Phytochemical Investigation of Male and Female Hedyosmum
Leaves from Ecuador
and Gianluca Gilardoni
Departamento de Qu
ımica y Ciencias Exactas, Universidad T
ecnica Particular de Loja, San Cayetano Alto s/n, Loja,
Ecuador, e-mail: firstname.lastname@example.org
Dipartimento di Chimica and CEMEC, Universit
a degli Studi di Pavia, Viale Taramelli 12, 27100, Pavia, Italy
Dipartimento di Scienza e Tecnologia del Farmaco, Universit
a degli Studi di Torino, Via Pietro Giuria 9, 10125, Torino,
This article reports the chemical composition of the essential oils obtained by hydrodistillation of male and
female H. scabrum fresh leaves. The essential oils, HSMO and HSFO, respectively, were analyzed by GC/MS and
GC-FID. A total of 93 components were detected, accounting for 94.8% and 95.3% of HSMO and HSFO, respectively.
The prevalent constituents of HSMO were pinocarvone (13.1%),
-germacren-4-ol (12.6%), 1,8-cineole (10.8%),
a-pinene (6.4%), and b-pinene (4.8%), whereas the major components of HSFO were 1,8-cineole (20.5%), linalool
(16.5%), a-pinene (15.0%), b-pinene (6.4%), and sabinene (6.3%). The different enantiomeric distribution of b-pinene,
sabinene, limonene, linalool in the two oils, was determined. The non-volatile esters of p-coumaric and ferulic acids
with borneol (1 and 4), cis-chrysanthenol (2 and 5), and cis-pinocarveol (3 and 6) were identiﬁed in the leaves after
basic hydrolysis and analysis of the NMR spectra of the free acids, and GC/MS spectra of the monoterpene alcohols,
respectively. Compounds 2, 3, 5, and 6 have been found in nature for the ﬁrst time. These ﬁndings demonstrated
that, from a chemical point of view, male and female individuals of H. scabrum collected in Ecuador seem quite
differentiated between each other and from samples of the same species growing in Bolivia and in Peru.
Keywords: Hedyosmum scabrum, male and female individuals, essential oils, enantiomeric distribution, aromatic
esters of monoterpenoid alcohols, Ecuador.
The genus Hedyosmum, which means sweet smell in
ancient Greek, is only present in America. It is com-
posed by about 40 species growing on mountains,
which have distinct taxonomic characters.
majority of the species are strongly aromatic trees or
shrubs, while only rarely they are herbaceous plants.
The trees are dioecious, and some have male and
Several species are used all around
the world as ornamental or medicinal plants and as a
In Ecuador, which is one of the world’s most
biodiverse countries and where ancestral traditions
are still practiced,
Hedyosmum scabrum grows from
1500 to 3500 m above the sea level in the provinces
of Azuay, Bol
nar, Carchi, El Oro, Imbabura, Loja,
Morona Santiago, Napo, Pastaza, Pichincha,
ıos, and Tungurahua.
It is commonly known
with the indigenous names of Granizo, Tarqui, and
Guayusa de cerro. It is used against stomach-ache and
as a food.
Previous phytochemical investigations of
this genus led to the isolation of the sesquiterpene
onoseriolide from H. angustifolium, which exhibited a
potent activity against axenic amastigotes from
Leishmania amazonensis and Leishmania infantum.
Moreover, the sesquiterpene lactone 13-hydroxy-8,9-
dehydroshizukanolide was isolated from H. brasiliense
and showed antidepressant
On the other hand, ﬁve new guaiane-type
sesquiterpenoids were isolated from the aerial parts of
and a new ﬂavonoid with a signiﬁcant
analgesic activity was isolated from H. bonpiandi-
The essential oils from leaves and fruits of
H. mexicanum, H. bonplandianum, H. costaricensis from
H. colombianum from Colombia,
from leaves of H. brasiliense from Brazil
ied. The essential oil isolated from leaves of
H. scabrum collected in Bolivia
viously been investigated; however, the chemical com-
positions of the essential oils from male and female
individuals were not compared. Indeed, the study of
volatile compounds from male and female specimens
of the same plant may give signiﬁcative clues of the
plant secondary metabolism.
DOI: 10.1002/cbdv.201700423 Chem. Biodiversity 2018, 15, e1700423 © 2018 Wiley-VHCA AG, Zurich, Switzerland
(1 of 9) e1700423