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DSpace at VNU: Three new cassane-type furanoditerpenes from the seed of Vietnamese Caesalpinia bonducella

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Constituents of Caesalpinia crista from Indonesia.. Novel norcassane-type diterpene from the seed kernels of Caesalpinia 230 crista.. New antiviral cassane 234 furanoditerpenes from Caes

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1 Three new cassane-type furanoditerpenes from the seed of vietnamese

3 Q2 Phu Hoang Danga, Mai Thanh Thi Nguyena,b, Hai Xuan Nguyena, Dung Thuy Thi Vua,

4 Son Van Truonga, Nhan Trung Nguyena,b,*

5 a Faculty of Chemistry, University of Science, Vietnam National University, Hochiminh City, Viet nam

Cancer Research Laboratory, Vietnam National University, Hochiminh City, Viet nam

A R T I C L E I N F O

Article history:

Received 6 April 2015

Received in revised form 18 May 2015

Accepted 20 May 2015

Available online xxx

Keywords:

Caesalpiniaceae

Cassane-type furanoditerpenes

A B S T R A C T Threenewcassane-typefuranoditerpenes,bonducellpinH(1),bonducellpinI(2),and 7-acetoxycae-salpininP(3),togetherwithsevenknowncompounds(4–10)havebeenisolatedfromtheMeOHextract

oftheseedkernelsofCaesalpiniabonducellafromVietnam.Thestructuresofthesecompoundswere elucidatedbyusingspectroscopictechniques

ã2015PublishedbyElsevierB.V.onbehalfofPhytochemicalSocietyofEurope

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furanodi-32

7-33

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(8)(Awaleetal.,2006),2-acetoxycaesaldekarinE(9)(Kalaunietal.,

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HR-41

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* Corresponding author at: Faculty of Chemistry, University of Science, Vietnam

National University – Hochiminh City, Viet nam Tel.: +84 907 426 332;

fax: +84 838 353 659.

E-mail address: ntnhan@hcmus.edu.vn (P.H Dang).

http://dx.doi.org/10.1016/j.phytol.2015.05.018

1874-3900/ã 2015 Published by Elsevier B.V on behalf of Phytochemical Society of Europe.

Phytochemistry Letters xxx (2015) xxx–xxx

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57 C-7.Thelocationoftheacetoxylsubstituentsweredeterminedto

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HR-77

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of 2(Table 1)showed25 carbonsignals includingfourolefinic

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Fig 1 Chemical structures of three new cassane-type furanoditerpenes.

Table 1

The NMR data of compounds 1–3 in CDCl 3 ( in ppm, multiplicities, J in Hz) a

1

C

2.75 (1H, dd, 13.0, 8.0)

1.91 (1H, m)

2.96 (1H, d, 12.0) 2.60 (1H, dd, 16.5, 10.5)

5.09 (1H, s)

5-OH 2.95 (1H, d, 1.5)

a

The 1

H and 13

C NMR spectra were measured at 500 and 125 MHz, respectively.

2 P.H Dang et al / Phytochemistry Letters xxx (2015) xxx–xxx

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89 169.6),andamethoxylcarbon(C=52.1).ThepartialstructureC(2)

H-125

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7-147

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rear-149

C-150

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spectropho-156

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Fig 3 ROESY correlations of compounds 1 and 2.

Fig 2 Key HMBC and 1

H- 1

H COSY correlations of three new compounds 1–3.

P.H Dang et al / Phytochemistry Letters xxx (2015) xxx–xxx 3

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158 aninternalstandard,andchemicalshiftsareexpressedin values.

202 (10mg)and8(8mg)

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Acknowledgements

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phytol.2015.05.018

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References

226 Awale, S., Linn, T.Z., Tezuka, Y., Kalauni, S.K., Banskota, A.H., Attamimi, F., Ueda, J.-Y.,

227 Kadota, S., 2006 Constituents of Caesalpinia crista from Indonesia Chem.

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229 Banskota, A.H., Attamimi, F., Usia, T., Linn, T.Z., Tezuka, Y., Kalauni, S.K., Kadota, S.,

2003 Novel norcassane-type diterpene from the seed kernels of Caesalpinia

230 crista Tetrahedron Lett 44, 6879–6882.

231 Bich, D.H., 2003 Vietnamese Medicinal Plants and Animals Science and Technology

232 Publisher, Hanoi.

233 Jiang, R.W., Ma, S.C., But, P.P., Mak, T.C., 2001 New antiviral cassane

234 furanoditerpenes from Caesalpinia minax J Nat Prod 64, 1266–1272.

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252 Peter, S.R., Tinto, W.F., McLean, S., Reynolds, W.F., Tay, L.L., 1997 Caesalpinin, a

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255 Peter, S.R., Tinto, W.F., McLean, S., Reynolds, W.F., Tay, L.L., Yu, M., Chan, W.R., 1998.

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257 Caesalpinia bonducella Magn Reson Chem 36, 124–127.

4 P.H Dang et al / Phytochemistry Letters xxx (2015) xxx–xxx

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