New isomalabaricane analogues from the sponge Rhabdastrella providentiae and their cytotoxic activities

Kiệm, Phan Văn; Dung, Dương Thị; Yến, Phạm Hải; Nhiệm, Nguyễn Xuân; Quang, Trần Hồng; Tài, Bùi Hữu; Minh, Châu Văn

doi:10.1016/j.phytol.2018.06.003

Cited by 15 publications

(10 citation statements)

References 12 publications

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“…Diverse isomalabaricane-type nor -terpenoids, containing less than 30 carbon atoms in their skeleton systems, have been found together with isomalabaricanes several times [ 10 , 11 , 12 ]. Their presence could be explained either by oxidative degradation of C 30 metabolites or by precursor role of nor -terpenoids in the biosynthesis of these compounds [ 12 , 13 ].…”

Section: Introductionmentioning

confidence: 99%

New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge

et al. 2021

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In continuation of our studies on a Vietnamese collection of a Stelletta sp., sponge we have isolated two new isomalabaricane triterpenoids, stellettins Q and R (1 and 2), and four new isomalabaricane-derived nor-terpenoids, stellettins S-V 3–6, along with previously known globostelletin N. Among them, compound 3 contains an acetylenic fragment, unprecedented in the isomalabaricane family and extremely rare in other marine sponge terpenoids. The structures and absolute configurations of all new compounds were established by extensive NMR, MS, and ECD analyses together with quantum-chemical modeling. Additionally, according to obtained new data we report the correction in stereochemistry of two asymmetric centers in the structures of two known isomalabaricanes, 15R,23S for globostelletin M and 15S,23R for globostelletin N.

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Section: Introductionmentioning

confidence: 99%

New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge

et al. 2021

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“…Although they do not clearly transfer these requirements to marine organisms, authors must consider that it applies to sponges as well. However, recent sponge NP studies in Phytochemistry Letters have not had their specimens identified by a sponge taxonomist and more importantly have not deposited their vouchers in a museum [ 62 , 78 , 79 ]. Journal of Natural Products has detailed guidelines to report the species identification; if the specimen is not identified to the species level, a description is required; the identifier should be an expert in the organisms studied, but they do not require the publication of the name of the identifier; the voucher should be deposited in a “ herbarium ” (but do not mention museums for animal material); the GPS coordinates are only recommended.…”

Section: Resultsmentioning

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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“…Next, a steroid 5α,6α-epoxy-24ethylcholesta-8 en-3β,7α-diol (27) was the double bond isomer (at C-7/C-8) of 26, along with four other steroid compounds 5α,8α-epidioxy-24Rethylcholest-6 -en-3β-ol (28), 24-norcholesta-5,22dien-3β-ol (29), 24-methylenecholest-5-en-3β-ol (30), and compound 13 were found from Tethya aurantium. [16] C-5/C-6 Epidemic epoxy steroids were also found from Ircinia echinata including melithasterol A (31), 5α,6α-epoxycholest-8(14)-ene-3β,7α-diol (32), and topsentisterol B5 (33). [17,18] These compounds exhibited significant cytotoxic effects, with IC50 values from 4.53 to 23.99 µg/mL on HepG2, HL-60, KB, LNCaP, LU-1, and MCF-7 cells.…”

Section: Steroidsmentioning

confidence: 99%

“…Conducting the study of the chemical composition and biological activity of marine species Rhabdastrella providentiae, we found the presence of triterpene compounds 75-90. [33][34][35][36][37] In particular, the chemical structures of these received compounds are formed on the basis of isomalabaricane triterpene, a rare tricyclic triterpene in nature. Therefore, the triterpene isomalabaricane compounds are considered to be chemical markers that can be used in the identification and evaluation of the quality of the species of Rhabdastrella.…”

Section: Triterpenesmentioning

confidence: 99%

The chemical constituents and biological activity of some sponges in Northern Vietnam: A review

Kiệm

Minh

Nhiệm

et al. 2019

Vietnam Journal of Chemistry

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Chemical composition and biological activity of sponges have been studied by the authors since 2006. So far, the authors have studied about 30 species of sponges, mainly collected cross in the sea of Northern Vietnam. Over 250 compounds have been isolated and elucidated their chemical structures. Among them, there are more than 50 compounds with new chemical structures. In addition to NMR and HRMS spectra, many compounds with an unequal chemical structure are also determined by Circular Dichroism spectrometry. Some isolated compounds exhibited outstanding potential for cancer cytotoxicity and anti-inflammatory effects. Keywords. Sponge chemical constituent, Porifera, Vietnam marine natural product. composition and in reserves. there are seabirds. However, researches on chemistry and compounds Vietnam Journal of Chemistry Phan Van Kiem et al.

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New isomalabaricane analogues from the sponge Rhabdastrella providentiae and their cytotoxic activities

Cited by 15 publications

References 12 publications

New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge

New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge

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

The chemical constituents and biological activity of some sponges in Northern Vietnam: A review

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