New Oxygenated Sesquiterpenes from the Indonesian Soft Coral <i>Nephthea chabrolii</i>

Handayani, Dian; Edrada, Ru Angelie; Proksch, Peter; Wray, Victor; Witte, Ludger; Ofwegen, Leen van; Kunzmann, Andreas

doi:10.1021/np960699f

Cited by 71 publications

(61 citation statements)

References 12 publications

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“…In addition to developments summarized in our earlier paper, a new sesquiterpene, hydroxycolorenone (6), was isolated from the soft coral Nephithea chabrolii, which showed strong insecticidal activity with an EC 50 35 μM and an LC 50 1.8 mM against neonate larvae of the polyphagous pest insect Spodoptera littoralis (12). The marine-derived β-carboline alkaloid manzamine A (7) was reported to exhibit insecticidal activity toward neonate larvae of the polyphagous pest insect S. littoralis with an ED 50 of 63 μM (13).…”

Section: Marine Natural Products As Insecticides Herbicides and Funmentioning

confidence: 89%

“…The marine-derived β-carboline alkaloid manzamine A (7) was reported to exhibit insecticidal activity toward neonate larvae of the polyphagous pest insect S. littoralis with an ED 50 of 63 μM (13). (12) and N-(3-oxo-1-butenyl) renierone (13) exhibited weak insecticidal activity against S. littoralis.…”

Section: Marine Natural Products As Insecticides Herbicides and Funmentioning

confidence: 99%

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Marine Natural Products as Prototype Agrochemical Agents

Peng

Shen²,

Ka³

et al. 2003

J. Agric. Food Chem.

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In the interest of identifying new leads that could serve as prototype agrochemical agents, 18 structurally diverse marine-derived compounds were examined for insecticidal, herbicidal, and fungicidal activities. Several new classes of compounds have been shown to be insecticidal, herbicidal, and fungicidal, which suggests that marine natural products represent an intriguing source for the discovery of new agrochemical agents.

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Section: Marine Natural Products As Insecticides Herbicides and Funmentioning

confidence: 89%

Section: Marine Natural Products As Insecticides Herbicides and Funmentioning

confidence: 99%

Marine Natural Products as Prototype Agrochemical Agents

Peng

Shen²,

Ka³

et al. 2003

J. Agric. Food Chem.

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“…[5][6][7][8][9] In the present paper, we report the isolation of eight sterols (1-8), a diterpene glycoside (9), a ceramide (10), a quinoline (11), and fatty acid derivatives (12-13). Of these constituents, 6 and 8 are new structures.…”

Section: )mentioning

confidence: 93%

Polyhydroxylated Steroids and Other Constituents of the Soft Coral Nephthea chabroli

Zhang¹,

Liu

Che

2003

Chem. Pharm. Bull.

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Soft corals contain a variety of bioactive compounds such as diterpenes, sesquiterpenes, and steroids. 1) In the course of our search for biologically active substances from marine organisms, 2-4) a collection of the soft coral Nephthea chabroli was obtained from the South China Sea, and from this collection, cembrane diterpenes and norditerpenes (chabrolols A-C) were obtained.2) Another chemical constituent, lemnabourside, was found to show anti-proliferative and 5a-reductase inhibitory effect on human prostate cancer cells. 3)In the literature, secondary metabolites including benzoquinone derivatives, sesquiterpenes, and sterols have been reported from Nephthea chabroli. [5][6][7][8][9] In the present paper, we report the isolation of eight sterols (1-8), a diterpene glycoside (9), a ceramide (10), a quinoline (11), and fatty acid derivatives (12-13). Of these constituents, 6 and 8 are new structures.Compounds 1-6 displayed characteristic spectral features of 19-hydroxylated steroids, 10,11) showing in their NMR spectra a pair of methylene proton doublets at about d H 3.7 (1H, Jϭ12 Hz) and 3.9 (1H, Jϭ12 Hz), as well as a methylene carbon signal at d C 63.2 (t). The structures of 1-5 were determined to be 24-methylcholesta-5,24(28)-diene-3b,19-diol (1), 12,13) 24-methylcholesta-5,24(28)-diene3b,7b,19-triol (2), 12,13) 24-methyl-7b-acetoxycholesta-5,24(28)-diene-3b,19-diol (3), 12,13) 24-methylcholest-24(28)-ene-3b,5a,6b,19-tetraol (4), 12,13) and 24-methyl-7-oxocholesta-5,24(28)-diene-3b,19-diol (5).12) The structural identities of these compounds were established by comparing the physical and spectroscopic data with literature values.Compound 6 ) and a terminal methylene (1640, 900 cm Ϫ1 ). The presence of a primary hydroxyl and two secondary hydroxyl groups was revealed by 1 H-and With the assistance of computer-aided molecular modeling (MOPAC molecular modeling program), the energy-minimized stereostructure of 6 showed the dihedral angle (j) between H 11 -C 11 -C 12 -H 12 to be 37.7°, corresponding to a coupling constant of 2-5 Hz as estimated from the Karplus correlation graph. Given a coupling constant of 4 Hz for H-12, b-orientation of 12-H was assumed. Indeed, the nuclear Overhauser effect spectroscopy (NOESY) spectrum displayed correlation signals between H 12 /H 18 as well as between H 11 /H 12 . These NOE results were in support of the stereochemical assignment. Hence, all available data indicated a structure of 24-methylcholesta-9(11),24(28)-diene-3b,12a,19-triol for 6.Compound 7 was determined to be 24-methylcholesta-5,24(28)-dien-3b-ol by interpretation of its spectroscopic data and comparison with literature values. Polyhydroxylated steroids and other metabolites were isolated from the soft coral Nephthea chabroli collected in South China Sea. The structures of two new compounds were determined to be 24-methylcholesta-9(11), 24(28)-diene-3b b,12a a,19-triol and 4a a-methyl-3b b,14b b-dihydroxy-5a a-ergost-24(28)-en-23-one on the basis of spectroscopic analysis. Cytotoxic activities of the po...

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“…Chemical investigation of soft corals of the genus Nephthea (i.e. N. chabrolii [3][4][5][6][7]14 , N. brassica, 8,15,16 N. tixera, 11 N. albida 11,12 , N. erecta 13 and other Nephthea spp. 9,10,[17][18][19][20][21][22] ) collected from various locations led to the isolation of varied extractives viz., sesquiterpenoids (guaianes 3,4,6,7,8,22 and eudesmanes 17,21 ), tetraprenylbenzenoids 9,21 , diphenylpropane-1,3-diol 10 , sterols (24-methylenecholesterols [11][12][13][14][15][16] ) and diterpenoids (bicyclic 6,22 , brassicolides, 8 xeniaphyllanes 17 , and cembranes [18][19][20]23,24 ).…”

Section: Introductionmentioning

confidence: 99%