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Hakim, E.H., Asnizar , Yurnawilis , Aimi, N., Kitajima, M., Takayama, H. (2002) Artoindonesianin P, a new prenylated flavone with cytotoxic activity from Artocarpus lanceifolius, Fitoterapia, 73, 668-673 Hakim, E.H., Achmad, S.A., Juliawaty, L.D., Makmur, L., Syah, Y.M., Aimi, N., Kitajima, M., Takayama, H., Ghisalberti, E.L. (2006), Prenylated flavonoids and related compounds of the Indonesian Artocarpus (Moraceae), Journal of Natural Medicine, 60, 161-184. Hakim, E.H., Aripin, A., Achmad, S.A., Aimi, N., Kitajima, M., Makmur, L., Mujahidin, D., Syah, Y.M., Takayama, H. (2001), Artoindonesianin E, a new flavanone derivative from Artocarpus champeden, Proc ITB (Indonesia), 33, 69–73. Hakim, E.H., Aripin, A., Fahriyati, A., Kau, M.S., Achmad, S.A., Makmur, L., Ghisalberti, E.L., Nomura, T. (1999), Artoindonesianins A and B, two new prenylated flavones from the root of Artocarpus champeden, Journal of Natural Product, 62, 613-615. Hano, Y., Aida, M., Nomura, T. (1990), Two new natural diels-alder type adducts from the root bark of Artocarpus heterophyllus, Journal of Natural Product, 53, 391-395. Hano, Y., Inami, R., Nomura, T. (1994), Constituents of Moraceae plants. 20. A novel flavone, artonin V, from the root bark of Artocarpus altilis, Journal of Chemical Research, Synopses, 9, 348-349. Heyne, K. (1987), Tumbuhan Berguna Indonesia II, Terjemahan, Penerbit Badan Litbang Kehutanan, Jakarta. Jaret, F.M. (1959), Studies in Artocarpus and allied genera, III. A revision of Artocarpus subgenus Artocarpus, Journal of Arnold Arboretum, 40, 113-155, 298-368 Jaret, F.M. (1960), Studies in Artocarpus and allied genera, IV. A revision of Artocarpus subgenus Pseudojaca, Journal of Arnold Arboretum, 41, 71-140. Jayasinghe, L., Balasooriya, B.A.I.S., Padmini,W.C., Hara, N., FujimotoY. (2004), Geranyl chalcone derivatives with antifungal and radical scavenging properties from the leaves of Artocarpus nobilis, Phytochemistry, 65, 1287-1290. Jayasinghe, L., Rupasinghe, G.K., Hara, N., Fujimoto, Y. (2006), Geranylated phenolic constituents from the fruits of Artocarpus nobilis, Phytochemistry, 67, 1353-1358. Jayasinghe, U.L.B., Samarakoon T.B., Kumarihamy, B.M.M., Hara, N., Fujimoto Y., (2008), Four new prenylated flavonoids and xanthones from the root bark of Artocarpus nobilis, Fitoterapia, 79, 37-41.

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Kijjoa, A., Cidade, H.M., Pinto, M.M.M., Gonzalez, M.J.T.G., Anantachoke, C., Gedris, T.E., Herz, W. (1996), Prenylflavonoids from Artocarpus elasticus, Phytochemistry, 43, 691-694. Kijjoa, A., Cidade, H.M., Gonzalez, M.J.T.G., Afonso, C.M., Silva, A.M.S., Herzt, W. (1998), Further prenylflavonoids from Artocarpus elasticus, Phytochemistry, 47, 875-878. Ko, H.H., Lu, Y.H., Yang, S.Z., Won, S.J., Lin, C.N. (2005), Cytotoxic prenylflavonoids from Artocarpus elasticus, Journal of Natural Product, 68, 1692-1695. Ko, H.H., Yang, S.Z., Lin, C.N. (2001), Artocarpol F, a phenolic compound with a novel skeleton, isolated from Artocarpus rigida, Tetrahedron Letters, 42, 5269-5270. Likhitwitayawuid, K., Sritularak, B. (2001), A new dimeric stilbene with tyrosinase inhibitiory activity from Artocarpus gomezianus, Journal of Natural Product, 64, 1457-1459. Likhitwitayawuid, K., Supudompol, B., Sritularak, B., Lipipun, V., Rapp, K., Schinazi, R.F. (2005), Phenolics with anti-HSV and anti-HIV activities from Artocarpus gomezianus, Mallotus pallidus and Triphasia trifolia, Pharmaceutical Biology, 43, 651-657. Lin, C.N., Lu, C.M., Huang, P.L. (1995), Flavonoids from Artocarpus heterophyllus, Phytochemistry, 39, 1447-1451. Lu, Y.H., Lin, C.N., Ko, H.H., Yang, S.Z., Tsao, L.T., Wang, J.P. (2002), Two novel and anti-inflammatory constituents of Artocarpus rigida, Helvetica Chimica Acta, 85, 1636-1632. Makmur, L., Syamsurizal, Tukiran, Achmad, S.A., Aimi, N., Hakim, E.H., Kitajima, M., Takayama, H. (2000), Artoindonesianin C, a new xanthone derivative from Artocarpus teysmanii, Journal of Natural Product, 63, 243-244. Murniana (1995), Beberapa Senyawa Metabolit Sekunder dari Kulit Batang Artocarpus reticulatus, Tesis Program Magister, Institut Teknologi Bandung. Mustapha, I., Juliawaty, L.D., Syah, Y.M., Achmad, S.A., Hakim, E.H., Latip J., Takayama H., (2007), Prenylated flavones from Artocarpus lanceifolius and their cytotoxic properties, submitted. Namdaung, U., Aroonrerk, N., Suksamrarn, S., Danwisetkanjana, K., Saenboonrueng, J., Arjchomphu, W., Suksamrarn, A. (2006), Bioactive constituents of the root bark of Artocarpus rigidus subsp. rigidus, Chemical and Pharmaceutical Bulletin, 54, 1433-1436.

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Nomura, T., Hano, Y., Aida, M. (1998), Isoprenoid substitued flavanoids from Artocarpus plants (Moraceae), Heterocycles, 47, 1179-1205. Patil, A.D., Freyer, A.J, Killmer, L., Offen, P., Taylor, P.B., Votta, B.J., Johnson, R.K. (2002), A new dimeric dihydrochalcone and a new prenylated flavone from the bud covers of Artocarpus altilis: potent inhibitors of cathepsin K, Journal of Natural Product, 65, 624-627. Puntumchai, A., Kittakoop, P., Rajviroongit, S., Vimuttipong, S., Likhitwitayawuid, K., Thebtaranonth, Y. (2004), Lakoochins A and B, new antimycobacterial stilbene derivatives from Artocarpus lakoocha, Journal of Natural Product, 67, 485-486. Samuel, B., Jones Jr. (1987), Plant Systematic, 2nd ed., McGraw Hill Book Company, New York. Shieh, W.L., Lin, C.N., (1992), A Quinonoid pyranobenzoxanthone and pyranodihydrobenzoxanthone from Artocarpus communis, Phytochemistry, 31, 364-367. Su, B.N., Cuendet, M., Hawthorne, M.E.,. Kardono, L.B.S, Riswan, S., Fong, H.H.S., Mehta, R.G., Pezzuto, J.M., Kinghorn, A.D. (2002), Constituents of the bark and twigs of Artocarpus dadah with cyclooxygenase inhibitory activity, Journal of Natural Product, 65, 163-169. Suhartati, T. (2001), Senyawa Fenol Beberapa Spesies Tumbuhan Jenis Cempedak Indonesia, Disertasi program doktor, Institut Teknologi Bandung. Suhartati, T., Achmad, S.A., Aimi, N., Hakim E.H., Kitajima, M., Takayama, H., Takeya, K. (2001), Artoindonesianin L, a new prenylated flavone with cytotoxic activity from Artocarpus rotunda, Fitoterapia, 72, 912-918. Sultanbawa, M.U.S, Surendrakumar, S. (1989), Two pyranodihydro benzoxanthones from Artocarpus nobilis, Phytochemistry, 28, 599-605. Syah, Y.M., Achmad, S.A,. Ghisalberti, E.L, Hakim, E.H., Makmur, L., Mujahidin, D. (2002), Artoindonesianins Q–T, four isoprenylated flavones from Artocarpus champeden Spreng. (Moraceae), Phytochemistry, 61, 949-953. Syah, Y.M., Achmad, S.A,. Ghisalberti, E.L, Hakim, E.H., Mujahidin, D (2004) Two new cytotoxic isoprenylated flavones, artoindonesianins U and V, from the heartwood of Artocarpus champeden, Fitoterapia, 75, 134-140. Syah, Y.M., Juliawaty, L.D., Achmad, S.A,. Hakim, E.H., Ghisalberti, E.L, (2006) Cytotoxic prenylated flavones from Artocarpus champeden, Journal Natural Medicine, 60, 308-312.

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59

60

Lampiran A. Spektrum UV, FTIR, 1H dan 13C NMR artonin E (36) Lampiran A.1 Spektrum UV artonin E (36)

Lampiran A.2 Spektrum FTIR artonin E (36) (KBr)

50075010001250150017502000250030003500400045001/cm

0

15

30

45

60

75

90

105

%T

3423

.65

3377

.36

3057

.17

2978

.09

2927

.94

2908

.65

2856

.58

1716

.65

1658

.78

1645

.28

1604

.77

1579

.70

1560

.41

1523

.76

1479

.40

1462

.04

1427

.32

1354

.03

1286

.52

1234

.44

1195

.87

1176

.58

1155

.36

1109

.07

1070

.49

962.

4891

6.19

871.

8283

1.32

790.

8176

3.81

698.

2366

5.44

609.

5158

6.36

538.

14

Widyo-1

61

Lampiran A3. Spektrum 1H NMR artonin E (36) (aseton-d6, 500 MHz)

Lampiran A.3.1 Spektrum 1H NMR artonin E (36) (aseton-d6, 500 MHz) perbesaran pada δH 5,1-7,0 ppm

Lampiran A.3.2 Spektrum 1H NMR artonin E (36) (aseton-d6, 500 MHz) perbesaran pada

δH 1,4-3,2 ppm

62

Lampiran A.4 Spektrum 13C NMR APT artonin E (36) (aseton-d6, 125 MHz)

Lampiran A.4.1 Spektrum 13C NMR APT artonin E (36) (aseton-d6, 125 MHz)

perbesaran pada δC 144-167 ppm

Lampiran A.4.2 Spektrum 13C NMR APT artonin E (36) (aseton-d6, 125 MHz)

perbesaran pada δC 16-33 ppm

63

Lampiran B. Spektrum UV, FTIR dan 1H NMR artonin V (38) Lampiran B.1 Spektrum UV artonin V (38)

Lampiran B.2 Spektrum FTIR artonin V (38) (KBr)

64

Lampiran B.3 Spektrum 1H NMR artonin V (38) (aseton-d6, 500 MHz)

Lampiran B.3.1 Spektrum 1H NMR artonin V (38) (aseton-d6, 500 MHz) perbesaran

pada δH 5,1-6,9 ppm

Lampiran B.3.2 Spektrum 1H NMR artonin V (38) (aseton-d6, 500 MHz) perbesaran

pada δH 5,1-6,9 ppm

65

Lampiran C. Spektrum UV, FTIR, dan 1H NMR sikloartobiloksanton (72) Lampiran C.1 Spektrum UV sikloartobiloksanton (72)

Lampiran C.2 Spektrum FTIR sikloartobiloksanton (72) (KBr)

50075010001250150017502000250030003500400045001/cm

0

15

30

45

60

75

90

105

%T

4461

.35

3560

.59

3194

.12

2974

.23

2929

.87

1653

.00

1606

.70

1550

.77

1475

.54

1355

.96

1269

.16

1244

.09

1153

.43

1114

.86

981.

7795

6.69

844.

8281

2.03

763.

8173

2.95

702.

0966

7.37

594.

08

403

12

Widyo 3

66

Lampiran C.3 Spektrum 1H NMR sikloartobiloksanton (72) (aseton-d6, 500 MHz)

Lampiran C.3.1 Spektrum 1H NMR sikloartobiloksanton (72) (aseton-d6, 500 MHz)

perbesaran pada δH 5,5-7,0 ppm

Lampiran C.3.2 Spektrum 1H NMR sikloartobiloksanton (72) (aseton-d6, 500 MHz)

perbesaran pada δH 1,2-3,5 ppm

67

Lampiran D. Spektrum UV, FTIR, dan 1H NMR artoindonesianin Z-5 (100) Lampiran D.1 Spektrum UV artoindonesianin Z-5 (100)

Lampiran D.2 Spektrum FTIR artoindonesianin Z-5 (100) (KBr)

50075010001250150017502000250030003500400045001/cm

20

30

40

50

60

70

80

90

100

%T

3346

.50

2974

.23

1653

.00

1602

.85

1548

.84

1479

.40

1357

.89

1319

.31

1273

.02

1230

.58

1155

.36

1112

.93 10

83.9

9 1060

.85

993.

34

833.

25

596.

00

401

19

Widyo 4

68

Lampiran D.3 Spektrum 1H NMR artoindonesianin Z-5 (100) (DMSO-d6, 500 MHz)

Lampiran D.3.1 Spektrum 1H NMR artoindonesianin Z-5 (100) (DMSO-d6, 500 MHz)

perbesaran pada δH 4,7-7,2 ppm

Lampiran D.3.2 Spektrum 1H NMR artoindonesianin Z-5 (100) (DMSO-d6, 500 MHz)

perbesaran pada δH 4,7-7,2 ppm

69

Lampiran E. Spektrum UV, FTIR, dan 1H NMR 12-hidroksiartonin E (37) Lampiran E.1 Spektrum UV 12-hidroksiartonin E (37)

Lampiran E.2 Spektrum FTIR 12-hidroksiartonin E (37) (KBr)

50075010001250150017502000250030003500400045001/cm

10

20

30

40

50

60

70

80

90

100

%T

3331

.07

2974

.23

2929

.87

1654

.92

1598

.99

1550

.77

1485

.19

1444

.68

1352

.10

1276

.88

1232

.51

1147

.65

993.

34 964.

41

837.

11

Widyo 2

70

Lampiran E.3 Spektrum 1H NMR 12-hidroksiartonin E (37) (aseton-d6, 500 MHz)

Lampiran E.3.1 Spektrum 1H NMR 12-hidroksiartonin E (37) (aseton-d6, 500 MHz)

perbesaran pada δH 5,2-7,0 ppm

Lampiran E.3.2 Spektrum 1H NMR 12-hidroksiartonin E (37) (aseton-d6, 500 MHz)

perbesaran pada δH 1,0-4,1 ppm