1996
DOI: 10.1248/cpb.44.1122
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Studies on the Constiuents of Viburnum Species. Part XIII. Isolation and Absolute Structures of the Neolignan Glycosides with the Enantiometric Aglycones from the Leaves of Viburnum awabuki K. KOCH.

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Cited by 87 publications
(76 citation statements)
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“…The circular dichroism (CD) spectrum showed a negative Cotton effect at 225 nm, suggesting 7′S. [9][10][11] Based on this data, the structure of clinopodic acid J was elucidated as 1.…”
Section: Resultsmentioning
confidence: 92%
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“…The circular dichroism (CD) spectrum showed a negative Cotton effect at 225 nm, suggesting 7′S. [9][10][11] Based on this data, the structure of clinopodic acid J was elucidated as 1.…”
Section: Resultsmentioning
confidence: 92%
“…The absolute stereochemistry of the dihydrobenzofuran ring of clinopodic acids K, L, and M was determined as shown from the negative Cotton effect at 223-226 nm in the CD spectrum. 9) Clinopodic acid N (5) was isolated as a colorless amorphous solid. The molecular formula of 5 was established as In the 13 C-NMR spectrum, C-1′ of unit B was observed at δ 129.2, which was shifted upfield by about 4 ppm compared with that of trans-type dihydrobenzofuran compounds such as 1-4, indicating a cis-type dihydrobenzofuran moiety.…”
Section: Resultsmentioning
confidence: 99%
“…The coupling constants of the methine signals at δ 5.54 (H-7) and δ 3.34 (H-8) were 5.81 Hz, indicating a 7,8-trans configuration. 27) In addition, a negative Cotton effect at 330 nm and a positive Cotton effect at 270 nm in the CD spectrum were similar to those of a known compound (pterolinus C, with a negative Cotton effect at 319 nm and a positive Cotton effect at 255 nm), 28) suggesting that the absolute configurations were 7S and 8S. Consequently, 21 was determined to be (…”
Section: Resultsmentioning
confidence: 70%
“…The absolute configuration at C-9 of the aglycon was assigned as R on the basis of a diagnostic chemical shift of the C-9 signal (d 76.8) in the 13 C NMR spectrum. 21 Consequently, the structure of 1 was determined to be (6S, 7E, 9R)-6,9-dihydroxy-4,7-megastigmadien-3-one-9-O-[a-L-arabinofuranosyl-(l"→6')]-b-d-glucopyranoside (Figure 1). Earlier study reported the isolation of (6S, 7E, 9R)-6, 9-dihydroxy-4, 7-megastigmadien-3-one-9-O-[a-L-arabinopyranosyl-(l→6)]-b-d-glucopyranoside from Lonicera gracilipes Var.…”
Section: Resultsmentioning
confidence: 99%