Phorbasterones A−D, Cytotoxic <i>Nor</i>-Ring A Steroids from the Sponge <i>Phorbas amaranthus</i>

Masuno, Makoto N.; Pawlik, Joseph R.; Molinski, Tadeusz F.

doi:10.1021/np034037j

Cited by 30 publications

(43 citation statements)

References 17 publications

(45 reference statements)

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“…All 1 H NMR and 13 C NMR signals could be unambiguously assigned by 2D NMR measurements (COSY, HMBC, HSQC, and NOESY). Previously, compound 10 was isolated from the sponge Phorbas amaranthus by Molinski et al and named phorbasterone B [27]. Our 1 H NMR and 13 C NMR data are in full agreement with those reported in the literature ([27], Table 2, and Section 3.3.…”

Section: Resultssupporting

confidence: 89%

“…In addition to a mixture of cholesterol ( 5 ) and 24-methyl-25-homocholesterol ( 8 ), as isolated from Spyridia sp. (see above), the two A-ring contracted steroids, (−)-2-ethoxycarbonyl-2β-hydroxy-A-norcholest-5-en-4-one ( 9 ) [26] and (−)-2-methoxycarbonyl-2-hydroxy-A-nor-cholest-5-en-4-one [phorbasterone B ( 10 )] [27], and cholest-4-ene-3,6-dione ( 11 ) were isolated from the diethyl ether fraction of Calloseris sp. (Figure 4).…”

Section: Resultsmentioning

confidence: 99%

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Red Algae (Rhodophyta) from the Coast of Madagascar: Preliminary Bioactivity Studies and Isolation of Natural Products

et al. 2015

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Several species of red algae (Rhodophyta) from the coastal regions of Madagascar have been investigated for their natural products. The most abundant compound was cholesterol (5) in combination with a series of oxidized congeners. The brominated indoles 1–3 along with the sesquiterpene debilone (4) have been isolated from Laurencia complanata. For the first time, debilone (4) has been obtained from a marine plant. From the methanol extract of Calloseris sp., we have achieved the second isolation of the unusual A-ring contracted steroids (−)-2-ethoxycarbonyl-2β-hydroxy-A-nor-cholest-5-en-4-one (9) and phorbasterone B (10). The crude extracts of Laurencia complanata exhibited antimicrobial activity against Bacillus cereus, Staphylococcus aureus, Streptococcus pneumoniae, and Candida albicans.

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Section: Resultssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Red Algae (Rhodophyta) from the Coast of Madagascar: Preliminary Bioactivity Studies and Isolation of Natural Products

et al. 2015

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“…An aliquot (1.73 g) of the fraction eluted with 10% MeOH(aq) was dried and separated by reversed-phase HPLC (YMC-ODS-A column, 20% MeOH(aq)) to afford, in the order of elution, compounds 13, 11,6,3,8,5,4,15,9,7,12,14,2, and 1 as white solids. An aliquot (1.75 g) of the fraction eluted with 100% MeOH was dried and separated by reversed-phase HPLC (YMC-ODS-A column, 15% MeOH(aq)) to afford, in the order of elution, compounds 4, 12, 2, 1, 16, 10, and 17 as white solids.…”

Section: Methodsmentioning

confidence: 99%

“…Ten new polyoxygenated diterpenes (7)(8)(9)(10)(11)(12)(13)(14)(15)(16) along with six known gagunin compounds (1)(2)(3)(4)(5)(6) were isolated from the sponge Phorbas sp. collected in the Korean Sea.…”

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confidence: 99%

Polyoxygenated Diterpenes from the Sponge Phorbas sp.

et al. 2008

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Ten new polyoxygenated diterpenes (7-16) along with six known gagunin compounds (1-6) were isolated from the sponge Phorbas sp. collected in the Korean Sea. On the basis of a combination of NMR and mass spectroscopic analyses, the molecular structures of these diterpenes, designated as gagunins H-Q, were determined to be penta- or hexa-oxygenated diterpenes of the 10,13-bis-epi-homoverrucosane class. A new diterpene acid (17) of a bisabolane-related skeletal class was also isolated and structurally defined by the spectroscopic analyses. These compounds exhibited moderate to significant cytotoxicity against the K-562 cell line as well as weak inhibitory activity against isocitrate lyase (ICL).

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“…1) In our search for bioactive natural products from marine sponges, three new diterpenoids were isolated from the extract of the sponge Phorbas gukulensis with the cytotoxic gagunin A-D compounds reported previously. 2) In the literature survey, metabolites from the genus Phorbas were reported to feature heterocyclic phorboxazoles, 3) phorbazoles, 4) phobasterones, 5) and diterpene phorbasins.…”

mentioning

confidence: 99%