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Chemical constituents and biological activities from branches of Colubrina asiatica

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Natural Product Research
Authors:
Watchara Sangsopha at Chulabhorn Research Institute
Watchara Sangsopha
Kwanjai Kanokmedhakul at Khon Kaen University
Kwanjai Kanokmedhakul
Ratsami Lekphrom at Khon Kaen University
Ratsami Lekphrom
Somdej Kanokmedhakul at Khon Kaen University
Somdej Kanokmedhakul
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Abstract

Sixteen compounds were isolated from a Thai medicinal plant, Colubrina asiatica. The isolated compounds were elucidated on the basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene acids (1-6), five steroids (7-11), one benzoic acid derivative (12), two peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin (16). Compounds 3 and 10 showed antimalarial activity against Plasmodium falciparum. Compound 5 showed antimycobacterial activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak cytotoxicity against cancer cell lines. Compounds 1-15 have been isolated for the first time from this plant.
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Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
Chemical constituents and biological activities
from branches of Colubrina asiatica
Watchara Sangsopha, Kwanjai Kanokmedhakul, Ratsami Lekphrom &
Somdej Kanokmedhakul
To cite this article: Watchara Sangsopha, Kwanjai Kanokmedhakul, Ratsami Lekphrom & Somdej
Kanokmedhakul (2017): Chemical constituents and biological activities from branches of Colubrina
asiatica, Natural Product Research, DOI: 10.1080/14786419.2017.1320787
To link to this article: http://dx.doi.org/10.1080/14786419.2017.1320787
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NATURAL PRODUCT RESEARCH, 2017
https://doi.org/10.1080/14786419.2017.1320787
SHORT COMMUNICATION
Chemical constituents and biological activities from branches
of Colubrina asiatica
Watchara Sangsopha, Kwanjai Kanokmedhakul, Ratsami Lekphrom and
Somdej Kanokmedhakul
Natural Products Research Unit, Faculty of Science, Department of Chemistry, and Center for Innovation in
Chemistry, Khon Kaen University, Khon Kaen, Thailand
ABSTRACT
Sixteen compounds were isolated from a Thai medicinal plant,
Colubrina asiatica. The isolated compounds were elucidated on the
basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene
acids (1–6), ve steroids (7–11), one benzoic acid derivative (12), two
peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin
(16). Compounds 3 and 10 showed antimalarial activity against
Plasmodium falciparum. Compound 5 showed antimycobacterial
activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak
cytotoxicity against cancer cell lines. Compounds 1–15 have been
isolated for the rst time from this plant.
1. Introduction
Colubrina asiatica (L.) Brongn (Rhamnaceae) is a rambling shrub, 4 m in height, found widely
in South-East Asia, tropical Australia and in the Pacic Islands. In Thailand, it is known as
‘Khan song’ or ‘Kan thoeng’. The leaves and bark are used traditionally as a decoction for the
treatment of skin diseases and the roots as a cure for fever and thirst (Phonsena 2007).
Previous reports of compounds from the leaves of C. asiatica and related Colubrina species
led to the isolation of saponins (Wagner et al. 1983; Seaforth et al. 1992; Oulad-Ali et al. 1994;
Lee et al. 2000; Li et al. 1999; ElSohly et al. 1999), triterpenes (Roitman & Jurd 1978; Baxter &
Walkinshaw 1988) as well as alkaloids and phenolic compounds (Guinaudeau et al. 1976).
© 2017 Informa UK Limited, trading as Taylor & Francis Group
KEYWORDS
Colubrina asiatica; triterpene
acids; steroids; antimalarial;
antimycobacterial;
cytotoxicity
ARTICLE HISTORY
Received 6 January 2017
Accepted14 April 2017
CONTACT Ratsami Lekphrom ratsami@kku.ac.th
Supplemental data for this article can be accessed at http://dx.doi.org/10.1080/14786419.2017.1320787.
2 W. SANGSOPHA ET AL.
As part of our research on Thai medicinal plants containing potential bioactive compounds,
air-dried branches of C. asiatica were investigated. Both EtOAc and MeOH extracts showed
activity against Plasmodium falciparum, Mycobacterium tuberculosis and cytotoxicity towards
three cancer cell lines. We report herein the rst isolation, characterisation and biological
activities of 16 isolated compounds from the branches of this plant.
2. Results and discussion
Sixteen isolated compounds from branches of C. asiatica were identied by physical and
spectroscopic methods (IR, 1D and 2D NMR) as well as by comparison with the spectral data
of known compounds reported in literature. They consist of six triterpene acids: ceanothic
acid (1), granulosic acid (2) (Roitman & Jurd 1978), zizyberenalic acid (3) (Kundu et al. 1989),
colubrinic acid (4) (Baxter & Walkinshaw 1988), alphitolic acid (5) (Baxter & Walkinshaw 1988)
and betulinic acid (6) (Kundu et al. 1989); ve steroids: stigmast-5-en-7-one (7) ang6β-hydrox-
ystigmast-4-en-3-one (8) (Aguilar-Gonzalez et al. 2005), stigmast-4-ene-3,6-dione (9) (Ghosh
& Bhattacharya 2005), ergosterol peroxide (10) (Shin et al. 2001) and β-sitosterol (11) (Qiao
et al. 1999); 2-hydroxy-5-methoxybenzoic acid (12) (Al-Rawi & Jasim 1982); two phenylalanine
derivatives: (-)-auranamide (13) and D-phenylalanine, N-benzoyl-(2R)-2-(acetylamino)-3-
phenylpropyl ester (14) (Jakupovic et al. 1987); a sesquiterpenoid: isointermedeol (15) (Thappa
et al. 1979); and a jujubogenin glycoside: 3’’-O-acetylcolubrin (16) (Lee et al. 2000) (Figure 1
and supplementary material).
Zizyberenalic acid (3) and ergosterol peroxide (10) showed antimalarial activity against P.
falciparum with IC50 values of 4.18 and 3.08 μg/mL, respectively, which agree well with pre-
vious reported values (Suksamrarn et al. 2006; Phonkerd et al. 2008). Among isolated com-
pounds, only alphitolic acid (5) showed antimycobacterial activity against M. tuberculosis,
with MIC value of 50.00 μg/mL which supported the previous reported value (Suksamrarn et
al. 2006). This is the rst report for cytotoxicity of 3 against KB and NCI-H187 cell lines with
IC
50
values of 18.17 and 15.46 μg/mL, respectively. Compound 5 showed cytotoxicity against
KB, NCI-H187 and MCF-7 with IC50 of 32.09, 17.57 and 18.42 μg/mL, respectively. Betulinic
acid (6) has been reviewed with a wide range of cytotoxicity against human cancer cell lines
(Periasamy et al. 2014). However, this is the rst report for its cytotoxicity against NCI-H-187
(IC50 = 16.52 μg/mL). Betulinic acid (6) also exhibited cytotoxicity against KB cell lines
(IC50 = 18.06 μg/mL) which is comparable to the previously reported value (Jeong et al. 1999).
Moreover, cytotoxicity values of 10 against KB (IC50 = 29.48 μg/mL) and NCI-H187
(IC50 = 19.30 μg/mL) corresponded to previously reported values (Prompiboon et al. 2008
and Kornsakulkarn et al. 2016). In addition, this is the rst report for cytotoxicity of compound
14 against NCI-H-187 (IC50 = 19.51 μg/mL). Due to the general criteria, cytotoxicity of com-
pound is IC50 < 10 μg/mL. Therefore, antiplasmodial and antimycobacterial activities of iso-
lated compounds were not due to their general cytotoxicity. However, all bioactive compounds
showed weak activities comparing to their reference drugs. The result of biological activities
of isolated compounds is shown in Table S1 in supplementary material.
3. Conclusion
The extracts of C. asiatica branches were investigated and led to the isolation of 16 known
compounds, including six pentacyclic triterpene acids, ve steroids (7–11), 2-hydroxy-5-meth-
oxybenzoic acid (12), two peptides (13 and 14), intermedeol (15) and 3’’-O-acetylcolubrin
NATURAL PRODUCT RESEARCH 3
(16). Compounds 2, 3 and 7–15 are reported from the genus Colubrina for the rst time.
Moreover, compounds 2, 3, 7–9 and 12–13 are reported for the rst time in the family
Rhamnaceae. Several of isolated compounds exhibited antimalarial activity and cytotoxicity
towards KB, NCI-H187 and MCF-7 cancer cell lines.
Acknowledgements
This research was supported by the Thailand Research Fund and Khon Kaen University grant number
TRG5880005 (for R.L.), the Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Khon Kaen
University via the Natural Products Research Unit. W.S. thanks the Science Achievement Scholarship
of Thailand (SAST) for a scholarship. We are indebted to the Bioassay Research Facility of the National
Center for Genetic Engineering and Biotechnology via the Bioresources Research Network (BRN) for
bioactivity tests.
Disclosure statement
No potential conict of interest was reported by the authors.
Funding
This research was supported by the Thailand Research Fund and Khon Kaen University [grant number
TRG5880005].
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  • Sep 2019
Chromatographic separation of crude extracts from the leaves and stems of Croton poomae Esser led to the isolation of two new clerodane diterpenes crotonolide K (1) and furocrotinsulolide A acetate (2) and six known clerodane diterpenes (3–8), together with twelve known compounds (9–20). Their structures were established from spectroscopic analysis. The clerodane diterpenoids 1–8 were evaluated for inhibition of nitric oxide (NO) production in LPS-activated RAW 264.7 macrophages. Compounds 1, 2, 5, 7 and 8 showed potent inhibitory effects, with IC50 values ranging from 32.19 to 48.85 μM, which is better than both the standard drugs indomethacin (154.5 μM) and dexamethasone (56.28 μM).
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New triterpenoids from Leonurus japonicus (Lamiaceae)
Article
  • Feb 2019
  • BIOCHEM SYST ECOL
Three new triterpenoids (1, 4, and 5), together with 17 known analogues, were isolated from the ethyl acetate soluble portion of the EtOH extract of Leonurus japonicus Houtt. Their structures were determined by spectroscopic analysis. All known triterpenoids were isolated from the genus Leonurus for the first time. Among them, triterpenoids 2–3, 9–12, and 16–20 were first isolated from the family Lamiaceae. Furthermore, the cycloartane, taraxastane, ursane, lupane, euphane, and dammarane types are reported here for the first time from the genus Leonurus.
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Carbon-13 nuclear magnetic resonance spectra of substituted 2-hydroxybenzoic acids
Article
Full-text available
  • Jan 1982
13C NMR of 11 substituted 2- hydroxybenzoic acids were analyzed. The additivity of substituent effects on the hydroxybenzoic acids was evaluated
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Triterpenoids from Hippocratea excelsa. The Crystal Structure of 29-Hydroxytaraxerol
Article
Full-text available
  • Jun 2014
  • Z NATURFORSCH B
The root bark of Hippocratea excelsa afforded a new derivative of β -amyrin, which was identi-fied as its ferulate, together with components new in this species. They were identified as the rare 29-hydroxytaraxerol, 29-hydroxyglutinol, 29-hydroxyfriedelin and the sterol 6β -hydroxystigmast-4-en-3-one. The known triterpene quinone methides pristimerin and tingenone characteristics of this genus, β -sitosterol, trans-polyisoprene, squalene, β -amyrin, and the alditol galacticol characteristic of the Celastraceae were also isolated. The structures were established on the basis of spectral anal-ysis, including homo-and heteronuclear correlation NMR experiments (COSY, DEPT, HMQC and HMBC) and by comparison with data reported in the literature. The structure of 29-hydroxytaraxerol was confirmed by X-ray diffraction. The antimicrobial and antifungal activities of the compounds were studied, but no significant activity was found.
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Zizyberanalic acid, A pentacyclic triterpenoid of Zizyphus jujuba
Article
  • Dec 1989
  • PHYTOCHEMISTRY
A novel pentacyclic triterpenoid, zizyberanalic acid, has been isolated from both bark and roots of Zizyphus jujuba. The structure and stereochemistry of the compound have been unambiguously settled as 3α-hydroxy-2β-aldehydo-A(1)-norlup-20(29)-en-28-oic acid from detalied spectroscopic evidence and by its conversion to a compound of established structure and stereochemistry.
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Isolation and structure of an a-ring contracted triterpenoid from Colubrina texensis tissue culture
Article
  • Dec 1988
  • PHYTOCHEMISTRY
An A-ring contracted triterpenoid produced by suspension cultures of Colubrina texensis was shown to be 2β-formyl-3α-hydroxy-nor-A(1)-lup-20(29)-en-28-oic acid by X-ray crystallography. The methyl ester derivative was shown to be identical with methyl colubrinate, a compound previously isolated from a methylated acidic fraction from C. granulosa heartwood.
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Artanomaloide, a dimeric guaianolide and phenylalanine derivatives from Artemisia anomala
Article
  • Dec 1987
  • PHYTOCHEMISTRY
The aerial parts of Artemisia anomala afforded in addition to umbelliferone, herniarin and salvigenin the eudesmanolides, reynosin and armexifolin, the guaianolides dehydromatricarin and its desacetyl derivative, two secoguaianolides, a dimeric guaianolide and two derivatives of phenylalanine. The structures were elucidated by spectroscopic methods.
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Triterpenoid and phenolic constituents of Colubrina granulosa
Article
  • Dec 1978
  • PHYTOCHEMISTRY
Ether extracts of Colubrina granulosa heartwood yield the polyphenolic coumaranone maesopsin and 3 pentacyclic triterpene acids of the lup-20(29)-en-28-oic acid group, alphitolic, betulinic and ceanothic acids. Two new compounds, granulosic and colubrinic acids, which belong to a very small class of A ring contracted triterpenes were also isolated. The co-occurrence of maesopsin, alphitolic, betulinic and ceanothic acids suggests that C. granulosa (from Panama) may be closely related or identical to the Australian species, Alphitonia whitei, in which these relatively rare compounds also occur.
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