Kuraray Co., Ltd.

Koichi Ibata

Takashi Nishida

Masao Mizuno

Yoichi Ninagawa

Yasuyuki Tanaka

Tetsuo Takigawa

Masafumi Okada

A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit, ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mamammalian dolichols. The polyprenyl composition can be prepared by extracting the leaves of Ginkgo biloba or Cedrus deodara with an oil-soluble organic solvent; if required, hydrolyzing the extract; and subjecting the extract to one or more of chromatography, fractional dissolution, fractional refrigerating precipitation and molecular distillation, thereby separating and recovering a fraction having a specified Rf value in silica thin-layer chromatography.

Polyprenyl composition or compounds and process for the production

A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mammalian dolichols. The polyprenyl composition can be prepared by extracting the leaves of Ginkgo biloba or Cedrus deodara with an oil-soluble organic solvent; if required, hydrolyzing the extract; and subjecting the extract to one or more of chromatography, fractional dissolution, fractional refrigerating precipitation and molecular distillation, thereby separating and recovering a fraction having a specified Rf value in silica thin-layer chromatography.

Polyprenyl composition of compounds and process for the production

A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit, ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mammalian dolichols. The polyprenyl composition can be prepared by extracting the leaves of Ginkgo biloba or Cedrus deodara with an oil-soluble organic solvent; if required, hydrolyzing the extract; and subjecting the extract to one or more of chromatography, fractional dissolution, fractional refrigerating precipitation and molecular distillation, thereby separating and recovering a fraction having a specified Rf value in silica thin-layer chromatography.

Polyprenols or esters thereof, which are similar in the trans and cis configurations to dolichol, or mixtures thereof are obtained from the leaves of plants belonging to the genus Pinus L. of the family Pinaceae by extraction, if necessary followed by hydrolysis, esterification or transesterification or a combination thereof. These polyprenyl compounds and mixtures thereof are useful as favorable starting materials for the synthesis of dolichol.

Method of preparing polyprenyl compounds or mixtures thereof

There are provided polyprenyl compounds of the formula ##STR1## wherein ##STR2## represent a trans-isoprene unit and a cis-isoprene unit, respectively, n is an integer of 11-19, Z.sup.1 and Z.sup.2 combinedly represent .dbd.O, .dbd.CH--COOH,.dbd.CH--COOR.sup.1, .dbd.CH--CN, .dbd.C(CN)COOR.sup.2, .dbd.CH--CO--NH.sub.2, .dbd.CH--CO--N(R.sup.3) (R.sup.4), .dbd.CH--CO--NHR.sup.5, .dbd.CH--CH.sub.2 --N(R.sup.3) (R.sup.4), .dbd.CH--CH.sub.2 --NHR.sup.5 or .dbd.CH--CHO or Z.sup.1 is a hydrogen atom and Z.sup.2 is --CH.sub.2 COOH, --CH.sub.2 COOR.sup.6, --CH(CN)COOR.sup.2, --CH.sub.2 CN, --CH.sub.2 --CO--NH.sub.2, --CH.dbd.CH--N(R.sup.3) (R.sup.4) or --CH.sub.2 --CH.dbd.N--R.sup.5, R.sup.1, R.sup.2 and R.sup.6 each being a lower alkyl group, R.sup.3 and R.sup.4 each independently being a lower-alkyl, cycloalkyl, aryl or aralkyl group or R.sup.3 and R.sup.4 combinedly representing an alkylene group containing 2-5 carbon atoms, and R.sup.5 being a lower-alkyl, cycloalkyl, aryl or aralkyl group. These polyprenyl compounds can be synthesized starting with a polyprenol obtainable from leaves of a plant such as Ginkgo biloba or Cedrus deodara by extraction and as necessary followed by hydrolysis, or a reactive derivative thereof. The polyprenyl compounds are useful as intermediates for the synthesis of dolichol without the use of an expensive C.sub.5 chain extender.

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Kurashiki, Japan

Koichi Ibata