7-Epidenticulatolide, a New Cembranolide with a Cyclic Peroxide Function from the Soft Coral <i>Lobophytum denticulatum</i>

Uchio, Yasuto; Eguchi, Shizuko; Fukazawa, Yoshimasa; Kodama, Masashi

doi:10.1246/bcsj.65.1182

Cited by 12 publications

(10 citation statements)

References 7 publications

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“…The search for other biologically active compounds of soft corals has led to the isolation of a highly oxidized cembranolide: 7-epidenticulatolide (91) (Figure 20), which was obtained as a minor metabolite of Lobophytum denticulatum [90]. The structure was deduced spectroscopically, and compound 91 is a stereoisomer of 89, showing only differences regarding the C7 configuration.…”

Section: Endoperoxide Diterpenesmentioning

confidence: 99%

Marine Terpenic Endoperoxides

et al. 2021

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Organic extracts of marine invertebrates, mainly sponges, from seas all over the world are well known for their high in vitro anticancer and antibiotic activities which make them promising sources of compounds with potential use as pharmaceutical leads. Most of the structures discovered so far have a peculiar structural feature in common: a 1,2-dioxane ring. This is a highly reactive heterocycle that can be considered as an endoperoxide function. Together with other structural features, this group could be responsible for the strong biological activities of the substances present in the extracts. Numerous research programs have focused on their structural elucidation and total synthesis since the seventies. As a consequence, the number of established chiral centres and the similarity between different naturally occurring substances is increasingly higher. Most of these compounds have a terpenoid nature, mainly diterpene and sesterterpene, with several peculiar structural features, such as the loss of one carbon atom. Although there are many reviews dealing with the occurrence of marine peroxides, their activities, or potential pharmaceutical uses, no one has focused on those having a terpene origin and the endoperoxide function. We present here a comprehensive review of these compounds paying special attention to their structural features and their biological activity.

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Section: Endoperoxide Diterpenesmentioning

confidence: 99%

Marine Terpenic Endoperoxides

et al. 2021

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“…The structure of sagittolactone (191), obtained from the rhizomes of Liguluria sugit tu (Compositae), has been est a b l i ~h e d ~~~ by X-ray crystallography. Further diterpenes with the valparane skeleton, e.g.…”

Section: ) (From Trichoderma H ~R Z I a N U M ) ~~~mentioning

confidence: 99%

Diterpenoids

Hanson¹

1994

Nat. Prod. Rep.

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“…Further investigation of this genus revealed more than 250 compounds categorized into cembrane-type diterpenoids [2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58], other types of diterpenoids [59,60,61,62,63,64,65], lipids […”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory Cembranoids from the Soft Coral Lobophytum crassum

et al. 2017

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Cembrane-type diterpenoids are among the most frequently encountered natural products from the soft corals of the genus Lobophytum. In the course of our investigation to identify anti-inflammatory constituents from a wild-type soft coral Lobophytum crassum, two new cembranoids, lobophyolide A (1) and B (2), along with five known compounds (3–7), were isolated. The structures of these natural products were identified using NMR and MS spectroscopic analyses. Compound 1 was found to possess the first identified α-epoxylactone group among all cembrane-type diterpenoids. The in vitro anti-inflammatory effect of compounds 1–5 was evaluated. The results showed that compounds 1–5 not only reduced IL-12 release, but also attenuated NO production in LPS-activated dendritic cells. Our data indicated that the isolated series of cembrane-type diterpenoids demonstrated interesting structural features and anti-inflammatory activity which could be further developed into therapeutic entities.

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7-Epidenticulatolide, a New Cembranolide with a Cyclic Peroxide Function from the Soft Coral Lobophytum denticulatum

Abstract: A new cembranolide diterpene, 7-epidenticulatolide, was isolated from a soft coral, Lobophytum denticulatum. The structute was deduced spectroscopically and determined by X-ray crystallography.

Cited by 12 publications

References 7 publications

Marine Terpenic Endoperoxides

Marine Terpenic Endoperoxides

Diterpenoids

Anti-Inflammatory Cembranoids from the Soft Coral Lobophytum crassum

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