Betulinic acid

Betulinic acid
Names
	IUPAC name 3β-Hydroxylup-20(29)-en-28-oic acid
	Systematic IUPAC name (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-1-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
	Other names Betulic acid; Mairin
Identifiers
CAS Number	472-15-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3087 ;
ChEMBL	ChEMBL269277 ;
ChemSpider	58496 ;
ECHA InfoCard	100.006.773
EC Number	207-448-8;
IUPHAR/BPS	3945;
PubChem CID	64971;
UNII	4G6A18707N ;
	InChI InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1 Key: QGJZLNKBHJESQX-FZFNOLFKSA-N ; InChI=1/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1 Key: QGJZLNKBHJESQX-FZFNOLFKBI;
	SMILES O=C(O)[C@@]54[C@@H]([C@@H]3[C@@]([C@]1([C@@H]([C@]2(C)[C@@H](CC1)C(C)(C)[C@@H](O)CC2)CC3)C)(C)CC4)[C@H](C(=C)C)CC5;
Properties
Chemical formula	C30H48O3
Molar mass	456.711 g·mol−1
Melting point	316 to 318 °C (601 to 604 °F; 589 to 591 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Betulinic acid is a naturally occurring pentacyclic triterpenoid which has antiretroviral, antimalarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase.^[1] It is found in the bark of several species of plants, principally the white birch (Betula pubescens)^[2] from which it gets its name, but also the ber tree (Ziziphus mauritiana), selfheal (Prunella vulgaris), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas, a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum),^[3] flowering quince (Pseudocydonia sinensis, former Chaenomeles sinensis KOEHNE),^[4] rosemary,^[5] and Pulsatilla chinensis.^[6]

^ Chowdhury AR, Mandal S, Mittra B, Sharma S, Mukhopadhyay S, Majumder HK (July 2002). "Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: identification of the inhibitory step, the major functional group responsible and development of more potent derivatives". Medical Science Monitor. 8 (7): BR254–65. PMID 12118187.
^ Tan Y, Yu R, Pezzuto JM (July 2003). "Betulinic acid-induced programmed cell death in human melanoma cells involves mitogen-activated protein kinase activation". Clinical Cancer Research. 9 (7): 2866–75. PMID 12855667.
^ Zuco V, Supino R, Righetti SC, Cleris L, Marchesi E, Gambacorti-Passerini C, Formelli F (January 2002). "Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells". Cancer Letters. 175 (1): 17–25. doi:10.1016/S0304-3835(01)00718-2. PMID 11734332.
^ Gao H, Wu L, Kuroyanagi M, Harada K, Kawahara N, Nakane T, Umehara K, Hirasawa A, Nakamura Y (November 2003). "Antitumor-promoting constituents from Chaenomeles sinensis KOEHNE and their activities in JB6 mouse epidermal cells". Chemical & Pharmaceutical Bulletin. 51 (11): 1318–21. doi:10.1248/cpb.51.1318. PMID 14600382. (Chaenomeles sinensis KOEHNE is now named Pseudocydonia sinensis)
^ Abe F, Yamauchi T, Nagao T, Kinjo J, Okabe H, Higo H, Akahane H (November 2002). "Ursolic acid as a trypanocidal constituent in rosemary". Biological & Pharmaceutical Bulletin. 25 (11): 1485–7. doi:10.1248/bpb.25.1485. PMID 12419966.
^ Ji ZN, Ye WC, Liu GG, Hsiao WL (November 2002). "23-Hydroxybetulinic acid-mediated apoptosis is accompanied by decreases in bcl-2 expression and telomerase activity in HL-60 Cells". Life Sciences. 72 (1): 1–9. doi:10.1016/S0024-3205(02)02176-8. PMID 12409140.

[Chowdhury-1] Chowdhury AR, Mandal S, Mittra B, Sharma S, Mukhopadhyay S, Majumder HK (July 2002). "Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: identification of the inhibitory step, the major functional group responsible and development of more potent derivatives". Medical Science Monitor. 8 (7): BR254–65. PMID 12118187.

[Tan-2] Tan Y, Yu R, Pezzuto JM (July 2003). "Betulinic acid-induced programmed cell death in human melanoma cells involves mitogen-activated protein kinase activation". Clinical Cancer Research. 9 (7): 2866–75. PMID 12855667.

[Zuco-3] Zuco V, Supino R, Righetti SC, Cleris L, Marchesi E, Gambacorti-Passerini C, Formelli F (January 2002). "Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells". Cancer Letters. 175 (1): 17–25. doi:10.1016/S0304-3835(01)00718-2. PMID 11734332.

[Gao-4] Gao H, Wu L, Kuroyanagi M, Harada K, Kawahara N, Nakane T, Umehara K, Hirasawa A, Nakamura Y (November 2003). "Antitumor-promoting constituents from Chaenomeles sinensis KOEHNE and their activities in JB6 mouse epidermal cells". Chemical & Pharmaceutical Bulletin. 51 (11): 1318–21. doi:10.1248/cpb.51.1318. PMID 14600382. (Chaenomeles sinensis KOEHNE is now named Pseudocydonia sinensis)

[Abe-5] Abe F, Yamauchi T, Nagao T, Kinjo J, Okabe H, Higo H, Akahane H (November 2002). "Ursolic acid as a trypanocidal constituent in rosemary". Biological & Pharmaceutical Bulletin. 25 (11): 1485–7. doi:10.1248/bpb.25.1485. PMID 12419966.

[Ji-6] Ji ZN, Ye WC, Liu GG, Hsiao WL (November 2002). "23-Hydroxybetulinic acid-mediated apoptosis is accompanied by decreases in bcl-2 expression and telomerase activity in HL-60 Cells". Life Sciences. 72 (1): 1–9. doi:10.1016/S0024-3205(02)02176-8. PMID 12409140.

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Names

IUPAC name 3β-Hydroxylup-20(29)-en-28-oic acid
Systematic IUPAC name (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-1-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
Other names Betulic acid Mairin
Identifiers
CAS Number	472-15-1^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3087^N
ChEMBL	ChEMBL269277^Y
ChemSpider	58496^Y
ECHA InfoCard	100.006.773
EC Number	207-448-8
IUPHAR/BPS	3945
PubChem CID	64971
UNII	4G6A18707N^Y
InChI InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1^Y Key: QGJZLNKBHJESQX-FZFNOLFKSA-N^Y InChI=1/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1 Key: QGJZLNKBHJESQX-FZFNOLFKBI
SMILES O=C(O)[C@@]54[C@@H]([C@@H]3[C@@]([C@]1([C@@H]([C@]2(C)[C@@H](CC1)C(C)(C)[C@@H](O)CC2)CC3)C)(C)CC4)[C@H](C(=C)C)CC5
Properties
Chemical formula	C₃₀H₄₈O₃
Molar mass	456.711 g·mol⁻¹
Melting point	316 to 318 °C (601 to 604 °F; 589 to 591 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references