General Information of Natural Product (ID: NP0374)
  Natural Product Name
(1R,4R,4Ar,6S,8Ar)-1,6-Dimethyl-4-Propan-2-Yl-3,4,4A,5,6,7,8,8A-Octahydro-2H-Naphthalen-1-Ol
  Synonyms
alpha-muurolol
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  Formula C15H28O
  Weight 224.38
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H28O/c1-10(2)12-7-8-15(4,16)14-6-5-11(3)9-13(12)14/h10-14,16H,5-9H2,1-4H3/t11-,12+,13+,14+,15+/m0/s1
  InChI Key RYSZDRWMTKGBFI-NJVJYBDUSA-N
  Isomeric SMILES C[C@H]1CC[C@@H]2[C@H](C1)[C@H](CC[C@@]2(C)O)C(C)C
  Canonical SMILES CC1CCC2C(C1)C(CCC2(C)O)C(C)C
  External Links PubChem ID 100949538

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Cassinia laevis
  Factor Name: Locality Variation [1]
              Species Info Factor Info
               Experiment Detail
Six samples of Cassinia laevis R. Br. (coughbush, wild rosemary) were gathered from Lowood, 45 km west of Brisbane to Murphy's Creek area 100 km west of Brisbane, Australia from 1994 to 1998. Samples were identified by a LAEV prefix. LAEV 1 and LAEV 4 were collected from the roadside verge of the Gatton-Toowoomba bypass road (Lat. 27° 32′ 21″ S; Long. 152° 14′ 28″ E). LAEV 2 and LAEV 5 were collected from a different location in the same area (Lat. 27° 33′ 08″ S; Long. 152° 15′ 00″ E). LAEV 7 were collected from the Murphy's creek area (Lat. 27° 31′ 05″ S; Long. 152° 04′ 15″ E), growing on the roadside and in an adjacent paddock. Sample LAEV 9, was collected from the roadside area of the Warrego Highway (Lat. 27° 32′ 10″ S; Long. 152° 27′ 12″ E). The collected leaf and flower samples had aromas of trampled grass with a slight hint of curry.
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               Factor Function
Spathulenol was the major compound in flower oils (8-12%) compared to leaf oils (0.3-4.0%) which had ledol(37.5-53.6%) as the major compound.
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               Factor Part Location NP Content
 
Flower: Sample 1 (Locality: roadside verge of the Gatton-Toowoomba, Brisbane, Queensland)
Flowers Brisbane, Queensland, Australia
NP Content: 0.4 %
 
Flower: Sample 4 (Locality: Lat. 27º 33′ 08″ S; Long. 152º 15′ 00″ E, Brisbane, Queensland)
Flowers Brisbane, Queensland, Australia
NP Content: 0.2 %
 
Flower: Sample 2 (Locality: roadside verge of the Gatton-Toowoomba, Brisbane, Queensland)
Flowers Brisbane, Queensland, Australia
NP Content: 0.6 %
 
Leaf: Sample 3 (Locality: Lat. 27º 33′ 08″ S; Long. 152º 15′ 00″ E, Brisbane, Queensland)
Leaves Brisbane, Queensland, Australia
NP Content: 0.3 %
 
Leaf: Sample 6 (Locality: Murphy's creek area, Brisbane, Queensland)
Leaves Brisbane, Queensland, Australia
NP Content: 0.2 %
      Species Name: Echinacea purpurea
  Factor Name: Plant Pathogen Infection [2]
              Species Info Factor Info
               Experiment Detail
Plant selection and virological tests: Before effecting the collection procedure, heathy and infected plants of E. purpurea grown in the open field at the Herb Garden of Casola Valsenio were selected and labelled by visual inspection of their aerial parts. The infection by CMV was associated with symptoms on both leaves and flowers. The most characteristic symptoms are yellow mosaic, ring and line-patterns on crinkled and deformed leaves that drop prematurely. The flowers, which may be smaller than normal, show color breaking with white or pale stripes on red petals. Shortening of the internodes is also very common, giving the plant a bushy appearance known as stunting. In Italian environmental conditions, these symptoms are best visible in the summer. On the other hand, plants appeared symptom-free were collected as healthy material. Plant collection: About 3-4 Kg fresh aerial part materials (70% stems, 10% leaves and 20% flowers) of healthy E. purpurea plants were collected in June 2000 at almost the end of flowering. An equivalent quantity of CMV-infected plants (evaluated by DAS-ELISA) was also collected; the percentage of leaves in the infected infected was about 6.0% as due to CMV presence that caused the premature leaf drop.
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               Factor Function
The oil from healthy material was rich in germacrene D (57.8%) and was more abundant. The infected materials afforded a lower oil content and significant quantitative variations in the oil composition. In particular, the observed percentage of germacrene D (52.6%) was reduced as were other sesquiterpene hydrocarbons. These variations, tested to be significant for all the compound-class fractions and individual major components, were ascribed to the cucumber mosaic cucumovirus (CMV) infection, the only fixed-effect variable that might affect the oil composition.
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               Factor Part Location NP Content
 
Healthy plant
Aerial parts Italy
NP Content: 2 %
 
Infected plants (cucumber mosaic cucumovirus)
Aerial parts Italy
NP Content: 1.5 %
      Species Name: Eugenia chlorophylla
  Factor Name: Developmental Stage Variation [3]
              Species Info Factor Info
               Experiment Detail
Plant material was collected at vegetative stage (stems and leaves,September 2005) and at flowering stage (leaves and flowers,December 2004), inCuritiba,Parana state, Brazil.
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               Factor Function
Thirty-four components were identified, representing more than 80% of total oil. The major components were beta-caryophyllene (flowers-12.8%), caryophyllene oxide (stems-17.2%), globulol (stems-16.5%; leaves-22.5% at vegetative stage and 18.9% at flowering stage), 1-epi-cubenol (stems-10.9%), epi-alpha-muurolol (stems-16.8%) and alpha-cadinol (stems-12.1%; flowers-10.1%).
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               Factor Part Location NP Content
 
Flower: flowering stage
Flowers Brazil
NP Content: 1.2 %
 
Leaf: flowering stage
Leaves Brazil
NP Content: 1 %
 
Leaf: vegetative stage
Leaves Brazil
NP Content: 1 %
 
Stem: vegetative stage
Stems Brazil
NP Content: 1 %
      Species Name: Eugenia dysenterica
  Factor Name: Developmental Stage Variation [4]
              Species Info Factor Info
               Experiment Detail
Unripe, semi-ripe, and ripe fruits of E. dysenterica were collected in rural area of Abadia de Goias city (S 16° 45′ 1″, W 49° 25′ 5″, 850 m), Goias State, Brazil, in October 2002.
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               Factor Function
Limonene (25.8% and 24.6%), (E)-beta-ocimene (20.3% and 21.7%) and beta-pinene (12.0% and 14.2%) were the major compounds in the unripe and semi-ripe stages, respectively, while gamma-muurolene (25.8%), beta-caryophyllene (18.4%) and alpha-humulene (15.4%) became the major compounds in ripe fruits. The concentration of monoterpenes was high in the unripe and semi-ripe stages and decreased afterwards, while sesquiterpenes were intensively synthesized only in the last part of the ripening process.
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               Factor Part Location NP Content
 
Fruit: Ripe fruit stage
Ripe fruits Brazil
NP Content: 1.6 %
      Species Name: Helichrysum arenarium
  Factor Name: Locality Variation; Developmental Stage Variation [5]
              Species Info Factor Info
               Experiment Detail
The plant material was collected in eastern Lithuania (July-August, 2002). Numbers of growing localities of H. arenarium with yellow (Y) and orange (O) flowers were as follows: Svencionys district (Zalavas) and Ukmerge district (Sventupe).
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               Factor Function
The 68 constituents identified comprised 73.8-90.7% of the total oil content. It was found that the principal constituents were: beta-caryophyllene (in three inflorescence and one leaf oil), delta-cadinene (in two leaf oils), octadecane (in one leaf oil) and heneicosane (in one inflorescence sample). Monoterpenes and oxygenated monoterpenes made up 4.0-13.9%, aliphatic hydrocarbons 0.4-35.3%, and sesquiterpenes 24.7-71.2% of the oils.
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               Factor Part Location NP Content
 
Inflorescence: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 3.1 %
 
Inflorescence: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Inflorescence Eastern Lithuania
NP Content: 0.9 %
 
Leaf: (Flower colour: Yellow) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: 1.3 %
 
Leaf: (Flower colour: Orange) + (Locality: Ukmerge District, Eastern Lithuania)
Leaves Eastern Lithuania
NP Content: < 0.05 %
      Species Name: Hyptis marrubioides
  Factor Name: Locality Variation [6]
              Species Info Factor Info
               Experiment Detail
Hyptis marrubioides were collected in March 2003 at the mature vegetative stage from their natural habitat; 20 randomised individual plants at the same age representing the local population were collected as homogenous samples from each locality: (A) Lavras (21° 14′ S/44° 59′ W), at an altitude of 919 m; (B) Tiradentes (21° 6′ S/44° 10 m W), 927 m.
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               Factor Function
The results were submitted to Principal Component and Cluster analysis which allowed three groups of oils to be distinguished with respect to sampling site and post-harvested process: cluster I (fresh leaves and fresh or dried stems from Lavras site) with high percentage of caryophylla-4(14),8(15)-dien-5beta-ol (16.7%) and eudesma-4(15),7-dien-1beta-ol (12.8%); cluster II (dried leaves and stems from Tiradentes site) with epi-longipinanol (16.2%) rich oil, and cluster III (dried leaves from Lavras) containing a high content of beta-caryophyllene (17.4%) and alpha-copaene (10.1%). Canonical discriminant analysis showed that is possible to accurately predict 100% well-classification in the original clusters using beta-caryophyllene, epi-longipinanol and caryophylla-4(14),8(15)-dien-5beta-ol as predictor variables. The whole or sliced plant materials resulted in similar chemical composition.
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               Factor Part Location NP Content
 
Whole fresh Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 5.5 %
 
Sliced fresh Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 5.2 %
 
Whole dried Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 1.9 %
 
Sliced dried Leaves: (Locality: Lavras, Brazil)
Leaves Brazil
NP Content: 2.7 %
 
Whole fresh Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 7.2 %
 
Whole dried Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 5 %
 
Sliced dried Stems: (Locality: Lavras, Brazil)
Stems Brazil
NP Content: 5.3 %
 
Whole dried Leaves: (Locality: Tiradentes, Brazil)
Leaves Brazil
NP Content: 1.8 %
 
Sliced dried Leaves: (Locality: Tiradentes, Brazil)
Leaves Brazil
NP Content: 2.4 %
 
Whole dried Stems: (Locality: Tiradentes, Brazil)
Stems Brazil
NP Content: 2.7 %
 
Sliced dried Stems: (Locality: Tiradentes, Brazil)
Stems Brazil
NP Content: 4.1 %
      Species Name: Juniperus thurifera
  Factor Name: Altitude Variation; High Temperature Treatment [7]
              Species Info Factor Info
               Experiment Detail
The plant materials were collected for P1: 2900 m, Ait Akak, Oukaimden, Atlas Mts, Morocco, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 12/12/2003; P2, 2200 m, Plateau of Matat, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns, 18/03/2003; P3: 2000 m, Foret Islane, Oukaimden, Atlas Mts, N. Achak, A. Romane and M. Mahroug, 3 trees, ns,12/12/2003. A portion of the leaves from each of the three trees (per population) were air dried for 16 days at room temperature (ca. 22 &#8451) to produce the dried leaf samples.
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               Factor Function
The oil yields from fresh leaves showed on differences among geographical sources. Air dried leaves appeared to yield more oil at the highest elevation (1.03%, Ait Lkak, 2900 m) than lower sites (0.67%, Plateau of Matat, 2200 m; 0.57%, Foret Islane, 2000 m). The essential oils from each geographic site had very similar composition in fresh versus air dried leaves. The essential oils from provenance Ait Lkak and Plateau of Matat were very similar and characterized by a high sabinene content (21.2, 35.9%), in contrast to 10.% sabinene from the provenance Foret Islane. The oil from Foret Islane had a high delta-cadinene content with 12.7%, whereas Aik Akak and Plateau of Matat contained only 0.6 and 0.8%.
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               Factor Part Location NP Content
 
Dry leaf: (Locality: Foret Islane, Tensift Al Haouz-Marrakech, Morocco; Altitude 2000 m)
Dry leaves Foret Islane, Tensift Al Haouz - Marrakech, Morocco
NP Content: <0.1 %
 
Dry leaf: (Locality: Ait Lkak, Tensift Al Haouz-Marrakech, Morocco; Altitude 2900 m)
Dry leaves Ait Lkak, Tensift Al Haouz - Marrakech, Morocco
NP Content: <0.1 %
 
Dry leaf: (Locality: Plateau of Matat, Tensift Al Haouz-Marrakech, Morocco; Altitude 2200 m)
Dry leaves Plateau of Matat, Tensift Al Haouz - Marrakech, Morocco
NP Content: <0.1 %
 
Fresh leaf: (Locality: Foret Islane, Tensift Al Haouz-Marrakech, Morocco; Altitude 2000 m)
Fresh leaves Foret Islane, Tensift Al Haouz - Marrakech, Morocco
NP Content: <0.1 %
      Species Name: Melaleuca quinquenervia
  Factor Name: Chemotype Comparison [8]
              Species Info Factor Info
               Experiment Detail
Plant material: Leaves of M. quinquenervia were collected from January to October during the ten year period (1992-2001) on mainly East part of Madagascar island and in particular on Toamasina, Mananjary, Manakara, Farafangana, Vangaindrano, Moramanga, and Ambatondrazaka locations. Olfactory chemotype selection: During the years 1992-1995, since the price for (E)-nerolidol and viridiflorol chemotypes was very strong, leaf collection was done on trees chosen after olfactory selection by a chief harvester who compared the olfactory threshold of crumple leaves with our clearly identified oil samples. After 1996, collection was done at random and no particular attention in leaf harvesting was taken.
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               Factor Function
Niaouli essential oils from Madagascar were classified into three chemotypes using Principal Component Analysis (PCA): a cineole chemotype (49-62%), a viridiflorol chemotype (21-36%) and an (E)-nerolidol chemotype (56-95%). The 1,8-cineole chemotype is widespread, representing 92% of the samples investigated if the leaf collection is done at random.
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               Factor Part Location NP Content
 
Chemotype (Cineole type)
Leaves Madagascar
NP Content: 0.13 %
 
Chemotype (Viridiflorol type)
Leaves Madagascar
NP Content: 0.82 %
 
Chemotype (E-nerolidol type)
Leaves Madagascar
NP Content: 0.18 %
      Species Name: Pimenta pseudocaryophyllus
  Factor Name: Developmental Stage Variation [9]
              Species Info Factor Info
               Experiment Detail
Two samples were collected in Sao Goncalo do Abaete, one in July 2000 and the other in November 2005, in periods of post-anthesis and preanthesis, respectively.
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               Factor Function
Thirty compounds were detected in the samples collected in Sao Goncalo do Abaete. Among the identified compounds, 53.8% are sesquiterpenes and 42.3% are monoterpenes. The majority components in the two samples were neral and geranial. The sample in anthesis presented a lower percentage of neral (21.4%) and geranial (36.5%) than the sample in pre-anthesis, whose percentages of neral and geranial were 33.6% and 47.2%, respectively.
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               Factor Part Location NP Content
 
post-anthesis stage
Leaves Sao Goncalo do Abaete, Brazil
NP Content: 1 %
      Species Name: Pinus sylvestris
  Factor Name: Locality Variation [10]
              Species Info Factor Info
               Experiment Detail
The branches of pine were collected in July, 1996 in 15 different locations in Lithuania in the following regions: Western part (Silute, Jurbarkas, Kursiu Nerija), Eastern part (Salcininkai, Zarasai, Moletai), Southern part (Varena, Trakai, Radviliskis) and central part (Ukmerge, Jonava, Kaisiadorys). The branches in each location were collected from the trees in approximately 1 km radius.
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               Factor Function
More than 70 constituents were identified (64 positively and 10 tentatively) in the oils. alpha-Pinene (18.5-33.0%) and delta-3-carene (9.1-24.6%) were dominating constituents with the only one exception when the germacrene-4-ol content in one of the samples was 13.2%. The important bornyl acetate content varied from 0.5% to 3.0%. The main sesquiterpenes were beta-caryophyllene, germacrene D, bicyclogermacrene, delta-cadinene, gamma-cadinene, germacrene D-4-ol, cubenol (2.0-5.1%) and alpha-cadinol (1.9-7.7%).
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               Factor Part Location NP Content
 
Locality: Jonava, Lithuania
Branches Jonava, Lithuania
NP Content: 0.5 %
 
Locality: Jurbarkas, Lithuania
Branches Jurbarkas, Lithuania
NP Content: 0.4 %
 
Locality: Neringa (Smiltyne), Lithuania
Branches Neringa (Smiltyne), Lithuania
NP Content: 0.5 %
 
Locality: Salacininkai, Lithuania
Branches Salacininkai, Lithuania
NP Content: 0.7 %
 
Locality: Varena, Lithuania
Branches Varena, Lithuania
NP Content: 0.7 %
 
Locality: Vilnius, Lithuania
Branches Vilnius, Lithuania
NP Content: 0.6 %
 
Locality: Zarasai (Sunele), Lithuania
Branches Zarasai (Sunele), Lithuania
NP Content: 0.2 %
      Species Name: Teucrium flavum
  Factor Name: Month Variation; Developmental Stage Variation [11]
              Species Info Factor Info
               Experiment Detail
The aerial parts of T. flavum were collected in different periods from December to July 2006, from plants growing along the Ionic coast of Sicily (Italy). LF 1-LF 2-LF 3: represent the composition of leaf oils of plant samples collected in December (vegetative stage), February (pre-flowering stage) and April (budding stage) respectively; FL: flower oil; FR: fruit oil.
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               Factor Function
Some components, in all investigated plant parts, remained more or less constant during all the different phases of the plant cycle life. Worthy of note, considering the leaf oils, was that beta-pinene, limonene and germacrene D increased in the pre-flowering stage, while a series of esters and alpha-copaene, beta-caryophyllene, viridiflorol, Tmuurolol and phytol increased in the budding stage (LF3); the vegetative stage oil is generally characterized by a rich chemical composition and some constituents such as isoamyl hexanoate, alpha-humulene, bicyclogermacrene, beta-bisabolene and alpha-bisabolol reached their highest levels in this oil. In the flower oil, linalool and 1-octen-3-yl acetate were the main components compared to the amounts found in the other oils. Fruit oil composition was relatively oil poor, with beta-bisabolene, caryophyllene oxide, cadin-4-en-1-ol and phytone as the major constituents.
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               Factor Part Location NP Content
 
Harvesting time: February; pre-flowering stage
Leaves Italy
NP Content: 0.1 %
 
Flower oil
Flowers Italy
NP Content: 0.2 %
 
Fruit oil
Fruits Italy
NP Content: 0.4 %
References
1 Cassinia laevis R. Br. Flower and Leaf Essential Oils
2 Characterization of the Essential Oils of Healthy and Virus Infected Echinacea purpurea (L.) Moench Plants
3 Chemical Composition and Antimicrobial Activity of Essential Oils of Eugenia chlorophylla (Myrtaceae)
4 Changes in Volatile Constituents During Fruit Ripening of Wild Eugenia dysenterica DC.
5 Chemical Composition of the Essential Oils of Wild Helichrysum arenarium (L.) with Differently Colored Inflorescences from Eastern Lithuania
6 Composition and Chemical Variability in the Essential Oil of Hyptis marrubioides Epl.
7 Effect of the Leaf Drying and Geographic Sources on the Essential Oil Composition of Juniperus thurifera L. var. Africana Maire from the Tensift-Al Haouz, Marrakech Region
8 Main Industrial Niaouli (Melaleuca quinquenervia) Oil Chemotype Productions from Madagascar
9 Chemical Differences in the Essential Oil of Pimenta pseudocaryophyllus (Gomes) L. R. Landrum Leaves from Brazil
10 Composition of Essential Oils of Pinus sylvestris L. from Different Locations of Lithuania
11 Seasonal Variations of Teucrium flavum L. Essential Oil