Marine Sterols. XXII. Occurrence of 3-Oxo-4,6,8(14)-triunsaturated Steroids in the Sponge Dysidea herbacea.

Kobayashi, Masaru; Krishna, M. M.; Ishida, Keisuke; Anjaneyulu, V.

doi:10.1248/cpb.40.72

Cited by 46 publications

(40 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Known compounds were identified as (4,4,14-trimethyl-3-oxo-24-nor-5α,13α,14β,17α,20S-chol-7-en-23-oic acid) (3), 16 hydroxydammarenone I (4), 17 ocotillone (5), 18 stigmasta-4-ene-3-one (6), 19 stigmasta-4,6,8(14),22-tetraen-3-one (7), 20 artelin (8), 21 polystachyol (9), 22 coniferyl alcohol (10), ferulic acid (11), 2,6-dimethoxyhydroquinone (12), antiarol (13), and 4-hydroxybenzaldehyde (14) by comparison with published literature data or direct identification by spectroscopic evidences. It was noted that compound 3 has been synthesized previously, 16 however, it was isolated from natural sources for the first time.…”

Section: Resultsmentioning

confidence: 99%

Triterpenoids and Sterones from the Stem Bark of Ailanthus altissima

Zhou¹,

Xu²,

Li³

et al. 2011

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

One new tirucallane-type triterpenoid, alianthusaltinin A (1), one new C29 sterone, alianthaltone A (2), and 12 known compounds have been isolated from the stem bark of Ailanthus altissima. The structures of new compounds were identified by means of spectroscopic methods. Compound 3 was isolated from natural sources for the first time, and compounds 4, 5, and 9 were isolated from this plant for the first time.

show abstract

Section: Resultsmentioning

confidence: 99%

Triterpenoids and Sterones from the Stem Bark of Ailanthus altissima

Zhou¹,

Xu²,

Li³

et al. 2011

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

show abstract

“…1 and S1) including nine new chemical entities for bioactive assay. In this Letter, we describe the isolation and structural determination of tripolinolate A (1) from T. vulgare, the synthesis of tripolinolate A and its analogs (13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31), and the activity of compounds (1-31) in suppressing the proliferation of glioma and colorectal cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

Chen

Liang

Song

et al. 2015

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

“…A comparison of the experimental results and the literature on 5 identified it as 24-methylenecholesta-4,6,8(14)-trien-3-one. At present, only anecdotal instances of the isolation of ketosteroids with a similar unusual core are known from natural specimens [11][12][13]. 24-Methylenecholesta-…”

mentioning

confidence: 99%

“…The 4,6,8(14)-trien-3-one was isolated from sponges of the genus Penares for the first time although it was found earlier in steroid fractions from the sponge Dysidea herbacea [11].…”

mentioning

confidence: 99%

Secondary Metabolites of the Marine Sponge Penares cf. schulzei, Fluorescence Properties of 24-Methylenecholesta-4,6,8(14)-Trien-3-One

et al. 2015

View full text Add to dashboard Cite

Marine sponges of the genus Penares are known as sources of various low-molecular-weight secondary metabolites including bioactive indoles, azetidine alkaloids [1], unusual triterpenoids [2, 3], proline-containing macrolides [4], and sphingolipids [5]. In continuation of our research on natural compounds from sponges of this genus inhabiting the littoral waters of Vietnam [6,7], we communicate about slightly polar components of the EtOH extract of P. cf. schulzei (dry weight 22.1 g) collected during an expedition of the RV Akademik Oparin near the shores of Vietnam. We isolated and elucidated the structures of five ketosteroids. The composition of the low-molecular-weight metabolites of the sponge was studied for the first time.Compounds 1, 2, and 3 (6.7, 2.1, and 6.4 mg) were isolated by combined column chromatography over Sephadex LH-20 (CHCl 3 -MeOH, 1:1) and silica gel (n-hexane-EtOAc, 4:1) followed by reversed-phase HPLC over a YMC-Pack ODS-A column (9.4 u 250 mm, EtOH-H 2 O, 98:2). Ketones 4 and 5 (1.3 and 2.3 mg) were also obtained pure after rechromatography of the respective fractions over a normal-phase Ultrasphere TM Si column (9.4 u 250 mm; hexane-EtOAc, 5:1 for 4 and CHCl 3 -EtOH, 300:1 for 5).The structures of compounds 1-4 were elucidated using NMR spectroscopy and GC-MS as 24-methylenecholest-4-ene-3,6-dione (1) and cholest-4-ene-3,6-dione (2) [8], ergosta-4,24(28)-dien-3-one (3) and cholest-4-en-3-one (4) [9, 10]. Compounds 1, 2, and 4 were not observed earlier in sponges of the genus Penares. We isolated compound 3 from a Penares sp. of sponge [7].The PMR spectrum of 5 exhibited a series of methyl resonances at 0.96 contained a peak for the molecular ion [M + H] + (m/z 393.3154) that corresponded to the formula C 28 H 40 O. A comparison of the experimental results and the literature on 5 identified it as 24-methylenecholesta-4,6,8(14)-trien-3-one. At present, only anecdotal instances of the isolation of ketosteroids with a similar unusual core are known from natural specimens [11][12][13]. 24-Methylenecholesta-

show abstract

Marine Sterols. XXII. Occurrence of 3-Oxo-4,6,8(14)-triunsaturated Steroids in the Sponge Dysidea herbacea.

Cited by 46 publications

References 1 publication

Triterpenoids and Sterones from the Stem Bark of Ailanthus altissima

Triterpenoids and Sterones from the Stem Bark of Ailanthus altissima

Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs

Secondary Metabolites of the Marine Sponge Penares cf. schulzei, Fluorescence Properties of 24-Methylenecholesta-4,6,8(14)-Trien-3-One

Contact Info

Product

Resources

About