We describe the first report of the recovery of L-iditol and Taxane from an angiosperm- Yunnanopilia longistaminata (W.Z.Li) C.Y.Wu et D.Z.Li (Opiliaceae). Two taxane compounds and L-iditol were isolated from the tender burgeon of Yunnanopilia longistaminata, and their structure were identified as Taxayunnansin B, Taxumairol E and L-iditol on the basis of NMR and MS spectrum, respectively. It is a new plant source for L-iditol and taxanes

Liu Jian-Jun

Liu Xi-Kui

English

Nature Precedings

LETTERS TO NATURE 
Letter 
New source for L-iditol and taxanes ∗
Xi-Kui Liu*, Jian-Jun Liu 
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming 
Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China 
 
Abstract: We describe the first report of the recovery of L-iditol and Taxane from 
an angiosperm- Yunnanopilia longistaminata (W.Z.Li) C.Y.Wu et D.Z.Li (Opiliaceae). 
Two taxane compounds and L-iditol were isolated from the tender burgeon of 
Yunnanopilia longistaminata, and their structure were identified as Taxayunnansin B, 
Taxumairol E and L-iditol on the basis of NMR and MS spectrum, respectively. It is a 
new plant source for L-iditol and taxanes. 
Keywords: taxane, L-iditol, new source, Yunnanopilia longistaminata 
 
Currently, plants are well recognized as a potential source of useful compounds. 
The L-iditol, because of its good function, is the food sweet flavor and the important 
raw material of intermediates with synthesis. It is present in the fruits’ juices of Genus 
Sorbus spp. in minute quantities, and able not to be extracted from the natural plant 
resources generally, and product by synthesis or ferment with the yeast1,2. The 
produce craft of it was very complicated, and the cost is very expensive. 
Taxanes are complex diterpenoids typically found in yew trees of the genus Taxus. 
The most well known taxane are paclitaxel(taxol) and docetaxel(taxoterel). Taxol was 
originally extracted from the bark of the Pacific yew (Taxus brevifolia Nutt)3,4 and 
later extracted from other related gymnosperms. Since taxol and related taxanes may 
also be produced by endophytic bacteria in yew trees such as Taxomyces andreanae3 
and Pestalotiopsis microspore4,5. Hoffman and her colleagues determined that a 
Eastern Filbert blight resistance of Gasaway tress and fungi living on it make 
paclitaxel and taxane, but only at about 10% of the concentration in yew trees. 
Limited presence of Taxol in trees other than the yew has caused manufacturers to 
depend heavily on semisynthetic production using a starting-materials compound 
closely related to Taxol and docetaxel6. Until now, taxane is harvested mainly from 
Taxus spp., and be found hardly from other plant.  
Yunnanopilia longistaminata (W.Z.Li) C.Y.Wu et D.Z.Li (Opiliaceae)7, is a 
monotype genus plant arborescently and mainly distributed along the Red River Valley at 
semitropical forests at altitudes of 900-1500 meters in Yunnan, China (see Fig.1). The tender 
burgeon and inflorescences of it are used as an edible wild vegetable in Chinese folk 
(see Fig.2). The taste is very delicious as a soup or stir-frying with the tender burgeon 
and inflorescences of it. Now this plant is begin to cultivate in Yuanjiang county of 
Yunnnan, China (see Fig.3). But up to now, the chemical constituents of this plant 
                                                        
∗ This work was supported by the Natural Science Foundation of Yunnan Province of China (2005B0049M) 
To whom Correspondence shoud be addressed. Tel./Fax: 86 –871 – 5215967, E-mail: liuxikui@mail.kib.ac.cn 
 
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LETTERS TO NATURE 
have not been reported. Our investigation on this plant led to the isolation of two 
taxane (1 and 2) and L-iditol (3, the structures of them see Fig.4).  
Their structures were identified as Taxayunnansin B(1)8, Taxumairol E(2)9 and 
L-iditol(3)10 on the basis of NMR and MS spectrum with comparison of their spectral 
data previously, respectively.  
Taxayunnansin B(1), colorless needle crystal (CHCl3), C35H44O13, m.p. 318～
319℃. UV λMeOH max : 205, 229, 271nm; FAB+-MS (positive) m/z: 673 [M+H]+, 551, 491, 431, 373, 
329, 311, 253, 173, 105 (100). 1H NMR (500 MHz, CDCl3): δH 6.09(d, J =7.8Hz, 1H, 2-H), 3.12(d, 
J =7.8Hz, 1H, 3-H), 4.93 (d, J =7.8Hz, 1H, 5-H), 2.22, 1.60(m, 2×1H, 6-CH2), 4.48(d, J =7.8Hz, 
1H, 7-H), 6.13(d, J =11.8Hz, 1H, 9-H), 6.51(d, J =11.8 Hz, 1H, 10-H), 5.52(t, J = 8.2Hz, 1H, 
13-H), 2.50, 1.88 (m, 2×1H, 14-CH2), 1.05(s, 3H, 16-H), 1.66(s, 3H, 17-CH3), 1.72(s, 3H, 
18-CH3), 1.15(s, 3H, 19-CH3), 4.46, 4.38(d, J =7.6Hz, 2×1H, 20-CH2), 2.00, 2.00, 2.05, 2.14(s, 4
× 3H, 4 × CH3-acetyl], 7.82(d, J=7.6Hz, 2H, o-CH-benzoyl), 7.39(t, J=7.7Hz, 2H, 
m-CH-benzoyl), 7.52 (t, J=7.4 Hz, 1H, p-CH-benzoyl), 2.07(d, J=6.8Hz, 1H, 7-OH), 2.71(s, 1H, 
15-OH) ppm；13C NMR (125 MHz, CDCl3): δC 67.6(s, C-1), 69.1(d, C-2), 44.0(d, C-3), 79.8(s, 
C-4), 84.9(d, C-5), 34.7(t, C-6), 67.9(d, C-7), 43.6(s, C-8), 76.7 (d, C-9), 77.0(d, C-10), 133.8(s, 
C-11), 151.4(s, C-12), 70.3(d, C-13), 39.5(t, C-14), 74.9(s, C-15), 12.5(q, C-16), 25.2(q, C-17), 
27.4(q, C-18), 11.8(q, C-19), 75.4(t, C-20), 20.5, 21.3, 21.5, 22.3(q, 4×CH3-acetyl], 169.7, 169.7, 
170.3, 171.0(s, 4 × C=O-acetyl], 164.0(s,C=O-benzoyl), 129.0(s, C-benzoyl), 129.4(d, 
2′,6′-CH-benzoyl), 128.7(d, 3′,5′-CH-benzoyl), 133.3(d, 4′-CH-benzoyl) ppm. 
Taxumairol E(2), colorless sheet crystal (CH3COCH3), C30H44O12, m.p. 230～
232 ℃，[α]25D+ 54.9 (CHCl3, c 0.75). UV λMeOH max  (log ε) nm: 225 (3.60). IR νmax cm-1: 3468, 
2936, 1740, 1462, 1440, 1376, 1246, 1026, 992, 754. ESI-MS(positive) m/z: 619[M+Na]+, 559, 
537 (100), 477, 417. 1H NMR(400MHz, CD3OD): δH 2.00(m, 1H, 1-H), 4.28 (d, J =3.9Hz, 1H, 
2-H), 2.58(m, 1H, 3-H), 2.00(m, 1H, 4-H), 5.05(m, 1H, 5-H), 2.00, 1.70(m, 1H×2, 6-H), 5.37(dd, 
J =11.7, 5.1Hz, 1H, 7-H), 5.77 (d, J =11.0Hz, 1H, 9-H), 6.16(d, J =11.0Hz, 1H, 10-H), 5.94(dd, J 
=7.8, 8.4Hz, 1H, 13-H), 2.59, 1.60(m, 2×1H, 14-CH2), 1.68(s, 3H, 16-CH3), 1.16(s, 3H, 17-CH3), 
2.20(s, 3H, 18-CH3), 0.93(s, 3H, 19-CH3), 3.99(dd, J =10.5, 2.1Hz, 1H, 20α-H), 3.30 (m, 1H, 
20β-H), 2.11, 2.04, 2.02, 1.96, 2.21(s, 5×3H, 5×CH3-acetyl)ppm；13C NMR(100MHz, CD3OD): δC 
51.7(d, C-1), 71.3(d, C-2), 40.7(d, C-3), 46.8(d, C-4), 70.0(d, C-5), 30.0(t, C-6), 69.1(d, C-7), 45.7 
(s, C-8), 75.8(d, C-9), 71.7(d, C-10), 133.3(s, C-11), 137.6(s, C-12), 70.6(d, C-13), 27.6(t, C-14), 
37.8(s, C-15), 27.3(q, C-16), 31.8(q, C-17), 14.9(q, C-18), 14.2(q, C-19), 65.0(t, C-20), 21.4, 20.9, 
20.8, 21.5, 21.7(q, 5×CH3-acetyl], 169.7, 169.1, 170.0, 170.4, 170.4(s, 5×C=O-acetyl) ppm. 
L-iditol(3), C6H14O6，M=182. m.p.73-75oC. ESI m/z: 363[2M-1], 181[M-1], 
163[M-1-H2O].1H NMR(400MHz, D2O)：δH 3.66(dd, J=2.6, 11.6Hz, 2H, 1β, 6β-H), 
3.74(ddd, J=8.6, 6.0, 2.6Hz, 2H, 3,4-H), 3.78(d, J=8.6Hz, 2H, 2,5-H), 3.85(dd, J=2.6, 
11.6Hz, 2H, 1α, 6α-H)ppm. 13C NMR(400MHz, D2O)：δC 66.0(C-1,6). 72.0(C-3,4), 
73.5(C-2,5)ppm.  
The results presented here show that at least some, and perhaps all, of the L-iditol 
and taxane present in Yunnanopilia longistaminata. Yet, we have not ruled out that, in 
addition, the plant may produce its own Taxol, but it is a new source of L-iditol and 
taxane.  
 
METHODS SUMMARY 
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LETTERS TO NATURE 
The fresh tender burgeons of Yunnanopilia longistaminata was extracted 
exhaustively with 90% EtOH and fractionated by successive partition with EtOAc, 
then subjected to silica gel column chromatography with a CHCl3-MeOH and 
Lichroprep RP-18 gel column chromatography with MeOh-H2O to yield Taxayunnansin B(1)8, 
Taxumairol E(2). The H2O fraction was crystallized with 80% EtOH-H2O to provide 
L-iditol(3). 
 
Reference 
1. Mayumi O., Toyoaki S., Toru O., Yasuji S., Hiromi B.M., Microbial production of optically 
pure L-iditol by yeast strains, Appl.& Environ.Microbi., 46, 912-916(1983) 
2. Patrik F., Lomme (F.R.), Method for preparing L-iditol, United State Patent No. 
US20060096588A1(2006) 
3. A.Hoffman, W.Kham, J.Worapong, G.Strobel, D.Griffin, B.Arbogast, B.Barofsky, R.B.Boone, 
L.Ning, Z.Ping, L.Daley, Bioprospecting for taxol in angiosperm plant extracts, Spectroscopy, 
13(6):22-32(1998) 
4. Robert F.,Hazel Trees Offer New Source of Cancer Drug, Science, 288(5643). 27-28(2000) 
5.Andrea S., Gary S., Donald S., Taxol and taxane production by Taxomyces andreanae, an 
endophytic fungus of pacific yew, Science, 260(5105), 214-216(1993) 
6. Nicolaou K.C., Yang Z., Liu J.J., Ueno H., Nantermet P.G., Guy R.K., Clalborne C.F., Renaud J., 
Couladouros E.A., Paulvannan K., Sorensen E.J., Total synthesis of taxol, Nature, 367, 
630-634(1994) 
7. Wu Z.Y., Li D.Z., Yunnanopilia-A primitive new Genus of Opiloaceae from Yunnan plateau, 
China and its biogeographic significance, Acta Botanica Yunnanica, 22(3), 248-250(2000) 
8. Liu X.K., Wu D.G., Wang Z.Y., A New Diterpene Compounds From Taxus yunnanensis,Chinese 
Science Bulletin, 38(13), 2186-2189(1992)  
9. Shen Y.C., Chen C.Y., Taxanes from the roots of Taxus mairei, Phytochemistry, 
44(8):1527-1533(1997) 
10. Stephen J. Angyal, Ronan Le Fur, The 13C-NMR spectra of alditols, Carbohydrate Research, 
84, 201-209(1980) 
 
Acknowledgements: This work was supported by the Natural Science Foundation of Yunnan 
Province of China (2005B0049M). The spectrums data were mensurated by the Analytical Group 
of the Laboratory of Phytochemistry, Kunming Institute of Botany, Chinese Academy of Sciences.  
 
Author Contribution J.-J. Liu performed the isolation and identification the structure of 
Taxayunnansin B, Taxumairol E. X.-K. Liu collected the plant materials, isolated and identified 
the structure of L-iditol, supervised the project and wrote the manuscript.  
 
Author Information The plant material was authenticated by Prof. Chun-Chao Lv, and 
a voucher specimem (No.KIB 05-04-10) was deposited at the State Key Laboratory of 
Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese 
Academy of Sciences, P.R.China. Reprints and permissions information is available at 
www.nature.com/reprints. Correspondence and requests for material should be addressed to 
Xi-Kui Liu (liuxikui@mail.kib.ac.cn). 
 
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LETTERS TO NATURE 
METHODS 
Melting points were obtained on an X-4 Digital Melting apparatus and were uncorrected. 
Optical rotations were carried out on a Perkin-Elmer model 241 polarimeter. IR spectra were 
measured in a Bio-Rad FTS-135 spectrometer with KBr pellets. MS were recorded on a VG Auto 
spec-3000 spectrometer and a Finnigan MAT 90 instrument. NMR spectra were taken on a Bruker 
AM-400 and a Bruker DRX-500 instrument with TMS as an internal standard, respectively. 
Column chromatography were performed either on silica gel (200-300 mesh, Qingdao Marine 
Chemical Inc., China), silica gel H (10-40μm, Qingdao Marine Chemical Inc., China), or 
Lichroprep RP-18 gel (40-63μm, Merck, Dramstadt, Germany).  
The fresh tender burgeons of Yunnanopilia longistaminata was collected at April 2005, from 
Shiping, Yunnan Province, and was identified by Prof. Chun-Chao Lv of the Kunming Institute of 
Botany, Chinese Academy of Sciences. A voucher specimem (No.KIB 05-04-10) was deposited at 
the State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming 
Institute of Botany, Chinese Academy of Sciences, P.R.China.  
 The fresh tender burgeons of Yunnanopilia longistaminata (10kg) was cut into 
pieces with a knife and extracted exhaustively with 90% EtOH at room temperature. 
The EtOH extract was evaporated at 45  to ℃ yield a black syrup-like residue (570g) 
under reduces pressure. The residue was suspended in H2O and fractionated by 
successive partition with petroleum ether, EtOAc, and n-BuOH to give petroleum 
ether soluble (62g), EtOAc-soluble (141g) and n-BuOH-soluble fractions (127g), 
respectively. The EtOAc extract (141g) was subjected to silica gel column 
chromatography, eluted with a CHCl3-MeOH (10:0, 9:1, 8:2, 7:3, 6:4, 0:1v/v) 
gradiently to give four fractions according to TLC of silica gel H with 
CHCl3-MeOH(4:1). Fraction II (4.2g) was subjected to silica gel column 
chromatography with CHCl3-MeOH (4:1) and Lichroprep RP-18 gel column 
chromatography with MeOh-H2O (1:1) to yield Taxayunnansin B(2.0g) and Taxumairol 
E(10mg). The H2O fraction was concentrated under reduced pressure, and crystallized 
with 80% EtOH-H2O to provide compound 3(27g).  
 
 
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FIG. 1 The tree of Yunnanopilia longistaminata (W.Z.Li) C.Y.Wu et D.Z.Li. It is monotypie genus 
plant and mainly distributed along the Red River Valley and occurs at semitropical forests at altitudes 
of 900-1500 meters in Yunnan, China,   
 
 
FIG. 2 The twig and leaves of Yunnanopilia longistaminata (W.Z.Li) C.Y.Wu et D.Z.Li. The tender 
burgeon of it is used as an edible wild vegetable in Chinese folk. The taste is very delicious as a soup or 
stir-frying with the tender burgeon and inflorescences of it.  
 
FIG. 3 The young seedling of Yunnanopilia longistaminata (W.Z.Li) C.Y.Wu et D.Z.Li. It is cultivated 
with seed in the Yuanjiang county of Yunnan, China. 
 
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OAcO
AcO H
OAc
HO
AcO
BzO
OH
AcO
OAcOAc
OH
OAc
HOH
HH
AcO
CH2OH
C OHH
CHO H
C OHH
C HHO
CH2OH
1
3
4
7
9
11
13
18
19
20
1516
17
1 3
4
7
8
911
1513
16
17
18
19
20
1 2 3
 
 FIG. 2 Structures of taxayunnansin B(1), taxumairol E(2) and L-iditol(3). Abbreviations for 
chemical groups: OBz, benzoyl; OAc, acetyl. Selected physical dada for compound 1: 1H NMR (500 
MHz, CDCl3): δH 6.09(d, J =7.8Hz, 1H, 2-H), 3.12(d, J =7.8Hz, 1H, 3-H), 4.93 (d, J =7.8Hz, 1H, 5-H), 
2.22, 1.60(m, 2×1H, 6-CH2), 4.48(d, J =7.8Hz, 1H, 7-H), 6.13(d, J =11.8Hz, 1H, 9-H), 6.51(d, J =11.8 
Hz, 1H, 10-H), 5.52(t, J = 8.2Hz, 1H, 13-H), 2.50, 1.88 (m, 2×1H, 14-CH2), 1.05(s, 3H, 16-H), 1.66(s, 
3H, 17-CH3), 1.72(s, 3H, 18-CH3), 1.15(s, 3H, 19-CH3), 4.46, 4.38(d, J =7.6Hz, 2×1H, 20-CH2), 2.00, 
2.00, 2.05, 2.14(s, 4×3H, 4×CH3-acetyl], 7.82(d, J=7.6Hz, 2H, o-CH-benzoyl), 7.39(t, J=7.7Hz, 2H, 
m-CH-benzoyl), 7.52 (t, J=7.4 Hz, 1H, p-CH-benzoyl), 2.07(d, J=6.8Hz, 1H, 7-OH), 2.71(s, 1H, 
15-OH) ppm；13C NMR (125 MHz, CDCl3): δC 67.6(s, C-1), 69.1(d, C-2), 44.0(d, C-3), 79.8(s, C-4), 
84.9(d, C-5), 34.7(t, C-6), 67.9(d, C-7), 43.6(s, C-8), 76.7 (d, C-9), 77.0(d, C-10), 133.8(s, C-11), 
151.4(s, C-12), 70.3(d, C-13), 39.5(t, C-14), 74.9(s, C-15), 12.5(q, C-16), 25.2(q, C-17), 27.4(q, C-18), 
11.8(q, C-19), 75.4(t, C-20), 20.5, 21.3, 21.5, 22.3(q, 4×CH3-acetyl], 169.7, 169.7, 170.3, 171.0(s, 
4×C=O-acetyl], 164.0(s,C=O-benzoyl), 129.0(s, C-benzoyl), 129.4(d, 2′,6′-CH-benzoyl), 128.7(d, 
3′,5′-CH-benzoyl), 133.3(d, 4′-CH-benzoyl) ppm. UV λMeOH max : 205, 229, 271nm; FAB+-MS (positive) 
m/z: 673 [M+H]+, 551, 491, 431, 373, 329, 311, 253, 173, 105 (100). Compund 2: 1H NMR(400MHz, 
CD3OD): δH 2.00(m, 1H, 1-H), 4.28 (d, J =3.9Hz, 1H, 2-H), 2.58(m, 1H, 3-H), 2.00(m, 1H, 4-H), 
5.05(m, 1H, 5-H), 2.00, 1.70(m, 1H×2, 6-H), 5.37(dd, J =11.7, 5.1Hz, 1H, 7-H), 5.77 (d, J =11.0Hz, 1H, 
9-H), 6.16(d, J =11.0Hz, 1H, 10-H), 5.94(dd, J =7.8, 8.4Hz, 1H, 13-H), 2.59, 1.60(m, 2×1H, 14-CH2), 
1.68(s, 3H, 16-CH3), 1.16(s, 3H, 17-CH3), 2.20(s, 3H, 18-CH3), 0.93(s, 3H, 19-CH3), 3.99(dd, J =10.5, 
2.1Hz, 1H, 20α-H), 3.30 (m, 1H, 20β-H), 2.11, 2.04, 2.02, 1.96, 2.21(s, 5×3H, 5×CH3-acetyl)ppm；13C 
NMR(100MHz, CD3OD): δC 51.7(d, C-1), 71.3(d, C-2), 40.7(d, C-3), 46.8(d, C-4), 70.0(d, C-5), 30.0(t, 
C-6), 69.1(d, C-7), 45.7 (s, C-8), 75.8(d, C-9), 71.7(d, C-10), 133.3(s, C-11), 137.6(s, C-12), 70.6(d, 
C-13), 27.6(t, C-14), 37.8(s, C-15), 27.3(q, C-16), 31.8(q, C-17), 14.9(q, C-18), 14.2(q, C-19), 65.0(t, 
C-20), 21.4, 20.9, 20.8, 21.5, 21.7(q, 5×CH3-acetyl], 169.7, 169.1, 170.0, 170.4, 170.4(s, 5×C=O-acetyl) 
ppm. UV λMeOH max  (log ε) nm: 225 (3.60). IR νmax cm-1: 3468, 2936, 1740, 1462, 1440, 1376, 1246, 1026, 
992, 754. ESI-MS(positive) m/z: 619[M+Na]+, 559, 537 (100), 477, 417. Compound 3: 1H 
NMR(400MHz, D2O)：δH 3.66(dd, J=2.6, 11.6Hz, 2H, 1β, 6β-H), 3.74(ddd, J=8.6, 6.0, 2.6Hz, 2H, 
3,4-H), 3.78(d, J=8.6Hz, 2H, 2,5-H), 3.85(dd, J=2.6, 11.6Hz, 2H, 1α, 6α-H)ppm. 13C NMR(400MHz, 
D2O)：δC 66.0(C-1,6). 72.0(C-3,4), 73.5(C-2,5)ppm. ESI m/z: 363[2M-1], 181[M-1], 163[M-1-H2O]. 
 
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Microbial production of optically pure L-iditol by yeast strains,

New source for L-iditol and taxanes

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New source for L-iditol and taxanes

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