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Acyclic and incompletely cyclized triterpene alcohols in the seed oils of theaceae and Gramineae

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Lipids

Abstract

The triterpene alcohol constituents of the non-saponifiable lipids of two Theaceae seed oils, sasanqua and camellia oils, and two Gramineae seed oils, wheat germ and rice bran oils, were investigated. This led to the isolation and characterization of one acyclic and eight incompletely cyclized triterpene alcohols. They are camelliol A, camelliol B, camelliol C, achilleol A, helianol, isohelianol, sasanquol, graminol A [(13R, 14R)-3,4-seco-25(10→9)abeo-8α,9β,10α-podioda-4,17,21-trien-3-ol], and (2Z,6Z,10Z,14E,18E)-farnesylfarnesol. Two other compounds isolated were characterized as (2Z,6Z,10E,14E)-geranylfarnesol, a sesterterpene alcohol, and phytol, a diterpene alcohol. Graminol A and (2Z,6Z,10E,14E)-geranylfarnesol are considered to be new natural products.

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Abbreviations

GC-MS:

gas chromatography-mass spectroscopy

GLC:

gas-liquid chromatography

HPLC:

high-performance liquid chromatography

HREIMS:

high-resolution electron impact mass spectra

IR:

infrared

NOE:

nuclear Overhauser effect

NMR:

nuclear magnetic resonance

NSL:

nonsaponifiable lipids

RRT:

relative retention time

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Authors and Affiliations

  1. School of Pharmaceutical Sciences, Toho University, 274-8510, Chiba, Japan

    Kazuo Koike & Tamotsu Nikaido

  2. College of Pharmacy, Nihon University, 274-8555, Chiba, Japan

    Yumiko Kimura

  3. Chiba Factory, Riken Vitamin Co., Ltd., 261-0002, Chiba, Japan

    Norio Sashida

  4. College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Chiyoda-ku, 101-8308, Tokyo, Japan

    Toshihiro Akihisa, Taiji Matsumoto & Motohiko Ukiya

Authors
  1. Toshihiro Akihisa
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  2. Kazuo Koike
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  3. Yumiko Kimura
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  4. Norio Sashida
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  5. Taiji Matsumoto
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  6. Motohiko Ukiya
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  7. Tamotsu Nikaido
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Correspondence to Toshihiro Akihisa.

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Akihisa, T., Koike, K., Kimura, Y. et al. Acyclic and incompletely cyclized triterpene alcohols in the seed oils of theaceae and Gramineae. Lipids 34, 1151–1157 (1999). https://doi.org/10.1007/s11745-999-0466-5

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  • DOI: https://doi.org/10.1007/s11745-999-0466-5

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