Solandelactones A-I, lactonized cyclopropyl oxylipins isolated from the hydroid Solanderia secunda

Tetrahedron

Volumn 52, Issue 32, 1996, Pages 10583-10596

  Seo, Youngwan ^a   Cho, Ki Woong ^a   Rho, Jung Rae ^a   Shin, Jongheon ^a   Kwon, Byoung Mog ^b   Bok, Song Hae ^b   Song, Jun Im ^c  

^a Korea Research Institute of Ships and Ocean Engineering   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^c Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; FARNESYL TRANS TRANSFERASE; FATTY ACID DERIVATIVE; POLYENE; SOLANDELACTONE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BIOSYNTHESIS; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; INVERTEBRATE; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

EID: 0030570847     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00606-0     Document Type: Article

References (19)

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4. 4. Specimens of S. secunda (voucher number 91-10) are on deposit in the coelenterate collection, Natural History Museum, Ewha Womans University, Seoul, Korea, under the curatorship of J.-I. S.
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10. 10. The absolute configurations of constanolactones A and B were determined as 5R,6R,8S,9S,12S and 5R, 6S,8S,9R,12S, respectively by chemical and spectroscopic methods. The absolute stereochemistry of halichlactone was determined as 8S,9R,11R,12R,15R by total synthesis. See ref. 6 and 9.
11. 11. To confirm the configuration of the cyclopropyl ring, we also performed NOESY experiments of 5 and 10 in which the key nOe interactions between the H-6 protons and the H-8 and H-10 protons were consistently observed.
12. 1H NMR spectra of 2R and 2S dimethyl-MC-malates showed significantly differentiated chemical shifts for the H-7 and H-8 protons [2R derivative: δ 0.86 (H-7) and 1.90 (H-8); 2S derivative: δ 0.90 (H-7) and 2.00 (H-8)].
13. 13C NMR δ 75.10 (C-13), 74.29 (C-14): see ref.6.
14. 14. Compound 9 was highly unstable. All of the efforts to convert 9 to derivatives for determination of stereochemistry at C-13 and C-14 resulted in decomposition of the reactant.
15. 15. Higgs, M. D.; Mulheirn, L. J. Tetrahedron 1981, 37, 4259.
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18. 18. Gerwick, W. H. Chem. Rev. 1993, 93, 1807.
19. 19. The biogenetic origin and biosynthetic pathway of solandelactones are currently under investigation. The results will be published in due course.