Sesquiterpenoids and Artificial 19-Oxygenated Steroids from the Formosan Soft Coral <i>Nephthea erecta</i>

Cheng, Shi‐Yie; Dai, Chang‐Feng; Duh, Chang‐Yih

doi:10.1021/np070189t

Cited by 37 publications

(38 citation statements)

References 16 publications

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“…133 Chemical investigations of the soft coral Nephthea erecta have afforded three new sesquiterpenoids 246-248, of which, 247 and 248 exhibited significant cytotoxicty against P388 and HT-29. 134 The Formosan soft coral Nephthea erecta provided the sesquiterpenoid 249. 135 Five sesquiterpene peroxides sinularioperoxides 250-254 have been isolated from a Formosan soft coral of the genus Sinularia by the same group.…”

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confidence: 99%

Peroxy natural products

Liu

2013

Nat. Prod. Bioprospect.

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confidence: 99%

Peroxy natural products

Liu

2013

Nat. Prod. Bioprospect.

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“…HMBC correlations of methyl protons at G H 1.23 (Me-15) with the carbons at G C 27.3 (C-3), 31.9 (C-4), and 82.7 (C-5) suggested that the methyl group was connected to C-4. On the basis of the above evidence, the planar structure of 1 was unambiguously established, and 1 had the same planar structure as 5E,8E-epidioxy-11-hydroperoxy-6-eudesmene [11].…”

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confidence: 83%

A novel eudesmene sesquiterpenoid from Schisandra sphenanthera stems

Tan²,

et al. 2011

Chem Nat Compd

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Chemical investigation on the stems of Schisandra sphenanthera has afforded a novel eudesmene-type sesquiterpenoid, schisansphene A (1), and a known compound, alismol (2). Their structures and configurations were elucidated by spectroscopic methods, including 2D NMR techniques.The family Schisandraceae has been proved to be a rich source of dibenzocyclooctane lignans, as well as lanostane and cycloartane triterpenes, some of which have been found to possess calcium antagonism, anti-lipid peroxidation, antitumor, anti-HIV and anti-HBV effects [1][2][3][4][5][6][7][8]. In our previous study, three carotane-type sesquiterpenoids, schisanwilsonenes A-C, were obtained from S. wilsoniana, and schisanwilsonene A was found to show an active effect against HBV [9]. Schisandra sphenanthera Rehd. et Wils. is a medicinal plant indigenous to southern China. Its fruits are used in Chinese folk medicine as "wu-wei-zi" to treat hepatitis.In a systemic phytochemical investigation, a new eudesmene-type sesquiterpenoid, schisansphene A (1), and a known guainane-type sesquiterpenoid, alismol (2) [10], were isolated from the stems of S. sphenanthera. This is the first report of eudesmene and guainane sesquiterpenoids from the Schisandraceae. In this paper, we describe the isolation and structure of the new compound.Compound 1, a white powder, had the molecular formula C 15 H 24 O 3 on the basis of HR-ESI-MS (m/z 275.1621 [M + Na] + ), which indicated four degrees of unsaturation. The IR absorption band at 3414 cm -1 implied the presence of the OH group. The 1 H NMR spectrum showed signals corresponding to an oxygenated methine proton [G 4.82 (1H, m)], an olefinic proton [6.36 (1H, s)], a secondary methyl [1.23 (3H, d, J = 7.2 Hz)], and three tertiary methyls [0.98, 1.37, and 1.51 (each 3H, s)]. The 13 C NMR displayed 15 carbon resonances, and the DEPT spectrum was consistent with the presence of a methine [G 71.0 (d)], a quaternary carbon [82.7 (s)] bearing a peroxide ring, a quaternary carbon [81.8 (s)] bearing a hydroxyl, and trisubstituted olefinic carbons [128.0 (d) and 146.2 (s)], as well as four methyls, four methylenes, three methines, and four quaternary carbons.

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“…Some of them exhibited cytotoxic and antiinflammatory activities Examination of the acetone and methanol extracts of N. erecta also yielded five new sesquiterpenoids 5β,8β-epidioxy-11-hydroxy-6-eudesmene (57), 5β,8β-epidioxy-11-hydroperoxy-6-eudesmene (58), 3,4-epoxy-11-hydroxy-1-pseudoguaiene (59), 8β-hydroxyprespatane (60) and 8β-hydroperoxyprespatane (61) [37]. …”

Section: Nephthea Elongatamentioning

confidence: 99%

Chemical Constituents and Biological Properties of the Marine Soft Coral <em>Nephthea</em>: A Review (Part 1)

Amir¹,

Koay²,

Yam³

2012

Trop. J. Pharm Res

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The genus Nephthea is a member of the family Acyonaceae, subfamily Nephtheidae, and is distributed throughout the world mainly in the Indo-Pacific region. The genus Nephthea has been studied for its phytochemical constituents and these studies have resulted in the discovery of over a hundred compounds comprising amides, sesquiterpenes, diterpenes and steroids. Corresponding biological activities such as anti-inflammatory and cytotoxic activities have also been observed for some of the isolated constituents. Among the isolated constituents, steroids are the most abundant followed by diterpenes and sesqui biological activities reported for twelve species of the genus Nephthea, namely, N. albida, N. armata, N. bayeri, N. brassica, N. capnelliformis, N. crassica, N. elongata, N. erecta, N. hainansis, N. pacifica, N. chabrolii and N. sinulata

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Sesquiterpenoids and Artificial 19-Oxygenated Steroids from the Formosan Soft Coral Nephthea erecta

Cited by 37 publications

References 16 publications

Peroxy natural products

Peroxy natural products

A novel eudesmene sesquiterpenoid from Schisandra sphenanthera stems

Chemical Constituents and Biological Properties of the Marine Soft Coral <em>Nephthea</em>: A Review (Part 1)

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