2014, Vol. 6
引用本文 | doi: 10.1016/S1674-6384(14)60028-9 |
, Pei-gen Xiao1
2. Xinjiang Institute of Chinese and Ethnic Medicine, Urumqi 830002, China
Genus Kadsura Kaempf. ex Juss. (family Schisandraceae) comprises 16 species, mainly distributed in Asia, and eight of them existed in the south and southeast of China (Wu et al, 2008; Saunders, 1998). The plants of the genus have been used as folk medicines for a long time to activate blood and resolve stasis, promote qi circulation to relieve pain, dispell wind and eliminate dampness (Liu et al, 2012). Some species such as K. interior, K. coccinea, K. longipedunculata, and K. heteroclita, have been recorded in Chinese Pharmacopoeia 2010 (Pharmacopoeia Committee of P. R. China, 2010) and Provincial Chinese Materia Medica Standards (Fujian Food and Drug Administration, 2006; Guangdong Food and Drug Administration, 2004). (Figure 1)
 | Figure 1 Some morphological characters in plants of genus Kadsura Kaempf. ex Juss. |
In recent years，genus Kadsura Kaempf. ex Juss. has been extensively studied in chemical constituents including lignans，triterpenoids，flavonoids，sesquiterpenoids， and so on. Among them，lignans and triterpenoids were the main characteristic constituents with various biological activities. Since the pharmacological studies have been reviewed in our previous paper(Liu et al，2014)，we summarized the chemical constituents including bioactive compounds isolated from the plants of genus Kadsura Kaempf. ex Juss. over the past 20 years， and provided a primary and strategic platform for the further development and utilization of the medicinal value and resources in the plants of genus Kadsura Kaempf. ex Juss.
2. Chemical constituentsMore than 450 compounds had been isolated and identified from the plants of genus Kadsura Kaempf. ex Juss.，which could enrich the abundant constituents in the natural products in Schis and raceae plants. They were lignans，triterpenoids，flavonoids，sesquiterpenoids，etc. Among them，lignans and triterpenoids were the main chemical constituents，which were the research hotspots for their bioactivities in anti-HIV，antitumor，antihepatitis treatment and so on. Their names，structures， and corresponding plant sources were collected as follows.
2.1 LignansLignans were the major constituents in the plants of genus Kadsura Kaempf. ex Juss. Two hundred and eighty-five lignans had been identified and divided into five categories，dibenzocyclooctadienes(A)，spirobenzofuranoid dibenzocyclooctadienes(B)，aryltetralins(C)，diarylbutanes(D)， and tetrahydrofurans(E).
2.1.1Dibenzocyclooctadienes(A)abundant dibenzocyclooctadienes were isolated from the plants of genus Kadsura Kaempf. ex Juss.，occupying above half of total lignans(Table 1). According to their different configurations and conformations，dibenzocyclo- octadienes could be further classified into three categories: S-twist boat chair(S-TBC)，R-TBC， and S-TB，more than half of which were S-TBC. In addition，a special type of dibenzo- cyclooctadienes isolated from the plants of genus Kadsura Kaempf. ex Juss. had an oxygen-bridged eight-membered ring.(Figure 2)
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Table 1Dibenzocyclooctadienes(A)isolated from genus Kadsura Kaempf. ex Juss. |
 | Figure 2 Structures of lignans(A)isolated from genus Kadsura Kaempf. ex Juss |
Fifty-three spirobenzofuranoid dibenzocyclooctadienes were isolated from the plants of genusKadsura Kaempf. ex Juss. Most of them were only found in this genus，considered as the characteristic chemical constituents in genus Kadsura Kaempf. ex Juss.， and demonstrated important taxonomic significance(Xu et al，2008b).(Table 2，Figure 3)
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Table 2Spirobenzofuranoid dibenzocyclooctadienes(B)isolated from genus Kadsura Kaempf. ex Juss |
 | Figure 3 Structures of lignans(B)isolated from genus Kadsura Kaempf. ex Juss |
This category contained eight compounds with the same nuclear structure. Kadsuralignans H(255) and C(257)were isolated from K. coccinea. Kadsurindutin C(256)was isolated from K. induta. Other five compounds，namely otobaphenol(258) and arisantetralone A−D(259−262)were isolated from K. longipedunculata.(Table 3，Figure 4)
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Table 3Aryltetralins(C)isolated from genus Kadsura Kaempf. ex Juss |
 | Figure 4 Structures of lignans(C)isolated from genus Kadsura Kaempf. ex Juss |
There were seventeen diarylbutane-type lignans isolated from Kadsura plants. Extensive phytochemical studies on the roots and stems of K. longipedunculata collected from different places resulted in the isolation of(+)-anwulignan(263)，dihydroguaiaretic acid(264)，monomethyl dihydro- guaiaretic acid(265)，saururenin(266)，mesodihydroguaiaretic acid(267)，isoanwulignan(269)，4-[4-(3，4-dime-thoxyphenyl)- 2，3-dimethyl-butyl]-2-methoxy-phenol(270)， and 3-methoxy- 3′，4′-(methylenedioxy)-9，9′-epoxylignan-4，7′-diol(271). Other diarylbutane-type lignans were also obtained from other species，including lengfantuanjing I(268)，kadcoccilignan(272)(from K. coccinea)，kadangustins J and K(273 and 274)，H(276)，I(277)，heteroclitin R(275)(from K. heteroclita)，meso-dihyroguaiaretic acid(278)(from K. angustifolia)， and kadsuphilin J(279)(from K. philippinensis).(Table 4，Figure 5)
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Table 4Diarylbutanes(D)isolated from genus Kadsura Kaempf. ex Juss |
 | Figure 5 Structures of lignans(D)isolated from genus Kadsura Kaempf. ex Juss |
Only six terahydrofuran-type lignans had been obtained from Kadsura plants，namely gr and isin(281)，kadlongirins A and B(282 and 283)，fragransin B(284)， and zuihonin A(285)isolated from K. longipedunculata， and veraguensin(280)isolated from an unidentified species of genus Kadsura Kaempf. ex Juss.(Liu and Huang， 1988; Pu et al，2008a; Zaugg et al，2011).(Figure 6)
 | Figure 6 Structures of lignans(E)isolated from genus Kadsura Kaempf. ex Juss |
Triterpenoid was another kind of major chemical constituent in the plants of genus Kadsura Kaempf. ex Juss. Up to now，160triterpenoids had been isolated and identified. According to their different structural skeleton，they could be classified into four categories: lanostane-type，cycloartane-type，nortriterpenoids， and others triterpenoids，which could be further divided into several sub-types because of the different oxygenated patterns and structure characteristics.
2.2.1Lanostane-type triterpenoids1)Intact lanostanes(F) This category contained 16 compounds featured by a hydroxyl group or ketone at C-3. Among them，only four members belonged to the C-3 hydroxyl substitution series，including epianwuweizic acid(1)isolated from the fruits of K. longipedunculata and the stems of K. angustifolia，anwuweizic acid(2)isolated from K. angustifolia，isoanwuweizic acid(4)isolated from the roots of K. heteroclita， and 3-hydroxy-12-acetoxycoccinic acid(15)isolated from K. coccinea. Ten other members had a ketone at C-3，namely coccinic acid(3)from K. coccinea，(24Z)- 3-oxo-12α-acetoxylanosta-8，24-dien-26-oic acid(5) and (24Z)-3-oxo-12α-hydroxylanosta-8，24-dien-26-oic acid(6)isolated from K. longipedunculata， and 12β-acetoxycoccinic acid(7)，12β-hydroxycoccinic acid(8)，12α-acetoxycoccinic acid(9)，12α-hydroxycoccinic acid(10)， and schisanhenric acid(11)isolated from K. heteroclita， kadnanosic acid B(14)isolated from K. ananosma， and kadindutic acid(16)isolated from K. induta. In addition，kadpolysperins D(12) and N(13)isolated from K. polysperma had an acetoxy at C-3.(Table 5，Figure 7)
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Table 5Intact lanostanes(F)isolated from genus Kadsura Kaempf. ex Juss |
 | Figure 7 Structures of triterpenoids(F，G， and H)isolated from genus Kadsura Kaempf. ex Juss |
2)3，4-Seco-lanostanes(G) There were nineteen 3，4-seco- lanostane type triterpenoids isolated from the plants of genus Kadsura Kaempf. ex Juss. including manwuweizic acid(17)，kadsuric acid(18)，kadpolysperins H(19)，B(20)，J(24)，K(25)，kadsuracoccinic acid A(21)，C(22)，B(27)，seco-coccinic acid F(23)，K(28)，J(32)，3，4-seco-(24Z)- lanosta-4(30)，8，24，triene-3，26-dioic acid(26)，schisanlactone F(30)，coccinilactone A(31)，seco-coccinic acid G(29)，kadnanosic acid A(33)，kadnanolactones D(34) and R(35)， and they were isolated from K. coccinea，K. ananosma， and K. polysperma，respectively. Moreover，manwuweizic acid(17) and kadsuric acid(18)were also isolated from K. renchangiana.(Table 6，Figure 7)
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Table 63，4-Seco-lanostanes(G)isolated from genus Kadsura Kaempf. ex Juss |
3)18(13→12)-Abeo-lanostanes(H) The first 18(13→12)-abeo-lanostane，ananosic acid A(40)，was isolatedfrom the stem barks of K. ananosma. Further phytochemical studies on the same plants led to the discovery of ananosic acids B−D(43−45). Kadpolysperins C(36)，L(37)，M(38)，E(41)，F(42)，G(46)，I(47)，20(R)，24(E)-3-oxo-9β-lanosta-7，24-dien-26-oic acid(39)，seco- coccinic acids A−F(48−53)， and I(54)were isolated and identified from K. polysperma and K. coccinea，respectively.(Table 7，Figure 8)
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Table 718(13→12)-Abeo-lanostanes(H)isolated from genus Kadsura Kaempf. ex Juss |
 | Figure 8 Structures of triterpenoids(H)isolated from genus Kadsura Kaempf. ex Juss |
4)14(13→12)-abeo-Lanostanes(I) Neokadsuranic acid A(55)，the first compound with 14(13→12)-abeo- lanostane skeleton，was isolated from the stem of K. heteroclita. From the same plants，seco-neokadsuranic acid A(60)was obtained. Following the discovery of compounds 55 and 60，other four compounds were isolated from other species，including neo- kadsuranic acids B−C(57−58)(from K. longipedunculata)，3-hydroxy-neokadsuranic acid A(56)from K. coccinea， and kadpolysperin A(59)from K. polysperma.(Table 8，Figure 9)
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Table 814(13→12)-Abeo-lanostanes(I)isolated from genus Kadsura Kaempf. ex Juss |
 | Figure 9 Structures of triterpenoids(I，J， and K)isolated from genus Kadsura Kaempf. ex Juss |
5)Norlanostanes(J) Only two norlanostanes were obtained from Kadsura plants，namely micranoic acid A(61) and seco-coccinic acid H(62)isolated from K. coccinea(Li et al，2008; Shinomiya et al，2009; Wang et al，2012c). This sub-type featured an unusual octanor-triterpenoid backbone degraded by the oxidative fission of the C-17−C-20 bond.(Figure 9)
2.2.2 Cycloartane-type triterpenoids1)Intact cycloartanes(K) This category of cycloartane-type triterpenoids featured a hydroxyl group or a ketone at C-3. There was only one C-3 hydroxyl-substituted member. Isoschiz and rolic acid(63)was isolated from an unidentified species of genus Kadsura Kaempf. ex Juss. Three C-3 ketone compounds，namely heteroclic acid(64)，cycloartenone(65)， and schis and ronic acid(66)were isolated from the stems of K. heteroclita. Another one，namely kadsulactone(67)，was isolated from K. longipedunculata.(Table 9，Figure 9)
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Table 9Intact cycloartanes(K)isolated from genus Kadsura Kaempf. ex Juss |
2)3，4-Seco-cycloartanes(L) 3，4-Seco-cycloartanes were abundant in the plants of genus KadsuraKaempf. ex Juss.， and 38 triterpenoids belonged to this group. Phytochemical studies on the roots and stems of K. heteroclita collected from different places resulted in the isolation of kadsuranic acid A(68)，changnanic acid(69)，nigranoic acid(70)，heteroclitalactones A−C(73−75)，D(91)， and E(92)，F(76)，G−M(96−102)，schisanlactone E(77)，3，4-secolanosta-4(28)，24-dien-26-oic acid 22，26-lactone(78)，3，4-secolanosta-4，24-dien-26-oic acid 22，26-lactone(79)，3，4-secolanosta-4(28)，6，24-trien-26-oic acid 22，26-lactone(80)， and schisanlactone B(86). Other 3，4-seco-cycloartanes triterpenoids were isolated and identified from other species，such as nigranoic acid(70)，angustific acid B(71)，angustifodilactones A(104) and B(105)from K. angustifolia，changnanic acid(69)，schisanlactone E(77)，kadsulactone acid(82)，kadsudilactone(84)，schisanlactone A(93)from K. longipedunculata，kadnanolactones B(72)，C(85)from K. ananosma，lancilactones A(94)，B(95)，C(82)，kadsulactone A(87)from K. lancilimba，polysperlactones A(103)，B(83)，schisanlactone E(77)from K.polysperma，kadsuphilactone B(88)from K. philippinensis，kadsulactone A(87)，renchang- lactone A(89)from K.renchangiana， and kadsudilactone(84)，kadsuphilactone B(88)， and kadcoccilactone Q(90)from K. coccinea.(Table 10，Figure 10)
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Table 103，4-Seco-cycloartanes(L)isolated from genus Kadsura Kaempf. ex Juss |
 | Figure 10 Structures of triterpenoids(L)isolated from genus Kadsura Kaempf. ex Juss |
3)14(13→12)-Abeo-cycloartanes(M) From the leaves and stems of K. longipedunculata，longipedlactones A−C，E−F，H，L，M，J(106−114)，longipedlactones D，G，I，N(115−118)，K(119)，O(120)， and P(121)were isolated，which showed an unprecedented rearranged pentacyclic system. Some of them were also isolated from other species，such as K. ananosma，K. coccinea， and K. heteroclita. Moreover，kadcoccilactones A(123)，B(124)， and P(122)were also isolated from K. coccinea and K. heteroclita，respectively.(Table 11，Figure 11)
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Table 1114(13→12)-abeo-cycloartanes(M)isolated from genus Kadsura Kaempf. ex Juss |
 | Figure 11 Structures oftriterpenoids(M)isolated from genus Kadsura Kaempf. ex Juss |
4)Norcycloartane(N) There was only one norcycloartane triterpenoid isolatd from the plants of genus Kadsura Kaempf. ex Juss. Micranoic acid B(125)，an octanor-triterpenoid due to the loss of the entire C-17 side chain，was isolated from K. angustifolia(Sun et al，2011).(Figure 12)
 | Figure 12 Structures oftriterpenoids(N and O)isolated from genus Kadsura Kaempf. ex Juss |
5)Kadlongilactone-type triterpenoids (O) Eleven kadlongilactone-type triterpenoids were isolated from the plants of genus Kadsura Kaempf. ex Juss. Kadlongilactones A−F(126−131)had been isolated from the leaves and stems of K. longipedunculata， and some of them were also isolated from K. coccinea and K. angustifolia. Since these compounds featured an unprecedented rearranged hexacyclic system，they were assigned to a new group，named kadlongilactone-type triterpenoids. Subsequent studies on K. coccinea led to the isolation of other five compounds，kadcoccilactones K−O(132−136).(Table 12，Figure 12)
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Table 12Kadlongilactone-type triterpenoids(O)isolated from genus Kadsura Kaempf. ex Juss |
In earlier years，more than 60 highly oxygenated polycyclic nortriterpenoids had been isolated from the plants of genus Schis and ra Michx.， and some scholars assigned this series of unique nortriterpenoids as Schis and ra nortrit- erpenoids(Xiao et al，2008). But the lastest phytochemical studies showed 19 compounds were isolated from Kadsura plants. Kadcoccilactones A−F(146−151)，H−J(152−154) and wuweizidilactone B(155)had been isolated from K. coccinea(Gao et al，2008a). Another eight compounds，named kadnanolactones A(137)，F(138)，G(139)，H(140)，I(141)，micr and ilactones B(143)，C(142)， and wuweizidilactone H(144)，were isolated from K. ananosma(Yang et al，2010a). Moreover，kadsuphilactone A(145)was isolated from K. philippinensis(Shen et al，2005a).(Figure 13)
 | Figure 13 Structures of triterpenoids(P)isolated from genus Kadsura Kaempf. ex Juss |
There were two other-type triterpenoids including angustific acid A(156) and kadnanolactone E(157)isolated from K. angustifolia(Sun et al，2011) and K. ananosma(Yang et al，2010a)，respectively. Three new triterpenoids，kadcotriones A−C(158−160)were isolated from K. coccinea(Liang et al，2013).(Figure 14)
 | Figure 14 Structures oftriterpenoids(Q)isolated from genus Kadsura Kaempf. ex Juss |
Some other kinds of chemical constituents were also isolated from genus Kadsura Kaempf. ex Juss. including flavonoids，sesquiterpenoids，etc. Seven flavonoids were isolated and identified from K. oblongifolia(Liu et al，2009a)，including kaempferol-3-O-α-L-arabofuranoside，kaempferol-3- O-α-D-arabinopyranoside，quercetin-3-O-α-L-arabofuranoside，
quercetin-3-O-α-D-arabinopyranoside，quercetin-3-O-β-D-gluco- pyranoside，quercetin， and kaempferol. In addition，two guaianolide-type sesquiterpenoids(4β，9β-dihydroxy-1α，5α- H-guaia-6，10(14)-dien and 4β，9β，10α-trihydroxy-1α，5α-H- guaia-6-en)were isolated and identified from K. interior(Dong et al，2013).
3. DiscussionLignans and triterpenoids were the main chemical constituents from the plants of genus Kadsura Kaempf. ex Juss. as summarized above. According to our previous investigation，lignans and triterpenoids exhibited various activities，including
anti-HIV，antitumor，antihepatitis，anti-oxidant，anti-platelet aggregation，immunomodulatory activities，neuroprotective effect，depigmentation effect，etc(Wang et al，2013; Goh et al，2013; Liu et al，2014). Some promising compounds with good bioactivities were emerged，for example anti-HIV activity(gomisin G，kadsulignan N，etc)，antitumor activity(ananosic acids A−C，etc)，anti-oxidant activity(kadsuphilol C，kadsurin，etc)，antihepatitis activity(acetylepigomisin R，etc)，anti- platelet aggregation activity(heteroclitin D，etc)，neuro- protective effect(ananolignan F，ananonin M，etc)， and NO production inhibitory activity(kadsuralignans C，G，etc)(Liu et al，2014).
Genus Kadsura Kaempf. ex Juss. is a good source with considerable characteristic chemical constituents and potential bioactivities. With the development and improve- ment of pharmacological models，some valuable lead compounds would be acquired by continuous and in-depth studies. Moreover，some pharmacophylogenetics and structure-activity relationships would greatly increase the opportunity of finding new and promising lead compounds and promote the reasonable development and utilization of the plants in genus Kadsura Kaempf. ex Juss.
4. ConclusionPhytochemical studies on the plants of genus Kadusra Kaempf. ex Juss. led to the isolation and identification of more than 450 compounds，including 285 lignans and 160 triterpenoids. Lignans and triterpenoids are the main characteristic constituents from the plants of genus Kadsura Kaempf. ex Juss.， and some of them exhibit unprecedented structural skeleton and exciting bioactivities，which has brought great interests and challenges for phytochemists and pharmacologists. Genus Kadsura Kaempf. ex Juss.，the economically and medicinally important plants，consists of 16 species in the world，but only about eight species are investigated in-depth. So it is necessary to further carry out the chemical，pharmacological， and pharmacophylogenetic study on the other plants of genus Kadsura Kaempf. ex Juss.
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