QUINON

Lia Marliani, M.Si., Apt.

Biologi Farmasi, Sekolah Tinggi Farmasi Bandung
Quinone
• Aromatic di-ketone
• Quinones are potentially derivable by oxidation of suitable phenolic
compounds, catechols (1,2-dihydroxybenzenes) giving rise to ortho-
quinones and quinols (1,4-dihydroxybenzenes) yielding para-quinones
Quinone
• There are four main groups of quinones :
 monocyclic benzoquinones,
 dicyclic naphthoquinones,
 tricyclic anthraquinones,
 and phenanthraquinones
Benzoquinones

Irisquinone obtained from plant sources

like Iridaceae latea pallasii (Iridaceae)
and used in antineoplastic Chinese
medicines are effective against
transplantable rodent tumors.
Irisquinone was also isolated from Iris
kumaoensis in India and used as a
sensitizer for radiation therapy of cancer
 Naphthoquinones

• Quinone named hydrolapachol-2-hydroxy-1,4-naphthoquinone has proved to

have an activity against Plasmodium lophurae. Plumbagin and other related
quinones have cured Leishmania subsp. infections, while diospyrin was found to
have an action against Leishmania donovani. The quinones of Diospyros, mainly
plumbagin and 7-methyljuglone, were shown to possess good antibacterial
activity in various strains of bacteria, while the dimeric benzoquinone,
microphyllone was reported to possess antiallergic properties.
• Jouglon from Juglans regia (Juglandaceae), with bacteriostatic and fungistatic
activity
• Droseron from Drosera sp. (Droseraceae), with spasmolitic action in respiratory
diseases
Naphthoquinones

• Lawsone from Impatiens glandulifera

• Plumbagin from Plumbago subsp.
• Lapachol from Tacoma stans (Bignoniaceae),
yellow pigment with cytostatic properties
• Alkannin from Alkanna tinctoria (Bignoniaceae),
red substance used in food production as
pigment
• Shikonin from Lithospermum erythrorhizon
• Phylloquinone
• Diospyrin from Diospyrons melanoxylon
Anthraquinones
• Anthraquinones are derivatives of tricyclic
aromatic compound—anthracen
• These substances are important, naturally
occurring pigments which are widely
distributed in nature. There are anthraquinones,
anthrons, anthranols, and dianthrons in this
group. Anthraquinons and anthrons differ in the
degree of oxidation of basic structure, while
anthranols are tautomeric forms of anthrons
Anthraquinones
 Dianthrone
• Sennidin A and B—is an isodianthron (build from two parts of
rein) and found in Cassia acutifolia and Cassia angustifolia
(Caesalpinacea)
• Sennosides A and B—D-glucosides (8 and 80) of sennidin A
and B, main active bodies in Folium Sennae
• Sennosides C and D—heterodianthron glucosides of
aloeemodin and rein
• Sennosides E and F—are oxalic derivatives of sennosides C
and D which occur in roots and rootstocs of Rheum
Palmatum (Polygonaceae) and in cortex of Rhamnus
purshiana (Rhamnaceae)
Dianthrone

• Hypericin (naphthodianthron) is a dark red

dimer compound in Hypericum perforatum
(Hypericaceae)/ St John’s Wort. It is well soluble
in alcohol, poorly in water. Hypericum
perforatum L. is an herbaceous perennial plant,
belongs to Hypericaceae family
• Hypericin is also being investigated for its
antiviral activities, in particular for itspotential
activity against HIV
Phenanthraquinones

• Denbinobin was isolated from Dendrobium moniliforme Lindl.

(Orchidaceae) and related species widely available in Japan, China, and
Australia [46]. The plants were historically used for herbal preparations like
Shih-hu in China. Denbirobin, also isolated from the stems of
Ephamerantha lanchophylla, induced apoptosis in human colon cancer
HCT-116 cells.
• There is only one report on its HPLC analysis using a Comosil 5C-18 AR
column and mobile phase of water–acethonitrile (50:50, v=v)
Benzoquinones, anthraquinones and
naphthaquinones

Benzoquinones, such as 2,6-dimethoxybenzoquinone

(1.62), are present in root exudates of maize and
stimulate parasitic plants to form haustoria (Matvienko
et al., 2001). Ubiquinones, such as ubiquinone(3)
(1.63),where (3) indicates the number of isoprenoid
sidechains, is also known as Coenzyme Q and has a role
in electron transport in the mitochondria
Naphthaquinones are rare. Among the
naphthaquinones juglone (1.64) is relatively common. It
is found in walnuts. Anthraquinone is the most widely
distributed of the quinones in higher plants and fungi.
There are numerous compounds. The anthtraquinone
emodin (1.65) occurs as a rhamnoside in rhubarb roots
Biosynthesis
 Biosynthesis

The shikimate pathway provides an

alternative route to aromatic
compounds, particularly the aromatic
amino acids l-phenylalanine, l-
tyrosine, and l-tryptophan
Quinone
Biosynthesis
TLC
• Prior to TLC, the powdered plant material is extracted for 5 min with methanol
(1 g of plant in 100 mL) then filtered. It is necessary to hydrolyse the extract to
characterize the aglycones and for this 1 g of powder plant is heated under
reflux with X mL 7.5% hydrochloric acid for 15 min. After cooling, the mixture is
extracted by shaking with X mL of chloroform or ether. The organic phase is
then taken and concentrated to about 1 mL, and then used for TLC.
• Chromatography is performed on silica gel precoated plates with light
petroleum-ethyl acetate-formic acid (75 : 25 : 1) or ethyl acetate-methanol-
water (100 : 13.5 : 10) for all anthracene drug extracts except for senna. In this
case, n-propanol-ethyl Acetate-water-glacial acetic acid (40 : 40 : 29 : 1) is
used.
• For the non-laxative dehydrodianthrones of St John’s wort (Hypericum
perforatum), TLC is performed with the eluent toluene-ethyl formate-formic
acid (50 : 40 : 10).
• Following TLC, all anthracene derivatives can be readily detected because
they quench fluorescence when irradiated at UV 254 nm and give yellow or
red-brown fluorescence. Different specific reagents are also used for detection
Detection methods and spray reagents
Detection methods and spray reagents
Detection methods and spray reagents
Detection methods and spray reagents