Cassane- and norcassane-type diterpenes from Caesalpinia crista of Indonesia and their antimalarial activity against the growth of Plasmodium falciparum

Thein Zaw Linn; Suresh Awale; Yasuhiro Tezuka; Arjun H. Banskota; Surya K. Kalauni; Faisal Attamimi; Jun Ya Ueda; Puji Budi Setia Asih; Din Syafruddin; Ken Tanaka; Shigetoshi Kadota

doi:10.1021/np0401720

Cassane- and norcassane-type diterpenes from Caesalpinia crista of Indonesia and their antimalarial activity against the growth of Plasmodium falciparum

Thein Zaw Linn, Suresh Awale, Yasuhiro Tezuka, Arjun H. Banskota, Surya K. Kalauni, Faisal Attamimi, Jun Ya Ueda, Puji Budi Setia Asih, Din Syafruddin, Ken Tanaka, Shigetoshi Kadota^*

^*Corresponding author for this work

Section of Natural Products & Drug Discovery, Division of Medicinal Resources, Institute of Natural Medicine

Research output: Contribution to journal › Article › peer-review

85 Scopus citations

Abstract

The CH₂Cl₂ extract of the seed kernels of Caesalpinia crista, which exhibited promising antimalarial activity against Plasmodium berghei-mfected mice in vivo, was examined and resulted in the isolation of seven new furanocassane-type diterpenes [caesalpinins C-G (1-5) and norcaesalpinins D and E (6, 7)] together with norcaesalpinins A-C (8-10) and 11 known compounds (norcaesalpinins A-C, 2-acetoxy-3-deacetoxycaesaldekarin e, caesalmin B, caesaldekarin e, caesalpin F, 14(17)-dehydrocaesalpin F, 2-acetoxycaesaldekarin e, 7-acetoxybonducellpin C, and caesalmin G). Their structures were determined on the basis of spectroscopic analysis. The isolated diterpenes showed significant dose-dependent inhibitory effects on Plasmodium falciparum FCR-3/A2 growth in vitro. Their IC₅₀ values ranged from 90 nM to 6.5 μM, and norcaesalpinin E (7) showed the most potent inhibitory activity (IC₅₀, 90 nM).

Original language	English
Pages (from-to)	706-710
Number of pages	5
Journal	Journal of Natural Products
Volume	68
Issue number	5
DOIs	https://doi.org/10.1021/np0401720
State	Published - 2005/05

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/np0401720

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Linn, T. Z., Awale, S., Tezuka, Y., Banskota, A. H., Kalauni, S. K., Attamimi, F., Ueda, J. Y., Asih, P. B. S., Syafruddin, D., Tanaka, K., & Kadota, S. (2005). Cassane- and norcassane-type diterpenes from Caesalpinia crista of Indonesia and their antimalarial activity against the growth of Plasmodium falciparum. Journal of Natural Products, 68(5), 706-710. https://doi.org/10.1021/np0401720

@article{8e7da0584bfe40dc83e64a2f1db69efd,

title = "Cassane- and norcassane-type diterpenes from Caesalpinia crista of Indonesia and their antimalarial activity against the growth of Plasmodium falciparum",

abstract = "The CH2Cl2 extract of the seed kernels of Caesalpinia crista, which exhibited promising antimalarial activity against Plasmodium berghei-mfected mice in vivo, was examined and resulted in the isolation of seven new furanocassane-type diterpenes [caesalpinins C-G (1-5) and norcaesalpinins D and E (6, 7)] together with norcaesalpinins A-C (8-10) and 11 known compounds (norcaesalpinins A-C, 2-acetoxy-3-deacetoxycaesaldekarin e, caesalmin B, caesaldekarin e, caesalpin F, 14(17)-dehydrocaesalpin F, 2-acetoxycaesaldekarin e, 7-acetoxybonducellpin C, and caesalmin G). Their structures were determined on the basis of spectroscopic analysis. The isolated diterpenes showed significant dose-dependent inhibitory effects on Plasmodium falciparum FCR-3/A2 growth in vitro. Their IC50 values ranged from 90 nM to 6.5 μM, and norcaesalpinin E (7) showed the most potent inhibitory activity (IC50, 90 nM).",

author = "Linn, {Thein Zaw} and Suresh Awale and Yasuhiro Tezuka and Banskota, {Arjun H.} and Kalauni, {Surya K.} and Faisal Attamimi and Ueda, {Jun Ya} and Asih, {Puji Budi Setia} and Din Syafruddin and Ken Tanaka and Shigetoshi Kadota",

year = "2005",

month = may,

doi = "10.1021/np0401720",

language = "英語",

volume = "68",

pages = "706--710",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "5",

}

Linn, TZ, Awale, S, Tezuka, Y, Banskota, AH, Kalauni, SK, Attamimi, F, Ueda, JY, Asih, PBS, Syafruddin, D, Tanaka, K & Kadota, S 2005, 'Cassane- and norcassane-type diterpenes from Caesalpinia crista of Indonesia and their antimalarial activity against the growth of Plasmodium falciparum', Journal of Natural Products, vol. 68, no. 5, pp. 706-710. https://doi.org/10.1021/np0401720

TY - JOUR

T1 - Cassane- and norcassane-type diterpenes from Caesalpinia crista of Indonesia and their antimalarial activity against the growth of Plasmodium falciparum

AU - Linn, Thein Zaw

AU - Awale, Suresh

AU - Tezuka, Yasuhiro

AU - Banskota, Arjun H.

AU - Kalauni, Surya K.

AU - Attamimi, Faisal

AU - Ueda, Jun Ya

AU - Asih, Puji Budi Setia

AU - Syafruddin, Din

AU - Tanaka, Ken

AU - Kadota, Shigetoshi

PY - 2005/5

Y1 - 2005/5

N2 - The CH2Cl2 extract of the seed kernels of Caesalpinia crista, which exhibited promising antimalarial activity against Plasmodium berghei-mfected mice in vivo, was examined and resulted in the isolation of seven new furanocassane-type diterpenes [caesalpinins C-G (1-5) and norcaesalpinins D and E (6, 7)] together with norcaesalpinins A-C (8-10) and 11 known compounds (norcaesalpinins A-C, 2-acetoxy-3-deacetoxycaesaldekarin e, caesalmin B, caesaldekarin e, caesalpin F, 14(17)-dehydrocaesalpin F, 2-acetoxycaesaldekarin e, 7-acetoxybonducellpin C, and caesalmin G). Their structures were determined on the basis of spectroscopic analysis. The isolated diterpenes showed significant dose-dependent inhibitory effects on Plasmodium falciparum FCR-3/A2 growth in vitro. Their IC50 values ranged from 90 nM to 6.5 μM, and norcaesalpinin E (7) showed the most potent inhibitory activity (IC50, 90 nM).

AB - The CH2Cl2 extract of the seed kernels of Caesalpinia crista, which exhibited promising antimalarial activity against Plasmodium berghei-mfected mice in vivo, was examined and resulted in the isolation of seven new furanocassane-type diterpenes [caesalpinins C-G (1-5) and norcaesalpinins D and E (6, 7)] together with norcaesalpinins A-C (8-10) and 11 known compounds (norcaesalpinins A-C, 2-acetoxy-3-deacetoxycaesaldekarin e, caesalmin B, caesaldekarin e, caesalpin F, 14(17)-dehydrocaesalpin F, 2-acetoxycaesaldekarin e, 7-acetoxybonducellpin C, and caesalmin G). Their structures were determined on the basis of spectroscopic analysis. The isolated diterpenes showed significant dose-dependent inhibitory effects on Plasmodium falciparum FCR-3/A2 growth in vitro. Their IC50 values ranged from 90 nM to 6.5 μM, and norcaesalpinin E (7) showed the most potent inhibitory activity (IC50, 90 nM).

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U2 - 10.1021/np0401720

DO - 10.1021/np0401720

M3 - 学術論文

C2 - 15921414

AN - SCOPUS:20444498304

SN - 0163-3864

VL - 68

SP - 706

EP - 710

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 5

ER -

Cassane- and norcassane-type diterpenes from Caesalpinia crista of Indonesia and their antimalarial activity against the growth of Plasmodium falciparum

Abstract

ASJC Scopus subject areas

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