactonementioning

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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“…The in vitro anti-inflammatory assay was carried out according to the procedure described previously. [22][23][24] For statistical analysis, all the data were analyzed by a one-way analysis of variance (ANOVA), followed by the Student-Newman-Keuls post hoc test for multiple comparisons. A significant difference was defined as a p value of Ͻ0.05.…”

Section: )mentioning

confidence: 99%

Ylangene-Type and Nardosinane-Type Sesquiterpenoids from the Soft Corals Lemnalia flava and Paralemnalia thyrsoides

Cheng

Lin

Huang

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Chemical investigations of the Formosan soft coral Lemnalia flava have obtained a new ylangene-type sesquiterpenoid, (1S,2S,4R,6S,7R,8S)-4a a-formyloxy-b b-ylangene (1), along with two known sesquiterpenoids, lemnalol (2) and isolemnalol (3). Three new nardosinane-type sesquiterpenoids, designated as paralemnolins J-L (4-6), and five known sesquiterpenoids (7-11), were isolated from the other soft coral Paralemnalia thyrsoides. The structures of metabolites 1 and 4-6 were elucidated through extensive spectroscopic analysis and chemical methods. Moreover, the anti-inflammatory activity of metabolites 1-7 and 11 was evaluated in vitro.Key words Lemnalia flava; ylangene-type sesquiterpenoid; nardosinane-type sesquiterpenoid; Paralemnalia thyrsoides; antiinflammatory activity Chem. Pharm. Bull. 58(3) 381-385 (2010) © 2010 Pharmaceutical Society of Japan * To whom correspondence should be addressed. e-mail: yihduh@mail.nsysu.edu.tw . Moreover, the 1 H-1 H correlation spectroscopy (COSY) correlations (Fig. 2) between H-4 and H-16, and the heteronuclear multiple bond correlation (HMBC) correlations from H-16 to C-4 confirmed the location of the formyloxy functionality at C-4. Therefore, the planar structure of 1 was proposed decidedly.The computer modeled 3D structure of 1 was generated by using MM2 force field calculations for energy minimization with the molecular modeling program Chem3D Ultra 9.0. The relative stereochemistry of 1 assigned by the nuclear Overhauser effect spectroscopy (NOESY) spectrum was compatible with those of 1 offered by computer modeling, in which the close contacts of atoms calculated in space were consistent with the NOESY correlations (Fig. 3). A large long-range coupling constant ( 4 J 2,6 ϭ5.9 Hz) due to a W-type coupling between H-2 and H-6 further indicated the presence of a bridged cyclobutane system in 1. In addition, no coupling was observed between H-7 and the adjacent protons (H-2, H-6, and H-8), suggesting a dihedral angle of approximately 90°between these protons. The NOESY correlations between H 3 -11 with both H-4 and H-5b positioned the b-orientation of the aforementioned protons. Furthermore, H-7 382Vol. 58, No. 3

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Durumolides A–E, anti-inflammatory and antibacterial cembranolides from the soft coral Lobophytum durum

Cited by 68 publications

References 26 publications

Marine soft corals as source of lead compounds for anti-inflammatories

Marine soft corals as source of lead compounds for anti-inflammatories

Cembrane Diterpenes Chemistry and Biological Properties

Ylangene-Type and Nardosinane-Type Sesquiterpenoids from the Soft Corals Lemnalia flava and Paralemnalia thyrsoides

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