From the methanol extract of Dracaena cambodiana roots two unusual 22S-spirostane steroids (1β,3β,14α,20R,22S,25R)-spirost-5-ene-1,3, 14-triol (1) and (1β,3β,14α,15α,20R,22S,25R)-spirost-5-ene-tetrol (2) have been isolated, together with a known 22R-spirostane compound, namogenin B (3). Their structures were elucidated by spectroscopic and spectrometric methods, including HRMS and extensive 1D and 2D NMR spectroscopy. Compound 1 showed significant antimicrobial activity against Pseudomonas aeruginosa, Staphylococcus aureus and Fusarium oxysporum, with MIC values of 45.0, 25.0 and 50.0 μg/mL, respectively.
LiuJ, MeiWL, WuJ, ZhaoYX, PengM, DaiHF. (2009) A new cytotoxic homoisoflavonoid from Dracaena cambodiana. Journal of Asian Natural Products Research, 11, 192–195.
8.
TranQL, TezukaY, BanskotaAH, TranQK, SaikiI, KadotaS. (2001) New spirostanol steroids and steroidal saponins from roots and rhizomes of Dracaena angustifolia and their antiproliferative activity. Journal of Natural Products, 64, 1127–1132.
9.
ChakravartyAK, PakrashiSC, UzawaJ. (1981) Studies on Indian medicinal plants. Part 6:13C nuclear magnetic resonance spectra of 23-hydroxy spirostane sapogenins of Solanum hispidum. Canadian Journal of Chemistry, 59, 1328–1330.
10.
MimakiY, NakamuraO, SashidaY, KoikeK, NikaidoT, OhmotoT, NishinoA, SatomiY, NishinoH. (1995) Structures of steroidal saponins from the tubers of Brodiaea californica and their inhibitory activity on tumor promoter-induced phospholipid metabolism. Chemical & Pharmaceutical Bulletin, 43, 971–976.
11.
IidaY, YanaiY, OnoM, IkedaT, NoharaT. (2005) Three unusual 22-β-O-23-hydroxy-(5α)-spirostanol glycosides from the fruits of Solanum torvum. Chemical & Pharmaceutical Bulletin, 53, 1122–1125.
12.
PhanVK, NguyenTHV, PhamKT, ChauVM, LeMH. (2007) New derivative of E-cinnamic acid from Gleditschia australis Hemsl. Vietnamese Pharmaceutical Journal, 47, 33–36.
13.
ZhengQA, LiHZ, ZhangYJ, YangCR. (2006) Dracaenogenins A and B, new spirostanols from the red resin of Dracaena cochinchinensis. Steroids, 71, 160–164.
14.
TobariA, TeshimaM, KoyanagiJ, KawaseM, MiyamaeH, YozaK, TakasakiA, NagamuraY, SaitoS. (2000) spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides. European Journal of Medicinal Chemistry, 35, 511–517.
15.
AgrawalPK, JainDC, GuptaRK, ThakurRS. (1985) Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins. Phytochemistry, 24, 2479–2496