A Photo of Viburnum species A Photo of Viburnum species.

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A Photo of Viburnum species A Photo of Viburnum species

Abstract Bioassay-guided fractionation of the methanolic extract of Viburnum awabuki afforded two new lupane triterpene derivatives; 6b -hydroxyl-3,20-dioxo-30 norlupane-28-oic acid (1) and 3,4-secolup-4,20-dihydroxy-3,28-dioic acid-3-oic acid methyl ester (2), along with seven known lupane and oleanane- type triterpenes (3–9). The structure of the isolated compoundswas assigned using different spectroscopic techniques including 1D and 2D NMR. The 13 CNMR data of compounds 5 and 9 is reported for the first time. Triterpenes 1, 2, and 7–9 showed in vitro cytotoxic activity against several tumor cell line

Results Different chromatographic techniques utilizing normal and reversed phase silica gel have been used for fractionation of the methanol extract of the leaves and twigs of V. awabuki. The result of this separation yielded two new triterpenes derivatives, norlupane (1) and secolupane (2). In addition, seven known lupan- and oleanane-type triterpenes were also identified. The known oleanane-type triterpenes were idenitified as oleanolic acid (3  - hydroxyolean-12-en-28-oic acid) (3) and sumareesinolic acid (3 ,6  -dihydroxyolean-12-en-28-oic acid) (4), while the known lupane type were identified as 3  -hydroxylup- 12-en-28-oic acid (5), 3 ,20-dihydroxy lupane-28-oic acid (6), 6  -hydroxy-3-oxolup 20(29)-en-28 oic acid (7), 6 ,30- dihydroxy-3-oxolup 20(29)-en-28-oic acid (8), and 20 hydroxy-3-oxolup-28-oic acid (9). The 13 CNMR data of compounds 5 and 9 is reported for the first time. Triterpenes 1, 2, and 7–9 showed in vitro cytotoxic activity against several tumor cell line

Extraction, Separation and Purification Scheme of viburnum awabuki leaves and twigs

Triterpenes isolated from vibrnum awabuki

1 HNMR of Compound ’

DEPT Experiment of Compound

HSQC of Compound

HMBC of Compound

1 HNMR of Compound 2 OMe OH

HSQC of Compound 2 OMe OMe

HMBC of Compound ,27 20 OMe

Expanded HMBC of Compound

NOESY of Compound 2

1 HNMR of Compound

13 C NMR of Compound

Expanded 13 C NMR of Compound x

HSQC of Compound

1 HNMR of Compound 4 12OH x

13 C NMR and DEPT Experiment of Compound 4 13 C NMR and DEPT Experiment of Compound

HSQC of Compound

1 HNMR of Compound 5 in (CDCl 3 +CD 3 OD) 3 12 x

13 C NMR of Compound

DEPT Experiment of Compound

1 HNMR of Compound 6

13 C NMR and DEPT Experiment of Compound

DEPT Experiment of Compound

1 HNMR of Compound

H HCOSY of Compound

DEPT Experiment of Compound

HSQC of Compound

1 HNMR of Compound

HSQC of Compound 8

1 HNMR of Compound 9

13 C NMR and DEPT Experiments of Compound 9

Expanded 13 C NMR of Compound

DEPT Experiments of Compound 9

HSQC of Compound 9

HMBC of Compound 9