Six New Polyhydroxysteroidal Glycosides, Anthenosides S1 – S6, from the Starfish <i>Anthenea sibogae</i>

Kicha, A. A.; Ha, Dinh T.; Ivanchina, Natalia V.; Malyarenko, Timofey V.; Kalinovsky, Anatoly I.; Dmitrenok, Pavel S.; Ermakova, Svetlana P.; Malyarenko, Olesya S.; Hung, Nguyen Anh; Thuy, Tran Thi Thanh; Long, Pham Quoc

doi:10.1002/cbdv.201700553

Cited by 11 publications

(16 citation statements)

References 18 publications

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“…Compound 131 contains a rare 5 α ‐cholest‐8(14)‐ene‐3 α ,7 β ,16 α ‐trihydroxysteroidal nucleus . Compounds 134 – 137 were yielded by the starfish Anthenea sibogae . They all have a 5 α ‐cholest‐8(14)‐ene‐3 α ,6 β ,7 β ,16 α ‐tetrahydroxysteroidal nucleus .…”

Section: Chemical Constituentsmentioning

confidence: 99%

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Chemical Constituents and Bioactivities of Starfishes: An Update

Xia

Miao

Xie

et al. 2020

Chemistry & Biodiversity

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Starfishes produce various structurally unique secondary metabolites with diverse biological activities. This review is an update summary of the new compounds and their bioactivities from starfish (the Asteroidea Class) with 71 references covering from January 2007 to December 2018. During this period, 216 new compounds were obtained from 36 species. The chemical constituents are mostly steroids, steroidal glycosides, and gangliosides. These components have been found to possess various bioactivities, including anticancer, anti-inflammation, etc.

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Section: Chemical Constituentsmentioning

confidence: 99%

“…Compounds 134 – 137 were yielded by the starfish Anthenea sibogae . They all have a 5 α ‐cholest‐8(14)‐ene‐3 α ,6 β ,7 β ,16 α ‐tetrahydroxysteroidal nucleus . Compound 139 has a Δ 22 ‐cholestane side chain of the steroidal aglycons, which was new for starfish steroidal compounds .…”

Section: Chemical Constituentsmentioning

confidence: 99%

Chemical Constituents and Bioactivities of Starfishes: An Update

Xia

Miao

Xie

et al. 2020

Chemistry & Biodiversity

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“…Another study has confirmed the cytotoxic activity of six new polyhydroxylsteroidal glycosides and two previously known glycosides, which were isolated from starfish Anthenea sibogae. The mixture of two known glycosides has been shown to exert slightly inhibitory effects on cell proliferation in human breast cancer and to decrease colony size in vitro (75). Plancitoxin I derived from the venom of the crown-ofthorns starfish Acanthaster planci, has been reported to exert strong cytotoxic effects in human malignant melanoma cells (76,77).…”

Section: The Potential Anticancer Activity Of Starfish and Sea Urchinmentioning

confidence: 99%

Therapeutic Application of Diverse Marine-derived Natural Products in Cancer Therapy

Yun

Kim

2019

Anticancer Res

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Natural products (NPs) are useful sources of bioactive compounds and play important roles in the development and discovery of new drugs for diverse human diseases. Most natural products originate from terrestrial species, but diverse marine organisms are another source of new agents for cancer therapy. Natural products derived from marine organisms show diverse pharmacological activities via bioactive secondary metabolites. They regulate biological activities, such as cell proliferation, cell viability, induction of ROS production, ER stress, and apoptosis via modulation of cellular mechanisms in many cancers. Many natural products isolated from marine species require further study to elucidate the efficacy of their biological activity and anticancer effects. In this review, we summarize the biological properties and anticancer effects of diverse natural products extracted from marine organisms and their roles in tumor therapy. Cancer is one of the leading causes of death and an economic burden worldwide (1). Cancer involves an abnormal proliferation of cells and tissues, and is affected by various risk factors such as age, diet, genetics, and environmental factors (2, 3). It is also caused by the mutation of several cancer-related genes called tumor suppressors and oncogenes (4). Cancer also presents the ability of metastasis and recurrence, which are difficult to treat (5). Although conventional anticancer therapy includes both chemotherapy to induce apoptosis of target cancer cells and surgical therapy to remove tumors, these methods are limited by issues of therapeutic efficacy, safety, and side effects. Thus, it is necessary to develop novel strategies for cancer therapy, and natural products (NPs) are a promising source for novel drug development because they show diverse biological activities and anticancer effects via inhibition of tumor growth by interacting with several signaling pathways (6, 7). NPs have been a useful source of bioactive compounds and play an important role in the discovery and development of drugs. Most NPs, originated from terrestrial microbes, fungi, and plants, have been discovered to possess many pharmacologically active factors and used to treat several human diseases. Some of these are utilized as clinically valuable drugs for anticancer therapy (8-10). However, marine organisms have recently attracted substantial attention because 70% of the earth is covered by water, representing 95% of biodiversity (11-13). NPs derived from marine organisms have been researched for novel bioactive secondary metabolites due to their diverse pharmacological activities. Marine environments are estimated to harbor more than one million species and one billion different types of marine microbes (14). Today, around 28,000 new compounds isolated from marine species, such as algae, seaweed, sponges, and starfish, have been reported, and this species diversity provides a diverse array of secondary metabolic products (15, 16). In this review, we present NPs derived from marine environments, and summari...

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“…Elyakov Pacific Institute of Bioorganic Chemistry which celebrated its 55th anniversary in 2019. Continuing our research on biologically active steroid metabolites from the starfish species inhabiting the Vietnamese sea waters [11][12][13][14][15], herein, we describe the results of our investigation of steroid constituents from the methanolic extract of the starfish Anthenoides laevigatus Liao & A.M. Clark, 1989 (order Valvatida, family Goniasteridae), collected off the coastal waters of the Qui Nhon Province, Vietnam. We have isolated and structurally studied four new polyhydroxylated steroids 1−4, along with two previously known related steroids 5 and 6.…”

Section: Introductionmentioning

confidence: 99%

Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

Kicha

Malyarenko

et al. 2020

Molecules

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Four new polyhydroxylated steroids 1–4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and HRESIMS techniques. Heptaol 1 and hexaol 2 contain the common 5α-cholestane skeleton, while hexaol 3 and heptaol 4 have the rare among starfish steroid compounds 5β-cholestane skeleton. Compounds 1, 5, and 6 do not show cytotoxic effects against normal JB6 Cl41 and cancer HT-29 and MDA-MB-231 cells, however they inhibit cell proliferation and colony formation of cancer HT-29 and MDA-MB-231 cells.

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Six New Polyhydroxysteroidal Glycosides, Anthenosides S1 – S6, from the Starfish Anthenea sibogae

Cited by 11 publications

References 18 publications

Chemical Constituents and Bioactivities of Starfishes: An Update

Chemical Constituents and Bioactivities of Starfishes: An Update

Therapeutic Application of Diverse Marine-derived Natural Products in Cancer Therapy

Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

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