Chemical and Pharmaceutical Bulletin
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2018 Volume 66 Issue 7 Pages 771-772

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Vol./Page: Chem. Pharm. Bull. 62, 937–941 (2014)

Title: A Lanostane Triterpenoid and Three Cholestane Sterols from Tilia kiusiana

Authors: Marie Shimada, Masaaki Ozawa, Kojiro Iwamoto, Yoshiyasu Fukuyama, Akio Kishida, and Ayumi Ohsaki

Authors Comments:

Structures of compounds 3 and 4 should be revised, because the functional groups were found to be exchanged between C-3 and C-6. Thus, compound 3 was known compound, 3β-hydroxy-cholest-7-en-6-one, and trivial name kiusianin C was withdrawn. We thank Assoc. Prof. Dr. Wolfgang Robien (University of Vienna, Austria) for the private letter regarding the revision of the structures 3 and 4 using the calculated 13C-NMR data (http://nmrpredict.orc.univie.ac.at/c13robot/robot.php).

Ayumi Ohsaki

Department of Chemistry, College of Humanities and Sciences, Nihon University, Japan

April 8, 2018

Vol.PageLineErrorCorrection
62937SummaryKiusianins A–D (14) were isolated from the leaves of a Japanese endemic plant, Tilia kiusiana, together with 14 known compounds. The structures of a new lanostane-type triterpenoid 1 and three new cholestane-type sterols 24 were elucidated by spectroscopic methods,Kiusianins A, B and D (1, 2, 4) were isolated from the leaves of a Japanese endemic plant, Tilia kiusiana, together with 15 known compounds. The structures of a new lanostane-type triterpenoid 1 and two new cholestane-type sterols 2 and 4 were elucidated by spectroscopic methods,
left 12isolation of four new compounds 14 named kiusianins A–Disolation of three new compounds 1, 2, and 4 named kiusianins A, B, and D
left 15kiusianins A–D (14)kiusianins A, B, and D (1, 2, 4)
left 24three new sterols 24, together with 3β-hydroxy-two new sterols 2 and 4, together with 3β-hydroxy-5α-cholest-7-en-6-one (3)16), 3β-hydroxy-
938Table 1
Table 2
right↑2cholest-7-en-3-onecholest-7-en-6-one
right↑1The position of the hydroxyl group was unambiguously assigned to C-6 on the basis of HMBC correlation of H-5 (δH 2.25) to C-6c 70.8) and 1H–1H COSY cross-peak of H-6/H-7.The position of the hydroxyl group was unambiguously assigned to C-3 on the basis of HMBC correlation of H-5 (δH 2.25) to C-3c 70.8).
939left 4H-5/H-9 and H-6H-5/H-9 and H-3
left 86β-hydroxy-cholest-7-en-3-one and named kiusianin C.3β-hydroxy-cholest-7-en-6-one (3).
Fig. 1
Fig. 2
Key 1H–1H COSY (Bold) and HMBC (Arrow) Correlations for Kiusianins A–C (13)Key 1H–1H COSY (Bold) and HMBC (Arrow) Correlations for Compounds (13)
Fig. 3Key NOESY Correlations for Kiusianins A–C (13)Key NOESY Correlations for Kiusianins A and B (1, 2)
Compound 3 was deleted.
940left 156β-hydroxy-cholest-7,20-diene-3-one3β-hydroxy-cholest-7,20-diene-6-one
left 21New compounds 24Compounds 24
941left 20kiusianin C (3, 0.50 mg)compound 3 (0.50 mg)
left↑8Kiusianin C3β-hydroxy-cholest-7-en-6-one
References16) Kulig M. J., Smith L. L., J. Org. Chem., 39, 3398–3402 (1974).
 
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