Ent-16Α,17-Dihydroxy-19-Kauranoic Acid

Identification of ent-16 beta, 17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa.[Pubmed: 8786370 ]

J Nat Prod. 1996 Jun;59(6):635-7.

METHODS AND RESULTS:
Phytochemical analysis of the fruits of Annona squamosa yielded 12 known kaurane derivatives (1-11, 13) and two new kaurane diterpenoids, which have been named annosquamosin A (16 beta-hydroxy-17-acetoxy-ent-kauran-19-al) (12) and annosquamosin B (19-nor-ent-kaurane-4 alpha,16 beta,-17-triol) (14). The structures of the new compounds were established by spectral analyses and chemical evidence.
CONCLUSIONS:
Among these 14 compounds, 16 beta, 17-dihydroxy-ent-kauran-19-oic acid (16beta,17-Dihydroxy-ent-kaurane-19-oic acid, 2) showed significant activity against HIV replication in H9 lymphocyte cells with an EC50 value of 0.8 microgram/mL (therapeutic index > 5).

Diterpenes from Helianthus annuus and their cytotoxicity in vitro.[Pubmed: 17518044]

Yao Xue Xue Bao. 2007 Feb;42(2):166-70.

METHODS AND RESULTS:
To search for bioactive compounds from the flower disc of Helianthus annuus L., chromatography was used to isolate and purify the chemical constituents, their structures were identified by spectral analysis, MTT method was applied to investigate their cytotoxic activities, some compounds showed moderate cytotoxic activities on SF-268, MCF-7 and HepG2 cell lines. Eleven compounds were obtained from the flower disc of H. annuus, and identified as ent-kaurane-2alpha, 16alpha-diol (1) and entkaurane-15alpha,16alpha-epoxy-17-al-19-oic acid (2), and nine known diterpenes, ent-kaurane-16P-ol (3), phyllocladan-16beta-ol (4) , ent-atisan-16a-ol (5) , grandifloric acid (6) , angeloylgrandifloric acid (7), ent-kaurane-16-en-19-oic acid (8), ent-kaurane-17-hydroxy-15-en-19-oic acid (9), ent-kaurane-16beta, 17-dihydroxy-19-oic acid (16beta,17-Dihydroxy-ent-kaurane-19-oic acid,10), and ciliaric acid (11).
CONCLUSIONS:
Compounds 1 and 2 are new compounds, some compounds showed cytotoxic activities on SF-268, MCF-7 and HepG2 cell lines.

Effects of ent-16#beta#, 17-dihydroxy-kauran-19-oic acid on decompression and blood viscosity[Reference: WebLink]

Baiqiuen Yike Daxue Xuebao,Jan 2001, 27(5):472-474.

METHODS AND RESULTS:
ABP, LVSP, ±dp/dt_(max), HR, DBP and blood viscosity of rabbits were depressed after duodenum administration compared with before drug. ent-16#beta#, 17-dihydroxy-kauran-19-oic acid(16beta,17-Dihydroxy-ent-kaurane-19-oic acid)possesses the activities of decompression and blood viscosity depression.