Structures of garugamblin-I and garugamblin-II: two natural ansa bridged biaryl ethers

Nethaji, Munirathinam; Pattabhi, Vasantha; Krishnamurthy, H. G.; Talukdar, Apurba

doi:10.1107/s0108270189006578

Cited by 4 publications

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“…A series of cyclic diarylheptanoids with a double bond in a heptyl skeleton were isolated such as 29a (garugamblin-1) and 31 (garugamblin-2) from Garuga gamblei [122,123], garugamblin-3 from Alnus japonica [124], and 29b (garuganin I) [125,126], 30a (garuganin III) [127], 30b (garuganin IV), 32 (garuganin VI) [17], and related garugamblins such as 29c and 30c [18] from Garuga pinata . Although the structures of garugamblin-1 ( 29a ), garugamblin-2 ( 31 ) [123] and garuganin I ( 29b ) [125] were confirmed by X-ray structure analysis, the originally proposed structures of garuganin III ( 30a ), garuganin IV ( 30b ), and 1,9′-didesmethylgaruganin III ( 30c ) were revised later through total synthesis to be 33 , 29a , and 30d (garuganin VII), respectively [128,129].…”

Section: Isolation Structural Features and Biological Propertiesmentioning

confidence: 99%

Recent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis

Jahng

Park

2018

Molecules

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Diarylheptanoids are a family of plant secondary metabolites with a 7 carbon skeleton possessing two phenyl rings at the 1- and 7-positions. They can be subdivided into acyclic and cyclic diarylheptanoids where the latter are further divided into meta,meta-bridged biphenyls ([7.0]metacyclophanes) and meta,para-bridged diphenyl ether heptanoids (oxa[7.1]metapara-cyclophanes). Since the isolation of curcumin from the rhizomes of turmeric (Curcuma longa) in 1815 which was named curcumin, a variety of diarylheptanoids have been isolated from a number of plant families such as Aceraceae, Actinidiaceae, Betulaceae, Burseraceae, Casuarinaceae, Juglandaceae, Leguminosae, Myricaceae, and Zingiberaceae. Earlier studies on these diarylheptanoids have been summarized on several occasions, of which the main themes only focus on isolation, structure elucidation, and the biological properties of linear types. Only a few have covered cyclic diarylheptanoids and their chemical synthesis has been covered lastly by Zhu et al. in 2000. The present paper has, therefore, covered recent progress in cyclic diarylheptanoids focusing on the isolation, structural and biological features, and chemical synthesis.

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