Phytochemical studies on the Australian native plant species Acacia pycnantha and Jacaranda mimosifolia D.Don*

Article abstract of DOI:10.1080/14786419.2018.1483922

In ongoing investigations into colours in Nature, the chemical constituents from the flowers of Acacia pycnantha and Jacaranda mimosifolia D.Don grown in Australia are reported. Eight known secondary metabolites were isolated from the A. pycnantha flower including isosalipurposide (7) which may be responsible for their distinctive colouration. Nine secondary metabolites were isolated from the J. mimosifolia D.Don flower including the new phenylethanoid β-D-glucopyranose (10). All isolated compounds were inactive against bacteria tested at concentration of 32?μg/mL.

Full text of DOI:10.1080/14786419.2018.1483922

Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
Phytochemical studies on the Australian native
plant species Acacia pycnantha and Jacaranda
mimosifolia D.Don
Rudi Hendra, Anthony Willis & Paul A. Keller
To cite this article: Rudi Hendra, Anthony Willis & Paul A. Keller (2018): Phytochemical studies on
the Australian native plant species Acacia pycnantha and Jacaranda mimosifolia D.Don, Natural
Product Research, DOI: 10.1080/14786419.2018.1483922
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Natural Product research, 2018
ꢁꢁpꢂ://ꢃꢄi.ꢄꢅg/10.1080/14786419.2018.1483922
ꢀ
Phytochemical studies on the Australian native plant species
Acacia pycnantha and Jacaranda mimosifolia D.Don*
a
b
a
Rudi Hendra , Anthony Willis and Paul A. Keller
ꢆsꢇꢀꢄꢄꢈ ꢄf cꢀꢉmiꢂꢁꢅy, univꢉꢅꢂiꢁy ꢄf Wꢄꢈꢈꢄngꢄng, Wꢄꢈꢈꢄngꢄng, aꢊꢂꢁꢅꢆꢈiꢆ; brꢉꢂꢉꢆꢅꢇꢀ sꢇꢀꢄꢄꢈ ꢄf cꢀꢉmiꢂꢁꢅy,
aꢊꢂꢁꢅꢆꢈiꢆn Nꢆꢁiꢄnꢆꢈ univꢉꢅꢂiꢁy, cꢆnbꢉꢅꢅꢆ, aꢊꢂꢁꢅꢆꢈiꢆ
ABSTRACT
ARTICLE HISTORY
rꢉꢇꢉivꢉꢃ 6 Jꢆnꢊꢆꢅy 2018
aꢇꢇꢉpꢁꢉꢃ 29 Mꢆy 2018
In ongoing investigations into colours in Nature, the chemical
constituents from the flowers of Acacia pycnantha and Jacaranda
mimosifolia D.Don grown in Australia are reported. Eight known
secondary metabolites were isolated from the A. pycnantha flower
including isosalipurposide (7) which may be responsible for their
distinctive colouration. Nine secondary metabolites were isolated from
the J. mimosifolia D.Don flower including the new phenylethanoid
β-D-glucopyranose (10). All isolated compounds were inactive against
bacteria tested at concentration of 32 μg/mL.
KEYWORDS
Acacia pycnantha; Jacaranda
mimosifolia d.dꢄn;
flꢆvꢄnꢄiꢃꢂ; pꢀꢉnyꢈꢉꢁꢀꢆnꢄiꢃ;
ꢆnꢁibꢆꢇꢁꢉꢅiꢆꢈ
1
. Introduction
Australia has a hugely variable climate with arid, tropical, desert, alpine, and extreme con-
ditions encompassed within the country. Australian plants have therefore developed a wide
variety of survival methods specific to their environmental challenges, resulting in numerous
unique morphologies and phenotypes present. A large range of introduced species have
also adapted to the environment with many also cultivated (Lassak and McCarthy 2011).
CONTACT Pꢆꢊꢈ a. Kꢉꢈꢈꢉꢅ
rꢉꢂꢉꢆꢅꢇꢀ ꢊnꢃꢉꢅꢁꢆkꢉn ꢆꢁ ꢁꢀꢉ univꢉꢅꢂiꢁy ꢄf Wꢄꢈꢈꢄngꢄng.
kꢉꢈꢈꢉꢅ@ꢊꢄw.ꢉꢃꢊ.ꢆꢊ
*
sꢊppꢈꢉmꢉnꢁꢆꢈ ꢃꢆꢁꢆ fꢄꢅ ꢁꢀiꢂ ꢆꢅꢁiꢇꢈꢉ ꢇꢆn bꢉ ꢆꢇꢇꢉꢂꢂꢉꢃ ꢀꢁꢁpꢂ://ꢃꢄi.ꢄꢅg/10.1080/14786419.2018.1483922.
©
2018 Infꢄꢅmꢆ uK limiꢁꢉꢃ, ꢁꢅꢆꢃing ꢆꢂ tꢆyꢈꢄꢅ & Fꢅꢆnꢇiꢂ Gꢅꢄꢊp

2
R. HENDRA ET AL.
Numerous endogenous plants have been used as traditional medicines, however their pur-
ported biological effects are largely based on anecdotal evidence.
Acacia pycnantha (Fabaceae), commonly known as the golden wattle, is native to New
South Wales, Victoria, and South Australia and has been Australia’s national flower since
1988, and growing from 3 to 8 meters in height (Ndlovu et al. 2013). The bark of this species
is generally dark brown to grey and the mature trees have phyllodes (flat and widened leaf
stems) which hang down from the branches. The bright yellow flowers occur in groups of
40 to 80 on 2.5–9 cm long raceme, which arise from auxiliary buds (Wilson et al. 2001; Ndlovu
et al. 2013). This species typically flowers between November and May, though they may
additionally flower several months later (Wilson et al. 2001; Ndlovu et al. 2013).The Indigenous
Australian people used this genus in traditional medicines and fibre craft, as well as an
adhesive and as utensils (Barr et al. 1988; Murphy 2008; Clarke 2012), with its seeds also
playing an important role in the diet as they are easily ground to a flour which can be mixed
with water and eaten either raw or cooked to produce a type of unleavened bread (Hegarty
et al. 2001). Several species such as A. kempeana, A. tetragonophylla from this genus have
been reported to be prepared as antimicrobial agents (Hegarty et al. 2001), with a water
extract from the leaves of A. pycnantha inhibiting 97% larval development and showed
anthelmintic activity toward equine cyathostomins in vitro (Payne et al. 2013). This genus is
also a valuable commercial commodity, important in the flowering garden plants industry.
Despite the historical and current commercial prominence, there are no phytochemical or
traditional medicine studies on the flowers of this species.
J. mimosifolia D.Don belongs to the Bignoniaceae family, and is native to Brazil. It has
been cultivated in both tropical and subtropical areas of the world, and naturalised in many
countries for its beautiful foliage and flowers (Moharram and Marzouk 2007; Zaghloul et al.
2011), including in Australia where it is cultivated as an ornamental plant. It is a tree ranging
from 1 to 45 meters tall with blue flowers which bloom in summer and are up to 5 cm long,
and grouped in 30 cm panicles. The fruits of this species are oblong capsules, flattened
perpendicular to the septum, and the valves either glabrous or lepidote, possessing numer-
ous seeds. The genus of Jacaranda is commonly known as pioneer trees, because the seeds
are easily grown in different climates (Gachet et al. 2010). It is diverse in its biological activities
and the chemical constituents differ in species within this genus. Jacaranone and pheny-
lethanoids are commonly isolated from examples within this genus, with the former isolated
from the leaves of J. mimosifolia D.Don along with scutellarein 7-glucuronide, verbascoside,
and phenylacetic β-glucoside (Moharram and Marzouk 2007; Mostafa et al. 2014).
We have an ongoing interest in colours from Nature, concentrating particularly on flowers
of plants that are both endemic and introduced to Australia (Hendra and Keller 2016, 2017),
as well as any relationship between the isolated compounds and Indigenous uses. Here, we
report the phytochemical studies and the antimicrobial activities of the flowers of plants
species which are commonly found in the Wollongong (Australia) region. These species were
selected due to their abundance, and lack of information regarding the chemical constituents
present, including those responsible for their colouration.
2
. Results and discussion
Methanol extractions of the flowers of A. pycnantha was concentrated and sequentially
solvent-partitioned into n-hexane:MeOH resulting in polar and non-polar fractions. The

NATURAL PRODUCT RESEARCH
3
(
A)
(
B)
Figure 1. Mꢄꢈꢉꢇꢊꢈꢆꢅ ꢂꢁꢅꢊꢇꢁꢊꢅꢉꢂ ꢄf ꢇꢄmpꢄꢊnꢃꢂ iꢂꢄꢈꢆꢁꢉꢃ fꢅꢄm ꢁꢀꢉ flꢄwꢉꢅꢂ ꢄf A. pycnantha (1–8) (A) ꢆnꢃ J.
mimosifolia d.dꢄn (9 – 17) (B).
chemical constituents from the non-polar fraction were analysed using GC-EIMS. The polar
fractions from both species were subjected to analytical RP-HPLC followed by semi-prep
RP-HPLC, which resulted in the isolation of eight compounds (Figure 1(a)).
The water-acetonitrile mixture containing compounds 1 (Velozo et al. 1999) and 2 (Ibrahim
et al. 2007; Shimoda et al. 2010), was subjected to slow evaporation at room temperature,
and afforded 1 as long white-needle crystals, with 2 isolated from the filtrate after solvent
evaporation. Analysis of the LRESMS spectra of 1 indicated peaks at m/z 457 and 433,
+
-
1
assigned to [M+Na] and [M-H] respectively. H NMR spectroscopic analysis showed two
resonances at δ 5.29 (dd, J = 13.0; 3.1 Hz), 2.97 (dd, J = 17.2; 3.0 Hz) and 2.75 (dd, J = 17.2;

4
R. HENDRA ET AL.
3.0 Hz) assigned to the methylene protons (H-2 & H-3), respectively suggesting the presence
of a flavanone. Furthermore, a doublet at δ 4.75, with a coupling constant of 7.2 Hz, was
assigned to the anomeric proton of a glucosyl, indicating the β-configuration of the glucose
moiety and the remaining proton resonances in the δ 3.45–4.03 range assigned to the sugar
moiety (Table S1, Figure S3, Supplementary Material). gHMBC analysis showed correlation
between the resonance at δ 4.75, assigned to the H-1″ anomeric proton, and the oxygenated
H
carbon resonance at δ 162.1 (C-5) (Figure S27).
C
2
2
Compound 1 was optically active with a specific rotation value of [ꢀ] + 29.52 (MeOH)
D
–
the absolute configuration was determined by comparative electronic circular dichroism
(
ECD) spectroscopy with a positive cotton effect observed at 334 nm (Δε + 0.86) and a neg-
ative cotton effect at 290 nm (Δε −2.97), indicating a 2S configuration, consistent with that
reported (334 nm (Δε + 1.10) and 290 nm (Δε −3.88) (Tyukavkina et al. 1989). Finally, the
absolute configuration of compound 1 was confirmed from the analysis of its single crystal
X-ray crystallographic data. The refined Hooft parameter was −0.04 (8) for 1026 Friedel-pairs
and the bond lengths and angles between fused ring C and B was observed at 104.6° by
using Spartan version 16 (supporting information, F26) Therefore it was confirmed a (2S)
configuration (Figure S26) and compound 1 was identified as (2S)-naringenin
5-O-β-D-glucopyranose.
Analysis of the spectroscopic data of compound 2 revealled similarities to compound 1,
however gHMBC analysis showed a correlation between the resonance at δ 4.75 (d,
H
J = 9.8 Hz), assigned to the H-1″ anomeric proton, and the carbon resonance at δ 106.1
C
(C-8), indicating a C–C bond link between naringenin to the glucosyl anomeric proton (Figure
S27), with 2 identified as isohemiphloin (Hillis and Horn 1965). It was also optically active
2
2
with a specific rotation of [ꢀ]D 97.79 (MeOH), and further analysis of the ECD spectrum
indicated a positive cotton effect at 334 nm (Δε + 2.80) and a negative cotton effect at 290 nm
(Δε −4.06) (Xiao et al. 2012). Compound 8 was identified as the parent heterocycle naringenin
and was spectroscopically identical to that reported (Shimoda et al. 2010). In the same
manner, compound 8 showed 2S absolute configuration with positive cotton effect at
334 nm (Δε + 1.39, lit Δε + 0.89 (Caccamese et al. 2005)) negative cotton effect at 287 nm
(
Δε −6.07, lit Δε −4.20 (Caccamese et al. 2005)).
During the isolation procedure, compounds 3, 4, and 5 (Kazuma et al. 2003) were collected
as one fraction, and required re-separation by preparative RP-HPLC, affording myricetin
-rhamnodise (3), quercetin 3-glucoside (4), and kaempferol 3-rutinoside (5). The two major
3
constituents contained within the flowers were isolated at t 15.0 (6) and 17.8 (7) minutes
R
with compound 6 assigned as kaempferol-3-rhamnoside (Güvenalp and Demirezer 2005).
Compound 7 was identified as the chalcone glycoside isosalipurposide (Ghribia et al. 2014),
and is responsible for the distinctive yellow colouration of the A. cyaophylla flowers.
The polar extract from J. mimosifolia D.Don flowers was subjected to reverse-phase HPLC,
with optimal conditions using a gradient elution (100% to 60%) of solvent A (0.1% trifluo-
roacetic acid in water) over 40 min with solvent B (0.1% trifluoroacetic acid in acetonitrile).
Preparative RP-HPLC afforded the separation of nine compounds (Figure 1(B)) including five
jacarnanone-derived glucosidic esters (13, 14, 16, 17 (Gachet et al. 2010; Rana et al. 2013))
and the new jacarananone-derived glucosidic ester (10), alongside potential degradation
products 9 (Gachet et al. 2010) and 12 (Gachet et al. 2010). The known phenylpropanoid
glucoside (11) (Zaghloul et al. 2011) and apigenin 7-β-glucoside (15) (Vanhoenacker et al.
2002) were also separated.

NATURAL PRODUCT RESEARCH
5
Compounds 16 and 17 were identified as Jacaglabroside C and D, previously isolated
from J. glabra (Gachet et al. 2010); compounds 13, 14, 16, 17 were reported for the first time
from the flowers of J. mimosifolia D.Don.
Compound 10 was isolated as a yellow gum. The LRESIMS of 10 showed a peak at m/z
+
3
53 [M+Na] and analysis of the HRESIMS showed a peak at m/z 353.0839 (Calcd. for
+
1
C H O Na , 353.0849). Analysis of the H and HSQC NMR spectra indicated the presence
1
4
18
9
of an aromatic substituted sugar unit, identified as β-D-glucopyranose moiety (Table S18).
1
Analysis of the H NMR spectrum showed a large coupling constant for the anomeric
protons at δ 5.42 (J = 8.2 Hz), therefore the sugar was assigned as the β-anomeric sugar
H
configuration (Duus et al. 2000). Furthermore, a pair of resonances at δ 7.01 (d, J = 8.5 Hz,
H
2H) and 6.13 (d, J = 8.5 Hz, 2H) were assigned as H-2′/6′ and H-3′/5′, respectively, which
showed gHMBC correlations with resonances at δ 44.3, 67.4, 187.1, which were assigned
C
1
as C-7′, C-1′, and C-4′, respectively (Figure S28). In addition, H NMR spectroscopic analysis
showed a resonance at δ 2.84 (s), assigned as the methylene proton H-7′ which showed
H
two bond and three bond correlations with quaternary carbons resonances at δ 168.8 and
C
152.5 assigned to C-8′ and C-2′/C6′, respectively, allowing the identification of a jacaranone
ester moiety. Further gHMBC spectral anlysis showed a proton-carbon correlation from H1
to C-8′ establishing the position of the link between the sugar with jacaranone acid moiety
at the C1 of the sugar (Figure S28). In addition, acid hydrolysis of 10 indicated the presence
of a β-D-glucopyranose moiety via HPLC comparison to authentic standards at retention
time 8.33 min. Therefore, compound 10 was proposed as a new phenylethanoid
β-D-glucopyranose.
The Australian Indigenous people in northern New South Wales have used about 150
species of plants as antiseptic agents (Palombo and Semple 2001; Cock 2007), with Alocasia
brisbanensis, Corymbia intermedia, Crinum asiaticum, and Syncarpia glomulifera used to dis-
infect wounds (Lassak and McCarthy 2011; Packer et al. 2015). Therefore, the methanol
extracts from both species, and the isolated compounds (1 – 17), were screened for their
antibacterial activities against five bacteria and two fungi at 32 μg/mL. Their activities were
analysed based on the ability of the sample to inhibit the growth of microorganisms equal
or more than 80% with Z-score ≥2.5. All compounds were inactive against all the tested
microorganisms based on this criteria (Table S19).
Although the above compounds tested inactive (against microorganism), there are
reports of other biological activities associated with the compounds isolated in this study.
For example, naringenin and naringenin glucosides (1, 2, 8) are reported to exhibit hydroxyl
and superoxide radical scavenger efficiency and also showed effectiveness in protection
against oxidative damage to lipids in a dose-dependent manner (Patel et al. 2014).
Furthermore, chalcone (7) has reported anti-infective, anti-inflammatory and cytotoxic prop-
erties (Rozmer and Perjési 2016). Ghribia et al. reported that compound 7, isolated from A.
cyanophylla flowers, was found to be active against acetylcholinesterase with an IC value
5
0
of 52.04 μg/mL (Ghribia et al. 2014).
Furthermore, the leaves and bark of J. mimosifolia D.Don have been used in traditional
medicine in Brazil, Argentina, and Ecuador to treat sexually transmitted disease and blood
purification (Zaghloul et al. 2011). Previous studies reported compounds 14, 16, 17 as active
in vitro against P. falciparum K1 strain with IC values of 0.56, 0.56, and 0.55 μg/mL, respec-
5
0
tively (Gachet et al. 2010).

6
R. HENDRA ET AL.
3
. Conclusion
Eight secondary metabolites were identified from the A. pycnantha flower including isosali-
purposide (7) which may be responsible for their distinctive colouration. Nine secondary
metabolites were isolated from the J. mimosifolia D.Don flower including the new pheny-
lethanoid β-D-glucopyranose (10). All isolated compounds were inactive against bacteria
tested at concentration of 32 μg/mL.
Acknowledgment
Antimicrobial screening was performed by CO-ADD (The Community for Antimicrobial Drug Discovery),
funded by the Wellcome Trust (UK) and The University of Queensland (Australia).
Disclosure statement
No potential conflict of interest was reported by the authors.
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