Halichonines A, B, and C, novel sesquiterpene alkaloids from the marine sponge Halichondria okadai Kadota

Ohno, Osamu; Chiba, Tatsuhiko; Todoroki, Seiji; Yoshimura, Hideaki; Maru, Norihito; Maekawa, Ken; Imagawa, Hiroshi; Yamada, Kaoru; Wakamiya, Atsushi; Suenaga, Kiyotake; Uemura, Daisuke

doi:10.1039/c1cc15557a

Cited by 16 publications

(16 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 325 displayed broad cytotoxicity against four cancer cell lines, including A549, SK-OV-3, SK-MEL-2, and HCT-15, with IC 50 values of 2.0, 1.9, 3.9 and 3.2 µM, respectively [76]. Noveliresane sesquiterpene alkaloids, halichonines A (327), B (328), and C (329) (Figure 8), were identified from the marine sponge Halichondria okadai Kadota, and 328 wasthen subjected to the trypan blue dye exclusion using HL60 human leukemia cells, and showed cytotoxicity (IC 50 value: 0.60 µg/mL) [77]. One γ-elemene-type sesquiterpenes, 8β(H)-elema-1,3,7(11)-trien-8,12-lactam (330) (Figure 8) was obtained from the rhizomes of Curcuma phaeocaulis [63].…”

Section: Germacrane Elemaneand Iresane Sesquiterpenoidsmentioning

confidence: 99%

Natural Nitrogenous Sesquiterpenoids and Their Bioactivity: A Review

et al. 2020

View full text Add to dashboard Cite

Nitrogenous sesquiterpenoids fromnatural sourcesare rare, so unsurprisingly neither the potentially valuable bioactivity nor thebroad structural diversity of nitrogenous sesquiterpenoids has been reviewed before. This report covers the progressduring the decade from 2010 to February 2020 on the isolation, identification, and bioactivity of 391 nitrogen-containing natural sesquiterpenes from terrestrial plant, marine organisms, and microorganisms. This complete and in-depth reviewshouldbe helpful for discovering and developing new drugs of medicinal valuerelated to natural nitrogenous sesquiterpenoids.

show abstract

Section: Germacrane Elemaneand Iresane Sesquiterpenoidsmentioning

confidence: 99%

Natural Nitrogenous Sesquiterpenoids and Their Bioactivity: A Review

et al. 2020

View full text Add to dashboard Cite

show abstract

“…The Halichondria genus consists of over 60 species and, over the years, novel and bioactive metabolites of varying structural classes and pharmacological activities have been isolated from this genus. Structural classes range from macrolides, sequiterpenes, polyethers, alkaloids and sterols with a dominance in anti-tumour activities [44][45].…”

Section: Genus: Halichondriamentioning

confidence: 99%

The Ongoing Study of the Chemistry of the Marine Inhabitants of The Ramsar Site of Port Royal, Jamaica

Gallimore

2018

JAC

View full text Add to dashboard Cite

Research efforts to examine the chemistry of marine organisms collected from the Ramsar site of Port Royal, Jamaica, has led to the isolation of a range of compounds as diverse as the species from which they were derived. Six sponges, two algal species, one ascidian and one soft coral collected from the mangrove area and the shallow coastal reefs were studied to yield compounds including steroids, aromatic compounds and terpenoids.

show abstract

“…Halichonine B was then subjected to the trypan blue dye exclusion using HL-60 human leukemia cells, and has shown cytotoxicity at IC 50 value of 0.6 µg·mL −1 . DNA ladder analysis revealed that halichonine B has induced DNA fragmentation in HL-60 cells [ 127 ].…”

Section: Porifera Involved In the Biosynthesis Of Cytotoxic Metabomentioning

confidence: 99%

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

et al. 2017

View full text Add to dashboard Cite

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.

show abstract

Halichonines A, B, and C, novel sesquiterpene alkaloids from the marine sponge Halichondria okadai Kadota

Cited by 16 publications

References 14 publications

Natural Nitrogenous Sesquiterpenoids and Their Bioactivity: A Review

Natural Nitrogenous Sesquiterpenoids and Their Bioactivity: A Review

The Ongoing Study of the Chemistry of the Marine Inhabitants of The Ramsar Site of Port Royal, Jamaica

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

Contact Info

Product

Resources

About