A set of pentacyclic triterpenes has been isolated from the bark of Maytenus macrocarpa (Celastraceae). It includes two new olean-12-ene derivatives, namely 3β, 22α-dihydroxy-olean-12-en-30-oic acid (1) and 22α-hydroxy-olean-12-en-3-oxo-30-oic acid (2), and the new urs-12-ene derivative 3-(E)-coumaroyluvaol (7), along with 10 known compounds possessing olean-12-ene, urs-12-ene, lupane and friedelane skeletons. The structures have been elucidated by extensive spectroscopic methods including 1D- and 2D-NMR experiments, as well as ESI-MS analysis. All isolated compounds were tested for anti-HIV activity in C8166 cells infected with HIV-1MN. The most active compound was 22α-hydroxy-12-en-3-oxo-29-oic acid (triterpenonic acid A, 4), with an EC50 value of 1 μg/mL and a selectivity index of 35.
PiacenteS, De TommasiN, PizzaC. (1999) Laevisines A and B: two new sesquiterpene-pyridine alkaloids from Maytenus laevis. Journal of Natural Products, 62, 161–163.
2.
MuhammadI, El SayedKA, MossaJS, Al-SaidMS, El-FeralyFS, ClarkAM, HuffordCD, OhS, MayerAMS. (2000) Bioactive 12-oleanene triterpene and secotriterpene acids from Maytenus undata. Journal of Natural Products, 63, 605–610.
3.
ChavezH, Estevez-BraunAE, RaveloAG, GonzalezAG. (1997) First examples of dammarane triterpenes isolated from Celastraceae. Tetrahedron, 53, 6465–6472.
4.
ChavezH, Estevez-BraunAE, RaveloAG, GonzalezAG. (1998) Friedelane triterpenoids from Maytenus macrocarpa. Journal of Natural Products, 61, 82–85.
5.
ChavezH, CalloN, Estevez-BraunAE, RaveloAG, GonzalezAG. (1999) Sesquiterpene polyolesters from the leaves of Maytenus macrocarpa. Journal of Natural Products, 62, 1576–1577.
6.
ChavezH, RodriguezG, Estevez-BraunAE, RaveloAG, Estevez-ReyesR, GonzalezAG, Fdez-PuenteJL, Garcia-GravalosD. (2000) Macrocarpins A-D, new cytotoxic nor-triterpenes from the leaves of Maytenus macrocarpa. Biorganic & Medicinal Chemistry Letters, 10, 759–762.
7.
Perez-VictoriaJM, TincusiBM, JimenezIA, BazzocchiIL, GuptaMP, CastanysS, GamarroF, RaveloAG. (1999) New natural sesquiterpenes as modulators of daunomycin resistance in a multidrug-resistant Leishmania tropica line. Maytenus macrocarpa. Journal of Medicinal Chemistry, 42, 4388–4393.
8.
HashimotoF, KashiwadaY, CosentinoLM, ChenCH, GarrettPE, LeeKH. (1997) Anti-AIDS agents-XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Biorganic & Medicinal Chemistry, 5, 2133–2143.
9.
SunIC, ChenCH, KashiwadaY, WuJH, WangHK, LeeKH. (2002) Anti-AIDS agents 49. Synthesis, anti-HIV, and anti-fusion activities of IC9564 analogues based on betulinic acid. Journal of Medicinal Chemistry, 45, 4271–4275.
10.
ChenK, ShiQ, KashiwadaY, ZhandDC, HuCQ, JinJQ, NozakiH, KilkuskieR, TramontanoE, ChengYC, McPhailDR, McPhailAT, LeeKH. (1992) Anti-Aids agents, 6. Salaspermic acid, an anti-HIV principle from Tripterygium wilfordii, and the structure-activity correlation with its related compounds. Journal of Natural Products, 55, 340–346.
MahatoSB, KunduAP. (1994) 13C NMR spectra of pentacyclic triterpenoids – A compilation and some salient features. Phytochemistry, 37, 1517–1575.
13.
KanedaN, PezzutoJM, KinghornAD, FarnsworthNR. (1992) Plant anticancer agents, L. Cytotoxic triterpenes from Sandoricum koetjape stems. Journal of Natural Products, 55, 654–659.
14.
NakagawaH, TakaishiY, FujimotoY, DuqueC, GarzonC, SatoM, OkamotoM, OshikawaT, AhmedSU. (2004) Chemical constituents from the Colombian medicinal plant Maytenus laevis. Journal of Natural Products, 67, 1919–1924.
15.
KutneyJP, HewittGM, LeeG, PiotrowskaK, RobertsM, RettigSJ. (1992) Studies with tissue cultures of the Chinese herbal plant Tripterygium wilfordii. Isolation of metabolites of interest in rheumatoid arthritis, immunosuppression, and male contraceptive activity. Canadian Journal of Chemistry, 70, 1455–1480.
16.
SilvaGDF, DuarteLP, VieiraFilho SA, DoriguettoAC, MascarenhasYP, EllenaJ, CastellanoEE, CotaAB. (2002) Epikatonic acid from Austroplenckia populnea: structure elucidation by 2D NMR spectroscopy and X-ray crystallography. Magnetic Resonance in Chemistry, 40, 366–370.
17.
RashidMA, GrayAI, WatermanPG. (1992) Coumarins from Phebalium tuberculosum ssp. megaphyllum and Phebalium filifolium. Journal of Natural Products, 55, 851–858.
18.
FuchinoH, SathoT, TanakaN. (1995) Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii Chemical and Pharmaceutical Bulletin, 43, 1937–1942.
19.
GaoH, WuL, KuroyanagiM, HaradaK, KawaharaN, NakaneT, UmeharaK, HirasawaA, NakamuraY. (2003) Antitumor-promoting constituents from Chaenomeles sinensis Koehne and their activities in JB6 mouse epidermal cells. Chemical and Pharmaceutical Bulletin, 51, 1318–1321.
20.
Es SaadyD, DelageC, SimonA, ChuliaAJ. (1995) Antiproliferative effects of uvaol. Fitoterapia, 66, 366–369.
