New Cembranoids from the Okinawan Soft Coral <i>Sinularia mayi</i>

Kusumi, Takenori; Yamada, Kengo; Ishitsuka, Midori O.; Fujita, Yoshiji; Kakisawa, Hiroshi

doi:10.1246/cl.1990.1315

Cited by 20 publications

(30 citation statements)

References 8 publications

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“…Due to the close similarity of the 1 H and 13 C NMR data (Supporting Information File 1, Table S3) compounds 8 and 9 were supposed to be stereoisomers. NMR spectral data of compound 8 were identical with those of (+)-isosarcophine ([α] D 20 +235.3) reported by Kusumi et al [32], so 8 is established as (+)-isosarcophine. The configuration at C-2 for 8 and 9 was established with the help of CD experiments (Supporting Information File 1, Figures S22 and S27).…”

Section: Resultssupporting

confidence: 77%

“…Additionally, during the purification of the isosarcophytoxides 10 and 11 peaks most probably attributable to the isosarcophines 8 and 9 appeared in the chromatograms, demonstrating the oxidation of the isosarcophytoxides to the isosarcophines. Reports on such conversions are found in the literature, e.g., Kusumi et al described the isolation of isosarcophine 8 from Sinularia mayi and chemical conversion of the isosarcophytoxide 10 into 8 by exposing the DCM solution of 10 to light, supporting our assumption that the isosarcophines 8 and 9 are artifacts [32]. …”

Section: Discussionsupporting

confidence: 74%

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Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

Bogdanov¹,

Hertzer²,

Kehraus³

et al. 2017

Beilstein J. Org. Chem.

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Phyllodesmium longicirrum is the largest aeolidoidean species known to date, and extremely rich in terpenoid chemistry. Herein we report the isolation of a total of 19 secondary metabolites from a single specimen of this species, i.e., steroids 1–4, cembranoid diterpenes 5–13, complex biscembranoids 14 and 15, and the chatancin-type diterpenes 16–19. These compounds resemble those from soft corals of the genus Sarcophyton, of which to date, however, only S. trocheliophorum is described as a food source for P. longicirrum. Fish feeding deterrent activity was determined using the tropical puffer fish Canthigaster solandri, and showed activity for (2S)-isosarcophytoxide (10), cembranoid bisepoxide 12 and 4-oxochatancin (16). Determining the metabolome of P. longicirrum and its bioactivity, makes it evident that this seemingly vulnerable soft bodied animal is well protected from fish by its chemical arsenal.

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Section: Resultssupporting

confidence: 77%

Section: Discussionsupporting

confidence: 74%

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

Bogdanov¹,

Hertzer²,

Kehraus³

et al. 2017

Beilstein J. Org. Chem.

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“…The known compounds, (2 S *,11 R *,12 R *)-isosarcophytoxide ( 6 ) [11], (+)-isosarcophine ( 7 ) [12], and 8-hydroxyisosarcophytoxide-6-ene ( 8 ) [12], were identified by comparison of their NMR and MS data with those in the literature.…”

Section: Resultsmentioning

confidence: 99%

New Cembrane-Type Diterpenoids from the South China Sea Soft Coral Sarcophyton ehrenbergi

2016

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Chemical investigation on the soft coral Sarcophyton ehrenbergi collected from the Xisha Islands of the South China Sea have led to the isolation of eight cembranoids including five new ones, sarcophytonoxides A-E (1-5). The structures of new cembranoids (1-5) were determined by spectroscopic analysis and comparison of the NMR data with those of related analogues. The cytotoxicities of compounds 1-8 against human ovarian cancer cell line A2780 were also evaluated.

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“…The method was applied to two cembranolides 20 and 21, which were obtained from an Okinawan soft coral Sinularia flexibilis as cytotoxic components. 12 The Á values observed for 20 are assigned to 20b. Although positive and negative values appear in groups, they are indifferent to the position of the MTPA group.…”

Section: Fate Of Thementioning

confidence: 99%

The Modified Mosher’s Method and the Sulfoximine Method

Kusumi¹,

Ooi²,

Ohkubo³

et al. 2006

Bulletin of the Chemical Society of Japan

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This article describes the application of the modified Mosher’s method to a variety of natural products possessing a secondary alcohol for determining their absolute configuration. The method is generally applicable to secondary alcohols with a few exceptions where the hydroxy group is seriously hindered by neighboring substituents. Countermeasures to solve the problems are also described. Recent findings that the modified Mosher’s method can be used in solvents other than deutero-chloroform are included. Development and application of the sulfoximine method for the determination of the absolute configuration of chiral sulfoxides are also described.

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New Cembranoids from the Okinawan Soft Coral Sinularia mayi

Cited by 20 publications

References 8 publications

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

New Cembrane-Type Diterpenoids from the South China Sea Soft Coral Sarcophyton ehrenbergi

The Modified Mosher’s Method and the Sulfoximine Method

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