International
Volume   Journal
I Number 2 2010 for Environmental Rehabilitation and Conservation
[23-25]
Volume I No. 2 2010
[ISSN 0975 - 6272] [23-25] [ISSN 0975 - 6272]
Kumar & Jagwan
Determination of structure of new anthraquinone from the flowers of
Marigold from Temperate zone of Garhwal Himalaya of Uttarakhand
Pramod Kumar1 and J.S. Jangwan2
Received: March 10, 2010 ⏐ Accepted: June 20, 2010 ⏐ Online: August 27, 2010
Abstract
The plant of marigold (Genda) is native of
Mexico but this herbaceous plant is widely
cultivated in all the parts of our contrary for
commercial purpose and also grown in the
gardens as an ornamentally. The botanical
name of marigold is Tagetes erecta which
belongs to family Asteraceae. The flowers are
the source of yellow dye, which is commonly
used to dye cotton. The present study related
with investigation as isolation and structure
of a new anthraquinone together with β-
Sitosterol and 6,7-dimethoxy xanthopurpurin.
The compound was determinate with the help
chemicals and of spectral studies and
comparison with authentic sample and
reported data (Potter and Thomas 1995).
Keywords: Marigold ⏐ Temperate zone ⏐
Garhwal Himalaya ⏐ Anthraquinone
For correspondence:
1
Department of Botany, HNB Garhwal University
Campus Badshahithul, Tehri Garhwal, India
Email: pramoduniyal99@redissmail.com
2
Department of Chemistry, HNB Garhwal University
Campus, Badshahithul, Tehri, India
Determination of structure of new anthraquinone from the flowers of Marigold from Temperate zone of Garhwal Himalaya
 
Introduction
Marigold is erect annual aromatic herb which
has simple leaves, yellow/orange
homogamous flowers. Besides the dyes, the
pastes of flowers were also applied as
medicinally on wound and cuts (Gaur, 1999).
Tagetes erecta and Tagetes paluta are
commonly found in tropical as well as
temperate zones of Himalaya. Principle
constituents isolated from flowers of Tagetes
minuta are anthocyanins and its derivatives
(Prakash Rao and Putlano 2000). Some long
chain fatty acids, aromatic hydrocarbons and
phenyl acetaldehydes are extracted from
floral extract of Tagetes erecta (Chawdhury
2001). The present experimental studies
explain the isolation and structure of a new
anthraquinone glycoside together with β-
Sitosterol and 6,7-dimethoxy xanthopurpurin.
Materials and Methods
Collection of plant material
The flowers of Genda were collected from the
different parts of Tehri district of Uttarakhand
during the month of August-September 2000.
The plant was identified with the help of
voucher specimen of Herbarium of
23

Volume I Number 2 2010 [23-25]
[ISSN 0975 - 6272]
Department of Botany, D.A.V. (P.G.) College
Dehradun.
Extraction and isolation
The air-dried and coarsely powered flowers of
the plant were defatted with light petroleum in
a soxhlet. The defatted mass was exhaustively
extracted repeatedly with 90 % aqueous
EtOH, until the extractive became colourless.
All the extracts were mixed and concentrated
under reduced pressure using rotatory vacuum
evaporator. The concentrated extract was
adsorbed on Silica gel and fractionated
through column chromatography using the
solvent system of chloroform-methanol
(95:5). The polarity of solvent was gradually
increased by addition of methanol. Repeated
column chromatography afforded compounds
PT-1, PT-2, and PT-3 with some other
inseparable compounds.
Results and Discussion
The ethanolic extract of flowers of Tagetes
erecta on repeated column chromatography
over silica gel afforded compounds PT-1, PT-
2 and PT-3. Compounds PT-2 and PT-3 were
identified as β-Sitosterol and 6,7-dimethoxy
xanthopurpurin by comparison with authentic
sample and reported data (Potter and Thomas
1995).
Compound: PT-1
It was crystallized from methanol as
crystalline solid. On the basis of elemental
analysis and molecular weight determination
its molecular formula was deduced as
C26H28O14. The molecular weight of
compound was found to be molecular weight:
564 amu, from FAB-MS. The UV spectrum
showed absorption at 218, 225, 305 and 315.
Its IR spectrum displayed a characteristic
band of chelated carbonyl group at 1660 cm-1.
The 13C-NMR spectrum of compound showed
Determination of structure of new anthraquinone from the flowers of Marigold from Temperate zone of Garhwal Himalaya
Kumar & Jagwan
the presence of 26 carbon atoms. The
assignment of all proton and carbon were
achieved by 1H-1H-HOMO (COSY) and
inverse 13C-NMR data, which showed the
anthraquinone skeleton of compound. The
anomeric proton of compound exhibit doublet
at δ 5.8(J=7.2 Hz) anomeric proton of β-
linked D-glucose. A doublet at δ 4.62(J=2.0
Hz) were assigned for α-linked xylose. The
downfield signal at δ 142.2, 142.8, 151.2,
158.1 were assigned for substitution at C-1,
C-2, C-6 and C-8 carbon atoms, C-8 found to
be glycosilated. Thus on the basis of above
data PT-1 was identified as Anthraquinone
1,6-dihydroxy 2-methyl 8-O-β-D-
glucopyranosyl (1→6)-α-L-xylopyranoside
(Figure-1). It was further confirmed by
comparison of its data with that of reported
compound (Thomson 1971 and Wijnsma
1986).
Acknowledgments
Our thanks are due to Professor Ivano
Morelli, Department of Pharmaceutical
Science, Bonanno, 33, Pisa-Italy for recording
NMR and MS. Dr. S.P. Joshi, Reader,
Department of Botany, D.A.V. (P.G.)
College, Dehradun for plant identification and
providing necessary facilities for dyeing of
fabrics.
Figure-1
OH O
CH2
HO O
HO O
OH O
OH O CH3
OH
HO
O
24
  
Volume I Number 2 2010 [23-25]
[ISSN 0975 - 6272] Kumar & Jagwan

References Prakash Rao, Ramesh E.V.S. and S. Putlano

(2000). J. Med. Arom. Plants, 22,
Chawdhury, A.R. (2001). J. of Essential Oil
258-259.
Bearing Plants, 4(1), 9-12.
Thomson, R.H. (1971). Naturally Occurring
Gaur, R.D. (1999). Flora of District Garhwal.
Quinones, Chapman and Hall,
Trans Media, Srinagar Garhwal, 592.
London.
Potter, L., and J. Thomas (1995): J. of
Wijnsma, R. and R. Verpoorte (1986). Prog.
Essential Oil Research, 7, 347.
Chem. Org. Nat. Prod., 49-79.

Determination of structure of new anthraquinone from the flowers of Marigold from Temperate zone of Garhwal Himalaya
25