Anti-HIV activity of natural triterpenoids and hemisynthetic derivatives 2004-2009

Phytochemistry Reviews

Volumn 10, Issue 4, 2011, Pages 545-564

  Cassels, Bruce K ^a   Asencio, Marcelo ^a,b  

^a UNIVERSITY OF CHILE   (Chile)

^b UNIVERSIDAD TECNOLÓGICA METROPOLITANA   (Chile)

Author keywords

AIDS; Antiviral activity; Natural products; Structural modification; Triterpenes

Indexed keywords

3BETA HYDROXYNORLUPA(1) 20(29) EN 2BETA,28 DIOIC ACID; ACUTISSIMATRITERPENE D; ACUTISSIMATRITERPENE E; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BETULIC ACID; BETULINIC ACID DERIVATIVE; BEVIRIMAT; CUCURBITANE; DAMMARANE; GLYCYRRHIZIC ACID; HEMSLECIN A; HEMSLECIN B; HOPANE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE INHIBITOR; KUGUACIN; LANCIFODILACTONE; LANOSTANE; LONGIPEDLACTONE; MASLINIC ACID; MORONIC ACID; MPC 4326; NORTRITERPENOID MICRANDILACTONE; OLEANOLIC ACID DERIVATIVE; OLEANOLIC ACID DERIVATIVE AZIDOTHYMIDINE CONJUGATE; PAPYRIOGENIN A; SERRATANE; SPHENALACTONE; TRITERPENOID; UNCLASSIFIED DRUG; UNINDEXED DRUG; URSANE; URSOLIC ACID;

ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; IC 50; MEDICINAL PLANT; MOMORDICA CHARANTIA; NONHUMAN; PRIORITY JOURNAL; SCHISANDRA; STAUNTONIA OBOVATIFOLIOLA; STRUCTURE ACTIVITY RELATION; VIRUS INHIBITION; VIRUS REPLICATION;

EID: 84855870917     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-010-9172-2     Document Type: Article

References (71)

1. Aiken C, Chen C-H (2005) Betulinic acid derivatives as HIV-1 antivirals. Trends Mol Med 11:31-36 (Pubitemid 40092672)
2. Asres K, Seyoum A, Veeresham C, Bucar F, Gibbons S (2005) Naturally derived anti-HIV agents. Phytother Res 19:557-581 (Pubitemid 41375238)
3. Baglin I, Mitaine-Offer A-C, Nour M, Tan K, Cavé C, Lacaille-Dubois M-A (2003) A review of natural and modified betulinic, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents. Mini Rev Med Chem 3:525-539
4. Chen K, Shi Q, Kashiwada Y, Zhang D-C, Hu C-Q, Jin J-Q, Nozaki H, Kilkuskie RE, Tramontano E, Cheng Y-C, McPhail DR, McPhail AT, Lee K-H (1992) Anti-AIDS agents. 6. Salaspermic acid, an anti-HIV principle from Tripterygium wilfordii, and the structure-activity correlation with its related compounds. J Nat Prod 55:340-346
5. Chen D-F, Zhang S-X, Wang H-K, Zhang S-Y, Sun Q-Z, Cosentino LM, Lee K-H (1999) Novel anti-HIV lancilactone C and related triterpenes from Kadsura lancilimba. J Nat Prod 62:94-97 (Pubitemid 29071384)
6. Chen J-C, Zhang G-H, Zhang Z-Q, Qiu M-H, Zheng Y-T, Yang L-M, Yu K-B (2008a) Octanorcucurbitane and cucurbitane triterpenoids from the tubers of Hemsleya endecaphylla with HIV-1 inhibitory activity. J Nat Prod 71:153-155 (Pubitemid 351236417)
7. Chen J-C, Tian R, Qiu M-H, Lu L, Zheng Y-T, Zhang Z-Q (2008b) Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia. Phytochemistry 69:1043-1048 (Pubitemid 351222605)
8. Chen J-C, Liu W-Q, Lu L, Qiu M-H, Zheng Y-T, Yang L-M, Zhang X-M, Zhou L, Li Z-R (2009) Kuguacins F-S, cucurbitane triterpenoids from Momordica charantia. Phytochemistry 70:133-140
9. Cos P, Maes L, Vlietinck A, Pieters L (2008) Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection - an update (1998-2007). Planta Med 74:1323-1337
10. El Dine RS, El Halawany AM, Ma C-M, Hattori M (2008) Anti-HIV-1 protease activity of lanostane triterpenes from the vietnamese mushroom Ganoderma colossum. J Nat Prod 71:1022-1026 (Pubitemid 352008899)
11. Fujioka T, Kashiwada Y, Kilkuskie RE, Cosentino LM, Ballas LM, Jiang JB, Janzen WP, Chen IS, Lee K-H (1994) Anti-AIDS agents. 11. Betulinic acid and platanic acid as anti-HIV principles from Syzygium claviflorum and the anti-HIV activity of structurally related triterpenoids. J Nat Prod 57:243-247
12. Hashimoto F, Kashiwada Y, Cosentino LM, Chen C-H, Garrett PE, Lee K-H (1997) Anti-AIDS agents-XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg Med Chem 5:2133-2143 (Pubitemid 28012601)
13. Ho J-C, Chen C-M, Row L-C (2007) Oleanane-type triterpenes from the flowers, pith, leaves, and fruit of Tetrapanax papyriferus. Phytochemistry 68:631-635
14. Huang L, Yu D, Ho P, Lee K-H, Chen C-H (2007a) Synthesis and anti-HIV activity of bi-functional triterpene derivatives. Lett Drug Des Discov 4:471-478 (Pubitemid 47607736)
15. Huang S-X, Li R-T, Liu J-P, Lu Y, Chang Y, Lei C, Xiao W-L, Yang L-B, Zheng Q-T, Sun H-D (2007b) Isolation and characterization of biogenetically related highly oxygenated nortriterpenoids from Schisandra chinensis. Org Lett 9:2079-2082
16. Huang S-X, Yang J, Huang H, Li L-M, Xiao W-L, Li R-T, Sun H-D (2007c) Structural characterization of schintrilactone, a new class of nortriterpenoids from Schisandra chinensis. Org Lett 9:4175-4178
17. Ito M, Nakashima H, Baba M, Pauwels R, De Clercq E, Shigeta S, Yamamoto N (1987) Inhibitory effect of glycyrrhizin on the in vitro infectivity and cytopathic activity of the human immunodeficiency virus [HIV (HTLV-III/LAV)]. Antiviral Res 7:127-137 (Pubitemid 17055228)
18. Ito J, Chang FR, Wang HK, Park YK, Ikegaki M, Kilgore N, Lee KH (2001) Anti-AIDS agents. 48. (1) Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis. J Nat Prod 64:1279-1281
19. Kleinwächter P, Anh N, Kiet TT, Schlegel B, Dahse HM, Härtl A, Gräfe U (2001) Colossolactones, new triterpene metabolites from a Vietnamese mushroom Ganoderma colossum. J Nat Prod 64:236-239 (Pubitemid 32198356)
20. Kondratenko RM, Baltina LA, Mustafina SR, Visil'eva EV, Pompei R, Deidda D, Plyasunova OA, Pokrovskii AG, Tolstikov GA (2004) The synthesis and antiviral activity of glycyrrhizic acid conjugates with alpha-D-glucosamine and some glycosylamines. Bioorg Khim 30:308-315
21. Kondratenko RM, Baltina LA, Baltina LA Jr, Plyasunova OA, Pokrovskii AG, Tolstikov GA (2009) Synthesis of new hetero- and carbocyclic aromatic amides of glycyrrhizic acid as potential anti-HIV agents. Pharmac Chem J 43:383-388
22. Kuo R-Y, Qian K, Morris-Natschke SL, Lee K-H (2009) Plant-derived triterpenoids and analogues as antitumor and anti-HIV agents. Nat Prod Rep 26:1321-1344
23. Lee J-S, Miyashiro H, Nakamura N, Hattori M (2008) Two new triterpenes from the rhizome of Dryopteris crassirhizoma, and inhibitory activities of its constituents on human immunodeficiency virus-1 protease. Chem Pharm Bull (Tokyo) 56:711-714 (Pubitemid 351669443)
24. Lee SY, Eom SH, Kim YK, Park NI, Park SU (2009) Cucurbitane-type triterpenoids in Momordica charantia Linn. J Med Plants Res 3:1264-1269
25. Li R-T, Li S-H, Zhao Q-S, Lin Z-W, Sun H-D, Lu Y, Wang C, Zheng Q-T (2003a) Lancifodilactone A, a novel bisnortriterpenoid from Schisandra lancifolia. Tetrahedron Lett 44:3531-3534 (Pubitemid 36398327)
26. Li R-T, Zhao Q-S, Li S-H, Han Q-B, Sun H-D, Lu Y, Zhang L-L, Zheng Q-T (2003b) Micrandilactone A: a novel triterpene from Schisandra micrantha. Org Lett 5:1023-1026 (Pubitemid 37141026)
27. Li R-T, Xiang W, Li S-H, Lin Z-W, Sun H-D (2004a) Lancifodilactones B-E, new nortriterpenes from Schisandra lancifolia. J Nat Prod 67:94-97 (Pubitemid 38141321)
28. Li R-T, Shen Y, Xiang W, Sun H-D (2004b) Four novel nortriterpenoids isolated from Schisandra henryi var. yunnanensis. Eur J Org Chem 2004:807-811
29. Li R-T, Han Q-B, Zheng Y-T, Wang R-R, Yang L-M, Lu Y, Sang S-Q, Zheng Q-T, Zhao Q-S, Sun H-D (2005) Structure and anti-HIV activity of micrandilactones B and C, new nortriterpenoids possessing a unique skeleton from Schisandra micrantha. Chem Commun (Camb) 2005: 2936-2938 (Pubitemid 40917042)
30. Li W-H, Zhang X-M, Tian R-R, Zheng Y-T, Zhao W-M, Qiu M-H (2007) A new anti-HIV lupane acid from Gleditsia sinensis Lam. J Asian Nat Prod Res 9:551-555 (Pubitemid 47450733)
31. Liu J-S, Huang M-F, Arnold GF, Arnold E, Clardy J, Ayer WA (1983) Schisanlactone A, a new type of triterpenoid from a Schisandra sp. Tetrahedron Lett 24:2351-2354
32. Ma C-M, Nakamura N, Hattori M, Kawahata T, Otake T (2002) Inhibitory effects of triterpene-azidothymidine conjugates on proliferation of human immunodeficiency virus type 1 protease. Chem Pharm Bull 50:877-880 (Pubitemid 41694918)
33. Nakashima H, Okubo K, Honda Y, Tamura T, Matsuda S, Yamamoto N (1989) Inhibitory effect of glycosides like saponin from soybean on the infectivity of HIV in vitro. AIDS 3:655-658 (Pubitemid 20006385)
34. Nie R-L, Chen Z-L (1986) The research history and present status on the chemical components of the genus Hemsleya (Cucurbitaceae). Acta Bot Yunnan 8:115-124
35. Park J-C, Kim S-C, Choi M-R, Song S-H, Yoo E-J, Kim S-H, Miyashiro H, Hattori M (2005) Anti-HIV protease activity from rosa family plant extracts and rosamultin from Rosa rugosa. J Med Food 8:107-109 (Pubitemid 40617047)
36. Parra A, Rivas F, López PE, García-Granados A, Martínez A, Albericio F, Márquez N, Muñoz E (2009) Solution and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides. Bioorg Med Chem 17:1139-1145
37. Pu J-X, Li R-T, Xiao W-L, Gong N-B, Huang S-X, Lu Y, Zheng Q-T, Lou L-G, Sun H-D (2006) Longipedlactones A-I, nine novel triterpene dilactones possessing a unique skeleton from Kadsura longipedunculata. Tetrahedron 62:6073-6081 (Pubitemid 43728071)
38. Pu J-X, Yang L-M, Xiao W-L, Li R-T, Lei C, Gao X-M, Huang S-X, Li S-H, Zheng Y-T, Huang H, Sun H-D (2008) Compounds from Kadsura heteroclita and related anti-HIV activity. Phytochemistry 69:1266-1272
39. Qian K, Yu D, Chen CH, Huang L, Morris-Natschke SL, Nitz TJ, Salzwedel K, Reddick M, Allaway GP, Lee KH (2009) Anti-AIDS agents. 78. Design, synthesis, metabolic stability assessment, and antiviral evaluation of novel betulinic acid derivatives as potent anti-human immunodeficiency virus (HIV) agents. J Med Chem 52: 3248-3258
40. Reutrakul V, Chanakul W, Pohmakotr M, Jaipetch T, Yoosook C, Kasisit J, Napaswat C, Santisuk T, Prabpai S, Konsaeree P, Tuchinda P (2006) Anti-HIV-1 constituents from leaves and twigs of Cratoxylum arborescens. Planta Med 72:1433-1435 (Pubitemid 46102403)
41. Sato N, Zhang Q, Ma C-M, Hattori M (2009) Anti-human immunodeficiency virus-1 protease activity of new lanostane-type triterpenoids from Ganoderma sinense. Chem Pharm Bull 57:1076-1080
42. Sun H-D, Qiu S-X, Lin L-Z, Wang Z-Y, Lin Z-W, Pengsuparp T, Pezzuto JM, Fong HHS, Cordell GA, Farnsworth NR (1996) Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase. J Nat Prod 59:525-527 (Pubitemid 26163365)
43. Sun I-C, Kashiwada Y, Morris-Natschke SL, Lee K-H (2003) Plant-derived terpenoids and analogues as anti-HIV agents. Curr Top Med Chem 3:155-169
44. Sun H, Fang W-S, Wang W-Z, Hu C (2006a) Structure-activity relationships of oleanane- and ursane-type triterpenoids. Bot Stud 47:339-368 (Pubitemid 44829318)
45. Sun Q-Z, Chen D-F, Ding P-L, Ma C-M, Kakuda H, Nakamura N, Hattori M (2006b) Three new lignans, longipedunins A-C, from Kadsura longipedunculata and their inhibitory activity against HIV-1 protease. Chem Pharm Bull 54:129-132 (Pubitemid 43036767)
46. Tanaka R, Kinouchi Y, Tokuda H, Nishino H, Matsunaga S (2000) Bioactive terpenoids from the stem bark of Picea glehni. Planta Med 66:630-634
47. Tanaka R, Tsujii H, Yamada T, Kajimoto T, Amano F, Hasegawa J, Hamashima Y, Node M, Katoh K, Takebe Y (2009) Novel 3α-methoxyserrat-14-en-21β- ol (PJ-1) and 3β-methoxyserrat-14-en-21β-ol (PJ-2)-curcumin, kojic acid, quercetin, and baicalein conjugates as HIV agents. Bioorg Med Chem 17:5238-5246
48. Tian R-R, Chen J-C, Zhang G-H, Qiu M-H, Wang Y-H, Du L, Shen X, Liu N-F, Zheng Y-T (2008) Anti-HIV-1 activities of hemslecins A and B. Chin J Nat Med 6:214-218 (Pubitemid 351802860)
49. Tuchinda P, Kornsakulkarn J, Pohmakotr M, Kongsaeree P, Prabpai S, Yoosook C, Kasisit J, Napaswad C, Sophasan S, Reutrakul V (2008) Dichapetalin-type triterpenoids and lignans from the aerial parts of Phyllanthus acutissima. J Nat Prod 71:655-663 (Pubitemid 351656201)
50. Wei Y, Ma C-M, Chen D-Y, Hattori M (2008) Anti-HIV-1 protease triterpenoids from Stauntonia obovatifoliola Hayata subsp. intermedia. Phytochemistry 69:1875-1879
51. Wei Y, Ma C-M, Hattori M (2009a) Anti-HIV protease triterpenoids from the acid hydrolysate of Panax ginseng. Phytochem Lett 2:63-66
52. Wei Y, Ma C-M, Hattori M (2009b) Synthesis of dammarane-type triterpene derivatives and their ability to inhibit HIV and HCV proteases. Bioorg Med Chem 17:3003-3010
53. Wei Y, Ma C-M, Hattori M (2009c) Synthesis and evaluation of A-seco type triterpenoids for anti-HIV protease activity. Eur J Med Chem 44:4112-4120
54. World Health Organization (2009) http://www.who.int/hiv/data/en/
55. Xiao W-L, Li R-T, Li S-H, Li X-L, Sun H-D, Zheng Y-T, Wang R-R, Lu Y, Wang C, Zheng Q-T (2005a) Lancifodilactone F: a novel nortriterpenoid possessing a unique skeleton from Schisandra lancifolia and its anti-HIV activity. Org Lett 7:1263-1266 (Pubitemid 40544096)
56. (Erratum in: Org Lett 8: 801)
57. Xiao W-L, Zhu H-J, Shen Y-H, Li R-T, Li S-H, Sun H-D, Zheng Y-T, Wang R-R, Lu Y, Wang C, Zheng Q-T (2005b) Lancifodilactone G: a unique nortriterpenoid isolated from Schisandra lancifolia and its anti-HIV activity. Org Lett 7:2145-2148 (Pubitemid 40826070)
58. (Erratum in: Org Lett 8:801)
59. Xiao W-L, Yang L-M, Gong N-B, Wu L, Wang R-R, Pu J-X, Li X-L, Huang S-X, Zheng Y-T, Li R-T, Lu Y, Zheng Q-T, Sun H-D (2006a) Rubriflordilactones A and B, two novel bisnortriterpenoids from Schisandra rubriflora and their biological activities. Org Lett 8:991-994 (Pubitemid 43412015)
60. Xiao W-L, Pu J-X, Chang Y, Li X-L, Huang S-X, Yang L-M, Li L-M, Lu Y, Zheng Y-T, Li R-T, Zheng Q-T, Sun H-D (2006b) Sphenadilactones A and B, two novel nortrit-erpenoids from Schisandra sphenanthera. Org Lett 8:1475-1478 (Pubitemid 43587467)
61. (Erratum in: Org Lett 8:4669)
62. Xiao W-L, Tian R-R, Pu J-X, Li X, Wu L, Lu Y, Li S-H, Li R-T, Zheng Y-T, Zheng Q-T, Sun H-D (2006c) Triterpenoids from Schisandra lancifolia with anti-HIV-1 activity. J Nat Prod 69:277-279
63. Xiao W-L, Huang S-X, Zhang L, Tian R-R, Wu L, Li X-L, Pu J-X, Zheng Y-T, Lu Y, Li R-T, Zheng Q-T, Sun H-D (2006d) Nortriterpenoids from Schisandra lancifolia. J Nat Prod 69:650-653 (Pubitemid 43798120)
64. Xiao W-L, Li X-L, Wang R-R, Yang L-M, Li L-M, Huang S-X, Pu J-X, Zheng Y-T, Li R-T, Sun H-D (2007a) Triterpenoids from Schisandra rubriflora. J Nat Prod 70:1056-1059 (Pubitemid 47056129)
65. Xiao W-L, Yang L-M, Li L-M, Pu J-X, Huang S-X, Weng Z-Y, Lei C, Liu J-P, Wang R-R, Zheng Y-T, Li R-T, Sun H-D (2007b) Sphenalactones A-D, a new class of highly oxygenated trinortriterpenoids from Schisandra sphenanthera. Tetrahedron Lett 48:5543-5546 (Pubitemid 47016584)
66. Xiao W-L, Huang S-X, Wang R-R, Zhong J-L, Gao X-M, He F, Pu J-X, Lu Y, Zheng Y-T, Zheng Q-T, Sun H-D (2008) Nortriterpenoids and lignans from Schisandra sphenanthera. Phytochemistry 69:2862-2866
67. Xu H-X, Zeng F-Q, Wan M, Sim K-Y (1996) Anti-HIV triterpene acids from Geum japonicum. J Nat Prod 59:643-645 (Pubitemid 26264625)
68. Yamaguchi C, Wanibuchi H, Kakehashi A, Tanaka R, Fukushima S (2008) Chemopreventive effects of a serratane-type triterpenoid, 3α- methoxyserrat-14-en-21β-ol (PJ-1), against rat lung carcinogenesis. Food Chem Toxicol 46:1882-1888
69. Yu D, Sakurai Y, Chen C-H, Chang F-R, Huang L, Kashiwada Y, Lee K-H (2006) Anti-AIDS agents. 69. Moronic acid and other triterpene derivatives as novel potent anti-HIV agents. J Med Chem 49:5462-5469 (Pubitemid 44373178)
70. Yu D, Morris-Natschke SL, Lee K-H (2007a) New developments in natural products-based anti-AIDS research. Med Res Rev 27:108-132 (Pubitemid 44975188)
71. Yu Y-B, Miyashiro H, Nakamura N, Hattori M, Park J-C (2007b) Effects of triterpenoids and flavonoids isolated from Alnus firma on HIV-1 viral enzymes. Arch Pharm Res 30:820-826