Three new cytotoxic sesterterpenoids, inorolide A, B, and C from the nudibranch Chromodoris inornata

Miyamoto, Tomofumi; Sakamoto, Kenichiro; Amano, Hiroko; Higuchi, Ryota; Komori, Tetsuya; Sasaki, Takuma

doi:10.1016/0040-4039(92)89038-e

Cited by 24 publications

(13 citation statements)

References 13 publications

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“…Consisting of the two families, Arminidae (seven genera) and Doridomorphidae (one genus), this superfamily has received minimal attention from natural products researchers, with only two species of the Arminidae (Armina and Dermatobranchus) being investigated to date. A series of seven briarane diterpenes, including the chlorinated example 91, was isolated from the nudibranch Armina maculata and its octocoral prey Veretillum cynomorium [318][319][320] as was a cembranoid, preverecynarmin (92), 320 highlighting that all were of dietary origin for the nudibranch. Similarly, four related diterpenoids, ophirin (93), calicophirin B (94), 13-deacetoxyl calicophirin B (95) and 13-deacetoxy-3deacetyl calicophirin B (96), were isolated from the nudibranch Dermatobranchus ornatus.…”

Section: Arminoideamentioning

confidence: 99%

The chemistry and chemical ecology of nudibranchs

Dean

Prinsep

2017

Nat. Prod. Rep.

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Covering: up to the end of February 2017Nudibranchs have attracted the attention of natural product researchers due to the potential for discovery of bioactive metabolites, in conjunction with the interesting predator-prey chemical ecological interactions that are present. This review covers the literature published on natural products isolated from nudibranchs up to February 2017 with species arranged taxonomically. Selected examples of metabolites obtained from nudibranchs across the full range of taxa are discussed, including their origins (dietary or biosynthetic) if known and biological activity.

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Section: Arminoideamentioning

confidence: 99%

The chemistry and chemical ecology of nudibranchs

Dean

Prinsep

2017

Nat. Prod. Rep.

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“…This family of tricyclic terpanes contains homologues having from 19 to at least 45 carbon atoms (Moldowan and Seifert 1983). Natural products bearing the cheilanthane skeleton are known from sponges (Manes et al 1988;Buchanan et al 2001), nudibranchs (Miyamoto et al 1992) and ferns (Khan et al 1971). However, these organisms do not contribute high mass of organic matter to sediments and they are certainly not the biological sources of the ubiquitous and abundant cheilanthanes.…”

Section: Orphan Biomarkers and Unknown Pathwaysmentioning

confidence: 99%

Building the Biomarker Tree of Life

Brocks

2005

Reviews in Mineralogy and Geochemistry

153

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the molecular fossils of plants and other non-microscopic eukaryotes. We highlight biomarker research using outstanding recent examples with a pedagogic emphasis on concepts but with no claim for completeness. More encyclopedic reviews were given by Peters et al. (2004) and Brocks and Summons (2004). For readers who desire more background in organic geochemistry, excellent introductions to the nomenclature, chemistry, and biology of lipids can be found in textbooks by Killops and Killops (2005) and Madigan and Martinko (2005). The biomarker principle The origin of biomarkers. In lakes and oceans, the organic matter from dead organisms usually is almost quantitatively (> 99.9%) recycled back into carbon dioxide and water (Hedges and Keil 1995). The biological degradation of most proteins, nucleic acids and carbohydrates proceeds rapidly as dead biomass sinks through the water column, and it continues in the surface layers of the sediments. However, a small fraction of organic matter escapes the remineralization process and accumulates. Molecules that are especially recalcitrant, such as pigments, lipids and many structural macromolecules, will become concentrated (Tegelaar et al. 1989). With the onset of reducing conditions, the remaining sedimentary organic matter is degraded further by anaerobic heterotrophic organisms such as sulfate reducers, fermenters and methanogens (Megonigal et al. 2004); the chemical structure of the remains is altered by biological and chemical processes (Hedges and Keil 1995; Hedges et al. 1997; Rullkötter 1999). These alterations are referred to collectively as diagenesis. Smaller molecular units and degradation-resistant macromolecules are cross-linked and form kerogen, an amorphous and exceedingly complex structural network of biochemical subunits (e.g., Derenne et al. 1991; de Leeuw and Largeau 1993). During the formation of kerogen, vulcanization reactions mediated by sulfur and polysulphides often play an important role in connecting smaller molecular units, such as lipids, to the macromolecular aggregate, thus protecting them against further structural alterations (Sinninghe Damsté and de Leeuw 1990). Over millions of years, and with increasing burial depth and geothermal heat, most lipids will undergo structural rearrangement via cracking and isomerization reactions. These processes create a vast range of homologues and stereo-and structural isomers. Through reduction, elimination and aromatization the biomarkers typically lose all of their functional groups. The resultant products are geologically-stable hydrocarbon skeletons. Structures 1 and 2; 3 and 4; and 5 and 6 show examples of biolipids and their diagenetic hydrocarbon products.

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“…Norfriedelin B (with a keto-lactone group) showed acetyl-cholinesterase inhibitory effects with the IC50 values of 28.7 μM. [26] The cytotoxic sesterterpenoid, inorolide A (9), was isolated from a Japanese nudibranch Chromodoris inornata (Chromodorididae), [27] and hippospongide A (10) obtained from the Xestospongia testudinaria. [28] Three steroids (11, 12 and 13) with a modified ring C were isolated from the plants Physalis minima and Solanum nigrum.…”

Section: Introductionmentioning

confidence: 99%

“…and kadsuphilactone B (28) were isolated from the Taiwanese medicinal plant Kadsura philippinensis. Compound (27) showed anticancer activity, and kadsuphilactone B (28) exhibited in vitro anti-HBV activity with IC50 values of 6 μg/mL by HBsAg enzyme immunoassay. [38,39] The sedative triterpenes (30)(31)(32) were found in leaves and roots of the Galphimia glauca.…”

Section: Introductionmentioning

confidence: 99%

Highly oxygenated isoprenoid lipids derived from terrestrial and aquatic sources: Origin, structures and biological activities

Vil

Gloriozova

Terent’ev

et al. 2019

Vietnam Journal of Chemistry

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This mini review is devoted to an interesting group of natural terpenoids called highly oxygenated isoprenoid lipids (HOIL). Their producers are microorganisms, as well as they are found in plants, fungi, animals and marine organisms. The present review consists of three parts. For all three groups of HOIL presented, the chemical structure and the calculated biological activity are given. The first is an overview of HOIL found in nature with a description of some of the pharmacological properties and activity. For the first group of terpenoids, the most characteristic activities are anti‐seborrheic, antineoplastic, and anti‐inflammatory, and they can be used as ovulation inhibitors with a certainty of 85 to 91 percent. In the second part, we present an interesting group of heterocyclic HOIL (or steroidal alkaloids) found in nature with an indication of their possible activity. For the second group of HOIL, the most characteristic activities are: hypolipemic, antifungal, and antineoplastic, and they can be used as lipid metabolism regulators with a confidence of 81 to 89 percent. And in the third group, we represent HOIL derived from marine microorganisms and invertebrates. For the third group of HOIL, the most characteristic activities are: antineoplastic and antipsoriatic and they can be used as cytochrome P450 inhibitors and hepatoprotectants with a confidence of 77 to 93 percent.

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Three new cytotoxic sesterterpenoids, inorolide A, B, and C from the nudibranch Chromodoris inornata

Cited by 24 publications

References 13 publications

The chemistry and chemical ecology of nudibranchs

The chemistry and chemical ecology of nudibranchs

Building the Biomarker Tree of Life

Highly oxygenated isoprenoid lipids derived from terrestrial and aquatic sources: Origin, structures and biological activities

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