Three halogenated metabolites fromLaurencia obtusa

Ayyad, S.N.; Dawidar, A. M.; Dias, Hanwellage W.; Howie, R. Α.; Jakupovic, Jsmin; Thomson, R. H.

doi:10.1016/0031-9422(90)80183-h

Cited by 20 publications

(23 citation statements)

References 9 publications

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“…A Flack's index value close to zero gave confidence as to the choice of the absolute configurations as in 4 and, therefore, in 3. The closest structural example from X-ray diffraction analysis is (4R,3S,6S,lOS)-lObromo-4-chloro-3,11 ,I l-trimethyl-7-rnethylidenespiro[6.6]undecan-3-01 known as hurgadol [6].…”

Section: 2mentioning

confidence: 99%

Rogioldiol A, a new obtusane diterpene, and rogiolal, a degraded derivative, of the red seaweed Laurencia microcladia from II rogiolo along the coast of tuscany: A Synergism in Structural Elucidation

Guella

Pietra

Marchetti

1997

Helvetica Chimica Acta

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~~ ~The structure of rogioldiol A (( -)-l), isolated from the red seaweed Laurencia microcladia, was determined. Employing the exciton-coupling technique for rogioldiol A p-bromobenzoate (2), the absolute configuration at C(9) of (-)-1 was assigned, and, together with extensive NMR experiments, the absolute configuration at C(10) and preferred conformations of (-)-1 were determined. The absolute configuration of the hetero-substituted cyclohexane ring was deduced in analogy from the X-ray structure of 4, a derivative of the aldehyde 3, which was isolated from the same seaweed and is believed to be a degradation product of (-)-1.

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Section: 2mentioning

confidence: 99%

Rogioldiol A, a new obtusane diterpene, and rogiolal, a degraded derivative, of the red seaweed Laurencia microcladia from II rogiolo along the coast of tuscany: A Synergism in Structural Elucidation

Guella

Pietra

Marchetti

1997

Helvetica Chimica Acta

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“…Ingenol-3,20-dibenzoate (IDB, 57k), a non-tumor promoting ester, was identified as the potent antileukemic principle of E. esula by Kupchan in 1976 [145], fostering considerable interest in the anticancer properties of ingenol esters. The same bioactivity-directed fractionation scheme afforded phorbol 12-tiglate-13decanoate, a moderately potent tumor promoting ester, as the antileukemic principle of croton oil.…”

Section: Anticancer and Immunostimulating Activitymentioning

confidence: 99%

“…The glycolipids 1026 and 1027, floridoside (1028) and D-isofloridoside (1029) and the related metabolites 1030-1032 were isolated from various species of Laurencia, all collected from mainland China, South Korea or India [290,808,[830][831][832][833]. The iodolactone 1033 was isolated from Laurencia majuscula [809], and (Z )-2-chloropentadec-2-enal (1034) containing an unusual chloroenal functionality was obtained from Laurencia flexilis [149], and its synthesis was achieved in one step from commercial tridecanal [834], whereas the α,β-unsaturated aldehydes 1035 and 1036 have been isolated from a number of Laurencia species [61,134,145,255,812]. The latter metabolite is considered the aldol product of pentadecanal (1041), with which it was also isolated from Laurencia filiformis [89].…”

Section: Miscellaneous Metabolitesmentioning

confidence: 99%

“…A number of fatty acid derivatives (1040 and 1042-1047) have been isolated from species of Laurencia [822,843,844]. Finally, common fatty acids, such as palmitic acid, eicosanoic acid, arachidonic acid and eicosapentaenoic acid, have been registered as constituents of the genus Laurencia [145,373,809,846]. …”

Section: Miscellaneous Metabolitesmentioning

confidence: 99%

“…The absolute stereochemistry of this compound has been established 1032 -L. pedicularioides [833] 1033 -L. majuscula [809] 1034 (2Z )-Chloro-pentadec-2-enal L. flexilis [149]; Synthesis [834] 1035 (E)-2-((E)-Tridec-2-en-2-yl) heptadec-2enal L. papillosa [812] 1036 (E)-2-Tridecyl-2-heptadecanal L. filiformis [89], L. microcladia [255], L. obtusa [145] …”

Section: Steroidsmentioning

confidence: 99%

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Three halogenated metabolites fromLaurencia obtusa

Cited by 20 publications

References 9 publications

Rogioldiol A, a new obtusane diterpene, and rogiolal, a degraded derivative, of the red seaweed Laurencia microcladia from II rogiolo along the coast of tuscany: A Synergism in Structural Elucidation

Rogioldiol A, a new obtusane diterpene, and rogiolal, a degraded derivative, of the red seaweed Laurencia microcladia from II rogiolo along the coast of tuscany: A Synergism in Structural Elucidation

Progress in the Chemistry of Organic Natural Products 102

Rhodophyceae (Red Algae)

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