Aplysiasecosterols B and C: two new 9,11-secosteroids with a cis -fused 1,4-quinone structure from the sea hare Aplysia kurodai

Kita, Masakazu; Kawamura, Atsushi; Kigoshi, Hideo

doi:10.1016/j.tetlet.2016.01.028

Cited by 16 publications

(11 citation statements)

References 17 publications

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“…These steroids are closely related to aplykurodin B found in the Pacific species A. kurodai [200]. In addition, two secosterols have been found in the sea hare A. kurodai [277]. Mucus secretions in both Atlantic and Mediterranean specimens of A. punctata present epidioxy sterols, as those of A. depilans found in its digestive gland [195].…”

Section: Steroidsmentioning

confidence: 61%

Terpenoids in Marine Heterobranch Molluscs

Ávila

2020

Marine Drugs

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Heterobranch molluscs are rich in natural products. As other marine organisms, these gastropods are still quite unexplored, but they provide a stunning arsenal of compounds with interesting activities. Among their natural products, terpenoids are particularly abundant and diverse, including monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids, and steroids. This review evaluates the different kinds of terpenoids found in heterobranchs and reports on their bioactivity. It includes more than 330 metabolites isolated from ca. 70 species of heterobranchs. The monoterpenoids reported may be linear or monocyclic, while sesquiterpenoids may include linear, monocyclic, bicyclic, or tricyclic molecules. Diterpenoids in heterobranchs may include linear, monocyclic, bicyclic, tricyclic, or tetracyclic compounds. Sesterterpenoids, instead, are linear, bicyclic, or tetracyclic. Triterpenoids, tetraterpenoids, and steroids are not as abundant as the previously mentioned types. Within heterobranch molluscs, no terpenoids have been described in this period in tylodinoideans, cephalaspideans, or pteropods, and most terpenoids have been found in nudibranchs, anaspideans, and sacoglossans, with very few compounds in pleurobranchoideans and pulmonates. Monoterpenoids are present mostly in anaspidea, and less abundant in sacoglossa. Nudibranchs are especially rich in sesquiterpenes, which are also present in anaspidea, and in less numbers in sacoglossa and pulmonata. Diterpenoids are also very abundant in nudibranchs, present also in anaspidea, and scarce in pleurobranchoidea, sacoglossa, and pulmonata. Sesterterpenoids are only found in nudibranchia, while triterpenoids, carotenoids, and steroids are only reported for nudibranchia, pleurobranchoidea, and anaspidea. Many of these compounds are obtained from their diet, while others are biotransformed, or de novo biosynthesized by the molluscs. Overall, a huge variety of structures is found, indicating that chemodiversity correlates to the amazing biodiversity of this fascinating group of molluscs.

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Section: Steroidsmentioning

confidence: 61%

Terpenoids in Marine Heterobranch Molluscs

Ávila

2020

Marine Drugs

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“…splendidus and G. daphne, 675,676 diterpenes 1239-1242, including one 1239 which was identied as being a potent sh feeding deterrent, from the aeolidoidean Phyllodesmium longicirrum, 677 and two new secosterols 1243 and 1244 from the sea hare Aplysia kurodai. 678 Of note were the structure elucidations of the Goniobranchus metabolites, many of which were isolated in submilligram quantities. In a beautiful exposition of the utility of total synthesis, the putative linear contiguous polyketide precursor of the mollusc metabolite dolabriferol has been shown to undergo regioselective retro-Claisen fragmentation to form the natural product under mild conditions.…”

Section: Molluscsmentioning

confidence: 99%

Marine natural products

et al. 2018

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Covering: 2016. Previous review: Nat. Prod. Rep., 2017, 34, 235-294This review covers the literature published in 2016 for marine natural products (MNPs), with 757 citations (643 for the period January to December 2016) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1277 in 432 papers for 2016), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included.

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“…This 9,11-secosteroid possesses an unprecedented tricyclic γ-diketone core attached by a densely substituted cyclopentane moiety. The same team also discovered two congeners of 1 , aplysiasecosterols B and C ( 2 and 3 ), the former of which was proposed as the biogenetic precursor of 1 . In 2016, Sung, Sheu, Wu, and co-workers reported the isolation of pinnigorgiols A, B, D, and E ( 4 – 7 ) from the gorgonian Pinnigorgia sp., which share an aplysiasecosterol A type scaffold and vary slightly in their side chains .…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Aplysiasecosterol A

Zhang

Guo

et al. 2018

J. Am. Chem. Soc.

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Aplysiasecosterol A (1) is a structurally unusual 9,11-secosteroid isolated from the sea hare Aplysia kurodai. We have accomplished the first and asymmetric total synthesis of 1 in a convergent fashion. The left-hand segment bearing three adjacent stereocenters was constructed through desymmetrizing reduction, ketalization, and radical cyclization. A strategy of asymmetric 2-bromoallylation followed by spontaneous desymmetrizing lactolization enabled a more expeditious access to this segment. The right-hand segment was prepared through two different approaches: one featuring Myers alkylation and Suzuki-Miyaura coupling and the other relying upon Aggarwal lithiation-borylation and Zweifel-Evans olefination. The two fragments were coupled by a Reformatsky type reaction. The three consecutive stereocenters embedded in the central domain of 1 were generated by an iron-mediated, hydrogen atom transfer based radical cyclization reaction.

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Aplysiasecosterols B and C: two new 9,11-secosteroids with a cis -fused 1,4-quinone structure from the sea hare Aplysia kurodai

Cited by 16 publications

References 17 publications

Terpenoids in Marine Heterobranch Molluscs

Terpenoids in Marine Heterobranch Molluscs

Marine natural products

Total Synthesis of Aplysiasecosterol A

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