Antineoplastic Agents. 386. Isolation of Sesterstatins 1−3 from the Marine Sponge Hyrtios erecta1†

Pettit, George R.; Cichacz, Zbigniew A.; Tan, Rui; Hoard, Michael S.; Melody, Noeleen; Pettit, Robin K.

doi:10.1021/np970203+

Cited by 40 publications

(56 citation statements)

References 9 publications

(16 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The CH 2 Cl 2 -soluble residue of the alcoholic extract of the red sea sponge H. erectus was subjected to vacuum-liquid chromatography eluting with CH 2 Cl 2 -MeOH followed by silica gel column chromatography to afford four compounds (6)(7)(8)(9). While the MeOH-soluble residue was subjected to vacuum-liquid chromatography eluting with gradient CH 2 Cl 2 -MeOH followed by silica gel column chromatography and semipreparative HPLC to afford five compounds (1)(2)(3)(4)(5) (Figure 2), showed correlations which identified an indole-3-carbaldehyde structure.…”

Section: Resultsmentioning

confidence: 99%

“…Spongistatins, the most important metabolites of the genus Hyrtios discovered to date, showed powerful anticancer activity 6,7 , which encouraged an exhaustive recollection of the H. erecta sponge (600 kg wet wt.) for further chemical investigations, which afforded the antineoplastic agents sesterstatins [8][9][10] . In the present study, H. erectus collected from the Red Sea -Egypt was chemically investigated and a series of indole alkaloids were isolated, deoxyhyrtiosine A (1) and indole-3-carbaldehyde (2) isolated for the first time from the genus Hyrtios; in addition to the known indoles; 5-hydroxy-1H-indole-3-carboxylic acid methyl ester (3), 5-hydroxy-1H-indole-3-carbaldehyde (4) and hyrtiosine A (5) were obtained.…”

Section: Introductionmentioning

confidence: 99%

“…In the present study, H. erectus collected from the Red Sea -Egypt was chemically investigated and a series of indole alkaloids were isolated, deoxyhyrtiosine A (1) and indole-3-carbaldehyde (2) isolated for the first time from the genus Hyrtios; in addition to the known indoles; 5-hydroxy-1H-indole-3-carboxylic acid methyl ester (3), 5-hydroxy-1H-indole-3-carbaldehyde (4) and hyrtiosine A (5) were obtained. Three scalarane sesterterpenes: 16-hydroxyscalarolide (6), scalarolide (7) and 12-O-deacetyl-12-epi-scalarine (8), besides 5α,8α-epidioxy-cholesta-6-en-3β-ol (9) were also isolated. The structures of the isolated compounds were elucidated using 1D and 2D-NMR spectroscopy and and mass spectrometry.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Indole alkaloid from the Red Sea sponge Hyrtios erectus

Ashour

Elkhayat

Ebel

et al. 2007

Arkivoc

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Indole alkaloid from the Red Sea sponge Hyrtios erectus

Ashour

Elkhayat

Ebel

et al. 2007

Arkivoc

View full text Add to dashboard Cite

show abstract

“…The synthesis of scalaranes has already been summarized, together with a description of isolation and biological activities, in a review from 2004. 126 Since then, it has remained an active area of research, evidenced by successful syntheses of the scalaranes (+) scalarolide (218), 9,127 ( ) sester statin 4 (217), 128,129 its epimer ( ) sesterstatin 5 (220) 128,129 and (+) 16 deacetoxy 12 epi scalarafuranacetate (221) 130,131 recently appearing in the literature. Notably, the latter three completed targets exhibit potent cytotoxic activity, likely stimulating further synthetic and biological studies on related natural products and structural analogs within this compound class.…”

Section: Miscellaneous Tetracarbocyclic Sesterterpenoidsmentioning

confidence: 99%

Synthetic approaches toward sesterterpenoids

2012

View full text Add to dashboard Cite

show abstract

“…6 Some representative compounds are scalaradial 2, scalarafurans 3, scalarolides 4 4 and sesterstatins 5 and 6. 7 In spite of their interesting biological activities and challenging structures, this family of sesterterpenes has received little synthetic attention. To the best of our knowledge, only the synthesis of several compounds with the basic scalarane skeleton starting from manool, 8 methyl isocopalate 9 and methyl copalate, 10 as well as the total enantioselective biomimetic synthesis of scalarenedial 11 2 (R = H) have been published.…”

mentioning

confidence: 99%

Stereoselective construction of the tetracyclic scalarane skeleton from carvone

Abad

Agulló²,

Cuñat³

et al. 1999

Chem. Commun.

View full text Add to dashboard Cite

The tetracyclic scalarane skeleton 22 has been constructed from (S)-(+)-carvone using two intramolecular Diels-Alder reactions as key synthetic steps.An increasing number of compounds of the relatively new family of the scalarane sesterterpenoids, which show structures based on the hypothetical scalarane skeleton 1, have been isolated from different marine organisms. 1 These compounds seem to play an important ecological function 2 and some of them exhibit potentially useful biological activities, including antiinflammatory, 3 cytotoxic 4 and antifeedant 5 properties. Most of the members of this group of sesterterpenes possess a 1,4-dialdehyde moiety at C19-C20, either as actual aldehyde groups or latent as g-butenolide or furan rings, as well as a C12 oxygenated function as common structural features. Recently some compounds with an additional oxygenated function at the C3 position have also been isolated. 6 Some representative compounds are scalaradial 2, scalarafurans 3, scalarolides 4 4 and sesterstatins 5 and 6. 7 In spite of their interesting biological activities and challenging structures, this family of sesterterpenes has received little synthetic attention. To the best of our knowledge, only the synthesis of several compounds with the basic scalarane skeleton starting from manool, 8 methyl isocopalate 9 and methyl copalate, 10 as well as the total enantioselective biomimetic synthesis of scalarenedial 11 2 (R = H) have been published. However, none of these syntheses solves the incorporation of the oxygenated function at the C12 position.As part of our continuing interest in the synthesis of polycyclic natural products from readily available chiral building blocks, 12 we sought an efficient route to the scalarane sesterterpenes from carvone and we report herein a stereoselective general approach to the tetracyclic ABCD carbon framework. Explicitly, we describe the efficient preparation of the compound 22, which has the scalarane skeleton and functionalisation suitable for further elaboration into some of the more representative natural scalaranes. The synthesis of 22 is effected using (S)-carvone as a C-ring synthon which is incorporated into the tetracyclic framework following a C?CD?ABCD ring annulation strategy, using two intramolecular Diels-Alder (IMDA) reactions as key synthetic steps. 13 The synthesis commences with the preparation of the propargyl (prop-2-ynyl) compound 15, precursor of the IMDA reaction that allows the construction of the CD ring subunit (Scheme 1). The known dialkylated carvone 9, obtained in 70% overall yield from (S)-carvone by two consecutive alkylations with MeI and 3-iodopropanaldehyde diethyl acetal, 12a was stereoselectively converted into the a-epoxy ketone 10 in 92% yield by treatment with alkaline H 2 O 2 . Treatment of 10 with the lithium derivative of methoxymethyl(diphenyl)phosphine oxide Scheme 1 Reagents and conditions: i, LDA, THF, 210°C then CH 3 I; ii, LDA, HMPA-THF, 278°C then (EtO) 2 CHCH 2 CH 2 I, 70% from 7; iii, H 2 O 2 , NaOH, MeOH, room temp., 92%; i...

show abstract

Antineoplastic Agents. 386. Isolation of Sesterstatins 1−3 from the Marine Sponge Hyrtios erecta^1†

Cited by 40 publications

References 9 publications

Indole alkaloid from the Red Sea sponge Hyrtios erectus

Indole alkaloid from the Red Sea sponge Hyrtios erectus

Synthetic approaches toward sesterterpenoids

Stereoselective construction of the tetracyclic scalarane skeleton from carvone

Contact Info

Product

Resources

About