pharmacognosy -2 phg 322 - psau.edu.sa · pharmacognosy -2 phg 322. the marine biosphere marine...
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Prof. Dr. Amani S. Awaad
Professor of PharmacognosyPharmacognosy Department,
College of Pharmacy Salman Bin Abdulaziz
University,
Al-Kharj. KSA.
Email: [email protected]
Pharmacognosy -2
PHG 322
The marine biosphere
Marine secondary metabolites
biological activities Marine secondary metabolites
Some marine comopounds
Marine Natural
Products
5
• More than 70 % of the planet’s surface is covered by oceans.
• The great biodiversity of marine environment.
• More than 300 000 species of plants and animals are described.
• Great number of marine organism have no terrestrial counterparts.
• The very special living condition for marine organisms led them to adapt different physiological and behavioural characters which consequently resulted in novel biologically active molecules.
• Sea organisms are mostly unexplored reservoirs of new drugs.
• A small number of marine plants, animals, and microbes have already yielded more than 12000 novel chemicals.
• Hundreds of new compounds still being discovered every yea
Marine Natural Products
Importance of marine environment
Phases of work on marine chemistry
Marine Natural Products
In the 1950’s researchers were interested in
studying the marine spines and shells of sea
urchins with beautiful colors.
In the 1970’s interest of researchers was
attracted to the halogenated metabolites from
red algae.
From the 1980’s till now the marine
chemistry was directed by the currently used
sophisticated and smart biological assays.
Interest switched from marine algae to
marine invertebrates.
Marine Natural Products
Problems of marine research
1- The lack of trained personal.
2- Diving hazards.
3- The marine trips are effort, time and money consuming.
4- The time consuming experiments.
5- The scarcity of the starting organism to carry out the
complete study.
6- Recollection problems of the same organisms in the
dynamic environment.
7- Difficulties in culturing of marine organisms in the lab.
8- Most of the marine secondary metabolites are polar
compounds, so additional difficulties with extraction,
fractionation and separation are faced.
9- The marine organisms are usually associated with parasitic
commensal or symbiotic flora.
10- The lack of folk medicine information or ethnobotanical
documentation.
Marine Natural ProductsThe marine biosphere
Marine organisms are classified into the following
phyla: 1)Monera, 2)Protista, 3)Metazoa,
4)Higher plants
* Monerans are one-celled organisms that have no nucleus or organelles.
*Monerans are individual cells that survive on their own.
*They do not work together in groups. However, they can be found in
pairs, clumps, or in chains.
*The kingdom of Monera is divided into two types or
organisms, bacteria and cyanobacteria.
1) Monera
*They make their own food through the process of photosynthesis.
*These cells are found in oceans, lakes, ponds, swimming pools, and
moist soil.
*They are an important food source for many of the animals in the
water.
*They can be found alone, in colonies, or long thread like chains.
Cyanobacteria (blue-green algae )
Marine Natural ProductsThe marine biosphere
2) Protista
a diverse group of eukaryotic microorganisms.
unicellular, or multicellular without specialized
tissues.
They include ; a-marine fungi and b-algae.
A-marine fungi
live saprophytic on algae, plants or
animals.
parasites on shells, crabs, sponges, in the
GIT of fishes.
Or symbiotic as in lichens.
Source of antibacterial, antifungal,
cytotoxic and anti-inflammatory agents.
produce several secondary metabolites e.g.
alkaloids, terpenoids and polyketides.
Marine Natural ProductsThe marine biosphere
2) Protista
b-algae
are a large and diverse group of simple,
typically autotrophic organisms, ranging
from unicellular to multicellular forms.
They are photosynthetic and simple.
There are nearly 30,000 algae species.
They could be divided into the
following groups:
1- Red algae (Rhodophyta)
2- Brown algae (Phaeophyta)
3- Green algae (Chlorophyta)
4- Golden brown algae
5- Yellow algae and diatoms
(Chrysophyta)
6- Euglenophyta
7- Blue green algae
8- Dinoflagellates (Pyrrophyta)
Chlorophyta (green algae):About 8000 species.
Mostly live in fresh water. Chlorophyll a and c.
Rhodophyta (red algae) About 5000 – 6000
species.95% are marine.Chlorophyll a, phycoerythrin.
Phaeophyta (brown algae) About 1500-2000 species.99%
are marine.Chlorophyll a, c and phycoerythrin
Marine Natural ProductsThe marine biosphere
3)Metazoa(Marine animal)
Marine vertebrates and invertebrates were subjected to chemical
study.
These studies covered representative phyla:
Porifera ,Cnidaria, Mollusca, Chordat, Echinodermata,Annelida,
Over 9000 known species. Aquatic sessile filter feeders.
50% of the natural products reported from marine invertebrates.
About 2600 metabolites were isolated.
a)Porifera (Sponges األسفنج)
b)Cnidaria
This phylum include: soft and hard
corals, gorgonians, sea pens, jellyfish,
sea wasps and sea anemones.
Sea pens Corals المرجانSea anemones
شقائق النعمانJellyfish قنديل البحر
Marine Natural ProductsThe marine biosphere
3)Metazoa(Marine animal)
c)Mollusca الرخويات
This phylum contains a highly diverse group of
animals including 50000 species and 60000 fossil
molluscs. snails الحلزون , tusk shells, shellfish المحار ,
octopus اإلخطبوط , squids حبار , mussels بلح البحر
d)Chordata حبليات
This phylum includes tunicates and vertebrates. The most
distinctive morphological features of chordates are the
notochord, nerve cord, and visceral clefts and arches.
e)Echinodermata قنفذيات او شوكيات
With 7000 extant and 13000 extinct species.
Marine Natural Products
Marine secondary metabolites
During the last 30-40 years numerous novel compounds have been isolated from
marine organisms having biological activities such as Antibacterial, Antiviral,
Antitumer, Antiparasitic, Anticoagulants, Antimicrobial, Anti-inflammatory and
cardiovascular active products.
•Antimicrobial agent and
antibiotics
•Antiviral compounds
•Antiparasitic agents
•Anticancer agents
•Anticoagulant agents
•Cardiovascular and
Neurophysiological agents
•Anti-inflammatory and
Antispasmodic agents
Marine Natural ProductsMarine secondary metabolites
1)Antimicrobial agent and antibiotics
•Cephalosporin: It is obtained from the
marine fungus, Cephalosporium acremonium. It
has been widely used as an antibiotic drug active
against microbes insensitive to penicillin and
ampicillin.
•Istamycins: This is the fermentation product of
marine microorganisms Strptomyces lenjimariesis.
•Zonarol and Isozonarol: They are both
obtained from Dictyopteris zonaroides (Brown
algae). They are used as antimicrobial agents.
•Halotoxin A, B, C: It is obtained from the
Stichopus japonicas ( Sea cucumber). It is
antifungal in nature.
•Ircinin: It is obtained from the Ircin oros.
Zonarol
Marine Natural ProductsMarine secondary metabolites
1)Antimicrobial agent and antibiotics
Squalamine
• is the first aminosterol isolated from the dogfish
shark Squalus acanthias (squalidae).
• It has potent antimicrobial activity against
Staphylococcus aureus and antitumour properties.
• in clinical trials for the treatment of advanced
non-small-cell lung cancer.
Cribrostatins
• isolated from a blue sponge Cribrochalina sp.
and showed potent antineoplastic and
antimicrobial activities.
• Cribrostatin 3 has potent inhibitory activity
against penicillin- resistant Neisseria gonorrheae
Dogfish shark
N
O
O
O
CH3
H3C
C2H5O
Cribrostatine 2
Cribrochalina sp.
Marine Natural ProductsMarine secondary metabolites
2)Antiviral compounds
•Ara-A: a semi-synthetic substance based on
the arabinosyl nucleosides, isolated from the
Tethya crypta.
•Avarol and Avarone: It is obtained
from the sponge, Disidea avara. These
compounds inhibit the immunodeficient virus,
have high therapeutic indices and the ability to
cross blood brain barrier (bbb). These
compounds have potential use in the treatment
of AIDS.
•Eudostomin-A: It is obtained from the
Eudostoma olivaceum.
•Patellazole-B: It is obtained from the
Ascidian lissocilium patella. has very potent
in vitro activity against herpes simplex
viruses.
H OH
OH
Avarol
H
6` 4`
O
O
Avarone
Eudistoma olivaceum
Tethya sp.
Ara-A
Marine Natural Products
Marine secondary metabolites
3)Antiparasitic Compounds
- Domic acid: It is obtained from the red
algae, Chondria armata. It is used as
anthelmintic.
- Cucummechinoside-F: It is obtained
from the sea cucumber. It is used as
antiprotozoal activity.
- Bengamide-F: It is obtained from the
sponges, nudibranch and a zoanthid.
- Laminine: It is obtained from
Laminaria angustata. It is use as an
anthelmintic as well as smooth muscle
relaxant.
Domic acid
Bengamide-F
Marine Natural Products
Marine secondary metabolites
4)Anticancer agents
• Sinularin: It is
obtained from the Sinularia
flexibilis.
• Halitoxin: It is
obtained from the helieloma
viridis.
• Tocotrienol: It is obtained
from brown algae, Sargassum
tortile.
• Geranylhydroquinone : It
is obtained from the chloform
extract of Aplidium species.
Sinularin
HalitoxinTocotrienol
Geranylhydroquinone
Marine Natural Products
Marine secondary metabolites
5)Anticoagulant agents
•Carageenan: It is obtained
from the Chondrus, Euchauma and
Gigrtina. It is reported
anticoagulant activity.
•Galaxtan sulphuric acid: It is
obtained from the Irdaea
laminaroides.
Marine Natural Products
Marine secondary metabolites
6)Cardiovascular and Neurophysiological agents
• Eldoisin: It is obtained from the
Eledone moschata (cephalopod). It is powerful
hypotensive compound obtained from posterior
salivary gland of cephalopod.
• Octapamine: It is obtained from the
Octopus vulgaris, O. Macropus and E. Moschata.
Its gives cardiovascular and adrenergic response.
• Tetramine: It is obtained from the Naptunea
antique. It shows curare like Effect.
• Laminine: It is obtained from the Laminaria
angustata. It is used as hypotensive agent.
Marine Natural Products
Marine secondary metabolites
7)Anti-inflammatory and Antispasmodic agents
• Manoalide: It is obtained from the
Luffariella variabilis. It is act by direct
inactivation of phospholipase A2, which is
present in some neurotoxins and also has a
role in synthesis of PGs in humans.
• Tetradoxin: It is obtained from the
puffer fishes Spherides rubripes. It is used
as strong antispasmodic.
• Flustramine A and B: It is
obtained from the Flustra foliaceal
(Swedish marine moss animal). It is used
as muscle relaxant.
O
O
HO
HO
O
Manoalide
Flustra folia