Neovibsanines A and B, unprecedented diterpenes from Viburnum awabuki

Fukuyama, Yoshiyasu; Matsuda, Hiroyuki; Takeuchi, Kumiko; Kodama, Masashi; Kawazu, Kazuyoshi

doi:10.1016/s0040-4039(96)01463-3

Cited by 59 publications

(40 citation statements)

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“…Among these three subtypes, neovibsane-type diterpenes occupy a particular position in the vibsane-type natural products, owing to their unprecedented skeleton as well as intriguing biological activities. 16) We have already established the chemical conversion of vibsanin B (12) to neovibsane-skeletons, 2,3) but have not succeeded in determining conditions suitable for the provision of any intact neovibsanins. Thus, our continuing interests in chemical and biological profiles of vibsane-type diterpenes have resulted in the isolation of nine new neovibsane-type diterpenes 1-9 from a methanol extract of the leaves of Viburnum awabuki, as well as the successful interconversion of vibsanin B (12) to neovibsanins A (14) and B (15) by photochemical reaction.…”

Section: -15)mentioning

confidence: 99%

“…

Vibsane-type diterpenes can be regarded as quite rare natural products because they occur exclusively in Viburnum species such as V. awabuki [1][2][3][4][5][6][7][8][9][10][11] and V. odoratissimum.

12-15)The carbon skeletons of vibsane-type diterpenes consist of three structural subtypes, i.e., 11-and 7-membered ring compounds, and rearranged type (neovibsane-type) such as vibsanins B (12) and C (13), 1,3) and neovibsanin A (14), 2) respectively. Among these three subtypes, neovibsane-type diterpenes occupy a particular position in the vibsane-type natural products, owing to their unprecedented skeleton as well as intriguing biological activities.

…”

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confidence: 99%

“…Vibsane-type diterpenes can be regarded as quite rare natural products because they occur exclusively in Viburnum species such as V. awabuki [1][2][3][4][5][6][7][8][9][10][11] and V. odoratissimum.…”

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confidence: 99%

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Rearranged Vibsane-Type Diterpenes from Viburnum awabuki and Photochemical Reaction of Vibsanin B

Kubo

Matsuda

Yuasa

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Vibsane-type diterpenes can be regarded as quite rare natural products because they occur exclusively in Viburnum species such as V. awabuki [1][2][3][4][5][6][7][8][9][10][11] and V. odoratissimum. 12-15)The carbon skeletons of vibsane-type diterpenes consist of three structural subtypes, i.e., 11-and 7-membered ring compounds, and rearranged type (neovibsane-type) such as vibsanins B (12) and C (13), 1,3) and neovibsanin A (14), 2) respectively. Among these three subtypes, neovibsane-type diterpenes occupy a particular position in the vibsane-type natural products, owing to their unprecedented skeleton as well as intriguing biological activities. methylneovibsanin F (4), 15-O-methyl-18-oxoneovibsanin F (5), 2-O-methylneovibsanin H (6), 2-O-methylneovibsanin I (7), neovibsanin G (8), and 14-epi-neovibsanin G (9), were isolated from a methanol extract of the leaves of Viburnum awabuki. Their structures were elucidated to be uniquely rearranged vibsane-type diterpenes by spectroscopic analyses and comparison of NMR data with those of previously reported vibsane-type diterpenes. In addition, irradiation of vibsanin B (12) in methanol with a high-pressure Hg lump led to the direct formation of neovibsanins A (14) and B (15). These results gave a clue to understanding of the biogenetic interconversion of 11-membered vibsanins into neovibsanins.

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Section: -15)mentioning

confidence: 99%

“…

Vibsane-type diterpenes can be regarded as quite rare natural products because they occur exclusively in Viburnum species such as V. awabuki [1][2][3][4][5][6][7][8][9][10][11] and V. odoratissimum.

…”

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confidence: 99%

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Rearranged Vibsane-Type Diterpenes from Viburnum awabuki and Photochemical Reaction of Vibsanin B

Kubo

Matsuda

Yuasa

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…1,2) In the preceding paper, 3) we demonstrated that an eleven-membered vibsane-type diterpene, vibsanin B (11), exists in solution as two conformational isomers, CT and BC, which can transform to sevenmembered derivatives, vibsanin C (6) and its 5-epimer (6a) by thermal Cope rearrangement, respectively, as shown in Fig. 1.…”

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Seven-Membered Vibsane-Type Diterpenes with a 5,10-cis Relationship from Viburnum awabuki.

et al. 2002

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Viburnum awabuki (Caplifoliaceae) has elaborated a number of rarely occurring vibsane-type diterpenes, which can be subdivided into three types of eleven-membered, seven-membered and rearranged ones. 1,2) In the preceding paper, 3) we demonstrated that an eleven-membered vibsane-type diterpene, vibsanin B (11), exists in solution as two conformational isomers, CT and BC, which can transform to sevenmembered derivatives, vibsanin C (6) and its 5-epimer (6a) by thermal Cope rearrangement, respectively, as shown in Fig. 1. This result suggests the occurrence of natural 5-epimers corresponding to the previously reported sevenmembered vibsanins C (6), H (7), K (8), and 18-Omethylvibsanin K (9) and vibanin E (10) with a trans relationship on the C-5 and C-10 positions.4,5) Herein, we report the isolation and structure of five anticipated isomers, 5-epivibsanin C (1), 5-epi-vibsanin H (2), 5-epi-vibsanin K (3) and 18-O-methyl-5-epi-vibsanin K (4) and 5-epi-vibsanin E (5) from the methanol extract of the leaves of Viburnum awabuki.Compound 1 . These spectral data were very similar to those of vibsanin C (6), which was a typical seven-membered vibsane-type diterpene isolated from the title plant. In fact, analyses of two-dimensional (2D) NMR spectra such as quantum filtered-correlated spectroscopy (DQF-COSY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond correla- * To whom correspondence should be addressed. e-mail: fukuyama@ph.bunri-u.

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“…[11][12][13][14][15][16][17] These diterpenes can be divided into three subtypes such as 11-membered ring, 7-membered ring, and rearranged types. We have examined chemical components in the leaves of Viburnum odoratissimum collected in Taiwan to find out some of vibsane-type diterpenes.…”

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confidence: 99%