Monograph-Cistus/Labdanum (Cistus ladanifer)

Monograph-Cistus/Labdanum (Cistus ladanifer)

Images of Cistus

Cistus ladanifer is a species of flowering plant in the family Cistaceae. It is a native of the western Mediterranean region. It is indigenous to Spain, Portugal and north-west Africa. Common names include Gum Rockrose, Ladanum, Gum Ladanum and Brown-eyed Rockrose.[1]

It is a shrub growing 1-2.5 m tall and wide. The leaves are evergreen, lanceolate, 3–10 cm long and 1–2 cm broad, dark green above and paler underneath. The flowers are 5–8 cm diameter, with 5 papery white petals, usually with a red to maroon spot at the base, surrounding the yellow stamens and pistils. The whole plant is covered with the sticky exudate of fragrant resin.

C. ladanifer is particularly well suited to the Continentalized Mediterranean climate, standing both long summer droughts and cold weather. It is an extremely aggressive plant which has taken over much of former farmland and grasslands in the mountain regions of central Spain. In Spanish it is known as Jara pringosa meaning "sticky shrub". C. ladanifer has been found to have mycorrhizal associations with Boletus edulis, Boletus rhodoxanthus, and Laccaria laccata.[2]
Wikipedia

"In ancient times the valuable aromatic gum ladanum was gathered manually from Cistus creticus subsp. creticus, especially in Crete and Cyprus. The gum is exuded from glandular hairs on the leaves and young stems, especially under hot sunshine. It was gathered by allowing goats to graze on and among the plants; the ladanum adhered to their beards, which were then cut off. Alternatively a device called a ladanisterion or ergastiri, with long thongs of leather, was drawn over the plants by hand during the hottest part of the day, when the ladanum was at its runniest and stickiest.. The leather thongs became caked with ladanum, which was then scraped off and formed into lumps of various shapes. A very small amount of ladanum is still gathered in this traditional way in a small area surrounding a village in northern Crete."
Cistus Page

"Ledanum, which the Arabs call ladanum, is procured in a yet stranger fashion. Found in a most inodorous place, it is the sweetest-scented of all substances. It is gathered from the beards of he-goats, where it is found sticking like gum, having come from the bushes on which they browse. It is used in many sorts of unguents, and is what the Arabs burn chiefly as incense." [1]
Herodotus' Histories, Book III (Thalia), Chap.112; trans. George Rawlinson in 1910; we are using the 1997 Everyman Library, Knopf edition, pp.278-279.

History of Labdanum
History and use of ladanum

Since antiquity several Cistus species have been known
for their production of an aromatic resin called ladanum
or labdanum (not to be confused with laudanum, which
is an opium tincture). Ladanum is exuded by glandular
hairs on the leaves and stems of C. ladanifer, C. palhinhae
and C. incanus ssp. creticus (Hegi 1966) and of hybrids
of Cistus ladanifer with C. laurifolius., C. monspeliensis
and C. salvifolius (Hanelt 2001). It is one of the classical
ingredients of perfumery and it was believed to possess
great medicinal properties as well. It has a smoky, leathery,
warm-woody fragrance, with strong notes of incense and
ambergris (Weyerstahl et al. 1998).
Aromatic materials obtained from Cistus species were
mentioned in the Bible, and the usefulness of products from
Cistus plants was described by Greek and Roman authors
like Herodotus (III, 112), Dioscorides (Materia Medica I,
128) and Pliny the Elder (Historia Naturalis XII, 37; XXVI,
30). According to Newberry (1928), ladanum was already
being collected by the Egyptians as early as the First Dy-
nasty.
Ladanum was collected from the beards and fur of goats
that had been browsing amongst Cistus shrubs or by sim-
ply walking through the Cistus shrubs with a ladanisteria,
a bow-shaped implement with straps or thongs wound with
wool. The resin was then scraped off the straps and pressed
into lumps (Warren 2002). In northwest Europe, ladanum
is first mentioned in medieval herbal books and recipes, in
both cases as an ingredient of medical preparations and per-
fumes (Dodoens 1644; Braekman 1990) (Fig. 3). Also, in
a number of recipes for the embalming of corpses given
by the 16th century physician P. van Foreest, ladanum
and ‘Alipta muscata’, an aromatic preparation containing
ladanum, were mentioned (Bosman-Jelgersma and van der
Waa 2000).
Nowadays both oleoresin and essential oil of C. ladani-
fer, C. incanus, C. monspeliensis, C. laurifolius and their
hybrids are used as fixatives in perfumery, soap manufac-
ture, as religious incense and for the treatment of leukaemia
(Mariotti et al. 1997; Weyerstahl et al. 1998; Hanelt 2001).
Cyprus, Crete, southern France (Esterel mountains), Spain
and Portugal are the main producers. It is obtained as a
gum by boiling the young shoots in water. The essential oil
is extracted by steam distillation of the gum (Weyerstahl
et al. 1998).
The historical use of ladanum. Palynological evidence from 15thand 16th century cesspits in northern Belgium

Will wine taste better if the grapes are stomped by barefoot virgins? How about cheese made by silent monks? Cookies baked by elves?

And will perfume smell more delicious if the labdanum in it has been scraped off the beards of Cretan goats?

Niktaris Dimitris hopes you will think so, as he harvests this perfume ingredient the traditional – as in, ancient – way. Actually, Dimitris does appear to raise goats but he gathers labdanum resin using this goat-simulator – a 1st C. tool called a ladanesterion.

It’s a kind of short handled mop, with a drape of leather strands. In the very hottest months of the year May-August, stalwart gatherers head to the hills and literally mop the resin off of blooming Cistus creticus flowers. (Dimitris stresses that “only the crimson flowers” produce high quality resin). The mops then dry several days in the summer sun and the resin hardens. Historically it was used in cosmetics, medicine and even food, but today it’s a prized ingredient in perfumes and incense.
Niktaris says his region of Crete (about twenty miles west of Heraklion, near the north coast) is the only place on earth where labdanum, a base note of in our favorite chypre perfumes, is gathered from this particular variety of rock rose, in this way. And the fragrance?
“The odour is very rich, complex and tenacious. Labdanum is much valued in perfumery because of its resemblance to ambergris, which has been banned from use in many countries because its precursor originates from the sperm whale, which is an endangered species. The odour is variously described as sweet, woody, ambergris, dry musk, or like that of leather.”
Human Flower Project


Cistus ladaniferus can be found all over the Mediterranean coast. This particular species of cistus is remarkable for the gum it produces in the summer which
has been used in perfumery for over 3000 years.
The gum Labdanum has an exceptionally strong balsamic and ambery odour which made it highly considered amongst the « incense » of Antiquity when it was known as Ladanum Resin.
Up until the 20’s the gum was collected directly from the plant and made into balls or bars. Originally it was collected by the shepherds from Crete or Cyprus from the fleece of goats covered in gum by wandering in the cistus fields.
Later on the gum was collected by whipping the twigs with a large rake called a Ladanisterion, which was made of strips of leather from which the gum was scrapped with a knife. From 1920, companies in Grasse began to produce the essential oil by distillation of the cistus from the Estérel region.
At the same time in the Salamanca province of Spain harvesters began to collect the gum by boiling the twigs.
Biolandes


Origin of the name
It comes from the Greek word "kistè" which means
"capsule" and refers to the shape of the fruit. The name of
the gum the plant produces, "labdanum" or "ladanum",
comes from its Persian origin "Lãd".
Location
Spontaneous plant, mainly growing on siliceous grounds.
Description of the plant
Perennial high-stemmed shrub, reaching six feet high. The
stems bear perennial light-green oblong leaves.
The solitary flowers appear as early as April. They offer
large corollas usually composed of five white petals, each
with a dark-purple spot near the center of the flower. Hence
the Andalusian name of "Christ's tears".
The whole plant, but especially its leaves, produces a very
strong-smelling resinous exudate, labdanum, which
protects it from excessive evaporation. It's the gum that
makes this plant interesting.
Crop
The optimum crop takes place right in the middle of
summer (July, August) because the heat then favours the
exudate production.
Growing in the wild, the leafy branches are picked with a
sickle.
A word about the traditions
Traces of the use of Labdanum can be found in the very
ancient Carthagenian and Egyptian civilizations. Labdanum
was also part of Ahassuerus's “Royal Persian Perfumery”
components.
Herodotus tells that it was picked by combing the goat
coats. Labdanum balls were made and exported for
perfumery and chemistery use.
Uses
They are medical, mainly external (hemostatic, healing and
wrinkle-reducing properties), but major use is in perfumery.
Processing
Through the various processes of distillation and extraction
of either fresh or dry plants can be obtained numerous
perfumery products.
Cistus is one of the very fews plant to offer an amber note.
Cistus has a major importance in perfumery as this plant is
the source of Labdanum gum, and Labdanum essential
oil and its resinoid as well Cistus concrete and absolute,
specific source of such an amber note (such as Cistasur and
Labdasur), not forgetting indeed Cistus essential oil.
Aromasur, our production facility set in Almaden de Plata
near Seville, is rich with a well tested know-how in these
various products.
LABDANUM CISTUS
Cistus ladaniferus L. var. beta maculata Dun.
Family of the Cistaceae
SPAIN
Production process
This Oil is produced by pressurized steam distillation of
leafy stems of Cistus ladaniferus var. maculatus. Yield is
very low, around 0.1%.
Appearance
Cistus Essential Oil is an orange brown liquid.
Odor Description
Amber, woody, powerful, and tenacious.
Physical-chemical data
The values quoted below are not standardized:
Density d20/20 0.940 to 0.965
Refractive Index 1.45 to 1.50
Rotatory Power -10° to +6° C
Composition
Cistus Essential Oil owns a very complex composition;
more than 250 components have been identified.
Several structures are present: terpenes, sesquiterpenes,
aromatic, alkanes and diterpenes (mostly those having a
labdanate structure). Those last show the specific structures
that typify Cist, and deliver the amber note.
The hydro carbonate fraction accounts for about 40% of
the Essential oil.
The main (>1%) hydrocarbons are: a-pinene, camphene,
isopropyl methyl benzene, limonene, p-dimethylstyrene,
guaïadiene 3,7, aroma-dendrene, allo aromadendrene, 1,5 -
cis-aromadendr-9-ene, and ledene. They are joined by a large
amount of minor hydrocarbons, and specifically labdenes.
Among the oxygenated components (due to its length, a
complete list cannot be given here) are found:
Oxides: 1,8 cineole, nerol oxyde, sclareol oxyde, 6,8,-epoxy
menthene-1, cis and trans rose oxide, pinene oxide, ambrox,
cis and trans linalol oxyde, 6-oxo-isoambrox.
Aldehydes: a and g campholic aldehyde, cuminaldehyde,
nonanal, tetradecanal, myrtenal, b cyclocitral.
Ketones: trimethyl-2,2,6- cyclohexanone, cis and trans
tagetones, acetophenone, trans nonene-3-one-2, camphor,
carvone, pinocamphone, isopinocamphone, pinocarvone,
6-acetoxy-11-nor-drim-7-ene-9-one.
Esters: bornyle acetate, trans pinocarvenyle, myrtenyl, ethyl
and methyl dihydrocinnamate.
Alcohols: linalol, trans pinocarveol, borneol, terpinene-4-
ol, palustrol, ledol, viridiflorol, cubeban-11-ol.
Diterpenic alcohols: 15-nor-labdan-8-ol, labd-8(17)-en-
15-ol, labd-7-en-15-ol, labd-8-en-15-ol.
Phenol: eugenol, carvacrol.
Acids: nonanoate acid, decanoic, geranic, dihydrocinnamic,
a campholenic and a campholytic. These last two
components represent roughly the third of the acid fraction,
and are said to strengthen the woody and resinous note of
the Essence. Dihydrocinnamic acid, as well as eugenol adds
a more balsamic note. The diterpenic acids, as well as the
oxides, esters, and deterpenic alcohols reinforce the Essence
amber character.
Production process
Cistus Concrete is produced by solvent extraction of the
plant aerial parts. The solvent is later eliminated by
concentrating the extract.
Yield is about 5%.
Cistus Absolute is produced by washing the Concrete with
ethanol. This washing step is followed by glazing and
filtration, to get rid of the waxes. Concentrating the
alcoholic phase delivers the Absolute.
Yield from Concrete is about 65%.
Appearance
The Concrete is a dark brown mass. The Absolute is a highly
viscous liquid.
Odor Description
Cistus extracts have a potent amber scent, and spicy
& tobacco notes.
Composition
Cistus extracts contain a volatile fraction which quality is
similar to the essential Oil one, which is extremely complex.
Besides this volatile fraction, we find heavier components:
waxes (especially in the Concrete), resins, tannins, and
mostly polyterpenic derivatives.
Cistus extract analysis is performed - as is the case with
Labdanum - trough a “chemical sorting” enabling to
separate the various families of components.
The diterpenic components that trigger the amber note are
more numerous in the Concrete and the Absolute.
The post volatile fraction is made up of terpenes, alcohols,
and of ketones (among those we find again a pinene,
p dimethyl styrene, aromadendrene, allo-aromadendrene,
1,5 cis aromaden-9-ene, ledene, trans pinocarveol, borneol,
palustrol, ledol, cubeban-11-ol, copaborneol, trimethyl-
2,2,6-cyclohexanone, trans nonene-3-one, pinocamphone
and isopino-camphone.
A heavier fraction is made up of diterpenes, such as
Labdene-7,8-ol-15, labdene-8,9-ol-15, labdene-8,20-ol-15,
labdanolic acid, labdene-7,8-oic acid, labdene-8,9-oic acid,
and labdene-8,20-oic acid.
Others acids exist in the extracts. We find aromatic acids:
benzoic, cinnamic (cis and trans), anisic, phenyl-propanoic.
As well as fatty acids: palmitic, stearic, eicosanoic...
These acids are also found in the Absolute as ethylic esters.
Lastly, Cistus extracts contain various alcanes.
CONCRETE AND ABSOLUTE
Labdanum, an exudate from cistus branches, is the
raw-material from which numerous amber-smelling
products are derivated. It does belong to the very few
amber-note scents that exist in the vegetable kingdom.
Manufactoring process
The aerial parts of the plant are immersed into warm
carbonated water. The acidification of the medium allows
the separation of the raw gum. The latter, a soft ambersmelling
sticky mass, is drained off and dried. The
labdanum resinoid is obtained from the gum through an
alcoolic extraction, then through a concentration.
Yield
75% of the gum.
Appearance
Solid, pasty, dark-brown.
Smell
Amber-smelling, woody, balsamic, powerful, clinging.
Composition
The analysis of the labdanum resinoid is extremely complex
and has needed very elaborated studies.
The composition of the labdanum extracts is so rich that it
can't be dealed with in a simple way. So every analysis usually
includes a “chemical sorting” of the present constituents,
which means the separation of the various families of
components.
The heaviest fractions are then isolated (steriles, insolubles,
tannins) as well as the acids, the phenols and the neutral
substances.The analysis is then done one family at a time,
sometimes on condition of a derivation (chemical
transformation).You will then understand how difficult it
may be to announce with precision the exact quantities and
percentage of each constituent in the resinoid.
Distinctive constituents
The most remarkable constituents of the resinoid are the
diterpenes that have a labdane framework.
They can be found under various aspects such as the
labdanolic acid, the acetoxy-15 labdanol-8, or the labdeneacetoxy-
8,9. These constituents participate in the ambersmelling,
deep and clinging note of the resinoid.
To the natural complexity of the products can be added the
effects due to the processes. The structures are quite a lot
modified by the contact with ethanol (an esterification
phenomenon so that labdenoates of ethyle can be found in
the resinoid) or by some thermal effects (pyrolysis). These
effects may be led in such way as to obtain the wished
olfactive characteristics.
Therefore, with the fractioned resinoid, we can obtain such
different products as those two specialities :
- the Cistasur, with an amber smell, delicately balsamic, soft
and clinging.
- the Labdasur, with an animal characteristic, leatheramber-
smelling, powerful.
Acidification
Some references about Labdanum
K. TAJIMA, J. YAMAMOTO, N. TOI, “Amber odor
constituents in labdanum gum”, Flavours, Fragrances
and Essentials oils, Proceedings of the 13th International
Congress of Flavours, Fragrances and
essentials oils, Istanbul, Turkey, (AREP publ.) 1995,
vol. 2, pp. 217-224.
P. WEYERSTAHL, H. MARSCHALL, M.WEIRAUCH, “Constituents
of commercial labdanum oil”, Flavour and
Fragrance Journal, 1998, 13, 295-318.
B.M. LAWRENCE, “Progress in essential oils: Cistus and
Labdanum Isolates and extracts”, Perfumer and
Flavorist, 1999, 24, Jul.-Aug, pp 41-50.
J. BRUNETON, “Pharmacognosie Phytochimie et Plantes
médicinales”, 1993, 2e éd., Lavoisier, pp 512-514.
RÉSINOÏD LABDANUM
Albert Vielle Monograph

Medicinal use of Labdanum:
Labdanum is an aromatic, expectorant, stimulant herb that controls bleeding and has antibiotic effects. It is used internally in the treatment of catarrh and diarrhoea and as an emmenagogue. The leaves are harvested in late spring and early summer and can be dried for later use, or the resin extracted from them.
Natural Medicinal Herbs