NATURAL ESSENTIAL OILS

FRAGRANCES AND FLAVOURS

eoFiTff!tj'''.
iloF\

Dr. Akhil Baruah

Dr. Subhan C. Nath

Aavishkar Publishers, Distributors

]aipur 302 003 (Rai.) India
 Wrro MemcoLD (TecrTES MINUTA L.) :
CuruvATroN TBcrrNolocy Ar\D EssBNTTAL
On CovrposrrroN
K.V. SyeuesuNDAR AND B.R. Repswene Reo

INTRODUCTION
Wild/South American/South Africar/Mexican marigold or muster John-Henry or
Khaki weed or stinking roger (Tagetes minuta L. synonym Tagetes glandulifera Schrank,
Eamily: futeraceae) (Fig. l) is an erect, profusely flowering, annual aromatic plant of
South American origin that spread to other regions of the world as a weed. The species
is reported from fugentina, Australia, Bolivia, Brazil, Chile, France, India, Kenya, Nigeria,
Paraguay, Peru, South Africa and Uruguay. fugentina, Australia, Brazil, France, Kenya and
South Africa are the principal producers and exporters of T minuta essential oil. In India,
it got naturalized in Himachal Pradesh, Uttar Pradesh, Uttarakhand and Jammu and
Kashmir states between 1000-2500 m altitudes with a production of 3-5 tonnes of
essential oil, a maior proportion of which comes from Himachal Pradesh. The wild
growing plants in Jammu and Kashmir, Uttarakhand and Uttar Pradesh are also utilized
for essential oil production (Singh et al. 1995b, 2003, Kumar et al. 1998). Commercial
cultivation has been started in Himachal Pradesh and north Indian plains. It can be grown
in south India (Kaul et al. 1998, 2005, Prakasa Rao e/ al. 1999,2000a, b, Singh 200I).
Compared to other aromatic crops such as mifrts, aromatic grasses, spices, rose-scented
geranium etc. less research work was carried out on this species in India.
TN(ONOMY OF WILD MARIGOLD
The genus Tageteswas narned after the Etruscan deity "Thgetes" who revealed the
art of water divining essential for farming. The genus Tagetes has around 56 annual and
perennial species distributed in the tropics and warmer parts of America. The important
Wrro Menrcoro (Teezrns MrNurA L.) t CurrrverroN TpcrrNol,ocy 229

species of the genus are: T. arborea, T billora, T erecta (African marigold), T elongata,
T lucida, T mendocina, T minuta, T patula (French marigold), T parytand 7l signatasyn.
T tenuifotia. T erectaL., T minutaL., T patulal. and T signataBartl. occurin India. Z
minuta is an erect, branched, 1-2 m tall, annual, highly aromatic herb. Altemate or
opposite, 50-170 mm long, glossy-green, pinnatisect leaves bear 4-6 pairs of pinnae.
Leaflets are 20-50 mm long, linear or lanceolate with serrate margins. Leaf undersurface,
involucre bracts and stems bear small, punctuate, multi-cellular glands that emit liquorice-
like aroma when ruptured. Small, corymbose flowers, 10-18 mm long appear in clustered
panicled branches. Flower heads are surrounded by involucre bracts that are united into
a tube with five short, free yellowish-green lobes. Ray florets are 2-4 in number, white to
pale yellow coloured, obcordate in shape. Disc florets are 3-6 in number, deep yellow
coloured with small lobes. Brown coloured, linear-lanceolate achenes are 6-12 mm in
length with golden yellow hairs. Pappus is 2-4 mm long. Retrosely semrlate, 0-2 awns are
l-3 mm long. The achenes weigh 0.8-l.l g per 1000. T minuta is a long day, cross-
pollinated plant with 2n = 24 or 48 chromosomes. Leaves, flowers, achenes are the chief
parts containing the essential oil of commerce. A high flower and leaf to stem ratio is
desirable for obtaining high oil yield (Singh et al.l995b, 2003, Kumar et al. 1998).

Fig. l. Tagetes minuta flowering plants

CULTIVATION TECHNOLOGY
The crop is suitable for cultivation in the plains as well as on the hills as a monocrop
or intercrop in orchards/foresVmedicinaVaromatic trees or widely spaced crops such as
rose-scented geranium. It is amenable for integration with traditional agricultural or
aromatic crops in suitable crop rotations. CSIR-CIMAP, Lucknow has released a high
lelding variety Vanphool along with its agro-technology (Ram et aL.1998, 1999, Prakasa
Rao etal.l999, 2000a, Singh 2001) and is popularizing its large scale cultivation in different
230 K.V. SveuesuNDAR AND B.R. Repswene Reo

parts of India (Kumar et al. 1999). Accessions collected from various geographical regions
of India showed only 70/o polymorphism and 95-100%o similarity (Darokar et aL.2000). It
is suitable for cultivation in a wide range of soils from sandy loams to clay loams either
as kharifor as rabi crop. Well-drained, fertile soils with 4.5-8.0 pH are best suited. Cool
temperatures induce germination and high temperatures encourage profuse vegetative
growth and flowering. Direct seeding (2.0-2.5 kg seeds/ha) or transplanting of 100-200
mm Iong 30-60 days old seedlings (0.50-0.75 kg seeds/ha for raising the nursery) with 300-
600 x 150-300 mm spacing is practiced. Closer spacing of 300 x 150-300 mm for direct
broadcasted or line sown seeded crop and wider spacing of 450-600 x 300 mm for
transplanted crop is recommended. In less fertile soils closer spacing of 300 x 300 mm
is suggested. Seeds germinate in 7-10 days (Kumar et a1.2008). Young seedlings are
susceptible to weed competition. Trnro to three manual weeding operations are necessary
until the crop establishes. Fully grown plants can smother the weeds. Nipping apical buds
50-60 days after seed sowing or 30-45 days after transplanting promotes growth of the
branches and produces a crop canopy with higher proportion of leaves and flowers. The
crop can withstand short periods of moisture shortage. Three to five inigations of 25-30
mm depth orirrigation at 0.5 IW: CPE ratio (Singh 2001) is sufficient to raise a good crop.
The crop responds to application of 20-30 tonnes of FYM, 100-200 kg N, 60 kg P2Os, 60
kg IqO per hectare. Phosphorus and potassium are applied basally, while nitrogen is
applied in 3 equal splits at planting, active vegetative and flower bud initiation stages. The
crop is occasionally affected by wilt (caused by Sclerotiana sclerotium, seed treatment
with Thiram is suggested), collar rot (caused by Sclerotium rolfsii, seed treatment with
Thiram is recommended), litfle leaf (caused by phytoplasma, spraying with Streptomycin
is useful) and marigold mosaic (caused by virus, infected plats are bumt) diseases. Wild
marigold is harvested manuallywith sickles during full flowering (Prakasa Rao et a1.2000a,
Singh et al.l995a, b, Singh et a1.2006b) (4-7 months duration) or seed setting (Thappa
etal.l993, Singh etal.2006a) stages,200-300 mm above the ground level. Crop duration
is short (main 100-t l0 days, ratoon 30-60 days) in south India irrespective of whether the
crop is planted in rainy (July/September) or winter (December) seasons (Prakasa Rao el
aI.2000a, Singh 2001). Crop duration can be modified in Himachal Pradesh byplanting
the crop early (long duration) or late (short duration with high leaf and flower to stem
ratio) (Ramesh & Singh 2008). Oil content is less at pre-flowering (0.2-0.25%) relative to
full flowering (0.4-0.5y0) stage. Winter harvested ratoon (regenerated) crop affords higher
oil recoveries (0.7o/o). One or two ratoon crops are possible in India. Four cropping
systems have been developed for temperate climate of Himachal Pradesh hills namely,
single harvest main crop (July-November), double harvest (July-January) autumn crop
with winter ratoon, triple harvest (March-January) summer crop with autumn first ratoon
and winter second ratoon and short duration autumn-winter crop (September-December)
which is suitable for north Indian plains also. Biomass and essential oil yields range from
20-30 tonnes and 50-75 kg/ha, respectively with mean oil recoveries ranging from 0.20-
0.35%o in the main crop. Winter harvested ratoon crops give higher recoveries (Singh e/
al. 1995b, 2003, Kumar et al. 1998). With an oil price of Rs. 1500-20001kg, the gross retums
range from Rs. 75000-150000/ha/year. Higher oil yields (>80 k/ha) were recorded when
more than one harvestwas taken from the crop (hakasa Rao e/ aL.2000a, Singh 2001,
Singh et aL.2003).
Wrlo lVlenrcolo (Tecrrz,s MrNwA L.) r Cur-rrverroN TBctrxot.ocy 237

DISTILLATION AND ISOLATION OF AROMA CHEMICALS

Freshly harvested or l-4 days shade dried flowering shoot biomass is distilled for
2 t/z to 3 % hours in made of mild steel (Fig. 2). Steam
batch-ty1pe distillation units
distillation at 40 psi takes lesser time while field distillation (water-cum steam distillation)
takes longer tirne (Singh et al. 1995b, 2003, Kumar et al. 1998). Distillation under vacuum
(150-225 mm Hg) yields an oil rich in oxygenated components with longer shelf life and
better organoleptic pr{brties (Kiran Babu & Kaul 2007). Dihydrotagetone has been
isolated from the oil and synthesized chemically. It can be further converted into valuable
aromatic alcohols or furanones (Joshi et aL.2005, Sinha et aL.2007).

Fig. 2. Distillation unit with cohobation facility and double condenser system
STOMGE OF OIL
Wild marigold oil decanted from the receiver of the distillation unit is allowed to
stand for 12-24 hours to separate small amounts of water present in the oil. The oil is
treated with anhydrous sodium sulphate to make it moisture free. The oil is filtered to
remove extraneous impurities. The oil is preferably stored in amber-coloured glass or
aluminum or stainless steel containers in a cool place away from direct sun light and
highly humid conditions after filling the containers up to the brim without any air gap and
tightly stoppering those (Singh et a1.,1995b, 2003). For long term storage, it is preferable
to store the oil under refrigeration or in a cold storage facility (Prakasa Rao e/ a1.,2000b).
USES OF WILD MARIGOLD
Marigolds with their attractive flowers (used in social and religious functions) and
luxuriant foliage are excellent omarnental plants grown extensively in pubtic parks,
gardens and in homes as potted or bedded plants. The essential oil is used in the
232 K.V. SveuesuNDAR AND B.R. Repsvene Reo

perfumery pharmaceutical, food flavouring and agricultural industries. The oil and
absolute are employed in compounding high grade perfumes and for flavouring cola/
alcoholic beverages, frozen dairy desserts, candy, baked goods, gelatins, puddings and
condiments. Dried Ieaves or their decoction are used as medicinal tea and for culinary
purpose imparting aroma to soups, food and vegetable preparations. Ketones of the
essential oil are utilized for synthesizing high grade aroma chemicals. Joshi et al. (2005)
synthesized allryl (minty, spicy, fruity odour) and aryl (woody or sweet aroma) alcoholic
compounds from dihydrotagetone (which has been synthesized by many researchers)
using attqfVaryl metal halides. Sinha et al. (2007) synthesized 5-isobutyl-3-methyl-4,5-
dihydro-2(3H)-furanone, an analogue of whisl<y lactone from dihydrotagetone. These
compounds find application in perfumery and flavouring industries. Volatile oil is
tranquilizing, hlpotensive, spasmolytic and antiinflammatory. The boiled leaves and oil
e:fiibit broncho-dilatory, antimicrobial and insecticidal properties (Chandhoke & Ghatak
1969 Sa:rena & Srivastava 1973, Razdan et al. 1986). The plant is diuretic, digestive,
purgative, rela<es spasms, destroys intestinal parasites and is effective against pathogenic
,microorganisms, cold, diarrhea and liver disorders. The plant as a companion crop
controls nematodes, slugs and at times suppresses weeds. Allelopathic effects of essential

Wld rnarigold (Tagetes minuta'1

TraditionaUmedicinal I oirtilt"o biomass

uses, phytochemicals

Fuel for lVermicompostl Phyto- Powder for

distillation unit I compost I chemicals lncense sticks,
as pesticide
Fractional disti lation
I

,t
AryUalkyl alcohols,
R tr*-l Dihydrotagetone
furanones
Water-solube oil

Pesticide Pharmaceutical ind ustry

industry

Figure 3. Uses of different products of wild marigold

Wrr.o Menrcoro (Teerrr,s MINUTA L.) t Currrverrox Trcr+Nor.ocy ?33

oil and plant extracts have been reported. Dried powder can be used to control weeds
in rice (Batish etal.2007). Oil and its constituents have insecticidal, antibacterial, antifungal,
antiviral and mosquito larvicidal activities. Ocimene and ocimenones in the oil have
antifungal activity against Sclerotium cepivontm, Altemaria solani and,phytopathogens of
potato, tomato and brinial (Singh et al. 1995b, 2003, Kumar et al. 1998). The uses of wild
marigold products are surnmarized in Fig. 3. In sensitive individuals, essential oil may
cause contact dermatitis, such individuals should take precautions while handling the oil.
PHYSICO.CHEMICAL PROPERTIES OF THE ESSENTI,AL OIL
The physico-chemical characteristics of Indian wild marigold essential oil are
presented in Table l. Bureau of Indian Standards (BIS) is yet to come out with its
standards for wild marigold oil.
TABLE I
Physico-chemical characteristics of wild marigold essential oil
Physicechemical property Value
Appearance Mobile clear liquid
Colour Pale yellow to dark yellow or orange or reddish-
yellow
Odour Green fruity or powerful peculiar, somewhat
disagreeable odour, woody, reminiscent of rancid
butter with light buming note
Refractive index 1.48s0-1.s896
Specific gravity 0.8405-0.9440
Optical rotation + lo to + 5.430
Ester value 16.54-53.69
Ester value after acetylation 35.86-134.87
Carbonyl content (calculated as 27.08-49.30
dihydrotagetone 7o)
Solubility in alcohol 0.9-1.5 volumes of 8070 or 90% alcohol
(Source: Handa etal.1963, Gupta & Bhandari 1975, Baslas & Singh 1981, Kaul etal.1998,
Chowdhury 2001, Singh et aL.2003, Kiran Babu & Kaul 2007)
CHEMICAL COMPOSITION OF THE ESSENTI,AL OIL
WiId marigold flowers and Ieaves contain flavonoids, pollphenols, polysaccharides
and other phytochemicals. The roots contain thiophenes {5-(4-hydrory-l-butenyl)-z,2'-
bithienyl, 5-(4acetoxy-l-butenyl)-2,2'-bithenyl, S-(3-buten-l -ynyl)-2,2'-bithenyl and 2,2':5'2"-
trithenyl). In addition to essential oil, small quantity of absolute is made in other counries.
The earliest record of Indian essential oil composition is that of Chopra etal. (1963) and
Handa et al. (1963) who distilled the oil form air dried witd growing (in Simta) Tagetes
minuta plants in full bloom. They described the oil as sweet smelling having l7.3Vo
aromadendrene, l5.4Vo tagetone, 15.4% phenylethyl alcohol, 15.0% ocimene, 7.98b
salicylaldehyde, S.SVophenyl acetaldehyde, 3.5% 2-hexen-l-a1,2.2% eudesmol, 1.8% linalyl
acetate and 5.070 unidentified carbonyl compound. Aromadendrene (23.9%) rich oil was
2Y K.V. Sveuestnroen enro B.R. RepswAne Reo

reported by Baslas & Singh (1981) also that contained limonene (9.6%o), ocimene (13.1%),
p-myrcene (16.4%), tagetone (15.1%o), d-carvone (6.1%o), linalool (3.6%o) and linaly'l acetate
(4.3%) as main components. Eighty (80) constituents have so far been identified through
GC, GC-MS and other techniques by researchers in Indian essential oil samples with (Z)-
p-ocimene, dihydrotagetone, tagetone (Z & E) and ocimenone or tagetenone (Z & E) as
the maior compounds. The range of percentages of 80 essential oil compounds reported
from several Indian locations is presented in Tlable 2. Structures of important essential
oil constituents are depicted in Fig. 4.
TABLE 2
Constituents and their. percentages reported from several Indian locations
in wild marigold essential oils
Name of the compound Area Yo

l-Fenten-3-ol 0.00-5.10
(E)-2-Hexenal 0.00-3.50
Ethyl 2-methyl butyrate 0.00-0.10
(E)-2-Hexenol 0.00-0.30
Isoamyl acetate 0.10-0.20
Ethyl valerate 0.10-0.8
Propylbutyrate T
2-methyl ethyl propionate 0.00-0.33
2-methyl ethyl butyrate 0.00-1.65
2-methyl bu$ acetate 0.00-0.23
2,3,5-Tiimehtyl furan 0.00-r.89
Octanal 0.00-0.62
cr-Pinene 0.r0-0.80
Sabinene 0.10-2.60

ftPinene 0.00-0.60
Myrcene 0.10-16.4
iso-Limonene 0.00-4.63
o-Phellandrene 0.10-0,20
Phenyl acetaldehyde 0.00-3.50
pCymene T-2.10
Salicylaldehyde 0.00-7.9
Limonene 0.20-47.6
p-Phellandrene 0.00-1.04

Contd...
Wrr.o Menrcoro (Teenrns MrNwA L.) t cur-rrverroN TBcrrNolocy 23s

...Contd.

Name of the compound Area Yo

(Z)-p-ocimene 1.00-50.00
Dihydrotagetone 3.90-78.r0
Octanol 0.10-0.20
7-Terpinene 0.80-0.10
Artemisia ketones 0.30-0.50
2-Nonanone 0.00-2.68
Terpinolene 0.10-0.50
Phenyl ethyl alcohol 0.10-15.40
Linalool 0.r0-4.60
o-Thujone 0.10-0.20
B-Thujone 0.r0-0.89
Isobomeol 0.20-0.60
(E)-tagetone 0.40-2r.23
(4-tagetone r.90-37.10
Bomeol 0.r0-0.80
Menthol 0.00-0.93
cr-Terpineol 0.r0-1.35
Terpinen-4-ol 0.30-0:40
y-Terpineol 0.00-1.20
Decenal 0.00-0.28
d-Carvone 0.00-6.10
Carvotanacetone 0.00-r.37
(}-ocimenone [ (Z)tagetenone ] 0.90-40.00
Methyl thymol 0.00-1.20
(E)-ocimenone [(E)-tagetenone I 0.50-r4.53
Geraniol 1.70-52.00
Linalyl acetate 0.30-4.30
Piperitone 0.10-1.30
Citral 0.00-2.27
Thymol 0.00-0.50
Bomyl acetate 0.r0-1.30
Carvacrol 0.20-3.72
(r)-Carryl acetate 0.40-3.20

Contd...
236 K.V. SveuesuNDAR AND B.R. RepsVene Reo

...Contd.

Name of the compound fuea %

Eugenol 0.00-0.60
Gemyl acetate 0.20-1.70
Methyl eugenol 0.10-0.60
$,'EIemene 0.10-0.69
beta -Cubebene 0.00-3.75
p{aryophyllene 0.I0-t 1.07
iso-Eugenol 0.00-2.69
y-Elemene 0.10-0.20
Aromadendrene 0.00-23.90
a-Humulene 0.30-0.50
p-lonone 0.00-3.06
Germacrene-d 0.10-0.20
$Bisabolene 0.00-2.45
&tadinene 0.10-1.20
(E)-nerolidol 0.00-0.93
Spathulenol 0.10-1.50
Caryophyllene oxide 0.10-1.50
B-Eudesmol 0.10-2.20
s-Cadinol 0.20-0.30
(i,4-Farnesol 0.10-0.40
(4^E)-Hamesol 0.10-0.30
3, 7-dimethyloct- I -en-6-one T
3, 7-dimethyl-5-hydro4yoct- I -en-6-one T
3, 7-dimethyloct- I, 7-dien-6-one T
Aliphatic compounds 0.40-33.00
fuomatic compounds T-5.60
Monoterpene hydrocarbons 2.50-124.47
oxygenated mono terpenes r 1.30-275.83
Sesquiterpenes 0.80-43.96
oxygenate d sesquiterpenes 0.70-7.13
Phenols and phenolic ethers 0.70-12.51

T: traces <0.10
(Source: Baslas & Singh 1981, Singh et al. 1992, Thappa et al. 1993, Garg & Mehta 1998,
Prakasa Rao et a1.1999, Chowdhury 2001, Singh 2001, Singh & Singh 2002, Kaul et al.1998,
2005, Raieswara Rao e/ al. 2006, Singh et a1.2006b, Kiran Babu & Kaul 2007)
Wrro Menrcor,o lTeerrcs MIN:TA L.) t CurrrverroN Tsct+Not,ocy 237

4f4
I

O(
A.,
Limonene Myrcene (Z)-B-Ocimene Dihydrotagetone Linalool (Z)-Tagetone

5
A
@)-Tagetone (Z)-Ocimenone, @)-Ocimenone Geraniol Canrone

Fig. 4. Structures of maior compounds reported from Tbgetes mjnuta oil

One hundred and eighty five (185) constituents identified in wild marigold essential
oils from different countries are listed in llable 3.
FACTORS REGULATING THE ESSENTI,AL OIL COMPOSITION
Chemotlpes: Tagetone and tran*caryophyllene rich chemotype was reported by
Chowdhury & Khan (2000) and Chowdhury (2001) from flowering plants growing wild
in Kumaon region of Uttarakhand. Other compounds found in this chemotlpe were: p-
238 K.V. SvauesuNDAR AND B.R. Repswene Reo

bisabolene, carvotanacetone, carvacrol, citral, B-cubebene, pclirnene, dihydrotagetone,

isoeugenol, p-ionone,linalyl acetate,linalool, isolimonene, ethyl-n-heptyl ketone, B-myrcene,
menthol, nerolidol, 2-nonanone, p-ocimene, ocimenone, 1-penten-3-ol, phenyl
acetaldehyde, o-pinene, spathulenol, cr-terpineol and y-terpineol. Aromadendrene rich
(17.3-23.990) chemob/pe was recorded by Handa et al. (1963) and Baslas & Singh (1981).
Occurrence of chemotlpes with abundance in tagete derivatives (up to 8090) or in
terpene derivatives (up to 760/o) has been observed in Madagascar. Other chemotlpes
(ocimene, ocimenone, dihydrotagetone etc. rich plants) have been identified in Turkey,
Argentina and other countries.
TABLE 3
Compounds identified in wild marigold essential oil produced
in different countries
Grouped components Compounds identified
Aldehydes (1a) (E)-2-Hexenal, 3-isobutyl-3-methyl-2-furancarboxaldehyde, 2-
methylpropanal, 2-methylbutanal, 3-methylbutanal,
acetaldehyde, phenyl acetaldehyde, decenal, geranial, neral,
heptanal, octanal, p-anisaldedyde, salicylaldehyde
Acids (l) Valeric acid
Alcohols (32) I -Penten-3-ol , (E)-2-hexenol, 2-phenylethyl alcohol, octanol,
oct-l-en-3-ol, non-l-en-3-ol, bomeol, c/scarveol, citronellol,
geraniol, guaiol, isobomeol, ledol, linalool, verbenol, menthol,
terpinen- l -ol, terpinen -4-ol, trans-p-mentha-2-en- l -ol,
' viridifl orol, cr-cadinol, cr-terpineol, y-terpine ol, transffterpineol,
alchenenotriol, (E)-nerolidol, (E,E)-famesol, (Z,Z)-famesol,
spathulenol, u-cadinol, B-eudesmol, globulol
Esters (26) Amyl acetate, 2-methyl butyl acetate, 3-methyl butyl acetate, 2-
methyl ethyl butyrate, 2-methylpropyl butanoate, ethyl-2-methyl
butyrate, 2-methyl ethyl propionate, methyl 3-methylbut-2-
enoate, tran*canryl acetate, crs-carvyl acetate, 2-phenyl ethyl
tiglate, bomyl acetate, decyl acetate, pentyl acetate, 3-hexenyl
acetate, hexyl acetate, ethyl valerate, geranyl acetate, isoamyl
acetate, isobomyl acetate, linayl acetate, methyl citronellate,
neryl acetate, phenyl butyrate, propyl butyrate, pentyl 3-
methylbutanoate !

Ethers (3) 1,8-Cineole, 2,3,5-trimehtyl frrran, cr-terthienyl I

i
Hydrocarbons (50) pCymene, (Z)-p-ocimene, allo-ocim ene, neoallo-ocimene crs
cis-allo-ocimene, cis -transallo-ocimene, 2-isobutyl norborane, I

3, 4-dime thyl 2,4,6, -triene, o-thui ene, camphene, naphthalgne,

pentadecane, p-mentha-I,8-triene, sabinene, tridecane,
teffadecane, toluene, cr-phellandrene, ftphellandrene, o-pinene,

Contd...
Wrrr Menrcor,o (Teerrr,s MTNUTA L.) t Cur-rrverrou'fectrNorocy ?39

...Contd.

Grouped components Compounds identified

fpinene, pterpinene, crssabinene hydrate, Iimonene, mpcene,
isoJimonene, santene, terpinolene, A-3-carene, p-bisabolene,
p-elemene, y-elemene, &elemene, a-gurj unene, c[-muurolene,
aromadendrene,, bicylcogermacrene, p-patchoulene, p-
caryophyllene, iso-caryophyllene, cl-humulene, cr-cadinene, 1"
cadinene, &cadinene, gernacrene-B, gernacrene-D, tan*p-
famesen e, transa-bergamotene, valencene, longifolene
Ketones (35) 2(10)-Pinen-4-one, butenone, butanone, 4-methyl pentanone,
4-methyl-2-pentanone, oct-l-efl-3-one, non-l-en-3-one, p-
ionone, 6-methyl-yionone, acetone, artemisia ketone, camphor,
menthone, cisdihydrocaryone, carvone, c/spananone, (Z)-
jasmone, dihydrotagetone, (E)-ocimenone [(E)-tagetenone l,
(E)-tagetone, (Z)-ocimenone [ (Z)-tagetenone l, (Z)-tagetone
,dehydroelshotzia ketone, dimethyl octenone, iso-piperitone,
piperitone, p-menth-4-en-2-one, p-menth-4-en-3-one,
verbenone, cr-thujone, p-thuione, elshotzia ketone, 3,7-
dimethyloct- I -en-6-one, 3, 7-dimethyl-5-hydroxyoct- I -en-6-one,
3, 7-dimethyloct- l, 7-dien-6-one
Oxides (6) Caryophyllene oxide, crsp-ocimene epoxide, crilinalool oxide,
translinalool oxi de, (Z) -epoxy o ci mene, (E) -is o-safrole
Phenols (l l) Carvacrol, (E)-anethole, eugenol, isoeugenol, eugenyl acetate,
methyl carvacrol, methyl chavicol, methyl eugenol, methyl
thpnol, thymol, thymolhydroquinone dimethyl ether
Sulphur compounds (7) 2,2',5',2u-Terthiophene, 5-(but-3-en-I-ynyl)-2,2',-bithiophene, 5-
(but-3-en- t -ynyl)-5'-methyl-z,2' ,-bithiophene, S-acetoxy- I -
butynyl)-2,2',5',2u-terthiophene,S-methyl-z,2',5',2"-terthiophene,
S-methyl -2,2' -2 -te:rthiophene, cr-p-dimethylstyrene
Altitude: Essential oil from high altitude areas is rich in ketone constituents and
the oil from Uttar Pradesh and funiab plains has low olfactory value (Singh et al.l995b).
Planting and harvesting season: Wild marigold can be planted in different
seasons depending on the number of harvests desired and location of planting (hills or
plains). In Kamataka plains (Bangalore, 930 m altitude) 40 days old seedlings transplanted
in the third week of July were harvested in the fourth week of September. The main crop
produced an essential oil with 3.3% limonene, 30.370 crb-p-ocime.,L, 9.1yo dihydrotagetone,
19.390 crstagetone and 2l.7Vo cisocimenone. When the crop was transplanted in the first
fortnight of December and harvested in the second week of February, the composition
of the main crop oil was: 4.lo/o limonene,20.2Vo cisp-ocimene, 20.7% dihydrotagetone,
19.60/o crstagetone and 8.5%o criocimenone (Singh, 2001). Dihydrotagetone and crs
ocimenone exhibited trend reversals. In Himachal Pradesh, June seeded October/
2N K.V. SveuasuNDAR AND B.R. Repsvene Reo

November (autumn) harvested (single or double harvest) crop gave an qil with 35-41% Ir
ocimene, 34-38% dihydrotagetone, 16-200/o (E & Z)-tagetones and l7-/2Vo (E & Z)- 6l
ocimenones. When the crop was seeded in March and harvested in Junef the essential 5l
oil of the main or first harvest crop had l7-2lVo ocimene,l8-23otb dihydrotagetone, 28-32% ta
(E & Z)-tagetones and 26-29% (E & Z)-ocimenones. A short duration single harvest crop n
planted in early September and harvested in late Decemberyielded an essential oil having o(
12-15% ocimene, l7-2lVo dihydrotagetone, l8-22o/o (E & Z)-tagetones and 42-48o/o (E&Z)- m
ocimenones. It is therefore possible to regulate the oil composition by varying planting fir
and harvesting dates (Singh et a1.2003). di
Plant ontogeny: Harvesting the herb at pre-flowering stage affords lower oil rh
recovery compared to harvesting it at full bloom stage (Singh et al. 1995a, Kumar et al. sti
1998, Prakasa Rao et a1.2000a). At vegetative stage, the principal constituent of the oil was ta
tagetone. With the advancement of plant age, dihydrotagetone percentage increased with ;u
simultaneous decrease in tagetone and ocimenone concentrations. At full bloom the pr
relative percentages of the three important ketones were: 40-55Vo dihydrotagetone, 15- (n
20Vo tagetone and 15-30%o ocimenone at different locations ranging in altitudes from I 200-
(s
1800m in Himachal Pradesh. In Uttarakhand (300 m altitude) the relative concentrations fl(
of these three ketones were 71.7%, 13.9%0, 7.2o/o, respectively (Singh et al. 1995b). The (l
essential oil yield increased (0.33-l .25Vo) while dihydrotagetone content decreased from au
early flower bud (48.1%) to fruit maturation (ll.99o) stages. The percentages of (Z)-F- tr
ocimene (16.6 to 35.370) ,(Z)-and (E)tagetenones (8.1 to26.4-32.5%o) increased from early
flower bud to immature fruit formation stages possibly through biogenetic conversion of C
dihydrotagetone. (E)-tagetone (0.0-6.10/0) and (Z)-tagetone (18.6-27.1%) did not exhibit
specific trends (Thappa et al., 1993). Enhancements in oil (0.20-0.28%o) limonene (5.2- c
21.1%), dihydrotagetone (9.0-36.070), (Z)-ta$etone (24.9-29.470) and reductions in (E)-
U
tagetone (4-4-l.9Vo), (E)-tagetenone (10.0-0.9%) and (Z)-tagetenone (37.7-4.9Vo)
concentrations were recorded from pre- to post-flowering growth stages by Singh et al. G
(2006) in Lucknow. In south India, flower initiation and full bloom stages recorded higher D
oil content of L4Vo (dry weight basis) relative to vegetative ( I .0%) and seed setting (1.2%) (t
stages. Plants at vegetative stage registered maximum dihydrotagetone (54.370), a
contrasting observation compared to Himachal Pradesh hill conditions. The major 0
constituents at flower initiation stage were: 16.690 criB-ocimene, 21.9% dihydrotagetone, 0
23.9% critagetone, 9.970 cistagetenone arrd 4.2Vo tran*tagetenone. At full bloom the
_q
percentages of these constituents were: l4.4Vo cisp-ocimene, 30.370 dihydrotagetone,
(s
l3.7Vo critagetone and 7 .0o/o critagetenone. At seed setting the relative contents of these
K
compounds were: 23.5V0 crsp-ocimene, 29.0%o dihydrotagetone, 13.590 crstagetenone,
5.3% crstagetenone and 6.8% transtagetenone (Prakasa Rao e/ aI.2000a).
Plant parts: Flowers and leaves are the principal parts containing the oil. Fruits h
(0.590) also possess oil. Stems yield traces of oil (Singh et a1.2006) the composition of s,
G
which has not been o<amined. The composition of different parts is presented in I'lable
4. Leaf oil is rich in dihydrotagetone (>70.0%o) and flower oil in (Z)-F-ocimene (Singh e/
h
n
al.l995a), Iimonene and (Z)-tagetone (Singh et a1.,2006a). Bansal et al. (1999) analyzed
2
Ieaf oils at different growth stages (vegetative, full flowering and seed maturity) under
h
Wn-o Menrcolo (Taerru,s MINUTA L.) t CurrrvetroN TpcrrNol.ocy 241

Lucknow conditions. The oils contained 3.4-4.470limonene, 3.6-8.lVo (Z)-9-ocimene, 13.6-

6I.890 dihydrotagetone (content increased from vegetative to seed maturity stages), 1.5-
5.9Vo (E)-tagetone, I 1.9-25.3% (Z)tagetone, 1.3-9.5%o (E)+agetenone and 0.5-l 7 .6Vo (Z)-
tagetenone (the concentrations of tagetones and tagetenones declined with plant age).
The flower oil at full flowering stage was rich in dihydrotagetone (44.lVo) and (Z)-f-
ocimene (9.4Vo). The principal components of whole plant oils at full flowering and seed
maturity stages were: dihydrotagetone (32.0-48.70lo) and (Z)-tagetone (15.0-16.70/o). These
findings differ from other Indian studies where leaves and flower oils were rich in
dihydrotagetone and (Z)-F-ocimene, respectively. Singh et al. (2006) critically examined
the composition of leaf and flower oils at pre-flowetirg, 50Vo, 10070 and post- flowering
stages. The leaf essential oil contents limonene (5.8-1.570), (E)-tagetone (3.4-0.8Vo), (Z)-
tagetone (25.4-5.3o/o), (E)-tagetenone (9.6-0.20/o) and (Z)-tagetenone (40.0-0.1%o) declined
and those of (Z)-F-ocimene (2.6-6.3Vo) and dihydrotagetone (7.0-77.1%o) increased from
pre- to post-flowering stages. In the case of flower oils, the concentrations of limonene
(4.2-47 .60/o), (Z)-tagetone (10.5-23.80/o) showed rising trend whereas those of (Z)-F-ocimene
(50.0-13.4 to nilgo), (E)+agetenone (8.9-2.3Vo) exhibited decreasing trend with progress in
flowering. Dihydrotagetone increased (3.6-27 .60/o) then declined (8.3y0), while (Z)-tagetone
(10.5-0.8%o) and (Z)-tagetenone (18.7-1.4%o) decreased then increased (23.8% tagetone
and l0.lVo tagetenone) with progression of flowering. The limonene content of 47.60/oin
the flower oil at post-flowering stage is the highest percentage reported in T minuta oil.
TABLE 4
Composition (%) of essential oils of different plant parts of wild marigold
Compound Leaf Flower Fruit Herb
Limonene 2.3-4.4 2.9-4.1 4.7 3.9-5.1
(Z)-F-Ocimene 3.6-7.1 38.8-47.9 36.8 23.0-42.2
Dihydrotagetone 48.2-78.1 8.8-15.4 r5.5 t4.8-34.4
(E)-Ilagetone 0.8-5.9 0.5-r.9 1.3 0.8-3.1
(Z)-Tagetone 4.0-25.3 6.2-12.9 l7.l I1.5-16.0
(E)-llagetenone 0.2-9.5 5.0-r4.8 7.5 4.9-12.7
(Z)-Ilagetenone 0.1-17.6 5.r-r9.6 3.0 2.3-4.9
(Source: Singh et aI.1992, Garg & Mehta 1998, Prakasa Rao et aI.1999, Bansal et aI.1999,
Kaul et al. 1998, 2005, Raieswara Rao e/ a1.2006)
Ratoon crop(s): One or two ratoon (regenerated crop after the first or second
harvests) crops are possible in wild marigotd. Ratoon (l.9Vo on dry weight basis) crop
gave higher oil recovery than the main (1.0-l .4Vo) crop (Prakasa Rao e/ a|.2000). The
composition of the main or first harvest crops was discussed in the planting and
harvesting season subtitle. In Karnataka, July transplanted October last week harvested
ratoon crop possessed 4.7Vo limonene, 20.2Vo cisp-ocimene, 35.3%o dihydrotagetone,
2l.2Vo cistagetone and 4.6Vo cisocimenone. The December transplanted April first week
harvested ratoon crop of wild marigold contained 3.9%o limonene,2T.lVo c/sp-ocimene,
242 K.V. Sveuesmroen ,lNo B.R. Repsvane Reo

26.7% dihydrotagetone, 20.7% aitagetone and l?.lVo cis-ocimenone (Singh,200t). In the

sarne location, ratoon crop contained higher percentage of cls-p-ocimene (31 .8o/o), cis
tagetone (l6.7Vo) , tran*tagetenone ( t 6. I 7o) and lower content of dihydrotagetone (l0.4Vo)
(Prakasa Rao et a1.2000a). In Himachal Pradesh, Late June sown early January harvested
winter ratoon showed 43-50o/o ocimene ,8-l2Vo dihydrotagetone, l6-20Vo (E & Z)-tagetones
and 25-30V0 (E& Z)-ocimenones. Early March sown mid October cut first ratoon exhibited
oil composition with 39-48o/o ocimene ,18-23Vo dihydrotagetone, l0-l4o/o (E & Z)-tagetones
and 20-25o/o (E & Z)-ocimenones. The second ratoon crop harvested in early January
possessed(l-l2Vo ocimene ,8-l2Vodihydrotagetone, l6-20Vo (E & Z)-tagetones and 25-3170
(E & Z)-ocimenones (Singh et al.2003).
Fertilizer nutrients: Application of nitrogen up to 300 kg/ha did not influence the
content and composition of the oil in south India (Singh 2001). At flower bud initiation
stage, nitrogen application (50-100 kg/ha) significanfly enhanced the concentrations of
cisp-ocimene, crs and tran*tagetenones but, decreased dihydrotagetone content in the
essential oil. Nitrogen had no effect at other stages of plant growth. The oil content
(
declined with nitrogen addition at full bloom stage but was not affected at flower
t
initiation and seed setting stages (Prakasa Rao ef aL.2000a). Spraying of sodium chloride
(
(0.570 aqueous solution) once or twice, enhanced the concentration of dihydrotagetone
but decreased the contents of (Z)-0-ocimene and (Z) and (E)-ocimenones (Prasad et al.
t
(
2002).
t
Inigation: Inigating wild marigold at 0.5 inigation water (lW): cumulative pan a
evaporation (CPE) ratio produced the highest biomass and essential oil yields with no
I
effect on the content and composition of the essential oil in south India (Singh 2001).
T
Storage of biomass: Freshly harvested biomass produces better quality oil on
distillation compared to sun dried or2-3 days stored biomass (Singh et al.l995b, 2003).
T
Method of distillation: Hydrodistilled oil had 3.90/olimonene+p-phellandrene, (
23.0Vo (Z)-F-ocimene, 34.40/o dihydrotagetone + (E)-F-ocimene, 3.lo/o (E)-tagetone, 16.0%
(
(Z)-tagetone, 3.4%o (Z)-tagetenone and 4.990 (E)-tagetenone. The essential oil obtained
through field distillation contained 5.170limonene+p-phellandrene,35.7o/o (Z)-F-ocimene,
23.1o/o dihydrotagetone + (E)-9-ocimene, 0.8%o (E)+agetone, I 1 .570 (Z)-tagetone, 2.3% (Z)-
tagetenone and ll.57o (E){agetenone (Kaul et al., 1998). Raieswara Rao ef al. (2006)
published similar trend with somewhat different percentages of compounds in the two
distillation methods. (Z)-9-ocimene, dihydrotagetone, (E)+agetone, (Z)-tagetone, (Z)-
ocimenone and (E)-ocimenone contents in hydrodistilled and steam distilled methods
were: 13.6,40.8%o; 30.3, l4.8Vo;2.0,0.8Vo;7.1,11.5o/o;5.9,3.7Voand I.8,12.7o/o, respectively.
Kiran Babu & Kaul (2007) distilled air dried biomass of plants in post-flowering stage in
a mini distillation plant. Hydrodistillation under normal temperature and pressure gave
higher recovery of oil (1.5670) with the following composition: 6.070 limonene , 49.3o/o (Z)-
B-ocimene, l2.l7o dihydrotagetone, 3.7V0 (Z)-tagetone, 3.7V0 (Z)-ocimenone, 3.0% (E)-
ocimenone, 55.3%o monoterpene hydrocarbons and 22.9o/o oxygenated monoterpenes.
The oil was reddish-yellow coloured with disagreeable odour and bumt note. When the
sarne material was distilled under vacuum (150-225 mm Hg) the oil recoveries fell to l.l6-
0.9170, but the oil was light yellow to yellow coloured with floral green or pleasant fruity
 wno Merucoro (Teczrrs mtrqnel.) , currrverroN Trcrrxol-ocy 243

odour without the bumt note. The vacuum distilled oil contained 3.8-4.1%o limonene, 23.8-
3l.lVo (Z)-F-ocimene, dihydrotagetone, 7.8-9.5V0 (Z)+agetone, ll.Z-16.9 (Z)-
7.9-30.5o/o
ocimenone,7.5-7.870 (E)-ocimenone,27.5-35.2V0 monoterpene hydrocarbons and S5.3-
65.5%o oxygenated monoterpenes. The oil fractions collected at different times of vacuum
distillation showed considerable variation.
Storage of oil: Freshly distilled oil did not show the presence of ocimene in
Himachal Pradesh. On storing for l5 days, its concentration increased to 2.So/o and on 50
days storage to 55.0%. The dihydrotagetone and ocimenone contents in freshly distilled,
15 and 50 days stored oils were: 42.5Vo,17.2o/o; 40.9o/o,14.60/o and 7.870 ,ll.So/o,respectively
(Singh et al.I995b). In south India, oil stored for 13 weeks under refrigeration exhibited
minimum changes in the composition. Under ambient condition crsB-ocimene and
dihydrotagetone levels increased, concentrations of trans-tagetone and cis-tagetenone
declined (Prakasa Rao e/ aL.2000b).
Water-soluble oil: Wild marigold oil is sparingly soluble in cold (0.ll7o) and hot
(0.15%o) water. However, during distillation of the flowering biomass, a small hydrophilic
fraction (2.0-3.3o/o of the total oil recovered) of the oil escapes into the distillation/
condensate water or hydrosol. Water-soluble oil recovered from the hydrosol using
hexane as the solvent showed the following composition: traces-2.6%o sabinene, I .0-l.4Vo
(Z)-F-ocimene, 3.9-6.8% dihydrotagetone*(E)-F-ocimene, 2.0-4.6Volinalool, G.2-T.gVo (Z)-
tagetone, 1.6-4.30/o (Z)-ocimenone, 10.7-13.070 (E)-ocimenone , 47.5-52.090 geraiol+linalyl
acetate, 0.7-1.370 piperitone, 0.2-l.2Vo caruacrol, 0"4-3 .ZVo transcarqyl acetate and I . -l.ZVo
geranyl acetate (Rajeswara Rao et al.2006).
BIOLOGICAL ACTIVITIES
Antibacterial, antifungal, antiviral, antimosquito, insecticidal, herbicidal and
pharmacological and other biological activities of Tagetes minuta oil, oil constituents and
extracts reported from India and other countries are summarized in Table 5.
CONCLUSIONS
Wild marigold, a branched, highly aromatic, annual herb of South American origin
got naturalized in different parts of the world'as a weed. It is traditionally used in folklore
medicine for treating different ailments and is credited with several pharmacological and
biological activities. The essential oil is traded in the intemational markets for use in
perfumery flavoud.g, pharmaceutical and pesticide industries. As an agricultural crop,
it is a versatile plant that can be grown with ease in high altitude hills as well as in plains
in India. It can be grovrm as a short, single harvest or medium long multi-harve st kharif
or rabi crop. The crop duration can be regulated by changing the planting date/season.
The wild growing and cultivated plants are distilled in steam or hydro-cum-steam
distillation units for isolation of the essential oil that is rich in (Z)-F-ocimene and ketones
dihydrotagetone, (E & Z)-tagetones and (E & Z)-ocimenones or tagetenones. It is possible
to obtain ketones or (Z)-F-ocimene rich oil by distilHng leaves or flowers and by agronomic
manipulation. Dihydrotagetone has been synthesized. Ary/alkyl alcohols and furanones
can be synthesized from this chemical that find application in perfumery and flavouring
industries. The water-soluble oil extracted with hexane from the hydrosol or condensate
2M K.V. SveuasrnrDAR AND B.R. R4Jeswene Reo Wt

Ilable 5 ...(

Pharmacological and biological activities of Tagetes minuta

T.
Activitv Plant component Reference
C,
Broncho-dilation, tranquilizing, anti- Essential oil Chandhoke & ot
inflamimatory, hypotensive, spasmolytic Ghatak 1969, Cr
actMties Razdan et al.1986 bi
Effective against Qtsdercus koenigii Juvenile hormones Saxena & ct
Srivastava 1973
fir
Phototoxicity again st Candida al bi cans Thiophenes from roots Chan et al.1975
af
Mosquito larvicidal activity against E-Ocimenone at 40 ppm Maradufu et al.
Hr
Aedes aegltpti 1978
E<
Antiviral activity Root thiophenes Downum & TA
Towers 1983
Larvicidal activity against Aedes aeglpti l0 ppm of essential oil Green et al.1991 we
third instar larvae Th
Biocidal effect on the larvae and adulis Whole-plant extract Michael et a|.1994 col
of Aedes aeglpti and Anopheles ha
stephensi ma
Anti-fungal activity against Scleroti um Leaf essential oil Zygadlo et a|.1994 VAI
cepivorum, Alternaria solani, sp{
Colle totrich um c occod es cal
Insecticidal activity against Mexican Leaf and flower extracts. Sharlene & Shobha
AC
bean weevil Zabrotes subfasciatus Root extract slow acting 1994
Antimicrobial activity Leaf extract and Tereschuk et al.
flavonoid quercetagetin- 1997 en
7-arbinosyl-galac toside RE
Anophelinocidal activity against Essential oil Basabose et al,
Ba
Anopheles gambiae and,4. funestus 1997
Anxiogenic and antidepressantJike 0.3 mg/kg of essential oil Martijena et al.
effects on rats 1998
Ba
Antifeedant and toxicity effect on Essential oil Rao el a1.2000
second instar larvae of Helicoverpa
armigera Ba
Camation ring and mottle virus Essential oil and its Singh et aI.2002
inhibition constituents (Z)-F- Bal
ocimene and
dihydrotagetone Cer
Toxicity against head lice Pediculus Essential oil Cestari et al.2}04
hutnanus capitis
Control of root-knot nematode Vermicompost of wild Pandey 2005 Ch
Meloidogyne incognita in Artemisia marigold
pallens (davana) Ch

Contd...
 \[|tr-o Merucoro (Tderrrs MrNurA L.) r currrverroN TBcrrNol-ocy 245

...Contd.

Activity Plant component Reference

Toxicity against stored grain insects Essential oil as fumigant Krishna et a1.2005
Calloso bruchus mac ula tes, Sitophilus and contact toxicant
ortzae and Trtbofium castaneum
Control of American Foulbrood Essential oil Eguaras et a1.2005
bacterium Paeni bacillus laruae,
chalkbrood fungu s Ascosphaera apis
and parasitic mite Varroa destructor
affecting honeybees
Herbicidal activity against rice weeds Leaf powder at l-2 Vha Batish et a1.2007
Echinochloa crusgalli and Cyperus
rotundus
water contained geraniol as its chief constituent and was rich in oxygenated components.
This oil can serve as new source for natural geraniol. The factors that influence the oil
composition include chemotypes, altitude, plant ontogeny, plant parts, planting and
harvesting season, agronomic management practices, storage of herb and oil etc. Not
many varieties are available in this crop and efforts should be made to breed high yielding
varieties eithef from the existing or from introduced germplasm and develop location
specific precision agro-technologies. India can increase the area under cultivation and
can become an important exporting country of wild marigold products.
ACKNOWLEDGEMENTS
The authors thank the Director, CSIR-CIMAB Lucknow for facilities and
encouragement.
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