natural
product chemistry and medicinal
chemistry of triterpenes and triterpeniods, Squalene,
Material science, Biomaterials
Bioassay,
Pharmacological activity, Medicinal plant,
Herb, Herbal medicine, Chinese medicine, Fungus, Mushroom.
Manuscript ID: molecules-triterp-20080917-tw-Fang
Type of Paper: Review
Title: The Pharmacological Activities and Therapeutic Potentials of Squalene and Its Related Derivatives for Skin
Authors: Zih-Rou Huang 1, Yin-Ku Lin 2,3, and Jia-You Fang 1,*
1 Pharmaceutics Laboratory, Graduate Institute of Natural Products, Chang Gung University, Kweishan, Taoyuan, Taiwan
2 Graduate Institute of Clinical Medical Sciences, Chang Gung University, Kweishan, Taoyuan, Taiwan
3 Department of Traditional Chinese Medicine, Chang Gung Memorial Hospital, Keelung, Taiwan
E-mail:
[email protected]Abstract:
Squalene is a triterpene that is an intermediate of the cholesterol
biosynthesis pathway. Squalene, the main component of skin surface
polyunsaturated lipids, can show some advantages for skin such as
emollient, antioxidant, skin-hydrated, and antitumor activities. It is
also used as a material in the topically-applied vehicles such as lipid
emulsions and solid lipid nanoparticles. This review describes the
effect of squalene on skin for preventive or therapeutic aims. The
related substances of squalene, including β-carotene, ubiquinone
(CoQ10), vitamin A, vitamin E, and vitamin K, are also included in this
review article to introduce their benefits on skin physiology. We
summarize the investigations performed in previous reports from the in
vitro model to the clinical trials.
Keywords: Squalene, skin surface lipid, skin, antioxidant, topical delivery
Manuscript ID: molecules-triterp-20080918-za-Dubery
Type of Paper: Review
Title: Triterpenoid acids and triterpenoid glycosides in
Centella asiatica (L.)., a valuable medicinal herb
Authors: Jacinda James and Ian A Dubery
Affiliation: Department of Biochemistry, University of Johannesburg, South Africa
E-mail:
[email protected]Abstract:
Centella asiatica and other related species accumulate large quantities of pentacyclic triterpene saponins.
Centella
triterpenoids include asiaticoside, centelloside, madecassoside,
brahmoside, brahminoside, thankuniside, sceffoleoside, centellose, and
asiatic, brahmic, centellic and madecassic acids. Triterpene saponins
are common secondary metabolites and a number of these molecules are
synthesized via the isoprenoid pathway to produce a hydrophobic
triterpenoid structure (aglycone) containing hydrophilic sugar chain
(glycone). These characteristics have been attributed to the biological
activity of saponins. The
Centella
triterpenoids can be regarded as phytoanticipins due to their
antimicrobial activities and protective role against attempted pathogen
infection. Preparations of
C. asiatica
are used in traditional and alternative medicine due to the wide
spectrum of pharmacological activities associated with these secondary
metabolites. Here, the biosynthesis of triterpenoid saponins and
–sapogenins is reviewed and the range of metabolites found in
C. asiatica
summarized, together with their known biological activities. In
addition, most plant-derived pharmacologically active compounds have
complex structures, making chemical synthesis an economically
uncompetitive option. A particular important benefit is the ability to
manipulate and improve the production of desired compounds, thus
biotechnological approaches to increase the concentrations of the
metabolites are discussed.
Manuscript ID: molecules-triterp-01-br-Garcez
Type of Paper: Article
Title: Bioactive Pentacyclic Triterpenes from the Stems of
Combretum laxum Authors: Eder Bisoli, Walmir Silva Garcez, Lidilhone Hamerski, Caroline Tieppo and Fernanda Rodrigues Garcez*
Affiliation: Departamento de Qu�mica, Universidade Federal de Mato Grosso do Sul, Campo Grande, MS, Brasil, 79070-900
E-mail:
[email protected]Abstract:
Two new triterpene glucosides, b-D-glucopyranosyl 2a,3b,24-trihydroxyolean-12-en-28-oate
and b-D-glucopyranosyl 2a,3b,23,24-tetrahydroxyurs-12-en-28-oate,
in addition to nine known compounds belonging to three different (oleanane-,
ursane- and lupane-type) triterpene classes have been isolated from the stems
of a specimen of Combretum laxum growing
in the “Pantanal” of the central-western region of Brazil. Among the known
triterpenes, b-D-glucopyranosyl 2a,3b,6b-trihydroxyolean-12-en-28-oate
is reported for the first time in the Combretaceae while bellericoside and
asiatic acid are described for the first time in the genus Combretum. The structures of the isolated compounds have been
established on the basis of spectral techniques (1D-, 2D-NMR and MS). Their in vitro antifungal activities against
standard strains of Candida albicans,
C. krusei and Cryptococcus neoformans were also evaluated in this work.
Manuscript ID: molecules-triterp-20080922-es-Martin
Type of Paper: Article
Title:
Clavaric
acid and fasciculic acid: Biosynthesis and Molecular GeneticsAuthors: Juan F. Mart�n
1,2
and Ramiro P. Godio
21
�rea de Microbiolog�a, Facultad de Ciencias Biol�gicas y Ambientales,
Universidad de Le�n, Campus de Vegazana, s/n. 24071 Le�n, Spain
2 Instituto de Biotecnolog�a de Le�n (INBIOTEC), Avda. Real, 1. 24006 Le�n, Spain
E-mail:
[email protected]Abstract:
Clavaric acid is a potent antitumor agent produced by the
mushroom-forming basidiomycete Hypholoma sublateritium. Clavaric acid
is structurally similar to fasciculic acid, a related triterpenoid
produced by Hypholoma fasciculare that is described as a calmodulin
inhibitor.
These two compounds are derived from squalene by the
action of enzymes that convert squalene to 2,3-dioxidesqualene and this
intermediate to clavarinone, a direct precursor of clavaric acid or
fasciculic acid. One of these enzymes, the squalene oxidase, is common
for primary metabolism (ergosterol biosynthesis) and secondary
metabolism, whereas the late enzymatic steps are specific for the
biosynthesis of clavaric acid and fasciculic acid. Molecular genetics
studies allowed us to clone and characterise the genes encoding these
enzymes. These studies have provided a considerable insight into the
biosynthesis of triterpenoids in fungi, providing new potent
pharmacologically-active compounds. Squalene epoxidases and
oxidosqualene cyclases with modified consensus motifs in their active
centers appear to play an important role in determining the oxidation
and modification reactions that may result in specific secondary
metabolites.