Clerodane diterpene
Encyclopedia
A clerodane diterpene (or clerodane diterpenoid) is a compound terpene
derivative, more precisely a bicyclic diterpenoid. It is rather a rare form of diterpenoid and is structurally related to the bicyclic diterpenoids labdane and ginkgolide. Its biosynthesis in plants (mostly present in the families Lamiaceae
and Asteraceae
) takes place in the chloroplast
s. Some forms can be useful intermediates in organic synthesis.. Some clerodanes like clerodin (3-desoxy-caryoptinol) from the leaves of Clerodendrum infortunatum
(Verbenaceae
) have anthelminthic properties, others like ajugarins are repellent to herbivore predators (mostly insects and their larvae) or have a very bitter taste, such as gymnocolin.
Some examples for clerodanes are ajugarins I to V extracted from bugleweeds like Ajuga remota, Ajuga ciliata, Ajuga decumbens, common skullcap (Scutellaria galericulata)
, and germanders (Teucrium sp.)
, cascarillin from Croton eleuteria, columbins from Jateorhiza columba, Jateorhiza palmata and guduchi (Tinospora cordifolia
), gymnocolin from Gymnocolea inflata, hardwickiic acid from Hardwickia
species (Fabaceae
).
Neo-clerodane diterpenes can have hallucinogenic properties such as salvinorin A, a trans-neoclerodane diterpenoid from Salvia divinorum
.
Terpene
Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium. They are often strong smelling and thus may have had a protective...
derivative, more precisely a bicyclic diterpenoid. It is rather a rare form of diterpenoid and is structurally related to the bicyclic diterpenoids labdane and ginkgolide. Its biosynthesis in plants (mostly present in the families Lamiaceae
Lamiaceae
The mints, taxonomically known as Lamiaceae or Labiatae, are a family of flowering plants. They have traditionally been considered closely related to Verbenaceae, but in the 1990s, phylogenetic studies suggested that many genera classified in Verbenaceae belong instead in Lamiaceae...
and Asteraceae
Asteraceae
The Asteraceae or Compositae , is an exceedingly large and widespread family of vascular plants. The group has more than 22,750 currently accepted species, spread across 1620 genera and 12 subfamilies...
) takes place in the chloroplast
Chloroplast
Chloroplasts are organelles found in plant cells and other eukaryotic organisms that conduct photosynthesis. Chloroplasts capture light energy to conserve free energy in the form of ATP and reduce NADP to NADPH through a complex set of processes called photosynthesis.Chloroplasts are green...
s. Some forms can be useful intermediates in organic synthesis.. Some clerodanes like clerodin (3-desoxy-caryoptinol) from the leaves of Clerodendrum infortunatum
Clerodendrum infortunatum
Clerodendrum infortunatum is a perennial shrub belonging to the family Lamiaceae, also sometimes classified under Verbenaceae. It is the type species among ~400 species of Clerodendrum...
(Verbenaceae
Verbenaceae
Verbenaceae, commonly known as the verbena family or vervain family, is a family of mainly tropical flowering plants. It contains trees, shrubs and herbs notable for heads, spikes, or clusters of small flowers, many of which have an aromatic smell.Recent phylogenetic studies have shown that...
) have anthelminthic properties, others like ajugarins are repellent to herbivore predators (mostly insects and their larvae) or have a very bitter taste, such as gymnocolin.
Some examples for clerodanes are ajugarins I to V extracted from bugleweeds like Ajuga remota, Ajuga ciliata, Ajuga decumbens, common skullcap (Scutellaria galericulata)
Scutellaria galericulata
Common Skullcap , also known as Marsh Skullcap or Hooded Skullcap, is a hardy perennial herb native to northern areas of the Northern Hemisphere, including Europe, Asia, and much of North America. It is a member of the mint family...
, and germanders (Teucrium sp.)
Teucrium
Teucrium is a genus of perennial plants, of the family Lamiaceae. Common names for this genus include germanders. These species are herbs, shrubs or subshrubs...
, cascarillin from Croton eleuteria, columbins from Jateorhiza columba, Jateorhiza palmata and guduchi (Tinospora cordifolia
Tinospora cordifolia
Tinospora cordifolia, which is known by the common name Guduchi, is an herbaceous vine of the family Menispermaceae indigenous to the tropical areas of India, Myanmar and Sri Lanka....
), gymnocolin from Gymnocolea inflata, hardwickiic acid from Hardwickia
Hardwickia
Hardwickia is a genus of flowering plants in the legume family, Fabaceae. It belongs to the sub family Caesalpinioideae....
species (Fabaceae
Fabaceae
The Fabaceae or Leguminosae, commonly known as the legume, pea, or bean family, is a large and economically important family of flowering plants. The group is the third largest land plant family, behind only the Orchidaceae and Asteraceae, with 730 genera and over 19,400 species...
).
Neo-clerodane diterpenes can have hallucinogenic properties such as salvinorin A, a trans-neoclerodane diterpenoid from Salvia divinorum
Salvia divinorum
Salvia divinorum is a psychoactive plant which can induce dissociative effects and is a potent producer of "visions" and other hallucinatory experiences...
.