Cytotoxic Isomalabaricane Derivatives and a Monocyclic Triterpene Glycoside from the Sponge <i>Rhabdastrella globostellata</i>

Hirashima, Miyabi; Tsuda, Kazuomi; Hamada, Toshiyuki; Okamura, Hiroaki; Furukawa, Tatsuhiko; Akiyama, Shin-ichi; Tajitsu, Yusuke; Ikeda, Ryuji; Komatsu, Masaharu; Doe, Matsumi; Morimoto, Yoshiki; Shiro, Motoo; Soest, R.W.M. van; Takemura, Kentaro; Iwagawa, Tetsuo

doi:10.1021/np100302a

Cited by 34 publications

(27 citation statements)

References 22 publications

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“…The first glycosylated isomalabarican triterpenoid, stelliferin riboside ( 74 ) with cytotoxic properties was found in unidentified species of the genus Geodia collected off Fiji Islands [44]. Recently, a new monocyclic triterpene xylopyranoside, rhabdastoside A ( 75 ), containing a skeleton related to isomalabaricanes system, was isolated along with several new isomalabaricane derivatives from the methanol extract of the sponge Rhabdastrella globostellata (the family Ancorinidae) (Chart 10) [45]. Compound 74 stabilizes DNA polymerase β binding to DNA inducing 29% binding at the concentration 28 μg/mL [46].…”

Section: Other Triterpene Glycosides From Spongesmentioning

confidence: 99%

Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities and Biological Roles

et al. 2012

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Section: Other Triterpene Glycosides From Spongesmentioning

confidence: 99%

Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities and Biological Roles

et al. 2012

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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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“…Three of them were isolated as their corresponding methyl esters. The isolated compounds possessing a cyclopentane side chain have exhibited weak activity against leukemia HL-60 cells, while compounds with a 2-substituted-propanoate side chain were inactive at growth inhibitory concentration of 100.0 µM [ 144 ].…”

Section: Porifera Involved In the Biosynthesis Of Cytotoxic Metabomentioning

confidence: 99%

Cytotoxic Compounds Derived from Marine Sponges. A Review (2010–2012)

et al. 2017

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This extensive review covers research published between 2010 and 2012 regarding new compounds derived from marine sponges, including 62 species from 60 genera belonging to 33 families and 13 orders of the Demospongia class (Porifera). The emphasis is on the cytotoxic activity that bioactive metabolites from sponges may have on cancer cell lines. At least 197 novel chemical structures from 337 compounds isolated have been found to support this work. Details on the source and taxonomy of the sponges, their geographical occurrence, and a range of chemical structures are presented. The compounds discovered from the reviewed marine sponges fall into mainly four chemical classes: terpenoids (41.9%), alkaloids (26.2%), macrolides (8.9%) and peptides (6.3%) which, along with polyketides, sterols, and others show a range of biological activities. The key sponge orders studied in the reviewed research were Dictyoceratida, Haplosclerida, Tetractinellida, Poecilosclerida, and Agelasida. Petrosia, Haliclona (Haplosclerida), Rhabdastrella (Tetractinellida), Coscinoderma and Hyppospongia (Dictyioceratida), were found to be the most promising genera because of their capacity for producing new bioactive compounds. Several of the new compounds and their synthetic analogues have shown in vitro cytotoxic and pro-apoptotic activities against various tumor/cancer cell lines, and some of them will undergo further in vivo evaluation.

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Cytotoxic Isomalabaricane Derivatives and a Monocyclic Triterpene Glycoside from the Sponge Rhabdastrella globostellata

Cited by 34 publications

References 22 publications

Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities and Biological Roles

Glycosides from Marine Sponges (Porifera, Demospongiae): Structures, Taxonomical Distribution, Biological Activities and Biological Roles

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

Cytotoxic Compounds Derived from Marine Sponges. A Review (2010–2012)

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