Triterpenoids - The Mushroom Hunter

Triterpenoids
Joseph D. Connolly and Robert A. Hill
Department of Chemistry, Glasgow University, Glasgow, UK G12 8QQ
Received (in Cambridge, UK) 21st August 2003
First published as an Advance Article on the web 23rd October 2003
Covering: 2001. Previous review: Nat. Prod. Rep., 2002, 19, 494
This review covers the isolation and structure determination of triterpenoids including squalene derivatives,
lanostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes,
friedelanes, ursanes, hopanes, fernanes, sipholanes, isomalabaricanes, serratanes and saponins. The literature from
January to December 2001 is reviewed and 242 references are cited.
1 Introduction
2 The squalene group
3 The lanostane group
4 The dammarane group
4.1 Tetranortriterpenoids
4.2 Quassinoids
5 The lupane group
6 The oleanane group
7 The ursane group
8 The hopane group
9 Miscellaneous compounds
10 References
1 Introduction
The biological activities of triterpenoids continue to be of
interest. Reviews have appeared on the aphrodisiac properties
of the triterpenoids from Panax ginseng, 1 the biological activities
of triterpenoids from liquorice root 2 and antimycobacterial
plant terpenoids. 3 The anti-tumourogenic properties
of ursolic acid 4 and the possible use of celastrol for the treatment
of Alzheimer’s disease 5 further emphasise the biological
importance of triterpenoids. The use of terpenoids, including
triterpenoids, as chemosystematic markers in conifers has been
discussed. 6
2 The squalene group
Armatols A–F 1–6 are brominated squalene derivatives from
the Indian Ocean alga Chondria armata. 7 The complete stereochemistry
of the epoxysqualene tritetrahydrofurandiol 7 from
Spathelia glabrescens 8 has been confirmed by synthesis. 9 Concentricol
8 is a squalene hexol from Daldinea concentrica. 10 The
bis-epoxide auriculol 9 has been isolated from Dolabella auricu-
640 Nat. Prod. Rep., 2003, 20, 640–659
This journal is © The Royal Society of Chemistry 2003
DOI: 10.1039/b204068a

laria. 11 Four new squalene ethers have been found in Laurencia
viridis. 12 These include martiriol 10, pseudodehydrothyrsiferol
11, dioxepandehydrothyrsiferol 12 and 16-epihydroxydehydrothyrsiferol
13. Four irregular triterpenoids 14–17 have been
isolated from the marine diatom Rhizosolenia setigera. 13
Testudinariols A 18 and B 19 from Pleurobrancus testudinarius
have been synthesised. 14 The absolute configuration of
longilene peroxide 20, isolated from the wood of Eurycoma
longifolia, has been established by synthesis. 15 Molecular modelling
studies have revealed that the original structure proposed
for glabrescol 21 is not the most thermodynamically stable and
therefore synthetic evidence was very important in the structure
elucidation. 16
The squalene cyclase from the bacterium Zymomonas mobilis
demonstrates its lack of specificity by producing a range of
polycyclic metabolites including α- and γ-polypodatetraenes 22
and 23, dammara-20,24-diene 24, 17-isodammara-12,24-diene
25, eupha-7,24-diene 26, hop-17(21)-ene 27, neohop-13(18)-ene
28, 17-isodammara-20,24-diene 29, neohop-12-ene 30, fern-8ene
31, diploptene 32, and hop-21-ene 33. 17
3 The lanostane group
Alisol F 24-acetate 34 is a new protostane from Alisma orientalis.
18 New metabolites of Ganoderma lucidum include
lucidenic acid N 35 (lucidenic acid LM1) and methyl lucidenate
F 36. 19 Three new pentanorlanostane derivatives, cladosporides
B 37, C 38 and D 39, have been isolated from a Cladosporium
sp. 20 Cladosporides A and B show antifungal activity against
Aspergillus fumigatus. A new 21,24-cyclolanostane derivative 40
has been reported from the wood rotting fungus Inonotus
obliquus. 21 Fuscoporianol A, which is the 25-O-methyl ether of
40, occurs in Fuscoporia obliqua together with B 41 and C 42. 22
The structure of fuscoporianol A was confirmed by X-ray
analysis. The structure of ananosic acid A 43, an unusual
rearranged lanostane from the stem bark of Kadsura ananosa,
has been confirmed by X-ray analysis. 23 Other new lanostanes
include the trienes 44 and 45 from Guarea rhophalocarpa, 24 sublateriols
A 46, B 47 and C 48 from the edible mushroom
Naematoloma sublateritium 25 and 3β,24-dihydroxy-24-methyllanost-8-en-30-oic
acid 49, together with the lanostane saponin
formoside B, from the Caribbean sponge Erylus formosus. 26
Feroxosides A 50 and B 51 are nor-lanostane saponins from
Ectyoplasia ferox. 27 Erylosides G–J, lanostane saponins from
the sponge Erylus nobilis, have new genins 52 and 53. 28 Colossolactones
A–G 54–60 form an interesting series of lanostanes
and modified cycloartanes from the mushroom Ganoderma
colossum. 29 It should be noted that colossolactone A 54 is not
actually a lactone. Schiprolactone A 61, from Schisandra
propinqua, has a novel side chain. 30
Nat. Prod. Rep., 2003, 20, 640–659 641

642 Nat. Prod. Rep., 2003, 20, 640–659
Two unusual cleaved cycloartanes, pseudolarolides E 62 and
F 63, have been reported from Pseudolarix kaempferi. 31 Their
structures were established by X-ray crystallographic analysis.
Five 29-nor-3,4-seco-cycloartanes 64–68 have been isolated
from Antirhea acutata. 32 The aerial roots of Ficus microcarpa
contain the 27-nor-derivative 69 and the 25,26,27-trinorderivative
70. 33 Compound 71 and cycloabyssinone 72 are
nor-cycloartanes from Artemisia caruifolia 34 and Harrisonia
abyssinica, 35 respectively. Other new cycloartanes include
tillandsinone 73 and cyclolaudenyl formate 74 from Tillandsia
fasciculata, 36 the acetate 75 from Dysoxylum malabaricum, 37
and compounds 76 and 77, together with many triterpenoid

esters, from the flowers of Chrysanthemum morifolium. 38
Thalictoside F is a new saponin from Thalictrum thunbergii
with the new genin 78, the 21,24-diepimer of thalictoside E. 39
The full details of the structure elucidation of thalictosides D
and E are included in this paper.
The constituents of Cimifuga species have been reviewed. 40
Four new saponins, bugbanosides C 79, D 80, E 81 and F 82
have been isolated from Cimifuga simplex. 41 A new cimigenol
glycoside 83 and two trinor-derivatives 84 and 85, with new
genins, have been reported from Cimifuga dahurica. 38,42 Actaeaepoxide
3-β-d-xylopyranoside 86 is a new glycoside from
Actaea racemosa (Cimifuga racemosa). 43 Other new compounds
from Cimifuga racemosa include 87–97 44 and 25-O-methylcimigenol
3-O-α-l-arabinopyranoside (cimiracemoside B). 45
2-O-acetylactein 92 and 2-O-acetyl-27-deoxyactein 93 are
constituents of Cimifuga foetida 46 while 22R-hydroxycimifugol
94 and the shengmanol derivative 95 are found in Cimifuga
acerina. 47
Nat. Prod. Rep., 2003, 20, 640–659 643

644 Nat. Prod. Rep., 2003, 20, 640–659
Askendosides G and A and cycloglobiceposide B are known
cycloartane saponins from Tragacantha stipulosa. 48 Astragalus
prusianus contains two new saponins prusianosides A 96 and
B 97. 49 New cycloartane saponins have also been reported
from Astragalus trojanus (trojanosides I–K) 50 and Astragalus
caprinus. 51
Liouvillosides A and B are sulfated holostane glycosides
from Staurocamis liouvillei. 52 Patagonicoside A, a holostane
glycoside with a new aglycone 98, has been isolated from Psolus
patagonicus. 53 The aglycone 99 of frondoside F, a minor
saponin constituent of the sea cucumber Cucumaria frondosa,
contains an unusual 18 22 lactone. 54
Neocucurbitacins A 100 and B 101, from the Brazilian folk
medicine “Buchinha” (Luffa operculata), have an inhibitory
effect on some gene expression in a human osteoblast-like cell
line. 55 Momordica charantia is a rich source of triterpenoid
saponins. The new cucurbitacin derivatives, goyaglycosides
A–H 102–109, were accompanied by known cucurbitane

saponins and oleanane saponins (goyasaponins I–III). 56 The
aldehyde 110 has been obtained from an extract of the whole
plant of Momordica charantia. 57 Two seco-cucurbitane derivatives
111 and 112 have been isolated from Russula lepida. 58
4 The dammarane group
The structures of 15α-acetoxycleomblynol A 113, from Cleome
amblyocarpa, 59 and cabraleadiol 3-acetate 114, from Aglaia
lawii, 60 have been established by X-ray analysis. The 20S,24S
stereochemistry of cabraleadiol is thus established. Other new
dammaranes include 115 and 116 from the fruits of Forsythia
suspensa 61 and semialactone 117, isofouquierone peroxide 118
and fouquierone 119 from Rhus javanica. 62
New dammarane saponins continue to appear. The hexanorderivative
notoginsenoside R 10 120 has been found in the roots
of Panax notoginseng. 63 Ginsenosides Rh 5 121, Rh 6 122, Rh 7
123, Rh 8 124 and Rh 9 125, from the leaves of Panax ginseng, all
apart from Rh 7 123 have new genins. 64 Polysciasoside A 126,
from Polyscias fulva, is a saponin of 3β,16β,20S-trihydroxydammar-24-en-12-one.
65 Two new glycosides, notoginsenosides
T 1 127 and T 2 128, have been isolated following mild acidic
hydrolysis of the crude root saponins of Panax notoginseng. 66 A
method for regioselective enzymatic galactosylation and glucosylation
of protopanaxatriol ginsenosides has been published. 67
Papers on new dammarane saponins include bacopasides I and
II from Bacopa monniera, 68 quinquenosides L 1, L 2 and L 9 from
the leaves and stems of Panax quinquefolium, 69 notoginsenosides
L, M and N from Panax notoginseng, 70 ginsenosides I and
II from the flower buds of Panax ginseng 71 and ginsenoside Rh 5
and vina-ginsenoside R 25 from Panax vietnamensis. 72
Nat. Prod. Rep., 2003, 20, 640–659 645

A new homocyclotirucallane, sinetirucallol 129, has been
isolated from Spiranthes sinensis. 73 Its structure was established
by X-ray analysis. Eight new tirucallanes, dyvariabilins A–H
130–137, have been reported from Dysoxylum variabile 74 while
646 Nat. Prod. Rep., 2003, 20, 640–659
another, 138, was found in Dysoxylum malabaricum. 37 Other
compounds in this series include the apotirucallane 139 from
Azadirachta indica, 75 the 14,18-cycloapotirucallanes 140 and
141 from Guarea jamaicensis 76 and the nor-derivatives malabanones
A 142 and B 143 from Ailanthus malabarica. 77
4.1 Tetranortriterpenoids
Many new limonoids have appeared this year. The three hirtin
derivatives 144–146, from Trichilia pallida, show antifeedant
activity. 78 Meliacinolactol 147, limocin C 148 and limocin D
149 are further constituents of Azadirachta indica. 79 Further
rearranged limonoids from Harrisonia perforata include
haperforins C2 150, F 151 and G 152. 80 Their structures were

determined by X-ray analysis, as were those of 7-isovalerylcycloseverinolide
153 and 7-isovalerylcycloepiatalantin 154
from the root bark of Severinia buxifolia. 81 Pterorhachis zenkeri
contains 9β-amoorstatin 155 and 3-deacetylamoorstatin 156. 82
The ring D unsaturated δ-lactone, deoxyobacunone 157, from
the root bark of Harrisonia abyssinica, shows stimulatory activity
against Striga hermonthica seeds. 83 Other new limonoids
include cedrellin 158 from Cedrela sinensis, 84 shihulimonin A
159 (previously isolated in 1965 and named limonexic acid)
from Evodia rutaecarpa, 85 21-O-methyllimonexic acid 160 and
8,14-epoxyfraxinellone 161 from Raulinoa achinata 86 and 1-Omethylichangensin
162 and sudachinoids A 163, B 164 and C
165 from Citrus sudachi. 87 Polygonumins A 166 and B 167
are the E- and Z-feruloyl esters of desacetylnomilin from
Polygonum orientale. 88 1,2-Dihydroamoorinin 168 is a new
limonoid from Aphanamixis polystacha. 89 Three new ring C
cleaved derivatives, melianol 169, desfuranodesacetylnimbin-
17-one 170 and meliatetraone 171, have been reported from the
leaves of Azadirachta indica. 90
Nat. Prod. Rep., 2003, 20, 640–659 647

The full details for the structures of khayanolides A and B,
from Khaya senegalensis, have appeared and a new compound,
khayanolide C 172, has also been obtained. 91 In a separate
paper, three further derivatives, 1-O-acetylkhayanolide 173,
khayanone 174, and 2-hydroxyseneganolide 175, are described
from Khaya senegalensis. 92 The structures of two limonoids,
febrifugin 176 and cipadesin 177, from Cipadessa baccifera,
have been confirmed by X-ray analysis. 93
648 Nat. Prod. Rep., 2003, 20, 640–659
4.2 Quassinoids
New quassinoids include cedronolactone 178 from Simaba
cedron, 94 12-epi-11-dehydroklaineanone 179 from Eurycoma
longifolia, 95 iandonoside A 180, B 181 and iandonone 182 from
Eurycoma harmandiana 96 and 16β-O-methylneoquassin 183
and 16β-O-ethylneoquassin 184 from the wood of Picrasma
crenata. 97
5 The lupane group
Sachunoside is a seco-abeo-lupane saponin from Acanthopanaz
divaricatus var. sachunensis. 98 The aglycone is sachunogenin
185. The acid 186 and hydroperoxide 187 occur in Ficus microcarpa.
99 Other new lupanes include 6α-hydroxybetulinic acid
188 from Eugenia moraviana, 100 lup-20(29)-ene-1β,2α,3β-triol
189 from Cephalomappa sinensis, 101 21-hydroxylupa-1,12-dien-
3-one 190 from the roots of Hemidesmus indicus, 102 and 2α,6βdihydroxybetulinic
acid 191 (isolated in 1999 as divergioic acid)
and 6β-hydroxyhovenic acid 192, which is the aglycone of
quadranoside II, from Combretum quadrangulare. 103 The 3,7dibenzoate
193 and the 7-benzoate 194 of 3α,7β-dihydroxylup-
20(29)-en-28-oic acid have been isolated from the stem bark
of Picramnia teapensis. 104 Ulmicins A–E 195–199 are lupane
esters from Ulmus davidiana var. japonica. 105 Other esters
include 200 from Mimusops elengi, 106 lawsonic acid 201 from

Lawsonia alba, 107 and 202, 203 and a range of 3-O-acyl esters of
lupeol from Parahancornia amapa. 108 The twig bark of Pyrus
serotina contains a further five fatty esters of lupeol. 109 Four
lupane saponins, isolated from Pulsatilla chinensis, include one
new genin 3β,20,23-trihydroxylupan-28-oic acid 204. 110 Coccinioside
K is a betulinic acid saponin from Coccinia indica 111 and a
lupane saponin has been isolated from Arenaria filicaulis. 112
6 The oleanane group
Trypterygium wilfordii is a rich source of oleanane, friedelane
and ursane triterpenoids. 113 In addition to the nor-oleanane 205
and the seco-oleanane 206, it produces the lactone 207, the
carboxylic acids 208–211, the friedelanes 212 and 213 and the
nor-friedelane 214. Interestingly, compounds 212 and 213 have
Nat. Prod. Rep., 2003, 20, 640–659 649

an additional two carbon fragment attached to C-6. The lactones
melliferone 215, 216 and patrinolide A 217 have been
reported from Brazilian propolis (Myrceugenia euosma), 114
Nigella sativa 115 and Patrinia scabiosaefolia, 116 respectively. The
range of polyhydroxyoleanenoic acids includes the triol 218
from the fruit of Rosa davidii, 117 the tetrol buergericic acid 219
from Rubus buergeri, 118 6β-hydroxyarjunic acid 220 from
Combretum quadrangulare, 103 the triol 221 from Eriobotrya
deflexa 119 and cucubalugenin A 222 from Cucubalus baccifer. 120
Hemidesmusyl acetate 223, from Hemidesmus indicus,
apparently lacks a C-3 oxygen substituent 102 as does the 27-noraldehyde
224 from the roots of Lavandula stoechas ssp.
stoechas. 121 It is accompanied by the aldehyde 225. 3,21-
650 Nat. Prod. Rep., 2003, 20, 640–659
Dioxoolean-18-en-28-oic acid 226 is a constituent of Acacia
aulacocarpa. 122 The 3,4-seco-derivative 227 has been isolated
from Phoradendron reichenbachianum. 123 The 3β,22α-diol,
α-sophoradiol 228, has been reported from the stem of
Erythrina sigmoidea. 124 The hydroperoxide 229 has been found
in the aerial roots of Ficus microcarpa. 99
Papers have appeared on the triterpenoids of the stem bark
of Albizzia versicolor and A. schimperana, 125 pyrotechnoic acid
230, an ether of oleanolic acid from Leptadenia pyrotechnica, 126
and tetra-, penta- and hexadecanoyl esters of oleanolic acid. 127
Four new esters 231–234 have been reported from Lippia
turbinata 128 and one 235 from Eugenia sandwicensis. 129 The

Table 1 New oleanane saponins
Compound(s) Source Ref.
Albiziatrioside A Albizia subdimidiata 142
Anhuienosides A–F Anemone anhuiensis 143
Araliasaponins V–IX Aralia elata 144
Arjunetoside Terminalia arjuna 145
Basellasaponins A–D Basella rubra 146
Beesioside Q Beesia calthaefolia 147
Bidentatoside I Achyranthes bidentata 148
Bidentatoside II Achyranthes bidentata 149
Calendsaponins A–D Calendula officinalis 150
Centellasaponin D Centella asiatica 151
Chikusetsusaponin V methyl ester Achyranthes bidentata 149
Clematibetosides A–C Clematis tibetana 152
Colchisides A and B Hedera colchica 153
Conyzasaponins A–G Conyza blinii 154
Congmunosides V, VII, XV, XVI Aralia elata 155
Crataegioside Rubus crataegifolius 156
Eclalbasaponins XI and XII Eclipta prostrata 157
Eclabatin Eclipta alba 158
Escins Ivg, Ivh and Vib Aesculus chinensis 159
Eupteleasaponin VI–XII Euptelea polyandra 160
Glycoside D 2 Fatsia japonica 161
Glycosides L–C2 and L–I 2 Scheffleropsis angkae 162
Glycosides St–C 2, St–D 1, St–D 2 Tetrapanax papyriferum 163
Glycosides St–E 2, St–F 2, St–J 2, St–K 2 Tetrapanax papyriferum 164
Glycosides St–H 2, St–I 2 Tetrapanax papyriferum 165
Junceosides A–C Arenaria juncea 166
Latifolosides I–Q Ilex latifolia 167
Maetenosides A and B Maesa tenera 168
Pisumsaponins I and II Pisum sativum 169
Prostratosides D and E Polycarpon prostratum 170
Prostratosides F–H Polycarpon prostratum 171
Protoprimuloside B Primula elatior 172
Saikosaponin q-1 Bupleurum chinense 173
Saikosaponins V-1 and V-2 Bupleurum chinense 174
Securiosides A and B Securidaca inappendiculata 175
Sinofoside A Sinofranchetia chinesis 176
Subcapitatosides B and C Aralia subcapitata 177
Tanguticosides A and B Clematis tangutica 178
Vitaboliside A 2-methylglucuronate Albizia gummifera 179
Zygoeichwaloside I Zygophyllum eichwaldii 180
complete proton and carbon NMR assignments of several
oleanane and ursane triterpenoids from Mentha villosa have
been published. 130 Crystal structures have been published
for wilforlide A 130 from Trypterygium wilfordii 131 and 3βmethoxyolean-18-ene
(meliacin) from the marine fungus
Chaetomium olivaceum. 132
The 24,30-dinor-oleanane derivative 236 has been found in
Paeonia delavayi 133 while the 24,28-dinor-compound remangilone
D 237 occurs in Physena madagascariensis. 134 A 27-nor-
oleanane 238 has been reported from the stem bark of Vitis
vinifera. 135
Camelliosides A–D are oleanane saponins, from Camellia
japonic, with known genins. 136 An X-ray crystal structure analysis
of camellenodiol, the genin of camelliosides A and B,
revealed that it is 239 with a 28β- and not an 18β-hydroxyl
group. The structure of the corresponding ketone, camellendionol,
should be revised to 240. Three saponins, one of
which has the new genin gymnemagenol 241, have been isolated
from Gymnema sylvestre. 137 A new saponin anemoside B
together with a new oleanane anemonolide 242 have been
reported from Anemone rivularis. 138 Fargosides A–E are new
saponins from Holboellia fargesii. 139 Fargoside B has a new
genin, the 29-nor-oleanane derivative 243. The new saponin
244, from Terminalia arjunis, also has a new genin. 140 Centellasaponin
A, from Centella asiatica, has the new genin 245. 141
New oleanane saponins that have been assigned trivial names
are listed in Table 1.
Nat. Prod. Rep., 2003, 20, 640–659 651

New oleanane saponins, that have not been assigned trivial
names, have been isolated from: Acanthophyllum squarrosum, 181
Astragalus trigonus, 182 Bellis perennis, 183 Chenopodium quinoa, 184
Elattostachys apetala, 185 Fagonia cretica, 186 Fatsia japonica, 187
Glycyrrhiza sp., 188 Isertia pittieri, 189 Ixeris sonchifolia, 190a Koelreueria
paniculata, 190b Phytolacca americana, 191 Sanguisorba
officinalis, 192 Sapindus emarginatus, 193 Schefflera arboricola 194
and Terminalia alata. 195
The structure of the multiflorane derivative 246 from
Momordica cochinchinensis has been confirmed by X-ray analysis.
196 Sandorinic acids A 247, B 248 and C 249 are three
multifloranes from Sandoricum indicum. 197
Two seco-friedelanes 250 and 251 have been isolated from the
leaves of Austroplenckia populnea. 198 The nor-seco-derivative
252 is accompanied in Tripterygium wilfordii by the known
652 Nat. Prod. Rep., 2003, 20, 640–659
acetal 3,24-epoxy-24-ethoxy-2-hydroxyfriedelan-29-oic acid,
whose structure was confirmed by X-ray analysis. 199 A dinorfriedelane,
6α-hydroxytriptocalline A 253, has also been isolated
from Tripterygium wilfordii. 200 Other new friedelanes
include calotropfriedelenyl acetate 254 from Calotropis
procera, 201 3-methoxyfriedel-2-en-1-one 255 from Salacia
petenensis 202 and three 27,16α-lactones 256–258 from Mallotus
repandas. 203 The structure of lactone 257 was confirmed by
X-ray analysis. The bis-friedelane derivative scutionin αB 259
has been reported from Maytenus blepharodes and M. magellanica
together with the corresponding 6,7-dihydro- and
6β-methoxy-6,7-dihydro-derivatives. 204
7 The ursane group
Two ursane hydroperoxides 260 and 261 and a cyclic peroxide
262 have been isolated from Ficus microcarpa. 99 The structure
of 262 was confirmed by X–ray analysis. The aerial roots of
Ficus macrocarpa contain two 13,27-cycloursanes 263 and
264. 33 The structure of the former was confirmed by X-ray
analysis. Swinhoeic acid 265 is an unusual 18,19-seco-ursane

from Rubus swinhoei. 205 The 16,17-seco-derivatives secohemidesursenyl
acetate 266 and seco-hemideursenol 267, from
Hemidesmus indicus, 102 and the 14,15-seco-compound 268, from
Pluchea lanceolata, 206 have also been reported. Six antiandrogenic
ursanes: cordiaketals A 269 and B 270, cordianone
271 and cordianals A 272, B 273 and C 274, have been isolated
from the leaves of the Brazilian plant Cordia multispicata. 207
The highly oxygenated 2α,3α,19α,25-tetrahydroxyursene-23,28dioic
acid 275 is a constituent of Rhaponticum uniflorum. 208
Two ursane methyl ethers 276 and 277 have been found in
Salvia roborowskii. 209 Lawsonia alba contains the feruloyl ester
278. 107 Other ursanes include: the diene 279 from Rubus
chroosepalas, 210 the lactone 280 from the fruit of Rosa davidii, 117
calotropursenyl acetate 281 from Calotropis procera, 201 actinidic
acid 282, a phytoalexin from unripe Kiwi fruit, 211 two 30-
carboxylic acids 283 and 284 from Trypterygium wilfordii, 113 the
keto-triol-acid 285 from Eriobotrya deflexa, 119 and urs-12-ene-
3β,6β,19α,23-tetrol 286 from Mimusops elengi. 106 30-Nor-urs-
12-ene-3β,19α-diol 287 is a constituent of Debregeasia salicifolia
212 while 19α,24-dihydroxy-3-oxo-12-ursen-28-oic acid 288
occurs in Rhododendron simsii. 213 The feruloyl ester 289 is found
in Eriobotrya japonica. 214
Five new ursane saponins have been reported from
Tupidanthus calyptratus, with two new genins 290 and 291. 215
Kudinosides I–P are new ursane saponins from the leaves of
Ilex kudincha. 216 Kudinolic acid 292 is the aglycone of
kudinosides I–K. Zygophyloside N is another ursane saponin
with a new genin 293, from Zygophyllum gaetulum. 217 Urs-12-
Nat. Prod. Rep., 2003, 20, 640–659 653

ene-3β,21α,28-triol 294 is the new genin of latifoloside I from
Ilex latifolia where it occurs with latifoloside J which has a
known genin. 218 The 20S-isomer of the 28-O β-d-glucopyranosyl
ester of rotundioic acid 295 has been claimed as a constituent
of the leaves of Ilex argentina. 219 Two new saponins 296 and
297, with known genins, have been isolated from Centipeda minima.
220 Other ursane saponins with known genins include centellasaponins
B and C from Centella asiatica, 151 latifolosides K
and L from Ilex latifolia bark 221 and constituents of Clematoclethra
scandens 222 and Sanguisorba officinalis. 192
The resin of Protium heptaphyllum contains the new ursane
298 together with two taraxastanes 299 and 300. 223 Three
654 Nat. Prod. Rep., 2003, 20, 640–659
new taraxastanes 301, 302 and 303 have been reported from
Saussurea petrovii. 224 The diol 302 has also been found in Picris
evae. 225 22α-Methoxyfaradiol 304 and its 3-palmitate are constituents
of the flowers of Chrysanthemum morifolium. 38

8 The hopane group
Three isomeric series of hopanoids, 17β,21β, 17β,21α and
17α,21β, have been detected in several Frankia species and other
soil bacteria. Their presence raises fundamental questions
concerning the biosynthesis of the bacteriohopanes. 226 32,35-
Anhydrobacteriohopanetetrol 305 has been identified in
Plakortis simplex. 227 Other new hopanes include 306 228 and the
nor-epoxide 307 229 from Adiantum lunulatum and the diol
acetate 308 from Aschersonia tubulata. 230 The neohopane
caffeate 309 has been reported from Filicum decipiens. 231 Spergulins
A and B are hopane saponins with known genins. 232
8α-Hydroxyfernan-25,7β-olide 310, 3α-hydroxy-4α-methoxyfilicane
311 and 19α-hydroxyferna-7,9(11)-diene 312 have been
isolated from Adiantum caudatum. 233 The complete proton and
carbon NMR assignments of fern-9(11)-en-28-oic acid have
been published. 234
9 Miscellaneous compounds
Hoogianal 313 is a new constituent of Iris hoogiana. 235 A range
of sipholane derivatives has been identified in Siphonochalina
siphonella including sipholenols F 314, G 315 and H 316, sipholenone
D 317, sipholenosides A 318 and B 319, neviotine B
320, siphonellinol B 321 and dahabinone A 322. 236 New isomalabaricane
derivatives include 323–325 from a Jaspis sponge, 237
stelliferin riboside 326 from Geodia globostellifera 238 and the 27nor-derivatives
geoditins A 327 and B 328 from Geodia
japonica. 239
Chirat-16-ene-3β,24-diol 329 has been identified in Swertia
chirata. 240 The serratane epoxides 330, 331 and 332 have been
isolated from Picea jezoensis var., jezoensis. 241 The structures of
330 and 331 were confirmed by X-ray analysis. Adiantutirucallene
B 333 and adiantulanostene B 334 are strange triterpenoids
from Adiantum venustrum. 242
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