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.

It may be easiest to open whichever image you need in a new window?

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

 

 

triterpenoids generic ring A

 

triterpenoid_generic_B

triterpenoid_generic_C

triterpenoid_generic_D

triterpenoid_generic_E