The Naturally Occurring Lignans

Hearon, W. M.; MacGregor, Warren S.

doi:10.1021/cr50005a003

Cited by 106 publications

(40 citation statements)

References 132 publications

(301 reference statements)

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“…In an extensive review by Hearon and MacGregor [3] the different skeletal types were consistently numbered although there was no correlation between them. Freudenberg and Weinges [4] proposed in 1961 that the C 6 C 3 unit be numbered from 1 to 9 and the second unit from 1' to 9' to provide a consistent numbering system.…”

Section: Lg-01 Previous Proposalsmentioning

confidence: 99%

Nomenclature of Lignans and Neolignans (IUPAC Recommendations 2000)

Moss

2000

Pure and Applied Chemistry

263

186

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Lignans and neolignans are a large group of natural products characterized by the coupling of two C6C3 units. For nomenclature purposes the C6C3 unit is treated as propylbenzene and numbered from 1 to 6 in the ring, starting from the propyl group, and with the propyl group numbered from 7 to 9, starting from the benzene ring. With the second C6C3 unit the numbers are primed. When the two C6C3 units are linked by a bond between positions 8 and 8' the compound is referred to and named as a lignan. In the absence of the C-8 to C-8' bond, and where the two C6C3 units are linked by a carbon–carbon bond it is referred to and named as a neolignan. The linkage with neolignans may include C-8 or C-8'. Where there are no direct carbon–carbon bonds between the C6C3 units and they are linked by an ether oxygen atom the compound is named as an oxyneolignan. The nomenclature provides for the naming of additional rings and other modifications following standard organic nomenclature procedures for naming natural products. Provision is included to name the higher homologues. The sesquineolignans have three C6C3 units, and dineolignans have four C6C3 units.

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Section: Lg-01 Previous Proposalsmentioning

confidence: 99%

Nomenclature of Lignans and Neolignans (IUPAC Recommendations 2000)

Moss

2000

Pure and Applied Chemistry

263

186

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“…Sesame oil, Ϸ50% of seed weight, contains large amounts of natural antioxidants (1,2). The potent antioxidant properties of sesame seed extract mainly are attributable to the presence of lignans (3).…”

mentioning

confidence: 99%

“…(ϩ)-Sesamin, first isolated in 1890, is a major furofuran lignan in sesame seeds and is distinguished by two characteristic methylenedioxy bridges (2) (Fig. 1A).…”

mentioning

confidence: 99%

Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+)-sesamin

Ono¹,

Nakai²,

Fukui³

et al. 2006

Proc. Natl. Acad. Sci. U.S.A.

144

165

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“…The title compound has Related literature. Description oflignanes (Haworth, 1936); synthesis of (+), (-) and (+__) forms of pinoresinol dimethyl ether (Erdtman, 1936); reaction with bromine to yield dibromo derivatives (Erdtman, 1935); characterization of lignanes having a 2, 6-diaryl-cis-3,7-dioxabicyclo[3.3.0]octane structure (Adjangba, 1963;Hearon & MacGregor, 1955); unitcell and space-group determination of dibromo and diiodo derivatives of pinoresinol dimethyl ether, establishing twofold molecular symmetry (Wang Lund, 1960); crystal-structure determination of the lignane (-)-syringaresinol (Bryan & Fallon, 1976), crystal-structure determination of the lignane ( -)-3,6-bis(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diol (Ghisalberti, Jefferies, Skelton & White, 1987).…”

Section: Structure Of the Lignane (+)-Pinoresinol Dimethyl Ethermentioning

confidence: 99%