Chemistry, bioactivity and quality control of Dendrobium, a commonly used tonic herb in traditional Chinese medicine

Abstract

The fresh or dried stems of many Dendrobium species are well known as one of the most expensive tonics in traditional Chinese medicine. Documented as a “superior grade” herbal medicine in the ancient text “Shen Nong’s Herbal Classic”, Dendrobium has been used for thousands of years and is now a popular health food worldwide. The main chemical components of Dendrobium are alkaloids, aromatic compounds, sesquiterpenoids and polysaccharides, with multiple biological activities, including immunomodulatory, neuroprotective and anti-tumor effects, etc. Various qualitative and quantitative methods have been developed for the quality evaluation of Dendrobium. In this review, the research progress since the 1930s relating to the chemistry, bioactivity and quality control of Dendrobium is summarized, existing problems and prospects are also discussed.

Full text

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Phytochemistry Reviews
Fundamentals and Perspectives of
Natural Products Research
ISSN 1568-7767
Volume 12
Number 2
Phytochem Rev (2013) 12:341-367
DOI 10.1007/s11101-013-9310-8
Chemistry, bioactivity and quality control
of Dendrobium, a commonly used tonic
herb in traditional Chinese medicine
Jun Xu, Quan-Bin Han, Song-Lin Li,
Xiao-Jia Chen, Xiao-Ning Wang, Zhong-
Zhen Zhao & Hu-Biao Chen

1 23
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Chemistry, bioactivity and quality control of Dendrobium,
a commonly used tonic herb in traditional Chinese medicine
Jun Xu •Quan-Bin Han •Song-Lin Li •
Xiao-Jia Chen •Xiao-Ning Wang •
Zhong-Zhen Zhao •Hu-Biao Chen
Received: 4 August 2012 / Accepted: 21 June 2013 / Published online: 4 July 2013
ÓSpringer Science+Business Media Dordrecht 2013
Abstract The fresh or dried stems of many Dendr-
obium species are well known as one of the most
expensive tonics in traditional Chinese medicine.
Documented as a ‘‘superior grade’’ herbal medicine
in the ancient text ‘‘Shen Nong’s Herbal Classic’’ ,
Dendrobium has been used for thousands of years and
is now a popular health food worldwide. The main
chemical components of Dendrobium are alkaloids,
aromatic compounds, sesquiterpenoids and polysac-
charides, with multiple biological activities, including
immunomodulatory, neuroprotective and anti-tumor
effects, etc. Various qualitative and quantitative
methods have been developed for the quality evalu-
ation of Dendrobium. In this review, the research
progress since the 1930s relating to the chemistry,
bioactivity and quality control of Dendrobium is
summarized, existing problems and prospects are also
discussed.
Keywords Dendrobium Chemistry Bioactivity 
Quality control
Introduction
Dendrobium, one of the largest genera in Orchidaceae,
having more than 1,100 species identified, is widely
distributed throughout Asia, Europe and Australia
(Zhang et al. 2003a). In China, the fresh or dried stems
of many Dendrobium species are collectively regarded
as a famous herbal medicine. Listed as a ‘‘superior
grade’’ medicinal herb in ‘‘Shen Nong’s Herbal
Classic,’’ which is one of the earliest herbal pharma-
copeia in the world, Dendrobium has been used in
Chinese medicine for thousands of years for its
traditional properties of supplementing the stomach,
promoting the production of body fluids, nourishing
Yin, and clearing heat (Deng et al. 2002).
Despite 78 species of Dendrobium found in China,
thirty of which are currently used under the same
Chinese name Shihu, Chinese Pharmacopoeia (2010
edition) has only two monographs of medicinal
Dendrobium plants. One is Dendrobii Caulis (Shihu in
Chinese), derived from Dendrobium nobile,D. chrys-
otoxum,D. fimbriatum and other related Dendrobium
species. The other is Dendrobii Officinalis Caulis (Tiepi
shihu in Chinese), derived from D. officinale (Fig. 1).
J. Xu Q.-B. Han Z.-Z. Zhao H.-B. Chen (&)
School of Chinese Medicine, Hong Kong Baptist
University, Hong Kong SAR, China
e-mail: hbchen@hkbu.edu.hk
S.-L. Li (&)X.-N. Wang
Department of Pharmaceutical Analysis and
Metabolomics, Jiangsu Province Academy of Traditional
Chinese Medicine, No. 100, Shizi Street, Hongshan Road,
Nanjing 210028, China
e-mail: songlinli64@126.com
X.-J. Chen
State Key Laboratory of Quality Research in Chinese
Medicine, Institute of Chinese Medical Sciences,
University of Macau, Macao, China
123
Phytochem Rev (2013) 12:341–367
DOI 10.1007/s11101-013-9310-8
Author's personal copy

Chemical studies on Dendrobium plants have been
conducted since the 1930s. While alkaloids, aromatic
compounds, sesquiterpenoids and polysaccharides
have been identified as the main components (Chen
and Guo 2001), the chemical profile varies greatly
among species and samples collections (Xu et al.
2010b,2011; Yang et al. 2006c) which in turn makes
these Dendrobium species possess diverse bioactivi-
ties: Dendrobium polysaccharides exhibit immuno-
modulatory, antioxidant and hepatoprotective activity;
the alkaloids are anti-cataract and neuroprotective,
and the aromatic compounds and sesquiterpenoids
exert anti-angiogenesis, anti-tumor and anti-mutagen-
esis effects (Ng et al. 2012).
Therefore, quality control becomes urgent for
ensuring the efficacy and safety of Dendrobium in
clinical applications. Chinese Pharmacopoeia (2010
edition) recommended only one chemical marker
which seems powerless for so many Dendrobium
species involved. Furthermore, there are multiple
factors affecting the quality, not only species, but also
geographic localities, harvest times and processing
methods (Xu et al. 2010b). To date, many studies have
attempted to develop accurate, sensitive and selective
analytical methods for qualitative and quantitative
evaluation of Dendrobium materials.
In this paper, the progress in researches of chem-
istry, bioactivity and quality control of Dendrobium
plants is reviewed with some existing problems
addressed and suggestions for further study are also
proposed.
Chemistry
In the past 80 years, more than forty Dendrobium
species have been investigated for their phytochem-
istry, with a focus on small molecules, such as
alkaloids, aromatic compounds and sesquiterpenoids,
while researches on biomacromolecules in Dendrobi-
um species started 30 years ago. The results showed
that different Dendrobium sources presented unique
chemical profiles.
Alkaloids
Alkaloids are the first category of compounds
extracted from Dendrobium with confirmed chemical
structures. So far, five types of alkaloids with different
structural skeletons have been reported from Dendr-
obium, namely sesquiterpenoids, indolizidine, pyrrol-
idines, phthalides and imidazoles (Table 1). As shown
in Fig. 2a and Table 1, a sesquiterpenoid, also cate-
gorized as the dendrobine-type, has been found in six
Dendrobium species. Its basic skeleton consists of one
picrotoxane-type sesquiterpenoid combined with a
Fig. 1 The original plants of D. nobile (a), D. chrysotoxum (b), D. fimbriatum (c) and D. officinale (d)
342 Phytochem Rev (2013) 12:341–367
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Table 1 Micromolecular compounds in Dendrobium spp.
Dendrobium species Components Refs.
D. aduncum Fluorenones: chrysotoxone (A1
a
); dengibsin (A1); dengibsinin (A1)
Sesquiterpenoids: aduncin (A1)
Other kinds of compounds: monoaromatics; steroids
Bi et al. (2006), Gawell and
Leander (1976)
D. amoenum Bibenzyls: moscatilin (A); chrysotobibenzyl (A); batatasin III (A); 3,40-dihydroxy-5-
methoxybibenzyl (A); amoenylin (A); isoamoenylin (A); gastrochilinin (B1);
gastrochilin (B1)
Phenanthrenes: confusarin (A1); 2,7-dihydroxy-3,4,6-trimethoxyphenanthrene (A1);
imbricatin (A2); amoenumin (A2)
Sesquiterpenoids: amotin (A1); amoenin (A1)
Majumder et al. (1999),
Majumder and
Bandyopadhyay (2010),
Veerraju et al. (1989),
Dahme
´n and Leander (1978)
D. amplum Bibenzyls: gigantol (A); batatasin III (A)
Phenanthrenes: 2,7-dihydroxy-3,4,6-trimethoxyphenanthrene (A1); 2,3,7-trihydroxy-
4,6-dimethoxyphenanthrene (A1); 2,3,7-trihydroxy-4,6-dimethoxy-9,10-
dihydrophenanthrene (A2); 2,7-Dihydroxy-3,4,6-trimethoxy-9,10-
dihydrophenanthrene (A2); coelonin (A2); amplumthrin (A2); flavanthrin (A2)
Majumder et al. (2008)
D. anosmum Alkaloids: dendroparine (E) Leander and Lu
¨ning (1968)
D. aphyllum Bibenzyls: moscatilin (A); gigantol (A); batatasin III (A); tristin (A); 3,40,5-
trihydroxybibenzyl (A); 4,40-dihydroxy-3,5-dimethoxybibenzy (A)
Phenanthrenes: moscatin (A1); 2,4,7-trihydroxy-9,10-dihydrophenanthrene (A2);
lhridinusiant (A2); coelonin (A2); flavanthrin (A2)
Other kinds of compounds: monoaromatics; flavonoids; lignans
Chen et al. (2008a), Shao et al.
(2008), Zhang et al. (2008a)
D. aurantiacum var. denneanum Bibenzyls: moscatilin (A); gigantol (A); chrysotobibenzyl (A); chrysotoxine (A);
crepidatin (A)
Phenanthrenes: moscatin (A1); confusarin (A1)
Fluorenones: dendroflorin (A1); dengibsin (A1)
Coumarins: coumarin (B)
Other kinds of compounds: monoaromatics; steroids; flavonoids; terpenes
Chang et al. (2001), Yang et al.
(2006b), Ying et al. (2009),
Ma et al. (1998a), Zheng
et al. (2000a), Zhang et al.
(2005a), Yang et al. (2007c)
D. cariniferum Bibenzyls: gigantol (A); batatasin III (A); 3,30,5-trihydroxybibenzyl (A)
Phenanthrenes: dendronone (C2)
Other kinds of compounds: steroids
Liu et al. (2009), Chen et al.
(2008c)
Phytochem Rev (2013) 12:341–367 343
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Table 1 continued
Dendrobium species Components Refs.
D. chrysanthum Alkaloids: cis- and trans-dendrochrysine (C); cis- and trans-dendrochrysanines (C);
hygrine (C)
Bibenzyls: moscatiline (A); gigantol (A); chrysotobibenzyl (A); chrysotoxine (A);
crepidatin (A)
Phenanthrenes: moscatin (A1); 2,5-dihydroxy-4,9-dimethoxyphenanthrene (A1);
denthyrsinin (A1); denchryside A (A1); dendrochrysanene (B3); cypripedin (C1)
Fluorenones: dendroflorin (A1); denchrysan A (A1); dengibsin (A1); 3,5-dihydroxy-
2,4-dimethoxy-9H-fluoren-9-one (A1); 3,5-dihydroxy-4-methoxy-9H-fluoren-9-one
(A1); denchrysan B (A2)
Other kinds of compounds: lignans; monoaromatics; anthraquinones; steroids
Ekevag et al. (1973), Yang
et al. (2004d,2005b,2006a),
Luning and Leander (1965),
Ye et al. (2003,2004a,b),
Barlocco (2006)
D. chrysotoxum Bibenzyls: gigantol (A); chrysotobibenzyl (A); chrysotoxine (A); batatasin III (A);
erianin (A); trigonopol B (B3)
Phenanthrenes: moscatin (A1); confusarin (A1); chrysotoxene (A1); 2,5-dihydroxy-4,9-
dimethoxyphenanthrene (A1); 2,6-dihydroxy-5,7-dimethoxyphenanthrene (A1); 2,7-
dihydroxy-3,4,6-trimethoxyphenanthrene (A1); nudol (A1); fimbriatone (A1); 2,4,7-
trihydroxy-9,10-dihydrophenanthrene (A2); erianthridin (A2); chrysotoxol A (B2);
chrysotoxol B (B4); densiflorol B (C1)
Fluorenones: dendroflorin (A1); chrysotoxone (A1); denchrysan A (A1); dengibsin
(A1); 1,4,5-trihydroxy-7-methoxy-9H-fluoren-9-one (A1); 2,4,7-trihydroxy-1,5-
dimethoxy-9H-fluoren-9-one (A1); denchrysan B (A2)
Other kinds of compounds: monoaromatics; steroids; lignans; flavonoids
Li et al. (2009f,2011), Yang
et al. (2001,2002,2004a,b),
Ma et al. (1994b,1996,
1998b), Hu (2007), Chen
et al. (2008b), Gong et al.
(2006)
D. crepidatum Alkaloids: crepidine (B1); crepidamine (B2); isocrepidamine (B2); 1-((5S,6R, 7S,
8aR)-6-hydroxy-7-methyl-6-phenyl-octahydroindolizin-5-yl) propan-2-one (B2);
dendrocrepine (B2); isodendrocrepine (B2)
Bibenzyls: moscatilin (A); crepidatin (A)
Other kinds of compounds: monoaromatics; steroids; flavonoids; terpenes
Elander et al. (1973), Hu
(2007), Zhao et al. (2011),
Majumder and Chatterjee
(1989)
D. crystallinum Bibenzyls: gigantol (A); batatasin III (A); 3-O-methylgigantol (A); 3,30-dihydroxy-5-
methoxybibenzyl (A); 3,40-dihydroxy-5-methoxybibenzyl (A); 4,40-dihydroxy-3,5-
dimethoxybibenzy (A); 3,50-dihydroxy-30,4-dimethoxybibenzy (A); 40-hydroxy-
3,30,5-trimethoxybibenzyl (A); dencryol A (B4); dencryol B (B4)
Phenanthrenes: crystalltone (A1)
Sesquiterpenoids: dendronobilin B (A1); crystallinin (A2)
Other kinds of compounds: monoaromatics; flavonoids; steroids; lignans; terpenes;
nucleosides
Li et al. (2007), Wang et al.
(2008,2009b,2011b)
D. cumulatum Bibenzyls: tristin (A); cumulatin (A) Majumder and Pal (1993)
344 Phytochem Rev (2013) 12:341–367
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Table 1 continued
Dendrobium species Components Refs.
D. densiflorum Bibenzyls: moscatilin (A); gigantol (A); tristin (A); densiflorol A (B2)
Phenanthrenes: moscatin (A1); denthyrsinin (A1); lhridinusiant (A2); densiflorol B
(C1); cypripedin (C1)
Fluorenones: dendroflorin (A1); dengibsin (A1)
Coumarins: scoparone (B); scopoletin (B); scopolin (B); ayapin (C1); dihydroayapin
(C2)
Sesquiterpenoids: dendrodensiflorol (A1)
Other kinds of compounds: flavonoids; monoaromatics
Fan et al. (2000,2001), Zheng
et al. (2000b), Tang et al.
(2004), Dahmen et al. (1975)
D. draconis Bibenzyls: gigantol (A); batatasin III (A)
Phenanthrenes: 2,5,7-trihydroxy-4-methoxy-9,10-dihydrophenanthrene (A2); hircinol
(A2); 5-methoxy-7-hydroxy-9,10-dihydro-1,4-phenanthrenequinone (C2)
Sritularak et al. (2011a)
D. falconeri Bibenzyls: dendrofalconerol B (B3)
Other kinds of compounds: monoaromatics
Sritularak and
Likhitwitayawuid (2009)
D. farmerii Fluorenones: dengibsin (A1)
Coumarins: scoparone (B)
Majumder and Chakraborti
(1989)
D. fimbriatum Bibenzyls: moscatilin (A); chrysotobibenzyl (A); chrysotoxine (A); crepidatin (A)
Phenanthrenes: confusarin (A1); fimbriatone (A1)
Coumarins: scoparone (B); ayapin (C1)
Sesquiterpenoids: denhydroshizukanolide (C3)
Other kinds of compounds: monoaromatics; anthraquinones; steroids
Bi et al. (2001a,b,2003),
Majumder and
Bandyopadhyay (2010), Qing
et al. (2009), Talapatra et al.
(1992)
D. findlayanum Alkaloids: dendrobine (A1); 10-hydroxydendrobine (A1); nobiline (A4)
Sesquiterpenoids: crystallinin (A2); findlayanin (A4)
Granelli et al. (1970), Qin et al.
(2011)
D. friedricksianum Alkaloids: dendramine (A1); N-isopentenyldendroxinium (A1); N-isopentenyl-6-
hydroxydendroxinium (A1); nobiline (A4); 6-hydroxy-nobiline (A4)
Hedman et al. (1971)
D. fuscescens Other kinds of compounds: monoaromatics Talapatra et al. (1989)
D. gibsonii Fluorenones: dengibsin (A1); dengibsinin (A1) Talapatra et al. (1985)
D. gratiosissimum Bibenzyls: moscatilin (A); gigantol (A); batatasin III (A); tristin (A); erianin (A); 3,40,5-
trihydroxybibenzyl (A); 3,40-dihydroxy-5-methoxybibenzyl (A); 3,4-dihydroxy-40,5-
dimethoxy bibenzyl (A); isomoniliformine A (A); dengraols A (B5); dengraols B (B5)
Other kinds of compounds: monoaromatics; steroids; flavonoids
Zhang et al. (2007a,2008b),
Wang et al. 2007)
D. hilderbrandii Alkaloids: dendramine (A1); N-isopentenyldendroxinium (A1); N-isopentenyl-6-
hydroxydendroxinium (A1); nobiline (A4); 6-hydroxy-nobiline (A4)
Elander and Leander (1971),
Hedman et al. (1971)
D. huoshanense Other kinds of compounds: flavonoids; monoaromatics Chang et al. (2010)
Phytochem Rev (2013) 12:341–367 345
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Table 1 continued
Dendrobium species Components Refs.
D. loddigessi Alkaloids: shihunidine (C); shihunine (D1)
Bibenzyls: moscatilin (A); gigantol (A); batatasin III (A); loddigesiinol C (A);
loddigesiinol D (A)
Phenanthrenes: moscatin (A1); 5-hydroxy-2,4-dimethoxyphenanthrene (A1);
loddigesiinol A (A1); plicatol C (A2); lhridinusiant (A2); hircinol (A2); loddigesiinol
B (B1)
Other kinds of compounds: steroids; lignans
Li et al. (1991), Ito et al. (2010)
D. lohohense Alkaloids: shihunine (D1) Inubushi et al. (1964)
D. longicornu Bibenzyls: moscatilin (A); gigantol (A); batatasin III (A); aloifol I (A); tristin (A);
3,30,4-trihydroxybibenzyl (A); longicornuol B (A); 3,40-dihydroxy-30,4,5-
trimethoxybibenzyl (A); 3,30-Dihydroxy-4,5-dimethoxybibenzyl (A); cannabistilbene
II (A); longicornuol A (B4); trigonopol A (B4)
Phenanthrenes: 2,5,7-trihydroxy-4-methoxy-9,10-dihydrophenanthrene (A2); coelonin
(A2); hircinol (A2); dendronone (C2); ephemeranthoquinone (C2)
Other kinds of compounds: monoaromatics; steroids; flavonoids
Hu et al. (2008a,2010), Chen
et al. (2010), Hu (2007)
D. moniliforme Alkaloids: monoline (A3)
Bibenzyls: moscatilin (A); 3,40-dihydroxy-5-methoxybibenzyl (A); 3,40-dihydroxy-30,5-
dimethoxybibenzyl (A); 3,4-dihydroxy-40,5-dimethoxy bibenzyl (A);
dendromoniliside E (A)
Phenanthrenes: 2,4,7-trihydroxy-9,10-dihydrophenanthrene (A2); 7-hydroxy-5,6-
dimethoxy-1,4-phenanthrenequinone (C1); denbinobin (C1); moniliquinone (C3)
Sesquiterpenoids: dendromoniliside B (A1); dendromoniliside D (A1); dendroside F
(A1); dendrobiumane B (A1); dendrobiumane D (A1); dendromoniliside C (A1); a-
dihydropicrotoxinin (A1); picrotin (A1); dendrobiumane E (A1);dendrobiumane C
(A2); dendromoniliside A (A6); dendrobiumane A (B); 10b,13,14-
trihydroxyalloaromadendrane (B); dendroside A (B); dendroside C(B)
Other kinds of compounds: monoaromatics; lignans; steroids
Liu et al. (2007b), Zhao et al.
(2003a,b), Bi et al. (2002,
2004), Zhao and Zhao
(2003), Bae et al. (2004), Lin
et al. (2000,2001)
D. moscatum Bibenzyls: moscatilin (A)
Phenanthrenes: moscatin (A1)
Majumder and Sen (1987a,b)
346 Phytochem Rev (2013) 12:341–367
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Table 1 continued
Dendrobium species Components Refs.
D. nobile Alkaloids: dendrobine (A1); dendramine (A1); dendrine (A1); dendronobiline A (A1);
3-hydroxy-2-oxodendrobine (A1); dendroxine (A1); 6-hydroxy-dendroxine (A1);
8-hydroxy-dendroxine (A1); N-methyldendrobinium (A1); N-
isopentenyldendrobinium (A1); dendrobine N-oxide (A1); N-
isopentenyldendroxinium (A1); N-isopentenyl-6-hydroxydendroxinium (A1); nobiline
(A4)
Bibenzyls: moscatilin (A); gigantol (A); chrysotobibenzyl (A); chrysotoxine (A);
crepidatin (A); batatasin III (A); tristin (A); 3-O-methylgigantol (A); dendrobin A
(A); 4-hydroxy-3,30,5-trimethoxybibenzyl (A); nobilin A (A); nobilin B (A); nobilin C
(A); nobilin D (A); dendronophenol A (A); dendronophenol B (A); nobilin E (B3)
Phenanthrenes: moscatin (A1); confusarin (A1); 2,5-dihydroxy-4,9-
dimethoxyphenanthrene (A1); 2,6-dihydroxy-5,7-dimethoxyphenanthrene (A1); 2,5-
dihydroxy-3,4,8-trimethoxyphenanthrene (A1); 2,8-dihydroxy-3,4,7-
trimethoxyphenanthrene (A1); 2,3,5-trihydroxy-4,9-dimethoxyphenanthrene (A1);
3-hydroxy-2,4,7-trimethoxyphenanthrene (A1); 2,5-dihydroxy-3,4-
dimethoxyphenanthrene (A1); flavanthrinin (A1); nudol (A1); bulbophyllanthrin
(A1); fimbriol B (A1); plicatol A (A1); fimbriatone (A1); 4,5-dihydroxy-3,7-
dimethoxy-9,10-dihydrophenanthrene (A2); 3-hydroxy-2,4,7-trimethoxy-9,10-
dihydrophenanthrene (A2); 2,8-dihydroxy-3,4,7-trimethoxy-9,10-
dihydrophenanthrene (A2); 2-hydroxy-4,7-dimethoxy-9,10-dihydrophenanthrene
(A2); 2-hydroxy-3,4,7-trimethoxy-9,10-dihydrophenanthrene (A2); 4,5-dihydroxy-2-
methoxy-9,10-dihydrophenanthrene (A2); lhridinusiant (A2); coelonin (A2);
erianthridin (A2); ephemeranthol A (A2); ephemeranthol C (A2); hircinol (A2);
flavanthridin (A2); 2,20-dihydroxy-3,30,4,40,7,70-hexamethoxy-9,90,10,100-tetrahydro-
1,10-biphenanthrene (A2); denbinobin (C1)
Fluorenones: dendroflorin (A1); denchrysan A (A1); dengibsin (A1); nobilone (A1)
Sesquiterpenoids: dendronobilin B (A1); dendronobilin J (A1); dendronobilin L (A1);
dendrodensiflorol (A1); dendroside F (A1); dendroside G (A1); dendronobilin C (A1);
dendronobilin D (A1); dendronobilin E (A1); dendronobilin F (A1); dendronobilin M
(A1); nobilomethylene (A1); 7,12-dihydroxy-5-hydroxymethyl-11-isopropyl-6-
methyl-9-oxatricyclo[6.2.1.0
2,6
]undecan-10-one-15-O-b-D-glucopyranoside (A1);
dendronobiloside A (A5); dendronobiloside B (A5); 6a,10,12-trihydroxypicrotoxane
(A5); 10,12-dihydroxypicrotoxane (A5); bullatantriol (A5); dendronobilin A (A6);
dendronobilin K (A6); dendronobilin H(B); dendrobiumane A (B); 10b,13,14-
trihydroxyalloaromadendrane (B); 10b,12,14-trihydroxyalloaromadendrane (B);
dendroside A (B); dendroside B(B); dendroside D (B); dendronobilin G (C2);
dendroside E (C4); dendronobiloside C (C5); dendronobiloside D (C5); dendronobilin
I (C6); dendronobilin N (C6); dendronobiloside E (C6); dendrobane A (C6)
Other kinds of compounds: monoaromatics; lignans; anthraquinones; terpenes;
flavonoids
Inubushi et al. (1965), Suzuki
and Keimatsu (1932), Wang
et al. (1985), Yamamura and
Hirata (1964), Okamoto et al.
(1966a), Inubushi and
Nakano (1965), Liu and Zhao
(2003), Okamoto et al.
(1966b,1972), Hedman and
Leander (1972), Hwang et al.
(2010), Liu et al. (2007a),
Miyazawa et al. (1997,1999),
Li et al. (2010c), Ye and
Zhao (2002), Zhang et al.
(2006c,d,2007c,d,e,2008c,
d,e), Yang et al. (2007a), Lee
et al. (1995), Yang and Xin
(2006), Ye et al. (2002), Zhao
et al. (2001), Shu et al.
(2004a,b), Luo et al. (2006),
Xu et al. (2008)
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Table 1 continued
Dendrobium species Components Refs.
D. ochreatum Other kinds of compounds: steroids Behr et al. (1975), Behr and
Leander 1976)
D. officinale Bibenzyls: gigantol (A); 3-O-methylgigantol (A); 3,40,5-trihydroxybibenzyl (A); 3,40-
dihydroxy-5-methoxybibenzyl (A); 4,40-dihydroxy-3,5-dimethoxybibenzy (A); 3,4-
dihydroxy-40,5-dimethoxy bibenzyl (A); dendrophenol (A); dendromoniliside E (A);
dendrocandin A (A); dendrocandin C (A); dendrocandin D (A); dendrocandin E (A);
dendrocandin M (A); dendrocandin F (B3); dendrocandin G (B3); dendrocandin J
(B3); dendrocandin K (B3); dendrocandin N (B6); dendrocandin O (B6);
dendrocandin P (B6); dendrocandin Q (B6); dendrocandin B (B6); dendrocandin I
(B6); dendrocandin R (B7)
Phenanthrenes: confusarin (A1); 2,5-dihydroxy-3,4-dimethoxyphenanthrene (A1);
2,3,4,7-tetramethoxyphenanthrene (A1); nudol (A1); bulbophyllanthrin (A1); 2,4,7-
trihydroxy-9,10-dihydrophenanthrene (A2); denbinobin (C1); dendrocandin H (C4);
dendrocandin L (C4)
Sesquiterpenoids: aduncin (A1)
Other kinds of compounds: monoaromatics; lignans; flavonoids; terpenes; steroids
Guan et al. (2009), Li et al.
(2008,2009a,d,e,2010a,b),
Li (2009), Sritularak and
Likhitwitayawuid (2009),
Wang et al. (2010a)
D. parishii Alkaloids: dendroparine (E); Leander and Lu
¨ning (1968)
D. pierardii Alkaloids: pierardine (D2); Elander et al. (1971)
D. plicatile Bibenzyls: batatasin III (A); 3-O-methylgigantol (A)
Phenanthrenes: moscatin (A1); 2,6-dihydroxy-5,7-dimethoxyphenanthrene (A1);
3-hydroxy-2,4,7-trimethoxyphenanthrene (A1); plicatol A (A1); plicatol C (A2);
2-hydroxy-5,6,7-trimethoxy-9,10-dihydrophenanthrene (A2); lhridinusiant (A2);
erianthridin (A2); hircinol (A2); 4,40,7,70-tetrahydroxy-2,20-dimethoxy-9,90,10,100-
tetrahydro-1,10-biphenanthrene (A2); ephemeranthoquinone (C2)
Yamaki and Honda (1996),
Honda and Yamaki (2000,
2001)
D. polyanthum Bibenzyls: moscatilin (A); gigantol (A); batatasin III (A)
Phenanthrenes: moscatin (A1); 2,4,7-trihydroxy-9,10-dihydrophenanthrene (A2);
hircinol (A2)
Sesquiterpenoids: corchoionoside C (D1)
Other kinds of compounds: steroids
Hu et al. (2009)
D. primulimun Alkaloids: dendroprimine (B2); hygrine (C)
Sesquiterpenoids: corchoionoside C (C1)
Other kinds of compounds: steroids
Blomqvist et al. (1972), Luning
and Leander (1965), Hu
(2007)
D. rotundatum Bibenzyls: batatasin III (A)
Phenanthrenes: moscatin (A1); 2,7-dihydroxy-3,4,6-trimethoxyphenanthrene (A1);
nudol (A1); plicatol C (A2); 2,7-Dihydroxy-3,4,6-trimethoxy-9,10-
dihydrophenanthrene (A2)
Majumder and Pal (1992)
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Table 1 continued
Dendrobium species Components Refs.
D. secundum Bibenzyls: moscatilin (A); 4,5,40-Trihydroxy-3,30-dimethoxybibenzyl (A); brittonin A
(A)
Sritularak et al. (2011b)
D. snowflake Alkaloids: mubironine A (A1); mubironine B (A1); mubironine C (A2)
Sesquiterpenoids: flakinin B (A2); flakinin A (A3);
Morita et al. (2000)
D. sonia Bibenzyls: gigantol (A); 3-O-methylgigantol (A)
Phenanthrenes: confusarin (A1); nudol (A1); lhridinusiant (A2)
Huang et al. (2000)
D. thyrsiflorum Bibenzyls: moscatilin (A); gigantol (A); tristin (A)
Phenanthrenes: moscatin (A1); denthyrsinin (A1); denthyrsinol (A1); hircinol (A2);
densiflorol B (C1); denthyrsinone (C1)
Fluorenones: dendroflorin (A1); denchrysan A (A1); dengibsin (A1); denchrysan B
(A2)
Coumarins: scoparone (B); scopoletin (B); scopolin (B); xeroboside (B); denthyrsin
(B); ayapin (C1)
Other kinds of compounds: monoaromatics; flavonoids; steroids; terpenes;
anthraquinones
Zhang et al. (2004,2005a,b),
Liu et al. (2011), Wrigley
(1960)
D. trigonopus Bibenzyls: moscatilin (A); gigantol (A); tristin (A); trigonopol B (B3); trigonopol A
(B4)
Phenanthrenes: moscatin (A1); hircinol (A2)
Fluorenones: dendroflorin (A1)
Other kinds of compounds: lignans; steroids; flavonoids
Hu (2007), Hu et al. (2008b),
Zhang et al. (2005c)
D. wardianum Alkaloids: dendrowardine (A5) Glomqvist et al. (1973)
a
Code for chemical skeleton of each kind of compounds
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five-membered C2–C9-linked N-heterocycle and a
C3–C5-linked lactonic ring (Fig. 2a, 1). Various
substituent groups, frequently a methyl group, appear
on the N atom. In particular, the C2–C9 N-heterocycle
and C3–C5 lactonic ring are open in some sesquiterp-
enoid alkaloids from Dendrobium species (Fig. 2a,
2–4). Indolizidine alkaloids in Dendrobium are
formed by mixed-joint multiple substituted piperi-
dine(s) and pyrrolidine with mutual C and N atoms
(Fig. 2b, 1–2). Substituent groups, such as methyl,
hydroxyl, acetyl and phenyl, are always present on the
piperidine(s). Indolizidine alkaloids have only been
found in Dendrobium crepidatum and D. primulinum.
The structures of pyrrolidine alkaloids, isolated
mainly from D. chrysanthum, are simple. Only one
or two pyrrolidines linked by di-substituted acetonyl,
with some ordinary substituents, such as cinnamoyl,
methyl and acetonyl, compose this kind of alkaloid
N
HH
H
R
R
HO COOCH3
O
HH
H
R
O
O
N
R
O
R
H
R
O
O
N
O
R
H
R
N
COOCH
3
N
H
R
H
R
R
H
R
NR
R
R
N
R
H
R
R
N
N
O
N
O
O
O
H
N
a
(1) (2)
(3) (4) (5)
b
(1) (2)
c
d
(1) (2)
e
N
R
RR
R
R
R
O
O
R
1
2
3
4
5
6
7
8
9
Fig. 2 Chemical skeletons of alkaloids in Dendrobium.aSesquiterpenoid type; bindolizidine type; cpyrrolidine type; dphthalide
type; eimidazole type
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(Fig. 2c). The other two types of alkaloids, phthalides
and imidazoles, are rarely found in the four Dendro-
bium species investigated (Table 1; Fig. 2d, e).
Main aromatics
A large number of aromatic compounds, represented
by bibenzyls, phenanthrenes, fluorenones and couma-
rins, have been reported from Dendrobium.
Bibenzyls are widespread in different Dendrobium
species. For example, moscatilin and gigantol have
been isolated from nearly twenty species of Dendro-
bium (Table 1). The structures of the major bibenzyls
in Dendrobium are simple and generally consist of a
basic framework, bibenzyl, also known as 1,2-diphen-
ylethane, with substituents, always located at the para-
and/or meta-positions on the benzene ring C atoms
which are substituted by ethyl (Fig. 3a). The
R
R
R
R
R
R
R
R
R
R
R
O
O
R
R
OO
O
R
R
R
R R
R
R
O
R
R
R
R
R
R
O
R
R
R
R R
R
O
O
R
OCH3
R
R
H3CO
OCH3
R
R
a
b
(1) (2)
(3)
(4)
(5) (6)
(7)
1
2
3
4
56
7
8
1,
2,3,
4,
5,
6,
Fig. 3 Chemical skeletons
of bibenzyls in Dendrobium.
aSimple bibenzyls;
bintricate bibenzyls
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substituents are frequently hydroxyl and/or methoxyl,
and sometimes phenyl, phenoxyl, phenacetyl and
glucosyl. The total number of these groups is between
3 and 6. The structural diversity of bibenzyls in
Dendrobium depends on the type, number and position
of these substituents. In particular, the two C atoms in
ethyl (C7 and C8) can rarely be substituted. Interest-
ingly, none of the bibenzyls in Dendrobium has been
found with mono-substitution. The same situation
also occurs with phenanthrenes (except for
phenanthraquinones) and fluorenones in Dendrobium.
The other bibenzyls found in Dendrobium species
possess more intricate structural characteristics
(Fig. 3b). In these bibenzyl derivatives, one of the
two benzene rings in bibenzyl is always combined
with an intricately substituted oxygenic (benzo-)
heterocycle. This kind of bibenzyl has been found in
abundance in D. officinale.
Most natural phenanthrenes in Dendrobium species
appear to be hydroxyl- and/or methoxyl-substituted
R
R
RR
R
R
R
R
RR
R
R
RR
R
R
R
R
RR
O
O
RR R
R
R
RO
OR
R
R
R
O
R
OH
RHO
O
R
OH
HO
HO
HO
HO
O
R
R
HO
HO
OCH
3
O
R
R
R
R
R
O
O
O
R R
R
a
(1) (2)
c
(1) (2)
(3)
b
(4)
(1) (2)
(3) (4)
1
2
3
4
5
6
7
8
910
O
OO
R
O
R
Fig. 4 Chemical skeletons
of phenanthrenes in
Dendrobium.aSimple
phenanthrenes; bintricate
phenanthrenes;
cphenanthrenequinones
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9,10-dihydro or dehydro derivatives (Table 1;
Fig. 4a). The numbers of hydroxyl and methoxyl
moieties are also between 3 and 6, and can be found
usually at C2–7 and sometimes at C1, C8 and C9.
Furthermore, C4 and C5 in some phenanthrenes in
Dendrobium can be linked with a di-substituted ester
or methoxyl group to form an oxygen-bearing hex-
atomic ring or lactonic ring. Additionally, some novel
types of 9,10-dehydro and dihydro-phenanthrene
combined with miscellaneous substituted pyran or
furan have also been isolated and identified from
several Dendrobium species (Fig. 4b). Another type of
phenanthrenes found in Dendrobium is the group of
phenanthraquinones. 1,4-phenanthraquinone and
9,10-dihydro-1,4-phenanthraquinone are frequent
skeletons of phenanthraquinones in Dendrobium
(Table 1; Fig. 4c).
Fluorenones and coumarins are widespread in
Dendrobium species as well. However, the quantities
of these two categories of aromatics in Dendrobium
are much lower than bibenzyls and phenanthrenes.
Universally, C1–8 of the fluorenones in Dendrobium
are selectively substituted by 3 to 5 hydroxyls and
methoxyls (Fig. 5a). As to coumarins in Dendrobium
species, they generally consist of a coumarin skeleton
with C5 and C6, sometimes C2, substituents, mostly
hydroxyls and methoxyls (Fig. 5b, c). It is worth
mentioning that D. densiflorum and D. thyrsiflorum are
the richest resources for coumarins.
Sesquiterpenoids
Sesquiterpenoids are also frequently found in Dendr-
obium species. Unlike aromatics in Dendrobium,
which are widely distributed, sesquiterpenoids have
been found in only nine Dendrobium species so far, and
the majority is only found in D. nobile and D.
moniliforme (Table 1). As shown in Table 1, the
picrotoxane type is the most common sesquiterpenoid
isolated from Dendrobium (Fig. 6a). Similar to ses-
quiterpenoid alkaloids in Dendrobium, the picrotoxane
skeleton is sometimes combined with C2–C9- and/or
C3–C5-linked, rarely C5–C7 or C5–C10-linked, lac-
tonic rings (Fig. 6a). General substituents, mostly
hydroxyl and/or hydroxymethyl, and occasionally
methyl, methoxyl, carboxyl, carbonyl or glycosyl, are
found on the picrotoxane-type skeleton. In particular,
C5 and C9 in the picrotoxane skeleton can be linked
with a carbonyl (Fig. 6a). The alloaromadendrane
type, another kind of sesquiterpenoid (Fig. 6b), is also
rich in D. nobile and D. moniliforme. Methyl is always
attached to the C4 of the alloaromadendrane skeleton
while several kinds of substitutions frequently happen
at C10 and C11. Furthermore, other types of sesquit-
erpenoids, such as cyclocopacamphane, cadinene,
emmotin and muurolene, have also been found, mainly
in D. nobile (Fig. 6c).
Other small molecules
In addition to the above mentioned characteristic
components in Dendrobium, other common types of
micro-molecular compounds have also been isolated
from many Dendrobium species (Table 1) and most of
them are mono-aromatics, lignans, steroids, flavo-
noids, or anthraquinones.
Polysaccharides
Polysaccharides, a class of carbohydrate consisting of
numerous (usually more than ten) monosaccharides
linked by glycosidic bonds in branched or unbranched
chains, are usually considered as one of the most
important active compounds in medicinal plants.
Polysaccharides always present with significant
amounts in Dendrobium, even representing up to
nearly 50% of the total dry weight in some species, e.g.
D officinale (Li and Xu 1990), and have been
O O
R
RR
O O
O
O
a
c
b
O O
O
O(1) (2)
O
R
R
R
R
RR
R
R
HO
R
R
R
(1) (2)
1
2
3
45
6
7
8
1
2
3
4
7
5
6
Fig. 5 Chemical skeletons of fluorenones (a) and coumarins (b,
c)inDendrobium
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experimentally proven to exert multiple biological
properties, such as immuno-modulation, anti-tumor
and anti-oxidant activity (Ng et al. 2012).
To date, several kinds of polysaccharides have been
isolated and purified from Dendrobium species
(Table 2). However, compared with studies on
micro-molecular compounds, reports on the chemistry
with regard to isolation, purification, and in-depth
structural elucidation of the polysaccharides in Dendr-
obium are limited and only focus on six frequently
used species in China, i.e., D. officinale,D. nobile,D.
huoshanense,D. aurantiacum var. denneanum,D.
moniliforme and D. aphyllum, as summarized in
Table 2. As shown in Table 2, there are discrepancies
in reports of the molecular weights of the purified
polysaccharides from these Dendrobium species.
Glucose, mannose and galactose, which are most
frequently found, are the three main monosaccharides
comprising the polysaccharides isolated from Dendr-
obium. In addition, other monosaccharides and uronic
HO
H
O
O
R
RHO
H
R
HO
O
O
R
R
R
R
H
O
R
H
H
RR
RR
H
H
O
OH
R
R
H
H
OH
OH
O
R
O
H
H
H
H
H
OH
R
R
R
H
R
R
H
OH
H
R
H
H
R
R
R
ab
c
(1) (2) (3) (4)
(5)
(1) (2) (3)
(4) (5) (6)
O
HH
OH
HO
O
O
R
R
R
O
O
RRR
R
R
R
H
R
R
R
R
R
R
(6)
1
2
3
4
5
6
7
8
9
10
1
2
3
4
56
7
8
910
11
Fig. 6 Chemical skeletons
of sesquiterpenoids in
Dendrobium.aPicrotoxane
type; balloaromadendrane
type; cother types
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acids, such as arabinose, rhamonose, xylose and
galaturonic acid, also occasionally appeared in the
backbone or branched and terminal residues of
purified Dendrobium polysaccharides. Moreover, glu-
cosidic bonds in Dendrobium polysaccharides are
complicated, mainly including 1 ?4, 1 ?6or
Table 2 Polysaccharides isolated and purified from Dendrobium spp.
b
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1?3 linkages. Pyranosyls with a-or b-configuration
are prevalent in the polysaccharides found in
Dendrobium.
Bioactivity
According to traditional Chinese medical theory,
Dendrobium is an herbal tonic for supplementing the
stomach, promoting the production of body fluids,
nourishing Yin, and clearing heat. At present, accu-
mulating studies provide evidence that Dendrobium
demonstrates extraordinarily comprehensive bioactiv-
ities, involving the immune, nervous, cardiovascular,
endocrine, gastrointestinal and urinary systems (Ng
et al. 2012).
Nonetheless, bioactivity studies on Dendrobium
still suffer from serious problems. All too often,
pharmacological effects of Dendrobium extracts or its
pure components have been tested and verified only by
in vitro experiments. Crucial factors that might
directly influence in vivo efficacy, such as bioavail-
ability and pharmacokinetics, can not be considered by
in vitro experiments. Thus, to assess the actual activity
of Dendrobium, in vivo experiments must be executed.
To provide an example, gigantol, a bibenzyl that
normally occurs in Dendrobium, has been reported to
possess multiple positive effects that correlate
with molecular mechanisms according to in vitro
experiments, including anti-cataract, anti-tumoral,
anti-mutagenic, anti-inflammatory, and antioxidant
effects (Wei et al. 2011; Won et al. 2006; Miyazawa
et al. 1997; Simmler et al. 2009). However, few in vivo
studies have been carried out to further confirm the
bioactivity of gigantol.
Secondly, the concentration-effect paradigm, also
called the dose–response relationship, of Dendrobium
extracts or components should be a factor of concern
in evaluating studies. For example, many reports state
that purified polysaccharides from different Dendro-
bium plants present competitive antioxidant activity
(Lin et al. 2003). However, the dosages are often
Table 2 continued
Manp, mannopyranosyl; Glcp, glucopyranosyl; OAc, O-acetyl; Araf, arabinofuranosyl; Galp, galactopyranosyl; Arap,
arabinopyranosyl; Rhaprhamnopyranosyl
Man, mannose; Glc, glucose; Ara, arabinose; Gal, galactose; Xyl, xylose; Rha, rhamnose; GalA, galacturonic acid
a
No informations
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amazingly unreasonable. DFHP, a water-soluble poly-
saccharide isolated from D. fimbriatum, was tested for
its in vitro antioxidant activity (Luo and Fan 2011). In
the scavenging activity on ABTS assay, DFHP showed
a high scavenging effect on ABTS at 3.0 mg/mL,
reaching 90.05%, which was close to that of vitamin C
in the same concentration (P\0.05). However, it
should be noticed that the scavenging effect on ABTS
of vitamin C at 0.25 mg/mL (about 90%) was already
close to the level achieved at 3.0 mg/mL, but
obviously much stronger than that of DFHP at
0.25 mg/mL (less than 30%). In other words, the
scavenging effect on ABTS of DFHP at 3.0 mg/mL
was similar with that of vitamin C at just 0.25 mg/mL.
Generally, extraordinarily high concentrations of an
extract or a natural product can get a ‘‘satisfactory’’
pharmacological response (Gertsch 2009). Unfortu-
nately, the conclusion ‘‘the results indicated that
DFHP had strong scavenging power for ABTS radi-
cals and should be explored as novel potential
antioxidants’’ was readily obtained when the similar
scavenging effects on ABTS of DFHP and vitamin C
were compared at a considerably high concentration
(3.0 mg/mL). Additionally, beyond the concentration-
effect paradigm, the yield of extracts or refined single
components in Dendrobium herbal materials needs to
be determined and calculated in order to determine
potentially effective dosages for whole herbal material
or to evaluate the feasibility of using herbal materials
as sustainable resources. This issue has been ignored
in most related published papers.
Thirdly, apart from pure components, most in vitro
and in vivo pharmacological studies on Dendrobium
used crude extracts, such as aqueous extracts, alcohol
extracts, crude polysaccharides and total alkaloids
(Lin et al. 2003). However, the specific bioactive
substances in these crude extracts are obscure, and
such information is not helpful for development of
novel natural products from Dendrobium medicinal
plants because it is difficult to standardize the crude
extracts. Thus, crude Dendrobium extracts should be
further investigated for particular components that are
responsible for bioactivity. Furthermore, the interac-
tion between components in crude Dendrobium
extracts should also be studied to reveal the scientific
basis that multiple components interact to create
holistic therapeutic actions in traditional Chinese
medicines.
Quality control
Qualitative analysis
Authentication
Due to the distinct chemical components, bioactivities
and clinical effects of different Dendrobium species,
authentication of Dendrobium is crucial and the first
step for implementing its rational administration as a
medicine. Traditional morphological and microscopic
approaches along with molecular techniques used for
Dendrobium authentication have been reviewed in
detail (Zhang et al. 2005d). On the other hand, the
diverse chemical components of different Dendrobi-
um herbs make it possible to identify and discriminate
Dendrobium species by chemical methods. Recently,
multiple chromatographic fingerprints, such as high
performance liquid chromatography (HPLC) (Zhang
et al. 2003b), capillary electrophoresis (CE) (Zha et al.
2009), gas chromatography (GC) (Wang et al. 2011a)
and thin-layer chromatography (TLC) (Wang et al.
2003), have been readily exploited for successful
identification and discrimination of five Dendrobium
species. In addition, some spectroscopic methods such
as
1
H nuclear magnetic resonance (
1
H-NMR) (Zhang
et al. 2007b), infra-red spectrum (IR) (Li et al. 2009c),
near infra-red spectrum (NIR) (Wang et al. 2009a) and
ultraviolet spectrum (UV) (Teng et al. 2009) are also
being employed for fingerprint analysis and/or dis-
crimination of Dendrobium species.
In general, though extensive work has been con-
ducted for authentication of Dendrobium species,
problems still exist. Morphological and microscopic
identification is very limited for Dendrobium herbs or
processed products with similar macroscopic and
anatomical characteristics. Molecular methods are
quite effective, but might be not appropriate for
routine use owing to the high cost. In spite of the
feasibility of using chromatography for routine sample
authentication, current and future studies on the
development of fingerprint methods for authentication
of Dendrobium species should be more comprehen-
sive and be concerned with not only species, but also
other factors that could cause chemical inconsistency,
such as sample localities, harvesting time, and
processing methods. Spectroscopic methods could be
used for ordinary discrimination of Dendrobium
Phytochem Rev (2013) 12:341–367 357
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species, but they are very limited in Dendrobium
authentication due to their poor specificity. Hence,
abundant exploratory studies are still needed.
Qualitative analysis of polysaccharides
Quality control of polysaccharides remains a chal-
lenge because of their complicated structures and
macro-molecular mass. Generally, isolation and puri-
fication followed by complete structural characteriza-
tion is the most reliable method for quality evaluation
of polysaccharides in medicinal herbs (Table 2).
However, this procedure is complex and time con-
suming. Therefore, over the past 20 years, rapid and
convenient methods for qualitative analysis of poly-
saccharides in Dendrobium have been developed, in
which structural information of the investigated poly-
saccharides could be partially represented in different
ways. Pre-column derivatization HPLC (Zhou and Lv
2011), TLC (Huang and Ruan 1997), GC (Luo et al.
2011) and derivatization polyacrylamide gel electro-
phoresis (PAGE) (Zha et al. 2012) analysis based on
the constituent saccharides profiles produced by total
or partial acid hydrolysis have been frequently used
for characterization and quality control of crude
polysaccharides from different Dendrobium herbs.
However, the selectivity of acid hydrolysis for differ-
ent glycosidic bonds is poor, which limits the struc-
tural characterization for various polysaccharides.
Consequently, several novel methods were estab-
lished, in which polysaccharides from Dendrobium
were selectively hydrolyzed by specific carbohydras-
es, especially glycosidases, with more moderate
conditions. A new ‘‘saccharide mapping’’ based on
enzymatic (carbohydrase) digestion and subsequent
chromatographic analysis of enzymatic hydrolysate
was successfully employed for discrimination of crude
polysaccharides from different Dendrobium species as
well as the same species grown in different localities
(Xu et al. 2011). Analogously, enzymatic fingerprints
derived from carbohydrase hydrolysis followed by
PAGE analysis were also created for species and
locality identification of Dendrobium (Zha et al.
2012). These methods, based on specific glycosidic
bonds, provide a different approach to the concise
discrimination of polysaccharides from various ori-
gins and are helpful for assessing the pharmaceutical
or therapeutic quality of polysaccharides in
Dendrobium.
Quantitative analysis
Polysaccharides, alkaloids and aromatics have been
proven to be largely responsible for the many biolog-
ical activities of Dendrobium (Ng et al. 2012). Thus,
quantitative analysis for the quality control of Dendr-
obium has mostly focused on these kinds of com-
pounds. To date, a series of analytical methods have
been employed and reported to quantify the contents
of active components in various Dendrobium species.
However, it should be noted that although sesquiterp-
enoids are also widely distributed in Dendrobium with
proved bioactivities, studies on the quantitative anal-
ysis of sesquiterpenoids in Dendrobium has not been
carried out yet.
Colorimetry and titration
The contents of total alkaloids and polysaccharides in
Dendrobium have been determined by colorimetry and
potentiometric titration (Li et al. 2002; Sun et al. 2009;
Zhang et al. 2001; Zhu et al. 2010a,b). However, these
methods, though simple and rapid, are sometimes
unreliable due to the effects of uncontrolled experi-
mental conditions (Xu 2001; Hua et al. 2010).
Chromatography
Currently, HPLC coupled with different detectors,
such us UV and MS, has become the preferred
analytical technique for separation and quantification
of markers from complicated Chinese medicinal
material extracts, due to its many advantageous
features, including high resolution, favourable repro-
ducibility and powerful maneuverability (Liang et al.
2009). HPLC methods for quantitative analysis of
Dendrobium are summarized in Table 3. It can be seen
that aromatic compounds, e.g., bibenzyls, phenan-
threnes, fluorenones and coumarins, and alkaloids are
always selected as chemical markers in HPLC quan-
titative analysis for the quality control of Dendrobium
species. UV detection is mostly employed in these
methods. Electrospray ionization (ESI)–mass spec-
trometry (MS) detection is seldomly used in HPLC
analysis for further structural elucidation of targeted
compounds in the quality control of Dendrobium.
However, differing from aromatics with intense
absorption in the ultraviolet region, alkaloids of
358 Phytochem Rev (2013) 12:341–367
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Table 3 HPLC applications on quantitative analysis for quality control of Dendrobium spp.
Analytes Samples Extraction method Column Mobile phase Analytical
time (min)
Detection Refs.
Bibenzyls,
fluorenones and
phenanthrenes (11
chemical markers)
31 Dendrobium
species
Ultrasonic extraction with
80% (v:v) methonal
aqueous solution
ODS (Beckman
Coulter
TM
)
(4.6 mm 9250 mm,
5lm)
Acetonitrile–1 %TFA,
gradient elution
Flow rate: 1.0 mL/min
45 UV 280 nm Yang et al.
(2006c)
Bibenzyls,
phenanthrenes and
coumarins (9
chemical markers)
D. aurantiacum
var. denneanum
Ultrasonic extraction with
80% (v:v) methonal
aqueous solution
ODS (Beckman
Coulter
TM
)
(4.6 mm 9250 mm,
5lm)
Acetonitrile–5 %formic
acid, gradient elution
Flow rate: 1.0 mL/min
50 UV 280 nm
ESI–MS
Yang et al.
(2007e)
Bibenzyls,
fluorenones and
phenanthrenes (6
chemical markers)
D. thyrsiflorum Soak and then ultrasonic
extraction with 80%
(v:v) methonal aqueous
solution
ODS (Beckman
Coulter
TM
)
(4.6 mm 9250 mm,
5lm)
Acetonitrile–1 %TFA,
gradient elution
Flow rate: 1.0 mL/min
55 UV 280 nm Yang et al.
(2008)
Bibenzyls,
fluorenones and
phenanthrenes (6
chemical markers)
D. chrysotoxum Refluxing extraction with
chloroform
ODS (Shim-Pack CLC)
(4.6 mm 9200 mm)
Methanol–water (58:42)
Flow rate: 1.0 mL/min
35 UV 237 nm Yang et al.
(2005a)
Bibenzyls and
phenanthrenes (3
chemical markers)
16 Dendrobium
species
Refluxing extraction with
chloroform
ODS (DICP, China)
(4.6 mm 9240 mm)
Methanol–acetonitrile–water
(60:60:165)
Flow rate: 1.2 mL/min
40 UV 237 nm Ma et al.
(1994a)
Bibenzyls (2
chemical markers)
15 Dendrobium
species
Refluxing extraction with
chloroform
ODS (Shim-Pack CLC)
(4.6 mm 9200 mm,
5lm)
Methanol–water (60:40)
Flow rate: 1.0 mL/min
40 UV 237 nm Ding et al.
(2008)
Bibenzyls (2
chemical markers)
18 Dendrobium
species
Ultrasonic extraction with
methonal
RP-18 (Waters
XTerra
TM
)
(4.6 mm 9250 mm,
5lm)
Acetonitrile–0.1 %TFA,
gradient elution
Flow rate: 1.0 mL/min
35 UV 230 nm Xu et al.
(2010a)
Bibenzyls (2
chemical markers)
6Dendrobium
species
Ultrasonic extraction with
60% (v:v) methonal
aqueous solution
C18 (Shimadzu)
(2.1 mm 9150 mm,
5lm)
Acetonitrile with 1 %formic
acid–1 %formic acid,
gradient elution
40 UV 270 nm Zhou et al.
(2010a)
Bibenzyls (1
chemical marker)
D. aurantiacum
var. denneanum
Ultrasonic extraction with
methonal
ODS (Shim-Pack CLC)
(4.6 mm 9150 mm,
5lm)
Acetonitrile–2 %formic
acid (35:65)
Flow rate: 1.0 mL/min
25 UV 280 nm Yang et al.
(2007b)
Bibenzyls (1
chemical marker)
D. chrysotoxum Ultrasonic extraction with
methonal
XDB-C18 (Agilent
Zorbax Eclipse)
(4.6 mm 9250 mm,
5lm)
Methanol–acetonitrile–water
(30:30:40)
Flow rate: 1.0 mL/min
18 UV 232 nm Xia et al.
(2008)
Phytochem Rev (2013) 12:341–367 359
123
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Table 3 continued
Analytes Samples Extraction method Column Mobile phase Analytical
time (min)
Detection Refs.
Alkaloids (1
chemical marker)
D. nobile Infiltration with aqueous
ammonia and then
refluxing extraction
with chloroform
RP-18 (Waters
XTerra
TM
)
(3.9 mm 9150 mm,
5lm)
Acetonitrile–water–TEA
(21:79:0.005)
Flow rate: 1.0 mL/min
25 UV 210 nm Li et al.
(2009b)
Alkaloids (1
chemical marker)
D. nobile Ultrasonic extraction with
chloroform
XDB-C18 (Agilent
ZORBAX)
(4.6 mm 9250 mm,
5lm)
Acetonitrile–phosphate
buffer (pH =8.0),
gradient elution
Flow rate: 0.8 mL/min
38 UV 198 nm Xie (2008)
Coumarins and
2-glucosyloxy-
cinnamic acids (6
chemical markers)
D. thyrsiflorum Soak and then ultrasonic
extraction with 50%
(v:v) methonal aqueous
solution
C18 (Polaris)
(4.6 mm 9250 mm,
5lm)
Acetonitrile–5 %acetic
acid, gradient elution
Flow rate: 0.8 mL/min
45 UV 342 nm
ESI–MS
Zhang et al.
(2006a)
Coumarins (2
chemical markers)
D. thyrsiflorum Ultrasonic extraction with
methonal
ODS (Meta Chem)
(4.6 mm 9250 mm,
5lm)
Methanol–THF–1% acetic
acid (15:5:80)
Flow rate: 1.0 mL/min
20 UV 342 nm Zhang et al.
(2006b)
Coumarins (1
chemical marker)
8Dendrobium
species
Infiltration with aqueous
ammonia and then
refluxing extraction
with chloroform
C18 (Kromasil)
(4.6 mm 9250 mm,
5lm)
Acetonitrile–water (20:80)
Flow rate: 1.0 mL/min
25 UV 343 nm Sun et al.
(2008)
Coumarins (1
chemical marker)
D. aurantiacum
var. denneanum
Ultrasonic extraction with
methonal
C18 (Diamonsil)
(4.6 mm 9200 mm,
5lm)
Methonal–water (30:70)
Flow rate: 1.0 mL/min
35 UV 274 nm Zhou et al.
(2010b)
2-Glucosyloxy-
cinnamic acids (3
chemical markers)
3Dendrobium
species
Soak and then ultrasonic
extraction with 50%
(v:v) methonal aqueous
solution
ODS-80Ts (Tosoh)
(4.6 mm 9150 mm,
5lm)
Methanol–5 %formic acid,
gradient elution
Flow rate: 0.8 mL/min
50 UV 270 nm
ESI–MS
Yang et al.
(2007d)
TFA, trifluoroacetic acid; THF, tetrahydrofuran; TEA, triethylamine
360 Phytochem Rev (2013) 12:341–367
123
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Dendrobium, especially the sesquiterpenoid alkaloids,
are extremely weak in ultraviolet absorption due to the
absence of conjugated double bonds in their chemical
structures. Thus, HPLC–UV methods for quantifica-
tion of sesquiterpenoid alkaloids of Dendrobium,
which are usually poorly sensitive, are actually
inappropriate. Some other universal or sensitive
approaches, such as evaporative light scattering
detection (ELSD) or mass spectrometry, are suggested
to be used to improve sensitivity. Additionally,
comprehensive analysis, for example, simultaneous
determination of multiple bioactive components by
HPLC, is also desirable because the ‘‘holistic’’ actions
of medicinal herbs are ascribed to complex chemicals.
However, so far limited work has been done for the
‘‘holistic’’ quality control of Dendrobium.
Ultra-performance liquid chromatography (UPLC),
utilizing sub-2 lm particles as solid phase and oper-
ating at much higher system pressure than that of
HPLC, could perform analyses with higher resolution,
greater sensitivity and greater speed with little solvent
consumption. So UPLC has been more and more
dominant in the area of pharmaceutical analysis,
especially in the analysis of traditional Chinese
medicines (Liang et al. 2009). Nevertheless, so far,
only one study has reported on quantitative analysis
for the quality control of Dendrobium by UPLC (Xu
et al. 2010b), in which five components of Dendro-
bium, of three types, were baseline-separated within
6 min. With apparent superiority compared with
HPLC with regard to resolution, sensitivity and
analytical time, UPLC coupled with multiple detec-
tors, such as UV and MS, should be widely used in
qualitative and quantitative analysis for quality eval-
uation of Dendrobium in the future.
GC and TLC are also repeatedly used for quanti-
tative purposes in quality control of Dendrobium (Cai
et al. 2011; Wang and Zhao 1985). But their applica-
tion is limited since GC is only available for volatile
components while TLC quantification is relatively
poor in reproducibility, resolution and sensitivity.
In short, numerous methods of qualitative and
quantitative analysis for the quality assessment of
Dendrobium have been developed. However, due to
the extraordinary differences in morphological, micro-
scopic, molecular and chemical characteristics of
different Dendrobium herbs, establishing a universal
approach for quality evaluation of multiple Dendro-
bium herbs remains difficult—a goal, not yet a reality.
Acknowledgments This study was supported by Hong Kong
Chinese Materia Medica Standards Phase VII Project from
Department of Health, the Government of the Hong Kong
Special Administrative Region (DH/TCMD/HKCMMS/5-80/
180C) and the Non-profit Special Fund from State
Administration of Traditional Chinese Medicine of the
People’s Republic of China (No. 201307008).
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