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Strigolactones: occurrence, structure, and biological activity in the

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Phytochem Rev
DOI 10.1007/s11101-014-9370-4

Strigolactones: occurrence, structure, and biological activity

in the rhizosphere
Sanja Ćavar • Binne Zwanenburg •

Petr Tarkowski

Received: 13 December 2013 / Accepted: 17 June 2014

Ó Springer Science+Business Media Dordrecht 2014

Abstract Strigolactones are signaling molecules
that play a role in host recognition by parasitic plants
of the Striga, Orobanche and Phelipanche genera
which are among the most detrimental weeds in
agriculture. The same class of molecules is also
involved in the establishment of the symbiosis of
plants with arbuscular mycorrhizal fungi. In addition,
strigolactones are being shown to be involved in an
increasing number of physiological processes in
plants, such as the regulation of plant architecture
and the response to abiotic factors such as nutrient
availability and light. Important advances in knowl-
edge about the structure determination, occurrence,
biological function and physiological and biochemical
regulation of the strigolactones have been revised.
This review presents the complete collection of
S. Ćavar  B. Zwanenburg  P. Tarkowski (&)
Centre of Region Haná for Biotechnological and
Agricultural Research, Faculty of Science,
Palacky University, Slechtitelu 11, 78371 Olomouc,
Czech Republic
e-mail: petr.tarkowski@upol.cz
S. Ćavar
Department of Chemistry, Faculty of Science, University
of Sarajevo, Zmaja od Bosne 33-35, 71000 Sarajevo,
Bosnia and Herzegovina
B. Zwanenburg
Department of Organic Chemistry, Institute for Molecules
and Materials, Radboud University Nijmegen,
Heyendaalseweg 135, 6525 AJ Nijmegen
The Netherlands
available spectroscopic data of correct structures of
strigolactones, the occurrence in plant kingdom, as
well as germination and hyphal branching activities,
that are of high importance to the scientific community
that is investigating these novel plant hormones.
Moreover, two new structures of strigolactone mem-
bers are proposed.
Keywords Strigolactones  Phytohormones 
Structure elucidation  Seed germination  Hyphal
branching
Introduction
Strigolactones (SLs) have been recently recognized as
a new family of phytohormones. They have been
suggested to act as long distance branching factors that
suppress the growth of preformed axillary shoot buds,
thereby fulfilling the characteristics of a new group of
plant hormones (Gomez-Roldan et al. 2008; Umehara
et al. 2008; Tsuchiya and McCourt 2012; Brewer et al.
2013; de Saint et al. 2013a; Koltai 2013; Tsuchiya and
McCourt 2009). However, SLs were known for almost
50 years as germination stimulants of the parasitic
plants Striga and Orobanche (Cook et al. 1966; Xie
et al. 2010; Nomura et al. 2013) and later, as stimulants
of hyphal branching of symbiotic arbuscular mycor-
rhizal (AM) fungi (Akiyama et al. 2005; Besserer et al.
2006; Xie et al. 2010; Seto et al. 2012).

123

SLs are classified as carotenoid-derived terpenoid
lactones (Matusova et al. 2005) and their presence has
been demonstrated in several plant species. In most of
these cases a mixture of several SLs was detected (Xie
et al. 2010). The roots are the main site of SL
biosynthesis in plants, and their synthesis in the lower
part of the shoot has also been suggested (Dun et al.
2009). Nevertheless, to induce a significant reduction
in shoot branching, it is suggested that SLs, their
metabolites or other unknown secondary messengers,
move in the root-to-shoot direction (Dun et al. 2009).
Accordingly, the SL orobanchol was detected in
xylem sap in Arabidopsis, further supporting the
suggestion that root-derived SLs are transported to the
shoot (Kohlen et al. 2011; Seto et al. 2012). Additional
roles for SLs in plants, including regulation of
secondary growth (Agusti et al. 2011), adventitious
root formation (Rasmussen et al. 2012) and root
development (Kapulnik et al. 2011a; Ruyter-Spira
et al. 2011) were discovered. Moreover, several
studies have demonstrated a role for SLs in shoot
responses to low Pi conditions (Umehara et al. 2008).
Even before the signaling role of SLs for AM fungi
was discovered, there was a substantial interest in the
isolation and identification of these signaling mole-
cules from a range of plant species. SLs are produced
by plants in extremely low quantities and they may be
unstable during the purification process. Their pro-
duction is plant dependent. Sato et al. (2005) showed
that average strigol and strigyl acetate production
levels in cotton are around 15 and 2 pg/plant/day,
respectively, while Yoneyama et al. (2007b) reported
around 36 ng/plant of orobanchol in red clover
growing in P deficient conditions within 3 days.
Therefore, their isolation, purification, and struc-
ture elucidation are very difficult. In this review the
occurrence of SLs in the plant kingdom, their structure
and bioactivity in interaction with parasitic seeds and
arbuscular mycorrhizal fungi will be presented.
Naturally occurring strigolactones
SLs have been detected in the root exudates of a wide
range of mono- and dicotyledonous plant species.
Different plant species and even different varieties of
one crop species produce different SLs and/or mix-
tures of these signaling compounds. To date fifteen
naturally occurring SLs have been detected and their
123
Phytochem Rev
structures elucidated (Fig. 1). Table 1 represents the
detailed overview of the occurrence of SLs in the
investigated plant species. The structures of some SLs
presented in Table 1 are not correctly determined
(references are marked with asterisks). The details of
these structures will be discussed further on.
It appears that single plant species can produce
multiple SLs and different species produce different
SLs in various quantities (Cardoso et al. 2011; Xie
et al. 2013). This is in a contrast with the presence of
another phytohormone, abscisic acid, a compound
whose structure is conserved through plant kingdom.
SLs might be more akin to gibberellins, of which more
than 100 structures have been identified to date. But,
on the other hand, only few of these gibberellins are
actually biologically active. Moreover, Tsuchiya and
McCourt (2012) suggest classification of SLs as
pheromones, because their structural diversity is the
common theme of pheromones and other allelochem-
icals. Moreover, Proust et al. (2011) demonstrated that
moss (P. patens) produce SLs in order to control
developmental and ecophysiological processes. These
authors propose that SLs are reminiscent of quorum-
sensing molecules used by bacteria to communicate
with one another. In 1966, strigol and strigyl acetate
were isolated from root exudates of cotton (Gossypium
hirsutum L.) which is a non-host of Striga (Cook et al.
1966; Xie et al. 2010; Zwanenburg and Pospisil,
2013). Strigol was then also identified in the root
exudates of genuine Striga hosts, sorghum, maize, and
common millet (Table 1). Subsequently, two strigol-
related germination stimulants, sorgolactone and
alectrol, were isolated from root exudates of sorghum
and cowpea, respectively. At that time the proposed
structure of alectrol was incorrectly assigned (refer-
ences in the Table 1 are marked with asterisks). Butler
(1995) named these strigol-like compounds ‘‘strigo-
lactones’’ (SLs), due to the fact that all known SLs
contain lactone groups. Sorgomol, another isomer of
strigol, was first found in sorghum (Awad et al. 2006),
and then in root exudates of Lupinus albus (Yoneyama
et al. 2008), Cosmos bipinnatus (Yoneyama et al.
2011), and Astragalus sinicus (Yoneyama et al. 2012).
Recently, one more derivative of strigol was isolated
from root exudates of Houttuynia cordata having a
carbonyl group in the A-ring and accordingly was
named strigone (Kisugi et al. 2013).
The simplest known SL, 5-deoxystrigol, was first
isolated from root exudates of Lotus japonicus
Phytochem Rev
Fig. 1 Structures of natural strigolactones
(Akiyama et al. 2005), and later from wide variety of
plant species belonging to the Fabaceae (Yoneyama
et al. 2008) and Asteraceae families (Yoneyama et al.
2011). Due to its simplicity, 5-deoxystrigol was
proposed to be the common precursor of other SLs
(Rani et al. 2008; Zwanenburg et al. 2009; Xie et al.
2010). Jamil and co-authors recently reported the
presence of one derivative of 5-deoxystrigol in four
different rice species, namely methoxy-5-deoxystrigol
(Jamil et al. 2011a, b).
Among all the known SLs, two have very unique
structure. Fabacyl acetate contains an epoxide group,
and solanacol has an aromatic ring. Fabacyl acetate
was first found in garden pea (Xie et al. 2009a), and
later in few plant species belonging to the Fabaceae
(Yoneyama et al. 2008) and Asteraceae families
(Yoneyama et al. 2011). The true structure of solana-
col was determined recently (Chen et al. 2010; see also
Zwanenburg and Pospisil 2013). Therefore, references
in Table 1 concerning the occurrence of this aromatic
SL are marked with an asterisk. Solanacol was first
isolated from root exudates of tobacco (Xie et al.
2007), and was shown to be one of the major SLs in
tomato (López-Ráez et al. 2008; Koltai et al. 2010;
López-Ráez et al. 2010; López-Ráez et al. 2011;
Koltai et al. 2011).
Orobanchol and its acetate are the most common
SLs in plant kingdom (Table 1). The structure of
orobanchol first isolated by Yokota et al. (1998) was
assigned using spectra, chromatographic and physical
data as especially an assumed stereochemical relation-
ship with (?)-strigol (C-ring in a b-orientation). This
structure was confirmed by synthesis (Hirayama and
Mori 1999). However, chiroptical data were not
available at that time to substantiate the stereochem-
istry of the natural orobanchol. The structures of this
orobanchol and its acetate were reinvestigated by Ueno
et al. (2011a). By using amongst others chiroptical data
123
 Phytochem Rev

Table 1 An overview on plant species where information is available on the presence of strigolactones in roots and root exudates
Strigolactone Plant species Reference

Strigol Gossypium hirsutum Cook et al. (1966), Sato et al. (2005)

Houttuynia cordata Kisugi et al. (2013)
Menispermum dauricum Yasuda et al. (2003)
Panicum miliaceum Siame et al. (1993)
Sorghum bicolor Siame et al. (1993), Awad et al. (2006)
Trifolium pratense Yokota et al. (1998), Sato et al. (2003), Xie et al.
(2008a)
Vigna unguiculata Siame et al. (1993)
Zea mays Siame et al. (1993)
Strigyl acetate Gossypium hirsutum Sato et al. (2005)
Trifolium pratense Xie et al. (2008a)
Sorgomol Astragalus sinicus Yoneyama et al. (2012)
Cosmos bipinnatus Yoneyama et al. (2011)
Lupinus albus Yoneyama et al. (2008)
Sorghum bicolor Xie et al. (2008b), Jamil et al. (2011b)
Sorgolactone Sorghum bicolor Hauck et al. (1992), Xie et al. (2008b)
Trifolium pratense Sato et al. (2003)
Strigone Houttuynia cordata Kisugi et al. (2013)
5-Deoxystrigol Actium lappa Yoneyama et al. (2011)
Arachis hypogaea Yoneyama et al. (2008)
Astragalus sinicus Yoneyama et al. (2008), Yoneyama et al. (2012)
Carthamus tinctorius Yoneyama et al. (2011)
Chrysanthemum coronarium Yoneyama et al. (2011)
Cicer arietinum Yoneyama et al. (2008)
Cosmos bipinnatus Yoneyama et al. (2011)
Glycine max Yoneyama et al. (2008)
Lactuca sativa Yoneyama et al. (2011)
Lotus japonicus Akiyama et al. (2005), Sugimoto and Ueyama (2008)
Lupinus albus Yoneyama et al. (2008)
Medicago sativa Yoneyama et al. (2008)
Oryza sativa Umehara et al. (2010)
Pennisetum typhoideum Awad et al. (2006)
Phaseolus vulgaris Yoneyama et al. (2008)
Pisum sativum Yoneyama et al. (2008)
Psophocarpus tetragonolobus Yoneyama et al. (2008)
Sorghum bicolor Awad et al. (2006), Yoneyama et al. (2007a), Xie et al.
(2008b), Jamil et al. (2013)
Vicia faba Yoneyama et al. (2008)
Vigna angularis Yoneyama et al. (2008)
Zea mays Awad et al. (2006)
Methoxy-5-deoxystrigol Oryza indica Jamil et al. (2011b)
Oryza japonica Jamil et al. (2011b)
Oryza javanica Jamil et al. (2011b)
Oryza sativa Jamil et al. (2011a)
Fabacyl acetate Astragalus sinicus Yoneyama et al. (2008)

123
Phytochem Rev
Table 1 continued
Strigolactone Plant species
Carthamus tinctorius
Hedypnois rhagodioloides
Medicago sativa
Pisum sativum
Vicia faba
Solanacol Nicotiana tabacum
Solanum lycopersicum
Trifolium incarnatum
Solanacyl acetate Nicotiana tabacum
Orobanchol Actium lappa
Actium lappa
Arabidopsis thaliana
Arachis hypogaea
Astragalus sinicus
Carthamus tinctorius
Glycine max
Hedypnois rhagodioloides
Lactuca sativa
Linum usitatisimmum
Lupinus albus
Medicago sativa
Nicotiana tabacum
Oryza indica
Oryza japonica
Oryza javanica
Oryza sativa
Petunia hybrida
Phaseolus vulgaris
Pisum sativum
Psophocarpus tetragonolobus
Solanum lycopersicum
Sorghum bicolor
Tagetes erecta
Tagetes patula
Trifolium incarnatum
Trifolium pratense
Trifolium pratense
Triticum aestivum
Vicia faba
Vigna angularis
Reference
Yoneyama et al. (2011)
Yoneyama et al. (2011)
Yoneyama et al. (2008)
Xie et al. (2009a), Foo (2013)
Yoneyama et al. (2008)
Xie et al. (2007)**
López-Ráez et al. (2008)*, Koltai et al. (2010)*, López-
Ráez et al. (2010)*, López-Ráez et al. (2011)*, Koltai
et al. (2011)*
Yoneyama et al. (2008)*
Xie et al. (2013)
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Goldwasser et al. (2008)*
Yoneyama et al. (2008)*
Yoneyama et al. (2008)*
Yoneyama et al. (2011)*
Yoneyama et al. (2008)*, Xie et al. (2008b)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*, Yoneyama et al. (2012)*
Xie et al. (2009b)*
Yoneyama et al. (2008)*
Yoneyama et al. (2008)*, Yoneyama et al. (2012)*
Xie et al. (2007)*
Jamil et al. (2011b)*
Jamil et al. (2011b*, 2012)*
Jamil et al. (2011b)*
Jamil et al. (2011a*, b)*
Yoneyama et al. (2011)*
Yoneyama et al. (2008)*
Yoneyama et al. (2008)*, Xie et al. (2009a)*, Foo and
Davies (2011), Foo (2013)
Yoneyama et al. (2008)*
López-Ráez et al. (2010)*, Koltai et al. (2011)*,
Yoneyama et al. (2012)*
Awad et al. (2006)*
Yoneyama et al. (2011)*
Yoneyama et al. (2012)*
Yoneyama et al. (2008)*
Yokota et al. (1998)*, Sato et al. (2003)*, Yoneyama
et al. (2007a, 2007b)*, Xie et al. (2008b)*, Yoneyama
et al. (2011)*
Ueno et al. (2011a)
Yoneyama et al. (2012)*
Yoneyama et al. (2008)*
Yoneyama et al. (2008)*
123

Table 1 continued
Strigolactone Plant species
Vigna unguiculata
Vigna unguiculata
Orobanchyl acetate Actium lappa
Arachis hypogaea
Astragalus sinicus
Carthamus tinctorius
Chrysanthemum coronarium
Cicer arietinum
Cosmos bipinnatus
Glycine max
Hedypnois rhagodioloides
Helianthus annuus
Lactuca sativa
Linum usitatisimmum
Lupinus albus
Medicago sativa
Petunia hybrida
Phaseolus vulgaris
Pisum sativum
Psophocarpus tetragonolobus
Tagetes erecta
Tagetes patula
Trifolium incarnatum
Trifolium pratense
Vicia faba
Vigna angularis
Vigna unguiculata
7-Oxoorobanchol Cucumis sativus
Linum usitatisimmum
7-Oxoorobanchyl acetate Actium lappa
Carthamus tinctorius
Chrysanthemum coronarium
Cosmos bipinnatus
Cucumis sativus
Lactuca sativa
Linum usitatisimmum
Petunia hybrida
Tagetes erecta
Tagetes patula
Trifolium pratense
7-Hydroxyorobanchol Cucumis sativus
Linum usitatisimmum
123
Phytochem Rev
Reference
Xie et al. (2008b)*, Matsuura et al. (2008)*
Ueno et al. (2011a)
Yoneyama et al. (2011)*
Yoneyama et al. (2008)*
Yoneyama et al. (2012)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Yoneyama et al. (2008)*
Yoneyama et al. (2011)*
Xie et al. (2008b)*, Yoneyama et al. (2008)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*, Yoneyama et al. (2012)*
Xie et al. (2009b)*
Yoneyama et al. (2008)*
Yoneyama et al. (2008)*, Yoneyama et al. (2012)*
Yoneyama et al. (2011)*
Yoneyama et al. (2008)*
Yoneyama et al. (2008)*, Xie et al. (2009a)*, Foo and
Davies (2011), Foo (2013)
Yoneyama et al. (2008)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*, Yoneyama et al. (2012)*
Yoneyama et al. (2008)*
Sato et al. (2003)*, Xie et al. (2008a)*, Ueno et al.
(2011a)
Yoneyama et al. (2008)*
Yoneyama et al. (2008)*
Xie et al. (2008b)*, Matsuura et al. (2008)*, Müller
et al. (1992)**
Xie et al. (2010)
Xie et al. (2009b)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Xie et al. (2010)*
Yoneyama et al. (2011)*
Xie et al. (2009b)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Xie et al. (2010)*
Xie et al. (2009b)*
Phytochem Rev
Table 1 continued
Strigolactone Plant species
7-Hydroxyorobanchyl acetate Cucumis sativus
Lactuca sativa
Petunia hybrida
Tagetes erecta
Tagetes patula
it was shown that the correct structure of naturally
occurring orobanchol is a stereoisomer of the origi-
nally proposed one. For the notation of the configura-
tion at stereo centers the International Union of
Applied Chemistry (IUPAC) recommends the use of
the Cahn-Ingold-Prelog (CIP) system whereby the
sense of chirality is indicated by the R and S descriptors
which are based on abstract rules. Although the R and
S descriptors are unambiguous and absolute stereo
parameters, the relative notation with respect to a
standard using ent and epi prefixes is an alternative
method (see also Zwanenburg and Pospisil 2013). The
configuration of the original orobanchol structure is
(3aS, 4S, 8bS, 20 R) and that of the correct structure
(3aR, 4R, 8bR, 20 R). In Fig. 1 the names of the natural
SLs are used together with their R and S descriptors.
The use of the prefixes for the stereochemistry may
lead to confusion when the standard is not specified, or
when reading older literature about orobanchol prior
the structure correction. If the originally proposed
structure for natural orobanchol is corrected to (-)-
(3aR, 4R, 8bR, 20 R)-orobanchol, then the synthetic (?)-
(3aS, 4S, 8bS, 20 R)-orobanchol originally proposed by
Mori will now be referred to as ent-20 -epi-orobanchol,
when the correct structure of the endogenous oroban-
chol is taken as the reference.
Recently, Xie et al. (2013) reinvestigated structures
of SLs produced by tobacco and rice. Their findings
concerning the naturally occurring SLs are in the
agreement with those reported by Ueno et al. (2011a).
Zwanenburg and Pospisil (2013) proposed the stereo-
chemistry in (?)-strigol as the general standard (used
by a.o. Ueno et al. 2011a, b; Nomura et al. 2013), but
others prefer to choose the new structure of endoge-
nous orobanchol as standard for the orobanchol
stereoisomers (Vurro and Yoneyama 2012; Yoneyama
et al. 2012, 2013). It is important to pay attention to the
ent/epi naming issue when reading the older literature.
Reference
Xie et al. (2010)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Yoneyama et al. (2011)*
Note that structures are most informative. In Fig. 1 the
names of SLs are always include the R/S descriptors.
References in Table 1 concerning orobanchol,
orobanchyl acetate and their 7-hydroxy- and 7-oxo-
derivatives, whose structures are not yet revised, are
marked with an asterisk. It should be pointed out that
in all references in Table 1 marked with an asterisk
authors used different stereoisomers of SL as a
standard, i.e. structures are incorrect with regard to
the recent structural correction, and in references
marked with double asterisks when authors incorrectly
assigned the structure of a particular SL.
Recent formation revealed that there are two classes
of natural SLs, namely a group having the stereo-
chemistry at the B/C junction as in (?)-(3aR, 5S, 8bS,
20 R)-strigol (C-ring has the b-orientation) and a group
with the stereochemistry as in (-)-(3aR, 4R, 8bR,
20 R)-orobanchol (C-ring has a-orientation), (Zwanen-
burg and Pospisil 2013; Yoneyama et al. 2011). It is
noteworthy that the orobanchol stereoisomer with the
originally proposed structure for Yokota’s compound
has recently been identified in the root exudates of
tobacco (Xie et al. 2013), so after all it is a natural SL.
Structure elucidation
All SLs that have been characterized up to now have
similar structures. The core of the molecules consists of
a tricyclic lactone (ABC part) connected via an enol
ether bridge to a butenolide group (the D-ring), (Fig. 1).
They can be classified into two groups, namely strigol-
like and orobanchol-like SLs. The classification refers
to the orientation of the C-ring, i.e. strigol-like SLs have
b-oriented C-ring (strigol and its acetate, sorgomol,
sorgolactone, strigone, 5-deoxystrigol and its putative
methoxy-derivative), whilst orobanchol-like SLs have
a-oriented C-ring (orobanchol and its acetate, fabacyl
123

acetate, and solanacol). The stereochemistry at C-20 is
the same in both families of SLs, namely R. Moreover,
all strigol-like SLs have S-stereochemistry at 8b carbon,
while orobanchol-like SLs have R-stereochemistry. In a
few cases an epi-orientation at C-20 has been reported
(Rani et al. 2008; Zwanenburg et al. 2009; Xie et al.
2010, 2013). However, this S stereochemistry C-20 still
needs to be confirmed in view of the current revision of
several SL structures.
All known SLs possess one or two methyl substit-
uents on the A-ring, and various combinations of
hydroxyl or acetoxy substituents on the A- and
B-rings, whilst the C- and D-rings are the same.
The structures of SLs (Fig. 1) have been assigned
by physical and spectral data and/or synthesis. Spec-
tral analysis tools are very powerful in assigning
structures to natural products. However, in the case of
strigolactones spectral analysis is hampered by the
very low concentrations in root exudates and accord-
ingly the isolation of sufficient amount is often
problematic. In aqueous solutions SLs are stable at
pH B 7. 5-Deoxystrigol has an estimated a t‘ of
1.5 days. The hydrolysis of this SL follows addition–
elimination pathway producing ABC lactone, and
5-hydroxybutenolide (Akiyama et al. 2010).
Knowledge about the biosynthetic origin of SLs in
plants may be of help in assigning unknown structures
(Matusova et al. 2005; Bouwmeester et al. 2007; Rani
et al. 2008). It should be stressed however, as was
highlighted in recent review of Zwanenburg and
Pospisil (2013), that the total synthesis of natural
SLs is far the most reliable and recommended method
for successful structure elucidation of these natural
products. The present section will be focused on a
collection of spectroscopic data of correct structures,
natural and synthesized SLs, known to date (Table 2).
It is appropriate to provide these data to the scientific
community that is investigating these novel plant
hormones.
As it is apparent from Table 2, spectroscopic data
of a few known SLs are lacking. For example, there are
no available spectroscopic data for hydroxy deriva-
tives of orobanchol occurring in tomato (Kohlen et al.
2013) and some species belonging to Asteraceae
family (Yoneyama et al. 2011). However, there is
confusion with CAS (Chemical Abstract Service)
numbers of these compounds. These numbers of
orobanchyl acetate and 7-oxoorobanchyl acetate exist
123
Phytochem Rev
in database, but they refer to incorrect structures.
Therefore, they are marked with asterisks in Table 2.
Identification of SLs is usually performed using GC–
MS (Erickson et al. 2001) or LC/MS/MS (Sato et al.
2003). For the quantitation by LC/MS/MS, the multiple
reaction monitoring (MRM) mode, is usually used. For
MRM, transitions of [M ? H]? or [M ? Na]? to
[M ? H - D ring]? or [M ? Na - D ring]?, respec-
tively, are monitored to detect SLs, because all known
SLs contain the same D-ring moiety (Table 3). Tandem
mass spectrometry also enables estimation of the
molecular formulae of unknown SLs even in crude
extracts based on their mass spectra (Sato et al. 2003;
Xie et al. 2010). The capillary and cone voltages are
normally adjusted to the positive ionization mode, and
collision energy is set around 16 eV.
1
H-NMR spectra provide only information about
the skeleton, without detailed stereochemistry. Nev-
ertheless, 1H- and 13C- spectra are of high importance
for the structure elucidation of SLs. In Table 4 the
general chemical shifts of 1H NMR spectra of SLs are
collected.
In recent years the relevance of the stereochemistry
of SLs has been clearly demonstrated. This led to
several revisions of originally proposed structures of
naturally occurring SLs and most likely some others
will follow. Zwanenburg and Pospisil (2013) suggested
revision of absolute stereochemistry of 7-oxo- and
7-hydroxy-orobanchol on the basis of their detailed CD
spectra. However, when recording CD spectra, all of
the strigol-like SLs show in the CD-spectra a large
positive Cotton effect around 230 nm, and small
Cotton effect of opposite sign around 250 and
270 nm. Sugimoto et al. (1998) and Welzel et al.
(1999) inferred that the sign of the Cotton effect around
250–270 nm could be directly correlated with the
stereochemistry at C20 position. A negative Cotton
effect around 250–270 nm correlates with R stereo-
chemistry at C-20 , whereas the Cotton effect of C-20
S compounds (enantiomers) is positive at that wave-
length. Recently Seto et al. (2014) assigned the correct
stereochemistry of carlactone (CL) as precursor of SLs.
CL possesses only one stereocenter on the butenolide
carbon. Interestingly, R-CL has a positive cotton effect
at 250–270 nm whereas S-CL has a negative cotton
effect. In the case of CL Welzel’s rule was not
conclusive due to the fact that chromophore of the
D-ring is sufficiently separated of the rest of molecule.
Phytochem Rev

Table 2 Available spectroscopic data of correct structures of strigolactones

Compound Reference

Strigol (CAS # 11017-56-4)

Isolated ESI–MS m/z (rel. int.) 715 [2 M ? Na]? (70), 369 [M ? Na]?(100). EIMS m/z (rel. int.) 346 Yasuda et al. (2003)
[M]? (0.27), 328 (4.2), 249 (15.7), 231 (78.6), 203 (25.6), 97 (100), 69 (6.1). 1H NMR
(400 MHz) d: 1.10 (3H, s, 8-Me), 1.18 (3H, s, 8-Me), 1.45 (1H, m, 7-H), 1.62 (1H, m, 6-H),
2.00 (1H, m, 6-H0 ), 2.03 (3H, s, 40 -Me), 2.72 (2H, m, 4-CH2), 3.65 (1H, m, 3a-H), 5.51 (1H,
d, J = 7.8, 8b-H), 6.13 (1H, m, 20 -H), 6.92 (1H, m, 30 -H), 7.45 (1H, d, J = 2.68, 9-H). CD
(MeCN) De206 - 21.8, De234 ? 29.0
Synthesized 1H NMR (500 MHz, CDCl3) d: 1.10 (s, 3 H, 8-Me), 1.17 (s, 3H, 8-Me),1.42-1.49 (ddd, 1H, Brooks et al. (1985),
J = 13.5, J = 11.3, J = 2.8 Hz, 7-H), 1.52-1.60 (ddd, 1H, J = 13.5, J = 7.1, J = 3.1 Hz, Hirayama and
7-H0 ), 1.58–1.62 (bs, 1H, OH), 1.64–1.73 (m, 1H, 6-H), 1.95–2.01 (ddd, 1H, J = 13.4, Mori (1999)
J = 7.1, J = 5 3.1 Hz, 6-H0 ), 2.00–2.03 (t, 3H, J = 1.5 Hz, 40 -Me), 2.64–2.76 (m, 2H,
4-CH2), 3.61–3.67 (dtd, 1H, J = 11.9, J = 4.0, J = 2.5 Hz, 3a-H), 4.08–4.15 (bs, 1H,
5.48–5.52 (d, 1H, J = 8.2 Hz, 8b-H), 6.15–6.18 (s, 1 H, 20 -H), 6.92–6.94 (t, 1 H, J = 1.5 Hz,
30 -H), 7.44–7.46 (d, 1H, J = 2.4 Hz, 9-H). CD (MeCN) De206 - 24.1, De231 ? 31.1.
a20
D = ?262.7 (c = 0.56 CDCl3)

Strigyl acetate (CAS # 38503-77-4)

Synthesized MS (C21H24O7) m/z (rel. int.) 388 (M?, 0.7), 346 (6), 328 (9), 231 (26), 97 (100). 1H NMR Frischmuth et al.
(400 MHz, CDCl3) d: 1.08 (s, 3 H, 8-Me), 1.18 (s, 3H, 8-Me), 1.41–1.51 (m, 1H, 7 = H), (1991)
1.53–1.59 (m. 1H. 7-H), 1.68–1.79 (m, 1H) and 1.90–2.00 (m, lH, CH2-6). 2.00 (t, 3H. 40 -
Me). 2.05 (s, 3H. COMe), 2.34–2.39 (m, 1H. 40 -H), 2.64–2.73 (dd, 1H. 4-H), 3.58–3.65 (m,
IH, 3a-H), 5.23–5.28 (m, 1H, 5-H), 5.43–5.48 (d, lH, 8b-H), 6.13–6.15 (m, lH, 20 -H).
6.87–6.90 (m, lH, 30 -H), 7.40–7.42 (d. lH, = CHO)
Sorgomol (CAS # 1011730-11-2)
Isolated 1H NMR: d 1.04 (11-Me), 1.27 (m, 7a-CH2), 1.70 (m, 6-CH2), 1.96 (m, 5-CH2), 2.03 (t, Xie et al. (2008b)
J = 1.5 Hz, 60 -Me), 2.38 (d, J = 17.1 Hz, 4b), 2.74 (dd, J = 17.1, 9.1 Hz, 4a-CH), 3.42 (d,
J = 11.7 Hz, 11a-CH), 3.59-3.66 (m, 3a-CH), 3.60 (d, J = 11.7 Hz, 10b), 5.51 (d,
J = 7.3 Hz, 8b-CH), 6.14 (t, J = 1.5 Hz, 20 -CH), 6.92 (t, J = 1.5 Hz, 30 -CH), 7.43 (d,
J = 2.5 Hz). CD (MeCN; c 0.00006) amax (De) 190.5 (?6.59), 210.0 (-6.29), 237.5 (?4.48)
Synthesized 1H NMR d (CDCl3, 300 MHz): 1.03 (s, 3H, 11-H), 1.27 (m, 1H, 7-H), 1.58–1.86 (m, 3H, 6-, Kitahara et al.
7-H), 1.97 (m, 2H, 5-H), 2.02 (t, J = 1.5 Hz, 3H, 60-H), 2.37 (brd, J = 15.3 Hz, 1H, 4-H), (2011), Nomura
2.73 (m, 1H, 4-H), 3.40 and 3.41 (d, J = 11.7 Hz, total 1H, 10-H), 3.57 and 3.59 (d, et al. (2013)
J = 11.7 Hz, total 1H, 10-H), 3.59–3.68 (m, 1H, 3a-H), 5.51 (d, J = 7.5 Hz, 1H, 8b-H), 6.16
and 6.17 (t, J = 1.5 Hz, total 1H, 20-H), 6.93 and 6.94 (t, J = 1.5 Hz, total 1H, 30-H), 7.43
(d, J = 1.5 Hz, 1H, 9-H). CD (MeCN) De206 - 12.1, De230 ? 23.2
Sorgolactone (CAS # 141262-39-7)
Isolated MS (m/z): 316 (C18H20O5), 219 (loss of C5H5O2), 201 (M- C5H5O2-H2O), 173 (M- C5H5O2- Hauck et al. (1992)
H2O-CO), 145 (C5H5O2-H2O-CO–CO), 97 (C5H5O2). 1H NMR (CDCl3): d 1.1, 2.0, 2.4, 2.7,
5.5, 6.1, 6.9, 7.4. CD (MeCN) De236 ? 20.0.
Synthesized MS [EI m/z, rel. intensity (%)]: 316 ([M]?, 8.1); 219 ([C13H15O3]?, 25.2); 201 ([C13H13O2]?, Sugimoto et al.
48.2); 173 ([C12H13O]?, 18.0); 97 ([C5H5O2]?, 100); 91 ([C7H7]?, 14.2). 400 MHz 1H (1997), Mori and
NMR (CDCl3): d 1.06 (d, 3H, J = 6.9 Hz, 3 9 H9); 1.26 (m, 1H, H7); 1.55 (m, 1H, H6); Matsui (1997),
1.70 (m, 1H, H6); 1.77 (m, 1H, H7); 1.94 (m, 2H. 2 9 H5); 2.03 (s, 3H, 3 9 H70 ); 2.33 (bd, Sugimoto et al.
1H, J = 15.4 Hz, H4); 2.36 (m, 1H, H8); 2.75 (dd, 1H, J = 9.0 Hz,15.4 Hz, H4); 3.61 (m, (1998)
1H, H3a); 5.49 (d, 1H, J = 7.4 Hz, H8b); 6.15 (s, 1H, H20 ); 6.92 (s, 1H, H30 ); 7.41 (d, 1H,
J = 2.6 Hz, H60 ). CD (MeCN) De230 ? 20.0. aD = 271.2 (c = 0.25, CDCl3)
Strigone (CAS # 151716-20-0)
Isolated GC–EIMS, m/z (rel. int): 344 [M]? (1), 247 (4), 230 (5), 215 (1), 97 (100). 1H NMR Kisugi et al. (2013)
(500 MHz, CDCl3) d: 1.29 (3H, s, CH3), 1.31 (3H, s, CH3), 1.84–1.95 (2H, m, H-7), 2.03
(3H, t, J = 1.5 Hz, H-70 ), 2.43–2.49 (1H, brdt, J = 5.5, 17.6 Hz, H-6a), 2.54–2.61 (1H, ddd,
J = 5.4, 10.9, 17.6 Hz, H-6b), 2.64–2.69 (1H, dt, J = 2.6, 17.2 Hz, H-4a), 2.89–2.94 (1H,
ddd, J = 0.6, 9.1, 17.2 Hz, H-4b), 3.69–3.74 (1H, m, H-3a), 5.69 (1H, brddd, J = 0.6, 2.3,
8.1 Hz, H-8b), 6.13 (1H, quin, J = 1.4 Hz, H-20 ), 6.94 (1H, quin, J = 1.6 Hz, H-30 ), 7.51
(1H, d, J = 2.6 Hz, H-60 ). CD (MeCN) De269 - 1.22, De246 ? 52.28, De227 - 5.73,
De217 ? 5.28

123
 Phytochem Rev

Table 2 continued
Compound Reference

Synthesized EI-MS m/z (rel. int.): 344 [M]? (4), 247 (7), 230 (9), 215 (3), 97 (100). 1H NMR (400 MHz, Kisugi et al. (2013)
CDCl3) d: 1.29 (3H, s, CH3), 1.31 (3H, s, CH3), 1.84–1.97 (2H, m, H-7), 2.03 (3H, t, J = 1.5
Hz, H-70), 2.46 (1H, dt, J = 17.8, 5.2 Hz, H-6a), 2.58 (1H, ddd, J = 5.6, 10.7, 17.4 Hz,
H-6b), 2.66 (1H, dt, J = 17.3, 2.7 Hz, H-4a), 2.91 (1H, dd, J = 9.3, 16.8 Hz, H-4b), 3.69-
3.74 (1H, m, H-3a), 5.69 (1H, dd, J = 1.7, 8.0 Hz, H-8b), 6.14 (1H, t, J = 1.3 Hz, H-20),
6.95 (1H, t, J = 1.6 Hz, H-30), 7.51 (1H, d, J = 2.7 Hz, H-60). CD (MeCN) De269 - 1.37,
De246 ? 23.9, De228 - 4.66, De217 ? 4.30. a20 D = ? 225 (c = 0.32 CHCl3)

5-Deoxystrigol (CAS # 151716-18-6)

Isolated EI-MS 70 eV, m/z (rel. int) 330 [M]? (4), 315 (2), 233 (16), 216 (9), 215 (18), 205 (7), 201 (9), Akiyama et al.
187 (18), 97 (100); 1H-NMR(400 MHz, CDCl3) d 1.08 (3H,s, H-9 or H-10), 1.10 (3H, s, H-9 (2005)
or H-10), 2.01 (3H, t, J = 1.5 Hz, H-70), 5.49 (1H, br.d. J = 8.0 Hz, H-8b), 6.12 (1H, m,
H-20), 6.90 (1H, m, H-30), 7.39 (1H, d, J = 2.7 Hz, CD (MeCN) De262 ? 22.86,
De230 ? 21.2
Synthesized EI-MS m/z (rel. intensity): 330 [M]? (7), 315 (3), 233 (28), 216 (16), 215 (34), 205 (8), 201 Akiyama et al.
(12), 187 (25), 97 (100). 1H NMR (400 MHz, CDCl3) d 1.09 (3H, s, Me-10), 1.10 (3H, s, (2010)
Me-9), 1.33–1.50 (2H, m, H-7), 1.63–1.71 (2H, m, H-6), 1.86–2.00 (2H, m, H-5), 2.03 (3H, t,
J = 1.6 Hz, H-70 ), 2.33 (1H, d, J = 18.0 Hz, H-4b), 2.71 (1H, dd, J = 9.0, 18.0 Hz, H-4a),
3.56–3.61 (1H, m, H-3a), 5.52 (1H, d, J = 8.0 Hz, H-8b), 6.15 (1H, m, H-20 ), 6.92 (1H, m,
H-30 ), 7.41 (1H, m, H-60 ). CD (MeCN) De262 - 1.7, De230 ? 25.7. a32 D = ? 296
(c = 0.0453, MeCN)
Fabacyl acetate (CAS # 1144514-73-7)
Isolated GC-EIMS, 70 eV, m/z (rel. int): 344 [M-60]?(1), 316 (1), 307 (3), 265 (1), 247 (21), 229 (6), Xie et al. (2009a)
205 (3), 189 (4), 97 (100). 1H NMR (400 MHz, CDCl3): d 1.02–1.05 and 1.30–1.47 (2H, m,
7-CH2), 1.16 (3H, s, 8-Me), 1.22 (3H, s, (8Me), 1.30–1.47 (2H, m,6-CH2), 1.80–1.91 (2H, m,
5-CH2), 2.02 (3H, t, J = 1.5 Hz, 70 -Me), 3.21 (1H, ddd, J = 7.3, 2.9 and 2.0 Hz, 3a-H), 4,96
(1H, d, J = 7.3 Hz, 8b-H), 5.32 (1H, d, J = 5.0 Hz, 4-H), 6.10 (1H, t, J = 1.2 Hz, 20 -H),
6.91 (1H, t, J = 1.6 Hz, 30 -H), 7.43 (1H, d, J = 2.0 Hz, 60 -H). CD (MeCN) De246 - 12.71,
De210 - 18.41. a24.2
D = ? 59.67 (c = 0.425, MeCN)
Solanacol (CAS # 953389-72-5)
Isolated 1H NMR (400 MHz, CDCl3) d 2.05 (t, 3H, J) 1.5 Hz, 40 -CH3), 2.30 (s, 3H, 8-CH3), 2.37 (s, Xie et al. (2007)
3H, 5-CH3), 3.81 (ddd, 1H, J = .3, 3.4 and 2.0 Hz, 3a-H), 5.25 (s, 1H, 4-H), 6.15 (d, 1H,
J = 7.3 Hz, 8b-H), 6.22 (t, 1H, J = 1.5 Hz, 20 -H), 6.99 (t, 1H, J = 1.5 Hz, 30 -H), 7.16 and
7.23 (AB quartet, 2H, J = 7.8 Hz, 5-H, 6-H), 7.55 (d, 1H, J = 2.4 Hz, 9-H)
Synthesized 1H NMR (300 MHz, CDCl3): d 7.55 (d, J60 ,3a = 2.6 Hz, 1H; H60 ), 7.23 (d, J6,5 = 7.7 Hz, 1H; Chen et al. (2010)
H6), 7.16 (d, J5,6 = 7.7 Hz, 1H; H5), 6.99 (t,J30 ,20 = 1.5, J30 ,70 = 1.5 Hz, 1H; H30 ), 6.22 (t,
J20 ,30 = 1.5, J20 ,70 = 1.5 Hz, 1H; H20 ), 6.15 (d, J8b,3a = 7.5 Hz, 1H; H8b), 5.25 (d,
J4,3a = 5.8 Hz, 1H; H4), 3.81 (ddd, J3a,8b = 7.5, J3a,4 = 5.8 Hz, J3a,60 = 2.6 Hz, 1H; H3a),
2.37 (s, 3H; H10), 2.30 (s, 3H; H9), 2.06 (d, 1H; OH), 2.05 ppm (t, J70 ,20 = 1.5 Hz,
J70 ,30 = 1.5 Hz,3H; H-70 ); a26
D = -164.2 (c = 2.2, CHCl3)

Solanacyl acetate (CAS # 1263309-91-6)

Isolated GC-EIMS, 70 eV, m/z (rel. int.): 384 [M]? (1), 342 (16), 245 (4), 227 (100), 184 (25), 97 (78). Xie et al. (2013)
1H-NMR (500 MHz, CDCl3) d 2.03 (s, 3H, 4-H), 2.05 (t, 3H, J = 1.5 Hz, 40 -Me), 2.30 (s,
3H, 9-Me), 2.37 (s, 3H, 10-Me), 3.86-3.88 (ddd, 1H, J = 7.3, 3.4 and 2.0 Hz, 3a-H), 6.17 (d,
1H, J = 7.3 Hz, 8b-H), 6.20 (t, 1H, J = 1.5 Hz, 20 -H), 6.35 (s, 1H, 4-H), 6.98 (t, 1H,
J = 1.5 Hz, 30 -H), 7.14 and 7.21 (AB quartet, 2H, J = 7.8 Hz, 5-H, 6-H), 7.49 (d, 1H,
J = 2.4 Hz, 60 -H). CD (MeCN) De241 - 6.33, De221 ? 6.67

123
Phytochem Rev

Table 2 continued
Compound Reference

Synthesized MS (ESI): m/z: 385.1 [M ? H]?; HRMS (ESI): m/z: calcd for C21H21O7 [M ? H]?: Chen et al. (2013)
385.1287; found: 385.1289.1H NMR (300 MHz, CDCl3): d = 7.48 (d, 1H, J = 2.4 Hz,
H60 ), 7.17 (d, 1H, J = 7.7 Hz, Har), 7.10 (d, 1H, J = 7.7 Hz, Har), 6.96 (s, 1H, H30 ), 6.32 (s,
1H, H4), 6.19 (s, 1H, H20 ), 6.14 (d, 1H, J = 7.5 Hz, H8b), 3.84 (d, 1H, J = 7.5 Hz, H3a),
2.33 (s, 3H, H7a or H8c), 2.26 (s, 3H, H7a or H8c), 2.01 (br s, 3H, H70 ), 2.00(s, 3H, H4c). 13C
NMR (75 MHz, CDCl3): d = 170.6 (C2, C4b or C50 ), 170.3 (C2, C4b or C50 ), 170.1 (C2, C4b or
C50 ), 151.5 (C60 ), 141.1 (C30 ), 139.4 (C40 , C4a, C7, C8 or C8a), 139.3 (C40 , C4a, C7, C8 or C8a),
138.5 (C40 , C4a, C7, C8or C8a), 136.4 (C40 , C4a, C7, C8 or C8a), 135.5 (C40 , C4a, C7, C8 or C8a),
132.7 (C5 or C6), 123.6 (C5 or C6), 109.7 (C3), 100.1 (C20 ), 83.9 (C8b), 79.6 (C4), 47.5 (C3a),
21.3 (C4c), 19.8 (C7a or C8c), 15.8 (C7a or C8c), 11.0 (C70 ). CD (MeCN) De241 - 6.33,
De221 ? 6.67. [a]26 D = -88.4 (c = 0.7, CHCl)

Orobanchol (CAS # 1337500-94-3)

Isolated EI-MS m/z (rel. int), 346 [M]? (4), 328 [M-H2O]? (2), 285 (8), 249 (16), 232 (41), 231 (54), Ueno et al. (2011a)
204 (39), 203 (34), 189 (21), 161 (17), 135 (10), 97 (100). 1H NMR (300 MHz,CDCl3), d
1.13 and 1.14 (each 3H, s, Me2-8), 1.37–1.51 (2H, m, H2-7), 1.66–1.74 (2H, m, H2-6),
1.81–2.01 (1H, m, H-5), 2.04 (3H, m, Me-40 ), 2.10–2.20 (1H, m, H-5), 3.42 (1H, ddd,
J = 7.4, 2.7, and 1.7 Hz, H-3a), 4.56 (1H, brs, H-4), 5.62 (1H, d, J = 7.4 Hz,H 8b),
6.18(1H, m, H-20), 6.97 (1H, m, H-30), 7.52 (1H, d, J = 1.7 Hz, H-60 ). CD (MeCN)
De242 - 1.3, De221 ? 9.5
Orobanchyl acetate (CAS # n.a.*)
Isolated LC–ESI–MS/MS, daughter ions of m/z 389, m/z (base peak intensity %), 347 (14), 329 (25), Ueno et al. (2011a)
311 (3), 265 (5), 233 (100), 232 (11), 215 (8), 205 (9), 203 (3), 187 (7), 135 (3), 107 (2), 97
(83). 1H NMR (300 MHz, CDCl3), d 1.13 and 1.16 (each 3H, s, Me2-8), 1.40-1.48 (2H, m,
H2-7), 1.60-1.72 (2H, m, H2-6), 1.86–1.96 (2H, m, H2-5), 2.04 (3H, m, Me-40 ), 2.05 (3H, s,
AcO), 3.45 (1H, ddd, J = 7.3, 2.7, and 1.7 Hz,H-3a), 5.62 (1H, d, J = 7.3 Hz, H-8b), 5.74
(1H, s, H-4), 6.16 (1H, m, H-20), 6.95 (1H, m, H-3́), 7.46 (1H, d, J = 2.7 Hz,H-60 ). CD
(MeCN) De253-1.9, De218 ? 14.4
7-Oxoorobanchol (CAS # 1256840-96-6)
Isolated GC-EIMS, 70 eV, m/z (rel. int): 360 [M]? (4), 345 (2), 263 (17), 245 (23), 218 (14), 97 (100). Xie et al. (2009b)
1H NMR (400 MHz, CDCl3): d 1.32 (3H, s, H-9), 1.35 (3H, s, H-10), 2.04 (3H, t,
J = 1.5 Hz, H-70 ), 2.31–2.51 (2H, m, 5-H), 2.42–2.78 (2H, m, 6-H), 3.58 (1H, ddd, J = 7.3,
2.4, 1.9 Hz, 3a-H), 4.48 (1H, bs, 4-H), 5.60 (1H, d, J = 7.3 Hz, 8b-H), 6.17 (1H, t,
J = 1.5 Hz, 20 -H), 6.95 (1H, t, J = 1.5 Hz, 30 -H), 7.54 (1H, d, J = 2.4 Hz, 60 -H). CD
(MeCN) De259 - 1.01, De221 ? 9.89; [a]D = -45 (c = 0.025, CHCl3)
7-Oxoorobanchyl acetate (CAS # n.a.*)
Isolated GC-EIMS, 70 eV, m/z (rel. int): 402 [M]? (1), 360 (4), 342 (11), 314 (3), 263 (9), 245 (40), Xie et al. (2009b)
228 (15), 218 (13), 97 (100). 1H NMR (400 MHz, CDCl3): d 1.31 (s, 10-Me), 1.34 (s, 9-Me),
2.03 (s, 200 -Me), 2.04 (t, J = 1.5 Hz, 70 -Me), 2.29-2.54 (m, 5-CH2), 2.42-2.77 (m, 6-CH2),
3.56 (ddd, J = 7.3, 2.4, 1.9 Hz, 3a-CH), 5.60 (d, J = 7.3 Hz, 8b-CH), 5.82 (bs, 4-CH), 6.17
(t, J = 1.5 Hz, 20 -CH), 6.95 (t, J = 1.5 Hz, 30 -CH), 7.56 (d, J = 2.4 Hz, 60 -CH). CD
(MeCN) De252 - 8.23, De220 ? 52.71; [a]D = -58 (c 0.023, CHCl3)

Hence, inspection of the CD spectra of 7-oxoorob-
anchol and its acetate (Xie et al. 2009b; supplemental
material) reveals that they are two ‘‘derivatives’’ of
(-)-orobanchol belonging to the orobanchol-like class
of SLs (Fig. 1). Finally, it can be concluded that all
4-OR-SLs probably have stereochemistry in accor-
dance with (-)-orobanchol.
Natural SLs contain 3–5 stereogenic centers and
4–16 stereoisomers are conceivable. Recent findings
suggest that plants may produce all SL stereoisomers,
but only those produced in larger amounts or that
accumulated in root exudates have been isolated and
identified. It has been suggested that plants produce
more than 100 SLs, including conjugates and stereo-
isomers (Zwanenburg et al. 2009; Vurro and Yoney-
ama 2012). The stereochemistry of SLs is of high
importance for their biological activity, such as
germination of parasitic weeds and hyphal branching.
A better understanding of stereochemistry of SLs will
be instrumental for designing strategies to fine-tune

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Table 3 Transitions of m/z for known SLs

Compound Transition (m/z) Reference

Strigol 369 [M ? Na]? [ 272 [M ? Na-C5H5O2]? Sato et al. (2003)

Orobanchol 369 [M ? Na]? [ 272 [M ? Na-C5H5O2]? Sato et al. (2003), Yoneyama
et al. (2011)
Strigyl acetate 411 [M ? Na]? [ 254 [M ? Na-CH3COOH]?, Sato et al. (2005), Yoneyama
411 [M ? Na]? [ 307 [M ? Na-CH3COOH- C5H5O2]? et al. (2011)
5-Deoxystrigol 353 [M ? Na]? [ 256 [M ? Na-C5H5O2]? Yoneyama et al. (2007a, 2007b)
Sorgolactone 339 [M ? Na]? [ 242 [M ? Na-C5H5O2]? Yoneyama et al. (2008)
Solanacol 365 [M ? Na]? [ 268 [M ? Na-C5H5O2]? Yoneyama et al. (2008)
Didehydroorobanchol 367 [M ? Na]? [ 270 [M ? Na-C5H5O2]? Yoneyama et al. (2008)
Dehydrostrigol 367 [M ? Na]? [ 270 [M ? Na-C5H5O2]? Yoneyama et al. (2008)
Sorgomol 369 [M ? Na]? [ 272 [M ? Na-C5H5O2]? Yoneyama et al. (2008)
? ?
7-Oxoorobanchol 383 [M ? Na] [ 286 [M ? Na-C5H5O2] Yoneyama et al. (2008)
Orobanchyl acetate 411 [M ? Na]? [ 254 [M ? Na-CH3COOH]? Yoneyama et al. (2008)
7-Hydroxyorobanchol 385 [M ? Na]? [ 288 [M ? Na-CH3COOH]? Yoneyama et al. (2011)
Fabacol 385 [M ? Na]? [ 254 [M ? Na-CH3COOH]? Yoneyama et al. (2011)
7-Oxoorobanchyl acetate 425 [M ? Na]? [ 268 [M ? Na-CH3COOH-C5H5O2]? Yoneyama et al. (2011)
? ?
Fabacyl acetate 427 [M ? Na] [ 270 [M ? Na-CH3COOH-C5H5O2] Yoneyama et al. (2011)
7-Hydroxyorobanchyl acetate 427 [M ? Na]? [ 270 [M ? Na-CH3COOH-C5H5O2]? Yoneyama et al. (2011)

1
Table 4 H NMR chemical shifts of basic skeleton of SLs Germination stimulation
Strigolactone skeleton Proton d (ppm)
Almost 50 years ago, SLs were identified as germi-
1
O 3a 3.60–3.70 nation stimulants of root parasitic plants, particularly
O
2 4 2.60–2.75
8 8a
8b 3 the species belonging to the Striga, Orobanche and
7
6`
5 1.90–2.00 Phelipanche genera (Bouwmeester et al. 2003;
6 3a
5 4a 4
1` 6 1.50–1.70 Hristeva et al. 2013; Rasmussen et al. 2013) that
O 2` O
5` 7 1.70–1.90 affect many important food crops. These parasites
O
3`
8 2.30–2.40 attach themselves to the roots of many plants and
4`

CH3
8b
20
0
3 6.85–6.95
40 -CH3
60
the strigolactone composition in a plant and identify-
ing plant species that are producing either large or low
amounts of SLs. This would enable plant breeders to
select varieties that, for example, do produce root
exudates that facilitate AM symbiosis and control
shoot branching, but do not induce parasitic plant seed
germination. In order to correctly refer to the sub-
stances their stereochemistry should be stated. Chir-
optical properties are of utmost importance to assign
the correct stereochemistry at the respective stereo-
genic centers in SLs.
5.30–5.50 acquire nutrients and water from their hosts, causing
6.10–6.20 severe crop loses in many parts of the world (Yoney-
ama et al. 2010; Parker 2009, 2012). Typical features
2.00–2.10 of the life cycle of these parasites are that they produce
7.40–7.50 many very small seeds that these seeds remain viable
in the soil for 15–20 years (Grenz and Sauerborn
2007; Kgosi et al. 2012; Parker 2012). Once germi-
nation has been triggered, the radicle of the germinat-
ing seed attaches itself to the host root and forms a
haustorium. The parasite develops flowers and pro-
duces a large number of seeds (Bebawi et al. 1984;
Cardoso et al. 2011; Yoneyama et al. 2013).
In general, all SLs showed germination activity
toward root parasitic plants belonging to the Striga,
Orobanche and Phelipanche families, in most of cases
they are even 100 times fold more active than the
synthetic analogue GR24 (Table 5). Kim et al. (2010)

123
Phytochem Rev
found that the germination-stimulating activity of
naturally occurring SLs on O. minor seeds depend on
the lipophilicity of SL molecules. SLs having a
hydroxyl group revealed the highest overall activity,
whilst their acetates show a slightly weaker response.
All SLs induced[80 % germination of O. minor seeds
at B1 nM, while GR24 elicits [60 % germination at
100 nM Ueno et al. (2011b) examined germination
induction of natural SLs and their synthetic analogues
and they suggest that both an oxygenated substituent at
C-4 and the configuration of the tricyclic lactone and
the D-ring are essential structural requirements for
inducing germination.
In addition, Nomura et al. (2013) reported the
germination activity of all stereoisomers of sorgolac-
tone, orobanchol, sorgomol, and 5-deoxystrigol
toward S. hermonthica and S. gesnerioides seeds. All
compounds induced S. hermonthica seed germination,
but exerted different response, comparable with those
reported by Ueno et al. (2011b) for O. minor. It should
be noted that only a limited number of these SLs
induced significant germination in S. gesnerioides,
thus indicating strict structural requirements for these
seeds. In general, weedy broomrape species (O. minor,
O. crenata, P. ramosa, etc.) are less specialized in
germination requirements than the non-weedy species
(O. ballotae, O. alba, P. schultzii, etc.), (Whitney
1978; Parker 2009; Fernandez-Aparicio et al. 2011).
Extensive studies on the mode of action of SLs in
germination stimulation of parasitic plant seeds are
still under active investigation and extensive further
research is needed to shed light on this important
bioprocess.
An inspection of the data presented in Table 6
reveal that germination stimulation of SLs on seeds of
one parasitic plant may be different from that of
another species (Yoneyama et al. 2009; Kim et al.
2010; Nomura et al. 2013). In addition, they may
exhibit different response in different germination
assays. The standardized germination bioassay
described by Mangnus et al. (1992) is used by many
authors who evaluate the biological activity of
potential germination stimulants. Notably, Matusova
et al. (2004) as well as Song et al. (2005) observed that
the temperature during preconditioning of some
Orobanche and Striga seeds strongly affected the
response of the seeds to the applied germination
stimulant. This may be a reason why different results
concerning germination activity have been reported. It
should be noted that the origin of the seeds may play a
role as well. Recently Pouvreau et al. (2013) reported
new simple and accurate method for germination rate
determination based on a standardized 96-well plate
test coupled with spectrophotometric reading of
tetrazolium salt (MTT) reduction.
Since parasitic weeds are entirely dependent on
their host to survive and develop, an attractive
approach for the control of parasitic weeds is to
interfere with the intimate relationship between host
and parasitic plants. Stimulating germination in the
absence of a host plant will kill the germinated seeds
and hence reduce the seed population in the soil. This
concept of suicidal germination (Zwanenburg et al.
2009; Kgosi et al. 2012) has attracted at significant
attention (Kondo et al. 2007; Zwanenburg et al. 2009;
Zwanenburg and Pospisil 2013). Very recently Kannan
and Zwanenburg (2014) suggested novel concept by
decomposing germination stimulants prior to action no
germination of seeds can take place anymore. They
used borax and thiourea in natural conditions that
promote decomposition of SLs and as a consequence
not allow the parasitic weeds to germinate.
Hyphal branching
Recently, SLs were identified as a communication
molecule between arbuscular mycorrhizal (AM) fungi
and plant roots (Akiyama et al. 2005, 2010). In this
fungal-plant symbiotic relationship, the AM fungi
provide phosphate and bring water to the plant in
return for carbon. SLs exuded by roots stimulate AM
fungi hyphal branching allowing them to grow
towards the plant roots involved. The fungi get
carbohydrates from the higher plants and supply them
with nutrients from the soil. AM fungi have also been
reported to protect the host plants against draught and
pathogen attack (Bever et al. 2001; Quilambo 2003;
Smith et al. 2011). It has been suggested that plants
have evolved to produce SLs in order to enable AM
fungi to colonize their roots and that parasitic plants
are taking advantage of these host-presence signaling
molecules to help them sensing the vicinity of a host as
well (Akiyama et al. 2005; Bouwmeester et al. 2007;
Yoshida et al. 2012; Foo et al. 2013).
Although there is not much literature concerning
structure–activity relationship of SLs as branching
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 Phytochem Rev

Table 5 An overview on SLs where information is available on their germination activity toward parasitic weeds, as well as for their
synthetic analogue GR24
Compound Parasitic plant (germination activity) Reference

Strigol Striga hermonthica (40 % 10 nM, 70 % Yasuda et al. (2003), Nomura et al. (2013)
1 mM)
Striga asiatica Siame et al. (1993)
Striga gesnerioides (10 % 10 nM, 40 % Nomura et al. (2013)
1 mM)
Striga lutea (50 %100 pM) Cook et al. (1972)
Orobanche minor (90 %1–100 nM, Yokota et al. (1998), Sato et al. (2005), Awad et al. (2006), Xie
18 %10 pM) et al. (2007, 2008b), Kim et al. (2010)
Orobanche ramosa (80 %1 nM) Xie et al. (2008b)
Phelipanche ramosa (79 %1 nM, Xie et al. (2007)
12 %10 pM)
Strigyl acetate Orobanche minor (90 % 1 lM 90 %; Sato et al. (2005), Xie et al. (2008b)
1 nM)
Orobanche ramosa (90 % 1 nM) Xie et al. (2008b)
5-Deoxystrigol Striga hermonthica (70 % 10–100 nM, Yoneyama et al. (2007a), Sugimoto and Ueyama (2008),
80 % 1 mM, 45 % 10 mM) Umehara et al. (2008), Jamil et al. (2013), Ueno et al. (2011b),
Nomura et al. (2013)
Striga gesnerioides (5 % 10 nM, 5 % Ueno et al. (2011b), Nomura et al. (2013)
1 mM; 1 % 10 nM)
Orobanche minor (76 % 10 mM, 60 % Awad et al. (2006), Yoneyama et al. (2008), Sugimoto and
1 lM) Ueyama, (2008), Kim et al. (2010), Ueno et al. (2011b), Xie
et al. (2013)
Orobanche crenata (45 % 10 lM) Sugimoto and Ueyama, (2008)
5-Deoxystrigol Striga hermonthica
Solanacol Orobanche minor (90 % 1nM, 10 pM Xie et al. (2007), Yoneyama et al. (2008), Kim et al. (2010), Xie
14 %) et al. (2013)
Orobanche ramosa López-Ráez et al. (2008)
Phelipanche ramosa (82 % 1nM, 10 pM Xie et al. (2007), Koltai et al. (2011)
14 %)
Sorgolactone Striga hermontica (40 % 10 nM, 60 % Nomura et al. (2013)
1 mM)
Striga gesnerioides (2 % 10 nM, 5 % Nomura et al. (2013)
1 mM)
Orobanche minor (92 % 10 nM) Kim et al. (2010)
Sorgomol Striga hermonthica (50 % 20 pM, 50 % Xie et al. (2008a), Jamil et al. (2013), Nomura et al. (2013)
10 nM, 80 % 1 mM)
Striga gesnerioides (20 % 10 nM, 35 % Nomura et al. (2013)
1 mM)
Orobanche minor (50 % 2 nM) Xie et al. (2008a), Kim et al. (2010), Yoneyama et al. (2011),
Jamil et al. (2013)
Strigone Striga hermonthica (100 % 0.01 nM) Kisugi et al. (2013)
Orobanche minor (90 % 100 nM); Kisugi et al. (2013)
Phelipanche ramosa (90 % 1 nM 90 %) Kisugi et al. (2013)
Fabacyl acetate Orobanche minor (90 % 10 nM) Kim et al. (2010), Yoneyama et al. (2011)

123
Phytochem Rev
Table 5 continued
Compound Parasitic plant (germination activity)
Orobanchol Striga hermonthica (40 % 10 mM, 50 %
10 nM, 80 % 1 mM)
Striga gesnerioides (0 % 10 mM, 30 %
10 nM, 35 % 1 mM)
Orobanche minor (90–95 % 1 nM,
15–54 % 1 pM, 72 % 10 mM)
Orobanche aegyptiaca
Orobanche ramosa (70–80 % 1 nM,
20 % 10 pM)
Phelipanche ramosa (84 % 1 nM 84 %,
32 %10 pM)
7-Oxoorobanchol Orobanche minor (76-90 % 1 nM)
7-Oxoorobanchyl Orobanche ramosa (80 % 1 nM)
acetate Orobanche minor (90 % 1 nM)
7-Hydroxyorobanchyl Orobanche minor
acetate
Orobanchyl acetate Striga hermonthica (45 % 10 mM)
Striga gesnerioides (0 % 10 mM)
Orobanche minor (70–80 % 10 nM, 5 %
10 pM, 70 % 10 mM)
Orobanche ramosa 20–80 % 1 nM;
20 % 100 pM
GR 24 Striga hermonthica (60 % 0.34 mM,
50 % 10 mM)
Striga gesnerioides (1 % 10 mM)
Orobanche minor (83 % 1 lM,
9 %10 nM, 63 % 10 mM)
Orobanche aegyptiaca (80 % 1 lM)
Phelipanche ramosa (52–90 % 100 pM,
35–60 %10 pM, 83 % lM, 24 %
100 nM)
factors for AM fungi (Akiyama et al. 2005; Besserer
et al. 2006, 2008; Akiyama et al. 2010), some
correlations have been postulated (Akiyama et al.
2010; Boyer et al. 2012; Zwanenburg and Pospisil
2013). It has been suggested that the induction of
hyphal branching in AM fungi proceeds via a receptor-
mediated mechanism, but details are lacking.
The structural requirements of SLs as hyphal
branching factor in AM fungi are similar but not
identical to those observed for germination of seed of
root parasitic weeds, especially with regard to the enol
Reference
Jamil et al. (2011a, b), Foo and Davies (2011), Ueno et al.
(2011a, b), Yoneyama et al. (2012), Nomura et al. (2013)
Matsuura et al. (2008), Ueno et al. (2011a, b), Nomura et al.
(2013)
Yokota et al. (1998), Awad et al. (2006), Yoneyama et al.
(2007b), Xie et al. (2007), Yoneyama et al. (2008), Xie et al.
(2008b, 2009b), Akiyama et al. (2010), Kim et al. (2010),
Yoneyama et al. (2011), Ueno et al. (2011a, b), Xie et al.
(2013)
Goldwasser et al. (2008)
Xie et al. (2008b, 2009b)
Xie et al. (2007)
Xie et al. (2009b), Kim et al. (2010)
Xie et al. (2009b)
Xie et al. (2009b), Kim et al. (2010), Yoneyama et al. (2011)
Yoneyama et al. (2011)
Ueno et al. (2011a, b)
Ueno et al. (2011a, b)
Yoneyama et al. (2008), Xie et al. (2008b, 2009b), Kim et al.
(2010), Yoneyama et al. (2011), Ueno et al. (2011a, b), Xie
et al. (2013)
Xie et al. (2008b, 2009b), Ueno et al. (2011b)
Mangnus et al. (1992), Wigchert and Zwanenburg (1999),
Yasuda et al. (2003), Daws et al. (2008), Ueno et al. (2011b)
Ueno et al. (2011b)
Goldwasser et al. (2008), Kim et al. (2010), Ueno et al. (2011b)
Goldwasser et al. (2008)
Xie et al. (2007), López-Ráez et al. (2011), Aroca et al. (2013)
ether bridge in the C–D part of the SL molecules. The
data shown in Table 6, reveal that hyphal branching
activity of AM fungus varies significantly with the
substitution pattern in the AB-moiety of SLs. More-
over, Akiyama et al. (2010) showed that stereochem-
istry plays important role, namely that natural SLs are
more active than their enantiomers. In addition, the
hyphal branching inducers differed not only in the
active concentration but also in the branching pattern
of hyphae they induced. It is relevant to shed more
light on the structure–activity relationship of SLs in
123
 Phytochem Rev

Table 6 An overview on SLs where information is available on their hyphal branching activity toward mycorrhizal fungi, as well as
for their synthetic analogue GR24
Compound Mycorrhizal fungi (hyphal branching activity) Reference

Strigol Gigaspora margarita (100 pg MEC) Akiyama et al. (2010)

5-Deoxystrigol Gigaspora margarita (3-100 pg MEC) Akiyama et al. (2005, 2010), Yoneyama et al. (2008)
20 -epi-5-Deoxystrigol Gigaspora margarita (30 pg MEC) Akiyama et al. (2010)
Sorgomol Gigaspora margarita (100 pg MEC) Akiyama et al. (2010)
Sorgolactone Gigaspora margarita (30 pg MEC) Akiyama et al. (2010)
Gigaspora rosea (10 fM) Besserer et al. (2006)
7-Oxoorobanchyl acetate Gigaspora margarita (10 pg MEC) Akiyama et al. (2010)
Dehydroorobanchol Glomus mosseae López-Ráez et al. (2011)
Glomus intraradices Koltai et al. (2010), López-Ráez et al. (2011)
Gigaspora margarita Yoneyama et al. (2008)
Fabacyl acetate Glomus intraradices Foo (2013)
Gigaspora margarita (10 pg MEC) Yoneyama et al. (2008), Akiyama et al. (2010)
Solanacol Glomus mosseae López-Ráez et al. (2011)
Glomus intraradices Koltai et al. (2010), López-Ráez et al. (2011).
Gigaspora rosea Yoneyama et al. (2008)
Gigaspora gigantea
Orobanchol Gigaspora margarita (1 pg MEC) Yoneyama et al. (2008), Akiyama et al. (2010)
Glomus intraradices Foo (2013)
Orobanchyl acetate Gigaspora margarita (10 pg MEC) Yoneyama et al. (2008), Akiyama et al. (2010)
GR 24 Gigaspora margarita (100 pg MEC) Akiyama et al. (2010)
Gigaspora rosea (100 fM) Besserer et al. (2006)

their action as branching factors for AM fungi. Having
this information will allow to rationally design active
synthetic SL analogue for this branching activity.
Biosynthesis and phytohormonal functions
In 2005 it was postulated that SLs are produced via
carotenoid biosynthetic pathway (Matusova et al.
2005), with carotenoid cleavage dioxygenase
involved. Alder et al. (2012) as well as Uehara and
Ashikari (2013) reported the biosynthesis of carlac-
tone from b-carotene, a compound with strigolatone-
like biological activities, such as induction of seed
germination and tillering, that might be synthetic
precursor of SLs. Scaffidi et al. (2013) reported the
chemical synthesis of carlactone, and showed that it
represses Arabidopsis shoot branching and influences
leaf morphogenesis, but also exhibited weak activity
in seedlings. Their results raise important questions
about the pathways by which butenolides are produced
to control various aspects of plant development. Very
recently Seto et al. (2014) synthesized 13C-labeled
carlactone and showed its conversion to (-)-[13C]-20 -
epi-5-deoxystrigol and [13C]-orobanchol, endogenous
SLs in rice. Their data provide evidence that carlac-
tone is an endogenous SL precursor that is stereospe-
cifically recognized in the biosynthesis pathway.
After biosynthesis, SLs pool in the root, leaves the
root through exudation and enters the rhizosphere,
there they act as signaling compounds (Ruyter-Spira
et al. 2013). Levels of SLs in roots are significantly
increased in a number of plant species when plants are
grown under Pi deficient conditions (Yoneyama et al.
2007a, b, 2012; Jamil et al. 2011b; Czarnecki et al.
2013). Because Pi deficiency stimulates SL biosyn-
thesis, one would expect that similar phenotypic
changes are observed in plants grown under Pi
deficient conditions and SL-treated plants. It was
found that elevated SL levels in plants grown under Pi
deficient conditions are normally accompanied by a
suppression of bud outgrowth and shoot branching
(Umehara et al. 2008, 2010; López-Ráez et al. 2008),
one of the best characterized phenotypic traits

123
Phytochem Rev
regulated by SLs. Pi starvation promotes lateral root
formation and elongation (Peret et al. 2011). This
effect is much weaker in MAX1 and MAX2, SL-
deficient and SL-insensitive mutants, respectively,
suggesting that endogenous SLs stimulate rapid
growth of lateral roots in response to the Pi starvation.
In contrast, SLs exert inhibitory effects on lateral root
formation under normal Pi-sufficient conditions
(Ruyter-Spira et al. 2011; Kapulnik et al. 2011b). In
addition, Agusti et al. (2011) reported the involvement
of SLs in the control of secondary growth, i.e. SLs
induce secondary development that is mainly down-
stream of auxin. Therefore, in contrast to cytokinin
that promote outgrowth of axillary buds (Ongaro and
Leyser 2008), SLs were found to inhibit shoot
branching (Schachtschabel and Boland 2009; Dun
et al. 2009; Rameau 2010). Moreover, de Saint et al.
(2013b) found that SLs act independently from
gibberellins to stimulate internode elongation. Also
there are some speculations that SLs are involved in
the control of senescence (Seto et al. 2012).
Since SLs are classified as long-sought, carotenoid-
derived shoot-branching inhibitors (Gomez-Roldan
et al. 2008; Umehara et al. 2008) their hormonal
functions likely predate the evolution of the signaling
role in the rhizosphere (Delaux et al. 2012). Evidence
is rapidly accumulating that SLs contribute to a
number of crucial processes in plant growth and
development, namely in the shaping of plant archi-
tecture. Moreover, Koltai (2011) suggested the possi-
bility that the SLs might play a part in plant
morphogenesis, rather than in plant communication.
Conclusion
Strigolactones released from plant roots induce seed
germination of root parasitic weeds, Striga spp.,
Orobanche spp. and Phelipanche spp., and hyphal
branching of symbiotic arbuscular mycorrhizal (AM)
fungi. In addition to these functions in the rhizosphere,
strigolactones have recently been shown to be a novel
class of plant hormones regulating bud outgrowth and
shoot branching. Important advances in knowledge
about the identity, occurrence, biological function and
physiological and biochemical regulation of the strig-
olactones have been reported. Due to the better
understanding of their activities, the emphasis in this
review has been given on a collection of available data
and revision of the structures of some strigolactones,
especially from stereochemical point of view. It has to
be pointed that there are still missing data for
methoxy-5-deoxystrigol, 7-hydroxyorobanchol, and
7-hydroxyorobanchol acetate. It seems appropriate to
provide these data to the scientific community that is
investigating these novel plant hormones.
Acknowledgments This work was supported by the grant
LO1204 from the National Program of Sustainability I and OP
ECOP grant CZ.1.07/2.4.00/30.0041 (POSTUP II) from the
Ministry of Education Youth and Sports, Czech Republic.
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