Novel Bishomoscalarane Sesterterpenes from the Sponge Phyllospongia foliascens

Zeng, Lang; Fu, X.; Su, Jingyu; Pordesimo, Evamarie O.; Traeger, Sarah C.; Schmitz, Francis J.

doi:10.1021/np50074a012

Cited by 31 publications

(60 citation statements)

References 8 publications

(13 reference statements)

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“…The 1 H and 13 C NMR data of 6 were very similar to those of phyllofenone B ( 8 ), previously isolated from the sponge Phyllospongia foliascen s, 7 except for the signals due to the oxygen-bearing carbon at C-12 (δ 83.2), the hydroxyl group at C-22, and the methyl group at C-21. The β-orientation of the hydroxyl group at C-12 and the configuration of C-18 were deduced from the NOESY cross peaks between H-22 and H-21, H-22 and H-19, H-19 and H-23, H-23 and H-25, and H-12 and H-18 (Figure 3).…”

Section: Resultssupporting

confidence: 69%

Antiproliferative homoscalarane sesterterpenes from two Madagascan sponges

Harinantenaina

Brodie

Maharavo³

et al. 2013

Bioorganic & Medicinal Chemistry

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Dereplication of the antiproliferative ethyl acetate fraction of the Madagascan sponge Carteriospongia sp. led to the detection and isolation of the two known homoscalarane-type sesterterpenes 1 and 2. Investigation of a similar sponge containing closely related compounds afforded the four new antiproliferative homoscalarane sesterterpenes (3, 5 –7). The structures of all isolated compounds were elucidated by spectroscopic methods, including UV, IR and 1D- and 2D-NMR. Compounds 1, 3 and 5 displayed submicromolar antiproliferative activity against the A2780 ovarian cell line with IC50 values of 0.65, 0.26 and 0.28 μM, respectively, while compounds 6 and 7 showed moderate activity (4.5 and 8.7 μM, respectively). Compounds 3 and 5 also displayed anti-proliferative activity against the H522-T1 non-small cell lung and A2058 human melanoma cancer cell lines.

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Section: Resultssupporting

confidence: 69%

Antiproliferative homoscalarane sesterterpenes from two Madagascan sponges

Harinantenaina

Brodie

Maharavo³

et al. 2013

Bioorganic & Medicinal Chemistry

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“…Interestingly, a linear furan sesterterpene 5,10-dihydroxyfurospinulosine-1 (165) [73] was discovered simultaneously from the same sponge, playing a possible biogenetic role as a precursor to the related sesterterpenoids. The sponge Phyllospongia foliascens, on the other hand, produced a further thirteen scalaranes (166)(167)(168)(169)(170)(171)(172)(173)(174)(175)(176)(177)(178) [74][75][76][77][78][79] and phyllofenone B (179) which have an unprecedented carbon skeleton derived from scalarane [75]. The determination of the absolute stereochemistry of phyllactone B (168) permitted the assignments of the absolute stereochemistry of all the scalaranes from the Chinese species [78] to be verified.…”

Section: Spongesmentioning

confidence: 99%

“…The determination of the absolute stereochemistry of phyllactone B (168) permitted the assignments of the absolute stereochemistry of all the scalaranes from the Chinese species [78] to be verified. Bio-screening experiments revealed the potent cytotoxicities of phyllofenone B (179) against P-388 [75], and of the phyllactones A (172) and B (173) against KB cell lines [77].…”

Section: Spongesmentioning

confidence: 99%

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Secondary Metabolites from the South China Sea Invertebrates: Chemistry and Biological Activity

Zhang

Guo²,

Gu³

2006

CMC

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The increasing demand for new lead compounds in the pharmaceutical and agrochemical industries has driven scientists to search for new sources of bioactive natural products. Marine invertebrates are a rich source of novel, bioactive secondary metabolites and they have attracted a great deal of attention from scientists in the fields of chemistry, pharmacology, ecology, and molecular biology. During the past 25 years, many complex and structurally unique secondary metabolites have been isolated from the invertebrates inhabiting the South China Sea. These metabolites are responsible for various bioactivities such as anti-tumor, anti-inflammation and antioxidant activities, and/or they act on the cardiovascular system. This review will focus on the marine natural product chemistry of invertebrates from the South China Sea, aiming to give the reader a brief view of the compounds isolated from these invertebrates, as well as their biological activities. The article covers the literature published during the period from the beginning of 1980 to the end of 2005, with 340 citations and 811 compounds from invertebrates from the South China Sea, including sponges, coelenterates, molluscs and echinoderms.

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“…Phyllofenone D (2) was cytotoxic against the P388 leukemia cell line with an IC 50 value of 6.5 mg/ml. [7], and phyllofolactones [7] [8]. In our continuing studies on bioactive constituents of marine sponges collected from the South China Sea, the acetone extract of P. foliascens showed significant antineoplastic activity in vitro.…”

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confidence: 99%

Scalarane Sesterterpenes from the Chinese Sponge Phyllospongia foliascens

Zhang

Tang

et al. 2009

Helvetica Chimica Acta

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Three new scalarane sesterterpenes, phyllofolactone L (1), phyllofenone D (2) and phyllofenone E (3), were isolated from the acetone extract of the South China Sea sponge Phyllospongia foliascens. Their structures were elucidated on the basis of spectroscopic analysis. Phyllofenone D (2) was cytotoxic against the P388 leukemia cell line with an IC 50 value of 6.5 mg/ml. [7], and phyllofolactones [7] [8]. In our continuing studies on bioactive constituents of marine sponges collected from the South China Sea, the acetone extract of P. foliascens showed significant antineoplastic activity in vitro. Bioassay-guided separation led to the isolation of two new 24-homoscalarane sesterterpenes, phyllofolactone L (1) and phyllofenone D (2), and a new 20,24-bishomo-25-norscalarane sesterterpene, phyllofenone E (3), from this sponge. The details of isolation and structure elucidation are reported in this work.

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Novel Bishomoscalarane Sesterterpenes from the Sponge Phyllospongia foliascens

Cited by 31 publications

References 8 publications

Antiproliferative homoscalarane sesterterpenes from two Madagascan sponges

Antiproliferative homoscalarane sesterterpenes from two Madagascan sponges

Secondary Metabolites from the South China Sea Invertebrates: Chemistry and Biological Activity

Scalarane Sesterterpenes from the Chinese Sponge Phyllospongia foliascens

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