structural tables; triterpenoids

Cactus triterpenoids & sterols;  a tabular key to their structural formulas

Some of the following have not been reported in cacti.
These are included below only for structural comparisons.

Abbreviations are summarized at the end of the table.

Generic ring structures
are located above and farther below.

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A = Lupenes;    

B = Sterols;

C, D & E = Oleanes

Name   Ring   R1   R2      R3   R4   R5   R6   R7   R8   R9  Other bonds  3-β-Hydroxy-11α,12α-epoxyoleanan-28,13B-olide C OH Me HH HH -O-C(O)- HH HH Me Me C11-O-C12  Alamosenogenin C  OH  Me HH OHH CHO HH HH  CH2OH Me  β-Amyrin  C OH Me  HH  HH H  MeH  HH Me  Me  Betulinic acid A OH Me Me H CO2H HH H =CH2 H  Betulin A OH Me Me H CH2OH HH H =CH2 H  Bridgesigenin A C OH Me -O-C(O)-(to R5) HH (from R3) HH HH CH2OH Me  Bridgesigenin B C OH Me -O-C(O)-(to R5) HH (from R3) HOH OHH CH2OH Me  Bridgesigenin C C OH Me -O-C(O)-(to R5) HH (from R3) HOH AcOH CH2OH Me  Calenduladiolacc. to Kircher 1980 A OH Me Me OH Me H HH =CH2 H  Calenduladiolacc. to Kasprzyk et al 1970 A OH Me Me OH Me H HH =CH2 OH  Campesterol B OH Me H H Me Me na na na C5=C6  Chichipegenin C OH Me HH OHH CH2OH OHH HH Me Me  Cholestane B H H H H H Me na na na all saturated  Cholestanol B OH H H H H Me na na na all saturated  Cholesterol B OH H H H H Me na na na C5=C6  Cochalic acid C OH Me HH OHH CO2H HH HH Me Me  Cyclostenol B OH H OH Me H -C(H2)-(to C9) na na na all saturated  Dumortierigenin C OH Me -O-C(O)-(to R5) HH (from R3) OHH HH Me Me  Epithelanthate D OH Me na na na na na na na  Erynginol A C OH Me HH OHH CH2OH OHH OHH CH2OH Me  Erythrodiol C OH Me HH HH CH2OH HH HH Me Me  Friedelan-3α-ol C OH Me HH HH Me HH HH Me Me No Me at C1Me at C4, C13 & C18  Friedelin C =O Me HH HH Me HH HH Me Me No Me at C1Me at C4, C13 & C18  Gummosogenin C OH Me HH OHH CHO HH HH Me Me  Longispinogenin C OH Me HH OHH CH2OH HH HH Me Me  Lophenol B OH H H H H Me na na na 7=8  Lupenetriol A OH Me Me OH CH2OH H H =CH2 H  Lupeol A OH Me Me H Me HH H =CH2 H  Macdougallin B OH Me OH Me H Me na na na 8=9  Machaeric acid C OH Me H H CO2H H =O Me Me  Machaerinic acid C OH Me HH HH CO2H HH OH Me Me  Machaerogenin C OH Me HH HH -C(O)-O-(to R7) HH (from R5)H CH2OH Me 12=13  Maniladiol C OH Me HH OHH Me HH HH Me Me  Methyl betulinate A OH Me Me H COOMe HH H =CH2 H  Methyl epithelanthate D OH Me na na na na na na na  Methyl machaerinate C OH Me HH HH COOMe HH =O Me Me  Methyl oleanolate C OH Me HH HH COOMe HH HH Me Me  Methyl queretaroate C OH Me HH HH COOMe HH HH CH2OH Me  Myrtillogenic acid C OH Me H OH CH2OH H H CH2OH Me  Oleanolic acid C OH Me H H CH2OH H H Me Me  Oleanolic aldehyde C OH Me HH HH CHO HH HH Me Me  Pachanol A E OH Me Me HH -C(O)-O-(to R7) HH (from R5)H CH2OH Me C12=C13C14=C15  Pachanol B E OH Me Me HH -C(O)-O-(to R7) OHH (from R5)H CH2OH Me C11=C12>C13=C18  Pachanol C E OH Me Me HH -C(O)OH HH AcOH CH2OH Me C12=C13OH at 14  Pachanol D E OH Me Me HH -C(O)-O-(to C14) OHH HH CH2OH Me C12=C13  Peniocerol B OH H OH H H Me na na na C8=C9  Queretaroic acid C OH HH HH H CO2H HH HH CH2OH Me  Queretarol C OH H H H CH2OH H H CH2OH Me  Schottenol B OH H H H Et Me na na na C7=C8  α-Sitosterol B OH Me H H Et Me na na na C8=C9  β-Sitosterol B OH H H H Et Me na na na C5=C6  α-Spinasterol B OH H H H Et Me na na na C7=C8C22=C23  Stellatogenin A OH Me Me H -C(O)-O-(to R7) HH (from R5)OH Me H  Stenocereol B OH H OH Me H Me na na na C8=C9C22=C23  Stigmasterol B OH H H H H Me na na na C5=C6C22=C23  Taraxerol C OH Me HH HH Me HH HH Me Me C14=C15No Me at C14Me at C13 & C18  Thurberin A OH Me Me H Me HH H =CH2 H  Thurberogeninacc to Hegnauer A OH Me Me H -C(O)-O-(to R7) HH (from R5) =CH2 H  Thurberogeninacc to Kircher A OH Me Me H -C(O)-O-(to R6) (from R5)H H =CH2 H  Thurberol B OH H OH H H Me C8=C9C14=C15  Treleasegenic acid C OH Me HH HH CO2H HH OHH CH2OH Me Abbreviations for Triterpenoid & Sterol Key: Stereochemistry is not reflected in table unless indicated in structural diagram. =: Indicates position of a double bond. Et: Ethyl: -C2H5 A, B, C, or D: Ring structure(see diagrams at top and bottom of page) “from R#”: Indicates where it is linked to. AcO: Acetyl H: Hydrogen C#: Indicates specific carbon atom Me: Methyl: -CH3 CO2H: COOH: Carbonyl na: Not applicable COOMe: Methyl ester OH: Hydroxy CHO: Formyl “to R#”: Indicates where is is bonded. -O-: Epoxy