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New dammarane-type triterpenoids from Aglaia elliptica (C.DC.) blume

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DOI: 10.1080/14786419.2022.2114472

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New dammarane-type triterpenoids from Aglaia

elliptica (C.DC.) blume

Kindi Farabi, Desi Harneti, Darwati, Nurlelasari, Tri Mayanti, Rani Maharani,
Unang Supratman, Sofa Fajriah, Hadi Kuncoro, Mohamad Nurul Azmi &
Yoshihito Shiono

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Unang Supratman, Sofa Fajriah, Hadi Kuncoro, Mohamad Nurul Azmi & Yoshihito Shiono (2022):
New dammarane-type triterpenoids from Aglaia�elliptica (C.DC.) blume, Natural Product Research,
DOI: 10.1080/14786419.2022.2114472

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NATURAL PRODUCT RESEARCH
https://doi.org/10.1080/14786419.2022.2114472

New dammarane-type triterpenoids from Aglaia elliptica

(C.DC.) blume
Kindi Farabia,b, Desi Harnetia,c, Darwatia,c, Nurlelasaria,c, Tri Mayantia,c , Rani
Maharania,c, Unang Supratmana,b, Sofa Fajriahd, Hadi Kuncoroe, Mohamad Nurul
Azmif and Yoshihito Shionog
a
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran,
Sumedang, West Java, Indonesia; bCentral Laboratory, Universitas Padjadjaran, Sumedang, West Java,
Indonesia; cStudy Centre of Natural Product Chemistry and Synthesis, Faculty of Mathematics and
Natural Sciences, Universitas Padjadjaran, Sumedang, West Java, Indonesia; dResearch Center for
Raw Materials for Medicine and Traditional Medicine, National Research and Innovation Agency
(BRIN), Tangerang Selatan, Banten, Indonesia; eFaculty of Pharmacy, Universitas Mulawarman,
Samarinda, Kalimantan Timur, Indonesia; fSchool of Chemical Sciences, Universiti Sains Malaysia,
Minden, Penang, Malaysia; gDepartment of Food, Life, and Environmental Science, Faculty of
Agriculture, Yamagata University, Tsuruoka, Yamagata, Japan

ABSTRACT ARTICLE HISTORY

Three new dammarane-type triterpenoids, namely elliptaglin A- Received 29 March 2022
C (1–3) were isolated from the stem bark of Aglaia elliptica Accepted 15 August 2022
(C.DC.) Blume along with three known derivatives, namely
(20S)-hydroxydammar-24-en-3-on (4), cabralealactone (5), and E- KEYWORDS
25-hydroperoxydammar-23-en-20-ol-3-one (6). Subsequently, Aglaia elliptica; Meliaceae;
dammarane-type triterpe-
their chemical structures were determined using HR-ESI-MS, noids; elliptaglin A-C;
FTIR, 1D and 2D-NMR spectroscopic analysis as well as compari- cytotoxic activities
son with previous studies. The cytotoxicity activities of the iso-
lated compounds against MCF-7 breast cancer and B16-F10
melanoma cell lines were then tested using PrestoBlue reagent.
The analysis results showed that elliptaglin B (2) had the stron-
gest activity against both cell lines with IC50 values of 60.98
and 51.83 mM, respectively.

CONTACT Unang Supratman unang.supratman@unpad.ac.id

Supplemental data for this article can be accessed on https://doi.org/10.1080/14786419.2022.2114472
ß 2022 Informa UK Limited, trading as Taylor & Francis Group
2 FARABI ET AL.

1. Introduction
Aglaia genus, also known as Mahagoni has more than 150 species of which only 65
are grown in Indonesia (Harneti and Supratman 2021). It is also a native plant in
the tropical and subtropical regions of Asia, Australia, and the Pacific Islands.
Consequently, it is widely distributed in India, Indonesia, Malaysia, Thailand, and
Vietnam, while small populations are grown in the southern part of China as well
as the northern part of Australia (Pannell 1992). As the largest genus in the
Meliaceae family, Aglaia is known as an abundant source of secondary metabolites,
such as sesquiterpenoids (Milawati et al. 2019), diterpenoids (Yodsaoue et al. 2012),
triterpenoids (Harneti et al. 2014), protolimonoid (Farabi et al. 2017), limonoid (Sun
et al. 2022), steroids (Farabi et al. 2018; Hutagaol et al. 2020), lignan (Sianturi et al.
2016), alkaloids (Sianturi et al. 2015), and flavaglines (An et al. 2016). Furthermore,
several studies reported that it has diverse biological activities, such as cytotoxic
(Farabi et al. 2017), insecticidal (Chaidir et al. 2001), antiviral (Joycharat et al. 2008),
antifungal (Engelmeier et al. 2000), anti-inflammatory (Yodsaoue et al. 2012), and
molluscicidal (Zhang et al. 2012). Aglaia elliptica is a rain forest plant that is mainly
distributed in the northern part of Kalimantan Island, Indonesia. It is also used as
an Indonesian folk medicine for the treatment of wounds, fever, coughs, and skin
diseases (Cui et al. 1997; Muellner et al. 2005). Previous studies revealed that triter-
penoids and steroids have been isolated from its stem bark, and they have
cytotoxic activity against P388 murine leukemia cell lines (Hidayat et al. 2017;
Farabi et al. 2018). To complete the chemical study on the plant as well as con-
tinue the investigation of the cytotoxicity of its natural product, three new dam-
marane-type triterpenoids (1–3), along with three known derivatives (4–6) were
isolated and identified from its bark. Therefore, this study discusses the isolation
and structural elucidation of six dammarane-type triterpenoids (1–6) (Figure 1) as
well as their cytotoxic activity against MCF-7 breast cancer and B16-F10 melanoma
cell lines.
 NATURAL PRODUCT RESEARCH 3

Figure 1. Structure of compounds 1–6.

2. Result and discussion

Elliptaglin A (1) was isolated as a colorless oil with a molecular formula of C26H42O2,
which was obtained from the HR-ESI-TOFMS spectrum (m/z 387.3254 [M þ H]þ, calcd.
for 387.3263, C26H43O2þ) and the NMR data, as shown in Table S1. Furthermore, the
presence of functional groups was detected using the FTIR spectrum, such as hydroxyl,
carbonyl, and olefinic groups at 3403 cm1, 1708 cm1, and 1647 cm1, respectively.
The 13C NMR spectrum along with the HMQC experiment successfully identified 26
resonated carbons. They were classified into six methyls, eight methylenes, seven
methines including one olefinic at dC 126.8, one oxymethine at dC 76.3, and one alde-
hyde at dC 191.6 as well as five quaternary carbons including one olefinic at dC 167.8.
These functionalities accounted for two out of the total six degrees of unsaturation,
while the remaining four were caused by the tetracyclic dammarane-type triterpenoid
skeleton. The 1H NMR spectrum showed six tertiary methyls (dH 2.11, 0.96, 0.93, 0.90,
0.84, and 0.82), one aldehyde (dH 9.98, d, J ¼ 8.0 Hz), one olefinic (dH 5.86, d,
J ¼ 8.0 Hz), and one oxymethine (dH 3.38). The identical coupling constant of the ole-
finic and aldehyde protons indicated that the two functional groups are related to
each other by forming an a,b-unsaturated aldehyde. Furthermore, the comparison of
the NMR data of 1 with notoginsenoside ST8 isolated from Panax notoginseng (Gu
et al. 2015) showed some similarities, specifically in the side chain part, in terms of los-
ing four carbons to give an a,b-unsaturated aldehyde. The structure of 1 was deduced
by HMBC and 1H-1H COSY experiments, as shown in Figure S9 and S10. The correla-
tions observed between the five tertiary methyl protons and their neighboring car-
bons revealed that they have a tetracyclic dammarane-type triterpenoid core. The
relationship of the downfield methyl signal at Me-21 (dH 2.11) with C-17 (dC 51.3), C-
20 (dC 167.8), and C-22 (dC 126.8) indicated the presence of a double bond at C-20/C-
22. The occurrence of the 1H-1H COSY cross peak at H-22/H-23 also showed that the
compound is a degraded dammarane-type triterpenoid, which lost four carbons to
4 FARABI ET AL.

produce a terminal aldehyde group at C-23. Furthermore, the hydroxyl group at C-3
was established based on the correlations of H-1 (dH 1.46), Me-28 (dH 0.93), and Me-29
(dH 0.84) with C-3 at dC 76.3. The relative configuration of 1 was determined by a
NOESY experiment, as shown in Figure S11. The NOESY correlation of H-3/H-5 revealed
that the hydroxyl group present at C-3 has a b-orientation. The key cross peak
observed at Me-21/H-23 indicated that aldehyde C-23 and methyl C-21 are in the
same side, resulting the olefinic group has an E-configuration. Therefore, the structure
of 1 was established to be the new dammarane-type triterpenoid, (3b,20E)-3-hydroxy-
24,25,26,27-tetranordammar-20(22)-ene-23-enal, which was named elliptaglin A.
Elliptaglin B (2) has a molecular formula of C27H44O3, which was determined using
the HR-ESI-TOFMS (m/z 439.3160 [M þ Na]þ, calcd. 439.3188, C27H44O3Naþ) as well as
the NMR data, as shown in Table S1. The FTIR spectrum of 2 showed high similarity
with 1, which indicated that they relatively have the same functional groups. The 13C
NMR and DEPT spectra, as well as the HMQC experiment revealed that it contains 27
carbon resonances, which can be divided into six methyls, eight methylenes, eight
methines including two olefinic at dC 162.6 and 130.1, one oxymethine at dC 76.3, and
one aldehyde at dC 193.9 as well as five quaternary carbons of which one is oxygen-
ated at dC 76.4. The 1H NMR spectrum showed six tertiary methyls (dH 1.35, 0.92, 0.91,
0.87, 0.83, and 0.82), one aldehyde (dH 9.68, d, J ¼ 7.5 Hz, H-24), two olefinic (dH 6.84,
d, J ¼ 15.5 Hz, H-22 and 6.32, dd, J ¼ 7.5, 15.5 Hz, H-23), and one oxymethine (dH 3.38,
H-3). The coupling constant of aldehyde H-24 and olefinic H-23 at 7.5 Hz were identi-
cal, which indicated that they were in a neighboring position as an a,b-unsaturated
aldehyde. The coupling constant of two olefinic protons, namely H-22 and H-23 at
J ¼ 15.5 Hz were suitable for the E-configuration. The NMR data of 2 were also closely
related to that of 1. Furthermore, the difference between the two compounds was
that 1 contains 26 carbons, while 2 has 27. The HMBC correlations of five tertiary
methyls revealed that 2 has a tetracyclic dammarane-type triterpenoid skeleton. The
relationship of Me-21 (dH 1.35) with C-17 (dC 50.4), C-20 (dC 76.4), and C-22 (dC 162.6)
indicated the presence of hydroxyl group at C-20. The study of NMR spectra character-
istic of numbers of isolated 20-hydroxy dammarane-type triterpenoid by Ruan et al.
(2016) revealed that the dC of C-21 can be used for determination of absolute config-
uration at C-20. The dC of compound 2 was 27.3 (C-21), thus suitable for the 20S-con-
figuration (20 R if dC was 21.3) (Ruan et al. 2016). The occurrence of 1H-1H COSY cross
peak of H-22/H-23/H-24 suggests that a,b-unsaturated aldehyde was formed at C-24,
as shown in Figure S19. Consequently, the structure of 2 was established as a new
dammarane-type triterpenoid, (E)-3b,20S-dihydroxy-25,26,27-trinordammar-22-ene-24-
enal, which was named elliptaglin B.
Elliptaglin C (3) was obtained as a white amorphous powder, and its molecular for-
mula was assigned to be C30H50O2 based on the HR-ESI-TOFMS data (m/z 443.3883
[M þ H]þ, calcd. 443.3889 for C30H51O2þ) as well as the NMR spectral data, as shown in
Table S1. Furthermore, the results revealed that the compound requires six degrees of
unsaturation. The FTIR spectrum showed the presence of hydroxyl group at 3356 cm1
and olefinic group at 1645 cm1. The 13C NMR spectrum indicated that it contains 30
carbon resonances, which were classified using DEPT and HMQC spectra as eight
methyls, nine methylenes, seven methines including two olefinic at dC 123.6 and
 NATURAL PRODUCT RESEARCH 5

140.6, one oxymethine at dC 76.4, as well as six quaternary carbons of which two are
oxygenated at dC 75.7 and 72.1. The 1H NMR spectrum showed the presence of eight
tertiary methyls at dH 1.33, 1.31, 1.15, 0.94, 0.92, 0.85, 0.84, and 0.82. It also revealed
that the compound contains two sp2 methines at dH 5.62 and 5.39, as well as one oxy-
methine at dH 3.38. A comparison of the NMR data of 3 with aglaiabbreviatin D iso-
lated from A. abbreviata (Zhang et al. 2010) showed high similarity. Furthermore, the
main difference between the compounds was the presence of a hydroxyl group at C-3
in 3 instead of the carbonyl group. The dammarane-type triterpenoid skeleton was
confirmed in the HMBC spectrum of five tertiary methyls, as well as protons correla-
tions in 1H-1H COSY spectrum, as shown in Figure S1. The correlation of Me-21 (dH
1.15) with C-17 (dC 50.6), C-20 (dC 75.7), and C-22 (dC 36.7) as well as Me-26,27 (dH
1.31, 1.33) with C-24 (dC 140.6) and C-25 (dC 72.1) confirmed the formation of ether
bridge between C-20 and C-25. The olefinic group is located at C-23/C-24 based on
the correlation of H-22 at dH 2.21 with C-23 at dC 123.6 and the 1H-1H COSY cross
peak of H-22/H-23/H-24. The relative stereochemistry was determined unambiguously
in the NOESY spectrum, as shown in Figure S29. Therefore, these findings showed that
3 is a new dammarane-type triterpenoid, 20S,25-epoxy-dammar-23-ene-3b-ol, which
was named elliptaglin C.
The structure of the known compounds 4–6 were identified using the spectroscopy
methods as well as the comparison with previously reported data, namely (20S)-
hydroxydammar-24-en-3-one (4) (Heliawati et al. 2020), cabralealactone (5) (Retnowati
et al. 2021), and E-25-hydroperoxydammar-23-en-20-ol-3-one (6) (Lee et al. 2001),
which were isolated for the first time from Aglaia elliptica.
Compounds 1–6 were evaluated for their cytotoxic activities against MCF-7 breast
cancer cell lines and B16F10 melanoma skin cancer cell lines. They were then com-
pared to Cisplatin as a positive control, as shown in Table S2. The IC50 of 2 indicated
that it had the strongest activities against MCF-7 and B16F10 compared to the other
isolated compounds. These results suggest that the presence of a,b-unsaturated alde-
hyde, as well as a hydroxyl group in the side chain of dammarane-type triterpenoid
compounds, plays an important role in their cytotoxic activity. Another compound
that increased their activity was the hydroperoxyl group. This finding was clearly evi-
dent in compound 6, which was the second most active isolated compound.

3. Experimental
3.1. General experimental procedures
The mass spectra were measured using a Waters Xevo QTOFMS (Waters, Milford, MA,
USA), while the IR spectra were measured on a One Perkin Elmer infrared-100
(Shelton, Connecticut, USA). Furthermore, the NMR data were recorded on a JEOL
ECZ-500 spectrometer (Tokyo, Japan) at 500 MHz for 1H and 125 MHz for 13C using
TMS as an internal standard. Chromatographic separations were then carried out on a
silica gel G60 (Merck, Darmstadt, Germany) and octadecyl silane (Fuji Sylisia Chemical
LTD., ChromatorexV R C
18 DM1020 M, 100–200 mesh). The TLC plates were precoated
with silica gel GF254 (Merck, 0.25 mm) and RP-18 F254s plates (Merck), after which
detection was performed by spraying with 10% H2SO4 in ethanol, followed by heating.
6 FARABI ET AL.

3.2. Plant material

The stem bark of A. elliptica was obtained from the Bogor Botanical Garden, West
Java, Indonesia, in June 2015. The plant was then identified and classified by the staff
of Herbarium Bogoriense. Subsequently, a voucher specimen with No. Bo-1294562 was
deposited at the herbarium.

3.3. Extraction and isolation

A. elliptica stem bark was ground to dried powder of which 2.3 kg was extracted
exhaustively with methanol (12 L  5) at room temperature. Subsequently, a total of
321.5 g extract was obtained after the solvent was evaporated under reduced pressure.
It was then partitioned with n-hexane, ethyl acetate, and n-butanol to produce 22.6 g,
31.4 g, and 34.5 g of the extracts, respectively.
22.6 g of the n-hexane extract was fractionated by vacuum liquid chromatography
(r: 5 cm; h: 12 cm) on silica gel (300 g of G60 silica gel) using a gradient elution of n-
hexane-ethyl acetate (10:0–0:10, stepwise 10%; v: 500 mL) continued by ethyl acetate-
methanol (10:0–0:10, stepwise 10%; v: 500 mL) to give five fractions (A–E).
Subsequently, 6 g of C was separated with silica gel column chromatography (70-230
mesh, 120 g) using a gradient elution of n-hexane-ethyl acetate (10:0–1:1 stepwise 5%;
r: 4 cm; h: 15 cm; v: 400 mL) to give five fractions (C1–C5). A total of 2.1 g C3 was then
separated with silica gel column chromatography (70–230 mesh, 63 g) using a gradient
elution of n-hexane-ethyl acetate (10:0–7:3 stepwise 2.5%; r: 2 cm; h: 15 cm; v: 240 mL)
to give eight fractions (C3a-C3h). 516 mg of fraction C3c was separated with silica gel
column chromatography (230–400 mesh, 21 g) using n-hexane-ethyl acetate in a ratio
of 23:2 to give three fractions (C3c1–C3c3). 105 mg of fraction C3c1 was then sepa-
rated with silica gel column chromatography (230–400 mesh, 4.2 g) using n-hexane-
methylene chloride-ethyl acetate in a ratio of 7:3:4 to give four fractions
(C3c1a–C3c1d). Furthermore, 44 mg of C3c1b was separated with silica gel column
chromatography with silica gel column chromatography (230–400 mesh, 1.8 g) using
n-hexane-methylene chloride-ethyl acetate in a ratio of 7:3:1 to produce 11.3 mg of
compound 4. A total of 134 mg C3c3 was then separated with silica gel column chro-
matography with silica gel column chromatography (230–400 mesh, 5.7 g) using n-hex-
ane-ethyl acetate in a ratio of 17:3 to give six fractions (C3c3a–C3c3f). 21 mg of C3c3c
was then separated with ODS column chromatography (1.3 g of ODS silica gel) using
methanol-water in a ratio of 10:1 to produce 4 mg of 1. 270 mg of C3d was separated
with silica gel column chromatography (230–400 mesh, 11 g) using n-hexane-ethyl
acetate (18:2–17:3 stepwise 1%; r: 1 cm; h: 15 cm; v: 10 mL) to give three fractions
(C3d1-C3d3). 73 mg of C3d2 was separated with ODS column chromatography (3.7 g
of ODS silica gel) using acetonitrile-water in a ratio of 17:3 to produce 10 mg of com-
pound 5. Subsequently, a total of 232 mg C3e was separated with silica gel column
chromatography (230–400 mesh, 9.3 g) using methylene chloride-ethyl acetate in a
ratio of 9:1 to give six fractions, namely C3e1–C3e6. 23 mg of C3e3 was then separated
with ODS column chromatography (1.2 g of ODS silica gel) using methanol-water in a
ratio of 17:3 to produce 2 mg of compound 2. 50 mg C3e4 was separated with the
same technique (2.5 g of ODS silica gel) using methanol-water in a ratio of 17:3 to
 NATURAL PRODUCT RESEARCH 7

produce 4 mg of compound 6. 53 mg of C3e6 was separated with ODS column chro-

matography (2.6 g of ODS silica gel) using methanol-water in a ratio of 17:3 to give
3 mg of compound 3.

3.3.1. Elliptagline A (1)

Colourless oil; [a]25D þ15.2 (c 0.1, MeOH); IR (KBr) mmax 3484, 2946, 2853, 1708, 1647,
1443, 1377, 1069 cm1; HR-TOFMS m/z 387.3254 [M þ H]þ (calcd. for C26H43O2þ, m/z
387.3263); 1H-NMR (CDCl3, 500 MHz) and 13C-NMR (CDCl3, 125 MHz), as shown in
Table S1.

3.3.2. Elliptagline B (2)

Colourless oil; [a]25D þ17.4 (c 0.1, MeOH); IR (KBr) mmax 3448, 2927, 2867, 1683, 1455,
1376, 1068 cm1; HR-TOFMS m/z 439.3160 [M þ Na]þ (calcd. for C27H44O3Naþ, m/z
439.3188); 1H-NMR (CDCl3, 500 MHz) and 13C-NMR (CDCl3, 125 MHz), as shown in
Table S1.

3.3.3. Elliptagline C (3)

White amorphous powder; m.p. (decomposed); [a]25D þ30 (c 0.1, MeOH); IR (KBr) mmax
3356, 2975, 2852, 1645, 1455, 1375, 1068 cm1; HR-TOFMS m/z 443.3883 [M þ H]þ
(calcd. for C30H51O2þ, m/z 443.3889); 1H-NMR (CDCl3, 500 MHz) and 13C-NMR (CDCl3,
125 MHz), as shown in Table S1.

3.4. Cytotoxic bioassay

The cytotoxic bioassay was carried out using the PrestoBlue assay, which was reported
by Izdihar et al. (2021).

4. Conclusions
Three new dammarane-type triterpenoids, elliptaglin A-C (1–3) as well as three known
triterpenoids (4–6) were isolated from the stem bark of A. elliptica. Furthermore, com-
pound 2 had the strongest cytotoxic activities against MCF-7 breast cancer and
B16F10 melanoma skin cancer cell lines. The results revealed that the presence of
a,b-unsaturated aldehyde and hydroxyl group in side chain have an important role in
the cytotoxicity of dammarane-type triterpenoid compounds.

Disclosure statement
No potential conflict of interest was reported by the authors.

Funding
This study was funded by Universitas Padjadjaran under the Head Lecturer Acceleration
Research with No. 4895/UN6.3.1/PT.00/2021 by Kindi Farabi and Academic Leadership Grant
with No: 1959/UN6.3.1/PT.00/2021 by Unang Supratman.
8 FARABI ET AL.

ORCID
Tri Mayanti http://orcid.org/0000-0003-1628-6288

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