全 文 ：Received 24 Nov. 2003 Accepted 24 Feb. 2004
Supported by the National Natural Science Foundation of Ch ina (30370118) and the Provincial Natural Science Fund of Yunnan of China
(2001B055M).
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Acta Botanica Sinica
植 物 学 报 2004, 46 (5): 625-630
Cyclopeptides from Three Arctic Caryophyllaceae Plants, Chemotaxonomy
and Distribution Significance of Caryophyllaceae Cyclopeptides
JIA Ai-Qun1, TAN Ning-Hua1, YANG Yong-Ping2, WU Su-Gong2, WANG Li-Qin1, ZHOU Jun1*
(1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany,
The Chinese Academy of Sciences, Kunming 650204, China;
2. Laboratory of Plant Biodiversity and Biogeography, Kunming Institute of Botany,
The Chinese Academy of Sciences, Kunming 650204, China)
Abstract : Five new cyclopeptides named arcticumin A (1 ), arcticumin B (2 ), arcticumin C (3 ), regelin A
(4 ) and crassipin B (5 ) were isolated from three arctic Caryophyllaceae species (＜100 g), Cerastium
arcticum Lange, C. regelii Ostenf. and Stellaria crassipes Hult., with structures elucidated primarily by
FAB+-MS and amino acids analysis. Based on the comparison of Caryophyllaceae cyclopeptides from both
the Qinghai-Xizang (Tibet) Plateau and Arctic region, it is proposed that cyclopeptides are characteristic
components of Caryophyllaceae and Arctic region is one part of the distribution center of Caryophyllaceae.
Key words: Stellaria crassipes ; Cerastium arcticum ; Cerastium regelii ; Caryophyllaceae; cyclopeptides;
Arctic region; chemotaxonomy; distribution
The Caryophyllaceae is an important plant family, con-
taining 60 genera and over 2 000 species in the world . In
most taxonomic literatures, Caryophyllaceae is usually di-
vided into three subfamilies, namely Paronychoideae,
Alsinoideae, and Caryophylloideae (Lu et a l., 2003).
Biogeographically, Caryophyllaceae is almost d istributed
all over the world, some species of which are found in Arc-
tic region or Antarctic (Lu et al., 1996) though most species
are distributed in the north temperate region, especially the
Mediterranean and East Asia. Meanwhile, some species of
the family, such as Pseudostellaria heterophylla, Dian-
thus chinensis, Psammosilene tun ico ides, Vaccaria
segetalis, have been traditionally used as herb medicine in
China (Tang et al., 1996).
By now, chemical studies o f more than 150 species of
Caryophyllaceae have been conducted. The components
investigated include cyclopeptides, saponins, ecdysteroids,
flavonoids, alkalo ids, diterpenoids, amino acids, etc. Tan
(Zhou et al., 2004) thought that cyclopeptides , saponins,
ecdysteroids and flavonoids are present widely as charac-
teristic components of Caryophyllaceae, and five-ringed
triterpenoid saponins and cyclopeptides have distinct dis-
tribution significance of Caryophyllaceae based on the sta-
tistical research of these two types of compounds, i.e. five-
rin ged t rit erpe no id s ap on in s ar e p r es en ted in
Paronycho ideae and Caryophyl lo ideae , rar e in
Alsino ideae; to be more interes ting, cyclopep tides are
present in all three Caryophyllaceae subfamilies, rich in
Alsinoideae. Hence, cyclopeptides may be considered as
characteristic components, which are more important than
other characterist ic components such as five-ringed
triterpenoid saponins in this family.
Cyclopeptides are cyclic compounds formed mainly with
the peptide bonds of protein or nonprotein amino acids.
Bas ed on the skeletal s tructure, it was proposed on the
systematic classification that cyclopeptides could be di-
vided into two classes and six subclasses. The classifica-
tion is shown as Fig.1 (Tan et al., 1997).
Stellaria crassipes, Cerastium arcticum and C. regelii
are three species distributed in Arctic region, and they be-
long to Alsineae tribe of Alsino ideae. The chemical stud-
ies of Stellaria and Cerastium are focused on cyclopeptides
and flavonoids (Dubois et al., 1982a; 1982b; 1984; Zhao et
al., 1995; 1997; Morita et al., 1996; 1997a; 1997b). Chemical
investigations on these three species have not been re-
ported till now.
In this paper, we mainly present the chemical study of
cyclopep t ides from th ree t race s amples o f arct ic
Caryophyllaceae species Stellaria crassipes, Cerastium
arcticum and C. regelii. The chemotaxonomy and distribu-
tion significance of Caryophyllacea cyclopeptides are also
discussed.


JIA Ai-Qun et al.: Cyclopeptides from Three Arctic Caryophyllaceae Plants, Chemotaxonomy and Distribution Significance
of Caryophyllaceae Cyclopeptides 629
0.000 522%), arct icumin B (2) (0.38 mg, 0.000 389%),
arcticumin C (3) (0.46 mg, 0.000 471%), regelin A (4) (0.16
mg, 0.000 433%), respectively.
2.4 Data of cyclopeptides 1-5
Arcticumin A (1) C36H55 N7O7. Amino acid analysis:
Phe (1 eq.), Ile (3eq.), Gly (2 eq.) and Pro (1 eq.). Pos. FAB+-
MS m/z: 697 [M]+, 550, 436, 324, 267, 154, 97.
Arcticumin B (2) C33H53N9O16. Amino acid analysis
of the hydrolysate: Asp (1eq.), Thr (1 eq.), Ser (2 eq.), Glu (1
eq .), Gly (2 eq.) and Val (2 eq.). Pos. FAB+-MS m/z: 831
[M]+, 774, 730, 659, 631, 544, 445, 416, 388, 273, 186.
Arcticumin C (3) C37H51N9O14. Amino acid analysis
of the hydrolysate: Asp (1 eq.), Thr (1eq.), Ser (2 eq.), Gly (2
eq.), Phe (1 eq.) and Pro (2 eq.). Pos. FAB+-MS m/z: 845
[M]+, 730, 661, 633, 486, 417, 389, 288, 231, 172, 144.
Regelin A (4) C45H68N10O13. Amino acid analysis of
the hydrolys ate: Ser (1 eq.), Glu (1eq.), Gly (3 eq.), Val (1
eq.), Leu (2 eq.), Phe (1 eq.) and Pro (1 eq.). Pos. FAB+-MS
m/z: 956 [M]+, 809, 723, 695, 598, 513, 485, 398, 369, 341, 228,
99.
Crassipin B (5) C33H43N7O8. Amino acid analysis of
the hydrolysate: Gly (3 eq.), A la (1eq.), Leu (1 eq.), Tyr (1
eq.) and Phe (1 eq.). Pos. FAB+-MS m/z: 665 [M]+, 594, 552,
523, 495, 348, 262, 234, 184.
Acknowledgements: The authors are grateful to the mem-
bers of the analytical group in the State Key Laboratory of
Phytochemistry and Plant Resources in West China, The
Chinese Academy of Sciences for spectral measurements,
to Prof. WU Zheng-Yi for his helpful advice.
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