New β-Caryophyllene-Derived Terpenoids from the Soft Coral Sinularia nanolobata

Ahmed, Atallah F.; Su, Jui‐Hsin; Shiue, Ru-Ting; Pan, Xin-Jie; Dai, Chang‐Feng; Kuo, Yao‐Haur

doi:10.1021/np030286w

Cited by 74 publications

(61 citation statements)

References 18 publications

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Glycolipids from the Formosan Soft Coral Lobophytum crassum

Chao

Huang

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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During the course of our investigation on the bioactive chemical constituents from marine invertebrates, [1][2][3][4][5][6] we have investigated a soft coral Lobophytum crassum collected from Taiwanese waters. Earlier studies of the genus Lobophytum have led to the isolation of terpenoids, of which some have shown cytotoxic, [7][8][9][10] anti-HIV, 11) and antibacterial 12) activities. In this paper we report the isolation and structural elucidation of three new glycolipids 1-3 (Fig. 1) from this organism. The absolute configurations of 1-3 were determined by the comparison of specific optical rotations of sugar and aglycon moieties with known compounds, chemical conversions, and the application of Mosher's method. Cytotoxicity of metabolites 1-3 against the growth of a limited panel of cancer cells of HepG2, Hep3B (human liver carcinoma), MDA-MB-231 (human breast carcinoma), and Ca9-22 (human gingival carcinoma) is also discussed. Results and Discussion(2R)-1-Hydroxy-3-hexadecyloxy-propyl-b -D-arabinopyranoside (1) was isolated as amorphous white solid. Its HR-ESI-MS exhibited a pseudomolecular ion peak at m/z 471.3296 [MϩNa] ϩ (Calcd for C 24 H 48 O 7 Na, 471.3298), corresponding to the molecular formula C 24 H 48 O 7 , indicating one degree of unsaturation. The 1 : 2 ratio of carbon and proton atoms and high oxygen content in its molecular formula and strong absorption bands at n max 3391, 1142, 1075, and 1007 cm Ϫ1 in IR spectrum suggested that 1 might be a glycolipid. An anomeric glycoside proton resonance was observed at d 5.67 (1H, d, Jϭ3.3 Hz), corresponding to a carbon resonance at d 100.4 (d) in the HMQC spectrum. Except for the above carbon (C-1Ј), the 13 C-NMR spectrum of 1 exhibited eight oxygenated carbons, including four oxymethylenes at d C 71.7 (t), 71.1 (t), 64.5 (t), and 63.0 (t), and four oxymethines at d C 78.5 (d), 71.0 (d), 70.8 (d), and 70.1 (d) ( Table 1). Above data together with the methyl group resonanting at d H 0.85 (3H, t, Jϭ6.6 Hz) and methylenes at d H 1.26 (br s) revealed the structure of 1 to be a glycoside with a long aliphatic chain.The gross structure of metabolite 1 was further established by the 2D-NMR studies, particularly in 1 H-1 H COSY, HMQC and HMBC experiments. The correlations of 1 H-1 H COSY revealed proton-proton sequences, from H-1Ј to H-5Ј, H 2 -1 to H 2 -3, H 2 -1Љ to H 2 -2Љ, and H 2 -15Љ to H 3 -16Љ, as shown in Fig. 2. The HMBC correlations from H-1Ј to C-5Ј and C-2, as well as other correlations illustrated in Fig. 2, established a pyranose and a glycerol ether moiety. The pyranose was identified as b-arabinopyranose by analysis of coupling constants of the related protons (Table 1). HR-ESI mass spectrum and the above 2D-NMR spectroscopic analysis led to the establishment of the aglycon to be chimyl alcohol.The absolute configurations on the sugar portion and lipid aglycon were determined on the basis of methanolysis, chemical transformation and the application of the modified Mosher's method. As shown in Chart 1, methanolysis of 1 with 1 N HCl (aq) -MeOH...

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Glycolipids from the Formosan Soft Coral Lobophytum crassum

Chao

Huang

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Ahmed et al (2003) berhasil mengisolasi senyawa β-caryophyllene turunan terpenoid dari S. nanolobata. Ahmed et al (2004) (Arepalli, 2007). Karang lunak genus Sinularia dapat dijadikan salah satu sumber potensial dalam penemuan senyawa antimitotik yang baru.…”

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Aktivitas Antimitotik Dari Ekstrak Karang Lunak Genus Sinularia

Tanod¹,

Mangindaan

Kapojos

2015

omni.akua

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Soft coral genus Sinularia be a sources of terpenoid compounds that show efficacy in vitro cytotoxic test using cancer cell lines. The study looked at the morphological changes that occur in fungal mycelial growth of Pyricularia oryzae, such as curling effect indicating antimitotic activity. Four extracts of soft coral genus Sinularia have been examination and this is an primary test to obtain information about the soft coral genus Sinularia that used as sources of compound antimitotic. This research was conducted in several stages, ie extraction of bioactive substances, P. oryzae fungal culture test, and biological testing antimitotic activity with a qualitative assessment methods. From the examination the Sinularia 3 ethyl acetate fraction show the strongest antimitotic activity (to concentration 1,5 µg/ml). Ethyl acetate fraction was purified using column chromatography. From the examination show that fraction of ethyl acetate 1 is the best fraction because still show curling effect on concentration 0,7 µg/ml.

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“…[1][2][3] Some of these metabolites have been shown to exhibit cytotoxicity toward several caner cell lines. 1,3) Our continuing investigation on the chemical constituents of this soft coral has again led to the isolation of one novel norhumulene 1, two new norxeniaphyllanes 2 and 3, three new xeniaphyllanes 4-6, and a new xeniaphyllane-derived diterpenoid 7 possessing a rare cyclic peroxyhemiketal (3,6-dihydro-1,2-dioxin-3-ol). 2,4) We describe herein the isolation, structure elucidation and biological activity of these compounds.…”

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“…The combined extract was concentrated under reduced pressure, and the residue was fractionated by open column chromatography on silica gel. The terpenoidcontaining fractions (characterized by 1 Fig. 1.…”

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Novel Norhumulene and Xeniaphyllane-Derived Terpenoids from a Formosan Soft Coral Sinularia gibberosa

Chen

Su²,

Yeh

et al. 2009

Chem. Pharm. Bull.

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A novel skeletal norhumulene (1) and six xeniaphyllane-derived compounds, including norditerpenoids (2, 3) and diterpenoids (4-7), were isolated from the EtOAc extract of the Formosan soft coral Sinularia gibberosa. Their structures were elucidated by spectroscopic analysis. In vitro cytotoxic evaluation of the above metabolites revealed that 2 and 4 showed weak cytotoxicity toward a few cancer cell lines.

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New β-Caryophyllene-Derived Terpenoids from the Soft Coral Sinularia nanolobata

Cited by 74 publications

References 18 publications

Glycolipids from the Formosan Soft Coral Lobophytum crassum

Glycolipids from the Formosan Soft Coral Lobophytum crassum

Aktivitas Antimitotik Dari Ekstrak Karang Lunak Genus Sinularia

Novel Norhumulene and Xeniaphyllane-Derived Terpenoids from a Formosan Soft Coral Sinularia gibberosa

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