New tetracyclic and pentacyclic isomalabaricanes from the marine sponge Rhabdastrella globostellata (Carter, 1883)

Trang, Đỗ Thị; Dung, Dương Thị; Nhiệm, Nguyễn Xuân; Cúc, Nguyễn Thị; Yến, Phạm Hải; Hằng, Đan Thị Thúy; Linh, Trần Mỹ; Chi, Nguyen; Hương, Phan Thị Thanh; Tài, Bùi Hữu; Kiệm, Phan Văn

doi:10.1016/j.tetlet.2021.153607

Cited by 11 publications

(13 citation statements)

References 16 publications

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“…Compounds 3-5 were identified as 25,26,27-tri-nor-cholesta-2β,3α,24-triol-2,3,24-trisulfate (solomonsterol A, 3), 9,10 1-O-arachidonoyl-3-O-stearylglycerol (4), 13 and eicosapentaenoic acid (5) 14 by the coincidence between their NMR spectral data and those of the corresponding reported data, and further confirmed by HSQC and HMBC spectra. Compounds 6-8 were identified as adenosine (6), adenine (7), and uracil (8) 15 by analyzing their 1 H NMR data, and comparison with authentic samples by HPLC analysis. Compounds 3-8 are reported for the first time from L. lambis.…”

Section: Resultsmentioning

confidence: 99%

“…Thin layer chromatography was carried out on pre-coated silica gel 60 F 254 and/or RP-18 F 254S plates. known compounds (3)(4)(5)(6)(7)(8) were isolated. Their chemical structures were elucidated as 25,26,27-tri-nor-cholest-5-ene-2β,3α,24-triol-2,24-disulfate (1), 25,26,27-tri-nor-cholesta-2β,3α, 24-triol-3,24-disulfate (2), and 25,26,27-tri-nor-cholesta-2β,3α, 24-triol-2,3,24-trisulfate (3), 1-O-arachidonoyl-3-O-stearylglycerol (4), eicosapentaenoic acid (5), adenosine (6), adenine (7), and uracil (8) based on extensive spectroscopic methods, including HRESIMS, 1D-and 2D-NMR spectra.…”

Section: Methodsmentioning

confidence: 99%

“…3 The mucus extract of L. lambis exhibited cytotoxic activity. 4 Continuing our program of study on Vietnamese marine organisms, [5][6][7][8] we report in this paper the isolation and structural elucidation of two new sterol sulfates (1 and 2) and six known compounds (3)(4)(5)(6)(7)(8) from the methanol extract of the sea spider conch L. lambis.…”

Section: Introductionmentioning

confidence: 99%

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Two New Sterol Sulfates from Marine Spider Conch Lambis Lambis Linnaeus, 1758

Dan

Giang

Dinh

et al. 2022

Natural Product Communications

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Two new (1 and 2) and six known (3-8) compounds were isolated from the methanolic extract of the Vietnamese marine spider conch Lambis lambis Linnaeus, 1758. Based on comprehensive spectroscopic analyses, particularly HRESIMS, and 1D- and 2D-NMR spectra, their chemical structures were determined to be 25,26,27-tri-nor-cholest-5-ene-2 β,3 α,24-triol-2,24-disulfate (1), 25,26,27-tri-nor-cholesta-2 β,3 α,24-triol-3,24-disulfate (2), 25,26,27-tri-nor-cholesta-2β,3α,24-triol-2,3,24-trisulfate (solomonsterol A, 3), 1- O-arachidonoyl-3- O-stearylglycerol (4), eicosapentaenoic acid (5), adenosine (6), adenine (7), and uracil (8). This is the first report of compounds 3-8 from L. lambis.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Two New Sterol Sulfates from Marine Spider Conch Lambis Lambis Linnaeus, 1758

Dan

Giang

Dinh

et al. 2022

Natural Product Communications

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“…By collecting vouchers and voucher pictures, we noticed some shape variations in R. globostellata . This species is usually a massive subglobular species which can be cup-shaped in large specimens ( Figure 3 B), but a morphotype with a convoluted surface (brain-like) seemed also quite common ( Figure 3 A) in the South and East China Sea: ZMAPOR 16401 from Hirashima et al [ 55 ], ZMAPOR 12451 from Rao et al [ 19 ], PIBOC O38-301 from Kolesnikova et al [ 35 , 65 ], HM06-2016.1 from Kiem et al [ 62 ] and NCCT-B139 from Trang et al [ 66 ]. Morphology and measurements of the spicules from both morphotypes did not reveal any consistent differences.…”

Section: Discussionmentioning

confidence: 99%

Good Practices in Sponge Natural Product Studies: Revising Vouchers with Isomalabaricane Triterpenes

et al. 2022

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Species misidentification in the field of natural products is an acknowledged problem. These errors are especially widespread in sponge studies, albeit rarely assessed and documented. As a case study, we aim to revisit reports of isomalabaricane triterpenes, isolated from four demosponge genera: Jaspis, Geodia, Stelletta and Rhabdastrella. From a total of 44 articles (1981–2022), 27 unique vouchers were listed, 21 of which were accessed and re-examined here: 11 (52.4%) of these were misidentified. Overall, 65.9% of the studies published an incorrect species name: previously identified Jaspis and Stelletta species were all in fact Rhabdastrella globostellata. We conclude that isomalabaricane triterpenes were isolated from only two Rhabdastrella species and possibly one Geodia species. In addition to shedding a new light on the distribution of isomalabaricane triterpenes, this study is an opportunity to highlight the crucial importance of vouchers in natural product studies. Doing so, we discuss the impact of species misidentification and poor accessibility of vouchers in the field of sponge natural products. We advocate for stricter voucher guidelines in natural product journals and propose a common protocol of good practice, in the hope of reducing misidentifications in sponge studies, ensure reproducibility of studies, and facilitate follow-up work on the original material.

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“…The used characterization equipment is the same as described in our previous work. 30 Refer to Supplemental Material.…”

Section: General Experimental Proceduresmentioning

confidence: 99%

Halipanasterol, a New Sterol Isolated From the Marine Sponge Halichondria panicea

Kiệm

Trang

Tài

et al. 2022

Natural Product Communications

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A new sterol (1) and 8 known (2-9) compounds were isolated from the methanol extract of the Vietnamese marine sponge Halichondria panicea (Pallas, 1766) by various chromatographic methods. Their chemical structures were determined as 5 α,6 α-epoxy-(22 E)-ergosta-3 β,7 α-diol-8,22,25-triene (1), (22 E)-ergosta-7,22,25-triene-3 β,5 α,6 β-triol (2), 3 β-hydroxycholest-5ene-7-one (3), cholesterol sulfate (4), 3-formamidotheonellin (5), para-hydroxybenzylideneacetone (6), indole-3-carbaldehyde (7), thymidine (8), and adenosine (9) by using a combination of HR-ESI-MS, 1D and 2D NMR spectral data, as well as by comparison with the previous literature. This is the first report of these compounds from H panicea. Compounds 1 and 2 exhibited cytotoxic effects on Hep-G2, SK-Mel-2, LU-1, and MCF-7 cell lines with IC50 values of 9.27 ± 1.25, 11.34 ± 1.18, 15.45 ± 1.47, and 10.85 ± 1.19 µM (for 1), and 6.45 ± 0.77, 9.74 ± 1.03, 7.08 ± 0.64, 5.61 ± 0.39 µM (for 2), compared to the positive control compound, ellipticine, 1.60 ± 0.37, 2.53 ± 0.51, 1.82 ± 0.20, and 2.17 ± 0.66 µM, respectively.

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New tetracyclic and pentacyclic isomalabaricanes from the marine sponge Rhabdastrella globostellata (Carter, 1883)

Cited by 11 publications

References 16 publications

Two New Sterol Sulfates from Marine Spider Conch Lambis Lambis Linnaeus, 1758

Two New Sterol Sulfates from Marine Spider Conch Lambis Lambis Linnaeus, 1758

Good Practices in Sponge Natural Product Studies: Revising Vouchers with Isomalabaricane Triterpenes

Halipanasterol, a New Sterol Isolated From the Marine Sponge Halichondria panicea

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