ABSTRACT
OH
(2) R1 = Me ---- Ouratea spectabilis, Ref. 28 (3) R1 = H ---- Ouratea hexasperma, Ref. 33
I
II
O
OOH
MeO
OMe
(4) Anacarduflavanone — Semecarpus anacardium Linn., rel. config., Ref. 18
I
II3' 8
OMe
O
MeO OH
O
O O
O
OOH
R1O
OR2
OR3
I
II3' 8
O
OH
O
O
(5) R1 = R2 = R3 = H — Pyranoamentoflavone — Calophyllum inophylloide, Ref. 19 (6) R1 = Me, R2 = R3 = H (7) R1 = R3 = H, R2 = Me (8) R1 = R3 = Me, R2 = H (9) R1 = R2 = Me, R3 = H
— Calophyllum venulosum, Refs. 20,21
O
OOH
MeO
OMe
(10) R1 = H (11) R1 = Me
I
II3' 8
O
OH
O
OR1
HO
— Taxus baccata, Ref. 22
Amentoflavone is the free phenolic form of compound (11)
O
OOH
MeO
OH
(12) (I-2S,II-2S)-I-7,II-7-Di-O-methyltetrahydroamentoflavone — Rhus retinorrhoea, abs. config., Ref. 23
I
II3' 8
O
OH
O
OH
MeO
O
OOH
HO
OH
(13) R1 =
I
II3' 8
O
OH
O
OH
HO R1
HO
— Calophyllum venulosum, Ref. 21 (14) R1 =
O
OOH
MeO
OH
(15) Amentotaxus yunnanensis, rel. config., Ref. 44
I
II3' 8
O
OH
O
OH
MeO
Chemistry, Biochemistry, and
(Bineoflavones)
17.3.1.4 Biauronols and Biaurones
Chemistry, Biochemistry, and
17.3.1.6 (I-6,O,II-8)-Biflavones
O
OOH
HO
OH
O
OOH
HO
OMeI
II
(43) Philonotisflavone-II-4-methyl ether — Mnium hornum, Ref. 87
OH
OH
17.3.1.8 (I-2’,II-6)-Biflavones and Aurone-Flavones
O
OOH
HO
OH
I
O
O
OH OH
OHHO
OH
II
(44) Tetrahydrodicranolomin — Pilotrichella flexilis, abs. config., Ref. 71
OH
I
O
O
OH OH
OHHO
OH
II
2' 6
(45) Pilotrichellaaurone — Pilotrichella flexilis, abs. config., Ref. 71
O
O HO
HO
O
OOH
HO
OH
I
O
O
OH
OHHO
OH
II
(46) 3-Desoxydicranolomin (47) I-2,3-Dihydro derivative
— Plagiomnium undulatum, Ref. 85
O
OOH
O I
O
O
OH
OHO
II
O
OH
(48) Leucaediflavone — Leucaena diversifolia, Ref. 107
O
OH
Chemistry, Biochemistry, and
17.3.1.10 (I-4’,O,II-8)-Biflavones
17.3.1.11 (I-3,O,II-4’)-Biflavones
O
OOH
HO
O
OH
OH
O OH
HO
3I II
(56) Lanceolatin A — Lophira lanceolatum, rel. config., Ref. 83
H
H
17.3.1.13 (I-2’,II-2’)-Biflavonols
O
OOH
HO
O
OH
OH
O OH
HO
2 2II I
(57) Garcinia nervosa, Ref. 108
17.3.1.14 (I-3’,II-3’)-Biflavones
O
OOH
HO O
OH
OH
O OH
HO
3' 3'I
II
(58) Hypnogenol B1 — Hypnum cupressiforme, rel. config., Ref. 34
OH
HO
O
OOH
HO O
OH
OH
O OH
HO
3' 3'I
II
(59) 2,3-Dihydroapigeninyl-(I-3',II-3')-apigenin — Homalothecium lutescens, rel. config., Ref. 40
17.3.1.15 Bi-Isoflavonoids
O
O
O
OH OH
HO H
OH
OH
O
O
OH
I
II
(60) Lupinus albus L., rel. config., Ref. 12
HO (61) Lupinus albus L., rel. config., Ref. 12
O
O
O
OH
HO H
OH
I
8 O
O
HO OH
OH
II
Chemistry, Biochemistry, and
17.3.1.16 Chamaejasmins [(I-3,II-3)-Coupling]
O
OOH
HO
OH
I O
O
OH
OH
II
HO
(73) Mogathin (I-3-hydroxycupressuflavone) — Glossostemon bruguieri (Desf.), Ref. 9
OH
17.3.1.18 Flavanone-Auronols
O
O O
OH
OH
HO OH
HO
OHO OH
I
II
(74) Diastereoisomer shown (75) (II-2)-S-epimer — Berchemia zeyheri, abs. config., Refs. 35, 36
O O
O
OH
OH
HO
HO OH
O
HO I
II 3 2
(76) Diastereoisomer shown (77) (II-2)-S-epimer
—Berchemia zeyheri, abs. config., Ref. 37
OH
17.3.1.19 Flavanone and Flavone-Chalcones
Chemistry, Biochemistry, and
17.3.1.20 Flavanone-Isoflavans
O
OH
HO
O
O
OH
HO O
OHOH
I
II
(92) Garcinianin atropisomers — Garcinia kola, rel. config., Ref. 69
O
OH
HO
O
O
OH
HO O
OMeOH
I
II
(93) GB-2a-II-4'-OMe — Rheedia gardneriana, rel. config., Ref. 70
OH
O
OH
HO
O O
HO O
OHOH
I
II
(94) (+)-GB-lb — Garcinia kola, abs. config., Ref. 72 OH
O
OH
HO
O
O
OH
HO O
OHOH
I
II
(95) Pancibiflavonol — Callophyllum panciflorum, rel. config., Ref. 73
O
OH
HO
O O
OH
HO O
OH
I
II
(96) GB-4, (I-2R,3S; II-2R,3R) (97) GB-4a, (I-2S,3R; II-2R,3R)
OH
OH
OH HO
— Gnidia involucrata, abs. config., Ref. 74
17.3.1.22 Hinokiflavones [(I-4’,O,II-6)-Coupling]
O
O
OH
MeO
O
O
OMe
HO
OH
O I II
4' 6
(98) I-7,II-7-Di-O-methyltetrahydrohinokiflavone — Cycas beddomei, abs. config., Ref. 80
Chemistry, Biochemistry, and
O
O
OH
HO
O
O
OMe
HO
OH
O I II
4 6
(99) 2,3-Dihydroisocryptomerin — Selaginella delicatula, rel. config., Ref. 10
17.3.1.23 Isoflavanone-Auronols [(I-2,II-7)-Coupling]
O
O
HO
HO
OH OH
OH
OH
O
OH
O
I
II
2 7
(100) Diastereoisomer shown (101) (II-2)-S-epimer
— Berchemia zeyheri, abs. config., Refs. 35, 36
17.3.1.24 Ochnaflavones [(I-3’,O,II-4’)-Coupling]
O
OH
OH
HO
O O
O
OR1
OH
O 3
4 I
II
(102) R1 = H — Luxemburgia nobilis (EICHL), rel. config., Refs. 14, 77 (103) R1 = Me — Ochna integerrima, rel. config., Ref. 77
O
OR3
OR1
R2O
O O
O
OR4
OR1
O 3
4I
II
(104) R1 = R2 = R3 = R4 = H (105) R1 = R3 = R4= H, R2 = Me (106) R1 = H, R2 = R3 = R4 = Me — Ochna beddomei, rel. config., Ref. 78
— Ochna obtusata, rel. config., Ref. 75
O
OH
OH
MeO
O O
O
OR1
OH
O 3'
4'I
II
(107) R1 = H — Ochna beddomei, abs. config., Ref. 76 (108) R1 = Me — Quntinia acutifolia, rel. config., Ref. 79
17.3.1.25 Robustaflavones [(I-3’,II-6)-Coupling]
O
OOH
MeO
OHO
OMe
O
OMe
OH
3' 6 I
II
(109) Selaginella delicatula, rel. config., Ref. 10
O
OOH
R1O
OHO
OH
O
OMe
OH
3' 6 I
II
— Selaginella delicatula, Ref. 11(110) R 1 = H
(111) R1 = Me
MeO O
OOH OHO
OR1
O
OMe
OH
3' 6 I
II
— Selaginella delicatula, rel. config., Ref. 11(112) R 1 = H
(113) R1 = Me
O
OOH
HO
OHO
OMe
O
OMe
OH
3' 6 I
II
(114) Dysoxylum lenticellare, Ref. 15
O
OOH
HO
OHO
OH
O
OH
OH
3' 6
I
II
(115) Plagiomnium undulatum, rel. config., Ref. 85
OH
OH
Chemistry, Biochemistry, and
O
OOH
MeO
OH
I
II
O
O
OH
OMe
HO
6 6
(116) 6,6''-Bigenkwanin — Ouratea spectabilis, Ref. 28
O
O
OH
I
II
O
O
OH
HO
6 6
(117) Albiproflavone — Albizia procera, Ref. 107 Note the naphthopyrano functionalities.
