Sesquiterpenes of nine european liverworts from the genera, Anastrepta, bazzania, jungermannia, lepidozia and Scapania

Neils H. Andersen, P. Bissonette, C. B. Liu, Belinda Shunk, Yoshimoto Ohta, Chia Li W Tseng, Ana L Moore, S. Huneck

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

The essential oils of fourteen liverwort specimens from nine species of the Jungermanniales have been examined as to their sesquiterpenes. The barbatenes prove to be present in detectable amounts in all but one species. Bazzanene is frequently found with the barbatenes and new chemical evidence does not support the previously assigned structure but is consistent with a structure diastereomeric to trichodiene. This is consistent with a biogenetic rationale for the barbatene skeleton. Anasterptene, a novel crystalline tetracyclic hydrocarbon, has been found in numerous oils, and chemical degradation established a common skeleton with myliol. The samples of genus Scapania elaborate sesquiterpenes of the enantiomeric humulene-longifolene sequence. New members of this group found are (-)-β-longipinene, (-)-longipipanol, and (+)-γ-himachalene. The related germacrene series is represented by a cadinene, (-)-α-ylangene, and (-)-sativene. A series of cis-fused selinenes have also been found, which are more closely allied to the germacrene-sativene group than to typical trans-fused selinenes. One of these selinenes is shown to be the same as the material previously designated as sibirene. Scapania undulata also elaborates (+)-α- and β-chamigrene, and a number of novel hydrocarbons of still unknown structure.

Original languageEnglish
Pages (from-to)1731-1751
Number of pages21
JournalPhytochemistry
Volume16
Issue number11
DOIs
Publication statusPublished - 1977

Fingerprint

Hepatophyta
germacrene
Sesquiterpenes
Hydrocarbons
Skeleton
sesquiterpenoids
skeleton
mosses and liverworts
hydrocarbons
humulene
chemical degradation
Volatile Oils
Oils
essential oils
Crystalline materials
Degradation
oils
sampling
sativene
Jungermanniales

Keywords

  • bazzanene
  • cadinene
  • chamigrenes
  • cis-fused selinenes.
  • ent-sesquiterpenes
  • gymnomitrol
  • Hepaticae
  • himachalene-longifolene-type sesquiterpenes
  • Jungermanniales
  • myliol
  • Scapania
  • sibirene
  • ylangene

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

Cite this

Andersen, N. H., Bissonette, P., Liu, C. B., Shunk, B., Ohta, Y., Tseng, C. L. W., ... Huneck, S. (1977). Sesquiterpenes of nine european liverworts from the genera, Anastrepta, bazzania, jungermannia, lepidozia and Scapania. Phytochemistry, 16(11), 1731-1751. https://doi.org/10.1016/0031-9422(71)85081-1

Sesquiterpenes of nine european liverworts from the genera, Anastrepta, bazzania, jungermannia, lepidozia and Scapania. / Andersen, Neils H.; Bissonette, P.; Liu, C. B.; Shunk, Belinda; Ohta, Yoshimoto; Tseng, Chia Li W; Moore, Ana L; Huneck, S.

In: Phytochemistry, Vol. 16, No. 11, 1977, p. 1731-1751.

Research output: Contribution to journalArticle

Andersen, Neils H. ; Bissonette, P. ; Liu, C. B. ; Shunk, Belinda ; Ohta, Yoshimoto ; Tseng, Chia Li W ; Moore, Ana L ; Huneck, S. / Sesquiterpenes of nine european liverworts from the genera, Anastrepta, bazzania, jungermannia, lepidozia and Scapania. In: Phytochemistry. 1977 ; Vol. 16, No. 11. pp. 1731-1751.
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abstract = "The essential oils of fourteen liverwort specimens from nine species of the Jungermanniales have been examined as to their sesquiterpenes. The barbatenes prove to be present in detectable amounts in all but one species. Bazzanene is frequently found with the barbatenes and new chemical evidence does not support the previously assigned structure but is consistent with a structure diastereomeric to trichodiene. This is consistent with a biogenetic rationale for the barbatene skeleton. Anasterptene, a novel crystalline tetracyclic hydrocarbon, has been found in numerous oils, and chemical degradation established a common skeleton with myliol. The samples of genus Scapania elaborate sesquiterpenes of the enantiomeric humulene-longifolene sequence. New members of this group found are (-)-β-longipinene, (-)-longipipanol, and (+)-γ-himachalene. The related germacrene series is represented by a cadinene, (-)-α-ylangene, and (-)-sativene. A series of cis-fused selinenes have also been found, which are more closely allied to the germacrene-sativene group than to typical trans-fused selinenes. One of these selinenes is shown to be the same as the material previously designated as sibirene. Scapania undulata also elaborates (+)-α- and β-chamigrene, and a number of novel hydrocarbons of still unknown structure.",
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AU - Andersen, Neils H.

AU - Bissonette, P.

AU - Liu, C. B.

AU - Shunk, Belinda

AU - Ohta, Yoshimoto

AU - Tseng, Chia Li W

AU - Moore, Ana L

AU - Huneck, S.

PY - 1977

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N2 - The essential oils of fourteen liverwort specimens from nine species of the Jungermanniales have been examined as to their sesquiterpenes. The barbatenes prove to be present in detectable amounts in all but one species. Bazzanene is frequently found with the barbatenes and new chemical evidence does not support the previously assigned structure but is consistent with a structure diastereomeric to trichodiene. This is consistent with a biogenetic rationale for the barbatene skeleton. Anasterptene, a novel crystalline tetracyclic hydrocarbon, has been found in numerous oils, and chemical degradation established a common skeleton with myliol. The samples of genus Scapania elaborate sesquiterpenes of the enantiomeric humulene-longifolene sequence. New members of this group found are (-)-β-longipinene, (-)-longipipanol, and (+)-γ-himachalene. The related germacrene series is represented by a cadinene, (-)-α-ylangene, and (-)-sativene. A series of cis-fused selinenes have also been found, which are more closely allied to the germacrene-sativene group than to typical trans-fused selinenes. One of these selinenes is shown to be the same as the material previously designated as sibirene. Scapania undulata also elaborates (+)-α- and β-chamigrene, and a number of novel hydrocarbons of still unknown structure.

AB - The essential oils of fourteen liverwort specimens from nine species of the Jungermanniales have been examined as to their sesquiterpenes. The barbatenes prove to be present in detectable amounts in all but one species. Bazzanene is frequently found with the barbatenes and new chemical evidence does not support the previously assigned structure but is consistent with a structure diastereomeric to trichodiene. This is consistent with a biogenetic rationale for the barbatene skeleton. Anasterptene, a novel crystalline tetracyclic hydrocarbon, has been found in numerous oils, and chemical degradation established a common skeleton with myliol. The samples of genus Scapania elaborate sesquiterpenes of the enantiomeric humulene-longifolene sequence. New members of this group found are (-)-β-longipinene, (-)-longipipanol, and (+)-γ-himachalene. The related germacrene series is represented by a cadinene, (-)-α-ylangene, and (-)-sativene. A series of cis-fused selinenes have also been found, which are more closely allied to the germacrene-sativene group than to typical trans-fused selinenes. One of these selinenes is shown to be the same as the material previously designated as sibirene. Scapania undulata also elaborates (+)-α- and β-chamigrene, and a number of novel hydrocarbons of still unknown structure.

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KW - gymnomitrol

KW - Hepaticae

KW - himachalene-longifolene-type sesquiterpenes

KW - Jungermanniales

KW - myliol

KW - Scapania

KW - sibirene

KW - ylangene

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EP - 1751

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

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ER -