Isolation of meso-1,3-Diphenyl-1,3-propanediol from a Soft Coral Nephthea Sp.

Ray, Anup Kumar; Datta, Pran K.; Das, Tapas; Bhattacharyya, P.; Barua, A.K.; Patra, A. P.; Acharyya, Aditi

doi:10.1021/np50075a016

Cited by 5 publications

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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.…”

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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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confidence: 93%

Polyhydroxylated Steroids and Other Constituents of the Soft Coral Nephthea chabroli

Zhang¹,

Liu

Che

2003

Chem. Pharm. Bull.

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“…369 A dimer (588) and trimer (589) of acetone (+ammonia) have been reported as metabolites of an Indian specimen of Lobophytum strictum that was extracted with acetone.370 The total syntheses of clavulones I-IV (590)-(593), which are prostanoids from the soft coralClavularia viridi~,~~~ have been 9 BryozoansA study of the cytotoxic constituents of Cribricellina cribraria from New Zealand resulted in the isolation of l-vinyl-8-3-carboline (594) as the major cytotoxic component together with 1-ethyl-4-methylsulfone-/3-carboline (595) and…”

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confidence: 99%